AR010860A1 - PROCEDURE FOR PREPARING COMPOUNDS THROUGH ENZYMATIC RESOLUTION AND RELATED COMPOUNDS - Google Patents

PROCEDURE FOR PREPARING COMPOUNDS THROUGH ENZYMATIC RESOLUTION AND RELATED COMPOUNDS

Info

Publication number
AR010860A1
AR010860A1 ARP970106167A ARP970106167A AR010860A1 AR 010860 A1 AR010860 A1 AR 010860A1 AR P970106167 A ARP970106167 A AR P970106167A AR P970106167 A ARP970106167 A AR P970106167A AR 010860 A1 AR010860 A1 AR 010860A1
Authority
AR
Argentina
Prior art keywords
alkyl
compounds
bipiperidin
procedure
preparing
Prior art date
Application number
ARP970106167A
Other languages
Spanish (es)
Original Assignee
Smithkline Beecham Plc
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 Plc filed Critical Smithkline Beecham Plc
Publication of AR010860A1 publication Critical patent/AR010860A1/en

Links

Classifications

    • 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
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Enzymes And Modification Thereof (AREA)

Abstract

Un procedimiento para preparar un compuesto de formula (I), en la que X es H, halogeno, CO2R3, OR4, COR5 o una cadena secundaria de antagonistade fibrinogeno o vitronectina; R2 es alquilo (C1-C6), opcionalmente sustituido con Ar, Het, ocicloalq uilo (C1-C6); R3 es alquilo (C1-C6) o bencilo; R4 esalquilo (C1-C6), COR3 o bencilo; R5 es 4,4-bipiperidin-1-ilo, (1- benciloxicarbonil)-4,4-bipiperidin-1-ilo o (1-t-butoxicarbonil)-4,4-bipiperidin-1-ilo; que comprende: (a)tratar un comp uesto de formula (II), en la que R1 es alquilo (C1-C20) o alquenilo (C3-C20), opcionalmente sustituidocon Ar, NR2, o NR3+, en donde R es alquilo (C1-C4); con lipasa B de Candida Antarctica; y (b) separar el ácido carbocílicoresultante, ácido 2 ,3,4,5-tetrahidro-4-metil-3-oxo-1H-1,4-benzodiazepina-2-ácetico, del correspondiente éster y compuestos relacionados.A method of preparing a compound of formula (I), wherein X is H, halogen, CO2R3, OR4, COR5 or a fibrinogen antagonist or vitronectin side chain; R2 is (C1-C6) alkyl, optionally substituted with Ar, Het, or C1-C6 ocycloalkyl; R3 is (C1-C6) alkyl or benzyl; R4 is (C1-C6) alkyl, COR3 or benzyl; R5 is 4,4-bipiperidin-1-yl, (1- benzyloxycarbonyl) -4,4-bipiperidin-1-yl or (1-t-butoxycarbonyl) -4,4-bipiperidin-1-yl; comprising: (a) treating a compound of formula (II), wherein R1 is (C1-C20) alkyl or (C3-C20) alkenyl, optionally substituted with Ar, NR2, or NR3 +, wherein R is alkyl ( C1-C4); with lipase B from Candida Antarctica; and (b) separating the resulting carbocylic acid, 2, 3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid, from the corresponding ester and related compounds.

ARP970106167A 1996-12-27 1997-12-23 PROCEDURE FOR PREPARING COMPOUNDS THROUGH ENZYMATIC RESOLUTION AND RELATED COMPOUNDS AR010860A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US3385396P 1996-12-27 1996-12-27

Publications (1)

Publication Number Publication Date
AR010860A1 true AR010860A1 (en) 2000-07-12

Family

ID=21872833

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP970106167A AR010860A1 (en) 1996-12-27 1997-12-23 PROCEDURE FOR PREPARING COMPOUNDS THROUGH ENZYMATIC RESOLUTION AND RELATED COMPOUNDS

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 (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69914458T2 (en) 1998-02-17 2004-10-28 G.D. Searle & Co., Chicago METHOD FOR ENZYMATICALLY DISCHARGING LACTAS
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 Method for preparing optically active carboxylic acid
FR2876102A1 (en) * 2004-10-04 2006-04-07 Solvay ENANTIOPUR HETEROCYCLIC COMPOUND
KR100650797B1 (en) * 2005-12-12 2006-11-27 (주)케미코월드 Method for preparing optically active 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
CN117363683A (en) * 2023-10-09 2024-01-09 江苏惠利生物科技有限公司 Enzymatic resolution method of lipase benzodiazepine-acetate

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU666318B2 (en) * 1991-06-28 1996-02-08 Smithkline Beecham Corporation Bicyclic fibrinogen antagonists
NZ314922A (en) * 1992-12-21 1998-11-25 Smithkline Beecham Corp Benzodiazepinones; nitrogen containing heterocyclic intermediates and pharmaceutical compositions
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
WO1998029561A1 (en) 1998-07-09
KR20000069705A (en) 2000-11-25
JP2001507231A (en) 2001-06-05
CA2276134A1 (en) 1998-07-09
CN1246157A (en) 2000-03-01
PL334293A1 (en) 2000-02-14
CO4930272A1 (en) 2000-06-27
HUP0002825A3 (en) 2002-09-30
NZ336376A (en) 2000-11-24
AU730064B2 (en) 2001-02-22
ZA9711566B (en) 1998-06-29
NO993174L (en) 1999-06-25
EP0964928A1 (en) 1999-12-22
AU5331498A (en) 1998-07-31
IL130580A0 (en) 2000-06-01
BR9714099A (en) 2000-03-21
TR199901487T2 (en) 1999-11-22
HUP0002825A2 (en) 2000-12-28
NO993174D0 (en) 1999-06-25

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