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Igermetostat

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Igermetostat Structure
Igermetostat.png

Igermetostat

C32H46N4O4. 550.73

2409538-60-7

2KES6YSH8D

INN 12655

BENZAMIDE, N-((1,2-DIHYDRO-4,6-DIMETHYL-2-OXO-3-PYRIDINYL)METHYL)-3-(ETHYL(TETRAHYDRO-2H-PYRAN-4-YL)AMINO)-2-METHYL-5-((TRANS-3-(1-PIPERIDINYL)CYCLOBUTYL)OXY)-
IGERMETOSTAT
IGERMETOSTAT [INN]
N-((1,2-DIHYDRO-4,6-DIMETHYL-2-OXO-3-PYRIDINYL)METHYL)-3-(ETHYL(TETRAHYDRO-2H-PYRAN-4-YL)AMINO)-2-METHYL-5-((TRANS-3-(1-PIPERIDINYL)CYCLOBUTYL)OXY)BENZAMIDE
N-((4,6-DIMETHYL-2-OXO-1,2-DIHYDROPYRIDIN-3-YL)METHYL)-3-(ETHYL(OXAN-4-YL)AMINO)-2-METHYL-5-(((1R,3R)-3-(PIPERIDIN-1-YL)CYCLOBUTYL)OXY)BENZAMIDE

IGERMETOSTAT is a small molecule drug with a maximum clinical trial phase of II and has 1 investigational indication.

SCHEME

.

PATENT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020020374&_cid=P22-LR1SQG-34075-1

PATENT

US20230382898

https://patentscope.wipo.int/search/en/detail.jsf?docId=US415363922&_cid=P22-LR1S46-25135-1

The compound has been disclosed in patent WO2020020374A1. It is an enhancer of Zeste homolog 2 (EZH2) inhibitor, and can be used for preventing or treating EZH2-mediated diseases, including brain cancer, thyroid cancer, cardiac sarcoma, lung cancer, oral cancer, stomach cancer and various other cancers.

PATENT

US20210308141

https://patentscope.wipo.int/search/en/detail.jsf?docId=US338556625&_cid=P22-LR1S8P-27079-1

Example 4: Preparation of the Compound N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methyl-5-(trans-3-morpholinylcyclobutoxy)benzamide (4)


(MOL)(CDX)
      The title compound was prepared by referring to Example 1 with cyclobutanol replaced by cis-3-morpholinylcyclobutyl-1-ol. The cis-3-morpholinylcyclobutyl-1-ol was prepared as follows:
      3-benzyloxy-cyclobutyl-1-one (3 g, 17 mmol, 1 eq) and morpholine (2.97 g, 34 mmol, 2 eq) were dissolved in DCE (30 mL). After stirring at room temperature for 0.5 h, the solution was added with NaBH(OAc)3 (7.23 g, 34 mmol, 2 eq) and stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure to remove the solvent, adjusted to basicity with aqueous NaHCO3 solution, and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a crude product, which was purified by a phase preparative column to give 4-(3-(benzyloxy)cyclobutyl)morpholine (2.9 g). M/z (ES+), [M+H] +=248.
      4-(3-(benzyloxy)cyclobutyl)morpholine (2.9 g, 117.4 mmol) and methane sulfonic acid (20 mL) was added to dichloromethane (40 mL). The mixture was stirred overnight at room temperature and concentrated under reduced pressure to remove the solvent to give a crude product, which was purified by a preparative column to give cis-3-morpholinylcyclobutyl-1-ol; m/z (ES+), [M+H] +=158. The trans-3-morpholinylcyclobutyl-1-ol can also be separated and obtained by this method.
      m/z (ES +), [M+H] +=553; HPLC t R=1.296 min. 1H NMR (400 MHz, DMSO-d 6) δ 11.53-11.42 (s, 1H), 8.08-8.00 (s, 1H), 6.63-6.58 (d, J=2.4 Hz, 1H), 6.44-6.38 (d, J=2.5 Hz, 1H), 5.89-5.84 (s, 1H), 4.28-4.22 (d, J=4.7 Hz, 2H), 3.63-3.57 (d, J=4.0 Hz, 4H), 3.29-3.17 (t, J=10.5 Hz, OH), 3.02-2.87 (m, OH), 2.39-2.25 (d, J=19.9 Hz, 6H), 2.22-2.17 (s, 3H), 2.15-2.03 (d, J=2.9 Hz, 8H), 1.67-1.57 (d, J=10.7 Hz, 2H), 1.53-1.42 (d, J=8.4 Hz, 2H), 0.82-0.76 (t, J=6.9 Hz, 3H). No isomerization was found in chiral HPLC.

[1]. Peng, et al. Polysubstituted benzene compound and preparation method and use thereof.

World Intellectual Property Organization, WO2020020374 A1. 2020-01-30.

//////////Igermetostat

CCN(C1CCOCC1)c2cc(O[C@H]3C[C@@H](C3)N4CCCCC4)cc(C(=O)NCc5c(C)cc(C)[nH]c5=O)c2C

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DR ANTHONY CRASTO

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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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