NZ336376A - Enzymatic resolution of benzodiazepine-acetic acid esters (3-oxo-2,3,4,5-1H-tetrahydro-1,4-benzodiazepine-2-acetic acid) with a lipase from Candida Antarctica - Google Patents

Enzymatic resolution of benzodiazepine-acetic acid esters (3-oxo-2,3,4,5-1H-tetrahydro-1,4-benzodiazepine-2-acetic acid) with a lipase from Candida Antarctica

Info

Publication number
NZ336376A
NZ336376A NZ336376A NZ33637697A NZ336376A NZ 336376 A NZ336376 A NZ 336376A NZ 336376 A NZ336376 A NZ 336376A NZ 33637697 A NZ33637697 A NZ 33637697A NZ 336376 A NZ336376 A NZ 336376A
Authority
NZ
New Zealand
Prior art keywords
benzodiazepine
acetic acid
tetrahydro
oxo
lipase
Prior art date
Application number
NZ336376A
Inventor
Andrew Stephen Wells
Original Assignee
Smithkline Beecham P
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Smithkline Beecham P filed Critical Smithkline Beecham P
Publication of NZ336376A publication Critical patent/NZ336376A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/16—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
    • C12P17/165—Heterorings having nitrogen atoms as the only ring heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction

Abstract

A process for preparing a compound of the formula (I): wherein X is H, halogen, CO2R3, OR4, COR5, or a fibrinogen or vitronectin antagonist side chain; R2 is C1-6alkyl, optionally substituted by Ar, Het or C1-6cycloalkyl; R3 is C1-6alkyl or benzyl; R4 is Cl-6alkyl, COR3 or benzyl; R5 is 4,4'-bipiperidin-1-yl, (1' -benzyloxycarbonyl)-4 ,4' -bipiiperidin-l-yl, or (l'-t- butoxycarbonyl)-4,4'-bipiperidin-1 -yl; which comprises: a) treating a compound of the formula (II): wherein R1 is C1-20alkyl or C3-20alkenyl, optionally substituted by Ar, NR2 or NR3+, wherein R is C1-4alkyl; with Candida Antarctica lipase B; b) and separating the resulting 2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2- acetic acid carboxylic acid from the corresponding ester.
NZ336376A 1996-12-27 1997-12-23 Enzymatic resolution of benzodiazepine-acetic acid esters (3-oxo-2,3,4,5-1H-tetrahydro-1,4-benzodiazepine-2-acetic acid) with a lipase from Candida Antarctica NZ336376A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3385396P 1996-12-27 1996-12-27
PCT/GB1997/003522 WO1998029561A1 (en) 1996-12-27 1997-12-23 Enzymatic resolution of benzodiazepine-acetic acid esters with a lipase

Publications (1)

Publication Number Publication Date
NZ336376A true NZ336376A (en) 2000-11-24

Family

ID=21872833

Family Applications (1)

Application Number Title Priority Date Filing Date
NZ336376A NZ336376A (en) 1996-12-27 1997-12-23 Enzymatic resolution of benzodiazepine-acetic acid esters (3-oxo-2,3,4,5-1H-tetrahydro-1,4-benzodiazepine-2-acetic acid) with a lipase from Candida Antarctica

Country Status (17)

Country Link
EP (1) EP0964928A1 (en)
JP (1) JP2001507231A (en)
KR (1) KR20000069705A (en)
CN (1) CN1246157A (en)
AR (1) AR010860A1 (en)
AU (1) AU730064B2 (en)
BR (1) BR9714099A (en)
CA (1) CA2276134A1 (en)
CO (1) CO4930272A1 (en)
HU (1) HUP0002825A3 (en)
IL (1) IL130580A0 (en)
NO (1) NO993174D0 (en)
NZ (1) NZ336376A (en)
PL (1) PL334293A1 (en)
TR (1) TR199901487T2 (en)
WO (1) WO1998029561A1 (en)
ZA (1) ZA9711566B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE258604T1 (en) * 1998-02-17 2004-02-15 Searle & Co METHOD FOR THE ENZYMATIC DISSOLUTION OF LACTAMS
KR100378741B1 (en) * 2000-06-01 2003-04-07 에스케이 주식회사 Method for preparing R- or S-form α-substituted heterocyclic carboxyl acid and counter enantiomeric form of α-substituted heterocyclic carboxyl acid ester thereto using enzyme
CA2410438A1 (en) * 2000-06-01 2001-12-06 Sk Corporation Method for optically resolving a racemic alpha-substituted heterocyclic carboxylic acid using enzyme
KR100379756B1 (en) * 2000-10-02 2003-04-11 한국과학기술연구원 Resolution of chiral compounds
US6828119B2 (en) * 2001-01-04 2004-12-07 Bristol Myers Squibb Company Enzymatic deprotection of amines and hydroxides
FR2853327B1 (en) * 2003-04-04 2012-07-27 Solvay PROCESS FOR THE PRODUCTION OF ENANTIOPOR BETA-AMINOACID DERIVATIVES AND ENANTIOPA BETA-AMINOACIDIC DERIVATIVES
KR100650798B1 (en) * 2004-07-19 2006-11-27 (주)제이코통상 Process for preparing chiral substituted carboxylic acid
FR2876102A1 (en) * 2004-10-04 2006-04-07 Solvay ENANTIOPUR HETEROCYCLIC COMPOUND
KR100650797B1 (en) * 2005-12-12 2006-11-27 (주)케미코월드 Process for preparing chiral substituted cyclopropane carboxamide
FR2986804A1 (en) * 2012-02-09 2013-08-16 Servier Lab PROCESS FOR THE ENZYMATIC SYNTHESIS OF (7S) 3,4-DIMETHOXYBICYCLO [4.2.0] OCTA-1,3,5-TRIENE 7-CARBOXYLIC ACID OR ITS ESTERS, AND APPLICATION TO THE SYNTHESIS OF IVABRADIN AND IES SALTS

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2190428T3 (en) * 1991-06-28 2003-08-01 Smithkline Beecham Corp BIBLICAL FIBRINOGEN ANTAGONISTS.
WO1994014776A2 (en) * 1992-12-21 1994-07-07 Smithkline Beecham Corporation Bicyclic fibrinogen antagonists
MA23420A1 (en) * 1994-01-07 1995-10-01 Smithkline Beecham Corp BICYCLIC FIBRINOGEN ANTAGONISTS.
US5529929A (en) * 1995-06-07 1996-06-25 Seprachem, Inc. Optical resolution of alkyl 1,4-benzodioxan-2-carboxylates using esterase from serratia marcescens

Also Published As

Publication number Publication date
NO993174L (en) 1999-06-25
ZA9711566B (en) 1998-06-29
AU730064B2 (en) 2001-02-22
AU5331498A (en) 1998-07-31
BR9714099A (en) 2000-03-21
PL334293A1 (en) 2000-02-14
WO1998029561A1 (en) 1998-07-09
IL130580A0 (en) 2000-06-01
HUP0002825A2 (en) 2000-12-28
EP0964928A1 (en) 1999-12-22
TR199901487T2 (en) 1999-11-22
AR010860A1 (en) 2000-07-12
KR20000069705A (en) 2000-11-25
JP2001507231A (en) 2001-06-05
NO993174D0 (en) 1999-06-25
HUP0002825A3 (en) 2002-09-30
CN1246157A (en) 2000-03-01
CO4930272A1 (en) 2000-06-27
CA2276134A1 (en) 1998-07-09

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