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1. WO2010032264 - IMPROVED PROCESS FOR PREPARATION OF (2R)-4-OXO-4-[3- (TRIFLUOROMETHYL)-5,6-DIHYDRO [1,2,4]-TRIAZOLO[4,3-A]PYRAZIN- 7(8H)-YL]-L-(2,4,5-TRIFLUOROPHENYL)BUTAN-2-AMINE & NEW IMPURITIES IN PREPARATION THEREOF

Publication Number WO/2010/032264
Publication Date 25.03.2010
International Application No. PCT/IN2009/000470
International Filing Date 26.08.2009
Chapter 2 Demand Filed 08.03.2010
IPC
C07D 487/04 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
487Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/-C07D477/183
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
CPC
C07D 487/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
487Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
Applicants
  • CADILA HEALTHCARE LIMITED (AllExceptUS)
  • KOTHARI, Himanshu, Madhusudan [IN]/[IN] (UsOnly)
  • DAVE, Mayank, Ghanshyambhai [IN]/[IN] (UsOnly)
  • PANDEY, Bipin [IN]/[IN] (UsOnly)
  • SHUKLA, Bhavin, Shriprasad [IN]/[IN] (UsOnly)
Inventors
  • KOTHARI, Himanshu, Madhusudan
  • DAVE, Mayank, Ghanshyambhai
  • PANDEY, Bipin
  • SHUKLA, Bhavin, Shriprasad
Agents
  • SUBRAMANIAM, Hariharan
Priority Data
1798/MUM/200827.08.2008IN
188/MUM/200902.02.2009IN
785/MUM/200930.03.2009IN
Publication Language English (en)
Filing Language English (EN)
Designated States
Title
(EN) IMPROVED PROCESS FOR PREPARATION OF (2R)-4-OXO-4-[3- (TRIFLUOROMETHYL)-5,6-DIHYDRO [1,2,4]-TRIAZOLO[4,3-A]PYRAZIN- 7(8H)-YL]-L-(2,4,5-TRIFLUOROPHENYL)BUTAN-2-AMINE & NEW IMPURITIES IN PREPARATION THEREOF
(FR) PROCÉDÉ AMÉLIORÉ DE PRÉPARATION DE (2R)-4-OXO-4-[3-(TRIFLUOROMÉTHYL)-5,6-DIHYDRO[1,2,4]-TRIAZOLO [4,3-A]PYRAZIN-7(8H)-YL]-1-(2,4,4-TRIFLUOROPHÉNYL)BUTAN-2-AMINE ET NOUVELLES IMPURETÉS PRÉSENTES LORS DE SA PRÉPARATION
Abstract
(EN) The present invention relates to synthesis of β-amino acid derivatives of formula (I) and its salts of formula (Ia) by a novel process. The process comprises the reduction of a protected or unprotected prochiral β-amino acrylic acid or derivative there of, by using borane containing reducing agents at atmospheric pressure. The resulting racemic β-amino compound is resolved to a pure stereoisomer of formula (I), specifically to (2R)-4-oxo-4- [3-Ctrifluoromethyl)-5, 6-dihydrol [1,2,4]triazolo [4,3-alpyrazin-7(8H)-yl]-1-(2,4,4-trifluorophenyl)butan-2-amine. In an embodiment the invention disclosed polymorphic forms of formula (I), phosphate salt of formula (I) and also a Dibenzoyl-L-tartaric acid salt of formula (I).
(FR) La présente invention concerne la synthèse de dérivés d'acides aminés β de formule (I) et de leurs sels de formule (Ia) par un nouveau procédé. Le procédé comprend la réduction d'un acide β-aminoacrylique prochiral protégé ou non protégé ou d'un de ses dérivés en utilisant des agents réducteurs contenant du borane à pression atmosphérique. Le composé β-amino racémique obtenu est séparé en un stéréo-isomère pur de formule (I), spécifiquement la (2R)-4-oxo-4-[3-(trifluorométhyl)-5,6-dihydro[1,2,4]-triazolo [4,3-a]pyrazin-7(8H)-yl]-1-(2,4,4-trifluorophényl)butan-2-amine. Dans un mode de réalisation, l'invention concerne des formes polymorphes de formule (I), un sel de phosphate de formule (I) et également un sel d'acide dibenzoyl-L-tartrique de formule (I).
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