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Imofinostat
Imofinostat
CAS 1338320-94-7
MF C17H16N2O4S MW 344.4 g/mol
- 3-(1-(Benzenesulfonyl)-2,3-dihydro-1H-indol-5-yl)-N-hydroxyacrylamide
- (E)-3-[1-(benzenesulfonyl)-2,3-dihydroindol-5-yl]-N-hydroxyprop-2-enamide
(2E)-3-[1-(benzenesulfonyl)-2,3-dihydro-1H-indol-5-yl]-N-hydroxyprop2-enamide
histone deacetylase inhibitor, antineoplastic, ABT-301, MPT0E028, ABT 301, MPT0E 028, T65L58FI65
Imofinostat (also known as ABT-301 or MPT0E028) is an orally bioavailable, small-molecule histone deacetylase (HDAC) inhibitor primarily being developed as an innovative precision oncology treatment. Developed by companies like AnBogen Therapeutics and Formosa Pharmaceuticals, it is designed to reactivate tumor suppressor genes that cancer cells have silenced, thereby triggering cancer cell death (apoptosis) and stopping tumor growth.
Mechanism of Action
Imofinostat works through a distinct multi-modality approach to fight cancer cells:
- HDAC Inhibition: It acts as a potent inhibitor of human pan-histone deacetylase enzymes, showing preferential selectivity for Class I HDACs (especially HDAC3). This blocks the deacetylation of histone proteins, causing chromatin to remodel and forcing cancer cells to express tumor-suppressor genes.
- Akt Pathway Targeting: Independent of its epigenetic effects, it can directly target and reduce the activation (phosphorylation) of the Akt protein kinase, a major pathway that cancer cells use to survive and multiply.
- Microenvironment Modulation: Preclinical data shows it alters the tumor microenvironment by converting “cold tumors” (invisible to the immune system) into “hot tumors” by promoting the infiltration of CD8+ cytotoxic T cells.
Current Clinical Status & Indications
Imofinostat is actively moving through clinical trial pipelines, focusing heavily on combination therapies to overcome treatment resistance:
- Colorectal Cancer (CRC): It is currently being evaluated in a global Phase 1/2 clinical trial (NCT07244705). It is combined with the immune checkpoint inhibitor tislelizumab (Tevimbra®) and the anti-angiogenic drug bevacizumab to treat advanced, metastatic colorectal cancer.
- Pancreatic Cancer: Recent data presented at the 2026 American Association for Cancer Research (AACR) Annual Meeting demonstrates that imofinostat disrupts the HDAC3-NRF2 pathway. This action breaks down chemotherapy resistance in highly aggressive KRAS-mutant pancreatic ductal adenocarcinoma, making tumors much more sensitive to treatments like gemcitabine.
- Other Solid Tumors: Phase 1 monotherapy trials have confirmed that the drug possesses a highly competitive safety profile across a broad variety of advanced solid tumors.
Imofinostat is an orally bioavailable N-hydroxyacrylamide-derived inhibitor of both human pan-histone deacetylase (HDAC) enzymes and the serine/threonine protein kinase Akt (protein kinase B), with potential antineoplastic activity. Upon administration, imofinostat selectively binds to and inhibits HDACs, which inhibits deacetylation of histone proteins and leads to the accumulation of highly acetylated histones. This may result in both an induction of chromatin remodeling, and the selective transcription of tumor suppressor genes. This prevents cell division and induces both cell cycle arrest and apoptosis, which may inhibit the proliferation of susceptible tumor cells. In addition, imofinostat inhibits the phosphorylation and activation of Akt, which prevents the activation of downstream signaling pathways, independent of its HDAC inhibitory activity. HDACs, upregulated in many tumor cell types, are a family of enzymes that deacetylate histone proteins. Akt, overexpressed in many tumor cell types, plays a key role in tumor cell proliferation and survival.
Dose-Seeking Study of MPT0E028 in Subjects With Advanced Solid Malignancies Without Standard Treatment
CTID: NCT02350868
Phase: Phase 1
Status: Completed
Date: 2019-04-11
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2011126821&_cid=P11-MQ4LAI-84972-1
COMD 12
Compound 12 was synthesized via the route as shown in Scheme 3 above (reagents and conditions: (a) NaBH3CN, AcOH; (b) Benzenesulfonyl chloride, 4-methoxybenzenesulfonyl chloride, 3,4-dimethoxybenzenesulfonyl chloride, 4-fluorobenzenesulfonyl chloride, or 4-nitrobenzenesulfonyl chloride, pyridine; (c) L1AIH4, THF; (d) PDC, MS, CH2C12; f) Ph3P = CH-COOCH3, CH2C12; (g) 1M LiOH(aq), dioxane; (h) (i) NH2OTHP, PyBOP, NEt3, DMF; (ii) TFA, MeOH; (i) Fe, NH4C1, Isopropanol, H20).
2,3-Dihydro-lH-indole-5-carboxylic acid methyl ester (10): sodium cyanoborohydride (0.16 g, 2.57 mmol) was added to a solution of methyl indole-5-carboxylate (9) (0.30 g, 1.71 mmol) in AcOH (2 mL) at 0 °C. The reaction mixture was warmed to room temperature and stirred for 2 h before it was quenched with water at 0 °C. Concentrated NaOH was added to reach pH=10. The aqueous layer was extracted with CH2CI2 (15 mL x 3). The combined organic layer was dried over anhydrous MgS04 and concentrated under reduced pressure to give a yellow residue, which was purified by silica gel chromatography (EtOAc: n-hexane = 1 : 2) to afford 10 (0.28 g). 1H NMR (500MHz, CDC13): δ 3.06 (t, J= 8.5 Hz, 2H), 3.65 (t, J= 8.5 Hz, 2H), 3.84 (s, 3H), 6.53-6.55 (m, 1H), 7.75-7.76 (m, 2H).
l-Benzenesulfonyl-2,3-dihydro-lH-indole-5-carboxylic acid methyl ester (11): To a solution of 10 (0.28 g, 1.58 mmol) in pyridine (2 mL), benzenesulfonyl chloride (0.40 ml, 3.16 mmol) was added. The reaction mixture was refluxed overnight. The mixture was then purified by silica gel chromatography (EtOAc: n-hexane = 1 : 3) to afford 11 (0.40 g). 1H NMR (500MHz, CDCI3): δ 2.99 (t, J= 8.6 Hz, 2H), 3.87 (s, 3H), 3.97 (t, J= 8.6 Hz, 2H), 7.45-7.48 (m, 2H), 7.56-7.59 (m, 1H), 7.66 (d, J= 8.5 Hz, 1H), 7.75 (s, 1H), 7.82 (d, J= 7.7 Hz, 2H), 7.90 (d, J= 7.9 Hz, 1H).
(l-Benzenesulfonyl-2,3-dihydro-lH-indol-5-yl)-methanol (12): LAH (0.10 g, 2.52 mmol) was added to a solution of 11 (0.40 g, 1.26 mmol) in THF (10 mL) at 0 °C. The reaction mixture was warmed to room temperature and stirred for 2 h before it was quenched with water and then extracted with CH2CI2 (15 mL x 3). The combined organic layer was dried over anhydrous MgS04 and concentrated under reduced pressure. The reaction mixture was purified by silica gel chromatography (EtOAc: n-hexane = 1 : 1) to afford 12 (0.24 g). 1H NMR (500MHz, CDC13): δ 2.83 (t, J= 8.4 Hz, 2H), 3.92 (t, J= 8.5 Hz, 2H), 4.49 (s, 2H), 7.09 (s, 1H), 7.16 (d, J= 8.2 Hz, 1H), 7.46-7.49 (m, 2H), 7.53 (d, J= 8.2 Hz, 1H), 7.60 (t, J= 7.5 Hz, 1H), 7.76 (d, J= 7.7 Hz, 2H).
l-Benzenesulfonyl-2,3-dihydro-lH-indole-5-carbaldehyde (13): molecular sieves (0.63g) were added to a solution of 12 (0.24 g, 0.83 mmol) in CH2C12 (10 mL), PDC (0.63 g, 1.66 mmol). The mixture was stirred at room temperature overnight before it was filtered through celite. The organic layer was concentrated under reduced pressure then purified by silica gel chromatography (EtOAc: n-hexane = 1 : 2) to afford 13 (0.19 g). 1H NMR (500MHz, CDC13): δ 3.05 (t, J= 8.6 Hz, 2H), 4.01 (t, J= 8.7 Hz, 2H), 7.46-7,49 (m, 2H), 7.58-7.62 (m, 2H), 7.71 (d, J= 8.3 Hz, 1H), 7.75 (d, J= 8.3 Hz, 1H), 7.84 (d, J= 7.8 Hz, 2H), 9.85 (s, 1H).
3-(l-Benzenesulfonyl-2,3-dihydro-lH-indol-5-yl)-acrylic acid methyl ester (14): Methyl (triphenylphosphoranylidene) acetate (0.27 g, 0.79 mmol) was added to a solution of 13 (0.19g,
0.66 mmol) in CH2CI2 (10 mL). The mixture was stirred at room temperature for 3h before it was
quenched with water and then extracted with CH2CI2 (15 mL x 3). The combined organic layer was dried over anhydrous MgS04 and concentrated under reduced pressure to give a yellow residue, which was then purified by silica gel chromatography (EtOAc: n-hexane = 1 : 3) to afford 14
(0.20 g).
3-(l-Benzenesulfonyl-2,3-dihydro-lH-indol-5-yl)-acrylic acid (15): 1M LiOH aqueous solution (1.16 ml, 1.16 mmol) was added to a solution of 14 (0.20g, 0.58 mmol) in dioxane
(15 mL). The reaction mixture was stirred at 40 °C overnight before it was concentrated under reduced pressure. The residue was dissolved in water and concentrated HCl was added up to acidic pH to give the precipitation, which was dried by vacuum to afford 15 (0.16 g). 1H NMR (500MHz, CD3OD): δ 2.92 (t, J= 8.5 Hz, 2H), 3.96 (t, J= 8.5 Hz, 2H), 6.33 (d, J= 15.9 Hz, 1H), 7.38 (s, 1H), 7.41 (d, J= 8.5 Hz, 1H), 7.50-7.53 (m, 2H), 7.55 (d, J= 16.1 Hz, 1H), 7.58-7.64 (m, 2H), 7.82 (d, J = 7.6 Hz, 2H).
3-(l-Benzenesulfonyl-2,3-dihydro-lH-indol-5-yl)-N-hydroxy-acrylamide
(Compound 12): NH2OTHP (0.05 g, 0.44 mmol) was added to a solution of 15 (0.12 g, 0.37 mmol), PyBOP (0.20 g, 0.39 mmol), triethylamine (0.12 ml, 0.88 mmol) in DMF (1.5 mL). The reaction mixture was stirred at room temperature for 1 h before it was quenched with water, followed by extraction with EtOAc (15 mL x 3). The combined organic layer was dried over anhydrous MgS04 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (CH2C12: CH3OH = 30 : 1 : l%NH3(aq)) to give a white solid, which was treated with TFA (1.13 ml, 15.21 mmol) in the presence of CH3OH (25 mL) and stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure to give a white residue, which was recrystallized by CH3OH to afford Compound 12 (0.12 g). 1H NMR (500MHz,
CD3OD): δ 2.91 (t, J= 8.5 Hz, 2H), 3.96 (t, J= 8.4 Hz, 2H), 6.32 (d, J= 15.8 Hz, 1H), 7.32 (s, 1H), 7.37-7.39 (m, 1H), 7.46 (d, J= 15.7 Hz, 1H), 7.50-7.53 (m, 2H), 7.58-7.64 (m, 2H), 7.82 (d, J= 7.8 Hz, 2H). MS (EI) mlz: 170 (100%), 344 (M+, 3.21%). HRMS (EI) for Ci7Hi6N204S (M+): calcd, 344.0831; found, 344.0829.
PAT
US20150368195
https://patentscope.wipo.int/search/en/detail.jsf?docId=US154007904&_cid=P11-MQ4M0P-01888-1
PAT
- Indolyl or indolinyl hydroxamate compoundsPublication Number: US-8846748-B2Priority Date: 2010-03-29Grant Date: 2014-09-30
- Indolyl or indolinyl hydroxamate compoundsPublication Number: US-9598364-B2Priority Date: 2010-03-29Grant Date: 2017-03-21
- Indolyl or indolinyl hydroxamate compoundsPublication Number: WO-2011126821-A2Priority Date: 2010-03-29
- Indolyl or indolinyl hydroxamate compoundsPublication Number: EP-2552887-A2Priority Date: 2010-03-29
- Indolyl or indolinyl hydroxamate compoundsPublication Number: US-2011245315-A1Priority Date: 2010-03-29
- Indolyl or indolinyl hydroxamate compoundsPublication Number: US-2014364477-A1Priority Date: 2010-03-29
- Indolyl or indolinyl hydroxamate compoundsPublication Number: EP-2552887-B1Priority Date: 2010-03-29Grant Date: 2018-10-24
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References
//////////imofinostat, anax labs, histone deacetylase inhibitor, antineoplastic, ABT-301, MPT0E028, ABT 301, MPT0E 028, T65L58FI65
#imofinostat, anax labs, #histone deacetylase inhibitor, #antineoplastic, #ABT-301, #MPT0E028, #ABT 301, #MPT0E 028, #T65L58FI65
Ifupinostat
Ifupinostat
CAS 1235449-52-1
MF C23H25N9O3S MW507.6 g/mol
N-hydroxy-2-[methyl-[[2-[6-(methylamino)-3-pyridinyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]amino]pyrimidine-5-carboxamide
5-Pyrimidinecarboxamide, N-hydroxy-2-(methyl((2-(6-(methylamino)-3-pyridinyl)-4-(4-morpholinyl)thieno(3,2-d)pyrimidin-6-yl)methyl)amino)-
DQ7TD3X4ZJ, BEBT908 FREE BASE,
Ifupinostat (brand name Betlin; formerly known as BEBT-908) is a first-in-class, dual-action cancer medication used to treat specific types of blood cancer. It is developed by the biopharmaceutical company BeBetter Med.
Approved Clinical Use
The drug is conditionally approved in China as a monotherapy for adults with relapsed or refractory diffuse large B-cell lymphoma (r/r DLBCL). It is specifically indicated for patients who have already undergone at least two prior lines of systemic therapy.
Mechanism of Action
Unlike traditional cancer drugs that target a single pathway, ifupinostat is designed to simultaneously disrupt two major cellular mechanisms that drive tumor growth:
- PI3Kα Inhibition: It blocks phosphoinositide 3-kinase alpha (PI3Kα), shutting down the downstream PI3K/AKT/mTOR survival pathway within cancer cells.
- HDAC Inhibition: It blocks histone deacetylase (HDAC) enzymes, leading to epigenetic modifications (such as increased histone-3 acetylation) that trigger cancer cell death.
By hitting both targets at once, the drug suppresses tumor cell proliferation, downregulates the cancer-driving c-Myc protein, and induces cell death via ferroptosis (an iron-dependent form of programmed cell death).
Clinical Research and Future Outlook
- Combinations: Beyond its use as a single agent, ifupinostat is being evaluated in combination with the monoclonal antibody rituximab as a potential second-line treatment for r/r DLBCL. Early phase 1b clinical data presented at ASCO showed a promising 76.2% objective response rate (ORR).
- Brain Penetration: Lab studies indicate that the molecule successfully crosses the blood-brain barrier (BBB), showing therapeutic potential for central nervous system lymphomas.
- Ongoing Verification: Because its initial regulatory green light was given on a conditional basis, a confirmatory randomized phase 3 trial is currently underway to achieve full approval
Ifupinostat is an inhibitor of both phosphoinositide 3-kinase (PI3K) and histone deacetylase (HDAC) enzymes, with potential antineoplastic activity. Upon administration, ifupinostat binds to and inhibits the activity and mediated signaling of both PI3K and HDAC. In addition, ifupinostat may also inhibit other signaling pathways. This may prevent growth of PI3K and/or HDAC-expressing tumor cells.
Ifupinostat (trade name Betlin) is a drug used for the treatment of cancer. It is approved in China for adults with relapsed or refractory diffuse large B-cell lymphoma who have received at least two lines of systemic therapy.[1] It is being developed by BeBetter Med.[2]
Ifupinostat acts as both a phosphoinositide 3-kinase α (PI3Kα) inhibitor and a histone deacetylase (HDAC) inhibitor.[1][3][4]
SYN
- Hydroxamic acid hybrids: Histone deacetylase inhibitors with anticancer therapeutic potencyPublication Name: European Journal of Medicinal ChemistryPublication Date: 2023-12-15PMID: 37875056DOI: 10.1016/j.ejmech.2023.115879
- A Dual PI3K/HDAC Inhibitor Induces Immunogenic Ferroptosis to Potentiate Cancer Immune Checkpoint TherapyPublication Name: Cancer ResearchPublication Date: 2021-12-15PMID: 34711611DOI: 10.1158/0008-5472.can-21-1547
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2024086894&_cid=P21-MQ35ZX-16907-1
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2024086894&_cid=P21-MQ35ZX-16907-1
PAT
- Phosphoinositide 3-Kinase Inhibitors with a Zinc Binding MoietyPublication Number: US-2025230169-A1Priority Date: 2009-01-08
- Phosphoinositide 3-kinase inhibitors with a zinc binding moietyPublication Number: US-2023227467-A1Priority Date: 2009-01-08
- Phosphoinositide 3-kinase inhibitors with a zinc binding moietyPublication Number: US-11261195-B2Priority Date: 2009-01-08Grant Date: 2022-03-01
- 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
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References
 | |
| Clinical data | |
|---|---|
| Trade names | Betlin; 贝特琳 |
| Other names | BEBT-908 |
| Legal status | |
| Legal status | Rx in China |
| Identifiers | |
| IUPAC name | |
| CAS Number | 1235449-52-1 |
| PubChem CID | 59474330 |
| ChemSpider | 45743497 |
| UNII | DQ7TD3X4ZJ |
| ChEMBL | ChEMBL5618885 |
| Chemical and physical data | |
| Formula | C23H25N9O3S |
| Molar mass | 507.57 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
References
- Fung S (December 2025). “Ifupinostat: First Approval”. Drugs. 85 (12): 1629–1633. doi:10.1007/s40265-025-02248-z. PMID 41028651.
- “Ifupinostat – BeBetter Med”. AdisInsight. Springer Nature Switzerland AG.
- Wang N, Mo Z, Pan L, Zhou M, Ye X, Liu X, et al. (November 2023). “Dual PI3K/HDAC Inhibitor BEBT-908 Exhibits Potent Efficacy as Monotherapy for Primary Central Nervous System Lymphoma”. Targeted Oncology. 18 (6): 941–952. doi:10.1007/s11523-023-01006-z. PMID 37855991.
- Luzietti L, Pires GS, Ryan A, Regidor C, Hiller M, Sarti D, et al. (2025). “Design, synthesis, and biological evaluation of novel triazine-based dual HDAC/PI3K inhibitors for breast cancer therapy”. ChemRxiv. doi:10.26434/chemrxiv-2025-tzwbz.
/////////////ifupinostat, anax labs, Q7TD3X4ZJ, BEBT908 FREE BASE, BEBT 908
#ifupinostat, #anax labs, #Q7TD3X4ZJ, #BEBT908 FREE BASE, #BEBT 908
Gozanertinib
Gozanertinib
CAS 1226549-49-0
MF C32H31N5O3 MW533.6 g/mol
(E)-4-(dimethylamino)-N-[3-[4-[[(1S)-2-hydroxy-1-phenylethyl]amino]-6-phenylfuro[2,3-d]pyrimidin-5-yl]phenyl]but-2-enamide
(2E)-4-(dimethylamino)-N-[3-(4-{[(1S)-2-hydroxy-1-phenylethyl]amino}-6-phenylfuro[2,3-d]pyrimidin-5-yl)phenyl]but-2-
enamide
epidermal growth factor receptor tyrosine kinase inhibitor, antineoplastic, DBPR 112, ABT 101, 6G0COS33K4
Gozanertinib (also known as DBPR112 or ABT-101) is an orally bioavailable, advanced small-molecule dual kinase inhibitor designed to treat advanced non-small cell lung cancer (NSCLC). It targets alterations in the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor 2 (HER2) families.
Mechanism of Action
Gozanertinib is a furanopyrimidine-based tyrosine kinase inhibitor. It functions by entering the ATP-binding pocket of the receptor and forming an irreversible covalent bond with a specific cysteine residue (Cys797). By permanently blocking these receptors, it halts downstream oncogenic signaling pathways—specifically the RAS/RAF/MEK/ERK and PI3K/AKT cascades—thereby inducing cancer cell death and suppressing tumor expansion.
Target Profile and Key Mutations
Unlike earlier generations of tyrosine kinase inhibitors that only target standard configurations, gozanertinib is optimized to combat specific treatment-resistant mutations:
- EGFR Mutations: It effectively targets wild-type EGFR as well as the dual L858R/T790M resistance mutations.
- Exon 20 Insertions: A standout feature of gozanertinib is its preclinical potency against EGFR and HER2 exon 20 insertion (Ex20ins) mutations. According to chemical development findings published in the Journal of Medicinal Chemistry, it demonstrated ten times better potency against these specific insertions than the widely used third-generation inhibitor, osimertinib.
Development and Status
The drug was initially discovered through scaffold optimization by the National Health Research Institutes (NHRI) and is being co-developed with Anbogen Therapeutics. The International Nonproprietary Name (INN) “gozanertinib” was formally proposed for the compound in early 2025. Preclinical evaluations indicated favorable oral bioavailability and strong anti-tumor efficacy compared to older inhibitors like afatinib, advancing the compound into early-phase clinical trials
Gozanertinib is an orally bioavailable dual kinase inhibitor of epidermal growth factor receptor (EGFR; ErbB1) and human epidermal growth factor receptor 2 (HER2; EGFR2; ErbB2), including EGFR L858R, EGFR T790M and HER2 exon 20 insertion (Ex20ins) mutations, with potential antineoplastic activity. Upon oral administration, gozanertinib targets, binds to and inhibits the activity of EGFR or HER2 insertions or mutations. This prevents EGFR/HER2-mediated signaling, which may induce cell death and inhibit tumor growth in EGFR/HER2-overexpressing tumor cells. The ErbB receptor tyrosine kinase family is involved in key cellular functions, including cell growth and survival. EGFR and HER2 alterations constitutively upregulate kinase activity.
- Phase 1b/2 Study to Evaluate ABT-101 in Solid Tumor and NSCLC PatientsCTID: NCT05532696Phase: Phase 1/Phase 2Status: RecruitingDate: 2024-06-24
- A Study of DBPR112 in Patients With Head and Neck Cancer and EGFR Mutated Lung CancerCTID: NCT03246854Phase: Phase 1Status: TerminatedDate: 2020-12-17
PAT
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=US43249513&_cid=P11-MQ1QG3-86325-1
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References
- Development of Furanopyrimidine-Based Orally Active Third-Generation EGFR Inhibitors for the Treatment of Non-Small Cell Lung CancerPublication Name: Journal of Medicinal ChemistryPublication Date: 2023-02-07PMCID: PMC9969398PMID: 36749735DOI: 10.1021/acs.jmedchem.2c01434
- Discovery of a Furanopyrimidine-Based Epidermal Growth Factor Receptor Inhibitor (DBPR112) as a Clinical Candidate for the Treatment of Non-Small Cell Lung CancerPublication Name: Journal of Medicinal ChemistryPublication Date: 2019-09-27PMID: 31560541DOI: 10.1021/acs.jmedchem.9b00722
PAT
- Active cancer immunotherapy by immune modulation via globo series antigensPublication Number: EP-4248214-A1Priority Date: 2020-11-19
- Fused Bicyclic and Tricyclic Pyrimidine Compounds as Tyrosine Kinase InhibitorsPublication Number: US-2010120805-A1Priority Date: 2008-11-10
- Fused bicyclic and tricyclic pyrimidine compounds as tyrosine kinase inhibitorsPublication Number: US-8507502-B2Priority Date: 2008-11-10Grant Date: 2013-08-13
- Fused bicyclic and tricyclic pyrimidine compounds as tyrosine kinase inhibitorsPublication Number: WO-2010054285-A2Priority Date: 2008-11-10
- Fused bicyclic and polycyclic pyrimidine compounds as tyrosine kinase inhibitorsPublication Number: CN-102264745-APriority Date: 2008-11-10
- Active cancer immunotherapy through immune modulation via GLOBO series antigensPublication Number: CN-116847875-APriority Date: 2020-11-19
- Active cancer immunotherapy by immune modulation via globo series antigensPublication Number: CA-3200572-A1Priority Date: 2020-11-19
- Active cancer immunotherapy by immune modulation via globo series antigensPublication Number: WO-2022109601-A1Priority Date: 2020-11-19
- Active cancer immunotherapy by immune modulation via globo series antigensPublication Number: IL-302947-APriority Date: 2020-11-19
- Active cancer immunotherapy by immunomodulation through GLOBO family antigensPublication Number: KR-20230110529-APriority Date: 2020-11-19
- Crystalline forms of (s, e)-4-(dimethylamino)-n-(3-(4-(2-hydroxy-1-phenylethylamino)-6-phenylfuro[2,3-d]pyrimidin-5-yl)phenyl)but-2-enamide free basePublication Number: TW-I809967-BPriority Date: 2021-07-06Grant Date: 2023-07-21
- Crystalline forms of (S, E)-4-(dimethylamino)-N-(3-(4-(2-hydroxy-1-phenylethylamino)-6-phenylfuro[2,3-d]pyrimidin-5-yl)phenyl)but-2- enamide free basePublication Number: US-12240858-B2Priority Date: 2021-07-06Grant Date: 2025-03-04
- Active cancer immunotherapy by immune modulation via globo series antigensPublication Number: TW-202237177-APriority Date: 2020-11-19
- Active cancer immunotherapy by immune modulation via globo series antigensPublication Number: US-2024139301-A1Priority Date: 2020-11-19
- Active cancer immunotherapy by immune modulation via globo series antigensPublication Number: AU-2021382807-A1Priority Date: 2020-11-19
- Crystalline forms of (s, e)-4-(dimethylamino)-n-(3-(4-(2-hydroxy-1-phenylethylamino)-6-phenylfuro[2,3-d]pyrimidin-5-yl)phenyl)but-2-enamide free basePublication Number: US-2023021909-A1Priority Date: 2021-07-06
- Crystalline forms of (s, e)-4-(dimethylamino)-n-(3-(4-(2-hydroxy-1-phenylethylamino)-6-phenylfuro[2,3-d]pyrimidin-5-yl)phenyl)but-2-enamide free basePublication Number: WO-2023283269-A1Priority Date: 2021-07-06
- Crystalline forms of (s, e)-4-(dimethylamino)-n-(3-(4-(2-hydroxy-1-phenylethylamino)-6-phenylfuro[2,3-d]pyrimidin-5-yl)phenyl)but-2-enamide free basePublication Number: US-2024368175-A1Priority Date: 2021-07-06
- Crystalline forms of (s, e)-4-(dimethylamino)-n-(3-(4-(2-hydroxy-1-phenylethylamino)-6-phenylfuro[2,3-d]pyrimidin-5-yl)phenyl)but-2-enamide free basePublication Number: TW-202309041-APriority Date: 2021-07-06
- Crystalline forms of (s, e)-4-(dimethylamino)-n- (3-(4-(2-hydroxy-1-phenylethylamino)-6-phenylfuro[2,3-d]pyrimidin-5-yl)phenyl)but-2-enamide free basePublication Number: EP-4330259-A1Priority Date: 2021-07-06
//////gozanertinib, ANAX LABS, epidermal growth factor receptor tyrosine kinase inhibitor, antineoplastic, DBPR 112, ABT 101, 6G0COS33K4
#gozanertinib, #ANAX LABS, #epidermal growth factor receptor tyrosine kinase inhibitor, #antineoplastic, #DBPR 112, #ABT 101, #6G0COS33K4
Gintemetostat
Gintemetostat
(1S)-1-[(3R)-3-amino-4′-[(6-amino-9H-purin-9-yl)methyl]-6′-(2,5-difluoro-4-methoxyphenyl)-3,4,5,6-tetrahydro-2H-[1,3′-bipyridin]-3-yl]-2,2-difluoroethan1-ol
antineoplastic, KTX 1001, NSD2 inhibitor 161, A48CGJ5UQM
CAS 2604513-16-6
MF C25H26F4N8O2 MW 546.5 g/mol
(S)-1-((R)-3-Amino-1-(4-((6-amino-9H-purin-9-yl)methyl)-6-(2,5-difluoro-4-methoxyphenyl)pyridin-3-yl)piperidin-3-yl)-2,2-difluoroethan-1-ol
Gintemetostat (also known as KTX-1001) is a first-in-class, orally administered small molecule being developed to treat relapsed and refractory multiple myeloma. It works as a selective inhibitor of NSD2 (also known as MMSET), targeting the epigenetic drivers of high-risk cancers.
How it Works
- Mechanism: Gintemetostat selectively binds to the catalytic SET domain of the NSD2 enzyme.
- Effect: By blocking this enzyme, it downregulates oncogenic signaling, decreases cancer cell growth, and can enhance T-cell activation against the tumor.
Target Patient Population
- High-Risk Myeloma: The drug focuses heavily on patients harboring the t(4;14) translocation, a genetic alteration found in 10-15% of patients that often causes aggressive relapses.
- Refractory Cases: It has shown notable single-agent activity in heavily pretreated patients who have exhausted standard-of-care, triple-class refractory treatment options.
Current Clinical Status
- Phase 1 Trial: Early data from phase 1 trials (such as NCT05651932) showed the drug has manageable safety profiles and offers clinical benefit (ranging from stable disease to very good partial response) in patients with aggressive, hard-to-treat multiple myeloma.
- Future Developments: Researchers are expanding studies to pair gintemetostat with other standard myeloma treatments, such as proteasome inhibitors and CELMoDs, to create stronger synergistic anti-cancer effects.
Gintemetostat is an orally available small molecule inhibitor of the histone-lysine N-methyltransferase nuclear receptor-binding SET domain protein 2 (NSD2; MMSET; WHSC1), with potential antineoplastic activity. Upon oral administration, gintemetostat selectively targets and binds to NSD2, and inhibits its catalytic activity and the mono- and di-methylation of histone H3 lysine 36 (H3K36). This modulates the expression of genes involved in cellular processes including cellular proliferation, which may lead to decreased growth of cancer cells. NSD2, a member of the NSD family of histone lysine methyltransferase enzymes that catalyzes the mono- and di-methylation of H3K36, is overexpressed and dysregulated in many types of cancers.
SYN
Discovery of a Highly Potent and Selective Inhibitor Targeting Protein Lysine Methyltransferase NSD2
Publication Name: Journal of Medicinal Chemistry
Publication Date: 2024-09-04
PMID: 39230932
DOI: 10.1021/acs.jmedchem.4c00639
SYN
PAT
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021028854&_cid=P12-MQ0AZT-13511-1
Example 160 and Example 161: (R)-1-((R)-3-amino-1-(4-((6-amino-9H-purin-9-yl)methyl)-6- (2,5-difluoro-4-methoxyphenyl)pyridin-3-yl)piperidin-3-yl)-2,2-difluoroethan-1-ol and (S)-1-((R)-3- amino-1-(4-((6-amino-9H-purin-9-yl)methyl)-6-(2,5-difluoro-4-methoxyphenyl)pyridin-3- yl)piperidin-3-yl)-2,2-difluoroethan-1-ol
To a solution of tert-butyl (tert-butoxycarbonyl)(9-((5-(3-((tert-butoxycarbonyl)amino)-3-(2,2- difluoro-1-hydroxyethyl)piperidin-1-yl)-2-(2,5-difluoro-4-methoxyphenyl)pyridin-4-yl)methyl)-9H- purin-6-yl)carbamate (Intermediate 160-3) (200 mg, 0.237 mmol) in DCM (18 mL), was added TFA (36 mL), and the reaction mixrture was stirred at rt for 30 min under N2 atmosphere. The reaction mixture was concentrated in vacuo to give the crude product. The crude product was purifed by Pre-HPLC and SFC to afford (R)-1-((R)-3-amino-1-(4-((6-amino-9H-purin-9- yl)methyl)-6-(2,5-difluoro-4-methoxyphenyl)pyridin-3-yl)piperidin-3-yl)-2,2-difluoroethan-1-ol (Example 160) and (S)-1-((R)-3-amino-1-(4-((6-amino-9H-purin-9-yl)methyl)-6-(2,5-difluoro-4- methoxyphenyl)pyridin-3-yl)piperidin-3-yl)-2,2-difluoroethan-1-ol (Example 161).
Example 160: 1H NMR (400 MHz, CD3OD) d ppm 8.48 (s, 1H), 8.20 (d, J = 1.6 Hz, 2H), 7.58 (dd, J = 12.2, 7.3 Hz, 1H), 7.11 (d, J = 1.3 Hz, 1H), 6.90 (dd, J = 12.6, 7.1 Hz, 1H), 6.06 (td, J = 55.1, 3.9 Hz, 1H), 5.67 (s, 2H), 3.87 (s, 3H), 3.75 – 3.58 (m, 1H), 3.25 – 2.75 (m, 4H), 2.26 – 1.60 (m, 4H). LC-MS: [M+H]+ = 547.2, 548.2.
Example 161: 1H NMR (400MHz, CD3OD) d = 8.51 – 8.44 (m, 1H), 8.24 – 8.16 (m, 2H), 7.62 – 7.48 (m, 1H), 7.03 (s, 1H), 6.93 – 6.79 (m, 1H), 6.25 – 5.86 (m, 1H), 5.71 – 5.59 (m, 2H), 4.00 (m, 1H), 3.88 – 3.80 (m, 3H), 3.28 – 2.87 (m, 4H), 1.99 – 1.56 (m, 4H). LC-MS: [M+H]+ =547.4.
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References
- Piperidinyl-methyl-purineamines as nsd2 inhibitors and anti-cancer agentsPublication Number: EP-4559915-A1Priority Date: 2019-08-14
- Piperidinyl-methyl-purineamines as nsd2 inhibitors and anti-cancer agentsPublication Number: EP-4013755-B1Priority Date: 2019-08-14Grant Date: 2025-01-08
- Piperidinyl-methyl-purinamines as NSD2 inhibitors and anticancer agentsPublication Number: CN-114585622-APriority Date: 2019-08-14
- Piperidinyl-methyl-purineamines as NSD2 inhibitors and anti-cancer agentsPublication Number: US-12312353-B2Priority Date: 2019-08-14Grant Date: 2025-05-27
- Piperidinyl-methyl-purineamines as nsd2 inhibitors and anti-cancer agentsPublication Number: WO-2021026803-A1Priority Date: 2019-08-14
- Piperidinyl-methyl-purineamines as nsd2 inhibitors and anti-cancer agentsPublication Number: EP-4013755-A1Priority Date: 2019-08-14
- Piperidinyl-methyl-purineamines as nsd2 inhibitors and anti-cancer agentsPublication Number: WO-2021028854-A1Priority Date: 2019-08-14
- Piperidinyl-methyl-purineamine D-tartrate, crystalline forms, and use thereof in the treatment of medical diseases and conditionsPublication Number: CN-119744262-APriority Date: 2022-05-18
- Piperidinyl-methyl-purine amine d-tartaric acid salts, crystalline forms, and their use in treating medical diseases and conditionsPublication Number: EP-4526305-A1Priority Date: 2022-05-18
- Piperidinyl-methyl-purineamines as nsd2 inhibitors and anti-cancer agentsPublication Number: US-2023002388-A1Priority Date: 2019-08-14
- Piperidinyl-methyl-purinamines as NSD2 inhibitors and anticancer agentsPublication Number: CN-114585622-BPriority Date: 2019-08-14Grant Date: 2024-08-09
- Piperidinyl-methyl-purineamines as NSD2 inhibitors and anti-cancer agentsPublication Number: US-11420970-B1
- Piperidinyl-methyl-purine amine d-tartaric acid salts, crystalline forms, and their use in treating medical diseases and conditionsPublication Number: AU-2023273656-A1Priority Date: 2022-05-18
- Piperidinyl-methyl-purine amine salts, crystalline forms, and their use in treating medical diseases and conditionsPublication Number: WO-2023225144-A1Priority Date: 2022-05-18
- Piperidinyl-methyl-purine amine fumaric acid salts, crystalline forms, and their use in treating medical diseases and conditionsPublication Number: WO-2023225150-A1Priority Date: 2022-05-18
- Piperidinyl-methyl-purine amine salts, crystalline forms, and their use in treating medical diseases and conditionsPublication Number: US-2025326752-A1Priority Date: 2022-05-18
- Piperidinyl-methyl-purinic amine D-tartrate salt, crystalline form and their use in the treatment of medical diseases and conditionsPublication Number: KR-20250012083-APriority Date: 2022-05-18
- Pharmaceutical compositions containing a piperidinyl-methyl-purine amine and their use in treating diseases and conditionsPublication Number: US-2024207192-A1Priority Date: 2022-12-12
- Pharmaceutical compositions containing a piperidinyl-methyl-purine amine and their use in treating diseases and conditionsPublication Number: WO-2024129670-A1Priority Date: 2022-12-12
- Piperidinyl-methyl-purine amine d-tartaric acid salts, crystalline forms, and their use in treating medical diseases and conditionsPublication Number: US-2024002385-A1Priority Date: 2022-05-18
- Piperidinyl-methyl-purine amine salts, crystalline forms, and their use in treating medical diseases and conditionsPublication Number: WO-2023225154-A1Priority Date: 2022-05-18
- Piperidinyl-methyl-purine amine d-tartaric acid salts, crystalline forms, and their use in treating medical diseases and conditionsPublication Number: WO-2023225141-A1Priority Date: 2022-05-18
////////////gintemetostat, ANAX LABS, antineoplastic, KTX 1001, NSD2 inhibitor 161, A48CGJ5UQM
#gintemetostat, #ANAX LABS, #antineoplastic, #KTX 1001, #NSD2 inhibitor 161, #A48CGJ5UQM
Zidebactam
Zidebactam
FDA 2026, APPROVALS 2026
To treat complicated urinary tract infections, including pyelonephritis, caused by designated susceptible microorganisms
CAS 1436861-97-0, UNII: YPM97423DB, Wockhardt Biopharm, WCK-5107, WCK5107
Molecular Formula, C13-H21-N5-O7-S
Molecular Weight, 391.4029
Disclosed in PCT International Patent Application No. PCT/IB2012/054290D
- 01 Aug 2015 Phase-I clinical trials in Bacterial infections (In volunteers, Combination therapy) in USA (IV) (NCT02532140)
trans- sulphuric acid mono-[2-(N’-[(R)-piperidin-3-carbonyl]-hydrazinocarbonyl)-7-oxo-l,6-diaza-bicyclo[3.2.1]oct-6-yl] ester
(2S, 5R)-sulphuric acid mono-[2-(N’-[(R)-piperidin-3-carbonyl]-hydrazinocarbonyl)-7-oxo-l,6-diaza-bicyclo[3.2.1]oct-6-yl] ester
(1R,2S,5R)-l,6-Diazabicyclo [3.2.1] octane-2-carboxylic acid, 7-oxo-6-(sulfooxy)-, 2-[2-[(3R)-3-piperidinylcarbonyl]hydrazide]
trans- sulphuric acid mono-[2-(N’-[(R)-piperidin-3-carbonyl]-hydrazinocarbonyl)-7-oxo-l,6-diaza-bicyclo[3.2.1]oct-6-yl] ester
(2S, 5R)-sulphuric acid mono-[2-(N’-[(R)-piperidin-3-carbonyl]-hydrazinocarbonyl)-7-oxo-l,6-diaza-bicyclo[3.2.1]oct-6-yl] ester
(lR,2S,5R)-l,6-Diazabicyclo [3.2.1] octane-2-carboxylic acid, 7-oxo-6-(sulfooxy)-, 2-[2-[(3R)-3 -piperidinylcarbonyl] hydrazide]
1,6-Diazabicyclo(3.2.1)octane-2-carboxylic acid, 7-oxo-6-(sulfooxy)-, 2-(2-((3R)-3-piperidinylcarbonyl)hydrazide), (1R,2S,5R)-
Zidebactam potassium
cas is 1706777-49-2
Zidebactam (WCK-5107) is an antibiotic adjuvant drug which acts as a beta-lactamase inhibitor, preventing the breakdown of other antibiotic drugs.[1]
PATENT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2019016393&_cid=P20-MPYVFE-00532-1
PATENT
http://www.google.com/patents/WO2013030733A1?cl=en
Scheme-1
Example-2
trans-sulfuric acid mono-r2-(N,-r(R)-piperidin-3-carbonyll-hvdrazinocarbonyl)-7-oxo-l,6- diaza-bicyclo Γ3.2.11 oct-6-νΠ ester
Step-1: Preparation of trans-3-[N’-(6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-piperidin-l-carboxylic acid tert-butyl ester:
By using the procedure described in Step-1 of Example- 1 above, and by using trans-6-benzyloxy-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (25 gm, 0.084 mol), N,N-dimethyl formamide (625 ml), EDC hydrochloride (24 gm, 0.126 mol), HOBt (16.96 gm, 0.126 mol), (R)-N-tert-butoxycarbonyl-piperidin-3-carboxylic acid hydrazide (21.40 gm , 0.088 mol) to provide the title compound in 17.0 gm quantity, 41% yield as a white solid.
Analysis: MS (ES+) CzsHasNsOe = 502.1 (M+l);
I^NMR (CDCI3) = 8.40 (br s, IH), 7.34-7.44 (m, 5H), 5.05 (d, IH), 4.90 (d, IH), 4.00 (br d, IH), 3.82 (br s, IH), 3.30 (br s, IH), 3.16-3.21 (m, IH), 3.06 (br d, IH), 2.42 (br s, IH), 2.29-2.34 (m, IH), 1.18-2.02 (m, 4H), 1.60-1.75 (m, 4H), 1.45-1.55 (m, 2H),1.44 (s, 9H).
Step-2: Preparation of trans-3-[N’-(6-hydroxy-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-piperidin-l-carboxylic acid tert-butyl ester:
By using the procedure described in Step-2 of Example- 1 above, and by using trans-3-[N ‘ -(6-benzyloxy-7-oxo- 1 ,6-diaza-bicyclo [3.2.1 ]octane-2-carbonyl)-hydrazinocarbonyl] -(R)-piperidin-l-carboxylic acid tert-butyl ester (16.5 gm , 0.033 mol), methanol (170 ml) and 10% palladium on carbon (3.5 gm) to provide the title compound in 13.5 gm quantity as a pale pink solid and it was used for the next reaction immediately.
Analysis: MS (ES+) CiglfeNsOe = 411.1 (M+l);
Step-3: Preparation of tetrabutylammonium salt of trans-3-[N’-(6-sulfooxy-7-oxo-l,6-diaza-bicyclo [3.2.1] octane-2-carbonyl)-hydrazinocarbonyl] -(R)-piperidin- 1 -carboxylic acid tert-butyl ester:
By using the procedure described in Step-3 of Example- 1 above, and by using trans-3-[N’-(6-hydroxy-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-piperidin-1 -carboxylic acid tert-butyl ester (13.5 gm , 0.033 mol), pyridine (70 ml) and pyridine sulfur trioxide complex (26.11 gm, 0.164 mol), 0.5 N aqueous potassium dihydrogen
phosphate solution (400 ml) and tetrabutylammonium sulphate (9.74 gm, 0.033 mol) to provide the title compound in 25 gm quantity as a yellowish solid, in quantitative yield.
Analysis: MS (ES-)
as a salt = 490.0 (M-l) as a free sulfonic acid;
Step-4: trans-sulfuric acid mono-[2-(N’-[(R)-piperidin-3-carbonyl]-hydrazinocarbonyl)-7-oxo-l,6-diaza-bicyclo[3.2.1]oct-6-yl]ester:
By using the procedure described in Step-4 of Example- 1 above, and by using tetrabutylammonium salt of trans-3-[N’-(6-sulfooxy-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-piperidin-l-carboxylic acid tert-butyl ester (24 gm , 0.032 mmol), dichloromethane (60 ml) and trifluoroacetic acid (60 ml) to provide the title compound in 10 gm quantity as a white solid, in 79% yield.
Analysis: MS (ES-)= C13H21N5O7S = 390.2 (M-l) as a free sulfonic acid;
HXNMR (DMSO-d6) = 9.97 (d, 2H), 8.32 (br s, 2H), 4.00 (br s, IH), 3.81 (d, IH), 3.10-3.22 (m, 3H), 2.97-3.02 (m, 2H), 2.86-2.91 (m, IH), 2.65-2.66 (m, IH), 1.97-2.03 (m, IH), 1.57-1.88 (m, 7H).
-32.6°, (c 0.5, water).
PATENT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2015110885
PATENT
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2014135931
| Clinical data | |
|---|---|
| License data | US DailyMed: Zidebactam |
| Legal status | |
| Legal status | Investigational |
| Identifiers | |
| IUPAC name | |
| CAS Number | 1436861-97-0 |
| PubChem CID | 77846445 |
| DrugBank | DB13090 |
| ChemSpider | 44209501 |
| UNII | YPM97423DB |
| ChEMBL | ChEMBL4533605 |
| Chemical and physical data | |
| Formula | C13H21N5O7S |
| Molar mass | 391.40 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
References
- Karvouniaris M, Almyroudi MP, Abdul-Aziz MH, Blot S, Paramythiotou E, Tsigou E, et al. (April 2023). “Novel Antimicrobial Agents for Gram-Negative Pathogens”. Antibiotics. 12 (4). Basel, Switzerland: 761. doi:10.3390/antibiotics12040761. PMC 10135111. PMID 37107124.
ERTISEMENT
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WEBSITE https://www.anaxlab.com/
Discovery Solutions, Supporting the chemistry needs of clients in the Medical, Analytical and Bio Sciences
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Can’t Find? Let’s Connect
Phone : +91 897704 2010 / +91 9177075735, Email : info@anaxlab.com
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References
///////ZIDEBACTAM, ANAX LABS, FDA 2026, APPROVALS 2026, Cypsedo, WCK-5107, WCK 5107, YPM97423DB
#ZIDEBACTAM, #ANAX LABS, #FDA 2026, #APPROVALS 2026, #Cypsedo, #WCK-5107, #WCK 5107, #YPM97423DB
see………http://apisynthesisint.blogspot.in/2015/11/wck-5107-in-phase-1-from-wockhardt.html
SEE BACTAM SERIES…………..http://apisynthesisint.blogspot.in/p/bactam-series.html
C1C[C@H](CNC1)C(=O)NNC(=O)[C@@H]2CC[C@@H]3C[N@]2C(=O)N3OS(=O)(=O)O
or
O=C(NNC(=O)[C@@H]2CC[C@@H]1CN2C(=O)N1OS(=O)(=O)O)[C@@H]3CCCNC3
C1CC(CNC1)C(=O)NNC(=O)C2CCC3CN2C(=O)N3OS(=O)(=O)[O-].[Na+]
Gadosircoclamide
Gadosircoclamide
CAS 1801159-68-1
MF C23H38GdN5O7. MW653.8 g/mol
2-[4,7-bis(carboxylatomethyl)-10-[2-(cyclohexylmethylamino)-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetate;gadolinium(3+)
- [10-[2-[(Cyclohexylmethyl)amino]-2-(oxo-kappaO)ethyl]-1,4,7,10-tetraazacyclododecane-1,4,7-triacetato(3-)-kappaN1,kappaN4,kappaN7,kappaN10,kappaO1,kappaO4,kappaO7]gadolinium
- [2,2′,2”-(10-{2-[(cyclohexylmethyl)amino]-2-oxo-kappaOethyl}-1,4,7,10-tetraazacyclododecane-1,4,7-triyl-kappa4N1,N4,N7,N10)tri(acetato-kappaO)]gadolinium
radiodiagnostic agent, 7V6P6PCM4U
Gadosircoclamide (CAS # 1801159-68-1) is a specialized gadolinium-based coordination complex used primarily as a magnetic resonance imaging (MRI) contrast agent. It is designed to enhance image contrast, help visualize lesions, and accurately track abnormalities during diagnostic scans.
SYN
R=H
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2015105352&_cid=P11-MPXG49-92326-1
4) Synthesis of le.
DG3A-(f BuO)3 (3.0 g, 5.8 mmol) was added to a solution of 2-chlorocyclohexylmethylacetamid (1.2 g, 6.4 mmol) in acetanitrile (30 mL) prepared according to the conventional literature method (Cho, SD; Song, SY; Kim, . H.; Zhao, BX; Ahn, C; J oo, WH; Yoon, YJ; Falck, JR; Shin, DS B / (or. Chem. St. 2004, 25, 415) . The solution was stirred at room temperature for 24 hours. Solid impurities were removed by filtration, and the filtrate was evaporated under vacuum to obtain an oil phase residue. Subsequently, column chromatography on a silica phase (gradient elution: CH₂C1₂ to 10 % MeOH -CH₂Cl₂ , R f = 0.4 ( MeOH/ CH₂Cl₂ = A 1:9 mixture was performed and evaporated under reduced pressure to obtain a yellowish-white solid. As described in the preparation of the above Id, deprotection with TFA was performed to obtain a yellowish-white solid as a product. Yield: 2.4 g (82%). 1H R ( O): δ = 3.74/3.57 (m, 8H, -NCH₂CO₂- ) , 3.30 (m, 10H , overlapped -NCH₂CH₂N- ( 8H) & -CONHCH₂- ( 2H )), 3.10 (m, 8H, -NCH₂CH₂N- ) , 1.98/1.44/1.27 (in, 4H, -CH₂- , cyclohexyl ) , 1.88 (m, 1H, -NHCH₂CH- ) . Anal . Calculated for C₂₂H₃₅N₅₀ 0 7 · 3CF 3 C00H ■ 3H 2 0 : C, 38.14； H, 5.49； N, 7.94. Found: C, 37.83； H, 5.76； N, 8.44. MALDI-T0F MS (m/z): Calcd for C22H39N5O7,： 485.28, Found: 486.42 ([MH] + ), 508.44 ([MNa] + ).
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References
[1].
Kim T, et al., Gadolinium complex comprising do3a-tranexamic acid conjugate. WO2015105352
////////////gadosircoclamide, anax labs, radiodiagnostic agent, 7V6P6PCM4U
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Fosrugocrixan
Fosrugocrixan
CAS 2408145-38-8
MF C19H26N5O4PS2, MW483.5 g/mol
[(2R)-2-[[2-amino-5-[(1S)-1-phenylethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentyl] dihydrogen phosphate
- (2R)-2-[(2-amino-5-{[(1S)-1-phenylethyl]sulfanyl}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentyl dihydrogen phosphate
- 1-Pentanol, 2-[[2-amino-5-[[(1S)-1-phenylethyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methyl-, 1-(dihydrogen phosphate), (2R)-
(2R)-2-[(2-amino-5-{[(1S)-1-phenylethyl]sulfanyl}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentyl dihydrogen phosphate
CX3C chemokine receptor 1 (CX3CR1) antagonist, antiinflammatory, 4ZXD25SC4S, KAND-145, KAND 145
- OriginatorKancera
- DeveloperNovakand Pharma
- ClassAnti-inflammatories; Antineoplastics; Small molecules
- Mechanism of ActionChemokine CXCL13 inhibitors
- Phase IOvarian cancer
- PreclinicalChronic lymphocytic leukaemia
- No development reportedInflammation
- 22 Sep 2025Kancera is now called Novakand Pharma
- 28 Apr 2025No recent reports of development identified for preclinical development in Ovarian-cancer in Sweden (IV)
- 03 May 2024Efficacy and adverse event data from a phase I trials in healthy volunteers released by Kancera
Fosrugocrixan (also known by its developmental code KAND145) is a novel, small-molecule drug candidate acting as a selective antagonist for CX3C chemokine receptor 1 (CX3CR1), commonly known as the fractalkine receptor.
Key Characteristics and Mechanism
- Drug Class: It represents a first-in-class small molecule immune modulator.
- Phosphate Prodrug: Fosrugocrixan is designed as a soluble phosphate prodrug. Once inside the body (in vivo), it converts into its active drug form, rugocrixan (formerly KAND567).
- Mechanism of Action: By blocking the CX3CR1 fractalkine pathway, it controls and prevents the trafficking of disease-promoting immune cells. This blockage provides potent anti-inflammatory activity.
Clinical Development and Targets
The drug is being actively developed by Novakand Pharma (a company formerly known as Kancera). Its primary therapeutic targets span several conditions driven by runaway inflammation and immune responses:
- Cardiovascular Diseases: Specifically targeted to manage conditions where hyper-inflammation damages tissue (such as post-myocardial infarction or heart conditions).
- Autoimmune & Inflammatory Diseases: Evaluated for broad anti-inflammatory potential.
- Oncology: Investigated for its ability to regulate the tumor microenvironment.
SYN
WO 2020008064
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020008064&_cid=P21-MPQB4Y-95682-1
SYN
Karlström et al. J. Med. Chem., 2013, 56, 3177-3190
https://pubs.acs.org/doi/10.1021/jm3012273
PAT
(2R)-2-[(2-Amino-5-{[(1S)-1-phenylethyl]sulfanyl}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentyl dihydrogen phosphate (B), are known to act as antagonists of the fractalkine receptor (CX3CR1) (Karlström et al. J. Med. Chem., 2013, 56, 3177-3190; WO 2020/008064)
PAT
https://patentscope.wipo.int/search/en/detail.jsf?docId=US336567291&_cid=P21-MPQAYT-90868-1
Example 1
Preparation of (2R)-2-[(2-Amino-5-{[(1S)-1-phenylethyl]sulfanyl}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentyl dihydrogen phosphate
Phosphorus oxychloride (337 mg, 2.2 mmol) was dissolved in THE (0.75 mL) and water (25 mg, 1.4 mmol) was added. The mixture was cooled in an ice-bath and pyridine (111 mg, 113 μL, 1.4 mmol) was added followed by (2R)-2-[(2-amino-5-{[(1S)-1-phenylethyl]sulfanyl}-[1,3] thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol hydrochloride (110 mg, 0.25 mmol) (Karlstr6m S., et al., J. Med. Chem., 2013, 56, 3177-3190; WO 2006/107258). The reaction mixture was stirred at ice-bath temperature for 1 h. To a mixture of phosphorus oxychloride (337 mg, 2.2 mmol) and water (25 mg, 1.4 mmol) in THE was added, at ice-bath temperature pyridine (111 mg, 113 μL, 1.4 mmol). Half of this mixture was added to the reaction mixture described above. The reaction mixture was stirred at ice-bath temperature for another 1 h. Water (3 mL) was added and the reaction mixture was stirred for 15 min at ice-bath temperature and 20 min at room temperature. DCM (3 mL) was added and the phases were separated. The aqueous phase was extracted with another portion of DCM (3 mL) and the organic phases were combined. At this point the product started to precipitate as a pale-yellow gum in the organic phase. MeOH was added and the now homogeneous solution was transferred to a round-bottomed flask and was evaporated to yield 120 mg of crude product, which according to HPLC was ca. 93% pure. The crude material was dissolved in a MeOH/water mixture and the pH was adjusted to about 6-7 with 1 M NaOH. The material was purified by preparative HPLC (basic method). The pure fractions were pooled, evaporated, and dried in vacuum. The product was assumed to be the diammonium salt after purification. 1H NMR (600 MHz, CD 3OD) δ H ppm 7.43-7.47 (m, 2H) 7.30-7.35 (m, 2H) 7.20-7.24 (m, 1H) 5.08 (q, J=7.03 Hz, 1H) 4.59-4.68 (m, 1H) 3.92 (ddd, J=10.12, 5.67, 4.30 Hz, 1H) 3.88 (dt, J=10.12, 4.94 Hz, 1H) 1.74 (d, J=7.03 Hz, 3H) 1.71-1.79 (m, 1H) 1.68 (ddd, J=13.87, 9.54, 5.67 Hz, 1H) 1.57 (ddd, J=13.87, 8.54, 5.33 Hz, 1H) 0.98 (d, J=6.71 Hz, 3H) 0.96 (d, J=6.56 Hz, 3H). MS (ESI +) m/z 484 [M+H] +.
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References
- Phosphate and phosphonate derivatives of 7-amino-5-thio-thiazolo[4,5-d]pyrimidines and their use in treating conditions associated with elevated levels of cx3cr1 and/or cx3cl1Publication Number: EP-3818065-B1Priority Date: 2018-07-06Grant Date: 2023-03-15
- Phosphate and phosphonate derivatives of 7-amino-5-thio-thiazolo[4,5-d]pyrimidine and their use in treating conditions associated with elevated levels of CX3CR1 and/or CX3CL1Publication Number: KR-102736870-B1Priority Date: 2018-07-06Grant Date: 2024-12-03
- Phosphate and phosphonate derivatives of 7-amino-5-thio-thiazolo[4,5-d]pyrimidines and their use in treating conditions associated with elevated levels of cx3cr1 and/or cx3cl1Publication Number: US-2021340167-A1Priority Date: 2018-07-06
- Phosphate and phosphonate derivatives of 7-amino-5-thio-thiazolo[4,5-D]pyrimidine and their use in the treatment of conditions associated with elevated levels of cx3cr1 and/or cx3cl1 – Patent Application 20070123333Publication Number: JP-7506653-B2Priority Date: 2018-07-06Grant Date: 2024-06-26
- Phosphate and phosphonate derivatives of 7-amino-5-thio-thiazolo[4,5-d]pyrimidines and their use in treating conditions associated with elevated levels of CX3CR1 and/or CX3CL1Publication Number: US-11339183-B2Priority Date: 2018-07-06Grant Date: 2022-05-24
- Phosphate and phosphonate derivatives of 7-amino-5-thio-thiazolo-[4,5-D]-pyrimidines and their uses in the treatment of conditions associated with high levels of CX3CR1 and/or CX3CL1Publication Number: IL-279818-B1Priority Date: 2018-07-06
- PHOSPHATE AND PHOSPHONATE DERIVATIVES OF 7-AMINO-5-THIO-THIAZOLO[4,5-D]PYRIMIDINE AND THEIR USE IN THE TREATMENT OF CONDITIONS ASSOCIATED WITH INCREASED LEVELS OF CX3CR1 AND/OR CX3CL1Publication Number: HR-P20230532-T1Priority Date: 2018-07-06
- Phosphate and phosphonate derivatives of 7-amino-5-thio-thiazolo[4,5-d]pyrimidines and their use in treating conditions associated with elevated levels of CX3CR1 and/or CX3CL1Publication Number: US-12060380-B2Priority Date: 2018-07-06Grant Date: 2024-08-13
- 7-Amino-5-thio-thiazolo [4,5-D] Pyrimidine phosphate and phosphonate derivatives and their use in therapeutic conditions associated with elevated levels of CX3CR1 and / or CX3CL1Publication Number: JP-2021530474-APriority Date: 2018-07-06
- Phosphate and phosphonate derivatives of 7-amino-5-thio-thiazolo-[4,5-D]-pyrimidines and their uses in the treatment of conditions associated with high levels of CX3CR1 and/or CX3CL1Publication Number: IL-279818-B2Priority Date: 2018-07-06
- Phosphate and phosphonate derivatives of 7-amino-5-thio-thiazolo[4,5-d]pyrimidines and their use in treating conditions associated with elevated levels of cx3cr1 and/or cx3cl1Publication Number: US-2021292349-A1Priority Date: 2018-07-06
- Phosphate and phosphonate derivatives of 7-amino-5-thio-thiazolo [4,5-D ] pyrimidine modulators of CX3CR1 receptor and medical uses thereofPublication Number: CN-112867725-BPriority Date: 2018-07-06Grant Date: 2024-09-27
- New usePublication Number: US-2025195548-A1Priority Date: 2023-12-19
- Fractalkine receptor antagonists for use in the prevention of thrombus formation and/or growthPublication Number: EP-4593833-A1Priority Date: 2023-12-19
- Fractalkine receptor antagonists for use in the prevention of thrombus formation and/or growthPublication Number: WO-2025133022-A1Priority Date: 2023-12-19
- New usePublication Number: US-2025195549-A1Priority Date: 2023-12-19
- New treatments of viral infectionsPublication Number: WO-2021224494-A1Priority Date: 2020-05-08
////////fosrugocrixan, anax labs, CX3C chemokine receptor 1 (CX3CR1) antagonist, antiinflammatory, 4ZXD25SC4S, KAND-145, KAND 145
#fosrugocrixan, #anax labs, #CX3C chemokine receptor 1 (CX3CR1) antagonist, #antiinflammatory, #4ZXD25SC4S, #KAND-145, #KAND 145
Fosizensertib
Fosizensertib
CAS 2905377-00-4
MF C22H21F2N4O5P MW490.4 g/mol
[(2S)-1-[[5-[2-[1-(difluoromethyl)pyrazol-4-yl]ethynyl]pyridine-3-carbonyl]-methylamino]-3-phenylpropan-2-yl] dihydrogen phosphate
(2S)-1-(5-{[1-(difluoromethyl)-1H-pyrazol-4-yl]ethynyl}-Nmethylpyridine-3-carboxamido)-3-phenylpropan-2-yl dihydrogen
phosphate
receptor-interacting serine/threonine protein (RIP-1) kinase inhibitor, ABBV-668, ABBV 668, 6GA6XSX5SL
Fosizensertib (also known by the developmental code ABBV-668) is an investigational small molecule drug being evaluated for the treatment of ulcerative colitis and other chronic autoimmune or inflammatory conditions.
Mechanism of Action
- Target: It acts as a selective inhibitor of receptor-interacting serine/threonine-protein kinase 1 (RIPK1), an enzyme that plays a critical role in regulating cellular inflammation and necroptosis (programmed cell death).
- Prodrug Design: Fosizensertib functions as a phosphate prodrug. When administered, it is essentially inactive in vitro (inhibiting RIPK1 by less than 10%).
- Bioactivation: Once inside the body, it undergoes in vivo dephosphorylation to convert into its active metabolite (Compound 2), which strongly inhibits RIPK1 activity to suppress inflammatory pathways.
According to resources like the IUPHAR/BPS Guide to Pharmacology and PubChem, its core chemical metrics include:
Fosizensertib was assigned its International Nonproprietary Name (INN) by the World Health Organization (WHO). Developed by the pharmaceutical company AbbVie, it is classified as a clinical candidate intended for oral administration. It is currently restricted strictly to laboratory research and clinical evaluation settings and is not approved for general prescription or veterinary use.
PAT
(S)-1-(5-((1-(difluoromethyl)-1H-pyrazol-4-yl)ethynyl)-N-methylnicotinamido)-3-phenylpropan-2-yl dihydrogen phosphate;
Examples #18 and 19: (S)–di–tert–butyl (1–(5–((1–(difluoromethyl)–1H–pyrazol–4– yl)ethynyl)–N–methylnicotinamido)–3–phenylpropan–2–yl) phosphate (Example #18) and (S)–1–(5–((1–(difluoromethyl)–1H–pyrazol–4–yl)ethynyl)–N–methylnicotinamido)–3– phenylpropan–2–yl dihydrogen phosphate (Example #19)
[0173] To a solution of (S)-5-((1-(difluoromethyl)-1H-pyrazol-4-yl)ethynyl)-N-(2-hydroxy- 3-phenylpropyl)-N-methylnicotinamide (Example #2) (500 mg, 1.22 mmol) in N-Methyl-2- pyrrolidinone (1000 mL) was added di-tert-butyl diethylphosphoramidite (304 mg, 1.22 mmol) and 1H-tetrazole (10.8 mL, 4.87 mmol) in one portion at 20 °C under N2. The mixture was stirred at 40 °C for 3 hours. Hydrogen peroxide (5.0 mL, 49 mmol) was added to the solution at 0 °C, and the mixture was stirred for an additional 2 hours. The mixture was poured into saturated Na2SO3 (75 mL) and extracted with ethyl acetate (EtOAc) (3 × 100 mL). The organic phase was washed with brine (100 mL), dried over Na2SO4, concentrated under reduced pressure to give the crude t-butyl phosphate ester, which was chromatographed on silica gel (petroleum ether: ethyl acetate=1:1-1:4) to provide (S)-di-tert-butyl (1-(5-((1-(difluoromethyl)-1H-pyrazol-4- yl)ethynyl)-N-methylnicotinamido)-3-phenylpropan-2-yl) phosphate (Example #18) (384 mg, 0.64 mmol, 52% yield). LC/MS (Table B, Method aa) Rt = 1,73 min; MS m/z: 545.20 (M-tBu)+; 1H NMR (400 MHz, DMSO-d6) δ 8.76 – 8.40 (m, 3H), 8.15 – 7.60 (m, 3H), 7.27-7.01 (m, 5H), 4.78-4.46 (br m, 1H), 3.75-2.72 (m, 7H), 1.50-1.18 (m, 18H). tBu = tert–butyl; Et = ethyl.
[0174] A flask was charged with (S)-di-tert-butyl (1-(5-((1-(difluoromethyl)-1H-pyrazol-4- yl)ethynyl)-N-methylnicotinamido)-3-phenylpropan-2-yl) phosphate (Example #18) (381 mg, .632 mmol), dichloromethane (DCM) (5 mL) and trifluoroacetic acid (TFA) (0.61 mL, 7.9 mmol) and stirred at room temperature for approximately 19 hours. The mixture was concentrated under reduced pressure, then purified via reverse phase liquid chromatography (Atlantis® Prep T3 Phenomenex 5 μm 19 x 50 mm column, 5 to 95 acetonitrile (MeCN):water (formic acid buffer) at 1 mL/minute) to provide the title compound, Example #19 (230 mg, 0.47 mmol, 74% yield). LC/MS (Table B, Method ff) Rt = 1.96 min; MS m/z: 491.0 (M+H)+; 1H NMR (400 MHz,
DMSO-d6) δ 8.78 – 8.69 (m, 1H), 8.65 – 8.57 (m, 1H), 8.44 (d, J = 1.0 Hz, 1H), 8.14 – 8.08 (m, 1H), 8.03 – 7.99 (m, 1H), 7.97 (s, 1H), 7.88 – 7.84 (m, 1H), 7.76 (s, 1H), 7.73 – 7.69 (m, 1H), 7.35 – 7.28 (m, 2H), 7.27 – 7.21 (m, 1H), 7.19 – 7.12 (m, 1H), 7.03 (br d, J = 7.5 Hz, 1H), 4.80 – 4.73 (m, 1H), 4.52 – 4.45 (m, 1H), 3.84 – 3.76 (m, 1H), 3.66 (br d, J = 13.5 Hz, 1H), 3.33 (br dd, J = 9.5, 13.5 Hz, 1H), 3.27 – 3.11 (m, 1H), 3.08 – 3.00 (m, 1H), 2.97 (s, 1H), 2.95 (br s, 1H), 2.92 (s, 2H), 2.90 – 2.85 (m, 1H), 2.79 – 2.69 (m, 1H), 2.07 (s, 1H), 1.78 (s, 1H), 1.74 (s, 1H).
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References
- Nicotinamide ripk1 inhibitorsPublication Number: WO-2023018643-A1Priority Date: 2021-08-10
- Nicotinamide ripk1 inhibitorsPublication Number: EP-4301744-A1Priority Date: 2021-08-10
- Nicotinamide RIPK1 inhibitorsPublication Number: US-11767310-B2Priority Date: 2021-08-10Grant Date: 2023-09-26
- Nicotinamide ripk1 inhibitorsPublication Number: US-2023127127-A1Priority Date: 2021-08-10
/////////fosizensertib, anax labs, ABBV-668, ABBV 668, 6GA6XSX5SL
#fosizensertib, #anax labs, #ABBV-668, #ABBV 668, #6GA6XSX5SL
Bulevirtide-gmod
Bulevirtide-gmod
CAS 2012558-47-1.
MF C248H355N65O72 MW 5399 g/mol
FDA 2026, APPROVALS 2026, 5/22/2026, Hepcludex, WKM56H3TLB
To treat chronic hepatitis delta virus infection in adults without cirrhosis or with compensated cirrhosis
N-myristoyl-glycyl-L-threonyl-L-asparagyl-L-leucyl-L-seryl-L-valyl-L-prolyl-L-asparagyl-L-prolyl-L-leucyl-glycyl-L-phenylalanyl-L-phenylalanyl-L-prolyl-L-alpha-aspartyl-L-histidyl-L-glutaminyl-L-leucyl-L-alpha-aspartyl-L-prolyl-L-alanyl-L-phenylalanyl-glycyl-L-alanyl-L-asparagyl-L-seryl-L-asparagyl-L-asparagyl-L-prolyl-L-alpha-aspartyl-L-tryptophyl-L-alpha-aspartyl-L-phenylalanyl-L-asparagyl-L-prolyl-L-asparagyl-L-lysyl-L-alpha-aspartyl-L-histidyl-L-tryptophyl-L-prolyl-L-alpha-glutamyl-L-alanyl-L-asparagyl-L-lysyl-L-valyl-glycinamide
(4S)-4-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-4-amino-2-[[(2S)-1-[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-4-amino-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-1-[(2S)-4-amino-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S,3R)-3-hydroxy-2-[[2-(tetradecanoylamino)acetyl]amino]butanoyl]amino]-4-oxobutanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]-4-oxobutanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-carboxypropanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-5-oxopentanoyl]amino]-4-methylpentanoyl]amino]-3-carboxypropanoyl]pyrrolidine-2-carbonyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]acetyl]amino]propanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]-4-oxobutanoyl]amino]-4-oxobutanoyl]pyrrolidine-2-carbonyl]amino]-3-carboxypropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-carboxypropanoyl]amino]-3-phenylpropanoyl]amino]-4-oxobutanoyl]pyrrolidine-2-carbonyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]-3-carboxypropanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carbonyl]amino]-5-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-6-amino-1-[[(2S)-1-[(2-amino-2-oxoethyl)amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Bulevirtide-gmod, sold under the brand name Hepcludex, is the first and only FDA-approved medication for treating chronic hepatitis delta virus (HDV) infection in adults. Developed by Gilead Sciences, it received accelerated approval from the U.S. Food and Drug Administration (FDA) on May 22, 2026, filling a critical gap for patients with this severe viral liver disease.
Indication and Clinical Use
- Target Patient Profile: Approved for adults with chronic HDV who have compensated cirrhosis or no cirrhosis.
- The Clinical Need: HDV only occurs as a co-infection in individuals who already have Hepatitis B (HBV). It is considered the most aggressive form of viral hepatitis, often accelerating liver scarring (fibrosis), liver failure, and liver cancer.
- Basis of Approval: The FDA granted accelerated approval based on Phase 3 MYR301 study data, which demonstrated a significant reduction in viral HDV RNA and the normalization of alanine aminotransferase (ALT) liver enzymes.
Mechanism of Action
Bulevirtide-gmod is a first-in-class entry inhibitor. It works by binding to and blocking the sodium taurocholate co-transporting polypeptide (NTCP) receptor on liver cells. Because HDV and HBV rely on this specific receptor to enter hepatocytes, the drug successfully disrupts the viral life cycle and prevents the virus from spreading to healthy liver cells.
Dosage and Administration
- Form: Supplied as a lyophilized powder for injection.
- Dose: The recommended dose is 8.5 mg once daily.
- Administration: Delivered via subcutaneous injection (under the skin).
Safety and Side Effects
- Boxed Warning: The drug carries a prominent warning regarding the risk of severe acute exacerbations of hepatitis D and B if treatment is discontinued. Stopping the medication can cause severe, life-threatening viral flares, requiring close medical monitoring for at least 6 months post-treatment.
- Common Side Effects: The most frequent adverse reactions of patients) include:
- Injection site reactions
- Headache
- Abdominal pain
- Fatigue
- Pruritus (itching)
Bulevirtide, sold under the brand name Hepcludex, is an antiviral medication used for the treatment of chronic hepatitis D (in the presence of hepatitis B).[8]
The most common side effects include raised levels of bile salts in the blood and reactions at the site of injection.[8]
Bulevirtide works by attaching to and blocking a receptor (target) through which the hepatitis delta and hepatitis B viruses enter liver cells.[8] By blocking the entry of the virus into the cells, it limits the ability of HDV to replicate and its effects in the body, reducing symptoms of the disease.[8]
Bulevirtide was approved for medical use in the European Union in July 2020,[8] and in Canada in August 2025.[5]
Medical uses
Bulevirtide is indicated for the treatment of chronic hepatitis delta virus (HDV) infection in plasma (or serum) HDV-RNA positive adult patients with compensated liver disease.[8][10]
Pharmacology
Mechanism of action
Bulevirtide binds and inactivates the sodium/bile acid cotransporter, blocking both hepatitis B and hepatitis D viruses from entering hepatocytes.[11]
The hepatitis B virus uses its surface lipopeptide pre-S1 for docking to mature liver cells via their sodium/bile acid cotransporter (NTCP) and subsequently entering the cells. Myrcludex B is a synthetic N-acylated pre-S1[12][13] that can also dock to NTCP, blocking the virus’s entry mechanism.[14]
Bulevirtide is also effective against hepatitis D because the hepatitis D virus uses the same entry receptor as the hepatitis B virus and is only effective in the presence of a hepatitis B virus infection.[14]
Pre-clinical data in mice suggests that pharmacological inhibition of NTCP-mediated bile salt uptake may also be effective to lower hepatic bile salt accumulation in cholestatic conditions. This reduces hepatocellular damage.[15] An increased ratio of phospholipid to bile salts seen in bile upon NTCP inhibition may further contribute to the protective effect as bile salts are less toxic in presence of phospholipids.[16]
Structural formula
Bulevirtide is a 47-amino acid peptide with the following sequence:[17]
CH3(CH2)12CO–Gly–Thr–Asn–Leu–Ser–Val–Pro-Asn-Pro-Leu-Gly-Phe-Phe-Pro-Asp–His–Gln-Leu-Asp-Pro-Ala-Phe-Gly-Ala-Asn-Ser-Asn-Asn-Pro-Asp-Trp-Asp-Phe-Asn-Pro-Asn-Lys-Asp-His-Trp-Pro-Glu-Ala-Asn-Lys-Val-Gly-NH2 (C13H27CO-GTNLSVPNPLGFFPDHQLDPAFGANSNNPDWDFNPNKDHWPEANKVG-NH2)
SYN
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2024073572&_cid=P11-MPNG4J-82875-1
PATENTS
- Therapy of atherosclerosis, primary biliary cirrhosis and nrlp3 inflammasome-associated disease by htcp inhibitorsPublication Number: EP-3392267-A1Priority Date: 2017-04-18
- Therapy of atherosclerosis, primary biliary cirrhosis and nrlp3 inflammasome-associated disease by htcp inhibitorsPublication Number: US-2018296634-A1Priority Date: 2017-04-18
- Therapy of atherosclerosis, primary biliary cirrhosis and nrlp3 inflammasome-associated disease by htcp inhibitorsPublication Number: US-2021196786-A1Priority Date: 2017-04-18
- Therapy of atherosclerosis, primary biliary cirrhosis and NRLP3 inflammasome-associated disease by HTCP inhibitorsPublication Number: US-10925925-B2Priority Date: 2017-04-18Grant Date: 2021-02-23
- Combination therapy of hbv and hdv infectionPublication Number: EP-3204030-B1Priority Date: 2014-10-07Grant Date: 2022-04-27
- Combination therapy of hbv and hdv infectionPublication Number: EP-4098273-A1Priority Date: 2014-10-07
- Combination therapy of hbv and hdv infectionPublication Number: US-2022040178-A1Priority Date: 2014-10-07
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References
References
- Deterding K, Wedemeyer H (2019). “Beyond Pegylated Interferon-Alpha: New Treatments for Hepatitis Delta”. AIDS Reviews. 21 (3): 126–134. doi:10.24875/AIDSRev.19000080. PMID 31532397. S2CID 202674681.
- “Hepcludex (bulevirtide acetate)”. Therapeutic Goods Administration (TGA). 12 August 2024. Retrieved 12 October 2024.
- “Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024”. Federal Register of Legislation. 30 May 2024. Retrieved 10 June 2024.
- “Hepcludex (Gilead Sciences Pty Ltd)”. Therapeutic Goods Administration (TGA). 13 September 2024. Retrieved 15 September 2024.
- “Hepcludex Product information”. Health Canada. 8 August 2025. Retrieved 20 August 2025.
- “Summary Basis of Decision for Hepcludex”. Drug and Health Products Portal. 29 September 2025. Retrieved 12 October 2025.
- “Hepcludex 2 mg powder for solution for injection – Summary of Product Characteristics (SmPC)”. (emc). 30 March 2022. Retrieved 1 July 2022.
- “Hepcludex EPAR”. European Medicines Agency (EMA). 26 May 2020. Retrieved 12 August 2020. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
- “Hepcludex Product information”. Union Register of medicinal products. Retrieved 3 March 2023.
- “Summary of opinion: Hepcludex” (PDF). European Medicines Agency (EMA). 28 May 2020.
- Francisco EM (29 May 2020). “Hepcludex”. European Medicines Agency (EMA). Archived from the original on 15 June 2020. Retrieved 6 August 2020.
- Volz T, Allweiss L, Ben MBarek M, Warlich M, Lohse AW, Pollok JM, et al. (May 2013). “The entry inhibitor Myrcludex-B efficiently blocks intrahepatic virus spreading in humanized mice previously infected with hepatitis B virus”. Journal of Hepatology. 58 (5): 861–867. doi:10.1016/j.jhep.2012.12.008. PMID 23246506.
- Abbas Z, Abbas M (August 2015). “Management of hepatitis delta: Need for novel therapeutic options”. World Journal of Gastroenterology. 21 (32): 9461–9465. doi:10.3748/wjg.v21.i32.9461. PMC 4548107. PMID 26327754.
- Spreitzer H (14 September 2015). “Neue Wirkstoffe – Myrcludex B”. Österreichische Apothekerzeitung (in German) (19/2015): 12.
- Na+ -taurocholate cotransporting polypeptide inhibition has hepatoprotective effects in cholestasis in mice. Slijepcevic D, Roscam Abbing RLP, Fuchs CD, Haazen LCM, Beuers U, Trauner M, Oude Elferink RPJ, van de Graaf SFJ. Hepatology. 2018 Sep;68(3):1057-1069. doi: 10.1002/hep.29888
- Roscam Abbing RL, Slijepcevic D, Donkers JM, Havinga R, Duijst S, Paulusma CC, et al. (January 2020). “Blocking Sodium-Taurocholate Cotransporting Polypeptide Stimulates Biliary Cholesterol and Phospholipid Secretion in Mice”. Hepatology. 71 (1): 247–258. doi:10.1002/hep.30792. PMC 7003915. PMID 31136002.
- Sauter M, Blank A, Stoll F, Lutz N, Haefeli WE, Burhenne J (September 2021). “Intact plasma quantification of the large therapeutic lipopeptide bulevirtide”. Analytical and Bioanalytical Chemistry. 413 (22): 5645–5654. doi:10.1007/s00216-021-03384-7. PMC 8410713. PMID 34018034.
| Clinical data | |
|---|---|
| Pronunciation | /bjuːˈlɛvɪrtaɪd/ byoo-LEH-vir-tyde |
| Trade names | Hepcludex |
| Other names | MyrB, Myrcludex-B[1] |
| License data | US DailyMed: Bulevirtide |
| Pregnancy category | AU: B1[2] |
| Routes of administration | Subcutaneous |
| ATC code | J05AX28 (WHO) |
| Legal status | |
| Legal status | AU: S4 (Prescription only)[3][4][2]CA: ℞-only[5][6]UK: POM (Prescription only)[7]EU: Rx-only[8][9] |
| Identifiers | |
| CAS Number | 2012558-47-1 |
| DrugBank | DB15248 |
| ChemSpider | 129157549 |
| UNII | WKM56H3TLB |
| KEGG | D11877as salt: D11878 |
| ChEMBL | ChEMBL4297711 |
| Chemical and physical data | |
| Formula | C248H355N65O72 |
| Molar mass | 5398.951 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES | |
| InChI | |
/////////Bulevirtide-gmod, ANAX LABS, FDA 2026, APPROVALS 2026, Hepcludex, WKM56H3TLB, ANTIVIRALS
#Bulevirtide-gmod, #ANAX LABS, #FDA 2026, #APPROVALS 2026, #Hepcludex, #WKM56H3TLB, #ANTIVIRALS
Flormotridazum (18F)
Flormotridazum (18F)
CAS 2798832-03-6
MF C23H29Cl18FN5O4 MW492.961
2-tert-butyl-4-chloro-5-[(3-{[4-({2-[2-(18F)fluoroethoxy]ethoxy}methyl)-1H-1,2,3-triazol-1-yl]methyl}phenyl)methoxy]pyridazin-3(2H)-one
| 3(2H)-Pyridazinone, 4-chloro-2-(1,1-dimethylethyl)-5-[[3-[[4-[[2-[2-(fluoro-18F)ethoxy]ethoxy]methyl]-1H-1,2,3-triazol-1-yl]methyl]phenyl]methoxy]- |
2-tert-butyl-4-chloro-5-[(3-{[4-({2-[2-(18F)fluoroethoxy]ethoxy}methyl)-1H-1,2,3-triazol-1-yl]methyl}phenyl)methoxy]pyridazin-3(2H)-one
imaging agent, 7AR6ZH8YUU
Flormotridaz (18F) (also referred to by its International Nonproprietary Name, flormotridazum) is an advanced radiopharmaceutical compound utilized in nuclear medicine. It is specifically engineered as a radioactive diagnostic tracer containing the fluorine-18 positron-emitting isotope.
Core Characteristics & Chemical Profile
- Substance Classification: Radioactive Diagnostic Agent / Small Molecule.
- Mechanism Basis: It shares core structural similarities and structural lineage with pyridazinone-based mitochondrial complex 1 (MC-1) inhibitors, heavily linking its functionality to target-specific tissues with high metabolic or mitochondrial activity.
Mechanism and Clinical Application
Like related fluorine-18 labeled pyridazinone analogues, this agent is designed for Positron Emission Tomography (PET) imaging workflows. [1]
- Administration: The agent is administered intravenously as a sterile unit dose before scanning.
- Cellular Targeting: It binds selectively to specific intracellular molecular targets (such as mitochondrial pathways) within highly active tissues.
- PET Imaging: As the Fluorine-18 radioisotope decays, it emits positrons. These positrons encounter electrons to produce gamma rays, which the PET scanner captures to map high-resolution, three-dimensional metabolic layouts of internal organ systems.
Contextual Comparison
In clinical nuclear medicine, molecular tracers tagged with Fluorine-18 offer significant clinical benefits over older Single-Photon Emission Computed Tomography (SPECT) agents. Their 110-minute half-life allows them to be manufactured at centralized cyclotron facilities and distributed directly to regional medical centres as ready-to-use unit doses, eliminating the need for an on-site cyclotron
Flormotridaz (\(^{18}\text{F}\)):
- CN112807276B: “Preparation method and application of a pyridazinone myocardial perfusion PET radiopharmaceutical” (Covers the definitive radiosynthesis scheme).
- CN115947775A: “Method for preparing compound (I), compound (I), and uses thereof”.
- WO2024008073A1 / CN114832118B: “Compound I liquid composition, preparation method and use thereof” (Covers final formulation stabilization utilizing vitamin C and gentisic acid)
PAT
https://patents.google.com/patent/WO2024008073A1/zh
Compound I, chemically named 2-tert-butyl-4-chloro-5-((3-((4-((2-(2-fluoro[ 18F ]ethoxy)ethoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)benzyl)oxy)pyridazine-3(2H)-one. Chemical structural formula:Molecular formula : C₂₃H₂₉Cl₁₈FN₅O₄
Molecular weight: 492.97The mechanism of action of compound I as a myocardial perfusion PET imaging agent: Once compound I enters cardiomyocytes, it can rapidly interact with respiratory chain complex I (MC-I) in mitochondria and remain in the myocardium for a long time. Preliminary animal studies showed that it has high cardiac uptake and low hepatic uptake 15 minutes after injection, and maintains a good heart-liver ratio 60 minutes after injection, showing good potential for myocardial perfusion imaging.In this application, Compound I liquid composition or Compound I is used as a myocardial perfusion PET imaging agent.Precursor of Compound I: Chemical name is methyl 2-(2-((1-(3-(((1-(tert-butyl)-5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)oxy)methyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)ethoxy)ethyl-4-methylbenzenesulfonate, chemical structural formula is:Molecular formula : C30H36ClN5O7S
Molecular weight: 646.16Amino polyethers (K222 ) are tribridged crown ether molecules with cavitary structures, and are typical nitrogen-containing cavitary ethers, belonging to the category of cavitary ethers. Due to their unique coordination properties, nitrogen-containing cavitary ethers can effectively and selectively complex transition metal and heavy metal cations, forming more stable complexes. Furthermore, they possess both lipophilic and hydrophilic properties, thus showing promising research potential.In existing technologies, the classic synthetic method for amino polyether (K
222 ) is the highly diluted method proposed by Lehn et al., which is a typical non-template ion synthesis method. The specific steps involve dissolving the starting materials 1,8-diamino-3,6-dioxane and 1,8-diacyl chloride-3,6-dioxane in a large amount of benzene solvent and heating the reaction for 8 hours. Then, a reduction reaction with lithium aluminum hydride is performed for 24 hours, followed by column chromatography separation and recrystallization to obtain amino polyether (K
222 ). This method requires a large amount of solvent, such as benzene, has a long synthetic route, is complex, has a low yield, and is not economically efficient. Besides the highly diluted method, another classic synthetic method for amino polyether (K222 ) is proposed by Kulstad and Malmsten, which uses Na 2CO 3
as a template to obtain a sodium iodide complex of amino polyether (K 222 ) in acetonitrile , and then decomplexes it using a resin to obtain amino polyether (K 222 ). The specific steps are as follows: 1,2-bis(2-iodoethoxy)ethane and benzylamine are refluxed in acetonitrile solution for 3 days. An intermediate is then obtained through post-processing. This intermediate is recrystallized from acetone and filtered to obtain a NaI complex. This complex is then decomplexed under acidic conditions using cation exchange resins and anion exchange resins to prepare amino polyether (K222 ) . This method uses simple equipment, requires little solvent, and has relatively mild reaction conditions. However, the applicant has found that the decomplexing method using ion exchange resins fails to proceed when the sodium ion content decreases to a certain level, resulting in a low yield.
PAT
https://patents.google.com/patent/CN114773179B/en
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References
//////////flormotridazum (18F), anax labs, imaging agent, 7AR6ZH8YUU
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