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Gridegalutamide

January 28, 2026 3:01 am / Leave a comment

Gridegalutamide

CAS 2446929-86-6

MF C41H45F3N8O5S MW818.9 g/mol

2-[(2R)-4-[2-[4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl]-2-ethylphenoxy]ethyl]-2-methylpiperazin-1-yl]-N-[3-[[(3R)-2,6-dioxopiperidin-3-yl]amino]phenyl]acetamide

antiandrogen, antineoplastic, BMS 986365, CC 94676, BMS-986365, CC-94676, CEL 010355,

VA228VR2DI,

Gridegalutamide is an investigational oral androgen receptor (AR) degrader being developed for the treatment of metastatic castration-resistant prostate cancer (mCRPC). It belongs to a class of drugs called proteolysis targeting chimeras (PROTACs), which are designed to selectively degrade specific proteins by hijacking the ubiquitin-proteasome system.^[1][2] CC-94676 employs a unique dual mechanism of action, combining AR degradation with AR antagonism, potentially offering advantages over traditional AR inhibitors in overcoming resistance mechanisms.^[3] Initially developed by Celgene and now under Bristol Myers Squibb, CC-94676 has demonstrated AR protein degradation and suppression of tumor growth in CRPC mouse models.^[2] As of 2024, CC-94676 is being evaluated in phase I clinical trials for patients with mCRPC who have progressed on androgen deprivation therapy and at least one prior secondary hormonal therapy.^[1][2]

Gridegalutamide is a small molecule drug. The usage of the INN stem ‘-lutamide’ in the name indicates that Gridegalutamide is a non-steroid antiandrogen. Gridegalutamide is under investigation in clinical trial NCT04428788 (Study to Evaluate the Safety and Tolerability of CC-94676 in Participants With Metastatic Castration-Resistant Prostate Cancer). Gridegalutamide has a monoisotopic molecular weight of 818.32 Da.

GRIDEGALUTAMIDE is a small molecule drug with a maximum clinical trial phase of II (across all indications) and has 3 investigational indications.

Gridegalutamide is an orally bioavailable androgen receptor (AR) degrader, with potential antineoplastic activity. Upon administration, gridegalutamide causes degradation of AR, prevents AR-mediated signaling and inhibits the proliferation of AR-overexpressing tumor cells. AR plays a key role in tumor cell proliferation in castration-resistant prostate cancer (CRPC).

A Study to Evaluate the Drug Levels, Metabolism and Excretion, and Absolute Bioavailability of BMS-986365 in Healthy Male ParticipantsCTID: NCT06433505Phase: Phase 1Status: CompletedDate: 2025-03-26
Study to Evaluate the Safety and Tolerability of CC-94676 in Participants With Metastatic Castration-Resistant Prostate CancerCTID: NCT04428788Phase: Phase 1Status: CompletedDate: 2025-12-22

SYN

DRUGHUNTER

https://drughunter.com/molecule/gridegalutamide-bms-986365-cc-94676

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020132014&_cid=P22-MKXFFS-18439-1

Example 17: 2-((R)-4-(2-(4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2- thioxoimidazolidin-1-yl)-2-ethylphenoxy)ethyl)-2-methylpiperazin-1-yl)-N-(3-((2,6- dioxopiperidin-3-yl)amino)phenyl)acetamide hydrochloride

PAT

Combination therapy with substituted 3- ((3-aminophenyl) amino) piperidine-2, 6-dione compoundsPublication Number: CN-120152718-APriority Date: 2022-11-09
Combination therapy with substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compoundsPublication Number: WO-2024102706-A1Priority Date: 2022-11-09
Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewithPublication Number: US-2020199073-A1Priority Date: 2018-12-19
Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewithPublication Number: US-11149007-B2Priority Date: 2018-12-19Grant Date: 2021-10-19
Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewithPublication Number: US-11873283-B2Priority Date: 2018-12-19Grant Date: 2024-01-16
Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewithPublication Number: US-2024368083-A1Priority Date: 2018-12-19
Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewithPublication Number: US-12404241-B2Priority Date: 2018-12-19Grant Date: 2025-09-02
Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewithPublication Number: US-2023002321-A1Priority Date: 2018-12-19

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References

Salama AK, Trkulja MV, Casanova E, Uras IZ (December 2022). “Targeted Protein Degradation: Clinical Advances in the Field of Oncology”. International Journal of Molecular Sciences. 23 (23) 15440. doi:10.3390/ijms232315440. PMC 9741350. PMID 36499765.
Xie H, Liu J, Alem Glison DM, Fleming JB (2021). “The clinical advances of proteolysis targeting chimeras in oncology”. Exploration of Targeted Anti-Tumor Therapy. 2 (6): 511–521. doi:10.37349/etat.2021.00061. PMC 9400722. PMID 36046114.
Rathkopf DE, Patel MR, Choudhury AD, Rasco D, Lakhani N, Hawley JE, et al. (September 2024). “Safety and clinical activity of BMS-986365 (CC-94676), a dual androgen receptor ligand-directed degrader and antagonist, in heavily pretreated patients with metastatic castration-resistant prostate cancer”. Annals of Oncology. 36 (1): 76–88. doi:10.1016/j.annonc.2024.09.005. PMC 12094577. PMID 39293515.

Clinical data

Other names	BMS-986365; CC-94676
Identifiers
IUPAC name
CAS Number	2446929-86-6
PubChem CID	153513643
ChemSpider	133326102
UNII	VA228VR2DI
KEGG	D12866
ChEMBL	ChEMBL6068413
Chemical and physical data
Formula	C₄₁H₄₅F₃N₈O₅S
Molar mass	818.92 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

//////////gridegalutamide, ANAX, ADVECT, antiandrogen, antineoplastic, BMS 986365, CC 94676, BMS-986365, CC-94676, CEL 010355, VA228VR2DI,

Frespaciguat

January 26, 2026 2:34 am / Leave a comment

Frespaciguat

CAS 2101645-33-2

MF C27H22ClF5N6O3 MW 608.9 g/mol

3-[4-[(5S)-4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)indazol-3-yl]-5-methyl-6-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl]phenyl]propanoic acid

3-{4-[(5S)-4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl]phenyl}propanoic acid
guanylate cyclase activator, MK5475, MK 5475, sGC activator 1, 6DXN080KGB

Frespaciguat (development code MK-5475) is an experimental inhaled soluble guanylate cyclase stimulator developed by Merck for pulmonary arterial hypertension.^[1][2][3][4]

Frespaciguat is a small molecule drug. The usage of the INN stem ‘-ciguat’ in the name indicates that Frespaciguat is a guanylate cyclase activator and stimulator. Frespaciguat is under investigation in clinical trial NCT05612035 (Frespaciguat (MK-5475) INSIGNIA-PH-COPD: A Study of the Efficacy and Safety of Frespaciguat (an Inhaled sGC Stimulator) in Adults With PH-COPD). Frespaciguat has a monoisotopic molecular weight of 608.14 Da.

Frespaciguat (MK-5475) in Participants With Pulmonary Hypertension Associated With Chronic Obstructive Pulmonary Disease (PH-COPD) (MK-5475-006)CTID: NCT04370873Phase: Phase 1Status: CompletedDate: 2025-05-28
A Study of the Efficacy and Safety of Frespaciguat (MK-5475) in Participants With Pulmonary Arterial Hypertension (INSIGNIA-PAH: Phase 2/3 Study of an Inhaled sGC Stimulator in PAH) (MK-5475-007)CTID: NCT04732221Phase: Phase 2/Phase 3Status: CompletedDate: 2025-05-25
Frespaciguat (MK-5475) in Participants With Hypoxemia Due to COVID-19 Pneumonia (MK-5475-009)CTID: NCT04425733Phase: Phase 1Status: WithdrawnDate: 2025-05-15
Frespaciguat (MK-5475) INSIGNIA-PH-COPD: A Study of the Efficacy and Safety of Frespaciguat (an Inhaled sGC Stimulator) in Adults With PH-COPDCTID: NCT05612035Phase: Phase 2Status: Active, not recruitingDate: 2025-10-07
A Study of Single Doses of Frespaciguat (MK-5475) on Pulmonary Vascular Resistance (MK-5475-002)CTID: NCT03744637Phase: Phase 1Status: CompletedDate: 2025-06-04

SYN

US10030027,

https://patentscope.wipo.int/search/en/detail.jsf?docId=US199416000&_cid=P12-MKUJSJ-89968-1

Example 10B

(S)-3-(4-{4-Amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl}phenyl)propanoic acid

Step A—(S)-Methyl 3-(4-{4-Amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl}phenyl)propanoate

In a flask containing I-A1 (91 mg, 0.27 mmol), I-11B (80 mg, 0.24 mmol) and potassium bicarbonate (73.2 mg, 0.73 mmol) in t-BuOH (2.4 mL) was stirred at 80° C. for 16 h. The reaction was cooled to RT, diluted with EtOAc and water, and extracted with EtOAc (3×). The organic layers were combined, washed with brine, dried over anhydr. Na ₂SO ₄, and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography with (EtOAc:EtOH 3:1):hexane (0-40%) to afford the title compound. m/z=623 (M+1).

Step B—(S)-3-(4-{4-Amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl}phenyl)propanoic acid

In a flask containing (S)-methyl 3-(4-{4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl}phenyl)propanoate (120 mg, 0.19 mmol) in dioxane (8.7 mL) was added LiOH (46 mg, 1.93 mmol) in water (1 mL). The reaction was stirred 2 h at 50° C. The reaction was cooled to RT, concentrated in vacuo and diluted with EtOAc. Acetic acid (132 μl, 2.31 mmol) was added and the mixture was extracted with EtOAc (3×). The organic layers were combined, washed with brine (2×), dried over anhydr. MgSO ₄, and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography with (EtOAc:EtOH 3:1):hexane (0-100%) to afford the title compound Ex-10B. ¹H NMR (400 MHz, DMSO-d ₆) δ 12.12 (s, 1H), 11.09 (s, 1H), 8.69 (d, J=8.7 Hz, 1H), 8.03 (d, J=1.7 Hz, 1H), 7.26 (dd, J=8.7, 1.7 Hz, 1H), 7.22-7.11 (m, 4H), 6.54 (s, 2H), 4.82 (t, J=6.8 Hz, 2H), 2.90 (tt, J=19.4, 6.9 Hz, 2H), 2.77 (t, J=7.6 Hz, 2H), 2.52-2.49 (m, 2H), 1.76 (s, 3H); m/z=609 (M+1).

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2025006295&_cid=P12-MKUJNS-84717-1

EXAMPLE 2

[0038] To an autoclave was charged anisole (12.78 L), indazole ester (IV) (2.13 kg, 5.64 mol), and hexamethyldisilazane (4.55 kg, 28.2 mol). The mixture was cooled to 0-5 ^oC and the vessel was placed under slight positive pressure with no N₂ sweeping. A solution of H₂O (203.21 g, 11.27 mol) in sulfolane (6.39 L) was added while keeping at < 10 ^oC in order to minimize NH3 gas escaping. The resulting mixture was cooled to -10 ^oC, then TfOH (1.692 kg, 11.27 mol) was slowly added at < 22 ^oC. The vessel was sealed and the mixture was heated at 120-130 °C for 24 h. The upper vessel was kept warm so that solid ammonium triflate did not deposit there.

[0039] After cooling the mixture to rt, the batch (biphasic) was further cooled to 0-10 ^oC.2.4 equiv 1N KOH (13.53 L, 14.207 kg, 13.53 mol) was slowly added at < 25 ^oC. After agitating for 30 min, and letting settle at rt, the bottom aqueous layer was removed (pH~14). The organic layer was washed with 18% brine (10.5 L). The aqueous layer was removed (pH ~12). To the organic phase was added ¼ (101 mL, 149 g) of 1.1 equiv methanesulfonic acid (402 mL, 595 g, 6.20 mol), then seeded with 0.2 wt% amidine MSA type A (8.5 g). The rest of MSA (447 g, 302 mL) was then slowly added over 1 h. During MSA addition, the temperature was controlled at < 25 ^oC. The resulting slurry, after aging at 22 ^oC for 15 h, was filtered, then displacement washed with 2 x 3 vol 2-MeTHF (2 x 6.4 L), and vacuum dried under N₂ at < 30 °C for 24 h. The product (III) was obtained (4.62 kg, 10.58 mol, 93 % yield) as an off-white to light beige solid.

PAT

4-amino-2-(1h-pyrazolo[3,4-b]pyridin-3-yl)-6-oxo-6,7-dihydro-5h-pyrrolo[2,3-d]pyrimidine derivatives and the respective (1h-indazol-3-yl) derivatives as cgmp modulators for treating cardiovascular diseasesPublication Number: EP-3394067-B1Priority Date: 2015-12-22Grant Date: 2020-04-01
Soluble guanylate cyclase stimulatorPublication Number: TW-201734017-APriority Date: 2015-12-22
4-Amino-2- (1h-pyrazolo [3,4-b] pyridin-3-yl) -6-oxo-6,7-dihydro-5h-pyrrolo [2,3-d] pyrimidine derivatives and respectively (1h- indazol-3-yl) are derived as cgmp activators for the treatment of cardiovascular diseasePublication Number: IL-260020-APriority Date: 2015-12-22
Soluble guanylate cyclase stimulatorsPublication Number: TW-I724079-BPriority Date: 2015-12-22Grant Date: 2021-04-11
cGMP modulators for the treatment of cardiovascular diseasePublication Number: CN-108738320-BPriority Date: 2015-12-22Grant Date: 2021-11-19
4-Amino-2-(1H-pyrazolo[3,4-b]pyridin-3-yl)-6-oxo-6,7-dihydro- 5H-pyrrolo[2,3-d]pyrimidine derivatives and their respective (1H-indazol-3-yl) derivativesPublication Number: CN-108738320-APriority Date: 2015-12-22
4-amino-2-(1H-pyrazolo[3,4-B]pyridin-3-yl)-6-oxo-6,7-dihydro-5H-pyrrolo[ as a cGMP modulator for the treatment of cardiovascular disease 2,3-D]pyridine derivatives and respective (1H-indazol-3-yl) derivativesPublication Number: KR-102191312-B1Priority Date: 2015-12-22Grant Date: 2020-12-15
Soluble guanylate cyclase stimulatorsPublication Number: US-10030027-B2Priority Date: 2015-12-22Grant Date: 2018-07-24
4-Amino-2- (1H-pyrazolo [3,4-b] pyridin-3-yl) -6-oxo-6,7-dihydro-5H-pyrrolo [2,3-d] pyrimidine derivatives and cardiovascular disease (1H-indazol-3-yl) derivatives as cGMP modulators for treatingPublication Number: JP-2018538333-APriority Date: 2015-12-22
Soluble guanylate cyclase stimulatorsPublication Number: US-2018305366-A1Priority Date: 2015-12-22
Processes for preparing crystalline soluble guanylate cyclase stimulatorsPublication Number: WO-2025006294-A2Priority Date: 2023-06-26
Processes for preparing soluble guanylate cyclase stimulatorsPublication Number: WO-2025006295-A1Priority Date: 2023-06-26
4-Amino-2- (1H-pyrazolo [3,4-b] pyridin-3-yl) -6-oxo-6,7-dihydro-5H-pyrrolo [2,3-d] pyrimidine derivatives and cardiovascular disease (1H-indazol-3-yl) derivatives as cGMP modulators for treatingPublication Number: JP-6454448-B2Priority Date: 2015-12-22Grant Date: 2019-01-16
Soluble guanylate cyclase stimulatorsPublication Number: US-10428076-B2Priority Date: 2015-12-22Grant Date: 2019-10-01
Soluble guanylate cyclase stimulatorsPublication Number: US-2017174693-A1Priority Date: 2015-12-22

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Legal status

Legal status	Investigational
Identifiers
IUPAC name
CAS Number	2101645-33-2
PubChem CID	129242560
ChemSpider	129394387
UNII	6DXN080KGB
ChEMBL	ChEMBL5944803
Chemical and physical data
Formula	C₂₇H₂₂ClF₅N₆O₃
Molar mass	608.95 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

References

Bajwa, Ednan K.; Cislak, Dawn; Palcza, John; Feng, Hwa-ping; Messina, Eric J.; Reynders, Tom; Denef, Jean-François; Corcea, Vasile; Lai, Eseng; Stoch, S. Aubrey (January 2023). “Effects of an inhaled soluble guanylate cyclase (sGC) stimulator MK-5475 in pulmonary arterial hypertension (PAH)”. Respiratory Medicine. 206 107065. doi:10.1016/j.rmed.2022.107065. PMID 36521262.
Patel, Mahesh J.; Bajwa, Ednan K.; Cislak, Dawn; Palcza, John; Reynders, Tom; Barthson, Jenny; Lai, Eseng; Stoch, S. Aubrey (9 September 2023). “A randomized study to evaluate the effects of single-dose MK-5475 co-administered with sildenafil on systemic hemodynamics”. European Respiratory Journal PA1208. doi:10.1183/13993003.congress-2023.PA1208.
El-Kersh, Karim; Jalil, Bilal A. (July 2023). “Pulmonary hypertension inhaled therapies: An updated review”. The American Journal of the Medical Sciences. 366 (1): 3–15. doi:10.1016/j.amjms.2023.03.002. PMID 36921672.
Tawa, Masashi; Okamura, Tomio (August 2022). “Factors influencing the soluble guanylate cyclase heme redox state in blood vessels”. Vascular Pharmacology. 145 107023. doi:10.1016/j.vph.2022.107023. PMID 35718342.

/////////frespaciguat, ANAX, ADVECT, guanylate cyclase activator, MK5475, MK 5475, sGC activator 1, 6DXN080KGB

Fosrolapitant

January 25, 2026 2:35 am / Leave a comment

Fosrolapitant

CAS 2573694-38-7

MF C27H29F6N2O8P MW654.5 g/mol

phosphonooxymethyl (5S,8S)-8-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-2-oxo-8-phenyl-1,9-diazaspiro[4.5]decane-9-carboxylate

(phosphonooxy)methyl (5S,8S)-8-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}methyl)-2-oxo-8-phenyl-1,7-diazaspiro[4.5]decane-7-carboxylate
neurokinin 1 (NK1) receptor antagonist, HR20013, HR 20013, M5QGY92X8B

Fosrolapitant (HR20013) is a novel, intravenous, highly selective neurokinin-1 (NK-1) receptor antagonist used for the prevention of chemotherapy-induced nausea and vomiting (CINV), particularly for cisplatin-based regimens. As a prodrug, it is rapidly converted to rolapitant, offering a long half-life (~180 h). It is often combined with palonosetron and dexamethasone for high efficacy.

Fosrolapitant is a small molecule drug. The usage of the INN stem ‘-pitant’ in the name indicates that Fosrolapitant is a neurokinin NK1 (substance P) receptor antagonist. Fosrolapitant has a monoisotopic molecular weight of 654.16 Da.

Key Aspects of Fosrolapitant:

Mechanism: Acts as an NK-1 receptor antagonist to prevent nausea/vomiting.
Administration: Intravenous (IV) formula, often combined as a fixed-dose with palonosetron (HR20013).
Metabolism: Completely converted to rolapitant in the body, which has a prolonged half-life of approximately 180 hours.
Clinical Efficacy: In trials (e.g., PROFIT trial), it demonstrated high effectiveness in preventing CINV in patients receiving highly emetogenic chemotherapy.
Safety Profile: Common adverse events in trials included constipation (22.7%), increased blood pressure (18.2%), abdominal distension (13.6%), and injection site reactions (9.1%).

Fosrolapitant is designed to improve convenience and patient compliance in managing acute and delayed nausea and vomiting associated with cancer treatments.

HR20013 for Nausea and Vomiting Associated With Moderate Emetic Risk Anticancer Agents

CTID: NCT06554184

Phase: Phase 3

Status: Completed

Date: 2025-11-17

SYN

WO-2020259675-A1

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020259675&_cid=P20-MKT4GS-85082-1

Under N2 protection, compound 3 (1.95 g, 2.543 mmol, 1 eq) dissolved in dichloromethane (40 mL) was added to a 100

_mL single-necked flask. Trifluoroacetic acid (1.45 mL, 19.52 mmol, 8 eq) was slowly added under ice water cooling. The mixture was stirred until the reaction was complete, concentrated, and 2.29 g of oil was obtained. After separation and purification, 1.39 g of white foamy solid was obtained, with a yield of 83.5%.

[0129]

¹H-NMR(400MHz，CD ₃OD):δ(ppm)7.89(s，2H)，7.86(s，1H)，7.41-7.27(m，5H)，5.66(d，J＝12Hz，1H)，5.50-5.47(m，1H)，4.60(d，J＝8Hz，1H)，4.20-3.88(m，3H)，2.51-2.10(m，5H)，1.86-1.66(m，3H)，1.44-1.31(m，4H).

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=US380158929&_cid=P20-MKT480-75882-1

Example 1

STEP 1

Compound 1 (2.43 g, 4.86 mmol, 1 eq) was weighed and dissolved in dichloromethane (36 mL) in a 100 mL three-necked flask under N ₂atmosphere. Diisopropylethylamine (5 g, 38.76 mmol, 8 eq) was added and the mixture was cooled to −30° C. Trimethylchlorosilane (1.36 g, 12.52 mmol, 2.6 eq) was added and the mixture was stirred at room temperature for 2 h. The reaction mixture was cooled to −25° C. A solution of chloromethyl chloroformate (0.77 g, 6 mmol, 1.23 eq) in dichloromethane was added dropwise and the mixture was stirred under controlled temperature at −20° C.˜−5° C. until completion of the reaction. The reaction solution was poured into ice water, put to separation, and extracted with dichloromethane. Water and 1 N hydrochloric acid solution were added and put to separation. The organic layer was then successively washed with brine, saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and concentrated to give 3.0 g yellow jelly with a yield of 104%.

Compound 3 (1.95 g, 2.543 mmol, 1 eq) was added into a 100 mL single-necked flask and dissolved in dichloromethane (40 mL) under N ₂atmosphere. Trifluoroacetic acid (1.45 mL, 19.52 mmol, 8 eq) was added slowly under ice water cooling. The reaction mixture was stirred until completion of the reaction, and then concentrated to give 2.29 g oil which was then purified purified to give 1.39 g white foamy solid with a yield of 83.5%.

¹H-NMR (400 MHz, CD ₃OD): δ(ppm) 7.89 (s, 2H), 7.86 (s, 1H), 7.41-7.27 (m, 5H), 5.66 (d, J=12 Hz, 1H), 5.50-5.47 (m, 1H), 4.60 (d, J=8 Hz, 1H), 4.20-3.88 (m, 3H), 2.51-2.10 (m, 5H), 1.86-1.66 (m, 3H), 1.44-1.31 (m, 4H).

PAT

Use of nk1 antagonist prodrug compound in combination with 5-ht3 receptor antagonistPublication Number: US-2024016822-A1Priority Date: 2020-12-25
Use of nk1 antagonist prodrug compound in combination with 5-ht3 receptor antagonistPublication Number: EP-4268818-A1Priority Date: 2020-12-25
Neurokinin-1 antagonistPublication Number: EP-3991730-A1Priority Date: 2019-06-28
Neurokinin-1 antagonistPublication Number: WO-2020259675-A1Priority Date: 2019-06-28
Neurokinin-1 antagonistsPublication Number: TW-202115064-APriority Date: 2019-06-28

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Evetifator

January 22, 2026 2:35 am / Leave a comment

Evetifator

CAS 2278265-85-1

MF C20H19ClF3N3O4 MW457.8 g/mol

2-(4-chlorophenoxy)-N-[3-[5-[3-(trifluoromethoxy)cyclobutyl]-1,3,4-oxadiazol-2-yl]-1-bicyclo[1.1.1]pentanyl]acetamide

2-(4-chlorophenoxy)-N-(3-{5-[(1s,3s)-3-(trifluoromethoxy)cyclobutyl]-1,3,4-oxadiazol-2-yl}bicyclo [1.1.1]pentan-1-yl)acetamide
eukaryotic translation initiation factor 2B (eIF2B) activator, DNL-343, DNL 343, FYL3Y9D7SK

Evetifator (also known as DNL343) is a potent, selective, and brain-penetrant small molecule activator of eukaryotic initiation factor 2B (eIF2B). As of 2026, it is primarily being investigated for the treatment of neurodegenerative diseases, such as amyotrophic lateral sclerosis (ALS).

Key Characteristics and Function

Mechanism of Action: It acts as an eIF2B activator. eIF2B is a critical regulator of protein synthesis; by activating it, the drug aims to address the Integrated Stress Response (ISR) which, when chronically activated, leads to neurodegeneration.
Pharmacological Profile:
- Potency: It shows an IC50cap I cap C sub 50𝐼𝐶50 of 3.2 nM in cellular reporter assays.
- Brain Penetration: It is specifically designed to cross the blood-brain barrier to target the central nervous system (CNS).

A Study to Evaluate the Bioavailability and Safety of DNL343 in Healthy VolunteersCTID: NCT04581772Phase: Phase 1Status: CompletedDate: 2021-06-11
A Study to Evaluate the Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of DNL343 in Healthy VolunteersCTID: NCT04268784Phase: Phase 1Status: CompletedDate: 2022-02-07
HEALEY ALS Platform Trial – Regimen G DNL343CTID: NCT05842941Phase: Phase 2/Phase 3Status: CompletedDate: 2025-02-04
A Study to Determine the Safety, Pharmacokinetics, and Pharmacodynamics of DNL343 in Participants With Amyotrophic Lateral SclerosisCTID: NCT05006352Phase: Phase 1Status: CompletedDate: 2024-09-19
HEALEY ALS Platform Trial – Master ProtocolCTID: NCT04297683Phase: Phase 2/Phase 3Status: Active, not recruitingDate: 2025-12-31

SYN

WO 2019/032743

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2019032743&_cid=P10-MKOU1U-66006-1

EXAMPLE 3

2-(4-chlorophenoxy)-N-[3-[5-[cis-3-(trifluoromethoxy)cyclobutyl]-1,3,4-oxadiazol-2-yl]-1- bicyclo[1.1.1]pentanyl]acetamide

[0257] 2-(4-chlorophenoxy)-N-[1-(hydrazinecarbonyl)-3-bicyclo[1.1.1]pentanyl]acetamide (200 mg, 0.65 mmol), 3-cis-(trifluoromethoxy)cyclobutanecarboxylic acid (131 mg, 0.71 mmol; 8:1 to 10:1 ratio of cis- to trans-) and triethylamine (NEt₃) (0.45 mL, 3.23 mmol) were dissolved in EtOAc (2.6 mL) and T3P solution (0.58 mL, 1.94 mmol, 50 % in EtOAc) was added. The resulting reaction mixture was heated to 100 °C overnight, cooled to rt and was diluted with sat. aq. NaHCO₃ solution (10 mL) and EtOAc (10 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3 × 10 mL). The combined organic layers were dried over anhydrous MgSO₄, filtered, and concentrated under reduced pressure. The crude reaction mixture was purified employing reverse-phase prep-HPLC to deliver the desired product as a clear oil. ¹H-NMR (400 MHz; CDCl₃): δ 7.33-7.29 (m, 2H), 7.03 (s, 1H), 6.91-6.87 (m, 2H), 4.76-4.69 (m, 1H), 4.44 (s, 2H), 3.39-3.30 (m, 1H), 2.92-2.84 (m, 2H), 2.74-2.68 (m, 2H), 2.67 (s, 6H). LC-MS m/z: = 458.20 [M+H]⁺.

[0258] Alternatively, a mixture of 2-(4-chlorophenoxy)acetic acid (50 mg, 0.27 mmol), 2-(4-chlorophenoxy)acetic acid (50 mg, 0.27 mmol), NEt₃ (123 mg, 1.21 mmol) and T3P (185 mg, 0.29 mmol, 50% purity) in DCM (1 mL) was stirred at 0 °C for 1 h. To the mixture was added 1-[5-[3-cis-(trifluoromethoxy)cyclobutyl]-1,3,4-oxadiazol-2-yl]bicyclo[1.1.1]pentan-3-amine HCl salt (8:1 to 10:1 favoring the cis- diastereomer) (70 mg, 0.24 mmol) at 0 °C. The mixture was stirred at 25 °C for 12 h. To the reaction was added sat. aq. NaHCO₃ (4 mL). The aqueous phase was extracted with DCM (5 mL, 3 mL). The combined organic phase was washed with brine (10 mL), dried with anhydrous Na₂SO₄, filtered and concentrated under reduced pressure to provide the title compound.

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022133236&_cid=P10-MKOTTO-58939-1

2-(4-chlorophenoxy)-N-[3-[5-[cA-3-(trifluoromethoxy)cyclobutyl]-l,3,4-oxadiazol-2-yl]-l-bicyclo[l.l.l]pentanyl]acetamide, designated herein as Compound I, has the following formula:

Example 1. Synthesis of Compound I

2-(4-chlorophenoxy)-/V-[l-(hydrazinecarbonyl)-3-bicyclo[l.l.l]pentanyl]acetamide

[0131] To a suspension of methyl 3-[[2-(4-chlorophenoxy)acetyl]amino]bicyclo[l.l.l]pentane-l-carboxylate (270 mg, 0.87 mmol) in EtOH (0.25-0.1M) was added hydrazine hydrate (131 mg, 2.6 mmol) in EtOH (3.5 mL) and the reaction mixture was heated at 90 °C overnight. The reaction mixture

was cooled to rt often causing the product to crystallize out of solution. This solid was collected by removal of the supernatant. If the product did not crystallize, the solution was concentrated, and the crude product was sufficiently pure to use in subsequent steps.

LC-MS m/z: = 310.1 [M+H]⁺.

2-(4-chlorophenoxy)-N-[3-[5-[cis-3-(trifluoromethoxy)cyclobutyl]-1,3,4-oxadiazol-2-yl]-1-bicyclo[1.1.1]pentanyl]acetamide

[0132] 2-(4-chlorophenoxy)-N-[1-(hydrazinecarbonyl)-3-bicyclo[1.1.1]pentanyl]acetamide (200 mg, 0.65 mmol), 3-cis-(trifluoromethoxy)cyclobutanecarboxylic acid (131 mg, 0.71 mmol; 8:1 to 10:1 ratio of cis- to trans-) and triethylamine (NEt₃) (0.45 mL, 3.23 mmol) were dissolved in EtOAc (2.6 mL) and T3P solution (0.58 mL, 1.94 mmol, 50 % in EtOAc) was added. The resulting reaction mixture was heated to 100 ºC overnight, cooled to rt and was diluted with sat. aq. NaHCO₃ solution (10 mL) and EtOAc (10 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (3 x 10 mL). The combined organic layers were dried over anhydrous MgSO₄, filtered, and concentrated under reduced pressure. The crude reaction mixture was purified employing reverse-phase prep-HPLC to deliver the desired product as a clear oil.¹H-NMR (400 MHz; CDCl₃): δ 7.33-7.29 (m, 2H), 7.03 (s, 1H), 6.91-6.87 (m, 2H), 4.76-4.69 (m, 1H), 4.44 (s, 2H), 3.39-3.30 (m, 1H), 2.92-2.84 (m, 2H), 2.74-2.68 (m, 2H), 2.67 (s, 6H). LC-MS m/z: = 458.20 [M+H]⁺.

[0133] Alternatively, a mixture of 2-(4-chlorophenoxy)acetic acid (50 mg, 0.27 mmol), NEt3 (123 mg, 1.21 mmol) and T3P (185 mg, 0.29 mmol, 50% purity) in DCM (1 mL) was stirred at 0 °C for 1 h. To the mixture was added 1-[5-[3-cis-(trifluoromethoxy)cyclobutyl]-1,3,4-oxadiazol-2-yl]bicyclo[1.1.1]pentan-3-amine HCl salt (8:1 to 10:1 favoring the cis- diastereomer) (70 mg, 0.24 mmol) at 0 °C. The mixture was stirred at 25 °C for 12 h. To the reaction was added sat. aq. NaHCO3 (4 mL). The aqueous phase was extracted with DCM (5 mL, 3 mL). The combined organic phase was washed with brine (10 mL), dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide the title compound.

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2023250107&_cid=P10-MKOTXL-62392-1

Example 14: Preparation of 2-(4-chlorophenoxy)-N-(3-(5-((ls,3s)-3-(trifluoromethoxy)cyclobutyl)- l,3,4-oxadiazol-2-yl)bicyclo[l.l.l]pentan-l-yl)acetamide (I)

[0377] XI- la, 2-(4-chlorophenoxy)acetic acid (XII- la), and 2-MeTHF were charged to a reactor under N2 condition and cooled to 0 ~ 5 °C. TEA was added while maintaining an internal temperature of not more than about 10 °C under N2 condition and rinsed with 2-methyltetrahydrafuran (2-MeTHF). The contents were agitated at about 0 ~ 5 °C for not less than about 20 minutes. Diphenylphosphinic chloride in 2-MeTHF solution is added slowly while maintaining an internal temperature of not more than about 10 °C under N2 condition and rinsed with 2-MeTHF. The contents were warmed to about 20 ~ 25 °C and then agitated for not less than about 1 hour until the reaction was completed. The contents were cooled to about 0 ~ 5 °C and then aqueous 10% K2CO3 was added while maintaining an internal temperature of not more than about 10 °C. After phase separation, the organic layer was successively washed with aqueous 10% K2CO3 and 5% K2CO3. The organic layer was concentrated to a target volume 3 V. 2-MeTHF was added and then the contents were concentrated to a target volume 3 V to control the water content to not more than about 0.3 w/w%. IPA was added and then the contents were heated to about 60 ~ 70 °C to

dissolve all solids. The contents were filtered at about 60 ~ 70 °C through cartridge filter and rinsed with pre-heated IPA (60 ~ 70 °C). The filtrate was concentrated to a target volume 4 V. IPA was added and concentrated to a target volume 4 V to control the residual 2-MeTHF relative to IPA to not more than 1 % by GC. The contents were adjusted to about 20 ~25 °C. n-Heptane was added and then heated to about 60 ~ 80 °C to dissolve all solids. The contents were adjusted to about 62 ~ 70 °C. Seed crystal was charged and agitated for not less than about 0.5 hour. n-Heptane was added while maintaining an internal temperature of about 60 ~ 65 °C. The contents were cooled to about 0 ~ 5 °C over 12 hour (5 °C per hour). The slurry was agitated for not less than 2 hours. The slurry was filtered and washed with precooled IPA/n-heptane mixture. The wet cake was dried at 25 °C under vacuum. If any individual impurity except 2-(4-chlorophenoxy)-N-(3-(5-(trans-3-(trifluoromethoxy)cyclobutyl)-l,3,4-oxadiazol-2-yl)bicyclo[l.l.l]pentan-l-yl)acetamide was more than 0.12%, recrystallization was performed.

[0378] ’H NMR (600 MHz, MeCN-d₃): 7.65 (s, 1H), 7.3

PAT

Compounds, compositions and methodsPublication Number: JP-2023052166-APriority Date: 2017-08-09
Compounds, compositions, and methodsPublication Number: CN-111094233-BPriority Date: 2017-08-09Grant Date: 2024-03-15
Modulators of eukaryotic initiation factor 2B, compositions and methodsPublication Number: US-11236100-B2Priority Date: 2017-08-09Grant Date: 2022-02-01
Compounds, compositions, and methodsPublication Number: CN-118239938-APriority Date: 2017-08-09
Solid forms of a compoundPublication Number: US-2024059662-A1Priority Date: 2020-12-18
Modulators of eukaryotic initiation factor 2B, compositions and methodsPublication Number: US-2022411433-A1Priority Date: 2017-08-09
COMPOUNDS, COMPOSITIONS AND METHODSPublication Number: WO-2019032743-A1Priority Date: 2017-08-09
Modulators of eukaryotic initiation factor 2B, compositions and methodsPublication Number: US-11851440-B2Priority Date: 2017-08-09Grant Date: 2023-12-26
Compounds, compositions and methodsPublication Number: US-2021147435-A1Priority Date: 2017-08-09

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//////evetifator, ANAX, eukaryotic translation initiation factor 2B (eIF2B) activator, DNL-343, DNL 343, FYL3Y9D7SK

Evategrel

January 21, 2026 2:36 am / Leave a comment

Evategrel

CAS 2760609-74-1

MF C21H26ClNO7S MW 472.0 g/mol

(2Z)-2-[(4R)-1-[(1S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]-4-(propan-2-yloxycarbonyloxymethylsulfanyl)piperidin-3-ylidene]acetic acid

(Z)-[(4R)-1-[(1S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]-4-{[({[(propan-2-yl)oxy]carbonyl}oxy)methyl]sulfanyl}piperidin-3-ylidene]acetic acid
platelet aggregation inhibitor, CG-0255, CG 0255, 9FKJ76ZX22

Evategrel (CG-0255) is a promising new antiplatelet drug, a thioether prodrug, designed to improve upon clopidogrel (Plavix) by offering faster action, consistent potency, and overcoming resistance, with both oral and intravenous (IV) formulations available for emergency use. It works by rapidly converting to the same active metabolite as clopidogrel (H4) through simple hydrolysis, bypassing the CYP enzymes that can cause variability and resistance with clopidogrel. Clinical trials show it’s well-tolerated, potent, and has potential to become a superior P2Y12 inhibitor for preventing blood clots in cardiovascular conditions.

Key Features

Fast & Potent: Achieves significant platelet inhibition (IPA) within 15-30 minutes.
Consistent Activation: Relies on liver carboxylesterases, avoiding CYP2C19 variability, leading to less individual response difference.
Dual Formulation: First P2Y12 inhibitor with both IV (for emergencies/surgery) and oral forms.
Overcomes Resistance: Specifically designed to address clopidogrel resistance issues.
Low Drug-Drug Interactions: Expected to have minimal interactions.

How it Works

Prodrug: Evategrel is inactive when administered.
Hydrolysis: Liver esterase enzymes quickly break it down (hydrolyze it) in a single step.
Active Metabolite: This process creates H4, the same active antiplatelet molecule as clopidogrel’s active form.
Platelet Inhibition: H4 blocks the P2Y12 receptor on platelets, preventing them from clumping (aggregating).

Development & Potential

Developed by China-based CureGene.
Shows promise as a “best-in-class” P2Y12 antagonist, potentially benefiting patients with acute coronary syndromes (ACS) or those undergoing PCI (percutaneous coronary intervention).

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2023144782&_cid=P10-MKNELX-27983-1

Synthesis Example 1

Steps 11 and 12. Synthesize la-1 and la-2

The solution of 1–13 (1.8 g, 3.4 mmol) in TFA (10 mL) was stirred at room temperature for 30 minutes. After stirring, the reaction mixture was added to a saturated NaHCO3 _solution (100 mL), followed by collection with EtOAc (100 mL * 3). The combined organic layers were washed with saturated NaHCO3 _, dried over Na2SO4 _, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by reversed-phase column chromatography (C18, CH3CN / _H2O = _80/20 ) to give la (550 mg, 34% yield). la was further purified by chiral column chromatography to give la-1 and la-2.

the:

LC-MS [M+l]+ = 472.1

57.59 (s, 1H), 7.38 (d, J = 4 Hz, 1H), 7.32-7.26 (m, 2H), 5.86 (s, 1H), 5.22 (dd, 12.2, 2.6 Hz, 1H), 5.00-4.83 (m, 3H), 4.50 (dd, J = 66.2, 11.9 Hz, 1H), 3.82 (s, 1H), 3.70 (d, J = 4.9 Hz, 3H), 3.52 (dd, J = 37.9, 12.9 Hz, 1H), 2.92-2.64 (m, 2H), 2.45-2.30 (m, 1 H), 1.95-1.84 (m, 1H), 1.30 ( 6.2 Hz, 6H)_O

la-1：

NMR (400 MHz, CDC1₃) 6 7.65 (s, 1H), 7.46 – 7.43 (m, 1H), 7.33 (dd, J = 6.3, 2.7 Hz, 2H), 5.91 (s, 1H), 5.27 (d, J = 12.3 Hz, 1H), 5.04 – 4.87 (m, 3H), 4.49 (d, J = 13.7 Hz, 1H), 3.88 (s, 1H), 3.75 (s, 3H), 3.58 (d, J = 14.0 Hz, 1H), 2.87 (s, 2H), 2.44 (s, 1H), 1.95 (dd, J = 14.2, 3.3 Hz, 1H), 1.35 (d, J = 6.2 Hz, 6H)_O

la-2:

NMR (400 MHz, CDCh) 5 7.63 (s, 1H), 7.44 (dt, J = 8.2, 3.1 Hz, 1H), 7.35 – 7.31 (m,

2H), 5.92 (s, 1H), 5.25 (d, J = 12.3 Hz, 1H), 5.07 (s, 1H), 4.94 (td, J = 12.5, 6.5 Hz, 2H), 4.68 (d, J = 13.4 Hz, 1H), 3.87 (s, 1H), 3.76 (s, 3H), 3.50 (d, J = 13.4 Hz, 1H), 2.90 (s, 1H), 2.75 (d, J = 12.3 Hz, 1H), 2.44 (s, 1H), 1.96 (d, 7 = 13.2 Hz, 1H), 1.34 (d, J = 6.3 Hz, 6H) =

PAT

Pharmaceutical composition of antiplatelet drug, and use thereofPublication Number: WO-2023144782-A1Priority Date: 2022-01-28
Antiplatelet drugs and uses thereofPublication Number: US-2023295089-A1Priority Date: 2020-07-29

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Emestedastat

January 19, 2026 2:34 am / Leave a comment

Emestedastat

CAS 1346013-80-6

MF C19H19N5O2S MW381.5 g/mol

[(1R,3r,5S)-3-hydroxy-3-(pyrimidin-2-yl)-8-azabicyclo[3.2.1]octan-8-yl][5-(1H-pyrazol-4-yl)thiophen-3-yl]methanone
11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor, UE-2343, UE 2343, 106ELK29GH

Emestedastat (proposed brand name Xanamem; developmental code name UE-2343) is a steroidogenesis inhibitor which is under development for the treatment of major depressive disorder, Alzheimer’s disease, and fragile X syndrome.^[1][2] It specifically acts as a centrally penetrant inhibitor of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) and thereby inhibits the synthesis of the glucocorticoid steroid hormone cortisol.^[1][3][4][2] As of August 2024, emestedastat is in phase 2 clinical trials for major depressive disorder and Alzheimer’s disease and is in the preclinical stage of development for fragile X syndrome.^[1][2] Clinical effectiveness for Alzheimer’s disease has been mixed.^[2] It was originated by the University of Edinburgh and is being developed by Actinogen Medical.^[1]

Phase I MAD, Fed-Fasted, CSF Study of UE2343 in Healthy SubjectsCTID: NCT02616445Phase: Phase 1Status: CompletedDate: 2025-01-22
Effect of 10 mg Xanamem on Dementia Due to Alzheimer’s DiseaseCTID: NCT06125951Phase: Phase 2Status: Active, not recruitingDate: 2025-12-02
A Phase I Study of Oral UE2343 in Healthy SubjectsCTID: NCT01770886Phase: Phase 1Status: CompletedDate: 2013-07-17
Xanamem™ in Healthy Elderly SubjectsCTID: NCT03830762Phase: Phase 1Status: CompletedDate: 2025-01-22

OriginatorUniversity of Edinburgh
DeveloperActinogen Medical
ClassAntidementias; Azabicyclo compounds; Ketones; Pyrazoles; Pyrimidines; Small molecules; Thiophenes
Mechanism of Action11-beta-hydroxysteroid dehydrogenase type 1 inhibitors
Phase II/IIIAlzheimer’s disease
Phase IIMajor depressive disorder
No development reportedFragile X syndrome
15 Sep 2025Meeting similar to that of Type C will be held for Alzheimer’s disease (AD) with European Medicines Agency and subsequently with the UK MHRA and other regulators in 2026
27 Aug 2025Pharmacokinetics data from a phase I pharmacokinetics trial in volunteers released by Actinogen
28 Jul 2025No recent reports of development identified for preclinical development in Fragile-X-syndrome in Australia (PO)

Syn

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022094668&_cid=P20-MKKJLN-11715-1

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021062472&_cid=P20-MKKJLN-11715-1

PAT

medical cognitive therapyPublication Number: CN-114761005-APriority Date: 2019-09-30
Medicinal cognitive treatmentsPublication Number: CA-3152902-A1Priority Date: 2019-09-30
Therapeutic editingPublication Number: AU-2020395113-A1Priority Date: 2019-12-02
Medicinal cognitive treatmentsPublication Number: EP-4037684-A1Priority Date: 2019-09-30
Medicinal cognitive treatmentsPublication Number: US-2023000843-A1Priority Date: 2019-09-30
Medicinal cognitive treatmentsPublication Number: WO-2021062472-A1Priority Date: 2019-09-30
Cognitive pharmacological treatmentPublication Number: JP-2022550221-APriority Date: 2019-09-30

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References

“UE 2343”. AdisInsight. 28 August 2024. Retrieved 9 October 2024.
Seckl J (January 2024). “11β-Hydroxysteroid dehydrogenase and the brain: Not (yet) lost in translation”. Journal of Internal Medicine. 295 (1): 20–37. doi:10.1111/joim.13741. PMID 37941106.
Bachurin SO, Gavrilova SI, Samsonova A, Barreto GE, Aliev G (March 2018). “Mild cognitive impairment due to Alzheimer disease: Contemporary approaches to diagnostics and pharmacological intervention”. Pharmacological Research. 129: 216–226. doi:10.1016/j.phrs.2017.11.021. PMID 29170097.
Canet G, Hernandez C, Zussy C, Chevallier N, Desrumaux C, Givalois L (2019). “Is AD a Stress-Related Disorder? Focus on the HPA Axis and Its Promising Therapeutic Targets”. Frontiers in Aging Neuroscience. 11 269. doi:10.3389/fnagi.2019.00269. PMC 6776918. PMID 31611783.

///////////emestedastat, 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor, UE-2343, UE 2343, 106ELK29GH

Direclidine

January 18, 2026 2:41 am / Leave a comment

Direclidine

CAS 1803346-98-6

MF C19H30N4O2 MW346.5 g/mol

ethyl 2-[4-(2-methylpyrazol-3-yl)piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate

6-Azaspiro[3.4]octane-6-carboxylic acid, 2-[4-(1-methyl-1H-pyrazol-5-yl)-1-piperidinyl]-, ethyl ester, cis-

ethyl (2r,4s)-2-[4-(1-methyl-1H-pyrazol-5-yl)piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate
muscarinic M4 receptor positive allosteric modulator, TXB4V44U24, NBI-1117568, NBI 1117568

Direclidine (INNTooltip International Nonproprietary Name;^[2] developmental code names NBI-1117568, HTL-0016878)^[1] is an investigational antipsychotic drug for schizophrenia^[3] that was out-licensed from Nxera Pharma to Neurocrine Biosciences, a United States-based pharmaceutical company.^[4][1][5] It is an oral small molecule.^[6][7]

Direclidine (NBI-1117568) is an investigational, oral drug in Phase 3 trials for schizophrenia, developed by Neurocrine Biosciences, working as a selective M4 muscarinic receptor agonist to treat psychosis by modulating dopamine indirectly. It’s an innovative small molecule with potential for neuropsychiatric disorders, showing promise in early trials and aiming to offer a new treatment approach beyond traditional antipsychotics.

Key aspects of Direclidine:

Drug Class: Small molecule, muscarinic M4 receptor agonist, antipsychotic.
Mechanism: Acts as a selective agonist for the M4 receptor, which indirectly helps improve dopamine levels, targeting schizophrenia symptoms.
Developer: Originally from Nxera Pharma, licensed to Neurocrine Biosciences.
Status: In Phase 3 clinical trials for schizophrenia.
Significance: Offers a novel mechanism for treating schizophrenia, potentially with fewer side effects than current treatments.
Other Uses: Also being explored for bipolar mania and other neuropsychiatric conditions.

Development Timeline & Data:

Positive Phase 2 data was announced in August 2024, showing promise for its use in schizophrenia.
Topline data from ongoing Phase 3 studies is expected around 2027.

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2015118342&_cid=P20-MKJ4D7-04370-1

Typical procedure for the preparation of piperidines via sodium triacetoxyborohydride reductive amination, Boc-deprotection and ethylcarbamate formation as exemplified by the preparation of Example 1 -7, ethyl 2-[4-(1 -methyl-1 H-imidazol-2-yl)piperidin-1 -yl]-6-aza s p i ro [3.4] octa n e -6 -ca rb oxy late

Example 1-7

4-(1 -Methylimidazol-2-yl)piperidine hydrochloride (0.244 g, 1 .21 mmol) and 6-Boc-2-oxo-6-azaspiro[3,4]octane (0.273 g, 1 .21 mmol) were dissolved in DCM (10 mL) at rt and titanium isopropoxide (0.4 mL, 2.42 mmol) was added. The reaction mixture was stirred at rt for 1 h. The reaction mixture was cooled to -5 °C, then STAB (0.513 g, 2.42 mmol) and acetic acid (27 pL, 480 pmol) were added and the reaction mixture was stirred overnight under nitrogen while warming to rt. The reaction mixture was quenched with the addition of NaHC0₃ (sat aq.) (10 mL) and diluted with DCM then filtered through a pad of celite. The layers were separated and the aqueous layer was extracted with DCM. The combined DCM layers were washed with brine, then dried over MgS0₄. The solvents were removed in vacuo, and the residue was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil 25g , 40-63 μΠΊ, 60 A, 50 mL per min, gradient 1 % to 10% MeOH in DCM]) to give an inseparable mixture of isomers of terf-butyl 2-[4-(1 -methyl-1 H-imidazol-2-yl)piperidine]-6-azaspiro[3.4]octane-6-carboxylate (0.330 g, 72%) as a yellow gum.

LCMS (Method A): m/z 374 (M+H)⁺ (ES*), at 1.68 min, UV inactive.

Terf-butyl 2-[4-(1-methyl-1 H-imidazol-2-yl)piperidine]-6-azaspiro[3.4]octane-6-carboxylate (0.326 g, 0.87 mmol) was dissolved in 4 M hydrogen chloride in dioxane (1 .2 mL, 5.2 mmol). The reaction mixture was stirred at rt for 18 h. The volatiles were then removed in vacuo and the residue dissolved DCM (17 mL) and triethylamine (0.49 mL, 3.49 mmol). Ethyl chloroformate (125 μί, 1.31 mmol) was added dropwise and the solution stirred at rt for 18 h. The mixture was then poured into NaHC0₃ (aq) (75 mL) and DCM (75 mL), extracted (2 x 75 mL) , and the combined DCM extracts washed with brine (20 mL) then dried over MgSO*. After concentration, the residue was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil 25 g, 40-63 μΐη, 60 A, 50 mL per min, gradient 1 % to 10% MeOH in DCM]) to provide ethyl 2-[4-(1 -methyl-1 H-imidazol-2-yl)piperidine]-6-azaspiro[3.4]octane-6-carboxylate as a brown oil as a mixture of diastereomers (0.25 g, 83%). Preparative HPLC was used to separate the diastereomers, using a Phenomenex Gemini-N C18 column, 150 x 21 mm, eluting with 38 to 48% MeCN/H₂0 at 18 mL/min and collecting fractions by monitoring at 218 nm to give ethyl 2-[4-(1 -methyl-1 H-imidazol-2-yl)piperidine]-6-azaspiro[3.4]octane-6-carboxylate, Example 1-7 Isomer 1 , (0.044 g, 15%) as a colourless oil and ethyl 2-[4-(1 -methyl-1 /-/-imidazol-2-yl)piperidine]-6-azaspiro[3.4]octane-6-carboxylate, Example 1 -7 Isomer 2, (0.031 g, 10%) as a colourless oil. The data for Isomer 2 are in Table 3

PAT

Pharmaceutical compoundsPublication Number: EP-4413985-A2Priority Date: 2014-02-06
BICYCLIC AZA COMPOUNDS AS MUSCARINIC RECEPTOR AGONISTSPublication Number: FI-3406609-T3Priority Date: 2014-02-06Grant Date: 2024-09-10
Bicyclic aza compounds as muscarinic receptor agonistsPublication Number: EP-3406609-B1Priority Date: 2014-02-06Grant Date: 2024-06-26
Bicyclic aza compounds as muscarinic m1 receptor agonists.Publication Number: WO-2015118342-A1Priority Date: 2014-02-06
Bicyclic aza compounds as muscarinic m1 receptor and/or m4 receptor agonistsPublication Number: US-2018179184-A1Priority Date: 2014-02-06
Bicyclic aza compounds as muscarinic m1 receptor and/or m4 receptor agonistsPublication Number: US-2017240530-A1Priority Date: 2014-02-06
Bicyclic aza compounds as muscarinic m1 receptor and/or m4 receptorPublication Number: US-2020325118-A1Priority Date: 2014-02-06
Bicyclic aza compounds as muscarinic receptor agonistsPublication Number: ES-2986327-T3Priority Date: 2014-02-06Grant Date: 2024-11-11

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Overview

It is a selective muscarinic acetylcholine M₄ receptor agonist that indirectly modulates dopamine as the basis for its putative improvement of schizophrenia.^[6] In April 2016, the compound was out-licensed from Nxera Pharma to Allergan, an Irish pharmaceutical company, as part of Nxera’s wider muscarinic agonist portfokio. By September 2017, it had advanced to Phase I clinical trial for the indication of “neuropsychiatric symptoms associated with Alzheimer’s disease and other dementias”^[8] Following Allergan’s acquisition by AbbVie, the license was returned to Nxera in January 2021.^[9] In November 2021, the compound was newly out-licensed to Neurocrine Biosciences, a U.S. pharmaceutical company.^[5] It has been under development as a treatment for schizophrenia, and is currently in Phase III clinical trials.^[10]^[11]

History

2016
- April: The rights to develop Nxera Pharma’s muscarinic agonist portfolio, including NBI-1117568 were transferred to Allergan.^[9]
2017
- September: Allergan initiated Phase I clinical trials for NBI-1117568 to treat “neurobehavioral symptoms related to Alzheimer’s disease and other conditions.”^[8]
2021
- January: Allergan returned the rights to its muscarinic agonist portfolio, including, NBI-1117568 to Nxera Pharma.^[9]
- November: The rights for the muscarinic agonist portfolio were then transferred to Neurocrine Biosciences, which took over the development of NBI-1117568.^[5]
2022
- October: Phase II clinical trial of NBI-1117568 for the treatment of adults with schizophrenia was initiated.^[12]
2024
- April: Neurocrine Biosciences announced that NBI-1117568 had met the requirements of long-term preclinical toxicity tests.^[6]
- August: Neurocrine Biosciences released the results of the Phase II clinical trial.^[13]^[11]
2025
- May: Neurocrine Biosciences initiated a Phase III registrational program for NBI-1117568 for the treatment of adults with schizophrenia.^[14]

Clinical trials

Phase II clinical trial

The Phase II clinical trial was conducted in 15 sites across the U.S. with 200 adult patients diagnosed with schizophrenia.^[15] The primary endpoint was assessed by the change in the total score of the Positive and Negative Syndrome Scale (PANSS) after six weeks of treatment. The 20 mg once-daily group showed a statistically significant improvement of 7.5 points compared to the placebo group (improvement of 18.2 points from baseline, p = 0.011, effect size = 0.61).^[16] However, the 40 mg once-daily group, 60 mg once-daily group, and 30 mg twice-daily group did not show statistically significant differences compared to the placebo group (p-values: 40 mg group: 0.282, 60 mg group: 0.189, 30 mg twice-daily group: 0.090).^[16]

Market reaction to phase II clinical trial

With a PANSS improvement of 7.5, NBI-111758 lagged behind xanomeline/trospium (KarXT) (Karuna Therapeutics) with 8.4 and emraclidine (Cerevel Therapeutics) with 12.7, both of which were in clinical trials at the same time. Moreover, the lack of dose-dependency led to disappointment in the stock market.^[17] Neurocrine Biosciences’ share price dropped 19% on the day following the announcement of the Phase II clinical trial results.^[18]

References

“Delving into the Latest Updates on Direclidine with Synapse”. Synapse. 30 June 2025. Retrieved 27 July 2025.
https://cdn.who.int/media/docs/default-source/international-nonproprietary-names-(inn)/pl133.pdf ^{[bare URL PDF]}
Ye N, Wang Q, Li Y, Zhen X (March 2025). “Current emerging therapeutic targets and clinical investigational agents for schizophrenia: Challenges and opportunities”. Medicinal Research Reviews. 45 (2): 755–787. doi:10.1002/med.22086. PMID 39300769.
“HTL 0016878”. AdisInsight. 2 September 2024. Retrieved 21 October 2024.
“ニューロクライン社との統合失調症およびその他の精神神経疾患を対象とした新規ムスカリン受容体作動薬に関するライセンス契約締結のお知らせ” [Announcement of License Agreement with Neurocrine for Novel Muscarinic Receptor Agonist for Schizophrenia and Other Neuropsychiatric Disorders] (in Japanese). PR TIMES. 2021-11-22. Retrieved 2024-09-17.
“ネクセラファーマ株価6.5%高薬候補で毒性試験成功 – 日本経済新聞” [NexThera Pharma shares rise 6.5% as drug candidate passes toxicity test – Nikkei]. 日本経済新聞電子版 (Nikkei Electronic Edition) (in Japanese). 日本経済新聞社 (Nikkei Inc.). 2024-04-17. Retrieved 2024-09-17.
“当社提携先のニューロクライン社が、統合失調症を対象にしたNBI-1117568の第II相臨床試験の開始を発表［そーせいグループ］ | NIKKEI COMPASS – 日本経済新聞” [Our partner Neurocrine, Inc. announces initiation of Phase II clinical trial of NBI-1117568 for schizophrenia [Sosei Group] | NIKKEI COMPASS – Nikkei Newspaper]. 日経コンパス (Nikkei Compass) (in Japanese). 日本経済新聞社 (Nikkei Inc.). 2022-10-28. Retrieved 2024-09-17.
“アルツハイマー病等の主要症状の治療薬として開発中の新薬候補、選択的ムスカリンM4受容体作動薬の第I相臨床試験で最初の被験者への投与を実施” [First subjects dosed in Phase I clinical trial of selective muscarinic M4 receptor agonist, a potential new drug candidate for treating major symptoms of Alzheimer’s disease] (PDF) (in Japanese). ネクセラファーマ（旧そーせいグループ株式会社）. 2017-09-01. Retrieved 2024-09-17.
“ムスカリン作動薬プログラムのグローバルな研究開発権・販売権が返還” [Global R&D and commercial rights to muscarinic agonist program returned]. プレスリリース・ニュースリリース配信シェアNo.1｜PR TIMES (in Japanese). PR Times. 2021-01-05. Retrieved 2024-09-17.
日経バイオテクONLINE (2024-09-02). “ネクセラファーマ、統合失調症治療薬候補 NBI-1117568の第II相臨床試験の良好な結果によりニューロクライン社より35百万米ドルのマイルストンを受領” [Nexella Pharma Receives $35 Million Milestone Payment from Neurocrine Following Positive Results of Phase II Clinical Trial of NBI-1117568, a Potential Treatment for Schizophrenia]. 日経バイオテクONLINE (in Japanese). 日本経済新聞社. Retrieved 2024-09-17.
“ネクセラ—大幅反落、ニューロクラインの株価下落に追随売り | 個別株 – 株探ニュース” [Nexella – Sharp decline, selling follows fall in Neurocrine stock price | Individual stocks – Kabutan News]. kabutan.jp (in Japanese). MINKABU THE INFONOID, Inc. 2024-08-29. Retrieved 2024-09-17.
“当社提携先のニューロクライン社が、統合失調症を対象にしたNBI-1117568の第Ⅱ相臨床試験の開始を発表” [Our Partner Neurocrine Announces Initiation of Phase 2 Clinical Trial of NBI-1117568 for Schizophrenia]. プレスリリース・ニュースリリース配信シェアNo.1｜PR TIMES (in Japanese). PR TIMES. 2022-10-28. Retrieved 2024-09-17.
日経バイオテク (Nikkei Biotech) ONLINE (2024-09-02). “ネクセラファーマ、統合失調症治療薬候補 NBI-1117568の第II相臨床試験の良好な結果によりニューロクライン社より35百万米ドルのマイルストンを受領” [Nexella Pharma Receives $35 Million Milestone Payment from Neurocrine Following Positive Results of Phase II Clinical Trial of NBI-1117568, a Potential Treatment for Schizophrenia]. 日経バイオテクONLINE (in Japanese). 日本経済新聞社. Retrieved 2024-09-17.
“ネクセラファーマの統合失調症薬、最終治験を開始”. 日本経済新聞. 日本経済新聞社. 2025-05-01. Retrieved 2025-05-02.
“Neurocrine Biosciences Initiates Phase 2 Clinical Study Evaluating NBI-1117568 in Adults with Schizophrenia”. ニューロクライン. 2022-10-27. Retrieved 2024-09-17.
“ネクセラファーマ[4565]：ニューロクライン社との提携プログラムである統合失調症治療薬候補NBI-1117568の第2相臨床試験で良好な結果 2024年8月28日(適時開示) ：日経会社情報DIGITAL：日本経済新聞” [Nexella Pharma [4565]: Positive results in Phase 2 clinical trial of NBI-1117568, a candidate for the treatment of schizophrenia, a collaboration program with Neurocrine, Inc. August 28, 2024 (timely disclosure) : Nikkei Company Information DIGITAL: Nikkei Shimbun]. 日本経済新聞電子版 (in Japanese). 日本経済新聞社. Retrieved 2024-09-17.
“Nxera Pharma Official IR Blog 「ニューロクライン社から35百万米ドルのマイルストン受領」” [Received $35 million milestone payment from Neurocrine]. soseiheptares.blogspot.com. ネクセラファーマ. 2024-09-02. Retrieved 2024-09-19.
“Neurocrine Stock Down 19% on Mixed Schizophrenia Study Results”. Zacks Investment Research. Zacks Investment. 2024-08-29. Retrieved 2024-09-17.

Clinical data

Other names	HTL-0016878; NBI-1117568; NBI-568^[1]
Routes of administration	Oral
Drug class	Muscarinic acetylcholine M₄ receptor agonist
Identifiers
IUPAC name
CAS Number	1803346-98-6
PubChem CID	118295270
ChemSpider	133319625
UNII	TXB4V44U24
KEGG	D13221
Chemical and physical data
Formula	C₁₉H₃₀N₄O₂
Molar mass	346.475 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

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/////direclidine, ANAX, BLUE JET, ADVECT, muscarinic M4 receptor positive allosteric modulator, TXB4V44U24, NBI-1117568, NBI 1117568

Brexanolone caprilcerbate

January 12, 2026 2:55 am / Leave a comment

Brexanolone caprilcerbate

CAS 2681264-65-1

MFC48H78O12 MW 847.1 g/mol

1-O-[[(3R,5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonyloxymethyl] 5-O-[1,3-di(octanoyloxy)propan-2-yl] 3-methylpentanedioate

1-[1,3-bis(octanoyloxy)propan-2-yl] 5-[({[(20-oxo-5α-pregnan3α-yl)oxy]carbonyl}oxy)methyl] 3-methylpentanedioate
GABAA receptor positive allosteric modulator, K3KLQ9T6WM, PHASE 2,

Brexanolone caprilcerbate (INNTooltip International Nonproprietary Name; developmental code names LYT-300, SPT-300) is an orally active prodrug of brexanolone (allopregnanolone) which is under development for the treatment of anxiety disorders.^[1][2][3][4] It is a absorbed via the lymphatic system with oral administration.^[5] The drug is being developed by Seaport Therapeutics and PureTech Health.^[1][2] As of January 2025, it is in phase 2 clinical trials.^[1]

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=US335021515&_cid=P22-MKAJEO-33027-1

PAT

Lipid prodrugs of neurosteroidsPublication Number: WO-2021159021-A1Priority Date: 2020-02-05
Lipid prodrugs of neurosteroidsPublication Number: US-2023338552-A1Priority Date: 2020-02-05
Lipid prodrugs of neurosteroidsPublication Number: US-2022395513-A1Priority Date: 2020-02-05
Lipid prodrugs of neurosteroidsPublication Number: US-2021268115-A1Priority Date: 2020-02-05

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References

“Allopregnanolone prodrug”. AdisInsight. 28 January 2025. Retrieved 26 February 2025.
“Delving into the Latest Updates on Brexanolone caprilcerbate with Synapse”. Synapse. 15 February 2025. Retrieved 26 February 2025.
“Proposed INN: List 131 International Nonproprietary Names for Pharmaceutical Substances (INN)” (PDF). WHO Drug Information. 38 (2): 270. 2024. brexanolonum caprilcerbas brexanolone caprilcerbate 1-[1,3-bis(octanoyloxy)propan-2-yl] 5-[({[(20-oxo-5α-pregnan3α-yl)oxy]carbonyl}oxy)methyl] 3-methylpentanedioate GABAA receptor positive allosteric modulator C48H78O12 2681264-65-1
Carlini SV, Osborne LM, Deligiannidis KM (December 2023). “Current pharmacotherapy approaches and novel GABAergic antidepressant development in postpartum depression”. Dialogues in Clinical Neuroscience. 25 (1): 92–100. doi:10.1080/19585969.2023.2262464. PMC 10557560. PMID 37796239.
Alashal N, Hussain N (2025). “Approach to the use of rescue medications in children for prolonged epileptic seizures in the community”. Paediatrics and Child Health. 35 (4): 113–117. doi:10.1016/j.paed.2025.01.004.

Clinical data

Other names	LYT-300; LYT300; SPT-300; SPT300; Allopregnanolone 3-O-caprilcerbate
Routes of administration	Oral^[1]
Drug class	GABA_A receptor positive allosteric modulator; Neurosteroid
Identifiers
IUPAC name
CAS Number	2681264-65-1
PubChem CID	158098654
UNII	K3KLQ9T6WM
Chemical and physical data
Formula	C₄₈H₇₆O₁₂
Molar mass	845.124 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

/////////////Brexanolone caprilcerbate, GABAA receptor positive allosteric modulator, K3KLQ9T6WM, PHASE 2,

Balinatunfib

January 7, 2026 2:58 am / Leave a comment

Balinatunfib

CAS 2248726-53-4

MF C27H24F2N6O2, 502.5 g/mol

(1R,11R)-5-[2-(1-aminocyclobutyl)pyrimidin-5-yl]-18-(difluoromethoxy)-12-methyl-2,9,12-triazapentacyclo[9.8.1.0^2,10.0^3,8.0^14,19]icosa-3(8),4,6,9,14(19),15,17-heptaen-13-one

(7R,14R)-11-[2-(1-AMINOCYCLOBUTYL)-5-PYRIMIDINYL]-1-(DIFLUOROMETHOXY)-6,7-DIHYDRO-6-METHYL-7,14-METHANOBENZIMIDAZO[1,2-B][2,5]BENZODIAZOCIN-5(14H)-ONE

(7R,14R)-11-[2-(1-Aminocyclobutyl)pyrimidin-5-yl]-1-(difluoromethoxy)-6-methyl-6,7-dihydro-7,14-methanobenzimidazo[1,2-b][2,5]benzodiazocin-5(14H)-one

(7R,14R)-11-[2-(1-aminocyclobutyl)pyrimidin-5-yl]-1-(difluoromethoxy)-6-methyl-6,7-dihydro-7,14-methano[1,3]benzimidazo[1,2-b][2,5]benzodiazocin-5(14H)-one
tumor necrosis factor (TNF) signaling inhibitor, SAR441566, SAR 441566, PLY98MAN4C

OriginatorSanofi
ClassAmines; Anti-inflammatories; Antipsoriatics; Antirheumatics; Azabicyclo compounds; Benzimidazoles; Cyclobutanes; Fluorinated hydrocarbons; Heterocyclic compounds with 4 or more rings; Ketones; Phenyl ethers; Pyrimidines; Small molecules
Mechanism of ActionTumour necrosis factor alpha inhibitors
Phase IICrohn’s disease; Psoriasis; Rheumatoid arthritis; Ulcerative colitis
No development reportedInflammation
09 Dec 2025Sanofi plans a phase-I trial (In volunteers) in December 2025 (PO, Tablet), (NCT07272629)
29 Oct 2025Sanofi plans a phase II SPECIFI-IBD-LTS trial for Crohn’s Disease or Ulcerative Colitis ( Treatment-experienced) in unknown location (PO, Tablet) in December 2025 (NCT07222189)
16 Sep 2025Chemical structure information added.
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Balinatunfib (SAR441566) is an experimental drug which acts as a potent small molecule inhibitor of TNF. Rather than blocking TNF receptors, balinatunfib inactivates TNF directly by stabilising an inactive form of the TNF trimer which fails to bind to its target receptors. It is in early stage clinical trials for rheumatoid arthritis and other chronic autoimmune diseases.^[1][2]

SYN

https://www.chemical.ai/blog/humanai-synergy-in-retrosynthetic-analysis-and-route-optimization-of-balinatunfib

PAT

(WO 2016/050975,

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2016050975&_cid=P22-MK3F7M-67505-1

Intermediate 40

(1R,3R)-1-[2-bromo-6-(difluoromethoxy)phenyl]-7-chloro-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazol-3-amine

Intermediate 38 (5 g, 11.64 mmol) was suspended in toluene (22 mL) and cooled to 0°C before addition of diphenylphosphoryl azide (3.4 mL, 15 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.5 mL, 16 mmol). The mixture was allowed to warm up to r.t and stirred for 2 hours and subsequently at 45°C overnight. The reaction mixture was diluted with EtOAc (150 mL) and the organic phase washed with a saturated aqueous solution of ammonium chloride (50 mL) then a saturated solution of aqueous sodium bicarbonate (50 mL), and concentrated in vacuo. The crude residue thus obtained was solubilized in THF (100 mL) and water (10 mL), trimethylphosphine (17.46 mL, 17.46 mmol) was added and the reaction mixture stirred overnight. The mixture was concentrated in vacuo, partitioned between EtOAc (200 mL) and water (150 mL). The organic layer was extracted with 0.2M HCl aq (3 x 200 mL). The combined acid layer was stirred in an ice bath, whilst 10% NaOH solution was added with stirring until pH increased to 10. The stirred was continued for further 15 minutes to complete precipitation. The precipitate was filtered, rinsed with water (20 mL), then dried under suction for 10 minutes before drying under high vacuum overnight to afford 3.92 g (78%) of the title compound as an off white solid. LCMS basic: RT 1.96 min. (ES+) 428/430 (M+H)⁺

EXAMPLE 11

(7R, 14R)-11-chloro-1-(difluoromethoxy)-6,7-dihydro-7,14-methanobenzimidazo[1,2-b][2,5]benzodiazocin-5(14H)-one

Intermediate 40 (3.7 g, 8.6 mmol), activated molecular sieve 4A powder (1.2 g), potassium carbonate (1.5 equiv., 13 mmol) followed by dichloro[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene]palladium(II) (0.04 equiv., 0.35 mmol) were poured into the center of the 100 mL Glass Parr reaction vessel. 3 cycles of vacuum (~20 mmHg) followed by Argon were applied to the closed reactor.

Anhydrous dimethyl sulfoxide (35 mL) was added, followed by phenol 5M in DMSO (1.1 equiv., 9.5 mmol). The solution was degassed by 3 vacuum (~20 mmHg) / argon cycles followed by 3 cycles of vacuum / CO resulting in a final CO pressure of 1 bar.

The mixture was stirred and heated overnight at 100 °C under the CO atmosphere . The reaction was cooled to 30°C, the reactor vessel was opened and EtOAc (40 mL) was added. The resulting mixture was filtered on a pad of Celite, evaporated in vacuo to yield a green oil.

The residue thus obtained was taken up in EtOAc (100 mL) and the organic layer was washed with water, K₂CO₃ (saturated aqueous solution) and brine (saturated aqueous solution). The aqueous layer was then re-extracted with EtOAc (1 x 50 mL). The combined organic layers were dried over MgSO₄, filtered and evaporated to dryness. The obtained green solid (3.65 g), was taken up in EtOAc, the insoluble material was filtered and rinsed with Et₂O to afford 1.06 g (33.1%) of the title compound as a grey solid.

The filtrate can be purified by flash chromatography to provide additional product if required:

LCMS basic: MH+ m/z = 376, RT 1.90 minutes.

¹H NMR (300 MHz, DMSO) δ 9.12 (d, 1 H, J = 6.7 Hz), 8.23 (dd, 1 H, J = 7.0, 2.4 Hz), 7.60 (m, 5 H), 7.20 (dd, 1 H, J = 8.7, 2.1 Hz), 6.29 (d, 1 H, J = 7.1 Hz), 4.87 (dd, 1 H, J = 6.7 Hz, 6.7 Hz), 3.46 (m, 1 H), 2.72 (d, 1 H, J = 13.4 Hz).

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=US283322316&_cid=P22-MK3EWF-57090-1

Intermediate 3

(7R,14R)-11-Chloro-1-(difluoromethoxy)-6-methyl-6,7-dihydro-7,14-methanobenzimidazo[1,2-b][2,5]benzodiazocin-5(14H)-one

To a solution of (7R,14R)-11-chloro-1-(difluoromethoxy)-6,7-dihydro-7,14-methanobenzimidazo[1,2-b][2,5]benzodiazocin-5(14H)-one (WO 2016/050975, Example 11) (10 g, 26.6 mmol) in dry THF (135 mL), cooled to −78° C. under nitrogen, was added potassium bis(trimethylsilyl)amide (1M in THF, 30 mL, 30 mmol) dropwise over 15 minutes. The resulting mixture was stirred at −78° C. for 1 h prior to the addition of iodomethane (2.5 mL, 40 mmol) dropwise over 5 minutes. The reaction mixture was stirred at −78° C. for 1 h, then allowed to warm slowly to ambient temperature overnight. The reaction mixture was poured into saturated aqueous ammonium chloride solution (600 mL) and extracted with EtOAc (2×800 mL). The organic extracts were dried (Na ₂SO ₄), filtered and concentrated in vacuo. Purification by flash chromatography on silica (elution with 5% MeOH/DCM) afforded the title compound (9.12 g, 88%) as a beige solid. δ _H(300 MHz, DMSO-d ₆) 8.33-8.21 (m, 1H), 7.87-7.33 (m, 5H), 7.22 (dd, J 8.7, 2.1 Hz, 1H), 6.23 (d, J 7.1 Hz, 1H), 5.22 (d, J 7.1 Hz, 1H), 3.55-3.41 (m, 1H), 3.33 (s, 3H), 2.81 (d, J 13.8 Hz, 1H). LCMS (ES+) [M+H] ⁺390.0, RT 1.10 minutes (Method 3).

Intermediate 17

tert-Butyl (1-{5-[(7R,14R)-1-(difluoromethoxy)-6-methyl-5-oxo-5,6,7,14-tetrahydro-7,14-methanobenzimidazo[1,2-b][2,5]benzodiazocin-11-yl]pyrimidin-2-yl}cyclobutyl)-carbamate

A flame-dried flask under nitrogen equipped with a reflux condenser was charged with Intermediate 3 (13.3 g, 34.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.61 g, 1.71 mmol), XPhos (1.63 g, 3.43 mmol), bis(pinacolato)diboron (9.85 g, 38.8 mmol) and potassium acetate (8.5 g, 87 mmol), then 1,4-dioxane (136 mL) was added. The resulting mixture was stirred at 100° C. for 22 h before Intermediate 16 (12.3 g, 37.4 mmol) and aqueous tribasic potassium phosphate solution (1.27 mol/L, 40 mL, 50.8 mmol) were added. The reaction mixture was heated under reflux for 3 h before being charged with additional tris(dibenzylideneacetone)dipalladium(0) (500 mg, 0.53 mmol), XPhos (510 mg, 1.07 mmol) and aqueous tribasic potassium phosphate solution (1.27 mol/L, 20 mL, 25.4 mmol). The mixture was stirred for 1 h, then cooled to room temperature, diluted with DCM (600 mL) and washed with brine (400 mL). The aqueous phase was extracted with DCM (500 mL), then the combined organic extracts were passed through a phase separator and concentrated in vacuo. Purification by flash chromatography on silica (elution with 0-5% MeOH/DCM) afforded the title compound (18.0 g, 88%) as an off-white solid. δ _H(400 MHz, CDCl ₃) 8.93 (s, 2H), 8.49 (dd, J8.2, 1.3 Hz, 1H), 7.84 (dd, J8.5, 0.7 Hz, 1H), 7.74-7.63 (m, 1H), 7.48-7.38 (m, 2H), 7.34-7.29 (m, 1H), 6.84 (t, J72.8 Hz, 1H), 6.31 (d, J7.2 Hz, 1H), 5.92 (s, 1H), 5.01 (d, J7.1 Hz, 1H), 3.53 (s, 3H), 3.51-3.43 (m, 1H), 2.90 (d, J 13.6 Hz, 1H), 2.84-2.57 (m, 3H), 2.22-2.07 (m, 3H), 1.43 (s, 9H). LCMS (ES+) [M+H] ⁺603.2, RT 1.25 minutes (Method 3).

EXAMPLE 6

(7R,14R)-11-[2-(1-Aminocyclobutyl)pyrimidin-5-yl]-1-(difluoromethoxy)-6-methyl-6,7-dihydro-7,14-methanobenzimidazo[1,2-b][2,5]benzodiazocin-5(14H)-one

To a solution of Intermediate 17 (18.0 g, 29.9 mmol) in 1,4-dioxane (25 mL) was added 4M hydrochloric acid in 1,4-dioxane (40 mL). The resulting mixture was stirred at room temperature for 1 h, then concentrated in vacuo. The residue was dissolved in water (500 mL) and washed with EtOAc (2×300 mL). The aqueous layer was basified to pH 9 with 2N aqueous sodium hydroxide solution, which resulted in precipitation of a solid. EtOAc (500 mL) was added and the mixture was stirred until all solids had dissolved. The residue was partitioned, then the aqueous layer was further extracted with EtOAc (500 mL). The combined organic layers were dried over Na ₂SO ₄and filtered, then concentrated in vacuo and dried overnight under high vacuum. The foamy residue was suspended in a mixture of diethyl ether and hexane (150 mL), then stirred and shaken vigorously, before being concentrated in vacuo, to afford the title compound (12.4 g, 83%) as a white amorphous solid. δ _H(400 MHz, DMSO-d ₆) 9.05 (s, 2H), 8.32-8.22 (m, 1H), 7.91-7.66 (m, 3H), 7.62 (dd, J8.5, 1.8 Hz, 1H), 7.53-7.46 (m, 2H), 6.31 (d, J7.1 Hz, 1H), 5.26 (d, J 7.2 Hz, 1H), 3.52 (dt, J 14.2, 7.3 Hz, 1H), 3.36 (s, 3H), 2.84 (d, J 13.8 Hz, 1H), 2.63 (dtd, J11.5, 5.6, 2.5 Hz, 2H), 2.38 (s, 2H), 2.16-2.05 (m, 2H), 2.04-1.91 (m, 1H), 1.87-1.73 (m, 1H). LCMS (ES+APCI) [M-NH ₂] ⁻486.0, RT 1.66 minutes (Method 2). LCMS (ES+) [M+H] ⁺503.0, RT 1.71 minutes (Method 1).

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2025008402&_cid=P22-MK3EWF-57090-1

(7R,14R)-1 l-[2-(l-aminocyclobutyl)pyrimidin-5-yl]-l-(difhroromethoxy)-6-methyl-6,7-dihydro-7, 14-methanobenzimidazo[l,2-b][2,5]benzodiazocin-5(14H)-one.

PAT

Fused Pentacyclic Imidazole Derivatives as Modulators of TNF ActivityPublication Number: US-2021252012-A1Priority Date: 2017-04-25
Fused pentacyclic imidazole derivatives as modulators of TNF activityPublication Number: KR-102565132-B1Priority Date: 2017-04-25Grant Date: 2023-08-08
Fused Pentacyclic Imidazole Derivatives as Modulators of TNF ActivityPublication Number: US-2025127795-A1Priority Date: 2017-04-25
Fused pentacyclic imidazole derivatives as modulators of TNF activityPublication Number: CN-110582495-BPriority Date: 2017-04-25Grant Date: 2022-04-01
Fused Pentacyclic Imidazole DerivativesPublication Number: US-2017305932-A1Priority Date: 2014-10-03
Fused pentacyclic imidazole derivatives as modulators of TNF activityPublication Number: CN-110582495-APriority Date: 2017-04-25
Fused Pentacyclic Imidazole Derivatives as Modulators of TNF ActivityPublication Number: US-2023250105-A1Priority Date: 2017-04-25
Fused pentacyclic imidazole derivatives as modulators of TNF activityPublication Number: US-10980814-B2Priority Date: 2017-04-25Grant Date: 2021-04-20
Fused pentacyclic imidazole derivatives as modulators of tnf activityPublication Number: EP-3939980-A1Priority Date: 2017-04-25
Process for preparing fused pentacyclic imidazole derivatives and uses thereof as modulators of tnf activityPublication Number: EP-3939980-B1Priority Date: 2017-04-25Grant Date: 2023-07-26
Preparation of bridged pentacyclic imidazole derivatives as modulators of tnf activity, intermeditates and their preparationPublication Number: WO-2025068505-A1Priority Date: 2023-09-29
DERIVATIVES OF COMBINED PENTACYCLIC IMIDAZOLES AS MODULATORS OF TNF ACTIVITYPublication Number: HR-P20211927-T1Priority Date: 2017-04-25
Fused pentacyclic imidazole derivatives as modulators of tnf activityPublication Number: CA-3058980-A1Priority Date: 2017-04-25
Fused pentacyclic imidazole derivatives as modulators of tnf activityPublication Number: EP-3615534-B1Priority Date: 2017-04-25Grant Date: 2021-09-15
Fused Pentacyclic Imidazole Derivatives as Modulators of TNF ActivityPublication Number: US-2020046723-A1Priority Date: 2017-04-25

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References

Vugler A, O’Connell J, Nguyen MA, Weitz D, Leeuw T, Hickford E, et al. (2022). “An orally available small molecule that targets soluble TNF to deliver anti-TNF biologic-like efficacy in rheumatoid arthritis”. Frontiers in Pharmacology. 13 1037983. doi:10.3389/fphar.2022.1037983. PMC 9709720. PMID 36467083.
Li Y, Ye R, Dai H, Lin J, Cheng Y, Zhou Y, et al. (January 2025). “Exploring TNFR1: from discovery to targeted therapy development”. Journal of Translational Medicine. 23 (1): 71. doi:10.1186/s12967-025-06122-0. PMC 11734553. PMID 39815286.

Identifiers

IUPAC name
CAS Number	2248726-53-4
PubChem CID	132042903
IUPHAR/BPS	13583
ChemSpider	129738176
Chemical and physical data
Formula	C₂₇H₂₄F₂N₆O₂
Molar mass	502.526 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

//////////Balinatunfib, tumor necrosis factor (TNF) signaling inhibitor, SAR441566, SAR 441566, PLY98MAN4C

Amogammadex

January 2, 2026 2:51 am / Leave a comment

Amogammadex

CAS 1309580-40-2

MF C88H136N8O56S8 MW2458.56

(2R)-2-acetamido-3-[[(1S,3S,5S,6S,8S,10S,11S,13S,15S,16S,18S,20S,21S,23S,25S,26S,28S,30S,31S,33S,35S,36S,38S,40S,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R,52R,53R,54R,55R,56R)-10,15,20,25,30,35,40-heptakis[[(2R)-2-acetamido-2-carboxyethyl]sulfanylmethyl]-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecahydroxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.2^3,6.2^8,11.2^13,16.2^18,21.2^23,26.2^28,31.2^33,36]hexapentacontan-5-yl]methylsulfanyl]propanoic acid

L-CYSTEINE, S,S’,S”,S”’,S””,S”””,S”””,S”””’-(6A,6B,6C,6D,6E,6F,6G,6H-OCTADEOXY-.GAMMA.-CYCLODEXTRIN-6A,6B,6C,6D,6E,6F,6G,6H-OCTAYL)OCTAKIS(N-ACETYL-
AMOGAMMADEX [INN]
CYCLOOCTAKIS-(1->4)-(6-S-((2R)-2-ACETAMIDO-2-CARBOXYETHYL)-6-THIO-.ALPHA.-D-GLUCOPYRANOSYL)

cyclooctakis-(1→4)-{6-S-[(2R)-2-acetamido-2-carboxyethyl]-6-thio-α-Dglucopyranosyl}
rocuronium and vecuronium reversal agent, L-CYSTEINE, S,S’,S”,S”’,S””,S”””,S”””,S”””’-(6A,6B,6C,6D,6E,6F,6G,6H-OCTADEOXY-.GAMMA.-CYCLODEXTRIN-6A,6B,6C,6D,6E,6F,6G,6H-OCTAYL)OCTAKIS(N-ACETYL-
AMOGAMMADEX [INN]
CYCLOOCTAKIS-(1->4)-(6-S-((2R)-2-ACETAMIDO-2-CARBOXYETHYL)-6-THIO-.ALPHA.-D-GLUCOPYRANOSYL)

Pat

WO2012068981

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2012068981&_cid=P21-MJW9RG-10499-1

CD-8

Weigh 23.7 g (0.088 mol) of N-acetylcysteine and measure 160 ml of dry DMF. Add both to a dry three-necked flask and stir until completely dissolved. Cool the reaction solution to approximately -10°C in a constant temperature bath. Slowly add 8.81 g of sodium hydride (60%) in portions under argon protection and mechanical stirring, maintaining the temperature below -5°C. After the addition is complete, continue stirring until no more bubbles emerge, then transfer the solution to approximately 5°C and react until no more bubbles emerge (approximately 2-3 hours).

With the temperature controlled at approximately 5°C in an ice bath, add 8.38 g (3.85 mmol) of DMF solution of 6-per-deoxy-6-per-iodo-γ-cyclodextrin to the reaction solution of the fully reacted N-acetylcysteine sodium salt. Under argon protection, mechanically stir to ensure homogeneity and continue stirring for 30 min. Gradually raise the temperature of the reaction solution to 70°C and react for 12 h. Then cool the reaction solution to room temperature, filter, wash the filter cake twice with DMF, and then wash with acetone until triphenylphosphine and triphenyloxyphosphine are removed. Dry under reduced pressure to obtain crude sodium salt. Dissolve the crude sodium salt in glacial acetic acid, and then pass dry hydrogen chloride gas into the solution under ice bath cooling. A white solid precipitates after 20 min. Filter after no more white solid precipitates (approximately 1 h). Dry acetone was gradually added to the filtrate, and a solid precipitated out. The mixture was filtered, and the filter cake was washed with acetone until there was no sour taste. The cake was dried under reduced pressure to obtain 6-per-deoxy-6-per-(N-acetylglycine methyl)thioether-γ-cyclodextrin (CD-8) with a yield of 48%.

Ή NMR spectra of CD-8 in heavy water (D2O ₎ : 52.02 (CH3,m,3H), 2.69,2.44 (CH2,m,2H), 3.02 (CH,m,H), 3.06,2.81 (CH2,m,2H), 3.73 (2CH,m,2H), 4.19 (CH,m,H), 4.74 (CH,m,H), 5.03 (CH,s,H) ppm.

PAT

CN102060941

https://patentscope.wipo.int/search/en/detail.jsf?docId=CN84636898&_cid=P21-MJW9XY-15988-1

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////////amogammadex

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Example 10B

(S)-3-(4-{4-Amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl}phenyl)propanoic acid

Step A—(S)-Methyl 3-(4-{4-Amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl}phenyl)propanoate

Step B—(S)-3-(4-{4-Amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl}phenyl)propanoic acid

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(7R,14R)-11-Chloro-1-(difluoromethoxy)-6-methyl-6,7-dihydro-7,14-methanobenzimidazo[1,2-b][2,5]benzodiazocin-5(14H)-one

tert-Butyl (1-{5-[(7R,14R)-1-(difluoromethoxy)-6-methyl-5-oxo-5,6,7,14-tetrahydro-7,14-methanobenzimidazo[1,2-b][2,5]benzodiazocin-11-yl]pyrimidin-2-yl}cyclobutyl)-carbamate

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