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Camibirstat

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Camibirstat

CAS 2671128-05-3

N-{(2S)-1-[(4-{6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]pyridin-2-yl}-1,3-thiazol-2-yl)amino]-3-methoxy-1-oxopropan-2-yl}-1-(methanesulfonyl)-1H-pyrrole-3-carboxamide
ATPase inhibitor, antineoplastic

MW C24H30N6O6S2 MF 562.7 g/mol

  • 1H-Pyrrole-3-carboxamide, N-((1S)-2-((4-(6-((2R,6S)-2,6-dimethyl-4-morpholinyl)-2-pyridinyl)-2-thiazolyl)amino)-1-(methoxymethyl)-2-oxoethyl)-1-(methylsulfonyl)-
  • N-[(2S)-1-[[4-[6-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridin-2-yl]-1,3-thiazol-2-yl]amino]-3-methoxy-1-oxopropan-2-yl]-1-methylsulfonylpyrrole-3-carboxamide
  • FHD 286

Camibirstat is an investigational new drug that is being evaluated for the treatment of cancer. It is a small molecule that acts as a selective inhibitor of SMARCA2 and SMARCA4, which are key components of the SWI/SNF chromatin remodeling complex.[1]

It is being developed by Foghorn Therapeutics.[2]

Camibirstat is an orally bioavailable, allosteric, small molecule inhibitor of transcription activator BRG1 (SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A member 4; SMARCA4) and BRM (SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A member 2; SMARCA2), with potential antineoplastic activity. Upon oral administration, camibirstat targets, binds to, and inhibits the activity of BRG1 and/or BRM, the primary ATPase components and mutually exclusive subunits of the BRG1/BRM-associated factor (BAF) complexes. This may lead to the inhibition of the SWI/SNF chromatin remodeling complex, disrupt chromatin remodeling and gene expression, and result in the downregulation of oncogenic pathways and the inhibition of tumor cell proliferation. BAF is an important regulator of transcriptional programs and gene expression. Mutations in BAF or its transcription factor partners are found in certain diseases including cancers.

PAT

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=US331910582&_cid=P11-MG1TKU-39131-1

Example 1. Preparation of N—((S)-1-((4-(6-(cis-2,6-dimethylmorpholino)pyridin-2-yl)thiazol-2-yl)amino)-3-methoxy-1-oxopropan-2-yl)-1-(methylsulfonyl)-1H-pyrrole-3-carboxamide

      N—((S)-1-((4-(6-(cis-2,6-dimethylmorpholino)pyridin-2-yl)thiazol-2-yl)amino)-3-methoxy-1-oxopropan-2-yl)-1-(methylsulfonyl)-1H-pyrrole-3-carboxamide was synthesized as shown in Scheme 1 below.

Step 7: Preparation of N—((S)-1-((4-(6-(cis-2,6-dimethylmorpholino)pyridin-2-yl)thiazol-2-yl)amino)-3-methoxy-1-oxopropan-2-O-1-(methylsulfonyl)-1H-pyrrole-3-carboxamide

   To a solution of 1-methylsulfonylpyrrole-3-carboxylic acid (Intermediate K) (2.43 g, 12.9 mmol), EDCI (2.69 g, 14.0 mmol), HOBt (1.89 g, 14.0 mmol), and DIPEA (10.2 mL, 58.4 mmol) in dichloromethane (50 mL) was added Intermediate J (5.00 g, 11.7 mmol). After stirring at room temperature for 4 h, the reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed three times with saturated aqueous NH 4Cl, once with brine, dried over Na 2SO 4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=1:1 to 1:2). The residue was triturated with methyl tert-butyl ether. After 0.5 h, the suspension was filtered, the filter cake was washed with methyl tert-butyl ether, and dried in vacuo. The solid was dissolved in dimethyl sulfoxide (12 mL) and added dropwise to water (800 mL). The suspension was filtered to give wet filter cake. The filter cake was suspended in water and stirred at room temperature. After 1 hour, the solid was collected by filtration, washed three times with water and dried in vacuo to give N—((S)-1-((4-(6-(cis-2,6-dimethylmorpholino)pyridin-2-yl)thiazol-2-yl)amino)-3-methoxy-1-oxopropan-2-yl)-1-(methylsulfonyl)-1H-pyrrole-3-carboxamide (3.9 g, 6.93 mmol, 59.3% yield) as a white solid.
      LCMS (ESI) m/z: [M+H] +=563.1.
       1H NMR (400 MHz, DMSO-d6) δ 12.49 (br s, 1H), 8.51 (d, J=7.2 Hz, 1H), 7.98-7.97 (m, 1H), 7.78 (s, 1H), 7.67-7.57 (m, 1H), 7.29-7.27 (m, 1H), 7.26 (d, J=7.2 Hz, 1H), 6.88-6.74 (m, 2H), 4.94-4.91 (m, 1H), 4.25 (d, J=11.6 Hz, 2H), 3.77-3.67 (m, 2H), 3.63-3.62 (m, 2H), 3.57 (s, 3H), 3.31 (s, 3H), 2.44-2.38 (m, 2H), 1.18 (d, J=6.0 Hz, 6H).

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Clinical data
Other namesFHD286
Identifiers
IUPAC name
CAS Number2671128-05-3
PubChem CID156818030
ChemSpider115010237
UNIIQHA5XLA4SA
ChEMBLChEMBL5095181
Chemical and physical data
FormulaC24H30N6O6S2
Molar mass562.66 g·mol−1
3D model (JSmol)Interactive image
SMILES
InChI

References

  1.  Yu L, Wu D (July 2024). “SMARCA2 and SMARCA4 Participate in DNA Damage Repair”. Frontiers in Bioscience (Landmark Edition). 29 (7): 262. doi:10.31083/j.fbl2907262. PMID 39082357.
  2.  “Camibirstat”. PatSnap.

/////////////Camibirstat, ATPase inhibitor, antineoplastic, Foghorn Therapeutics, FHD 286

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA, ROW2TECH, NIPER-G, Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, Govt. of India as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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