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Iberdomide
Iberdomide
CAS 1323403-33-3
as HCl: 1560678-63-8
MW 449.5 g/mol, C25H27N3O5
(S)-3-(4-((4-(Morpholinomethyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione
(3S)-3-[7-[[4-(morpholin-4-ylmethyl)phenyl]methoxy]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione
8/13/2026, APPROVAL 2026, FDA 2026, Zenbexus, cc-220, cc 220, 8V66F27X44, 79L3645KFI
To be used in combination with daratumumab and hyaluronidase-fihj and dexamethasone for adults with multiple myeloma who have received at least one prior line of therapy, including a proteasome inhibitor and an immunomodulatory agent
Iberdomide is a modulator of the E3 ubiquitin ligase complex containing cereblon (CRL4-CRBN E3 ubiquitin ligase), with immunomodulating and pro-apoptotic activities. Upon administration, iberdomide specifically binds to the cereblon (CRBN) part of the ligase complex, thereby affecting the ubiquitin E3 ligase activity, and targeting certain substrate proteins for ubiquitination. This induces the proteasome-mediated degradation of certain transcription factors, including Ikaros (IKZF1) and Aiolos (IKZF3) which are transcriptional repressors in T-cells. This leads to a reduction of their protein levels, and the modulation of the immune system, including activation of T-lymphocytes. In addition, this leads to a downregulation of other proteins, including interferon regulatory factor 4 (IRF4), which plays a key role in the proliferation of certain cancer cell types. CRBN, the substrate recognition component of the E3 ubiquitin ligase complex, plays a key role in the ubiquitination of certain proteins.
Iberdomide, sold under the brand name Zenbexus, is an anti-cancer medication used for the treatment of multiple myeloma.[1] It is a cereblon-modulating protein degrader[1] and a thalidomide analog.[2]. It is taken By mouth.[1]
Iberdomide was approved for medical use in the United States in August 2026.[3]
Medical uses
Iberdomide is indicated in combination with daratumumab, hyaluronidase, and dexamethasone for the treatment of adults with multiple myeloma who have received at least one prior line of therapy including a proteasome inhibitor and an immunomodulatory agent.[3]
Society and culture
Legal status
Iberdomide was approved for medical use in the United States in August 2026.[12] The U.S. Food and Drug Administration (FDA) granted the application for iberdomide priority review, breakthrough therapy, and orphan drug designations.[3]
Names
Iberdomide is the international nonproprietary name.[13]
Iberdomide is sold under the brand name Zenbexus.[14]
SYN
SYN
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2011100380&_cid=P12-MSZHNS-67589-1
5.2 3-[4-(4-MORPHOLIN-4-YLMETHYL-BENZYLOXY)-1-OXO- 1,3-DIHYDRO-ISOINDOL-2-YL]-PIPERIDINE-2,6-DIONE
Step 3 : To the THF solution of methyl 5-amino-4-(4-(4- (morpholinomethyl)benzyloxy)-1-oxoisoindolin-2-yl)-5-oxopentanoate (40 g, 83 mmol), was added potassium 2-methylpropan-2-olate (9.80 g, 87 mmol) portion wise at 0°C. The mixture was stirred at this temperature for 30 minutes. To the reaction mixture, was added 45 mL of 1N HCl solution, followed by 200 mL of saturated NaHCO3 solution. The mixture was diluted with 500 mL of EtOAc at 0°C, stirred for 5 minutes and separated. The organic layer was washed with water (50 mL × 3) and brine (100 mL), and concentrated on rota-vap to give a white solid, which was stirred in diethyl ether (300 mL) to give a suspension. The suspension was filtered to give 3-[4-(4-morpholin-4-ylmethyl-benzyloxy)-1-oxo-1,3-dihydro-isoindol-2-yl]-piperidine-2,6-dione as white solid (28.5g, 72% yield): HPLC: Waters Symmetry C18, 5μm, 3.9 × 150 mm, 1 mL/min, 240 nm, gradient to 95/5 acetonitrile/0.1% H3PO4 in 5 min,: tR = 4.78 min (98.5%); mp: 209-21 1 °C; 1H NMR (DMSO-d6) δ 1.86 – 2.09 (m, 1H, CHH), 2.29 – 2.38 (m, 4H, CH2,CH2), 2.44 (dd, J = 4.3, 13.0 Hz, 1H, CHH), 2.53 – 2.64 (m, 1H, CHH), 2.82 – 2.99 (m, 1H, CHH), 3.46 (s, 2H, CH2), 3.52 – 3.61 (m, 4H, CH2,CH2), 4.18 – 4.51 (m, 2H, CH2), 5.11 (dd, J = 5.0, 13.3 Hz, 1H, NCH), 5.22 (s, 2H, CH2), 7.27 – 7.38 (m, 5H, Ar), 7.40 – 7.53 (m, 3H, Ar), 10.98 (s, 1H, NH); 13C NMR (DMSO-d6) δ 22.36, 31.21, 45.09, 51.58, 53.14, 62.10, 66.17, 69.41,
114.97, 115.23, 127.64, 128.99, 129.81, 129.95, 133.31, 135.29, 137.68, 153.50, 168.01,
170.98, 172.83; LCMS: 465; Anal Calcd for C25H27N3O5 + 0.86 H2O: C, 64.63; H, 6.22; N,
9.04; Found: C, 64.39; H, 6.11; N, 8.89; H2O, 3.24.
5.61 (S)-3-[4-(4-MORPHOLIN-4-YLMETHYL-BENZYLOXY)-1-OXO-1,3- DIHYDRO-ISOINDOL-2-YL]-PIPERIDINE-2,6-DIONE
[386] Step 1 : Preparation of (S)-4-[4-(4-Bromomethyl-benzyloxy)-1-oxo-1,3-dihydro-isoindol-2-yl]-4-carbamoyl-butyric acid methyl ester
To a 2-L round bottom flask was charged methyl 5-amino-4-(4-hydroxy-1-oxoisoindolin-2-yl)-5-oxopentanoate (30 g, 103 mmol), 1,4-bis(bromomethyl)benzene (81 g, 308 mmol) and potassium carbonate (14.19 g, 103 mmol) and acetonitrile (1.2 L). The mixture was stirred at room temperature for 10 min and heated to 50°C for 12 hours. The reaction mixture was allowed to cool to room temperature. The mixture was filtered and the filtrate was concentrated on rota-vap. The resulted solid was dissolved in CH2Cl2 and loaded on 2 silica gel columns (330 g each) eluted using CH2Cl2/MeOH to give 4-[4-(4-bromomethyl-benzyloxy)-1-oxo-1,3-dihydro-isoindol-2-yl]-4-carbamoyl-butyric acid methyl ester as white solid (40g, 82%). 1H NMR (DMSO-d6) δ 1.98 – 2.13 (m, 1H, CHH), 2.14 – 2.23 (m, 1H, CHH), 2.23 – 2.32 (m, 2H, CHH, CHH), 3.50 (s, 3H, CH3), 4.34 – 4.63 (m, 2H, CH2), 4.67 – 4.80 (m, 3H, CH2, NCH), 5.25 (s, 4H, CH2), 7.19 (s, 1H, NHH), 7.24 – 7.34 (m, 2H, Ar), 7.41 – 7.54 (m, 5H, Ar), 7.58 (br. s., 1H, NHH)
[387] Step 2: Preparation of (S)-4-Carbamoyl-4-[4-(4-morpholin-4-ylmethyl-benzyloxy)-1-oxo-1,3-dihydro-isoindol-2-yl]-butyric acid methyl ester
To the CH2Cl2 solution of methyl 5-amino-4-(4-(4-(bromomethyl)benzyloxy)-1-oxoisoindolin-2-yl)-5-oxopentanoate (36.5 g, 77 mmol) was added morpholine (14.72 ml, 169 mmol) at 0 °C. The mixture was stirred at 0 °C for 1 hr. The mixture was added 200 mL of CH2Cl2, washed with water (100mL × 2) and brine (100 ml), dried in Na2SO4 and concentrated to give (S)-4-Carbamoyl-4-[4-(4-morpholin-4-ylmethyl-benzyloxy)-1-oxo-1,3-dihydro-isoindol-2-yl]-butyric acid methyl ester as white foam (39 g, 100%). M.p. 66-68 °C; Waters Symmetry C-18, 3.9 X 150 mm, 5 micro, 1 mL/min, 240 nm, isocratic 15/85 CH3CN/ 0.1% H3PO4 in H2O: 7.92 min (99%). 1H NMR (DMSO-d6) δ 2.00 – 2.12 (m, 1HH CHH), 2.14 – 2.22 (m, 1H, CHH), 2.22 – 2.29 (m, 2H, CHH,CHH), 2.30 – 2.39 (m, 4H, CH2,CH2), 3.46 (s, 2H, CH2), 3.50 (s, 3H, CH3), 3.53 – 3.63 (m, 4H, CH2,CH2), 4.28 – 4.59 (m, 2H, CH2), 4.73 (dd, J= 4.7, 10.2 Hz, 1H, NCH), 5.22 (s, 2H, CH2), 7.14 – 7.23 (m, 1H, NHH), 7.26 – 7.39 (m, 4H, Ar), 7.41 – 7.51 (m, 3H, Ar), 7.58 (s, 1H, NHH). 13C NMR (DMSO-d6) δ 24.82, 30.33, 44.78, 51.24, 53.12, 53.38, 62.09, 66.14, 69.35, 114.66, 115.12, 127.60, 129.00, 129.55, 130.18, 133.43, 135.31, 137.66, 153.42, 167.84, 171.73, 172.46; Anal Calcd for C26H31N3O6+ 0.3 H2O: C% 64.13; H% 6.54; N% 8.63; Found: C% 63.89; H% 6.39; N% 8.56.
[388] Step 3: Preparation of (S)-3-[4-(4-morpholin-4-ylmethyl-benzyloxy)-1-oxo- 1 , 3-dihydro-isoindol-2-yl]-piperidine-2,6-dione
To the THF solution of (S)-methyl 5-amino-4-(4-(4-(morpholinomethyl)benzyloxy)-1-oxoisoindolin-2-yl)-5-oxopentanoate (45 g, 93 mmol) was added potassium 2-methylpropan-2-olate (10.49 g, 93 mmol) portion wise (2g X5) at -78 °C. The mixture was stirred at this temperature for 30 min then was added 250 mL of 1N HCl solution followed by 200 mL of saturated NaHCO3 solution. The mixture was extracted with CH2Cl2 (150 mLx2). The organic layer was washed with water (50 mL × 3) and brine (100 mL), concentrated on rota-vap to give a white solid, which was then recrystallized from CH3CN
(100 mL) to give (S)-3-[4-(4-morpholin-4-ylmethyl-benzyloxy)-1-oxo-1,3-dihydro-isoindol-2-yl]-piperidine-2,6-dione as white solid (32g, 76%). mp: 140-142 °C. LC-MS m/e= 450. HPLC: Waters Symmetry C18, 5μm, 3.9 x 150 mm, 1 mL/min, 240 nm, isocratic
15/85 CH3CN/0.1% H3PO4 in 5 min,: tR = 5.61 min (99.5%); Chiral AGP C 18 4.0 × 150 mm, 5 μm 10/90 i-propanol/ 10 mM NH4Ac in 20 min,: tR = 10.07 min (99.5%); 1H NMR
(DMSO-d6) δ 2.28 – 2.38 (m, 4H, CH2,CH2), 2.44 (dd, J= 4.2, 13.1 Hz, 1H, CHH), 2.53- 2.63 (m, 1H, CHH), 2.79 – 3 02 (m, 1H, CHH), 3.49 – 3.69 (m, 4H, CH2,CH2), 4.11 – 4.52
(m, 2H, CH2), 5.11 (dd, J= 5.1, 13.2 Hz, 1H, NCH), 5.22 (s, 2H, CH2), 7.33 (d, J= 7.7 Hz,
4H, Ar), 7.40 – 7.52 (m, 3H, Ar), 10.97 (s, ΙΗ, ΝΗ). 13C NMR (DMSO-d6) δ 22.33, 31.18,
45.06, 51.55, 53.11, 62.07, 66.14, 69.38, 114.96, 115.20, 127.61, 128.97, 129.78, 129.93,
133.28, 135.27, 137.67, 153.48, 167.97, 170.95, 172.80. LC-MS: 465; Anal Calcd for
C25H27N3O5 C: 66.80%; H: 6.05%; N: 9.35%. Found: C:66.59%; H:5.79%; N:9.26%.
PAT
- PRMT5 inhibitors and uses thereofPublication Number:US-12448388-B2Grant Date:2025-10-21
- KRAS G12D modulating compoundsPublication Number:US-12448400-B2Grant Date:2025-10-21
- Arylmethoxy isoindoline derivatives and compositions comprising them and methods of use thereofPublication Number:ES-2956743-T3Priority Date:2010-02-11Grant Date:2023-12-27
- Arylmethoxy isoindoline derivatives and compositions comprising and methods of using the samePublication Number:AU-2013245487-A1Priority Date:2010-02-11
- Arylmethoxy isoindoline derivatives and compositions comprising and methods of using the samePublication Number:AU-2013245487-B2Priority Date:2010-02-11Grant Date:2016-03-10
- Arylmethoxy isoindoline derivatives and compositions comprising and methods of using the samePublication Number:EP-3599236-B1Priority Date:2010-02-11Grant Date:2023-08-23
- Treating cancerPublication Number:US-2025325586-A1
- Arylmethoxy isoindoline derivatives and compositions comprising and methods of using the samePublication Number:US-9822094-B2Priority Date:2010-02-11Grant Date:2017-11-21
- Arylmethoxy isoindoline derivatives and compositions comprising and methods of using the samePublication Number:EP-4289838-A2Priority Date:2010-02-11
- Arylmethoxy isoindoline derivatives and compositions comprising and methods of using the samePublication Number:US-2018037567-A1Priority Date:2010-02-11
- Arylmethoxy isoindoline derivatives and compositions comprising them and methods of using themPublication Number:ES-2713482-T3Priority Date:2010-02-11Grant Date:2019-05-22
- Arylmethoxy Isoindoline Derivatives and Compositions Comprising and Methods of Using the SamePublication Number:US-2011196150-A1Priority Date:2010-02-11
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References
References
- “U.S. Prescribing Information” (PDF). Packageinserts.bms.com. Retrieved 18 August 2026.
- Gao, Shaobing; Wang, Shichao; Song, Yongping (December 2020). “Novel immunomodulatory drugs and neo-substrates”. Biomarker Research. 8 (1): 2. doi:10.1186/s40364-020-0182-y. PMC 6953231. PMID 31938543.
- “FDA grants accelerated approval to iberdomide with daratumumab and hyaluronidase-fihj and dexamethasone for multiple myeloma”. U.S. Food and Drug Administration (FDA). 13 August 2026. Retrieved 16 August 2026.
This article incorporates text from this source, which is in the public domain. - Ye, Ying; Gaudy, Allison; Schafer, Peter; Thomas, Michael; Weiss, Daniel; Chen, Nianhang; et al. (May 2021). “First-in-Human, Single- and Multiple-Ascending-Dose Studies in Healthy Subjects to Assess Pharmacokinetics, Pharmacodynamics, and Safety/Tolerability of Iberdomide, a Novel Cereblon E3 Ligase Modulator”. Clinical Pharmacology in Drug Development. 10 (5): 471–485. doi:10.1002/cpdd.869. PMC 8246954. PMID 32969202.
- Bjorklund, Chad C.; Kang, Jian; Amatangelo, Michael; Polonskaia, Ann; Katz, Mark; Chiu, Hsiling; et al. (April 2020). “Iberdomide (CC-220) is a potent cereblon E3 ligase modulator with antitumor and immunostimulatory activities in lenalidomide- and pomalidomide-resistant multiple myeloma cells with dysregulated CRBN”. Leukemia. 34 (4): 1197–1201. doi:10.1038/s41375-019-0620-8. ISSN 1476-5551. PMC 7214241. PMID 31719682.
- van de Donk, Niels W.C.J.; Popat, Rakesh; Larsen, Jeremy; Minnema, Monique C.; Jagannath, Sundar; Oriol, Albert; et al. (5 November 2020). “First Results of Iberdomide (IBER; CC-220) in Combination with Dexamethasone (DEX) and Daratumumab (DARA) or Bortezomib (BORT) in Patients with Relapsed/Refractory Multiple Myeloma (RRMM)”. Blood. 136 (Supplement 1): 16–17. doi:10.1182/blood-2020-137743. S2CID 228828103.
- Thieblemont, Catherine; Munoz, Javier; Tucci, Alessandra; Visco, Carlo; Cartron, Guillaume; Corradini, Paolo; et al. (15 November 2022). “Iberdomide (CC-220) Monotherapy or in Combination with an Anti-CD20 Monoclonal Antibody As Effective Therapy in Patients with Relapsed/Refractory Lymphoma: Early Results from a Phase 1/2 Study”. Blood. 140 (Supplement 1): 569–572. doi:10.1182/blood-2022-162559. S2CID 256795199.
- Lonial, Sagar; Amatangelo, Michael; Popat, Rakesh; Minnema, Monique C.; Zonder, Jeffrey A.; Larsen, Jeremy; et al. (13 November 2019). “Translational and Clinical Evidence of a Differentiated Profile for the Novel CELMoD, Iberdomide (CC-220)”. Blood. 134 (Supplement_1): 3119. doi:10.1182/blood-2019-124298. S2CID 209233746.
- Amatangelo, Michael; Bjorklund, Chad C.; Kang, Jian; Polonskaia, Ann; Viswanatha, Sridevi; Thakurta, Anjan (29 November 2018). “Iberdomide (CC-220) Has Synergistic Anti-Tumor and Immunostimulatory Activity Against Multiple Myeloma in Combination with Both Bortezomib and Dexamethasone, or in Combination with Daratumumab in Vitro”. Blood. 132 (Supplement 1): 1935. doi:10.1182/blood-2018-99-113383. S2CID 91382999.
- Lonial, Sagar; Popat, Rakesh; Hulin, Cyrille; Jagannath, Sundar; Oriol, Albert; Richardson, Paul G; et al. (November 2022). “Iberdomide plus dexamethasone in heavily pretreated late-line relapsed or refractory multiple myeloma (CC-220-MM-001): a multicentre, multicohort, open-label, phase 1/2 trial”. The Lancet Haematology. 9 (11): e822–e832. doi:10.1016/S2352-3026(22)00290-3. PMID 36209764. S2CID 252779185.
- Merrill, Joan T.; Werth, Victoria P.; Furie, Richard; van Vollenhoven, Ronald; Dörner, Thomas; Petronijevic, Milan; et al. (17 March 2022). “Phase 2 Trial of Iberdomide in Systemic Lupus Erythematosus”. New England Journal of Medicine. 386 (11): 1034–1045. doi:10.1056/NEJMoa2106535. PMID 35294813. S2CID 247499089.
- Feuerstein, Adam (14 August 2026). “FDA clears Bristol multiple myeloma therapy, marking debut of new drug class”. STAT. Retrieved 14 August 2026.
- World Health Organization (2018). “International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 79”. WHO Drug Information. 32 (1). hdl:10665/330941.
- “U.S. FDA Grants Accelerated Approval to Bristol Myers Squibb’s First CELMoD Therapy Zenbexus, in Combination with Daratumumab and Hyaluronidase-fihj and Dexamethasone (ZDd) for Patients with Multiple Myeloma, as Early as First Relapse”. Bristol Myers Squibb (Press release). 13 August 2026. Retrieved 16 August 2026.
External links
- “Iberdomide ( Code – C129048 )”. EVS Explore.
- “Iberdomide Hydrochloride ( Code – C141516 )”. EVS Explore.
- Clinical trial number NCT04975997 for “Open-label Study Comparing Iberdomide, Daratumumab and Dexamethasone (IberDd) Versus Daratumumab, Bortezomib, and Dexamethasone (DVd) in Participants With Relapsed or Refractory Multiple Myeloma (RRMM) (EXCALIBER-RRMM)” at ClinicalTrials.gov
 | |
| Clinical data | |
|---|---|
| Trade names | Zenbexus |
| Other names | CC-220 |
| AHFS/Drugs.com | zenbexus |
| License data | US DailyMed: Iberdomide |
| Routes of administration | By mouth |
| Drug class | Cereblon-modulating protein degrader |
| ATC code | None |
| Legal status | |
| Legal status | US: ℞-only[1] |
| Identifiers | |
| IUPAC name | |
| CAS Number | 1323403-33-3as HCl: 1560678-63-8 |
| PubChem CID | 67335295as HCl: 72793904 |
| IUPHAR/BPS | 9618 |
| DrugBank | DB12101 |
| ChemSpider | 52085251 |
| UNII | 8V66F27X44as HCl: 79L3645KFI |
| KEGG | D11134as HCl: D11135 |
| ChEMBL | ChEMBL3989927 |
| Chemical and physical data | |
| Formula | C25H27N3O5 |
| Molar mass | 449.507 g·mol−1 |
| 3D model (JSmol) | Interactive imageas HCl: Interactive image |
| SMILES | |
| InChI | |
////////iberdomide, ANAX LABS, APPROVAL 2026, FDA 2026, Zenbexus, APPROVAL 2026, FDA 2026, Zenbexus, cc-220, cc 220, 8V66F27X44, 79L3645KFI
Ratutrelvir
Ratutrelvir
CAS 2929236-94-0
MF C27H32F3N5O4 MW547.6 g/mol
(1R,2S,5S)-N-[(1S)-1-cyano-2-(2-oxo-1,3-dihydroindol-3-yl)ethyl]-3-[(2S)-3,3-dimethyl-2-[(2,2,2-trifluoroacetyl)amino]butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
(1R,2S,5S)-N-{(1S)-1-cyano-2-[(3RS)-2-oxo-2,3-dihydro-1H-indol-3-yl]ethyl}-3-[(2S)-3,3-dimethyl-2-(2,2,2-trifluoroacetamido)butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
protease inhibitor, antiviral, TRX01, 83-0060, TRX 01, VR2S5588W2,
Ratutrelvir is an investigational new drug that is being evaluated by Traws Pharma[1] for the treatment of COVID-19 infections.[2][3] It is a 3C-like protease inhibitor.[3][4]
Clinical trials
Ratutrelvir is currently in a phase 2 clinical trial to test the effectiveness and safety of the drug in patients with COVID-19[5] and a preliminary analysis of the results has been released.[6]
Ratutrelvir (also known as TRX01 or 83-0060) is an investigational, oral antiviral medication being developed by Traws Pharma for the treatment of mild-to-moderate COVID-19.
Key Characteristics
- Mechanism: It functions as a covalent inhibitor of the SARS-CoV-2 main protease (\(M^{pro}\) / 3CL protease), preventing the virus from replicating.
- Ritonavir-Free: Unlike Paxlovid, ratutrelvir does not require a metabolic booster like ritonavir. This prevents severe drug-drug interactions and broadens its usability.
- Dosing: It is designed as a once-daily oral regimen taken over 10 days.
Clinical Development & Trial Results
According to Phase 2 data released by Traws Pharma in early 2026:
- Efficacy: Shows a comparable or faster time to sustained symptom resolution compared to Paxlovid.
- No Viral Rebound: Patients treated with ratutrelvir experienced no viral rebound events.
- Paxlovid-Ineligible Benefit: The drug successfully treated patients who could not take Paxlovid due to medical contraindications.
- Fewer Side Effects: It reported fewer treatment-related adverse events (10% vs 23.3% for Paxlovid) and avoids taste disturbances (dysgeusia).
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2023093834&_cid=P11-MSWMDL-65476-1
Example 1: Preparation of (1R,2S,5S)-N-((2S)-1-amino-1-carbonyl-3-(2-carbonyldihydroindole-3-yl)propane-2-yl)-3-((S)-3,3-dimethyl-2-(2,2,2-trifluoroacetamido)butyryl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide (compound 1)
[0138]The synthesis route is as follows:
The structural characterization data of compound 1-P2 are as follows:
[0153]m/z(ESI):548[M+H] 。
[0154]
1H NMR:(400MHz,DMSO-d6)δ10.58-10.41(m,1H),9.42-9.00(m,2H),7.39-7.26(m,1H),7.21-7.13(m,1H),7.03-6.78(m,2H),5.30-5.16(m,1H),4.44-4.30(m,1H),4.22(s,1H),4.00-3.86(m,1H),3.75-3.64(m,1H),3.58-3.47(m,1H),2.19-2.05(m,1H),1.63-1.54(m,1H),1.35(d,J＝7.7Hz,1H),1.04(s,3H),1.01-0.96(m,2H),0.94(s,2H),0.90-0.79(m,9H)。
PAT
Synthesis of compound (I)
31.
ASB
Synthesis of compound (I)
31.
ASB
PAT
- Compounds for treatment a coronavirus infectionPublication Number:WO-2023245162-A2Priority Date:2022-06-17
- Compounds for treatment a coronavirus infectionPublication Number:EP-4540227-A2Priority Date:2022-06-17
- Pyrrolidine antiviral compoundPublication Number:WO-2023093834-A1Priority Date:2021-11-26
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References
References
- WO 2023245162, Rogovoy B, Kysil V, Berishvili V, Pauza CD, Zapata JC, Moreno SM, Li H, Orry A, Lam PC, Abagyan R, Savchuk N, “Compounds for treatment a coronavirus infection”, published 2023-12-21, assigned to Trawsfynydd Therapeutics Inc.
- “International Nonproprietary Names for Pharmaceutical Substances (INN) Recommended INN: List 94” (PDF). WHO Drug Information. 39 (3). World Health Organization: 809–1060 (976). 2025.
- “Travatrelvir – Traws Pharma”. AdisInsight. Springer Nature Switzerland AG. Retrieved 5 July 2026.
- “Ratutrelvir | Ligand page”. IUPHAR/BPS Guide to PHARMACOLOGY.
- “Early-stage Trial to Determine a Safe and Effective Dose for Ratutrelvir in Patients With Mild to Moderate COVID-19”. ClinicalTrials.gov. U.S. National Library of Medicine. 17 January 2026. Clinical trial record for NCT07157007. Retrieved 5 July 2026.
- Contagion Editorial Team (8 July 2026). “Traws Pharma Reports Differentiated COVID-19 and Influenza Antiviral Progress”. Contagion Live.
 | |
| Clinical data | |
|---|---|
| Other names | 83-0060, TRX01 |
| Identifiers | |
| IUPAC name | |
| CAS Number | 2929236-94-0 |
| PubChem CID | 169861725 |
| IUPHAR/BPS | 13737 |
| UNII | VR2S5588W2 |
| Chemical and physical data | |
| Formula | C27H32F3N5O4 |
| Molar mass | 547.579 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
///////////ratutrelvir, anax labs, protease inhibitor, antiviral, TRX01, 83-0060, TRX 01, VR2S5588W2,
Ralometostat
Ralometostat
CAS 2760481-53-4
MF C21H23N5O2S MW409.51
(2R,5S)-N-(6-Amino-5-methyl-3-pyridinyl)-2-(5-benzothiazolyl)-5-methyl-α-oxo-1-piperidineacetamide
1-Piperidineacetamide, N-(6-amino-5-methyl-3-pyridinyl)-2-(5-benzothiazolyl)-5-methyl-α-oxo-, (2R,5S)-
N-(6-amino-5-methylpyridin-3-yl)-2-[(2R,5S)-2-(1,3-benzothiazol -5-yl)-5-methylpiperidin-1-yl]-2-oxoacetamide
N-(6-amino-5-methylpyridin-3-yl)-2-[(2R,5S)-2-(1,3-benzothiazol -5-yl)-5-methylpiperidin-1-yl]-2-oxoacetamide
antineoplastic, TNG908, TNG 908, X7CRL5YNN5
Ralometostat (also known as TNG908) is an experimental, orally active oncology drug designed to treat advanced or metastatic solid tumors. It is classified as a potent, brain-penetrant, and selective methylthioadenosine (MTA)-cooperative PRMT5 inhibitor.
Developed by Tango Therapeutics, the drug targets specific genetic deletions frequently found in various human cancers.
Mechanism of Action
Ralometostat relies on a concept called synthetic lethality.
- Target Deletion: It targets cancers that have a deletion of the methylthioadenosine phosphorylase (MTAP) gene. This deletion occurs in roughly 10% to 15% of all human cancers.
- The “Trap”: When the MTAP gene is missing, a metabolite called MTA builds up heavily inside the tumor cells.
- Selective Killing: Ralometostat specifically binds to this PRMT5•MTA complex. This enables it to selectively kill MTAP-deleted cancer cells while sparing normal, healthy tissues.
This targeted approach bypasses the severe bone marrow toxicities caused by older, non-selective first-generation PRMT5 inhibitors.
Key Clinical Features
- Blood-Brain Barrier Penetration: The drug is chemically optimized to cross the blood-brain barrier. This makes it highly effective in evaluating tumors within the central nervous system (CNS).
- Therapeutic Targets: It is studied in clinical oncology settings for several tumor types, including:
- Glioblastoma (GBM) and brain metastases.
- Non-small cell lung cancer (NSCLC).
- Malignant peripheral nerve sheath tumors (MPNST) and soft tissue sarcomas.
- Urothelial carcinoma and cholangiocarcinoma.
- Safety and Tolerability of TNG908 in Patients With MTAP-deleted Solid TumorsCTID:
- NCT05275478
- Phase:
- Phase 1/Phase 2
- Status:
- Terminated
- Date:
- 2026-04-15
Chemical & Trial Profile
Development Phase: Evaluated in Phase I/II clinical trials (such as NCT05275478) as a standalone precision therapy and in combination with other targeted inhibitors
Ralometostat is an orally available small molecule inhibitor of protein arginine methyltransferase 5 (PRMT5), with potential antiproliferative and antineoplastic activities. Upon oral administration, ralometostat selectively binds to PRMT5 and inhibits its function. By inhibiting its methyltransferase activity, levels of both monomethylated and dimethylated arginine residues in histones H2A, H3 and H4 are decreased. This modulates the expression of genes involved in several cellular processes, including cellular proliferation. This may increase the expression of antiproliferative genes and/or decrease the expression of genes that promote cell proliferation, which may lead to decreased growth of rapidly proliferating cells, including cancer cells. PRMT5, a type II methyltransferase that catalyzes the formation of both omega-N monomethylarginine (MMA) and symmetric dimethylarginine (sDMA) on histones and a variety of other protein substrates involved in signal transduction and cellular transcription, is overexpressed in several neoplasms and is essential for the viability of cancer and normal cells. Elevated levels are associated with decreased patient survival. Methylthioadenosine phosphorylase (MTAP) is deleted in certain cancer cells leading to an accumulation of methylthioadenosine (MTA). As MTA binds to and partially inhibits PRMT5, MTAP-null cancer cells are specifically sensitive to PRMT5 inhibitors. This may spare normal, healthy cells that are without MTAP-deletions and lower systemic toxicity.
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=US358600101&_cid=P11-MSTR3S-83508-1
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=US399951504&_cid=P11-MSTR3S-83508-1
Example 1. The synthesis of N-(6-amino-5-methylpyridin-3-yl)-2-((2R,5S)-2-(benzo[d]thiazol-5-yl)-5-methylpiperidin-1-yl)-2-oxoacetamide (Compound (I)) and N-(6-amino-5-methylpyridin-3-yl)-2-((2S,5R)-2-(benzo [d]thiazol-5-yl)-5-methylpiperidin-1-yl)-2-oxoacetamide (Compound (Ia))
| The enantiomers were separated by chiral HPLC (column: IC II, Hexane-IPA-MeOH, 50-25-25, 12 ml/min as mobile phase) to give the two individual enantiomers Compound (Ia)N-(6-amino-5-methylpyridin-3-yl)-2-((2 S, 5R)-2-(benzo[d]thiazol-5-yl)-5-methylpiperidin-1-yl)-2-oxoacetamide (161 mg, 393.16 μmol, 97.28% yield) RetTime=32.4 min, [α]21D=−176.7°(c=0.1 g/100 mL, EtOH) and Compound (I)N-(6-amino-5-methylpyridin-3-yl)-2-((2R,5S)-2-(benzo[d]thiazol-5-yl)-5-methylpiperidin-1-yl)-2-oxoacetamide (160 mg, 390.72 μmol, 96.68% yield) RetTime=45.8 min, [α]21D=+191.5° (c=0.1 g/100 mL, EtOH). |
Compound (I): RT (IC, Hexane-IPA-MeOH, 50-25-25, 0.6 ml/min)=47.098 min.
Compound (Ia) RT (IC, Hexane-IPA-MeOH, 50-25-25, 0.6 ml/min)=35.176 min.
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References
- Discovery of TNG908: A Selective, Brain Penetrant, MTA-Cooperative PRMT5 Inhibitor That Is Synthetically Lethal with MTAP-Deleted CancersPublication Name:Journal of Medicinal ChemistryPublication Date:2024-04-10PMCID:PMC11056935PMID:38595098DOI:10.1021/acs.jmedchem.4c00133
- [Intracellular protein breakdown. VI. Isolation, properties and biological significance of cathepsin D from rat liver]Publication Name:Acta biologica et medica GermanicaPublication Date:1976PMID:9765
PAT
Piperidin-1-yl-N-pyridin-3-yl-2-oxoacetamide derivatives useful for the treatment of MTAP-deficient and/or MTA-accumulating cancersPublication Number:
KR-20230094196-APriority Date:
2020-07-31
- Compounds and methods of usePublication Number:US-2023113778-A1Priority Date:2020-07-31
- Piperidin-1-yl-N-pyridin-3-yl-2-oxoacetamide derivatives useful in the treatment of MTAP deficiency and/or MTA accumulation cancersPublication Number:CN-116568677-APriority Date:2020-07-31
- Compounds and methods of usePublication Number:US-11999727-B2Priority Date:2020-07-31Grant Date:2024-06-04
- Compounds and methods of usePublication Number:US-2022127256-A1Priority Date:2020-07-31
- Compounds and methods of usePublication Number:US-12264154-B2Priority Date:2020-07-31Grant Date:2025-04-01
- Crystalline form of n-(6-amino-5-methylpyridin-3-yl)-2-(benzo[d]thiazol-5-yl)-5-methylpiperidin-1-yl)-2-oxoacetamide, pharmaceutical compositions and methods of use thereofPublication Number:EP-4448517-A1Priority Date:2021-12-17
- Compounds and methods of usePublication Number:US-2024279219-A1Priority Date:2020-07-31
- Compounds and methods of usePublication Number:US-2024228478-A1Priority Date:2020-07-31
- Compounds and methods of usePublication Number:US-11492350-B2Priority Date:2020-07-31Grant Date:2022-11-08
- Piperidin-1-yl-n-pyrydine-3-yl-2-oxoacetamide derivatives useful for the treatment of mtap-deficient and/or mta-accumulating cancersPublication Number:EP-4188920-A1Priority Date:2020-07-31
- Prmt5 inhibitors for use in methods of treating mta-accumulating cancerPublication Number:WO-2025217297-A1Priority Date:2024-04-09
- Prmt5 inhibitor for use in cancer therapyPublication Number:WO-2024170488-A1Priority Date:2023-02-13
- Methods of treatment of cancerPublication Number:TW-202423435-APriority Date:2022-08-15
- MTA synergizes with PRMT5 inhibitors for cancer treatmentPublication Number:CN-119730853-APriority Date:2022-08-15
- Mta-cooperative prmt5 inhibitors for use in the treatment of cancerPublication Number:WO-2024038004-A1Priority Date:2022-08-15
//////////ralometostat, anax labs, antineoplastic, TNG908, TNG 908, X7CRL5YNN5
Pruvonertinib
Pruvonertinib
CAS 2064269-82-3
MF C27H32N8O2 MW500.6 g/mol
N-[2-[2-(dimethylamino)ethyl-methylamino]-4-methoxy-5-[[4-(8-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]prop-2-enamide
- 2-Propenamide, N-[2-[[2-(dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(8-methylimidazo[1,2-a]pyridin-3-yl)-2-pyrimidinyl]amino]phenyl]-
- N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(8-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)prop-2-enamide
N-(2-{2-(dimethylamino)ethylamino}-4-methoxy-5-{[4-(8-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)prop2-enamide
epidermal growth factor receptor tyrosine kinase inhibitor, antineoplastic, YK-029A, YK 029A, HXJ9459HFK
Pruvonertinib is an orally bioavailable, mutant-selective, third-generation epidermal growth factor receptor (EGFR) inhibitor, with potential antineoplastic activity. Upon oral administration, pruvonertinib targets, binds to and inhibits the activity of EGFR with exon 20 insertion (Ex20ins) activating mutations, the gatekeeper mutation T790M and some other rare mutations, thereby preventing EGFR-mediated signaling. This may both induce cell death and inhibit tumor growth in EGFR-overexpressing tumor cells. EGFR, a receptor tyrosine kinase mutated in many tumor cell types, plays a key role in tumor cell proliferation and tumor vascularization.
Pruvonertinib (also known by its development code YK-029A) is an investigational, orally bioavailable, mutant-selective, third-generation epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor. Developed by Puhe Pharmaceutical, it is designed as an antineoplastic agent primarily targeting advanced non-small cell lung cancer (NSCLC) with specific resistant mutations.
Mechanism of Action
- Target Specificity: Binds selectively to mutant forms of EGFR.
- Resistance Targeting: Inhibits the gatekeeper T790M mutation and exon 20 insertion (Ex20ins) mutations.
- Scaffold Lineage: Structurally derived as an analogue of the established oncology drug osimertinib.
- Tumour Regression: Blockades downstream EGFR-mediated signaling to induce cell death and stunt tumor vascularization.
Clinical Development & Indications
- Primary Indication: Treatment of advanced, metastatic, or biomarker-positive Non-Small Cell Lung Cancer (NSCLC).
- Development Status: Pre-commercial asset undergoing active clinical trial screening and testing evaluations.
- Regulatory Track: Listed under the World Health Organization (WHO) Proposed International Nonproprietary Names (INN) List 132.
SYN
Publication Name:European Journal of Medicinal Chemistry, Publication Date:2023-10-05
PMID:37406381DOI:10.1016/j.ejmech.2023.115590
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=US298712718&_cid=P10-MSQW7F-15668-1
N-(2-methoxy-4-(N 1,N 2,N 2-trimethyl-1,2-ethylenediamine-1-yl)-5-acrylamidephenyl)-4-(8-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine (hereinafter referred to as “Compound 1”) is a novel EGFR inhibitor represented by Formula (I):
The above compound is described in Chinese Patent Application 201610679161.7, and the content of which can be used as a reference for the present application
Step 7: Preparation of Drug Substance H (i.e. Compound 1)
| Intermediate F (1.01 kg, 2.26 mol) was added to a mixed solution of acetonitrile (4.73 kg) and water (1.52 kg), and the temperature was lowered to 0 to 5° C. 3-Chloropropionyl chloride (373 g, 2.94 mol) was added dropwise. After the addition, the mixture was stirred at 0˜5° C. for 0.5 h. The completion of the reaction was detected. |
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References
- Pyrimidinylaminobenzenes for treating lung cancer with distant metastasisPublication Number:WO-2024094064-A1Priority Date:2022-11-02
- Pyrimidinylaminobenzenes for lung cancer treatmentPublication Number:US-2024226101-A1Priority Date:2021-04-30
- Pyrimidinylaminobenzenes for lung cancer treatmentPublication Number:EP-4330256-A1Priority Date:2021-04-30
- Pyrimidinylaminobenzene for lung cancer treatmentPublication Number:CN-117561254-APriority Date:2021-04-30
- Pyrimidinylaminobenzene for lung cancer treatmentPublication Number:KR-20240027583-APriority Date:2021-04-30
- N-heteroaromatic amide derivatives for treatment of cancerPublication Number:EP-3950686-A1Priority Date:2019-03-29
- Azaaromatic amide derivatives for the treatment of cancerPublication Number:US-2022177473-A1Priority Date:2019-03-29
- Crystal form and salt form of n-phenyl-2-aminopyrimidine compound, and preparation method thereforPublication Number:US-2020216444-A1Priority Date:2017-07-19
- Crystal form and salt form of N-phenyl-2-aminopyrimidine compound, and preparation method thereforPublication Number:US-10906901-B2Priority Date:2017-07-19Grant Date:2021-02-02
/////////pruvonertinib, anax labs, epidermal growth factor receptor tyrosine kinase inhibitor, antineoplastic, YK-029A, YK 029A, HXJ9459HFK
Prifetrastat
Prifetrastat
CAS 2569008-99-5
MFC19H18N4O5S MW414.4 g/mol
N-(6-((1H-Pyrazol-1-yl)methyl)-4-methoxybenzo[d]isoxazol-3-yl)-2-methoxybenzenesulfonamide
2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide
antineoplastic, PF-07248144, PF 07248144, Solid tumours, CANCER, KAT6-IN-1, GN6DU4ZE30
Prifetrastat is an inhibitor of MYST histone acetyltransferase (HAT) KAT6, with potential antineoplastic activity. Upon administration, prifetrastat targets and binds to KAT6, and inhibits the acetylation of histones and other nonhistone substrates. This may disrupt gene expression and inhibit the proliferation of tumors that overexpress KAT6. KAT6A (MOZ; MYST3) and KAT6B (MORF; MOZ2; MYST4), commonly amplified genes in solid tumors, play key roles in cell cycle regulation and in tumorigenesis.
Prifetrastat (also known as PF-07248144) is an investigational, first-in-class small molecule drug that acts as a selective inhibitor of the epigenetic modifiers KAT6A and KAT6B. It is primarily studied as an antineoplastic agent for hormone receptor-positive (ER+/HER2–) advanced or metastatic breast cancer.
Mechanism of Action
- Inhibits KAT6A and KAT6B histone acetyltransferases to block abnormal tumor cell growth.
- Suppresses lineage-specific gene expression tied to estrogen receptor signaling and drug resistance.
- Induces cell cycle arrest and tumor senescence.
Clinical Development
- Evaluated in clinical trials (such as phase 1/2 and phase 3 evaluations) for patients whose breast cancer progressed after prior endocrine therapy and CDK4/6 inhibitors.
- Commonly tested in combination regimens alongside anti-estrogen therapies like fulvestrant
Prifetrastat (also known as PF-07248144) is an investigational, first-in-class small molecule drug that acts as a selective inhibitor of the epigenetic modifiers KAT6A and KAT6B. It is primarily studied as an antineoplastic agent for hormone receptor-positive (ER+/HER2–) advanced or metastatic breast cancer.
Mechanism of Action
- Inhibits KAT6A and KAT6B histone acetyltransferases to block abnormal tumor cell growth.
- Suppresses lineage-specific gene expression tied to estrogen receptor signaling and drug resistance.
- Induces cell cycle arrest and tumor senescence.
Clinical Development
- Evaluated in clinical trials (such as phase 1/2 and phase 3 evaluations) for patients whose breast cancer progressed after prior endocrine therapy and CDK4/6 inhibitors.
- Commonly tested in combination regimens alongside anti-estrogen therapies like fulvestrant
- Phase IIIHER2 negative breast cancer
- Phase IISolid tumours
- No development reportedBreast cancer
- 07 Aug 2026Prifetrastat is still in phase II development in Solid-tumours (Combination therapy, Late-stage disease, Metastatic disease, Second-line therapy or greater) in USA, Australia, Japan, China, South Korea (PO, Tablet) (NCT04606446)
- 07 Aug 2026Prifetrastat is still in phase II development in Solid-tumours (Monotherapy, Late-stage disease, Metastatic disease, Second-line therapy or greater) in USA, Australia, Japan, China, South Korea (PO, Tablet) (NCT04606446)
- 28 Jul 2026No recent reports of development identified for phase-I development in Breast-cancer(Metastatic disease) in USA (PO)
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020254946&_cid=P12-MSO1IP-41527-1
Example 45: Preparation of 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide according to Scheme C (Route A).
To a suspension of 4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-amine (A-2) (2.5 g, 10 mmol) in pyridine (8.0 mL) was added 2-methoxybenzene-1-sulfonyl chloride (3.17 g, 15.4 mmol). The reaction was stirred at 120 °C for 1.5 h. The mixture was cooled to room temperature and diluted with MeOH. The resulting suspension was filtered. and the filter cake was washed with MeOH (30 mL). The solids were dissolved in DCM (50 mL) and MeOH (30 mL) was added. The DCM was removed under vacuum
and the precipitate was collected by filtration. The filter cake was dried by lyophilization to provide 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (2.5 g, 59% yield) as a white solid. 1 H NMR (400 MHz, DMSO-d6) d 10.18 (s, 1H), 7.87 (d, J= 2.0 Hz, 1H), 7.80 (dd, J=1.6, 7.9 Hz, 1H), 7.66– 7.59 (m, 1H), 7.49 (d, J=1.5 Hz, 1H), 7.19 (d, J=8.3 Hz, 1H), 7.09 (t, J=7.7 Hz, 1H), 6.83 (s, 1H), 6.74 (s, 1H), 6.30 (t, J=2.0 Hz, 1H), 5.44 (s, 2H), 3.82 (s, 3H), 3.78 (s, 3H); m/z (ESI+) 415.0 (M+H) + .
Example 45: Alternative preparation of 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide according to Scheme D.
A 100 mL reactor equipped with an overhead stirrer was charged with 4-methoxy-6-(1H-pyrazol-1-ylmethyl)-1,2-benzoxazol-3-amine (A-2) (10.00 g, 40.94 mmol), 2-methoxybenzenesulfonyl chloride (10.15 g, 49.13 mmol), and acetonitrile (100 mL). The resulting suspension was stirred at 25 °C for 55 minutes. Via pipette, dimethylsulfoxide (0.36 mL, 4.09 mmol) was added in one portion. Via syringe, 3,5-lutidine (14.8 mL, 122.82 mmol) was added dropwise over 15 minutes. The resulting light-yellow suspension was stirred at 25 °C for 18 hours to reach >98% conversion as judged by LCMS. The reaction mixture was acidified with 1 M aq. HCl (100 mL), then
concentrated to ~80 mL (rotary evaporator, 40 °C, 85 mbar). The slurry was treated with additional 1 M aq. HCl (40 mL) to rinse down the walls of the vessel, then stirred at 20 °C for 2.5 hours. The resulting precipitate was collected by suction filtration. The filter cake was washed with water (2 x 50 mL), then dried under vacuum at 35 °C for 48 hours, affording crude 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (15.2 g, 90% yield, 98% purity by LCMS) as a solid. m/z 415.1 (M+H) + .
To purify the crude product, a suspension of crude 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (14.00 g, 33.78 mmol) in dichloromethane (210 mL) was heated in a 40 °C bath until a clear solution was obtained (10 minutes). The mixture was filtered, and the filtrate returned to a clean reaction vessel, using additional dichloromethane (70 mL) to quantitate the transfer. Ethyl acetate (140 mL) was added to the solution over 2 minutes, then the mixture stirred for 2.5 hours. No crystallization was observed, so the solution was concentrated under reduced pressure (200 mbar) to remove dichloromethane (volume was reduced by about 70 mL). More ethyl acetate (140 mL) was added to the residue, and the mixture stirred at room temperature for 21 hours. The resulting suspension was concentrated under reduced pressure (40 °C, 200 mbar) to about 280 mL, then stirred at room temperature for 3 hours. The solids were collected by filtration, with additional ethyl acetate (70 mL) used to rinse the reaction vessel and filter cake. The filter cake was dried in a vacuum oven at 35 °C for 23 hours, affording 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (12.0 g, 85% yield, 97.9% purity by UPLC, no single impurity larger than 0.5%) as a solid. m/z 415.1 (M+H) + .
To purify further, a suspension of 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (2.0 g, 4.73 mmol) in acetone (80 mL) was heated to reflux (bath temperature 55 °C) with stirring for 2 hours. While the mixture was still heated, ethyl acetate (30 mL) was added slowly, so that the internal temperature remained above 45 °C. The resulting slurry was concentrated to about 30 mL under mild vacuum (bath temp 65 °C), then cooled slowly at a rate of 1 °C/min to 20 °C (~31 minutes). The resulting precipitate was collected by suction filtration. The filter cake dried under vacuum at 50 °C for 22 hours, yielding 2-methoxy-N-{4-methoxy-6-[(1H-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamide (Example 45) (1.825 g, 93% yield, 99.5% purity by UPLC) as a crystalline solid. 1 hour
NMR (400 MHz, CHLOROFORM-d) d 8.14 (dd, J=1.7, 7.8 Hz, 1H), 8.04 (s, 1H), 7.59 -7.51 (m, 2H), 7.44 (d, J=2.2 Hz, 1H), 7.14 – 7.06 (m, 1H), 6.95 (d, J=8.3 Hz, 1H), 6.78 (d, J=0.6 Hz, 1H), 6.45 (s, 1H), 6.32 (t, J=2.1 Hz, 1H), 5.38 (s, 2H), 3.97 (s, 3H), 3.91 (s, 3H).
PAT
PAT
Scheme 1
Step 2
In an inerted reactor were added 6-((1 H-pyrazol-1-yl)methyl)-4-methoxybenzo[d]isoxazol-3-amine (lnt-4, 27.5 Kg, 112.6 mol, 1 equiv.), 2-methoxybenzenesulfonyl chloride (lnt-5, 33.9 Kg, 168.9 mol, 1.5 equiv.) and THF (248 L, 9-L/Kg). A solution of sodium te/Y-butoxide in THF (2 M, 197 L, 394.1 mol, 3.5 eq.) was added to the stirred mixture at 20 °C over 4 h. At the end of the addition the line was rinsed with THF (27.5 L, 1 L/Kg) and the mixture stirred for a further 1 h. Following reaction completion water (413 L, 15 L/Kg) was added at once followed by slow addition of aq. HCI (2 M, 197 L, 394.1 mol, 3.5 equiv.). The mixture was left stirring overnight, then the slurry was filtered, washed twice with CH3OH (82.5 L, 3 L/Kg) and dried to afford the title compound as a white solid (42.32 Kg, 90.6% yield).
1H NMR (400 MHz, DMSO) 5 10.09 (s, 1 H), 7.87 (dd, J = 2.3, 0.7 Hz, 1 H), 7.81 (dd, J = 7.8, 1.7 Hz, 1 H), 7.63 (ddd, J = 8.4, 7.4, 1.7 Hz, 1 H), 7.50 (dd, J = 1.8, 0.7 Hz, 1 H), 7.10 (td, J = 7.6, 1 .0 Hz, 1 H), 6.84 (d, J = 1 .0 Hz, 1 H), 6.30 (t, J = 2.1 Hz, 1 H), 5.44 (s, 2H), 3.83 (s, 3H), 3.79 (s, 3H). 13C NMR (101 MHz, DMSO) 5 164.82, 156.92, 154.39, 151.76, 144.13, 139.80, 135.73, 131.03, 130.43, 127.66, 120.52, 113.34, 106.25, 106.17, 104.42, 101.33, 56.51, 56.42, 55.01. HRMS: Ci9Hi8N4O5S+ [M+1 ]+ calculated:
415.1072; measured: 415.1071.
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References
- Benzisoxazole sulfonamide derivativesPublication Number:HR-P20231501-T1Priority Date:2019-06-18
- Benzisoxazole sulfonamide derivativesPublication Number:US-12371425-B2Priority Date:2019-06-18Grant Date:2025-07-29
- Benzisoxazole sulfonamide derivativesPublication Number:EP-3986890-B9Priority Date:2019-06-18Grant Date:2025-04-16
- Benzisoxazole sulfonamide derivativesPublication Number:EP-4299135-B1Priority Date:2019-06-18Grant Date:2025-08-06
- Benzisoxazole sulfonamide derivativesPublication Number:AU-2020296361-A1Priority Date:2019-06-18
- Benzisoxazole sulfonamide derivativesPublication Number:EP-4299135-A2Priority Date:2019-06-18
- Benzisoxazole sulfonamide derivativesPublication Number:TW-202115048-APriority Date:2019-06-18
- Benzisoxazole sulfonamide derivativesPublication Number:CN-114364672-BPriority Date:2019-06-18Grant Date:2024-09-06
- Benzisoxazole sulfonamide derivativesPublication Number:EP-3986890-A1Priority Date:2019-06-18
- Benzisoxazole sulfonamide derivativesPublication Number:US-11492346-B2Priority Date:2019-06-18Grant Date:2022-11-08
- Benzisoxazole sulfonamide derivativesPublication Number:CA-3143666-A1Priority Date:2019-06-18
- Benzisoxazole sulfonamide derivativesPublication Number:CN-114364672-APriority Date:2019-06-18
- Benzisoxazole sulfonamide derivativesPublication Number:EP-3986890-B1Priority Date:2019-06-18Grant Date:2023-11-15
- Benzisoxazole sulfonamide derivativesPublication Number:WO-2020254946-A1Priority Date:2019-06-18
- Kat6 inhibitor and combinations for breast cancer treatmentPublication Number:EP-4181920-B1Priority Date:2020-07-15Grant Date:2025-09-10
- Benzisoxazole sulfonamide derivativesPublication Number:KR-20220024671-APriority Date:2019-06-18
- Benzisoxazole Sulfonamide DerivativesPublication Number:US-2023174522-A1Priority Date:2019-06-18
- Benzisoxazole Sulfonamide DerivativesPublication Number:US-2020399258-A1Priority Date:2019-06-18
- Benzisoxazole sulfonamide derivativesPublication Number:CA-3143666-CPriority Date:2019-06-18Grant Date:2024-06-11
- Dosing regimens comprising a kat6 inhibitor for the treatment of cancerPublication Number:WO-2024023703-A1Priority Date:2022-07-29
- Dosing regimens comprising a kat6 inhibitor for the treatment of cancerPublication Number:EP-4561571-A1Priority Date:2022-07-29
- Kat6 inhibitor methods and combinations for cancer treatmentPublication Number:EP-4181920-A1Priority Date:2020-07-15
- Kat6 inhibitor methods and combinations for cancer treatmentPublication Number:WO-2022013369-A1Priority Date:2020-07-15
- KAT6 inhibitor methods and combinations for cancer treatmentPublication Number:CN-116113407-APriority Date:2020-07-15
- Crystalline form of 2-methoxy-n-{4-methoxy-6-[(1h-pyrazol-1-yl)methyl]-1,2-benzoxazol-3-yl}benzene-1-sulfonamidePublication Number:WO-2025141469-A1Priority Date:2023-12-26
- Sulfonamide compound and use thereofPublication Number:WO-2025098417-A1Priority Date:2023-11-08
- MYST InhibitorsPublication Number:US-2025122182-A1Priority Date:2023-09-27
- Dosing regimens comprising a kat6 inhibitor for the treatment of cancerPublication Number:TW-202415373-APriority Date:2022-07-29
- Dosing regimen comprising KAT6 inhibitors for treating cancerPublication Number:CN-119604288-APriority Date:2022-07-29
///////////prifetrastat, anax labs, antineoplastic, PF-07248144, PF 07248144, Solid tumours, CANCER, KAT6-IN-1, GN6DU4ZE30
Plodicitinib
Plodicitinib
CAS 2360992-48-7
MF C19H22FN7O2 MW399.42
1-[(3S,4R)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]-4-fluoropiperidin-1-yl]prop-2-en-1-one
1-[(3S,4R)-3-({2-[(1-ethyl-1H-pyrazol-4-yl)amino]-7Hpyrrolo[2,3-d]pyrimidin-4-yl}oxy)-4-fluoropiperidin-1-yl]prop2-en-1-one
Janus tyrosine kinase 3/TEC family kinase inhibitor, antiinflammatory, veterinary, SX5UEP3JXA
Plodicitinib is a Janus tyrosine kinase 3/TEC family kinase inhibitor with anti-inflammatory activity.
Plodicitinib is a small-molecule, dual Janus tyrosine kinase 3 (JAK3) and TEC family kinase (specifically BTK) inhibitor that exhibits strong anti-inflammatory properties.
Mechanism of Action
The compound blocks specific enzymatic pathways involved in cellular signaling:
- JAK3 Inhibition: It targets Janus kinase 3, which plays an essential role in transmitting signals for cytokines that regulate immune cell development and activation.
- TEC/BTK Inhibition: It blocks Bruton’s tyrosine kinase (BTK), a component vital for B-cell development and activation. [1, 2]
- Combined Effect: By blocking these pathways, it suppresses the overactive immune and inflammatory responses that drive autoimmune and allergic conditions.
Applications and Development Status
- Veterinary Medicine: In early 2026, Daewoong Pharmaceutical submitted an application to the Animal and Plant Quarantine Agency in South Korea for commercial approval of plodicitinib. It is being positioned as a specialized, companion animal-only treatment to manage atopic dermatitis in dogs.
- Research Use: In the scientific community, it is actively utilized as a laboratory tool compound to study kinase signaling pathways and inflammatory disease models.
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=US306969271&_cid=P22-MSL6QJ-67927-1
Example 4: Preparation of 1-(cis-3-((2-((1-ethyl-1H-pyrazol-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one
19.3 mg (yield: 27.8%) of the title compound was obtained in the same manner as in Example 1, except that cis-tert-butyl-4-fluoro-3-hydroxypiperidine-1-carboxylate was used instead of trans-tert-butyl-4-fluoro-3-hydroxypiperidine-1-carboxylate in Example 1.
Example 5: Preparation of 1-((3S,4R)-3-((2-((1-ethyl-1H-pyrazol-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one
| 16.2 mg (yield: 57.4%) of the title compound was obtained in the same manner as in Example 1, except that tert-butyl(3S,4R)-4-fluoro-3-hydroxypiperidine-1-carboxylate was used instead of trans-tert-butyl-4-fluoro-3-hydroxypiperidine-1-carboxylate in Example 1. |
Example 25: Preparation of 1-((3S,4S)-3-((2-((1-ethyl-1H-pyrazol-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one
The compound of Example 1 was separated by CHIRALCEL OZ-H column to obtain the title compound with an analysis time of 10.1 minutes.
1H NMR (500 MHz, CD 3OD) δ 7.98-7.95 (m, 1H), 7.57-7.55 (m, 1H), 6.84-6.53 (m, 2H), 6.26-6.08 (m, 2H), 5.78-5.52 (m, 1H), 5.41-5.40 (m, 1H), 5.10-5.04 (m, 1H), 4.50-4.06 (m, 4H), 3.89-3.86 (m, 1H), 3.55-3.50 (m, 1H), 2.19-2.16 (m, 1H), 1.95-1.94 (m, 1H), 1.45-1.41 (m, 3H)
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2025121903&_cid=P22-MSL6W2-73218-1
1-((3S,4R)-3-((2-((1-ethyl-1H-pyrazole-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidine-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one is represented by the following chemical formula 1:
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References
- Tartrate salt of 1-((3s,4r)-3-((2-((1-ethyl-1h-pyrazol-4-yl)amino)-7h-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one, crystalline form thereof, and method for preparing samePublication Number:WO-2025121903-A1Priority Date:2023-12-05
- Method for preparation of 1-((3s,4r)-3-((2-((1-ethyl-1h-pyrazol-4-yl)amino)-7h-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one, and intermediate compounds thereofPublication Number:WO-2025121899-A1Priority Date:2023-12-05
- Phosphate salt of 1-((3s,4r)-3-((2-((1-ethyl-1h-pyrazol-4-yl)amino)-7h-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-fluoropiperidin-1-yl)prop-2-en-1-one, crystalline form thereof, and method for preparation thereofPublication Number:WO-2025121900-A1Priority Date:2023-12-05
- Oxy-fluoropiperidine derivative as kinase inhibitorPublication Number:EP-3733673-A1Priority Date:2017-12-28
- Oxy-fluoropiperidine Derivative as Kinase InhibitorPublication Number:US-2020308177-A1Priority Date:2017-12-28
- Oxy-fluoropiperidine compounds as kinase inhibitors, pharmaceutical composition comprising the same and their use in the prevention or treatment of inflammatory diseases, autoimmune diseases, proliferative diseases or hyperproliferative diseases and immune-mediated diseases, cancers, tumorsPublication Number:BR-112020013141-B1Priority Date:2017-12-28
- Substituted piperidines as kinase inhibitorsPublication Number:US-11339167-B2Priority Date:2017-12-28Grant Date:2022-05-24
- Oxy-haloperidine derivatives as kinase inhibitorsPublication Number:CN-111527091-APriority Date:2017-12-28
- Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:KR-102318929-B1Priority Date:2017-12-28Grant Date:2021-10-28
- Oxy-fluoropiperidine derivative as a kinase inhibitorPublication Number:JP-6995428-B2Priority Date:2017-12-28Grant Date:2022-01-14
- Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:CA-3084962-A1Priority Date:2017-12-28
- Oxy-fluoropiperidine derivative as a kinase inhibitorPublication Number:ES-2922633-T3Priority Date:2017-12-28Grant Date:2022-09-19
- Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:KR-20190080803-APriority Date:2017-12-28
- Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:CA-3084962-CPriority Date:2017-12-28Grant Date:2022-08-09
- Oxy-fluoropiperidine derivative as kinase inhibitorPublication Number:EP-3733673-B1Priority Date:2017-12-28Grant Date:2022-06-29
- Oxy-haloperidine derivatives as kinase inhibitorsPublication Number:CN-111527091-BPriority Date:2017-12-28Grant Date:2023-03-28
- Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:KR-20210062618-APriority Date:2017-12-28
- Oxy-fluoropiperidine derivatives as kinase inhibitorPublication Number:KR-102592083-B1Priority Date:2017-12-28Grant Date:2023-10-20
- OXY-FLUOROPIPERIDINE DERIVATIVE AS A KINASE INHIBITORPublication Number:HR-P20221043-T1Priority Date:2017-12-28
- Oxy-fluoropiperidine derivative as kinase inhibitorPublication Number:IL-275207-BPriority Date:2017-12-28
/////////anax labs, plodicitinib, Janus tyrosine kinase 3/TEC family kinase inhibitor, antiinflammatory, veterinary, SX5UEP3JXA
Peturadol
Peturadol
CAS 686301-48-4
MFC12H20N6O MW264.33 g/mol
5-{[2-(6-amino-9H-purin-9-yl)ethyl]amino}pentan-1-ol
central analgesic, NB001, NB 001, HTS 09836, J89QT81NBQ
NB-001 has been investigated for the treatment of Recurrent Herpes Labialis.
NB001 (HTS 09836) is an adenylcyclase 1 (AC1) inhibitor which has effect on neural and non-neural pain by modulating AC1 activity
Peturadol (also known by its developmental code NB001) is a potent, selective, and orally active adenylyl cyclase 1 (AC1) inhibitor. It is primarily recognized as a specialized chemical compound used in advanced medical and pharmacological laboratory research.
Because drug names can sometimes look or sound very similar, please check the spelling carefully. If you are looking for a medication prescribed to you by a doctor, it is highly likely you mean Patradol (a combination painkiller containing tramadol and paracetamol) or Pentadol / Tapentadol (an opioid analgesic).
Clinical Trial
| NCT Number | Sponsor | Condition | Start Date | Phase |
|---|---|---|---|---|
| NCT01324466 | NanoBio Corporation | Recurrent Herpes Labialis | 2011-04 | PHASE3 |
| NCT05290493 | Nobias Therapeutics, Inc. | 22q11 Deletion Syndrome | 2022-02-10 | PHASE2 |
| NCT01695187 | NanoBio Corporation | Herpes Labialis | 2012-10 | PHASE3 |
| NCT01321359 | NanoBio Corporation | Recurrent Herpes Simplex Labialis | 2011-04 | PHASE3 |
| NCT00453401 | NanoBio Corporation | Herpes Labialis | 2007-02 | PHASE2 |
- NB-001 in Children and Adolescents With 22q11 Deletion SyndromeCTID:NCT05290493Phase:Phase 2Status:CompletedDate:2025-02-10
- NB-001 Treatment of Recurrent Herpes LabialisCTID:NCT01695187Phase:Phase 3Status:Unknown statusDate:2013-06-14
- A Multicenter Study of NB-001 in the Treatment of Recurrent Herpes Labialis (SHaRCS)CTID:NCT01324466Phase:Phase 3Status:CompletedDate:2013-05-23
- Safety, Pharmacokinetics, and Efficacy Study of NB-001 to Treat Recurrent Herpes LabialisCTID:NCT00453401Phase:Phase 2Status:CompletedDate:2008-05-30
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2007041863&_cid=P22-MSFGZW-54602-1
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=US210409779&_cid=P22-MSFGZW-54602-1
Synthesis and Purification of Intermediate 2
(2) Synthesis and Purification of NB001
PAT
- Method for treating neuronal and non-neuronal painPublication Number:CA-2625553-CPriority Date:2005-10-14Grant Date:2014-03-11
- Method for treating neuronal and non-neuronal painPublication Number:WO-2007041863-A1Priority Date:2005-10-14
- Methods for treating herpes virus infectionsPublication Number:CA-2721510-A1Priority Date:2008-04-18
- Method for treating neuronal and non-neuronal painPublication Number:EP-1948182-B1Priority Date:2005-10-14Grant Date:2012-12-12
- Method for Treating Neuronal and Non-Neuronal PainPublication Number:US-2009233922-A1Priority Date:2005-10-14
- Method for treating neuronal and non-neuronal painPublication Number:CA-2625553-A1Priority Date:2005-10-14
- Methods for treating neural and non-neuralgiaPublication Number:JP-5404045-B2Priority Date:2005-10-14Grant Date:2014-01-29
- Neuronal stem cell differentiationPublication Number:WO-2015055987-A1Priority Date:2013-10-14
- Phosphodiesterase Inhibitor TreatmentPublication Number:US-2024108627-A1Priority Date:2013-03-15
- Phosphodiesterase Inhibitor TreatmentPublication Number:US-2022226332-A1Priority Date:2013-03-15
- Process for preparing an enantiomerically enriched, deuterated secondary alcohol from a corresponding ketone without reducing deuterium incorporationPublication Number:US-9074233-B2Priority Date:2010-09-01Grant Date:2015-07-07
- Methods for treating herpes virus infectionsPublication Number:US-2010075914-A1Priority Date:2008-04-18
- Anti-hsv pre-exposure prophylaxisPublication Number:EP-3166680-B1Priority Date:2014-07-07Grant Date:2023-11-15
- Viral prophylaxis treatment methods and pre-exposure prophylaxis kitsPublication Number:EP-4342545-A2Priority Date:2014-07-07
- Neuronal stem cell differentiationPublication Number:EP-3058064-A1Priority Date:2013-10-14
- neuronal stem cell differentiationPublication Number:CN-105658787-APriority Date:2013-10-14
- Neuronal stem cell differentiationPublication Number:US-2016257930-A1Priority Date:2013-10-14
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References
[1]. Min Zhuo. Method for treating neuronal and non-neuronal pain. US8124599B2.
[2]. Wang H, et al., Identification of an adenylyl cyclase inhibitor for treating neuropathic and inflammatory pain. Sci Transl Med. 2011 Jan 12;3(65):65ra3. [Content Brief]
[3]. Zhou Z, et al., Inhibition of calcium-stimulated adenylyl cyclase subtype 1 (AC1) for the treatment of pain and anxiety symptoms in Parkinson’s disease mice model. Mol Pain. 2024 Jan-Dec;20:17448069241266683. [Content Brief]
////////////peturadol, anax labs, central analgesic, NB001, NB 001, HTS 09836, J89QT81NBQ
Petadeferitrin
Petadeferitrin
CAS911714-45-9
MFC16H21NO6S MW355.4 g/mol
(4S)-2-[2-hydroxy-4-[2-(2-methoxyethoxy)ethoxy]phenyl]-4-methyl-5H-1,3-thiazole-4-carboxylic acid
- (4S)-4,5-Dihydro-2-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)phenyl)-4-methyl-4-thiazolecarboxylic acid
- 4-Thiazolecarboxylic acid, 4,5-dihydro-2-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)phenyl)-4-methyl-, (4S)-
- (4S)-4,5-dihydro-2-[2-hydroxy-4-[2-(2-methoxyethoxy)ethoxy]phenyl]-4-methyl-4-thiazolecarboxylic acid
(4S)-2-{2-hydroxy-4-[2-(2-methoxyethoxy)ethoxy]phenyl}-4-methyl4,5-dihydro-1,3-thiazole-4-carboxylic acid
iron chelating agent, SP 420, WBX54NZ436
Petadeferitrin is an orally bioavailable iron-chelating agent and derivative of desferrithiocin, with iron chelating and protective activities in diseases of iron overload. Upon oral administration, petadeferitrin targets, binds to and chelates free iron. This induces the excretion of iron, prevents iron accumulation and prevents cellular and/or tissue damage associated with iron overload.
Petadeferitrin (formerly known as SP-420) is an investigational, orally bioavailable, small-molecule iron chelator being developed by Pharmacosmos (and its subsidiary Abfero Pharmaceuticals) to treat patients with transfusion-dependent iron overload. The drug works by binding to excess free iron in the body and forming complexes that are primarily excreted through bile and feces.
Key Characteristics & Mechanisms
- Drug Class: It is a tridentate iron chelator and a derivative of desferrithiocin.
- Enhanced Efficiency: In preclinical studies, it demonstrated a higher iron clearance efficiency (ICE value of 26.7) compared to desferrithiocin.
- Brain-Penetrant: It is uniquely characterized as a brain-penetrant agent, which could expand its potential protective use in specific diseases associated with iron accumulation.
Clinical Development Status
- Investigational Status: The drug remains investigational and has not yet been approved for commercial use anywhere in the world.
- Target Diseases: Clinical evaluation focuses on individuals who suffer from iron overload due to frequent blood transfusions, such as patients with β-thalassemia and sickle cell disease.
- Ongoing Studies: Pharmacosmos is actively evaluating the drug in Phase II clinical trials (such as ClinicalTrials.gov ID NCT05693909) to assess its safety, tolerability, and dosing advantages over existing options. Early human data suggests it may offer effective clearance with less frequent dosing compared to some currently approved alternatives.
- A Trial Testing SP-420 in Subjects With Transfusion-dependent β-thalassemia or Low-risk Myelodysplastic SyndromesCTID:NCT05693909Phase:Phase 2Status:RecruitingDate:2025-09-24
- Safety of SP-420 in the Treatment of Transfusional Iron OverloadCTID:NCT04741542Phase:Phase 1Status:TerminatedDate:2024-12-27
- SP-420 in Subjects With Transfusion-dependent Beta-Thalassemia or Other Rare AnemiasCTID:NCT03801889Phase:Phase 2Status:WithdrawnDate:2020-10-05
- Safety and Pharmacokinetic Study of Escalating Doses of SP-420, an Iron Chelator, in Patients With β-ThalassemiaCTID:NCT02274233Phase:Phase 1Status:TerminatedDate:2015-09-29
An open-label, dose-escalation, dose-finding, and proof-of-concept trial of SP-420 in subjects with transfusion-dependent β-thalassemiaEudraCT:2022-002395-36
Phase:Phase 2, Status:Trial now transitioned, Date:2022-12-16
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=US42268401&_cid=P21-MSCM3W-69668-1
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2006107626&_cid=P21-MSCM3W-69668-1
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=US43268075&_cid=P21-MSCM3W-69668-1
PAT
Desferrithiocin polyether analoguesPublication Number:
US-2017217912-A1Priority Date:
2005-04-04
- Deferithiocin polyether analoguePublication Number:JP-6178816-B2Priority Date:2005-04-04Grant Date:2017-08-09
- Deferithiocin polyether analoguePublication Number:JP-2008536833-APriority Date:2005-04-04
- Desferrithiocin polyether analoguesPublication Number:EP-3190106-A1Priority Date:2005-04-04
- Desferrithiocin polyether analoguesPublication Number:US-9567309-B2Priority Date:2005-04-04Grant Date:2017-02-14
- Desferrithiocin polyether analoguesPublication Number:US-2013030028-A1Priority Date:2005-04-04
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References
- Target Class Profiling of Small-Molecule MethyltransferasesPublication Name:ACS Chemical BiologyPublication Date:2023-03-28PMCID:PMC10983791PMID:36976909DOI:10.1021/acschembio.3c00124
- Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitorsPublication Name:Proceedings of the National Academy of Sciences of the United States of AmericaPublication Date:2020-11-23PMCID:PMC7733812PMID:33229545DOI:10.1073/pnas.2005463117
- Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput ScreeningPublication Name:SLAS discovery : advancing life sciences R & DPublication Date:2020-01PMCID:PMC10791069PMID:31498718DOI:10.1177/2472555219873068
- A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoproteinPublication Name:Molecular PharmacologyPublication Date:2019-11PMCID:PMC6790066PMID:31515284DOI:10.1124/mol.119.115964
- Safety and pharmacokinetics of the oral iron chelator SP‐420 in β‐thalassemiaPublication Name:American Journal of HematologyPublication Date:2017-10-31PMID:28940308DOI:10.1002/ajh.24914
- Metabolically programmed iron chelatorsPublication Name:Bioorganic & Medicinal ChemistryPublication Date:2015-09-01PMCID:PMC4608554PMID:26231739DOI:10.1016/j.bmc.2015.06.059
- Substituent Effects on Desferrithiocin and Desferrithiocin Analogue Iron-Clearing and Toxicity ProfilesPublication Name:Journal of Medicinal ChemistryPublication Date:2012-08-13PMCID:PMC3583384PMID:22889170DOI:10.1021/jm300509y
- CCDC 757291: Experimental Crystal Structure DeterminationPublication Date:2011DOI:10.5517/cctf0rz
- The Impact of Polyether Chain Length on the Iron Clearing Efficiency and Physiochemical Properties of Desferrithiocin AnaloguesPublication Name:Journal of Medicinal ChemistryPublication Date:2010-04-08PMCID:PMC2951135PMID:20232803DOI:10.1021/jm9018146
/////////petadeferitrin, ANAX LABS, iron chelating agent, SP 420, WBX54NZ436
Perzebertinib, Bizrolertinib
Perzebertinib, Bizrolertinib
CAS 2414056-31-6
MFC27H26F2N8O3 MW548.5 g/mol
5-[(4R)-3,3-difluoro-1-methylpiperidin-4-yl]oxy-6-methoxy-N-[3-methyl-4-([1,2,4]triazolo[1,5-c]pyrimidin-7-yloxy)phenyl]quinazolin-4-amine
- 4-Quinazolinamine, 5-[[(4R)-3,3-difluoro-1-methyl-4-piperidinyl]oxy]-6-methoxy-N-[3-methyl-4-([1,2,4]triazolo[1,5-c]pyrimidin-7-yloxy)phenyl]-
- 5-[[(4R)-3,3-Difluoro-1-methyl-4-piperidinyl]oxy]-6-methoxy-N-[3-methyl-4-([1,2,4]triazolo[1,5-c]pyrimidin-7-yloxy)phenyl]-4-quinazolinamine
5-{[(4R)-3,3-difluoro-1-methylpiperidin-4-yl]oxy}-6-methoxy-N-{3-methyl-4-[([1,2,4]triazolo[1,5-c]pyrimidin-7-yl)oxy]phenyl}quinazolin4-amine
epidermal growth factor receptor tyrosine kinase inhibitor, antineoplastic, ZN-A-1041, ZN 1041, RG 6596, Bizrolertinib, UN8TM5120C
Perzebertinib (also known as bizrolertinib or by developmental codes ZN-A-1041, ZN-1041, and RG6596) is an orally active, potent, and highly selective HER2 (ERBB2) tyrosine kinase inhibitor (TKI) designed to treat advanced solid tumors, primarily HER2-positive breast cancer.
Mechanism of Action
Perzebertinib functions as a selective, irreversible inhibitor of the HER2 tyrosine kinase. It blocks the ATP-binding site of the receptor to stop autophosphorylation. This action shuts down downstream signaling via the PI3K/AKT and MAPK pathways, successfully suppressing the growth, survival, and migration of tumor cells overexpressing HER2.
Key Clinical Advantages
- Blood-Brain Barrier (BBB) Penetration: The drug is designed to cross the blood-brain barrier effectively. This makes it highly valuable for treating brain metastases, a common and aggressive complication in advanced HER2-positive breast cancers.
- EGFR Sparing: Unlike older pan-EGFR/HER2 inhibitors, perzebertinib is engineered to spare wild-type EGFR. Sparing EGFR helps minimise common on-target side effects like severe skin rash and diarrhea.
- Efflux Resistance: It is not a substrate for P-gp or BCRP efflux pumps, allowing it to maintain high concentrations within central nervous system (CNS) tissues.
Development and Clinical Status
Initially discovered and developed by Suzhou Zanrong Pharmaceutical Technology (Zion Pharma), the asset is being co-developed in partnership with Roche and Genentech.
The drug has progressed through Phase 1 clinical studies evaluating its safety and pharmacokinetics in advanced solid tumors, moving forward into Phase 2/3 evaluations for HER2-positive advanced or locally advanced metastatic breast cancer. It is frequently evaluated as a monotherapy or in combination regimens alongside established therapies like capecitabine, trastuzumab, or pertuzumab
PAT
US11723908, Example 37, EG 77
https://patentscope.wipo.int/search/en/detail.jsf?docId=US344952565&_cid=P10-MS9QYW-06569-1
PAT
International Patent Publication No. WO 2020/057511 A1, which is incorporated herein by reference in its entirety, discloses quinazoline compounds that inhibit type I receptor tyrosine kinases, demonstrate good brain penetration in animals, and possess favorable toxicity profiles (for example a decreased activity against hERG), and thus particularly useful in the treatment of type I receptor tyrosine kinases mediated diseases or conditions, in particular ErbB2-associated disease or conditions, including cancer (e.g., metastatic cancer, such as brain metastases). A specific compound, which is identified as (R)-N-(4-([1,2,4]triazolo[1,5-c]pyrimidin-7-yloxy)-3-methylphenyl)-5-((3,3-difluoro-1-methylpiperidin-4-yl)oxy)-6-methoxyquinazolin-4-amine (also referred to as compound (I) herein),
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020057511&_cid=P10-MS9R3W-09545-1
[0681]
(S) -N- (4- ( [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yloxy) -3-methylphenyl) -5- ( (3, 3-difluoro-1-methylpiperidin-4-yl) oxy) -6-methoxyquinazolin-4-amine
Step 5: (R) -N- (4- ( [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yloxy) -3-methylphenyl) -5- ( (3, 3-difluoro-1-methylpiperidin-4-yl) oxy) -6-methoxyquinazolin-4-amine and
[0696]
(S) -N- (4- ( [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yloxy) -3-methylphenyl) -5- ( (3, 3-difluoro-1-methylpiperidin-4-yl) oxy) -6-methoxyquinazolin-4-amine
[0697]
[0698]
To a solution of 4-chloro-5- ( (3, 3-difluoro-1-methylpiperidin-4-yl) oxy) -6-methoxyquinazoline (410 mg, 1.19 mmol) in Propan-2-ol (60 mL) was added TsOH. H 2O (68 mg, 0.36 mmol) and 4- ( [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yloxy) -3-methylaniline (259 mg, 1.07 mmol) . The resulting mixture was stirred at 100℃ under Ar 2protection and concentrated. The residue was dissolved in H 2O (100 mL) , basified with aq. NaHCO 3to pH =7-8, extracted with DCM: MeOH = 20: 1 (100 mLx3) . The combined organic layers were dried over anhydrous Na 2SO 4, filtered and concentrated. The residue was purified by column chromatography (DCM/MeOH=30/1) to give product (300 mg, 46%yield) as white solid. The racemic material was subsequently separated by chiral SFC to give two isomers:
[0699]
(R) -N- (4- ( [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yloxy) -3-methylphenyl) -5- ( (3, 3-difluoro-1-methylpiperidin-4-yl) oxy) -6-methoxyquinazolin-4-amine (Peak 1, retention time 6.241 min, ee: >99%) (100 mg, 67%) as a white solid. MS (ESI) m/z: 549.2 (M+H) +. 1H NMR (400 MHz, CDCl 3) δ 10.04 (s, 1H) , 9.20 (s, 1H) , 8.61 (s, 1H) , 8.33 (s, 1H) , 7.88 (d, J = 2.0 Hz, 1H) , 7.79-7.76 (m, 1H) 7.69 (d, J = 9.2 Hz, 1H) , 7.53 (d, J = 9.2 Hz, 1H) , 7.11 (d, J = 8.8 Hz, 1H) , 6.90 (s, 1H) , 4.84-4.79 (m, 1H) , 4.03 (s, 3H) , 3.22-3.21 (m, 1H) , 2.93 (d, J = 7.2 Hz, 1H) , 2.38 (s, 3H) , 2.41-2.34 (m, 1H) , 2.34-2.27 (m, 1H) , 2.19 (s, 3H) , 2.16-2.10 (m, 2H) .
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References
- Quinazoline derivatives as antitumor agentsPublication Number:US-2023293533-A1Priority Date:2018-09-18
- Quinazoline derivatives as antitumor agentsPublication Number:ES-2971927-T3Priority Date:2018-09-18Grant Date:2024-06-10
- Quinazoline derivatives as antitumor agentsPublication Number:EP-4360713-B1Priority Date:2018-09-18Grant Date:2024-10-30
- Quinazoline derivatives as antitumor agentsPublication Number:ES-3007082-T3Priority Date:2018-09-18Grant Date:2025-03-19
- Quinazoline derivatives as antitumor agentsPublication Number:EP-4360713-A2Priority Date:2018-09-18
- Quinazoline derivatives as antitumor agentsPublication Number:EP-3853220-B1Priority Date:2018-09-18Grant Date:2024-01-03
- Quinazoline derivatives as antitumor agentsPublication Number:EP-3853220-A1Priority Date:2018-09-18
- Quinazoline derivatives as antitumor agentsPublication Number:US-2021386742-A1Priority Date:2018-09-18
- Quinazoline derivatives as antitumor agentsPublication Number:US-11723908-B2Priority Date:2018-09-18Grant Date:2023-08-15
- Crystalline forms of quinazoline derivatives, preparation, compositions and uses thereofPublication Number:CN-120623183-APriority Date:2021-10-20
- Crystalline forms of quinazoline derivatives, preparation, compositions and uses thereofPublication Number:CN-120309621-APriority Date:2021-10-20
- Quinazoline derivatives as antitumor agentsPublication Number:WO-2020057511-A1Priority Date:2018-09-18
- Quinazoline Derivatives as Antitumor AgentsPublication Number:JP-7546550-B2Priority Date:2018-09-18Grant Date:2024-09-06
- Quinazoline derivatives as antitumor agentsPublication Number:CA-3099776-A1Priority Date:2018-09-18
/////////perzebertinib, anax labs, epidermal growth factor receptor tyrosine kinase inhibitor, antineoplastic, ZN-A-1041, ZN 1041, RG 6596, Bizrolertinib, UN8TM5120C
Pasodacigib
Pasodacigib
Cas 2648721-77-9
MFC24H23FN4O3 mw 434.5 g/mol
6-fluoro-1-methyl-4-[4-(5-methyl-1,3-benzoxazol-2-yl)piperidin-1-yl]-2-oxo-1,2-dihydroquinoline-3-carboxamide
6-fluoro-1-methyl-4-[4-(5-methyl-1,3-benzoxazol-2-yl)piperidin-1-yl]-2-oxo-1,2-dihydroquinoline-3-carboxamide
diacylglycerol kinase inhibitor, antineoplastic, BAY 2862789, BAY-2862789, XM6U88YE6H
Pasodacigib (also known by its developmental code BAY 2862789 or BAY-2862789) is an investigational small-molecule drug developed by Bayer AG. It functions as a potent and selective diacylglycerol kinase alpha (DGKα) inhibitor designed for cancer immunotherapy.
🧪 Mechanism of Action
- Targeting DGKα: Diacylglycerol kinase alpha (DGKα) is an enzyme that converts diacylglycerol (DAG) into phosphatidic acid (PA) within cells.
- T-Cell Reactivation: In the tumor microenvironment, overactive DGKα metabolises DAG, which depletes the signaling required for T-cell activation. By blocking this enzyme, pasodacigib aims to restore DAG levels, reactivating the patient’s own T-cells to mount a clinically beneficial anti-tumor immune response.
📋 Key Details & Chemical Properties
- Developer: Bayer AG
- CAS Registry Number: 2648721-77-9
- Molecular Formula: C₂₄H₂₃FN₄O₃
- Molecular Weight: 434.46 g/mol
- Research Status: It is an investigational drug that has entered clinical trial assessment (such as the Bayer-led study NCT05858164) to evaluate its safety and efficacy in treating advanced malignancies.
⚠️ Important Medical Disclaimer
Pasodacigib is strictly an investigational compound undergoing clinical development and laboratory research. It is not approved by the FDA or any other global regulatory authority for prescription, public medical use, or patient purchase.
If you are looking into this molecule for scientific research or a clinical study, please let me know if you need specific details regarding its chemical structure, information on related DGK inhibitors, or updates on active oncology clinical trials
Pat
https://patentscope.wipo.int/search/en/detail.jsf?docId=US400268899&_cid=P22-MS6W4B-66581-1
Example 298
6-fluoro-1-methyl-4-[4-(5-methyl-1,3-benzoxazol-2-yl)piperidin-1-yl]-2-oxo-1,2-dihydroquinoline-3-carboxamide
| 1H NMR (400 MHz, DMSO-d 6) δ ppm 2.02-2.15 (m, 2H) 2.17-2.26 (m, 2H) 2.44 (s, 3H) 3.13-3.25 (m, 3H) 3.35-3.43 (m, 2H) 3.59 (s, 3H) 7.18 (d, 1H) 7.47-7.63 (m, 6H) 7.73 (br s, 1H). |
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021105117&_cid=P22-MS6W2Y-65422-1
Intermediate 101
6-fluoro-1-methyl-2H-3,1-benzoxazine-2,4(1 H)-dione
To a solution of 5.00 g 6-fluoro-2H-3,1-benzoxazine-2,4(1 H)-dione (26.8 mmol, CAS 321-69-7) and 9.3 ml. N,N-diisopropylethylamine (54 mmol) in 40 ml. dimethylformamide was added 5.1 ml. iodomethane (80 mmol) at rt and the mixture was stirred overnight. The reaction mixture was diluted with 1000 ml. water and the resulting solid was collected by filtration, the filter cake was washed with water and dried in vacuum to give 4.93 g of the title compound (99 % purity, 93 % yield).
1H NMR (400 MHz, DMSO-cfe) d ppm 3.47 (s, 3H), 7.40-7.61 (m, 1 H), 7.69-7.93 (m, 2H).Intermediate 102
6-fluoro-4-hydroxy-1-methyl-2-oxo-1 ,2-dihydroquinoline-3-carbonitrile
4.85 g 6-fluoro-1 -methyl-2H-3,1 -benzoxazine-2,4(1 H)-dione (intermediate 101 , 24.6 mmol,) was solubilised in 50 ml. tetrahydrofurane, 34 ml. triethylamine (250 mmol) and then 15.1 ml. ethyl cyanoacetate (133 mmol) were added carefully and the suspension was stirred 72 h at 900. The reaction mixture was cooled down to rt, concentrated under reduced pressure, the residue was diluted with water and ethyl acetate (1 :1) and the mixture was adjusted to pH = 1 with hydrogen chloride solution (2 M in water). The resulting solid was filtered and the filter cake was washed with less water and ethyl acetate to give 4.40 g of the title compound (100 % purity, 82 % yield).
1H NMR (400 MHz, DMSO-cfe) d ppm 3.34 (br s, 3H), 7.01 -7.44 (m, 2H), 7.51 -7.70 (m, 1 H).
Intermediate 103
4-chloro-6-fluoro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile
A mixture of 4.40 g 6-fluoro-4-hydroxy-1-methyl-2-oxo-1 ,2-dihydroquinoline-3-carbonitrile (intermediate 102, 20.0 mmol) and 19 ml. phosphoric trichloride (200 mmol) was stirred overnight at 900. The reaction mixture was cooled down to rt, diluted with hexane and the resulting solid was filtered. The filter cake was carefully added to a half saturated solution of sodium bicarbonate, the resulting suspension was filtered, the solid was washed with water, ethyl acetate and then with ethanol and dried in vacuum to give 4.17 g of the title compound (100 % purity, 88 % yield).
1H NMR (400 MHz, DMSO-cfe) d ppm 3.67 (s, 3H); 7.58 – 8.09 (m, 3H).
Example 217
6-fluoro-1-methyl-4-[4-(5-methyl-1,3-benzoxazol-2-yl)pipendin-1-yl]-2-oxo-1,2-dihydroquinoline-3-carbonitrile
80 mg 4-chloro-6-fluoro-1-methyl-2-oxo-1 ,2-dihydroquinoline-3-carbonitrile (338 pmol, intermediate 103) was suspended in 2.5 ml. 2-propanol, 180 mI_ N,N-diisopropylethylamine (1.0 mmol) and 87.7 mg 5-methyl-2-(piperidin-4-yl)-1 ,3-benzoxazole (406 pmol, CAS 199292-77-8) were added and the mixture was stirred for 2 h at 900. The reaction mixture was cooled down to rt and the suspension was diluted with water and stirred for 15 min. The solid was filtered off and washed with water and ethanol to give 127 mg of the title compound (98 % purity, 88 % yield).
1H NMR (400 MHz, DMSO-cfe) d ppm 2.07 – 2.19 (m, 2 H) 2.27 – 2.35 (m, 2 H) 2.44 (s, 3 H) 3.43 (tt, 1 H) 3.55 – 3.64 (m, 5 H) 3.81 (br d, 2 H) 7.18 (dd, 1 H) 7.53 (d, 1 H) 7.54 – 7.61 (m, 2 H) 7.61 – 7.70 (m, 2 H).
LC-MS (Method 2): R, = 1.32 min; MS (ESIpos): m/z = 417.4 [M+H]+
Example 298
6-fluoro-1-methyl-4-[4-(5-methyl-1,3-benzoxazol-2-yl)pipendin-1-yl]-2-oxo-1,2-dihydroquinoline-3-carboxamide
68 mg 6-fluoro-1 -methyl-4-[4-(5-methyl-1 ,3-benzoxazol-2-yl)piperidin-1-yl]-2-oxo-1 ,2-dihydroquinoline-3-carbonitrile (160 pmol, example 217), 9 mg palladium(ll)acetate (40 pmol) and 142 mg acetaldoxime (2.4 mmol) were stirred in 1 .5 ml. ethanol for 5 h at 80TT The reaction mixture was diluted with water, extracted with ethyl acetate two times, the combined organic layers were filtered through a waterresistant filter and the filtrate was concentrated under reduced pressure. The residue was purified by RP-HPLC (column: X-Bridge C18 5pm 100x30mm, mobile phase: acetonitrile / water (0.2 vol. % ammonia 32 %)-gradient) to give 41 .4 mg of the title compound (100 % purity, 60 % yield).
1H NMR (400 MHz, DMSO-cfe) d ppm 2.02 – 2.15 (m, 2 H) 2.17 – 2.26 (m, 2 H) 2.44 (s, 3 H) 3.13 – 3.25 (m, 3 H) 3.35 – 3.43 (m, 2 H) 3.59 (s, 3 H) 7.18 (d, 1 H) 7.47 – 7.63 (m, 6 H) 7.73 (br s, 1 H).
LC-MS (Method 2): R, = 1 .17 min; MS (ESIpos): m/z = 435.4 [M+H]
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References
- DGK alpha inhibitors as immune activation substituted aminoquinolones of (2)Publication Number:CN-119523983-APriority Date:2019-11-28
- Cyclopropyl modulators of p2y12 receptorPublication Number:US-2017002015-A1Priority Date:2009-07-27
- Substituted aminoquinolones as dgkalpha inhibitors for immune activationPublication Number:EP-4065574-A1Priority Date:2019-11-28
- Substituted aminoquinolones as dgkalpha inhibitors for immune activationPublication Number:WO-2021105117-A1Priority Date:2019-11-28
- Substituted aminoquinolones as immunoactive DGK alpha inhibitorsPublication Number:CN-115003665-APriority Date:2019-11-28
- Substituted aminoquinolones as inhibitors of immune-activated DGKαPublication Number:CN-119564686-APriority Date:2019-11-28
- DGK alpha inhibitors as immune activation substituted aminoquinolones of (2)Publication Number:CN-119424429-APriority Date:2019-11-28
- Combinations of dgk (diacylglycerol kinase) inhibitors and immune checkpoint inhibitors and modulatorsPublication Number:TW-202448461-APriority Date:2023-02-06
- Substituted aminoquinolones as DGKalpha inhibitors for immune activationPublication Number:US-11998539-B2Priority Date:2019-11-28Grant Date:2024-06-04
- Substituted aminoquinolones as dgkalpha inhibitors for immune activationPublication Number:US-2023148194-A1Priority Date:2019-11-28
- Substituted aminoquinolones as dgkalpha inhibitors for immune activationPublication Number:US-2023201186-A1Priority Date:2019-11-28
- DGK alpha inhibitors as immune activation substituted aminoquinolones of (2)Publication Number:CN-115003665-BPriority Date:2019-11-28Grant Date:2024-11-08
- Combination of ccr8 antibodies with dgk inhibitors in the treatment of cancerPublication Number:WO-2024165468-A1Priority Date:2023-02-06
- Combination of ccr8 antibodies with dgk inhibitorsPublication Number:TW-202436351-APriority Date:2023-02-06
- Combinations of dgk (diacylglycerol kinase) inhibitorsPublication Number:WO-2024165470-A1Priority Date:2023-02-06
- Combinations of dgk (diacylglycerol kinase) inhibitors and immune checkpoint inhibitors and modulatorsPublication Number:WO-2024165469-A1Priority Date:2023-02-06
- Combinations of dgk (diacylglycerol kinase) inhibitorsPublication Number:TW-202448460-APriority Date:2023-02-06
/////////pasodacigib, anax labs, diacylglycerol kinase inhibitor, antineoplastic, BAY 2862789, BAY-2862789, XM6U88YE6H
DR ANTHONY MELVIN CRASTO
ORGANIC SPECTROSCOPY
New Drug Approvals 
