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Larubrilstat

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Larubrilstat

CAS 2765226-31-9

MF C21H25N5O2 MW379.5 g/mol

[2-[[(5R)-6,7-dihydro-5H-cyclopenta[b]pyridin-5-yl]amino]pyrimidin-5-yl]-(8-oxa-2-azaspiro[4.5]decan-2-yl)methanone

(2-{[(5R)-6,7-dihydro-5H-cyclopenta[b]pyridin-5-yl]amino}pyrimidin-5-yl)(8-oxa-2-azaspiro[4.5]decan-2-
yl)methanone
vascular non-inflammatory molecule-1 (VNN1) inhibitor, AG6K4Y29B4

Larubrilstat is the International Nonproprietary Name (INN) for an experimental, small-molecule vascular non-inflammatory molecule-1 (VNN1) inhibitor. VNN1, also commonly known as Vanin-1 or pantetheinase, is an enzyme involved in tissue response to oxidative stress and inflammation.

Current Status

  • Development Context: Larubrilstat is a designated compound linked to therapeutic exploration in inflammatory pathways. Research and patent filings, such as those cataloged by the IUPHAR/BPS Guide to PHARMACOLOGY, track its evaluation alongside similar Vanin-1 inhibitors

SYN

US20240083873,

https://patentscope.wipo.int/search/en/detail.jsf?docId=US425298584&_cid=P20-MQHGA8-93141-1

COMP 2-1 IS PRODUCT

Example 2: Synthesis of Compound 2, Compound 2-1 and Compound 2-2

Step 1
      To a solution of compound 2a (500 mg) in ethanol/water (v/v=4:1, 10 mL) mixed solvent was added successively sodium acetate (740 mg) and hydroxylamine hydrochloride (630 mg). The resulting reaction mixture was heated to 94° C. and stirred continuously for 2 hours. The reaction was completed. The reaction mixture was cooled, added with water (50 mL), and then extracted with ethyl acetate (30 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product of compound 2b (500 mg).

Step 2

      To a solution of compound 2b (320 mg) in acetic acid (6 mL) was added zinc powder (421 mg) in batches. The resulting reaction mixture was heated to 70° C. and stirred continuously for 2 hours. The reaction was completed. The mixture was cooled, filtered and concentrated. The reaction mixture was added with NaOH aqueous solution (10%) to adjust the pH to 9, and then extracted with ethyl acetate (20 mL×4). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product of compound 2c (100 mg).

Step 3

      Compound 2 (66 mg) was obtained from compound if (168 mg) and compound 2c (100 mg) according to the method of Example 1.
       1H NMR (400 MHz, MeOH-d 4) δ 8.58 (s, 2H), 8.35 (d, J=4.69 Hz, 1H), 7.78-7.70 (m, 1H), 7.27-7.18 (m, 1H), 5.71 (t, J=7.15 Hz, 1H), 3.80-3.59 (m, 6H), 3.54 (d, J=20.77 Hz, 2H), 3.13 (ddd, J=16.55, 9.14, 3.68 Hz, 1H), 3.00 (td, J=16.84, 8.51 Hz, 1H), 2.67 (ddd, J=16.06, 8.24, 3.91 Hz, 1H), 2.14-1.99 (m, 1H), 1.93 (dd, J=16.94, 7.33 Hz, 2H), 1.72-1.51 (m, 4H).
      LCMS (ESI), [M+H] +=380.3
      Two enantiomers 2-1 (retention time: 8.483 min) and 2-2 (retention time: 13.580 min) were obtained by chiral separation of compound 2.
      The chromatographic conditions are as follows:chromatographic column: CHIRALPAK AD-H (5 μm, 4.6×250 mm)flow rate: 0.4 mL/minwavelength: 254 nmcolumn temperature: 35° C.mobile phase: A: n-hexane, B: isopropanol, A:B=1:4run time: 50 min
Preparation Method of Compound 2-1

Step 4: Preparation of Compound 2-1

      Compound 2-1e (284 g, 1.375 mol), compound 2-1f (350 g, 1.25 mol) and K 2CO 3 (862.5 g, 6.25 mol) were dissolved in isopropanol, and the reaction mixture was heated at reflux overnight. After the reaction was completed, the reaction mixture was cooled to room temperature. The reaction system was distilled under reduced pressure to remove the solvent, added with dichloromethane, stirred, and filtered. The filtrate was dissolved in 2 N HCl, and the pH of the aqueous phase was adjusted to 8 to 9 by adding 1 N NaOH. The mixture was extracted with dichloromethane, dried and concentrated to obtain compound 2-1.
       1H NMR (400 MHz, CD 3OD) δ 8.58 (s, 2H), 8.37 (d, J=5.1 Hz, 1H), 7.77 (s, 1H), 7.26 (d, J=2.5 Hz, 1H), 5.72 (t, J=7.7 Hz, 1H), 4.53 (s, 2H), 3.80-3.58 (m, 7H), 3.54 (d, J=18.8 Hz, 2H), 3.15 (ddd, J=16.9, 9.2, 3.7 Hz, 1H), 3.02 (dt, J=16.8, 8.5 Hz, 1H), 2.68 (dq, J=12.8, 4.4 Hz, 1H), 2.14-2.02 (m, 1H), 1.93 (q, J=8.1 Hz, 2H), 1.67 (d, J=5.8 Hz, 2H), 1.59 (d, J=5.7 Hz, 2H).
      The absolute stereochemical configuration of compound 2-1 was determined by comparative determination of the above preparation method of the chiral compounds.

PAT

https://patentscope.wipo.int/search/en/detail.jsf;jsessionid=28F257EBC3EA6EE7D447E4442C7CC489.wapp2nA?docId=US458059800&_cid=P20-MQHG5H-85832-1

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PAT

////////larubrilstat, ANAX LABS, vascular non-inflammatory molecule-1 (VNN1) inhibitor, AG6K4Y29B4

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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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