Invention Grant
US09206155B2 Chiral 1-(4-methylphenylmethyl)-5-OXO-{N-[3-T-butoxycarbonyl-aminomethyl)]-piperidin-1-yl-pyrrolidine-2-carboxamides as inhibitors of collagen induced platelet activation and adhesion
有权
手性1-(4-甲基苯基甲基)-5-氧代-N- {N- [3-叔丁氧基羰基 - 氨基甲基)] - 哌啶-1-基 - 吡咯烷-2-甲酰胺作为胶原诱导的血小板活化和粘附抑制剂
- Patent Title: Chiral 1-(4-methylphenylmethyl)-5-OXO-{N-[3-T-butoxycarbonyl-aminomethyl)]-piperidin-1-yl-pyrrolidine-2-carboxamides as inhibitors of collagen induced platelet activation and adhesion
- Patent Title (中): 手性1-(4-甲基苯基甲基)-5-氧代-N- {N- [3-叔丁氧基羰基 - 氨基甲基)] - 哌啶-1-基 - 吡咯烷-2-甲酰胺作为胶原诱导的血小板活化和粘附抑制剂
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Application No.: US13995336Application Date: 2012-01-12
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Publication No.: US09206155B2Publication Date: 2015-12-08
- Inventor: Dinesh Kumar Dikshit , Madhu Dikshit , Tanveer Irshad Siddiqui , Anil Kumar , Rabi Sankar Bhatta , Girish Kumar Jain , Manoj Kumar Barthwal , Ankita Misra , Vivek Khanna , Prem Prakash , Manish Jain , Vishal Singh , Varsha Gupta , Anil Kumar Dwivedi
- Applicant: Dinesh Kumar Dikshit , Madhu Dikshit , Tanveer Irshad Siddiqui , Anil Kumar , Rabi Sankar Bhatta , Girish Kumar Jain , Manoj Kumar Barthwal , Ankita Misra , Vivek Khanna , Prem Prakash , Manish Jain , Vishal Singh , Varsha Gupta , Anil Kumar Dwivedi
- Applicant Address: IN New Delhi
- Assignee: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
- Current Assignee: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
- Current Assignee Address: IN New Delhi
- Agency: Abelman, Frayne & Schwab
- Priority: IN208/DEL/2011 20110131
- International Application: PCT/IN2012/000032 WO 20120112
- International Announcement: WO2012/104866 WO 20120809
- Main IPC: C07D401/06
- IPC: C07D401/06 ; C07B53/00
![Chiral 1-(4-methylphenylmethyl)-5-OXO-{N-[3-T-butoxycarbonyl-aminomethyl)]-piperidin-1-yl-pyrrolidine-2-carboxamides as inhibitors of collagen induced platelet activation and adhesion](/abs-image/US/2015/12/08/US09206155B2/abs.jpg.150x150.jpg)
Abstract:
Chiral 1-(4-methylphenylmethyl)-5-oxo-{N-[(3-t-butoxycarbonyl-aminomethyl)]-piperidin-1-yl}-pyrrolidine-2-carboxamides as inhibitors of collagen induced platelet activation and adhesion The present invention provides chiral (2S)-1-(4-methyl-phenylmethyl)-5-oxo-(3S)—{N-[(3-t-butoxycarbonyl aminomethyl)]-piperidin-1-yl}-pyrrolidine-2-carboxamide, and (2S)-1-(4-methylphenylmethyl)-5-oxo-(3R)—{N-[(3-t-butoxycarbonyl amino methyl)]-piperidin-1-yl}-pyrrolidine-2-carboxamide of formula 6 and 7 respectively. The present invention also relates to use of these moieties as inhibitors of collagen induced platelet adhesion and aggregation mediated through collagen receptors. The present invention provides a process for preparation of chiral carboxamides of formula 6 and 7 using the process which has advantage to avoid any racemization at the a-carboxylic center, during N-alkylation. The reagent LiHMDS is used at low temperatures to furnish methyl N-(p methylphenylmethyl)lpyroglutamate in good chiral purity.
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