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

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
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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