Enzymatic resolution of 1-amino-2-vinylcyclopropyl caboxylic acid methyl ester

• US 6,268,207 B1
• Filed: 09/12/2000
• Issued: 07/31/2001
• Est. Priority Date: 08/10/1998
• Status: Expired due to Term

• Current Assignee: Boehringer Ingelheim Limited (C.H. Boehringer Sohn AG & Co. KG)
• Original Assignee: Boehringer Ingelheim Limited (C.H. Boehringer Sohn AG & Co. KG)
• Inventors: Bailey, Murray D.
• Primary Examiner(s): Oswecki, Jane C.
• Application Number:
  US09/660,030
• Time in Patent Office: 322 Days
• Field of Search: 560/125, 560/128, 435/280
• US Class Current: 435/280
• CPC Class Codes: A61K 2300/00 Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
• CPC Class Codes: A61K 38/21 Interferons [IFN]
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61P 1/16 for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 31/14 for RNA viruses
• CPC Class Codes: A61P 31/16 for influenza or rhinoviruses
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 207/16 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 403/14 containing three or more hetero rings
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: C07D 417/14 containing three or more hetero rings
• CPC Class Codes: C07K 5/0806 the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
• CPC Class Codes: C07K 5/0808 the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
• CPC Class Codes: C07K 5/081 the side chain containing O or S as heteroatoms, e.g. Cys, Ser
• CPC Class Codes: C07K 5/0812 and aromatic or cycloaliphatic
• CPC Class Codes: C12P 13/02 Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes peptides C12P21/00 or C07K
• CPC Class Codes: C12P 41/005 : by esterification of carboxylic acid groups in the enantiomers or the inverse reaction

Abstract

An enantiomeric-resolving process for obtaining (1R,2S)-1-amino-2-vinylcyclopropyl carboxylic acid methyl ester by use of an esterase, and especially Alcalase®, is disclosed.

Claims

1. A process for the resolution of enantiomers from a mixture of (1R,2S)/(1S,2S)-1-amino-2-vinylcyclopropyl carboxylic acid methyl ester, comprising the step of treating said mixture with an esterase to obtain the corresponding (1R,2S) enantiomer.

2. A process according to claim 1, wherein said esterase is Alcalase®

.