BE1005406A0 - Procede de preparation d'intermediaires utiles dans la synthese de benzothiazepines. - Google Patents

Procede de preparation d'intermediaires utiles dans la synthese de benzothiazepines. Download PDF

Info

Publication number: BE1005406A0
Authority: BE; Belgium
Prior art keywords: methoxyphenyl; lipase; chosen; transesterification; methyl
Prior art date: 1990-05-17

Application number

BE9100458A

Other languages

English (en)

French (fr)

Inventor

Luca Ghirotto

Stefano Servi

Claudio Fuganti

Angelo Gentile

Claudio Giordano

Original Assignee

Zambon Spa

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.)

1990-05-17

Filing date

1991-05-16

Publication date

1993-07-13

1991-05-16 Application filed by Zambon Spa filed Critical Zambon Spa

1993-07-13 Publication of BE1005406A0 publication Critical patent/BE1005406A0/fr

Links

238000000034 method Methods 0.000 title claims abstract description 30
238000002360 preparation method Methods 0.000 title claims abstract description 10
230000015572 biosynthetic process Effects 0.000 title abstract description 6
238000003786 synthesis reaction Methods 0.000 title abstract description 6
150000007657 benzothiazepines Chemical class 0.000 title description 2
239000000203 mixture Substances 0.000 claims abstract description 26
238000005809 transesterification reaction Methods 0.000 claims abstract description 24
150000001875 compounds Chemical class 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical class OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 claims description 37
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 35
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 33
108090001060 Lipase Proteins 0.000 claims description 32
239000004367 Lipase Substances 0.000 claims description 32
102000004882 Lipase Human genes 0.000 claims description 32
235000019421 lipase Nutrition 0.000 claims description 32
150000004702 methyl esters Chemical class 0.000 claims description 23
150000002148 esters Chemical class 0.000 claims description 21
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 13
102000004190 Enzymes Human genes 0.000 claims description 12
108090000790 Enzymes Proteins 0.000 claims description 12
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
230000002255 enzymatic effect Effects 0.000 claims description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
238000002425 crystallisation Methods 0.000 claims description 5
230000008025 crystallization Effects 0.000 claims description 5
125000004494 ethyl ester group Chemical group 0.000 claims description 5
RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 claims description 5
150000001298 alcohols Chemical class 0.000 claims description 4
-1 aliphatic alcohols Chemical class 0.000 claims description 4
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
241000222120 Candida <Saccharomycetales> Species 0.000 claims description 3
230000000813 microbial effect Effects 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 claims 2
MOQVHOPVBREXLY-UHFFFAOYSA-N 3h-dioxol-4-ylmethanol Chemical compound OCC1=COOC1 MOQVHOPVBREXLY-UHFFFAOYSA-N 0.000 claims 1
241000228212 Aspergillus Species 0.000 claims 1
241000589516 Pseudomonas Species 0.000 claims 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 1
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims 1
150000002500 ions Chemical class 0.000 claims 1
210000004185 liver Anatomy 0.000 claims 1
244000005700 microbiome Species 0.000 claims 1
108010079522 solysime Proteins 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 5
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 abstract description 3
229960004166 diltiazem Drugs 0.000 abstract description 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical group CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 abstract 1
239000002253 acid Substances 0.000 description 19
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 13
241000179532 [Candida] cylindracea Species 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
238000004128 high performance liquid chromatography Methods 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
238000004458 analytical method Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
229940088598 enzyme Drugs 0.000 description 7
239000000126 substance Substances 0.000 description 7
230000000694 effects Effects 0.000 description 5
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
CVZUMGUZDAWOGA-UHFFFAOYSA-N methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate Chemical compound COC(=O)C1OC1C1=CC=C(OC)C=C1 CVZUMGUZDAWOGA-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
BTANRVKWQNVYAZ-SCSAIBSYSA-N (2R)-butan-2-ol Chemical compound CC[C@@H](C)O BTANRVKWQNVYAZ-SCSAIBSYSA-N 0.000 description 2
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
230000001093 anti-cancer Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229960002376 chymotrypsin Drugs 0.000 description 2
238000000605 extraction Methods 0.000 description 2
230000002641 glycemic effect Effects 0.000 description 2
238000003760 magnetic stirring Methods 0.000 description 2
YKNYRRVISWJDSR-UHFFFAOYSA-N methyl oxirane-2-carboxylate Chemical compound COC(=O)C1CO1 YKNYRRVISWJDSR-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
230000024883 vasodilation Effects 0.000 description 2
BTANRVKWQNVYAZ-BYPYZUCNSA-N (2S)-butan-2-ol Chemical compound CC[C@H](C)O BTANRVKWQNVYAZ-BYPYZUCNSA-N 0.000 description 1
DJODHLGSFAUOGL-UHFFFAOYSA-N 2-(4-methylphenyl)oxirane-2-carboxylic acid Chemical class C1=CC(C)=CC=C1C1(C(O)=O)OC1 DJODHLGSFAUOGL-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
101710084378 Lipase 2 Proteins 0.000 description 1
101710084369 Lipase 4 Proteins 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000006340 racemization Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
- 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
- C12P17/02—Oxygen as only ring hetero atoms
- 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)
Wood Science & Technology (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Microbiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Analytical Chemistry (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Epoxy Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BE9100458A 1990-05-17 1991-05-16 Procede de preparation d'intermediaires utiles dans la synthese de benzothiazepines. BE1005406A0 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT02034890A IT1249777B (it)	1990-05-17	1990-05-17	Processo per la preparazione di intermedi per la sintesi del diltiazem

Publications (1)

Publication Number	Publication Date
BE1005406A0 true BE1005406A0 (fr)	1993-07-13

Family

ID=11165937

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE9100458A BE1005406A0 (fr)	1990-05-17	1991-05-16	Procede de preparation d'intermediaires utiles dans la synthese de benzothiazepines.

Country Status (13)

Country	Link
US (2)	US5571704A (de)
JP (2)	JP3060187B2 (de)
AT (1)	AT400446B (de)
BE (1)	BE1005406A0 (de)
CA (1)	CA2042535C (de)
CH (1)	CH682670A5 (de)
DE (1)	DE4115697C2 (de)
ES (1)	ES2033203B1 (de)
FR (1)	FR2662178B1 (de)
GB (2)	GB2246351B (de)
IT (1)	IT1249777B (de)
NL (1)	NL194616C (de)
SE (1)	SE509297C2 (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2687789B2 (ja) *	1991-08-13	1997-12-08	田辺製薬株式会社	光学活性３−フェニルグリシッド酸エステル類化合物の製法
ES2050067B1 (es) *	1992-06-08	1994-12-16	Menarini Lab	Proceso para la produccion de acido s-(+)-2-(3-benzoilfenil) propionico por transesterificacion enantioselectiva con un alcohol bifuncional catalizada enzimaticamente en medio organico.
ES2048653B1 (es) *	1992-06-08	1994-12-16	Menarini Lab	Proceso para la produccion de acido s-(+)-2-(3-benzoilfenil) propionico por transesterificacion enantioselectiva catalizada enzimaticamente en un disolvente organico.
US6020174A (en) *	1992-07-27	2000-02-01	The Board Of Governors For Higher Education	Chemoenzymatic synthesis of the taxol C-13 side chain N-benzolyl- (2R,3S)-Phenylisoserine
DE4225155C1 (de) *	1992-07-30	1993-08-05	Hoechst Ag, 6230 Frankfurt, De
SG72731A1 (en) *	1996-03-15	2000-05-23	Nabe Seiyaku Co Ltd	Process for preparing optically active trans-3-phenylglycidamide compounds
IL123352A0 (en)	1997-02-27	1998-09-24	Tanabe Seiyaku Co	Process for preparing an optically active trans-3-substituted glycidic acid ester
KR20010013668A (ko) *	1997-06-11	2001-02-26	찌바따 이찌로	광학 활성 페닐옥시란 화합물의 제조방법
IT1302261B1 (it) *	1998-09-24	2000-09-05	Zambon Spa	Processo per la risoluzione cinetica enzimatica di 3-fenilglicidatiper transesterificazione con amminoalcoli
DE19901925A1 (de) *	1999-01-19	2000-07-27	Aventis Res & Tech Gmbh & Co	Verfahren zur Trennung optischer Isomerer durch simultane Durchführung einer enzymatischen Reaktion und einer chromatographischen Trennung
US20050176118A1 (en) *	2002-02-06	2005-08-11	Oakeshott John G.	Esterases with lipase activity

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0343714A1 (de) *	1988-05-20	1989-11-29	Dsm N.V.	Phenylglycidat-Stereoisomere, Umsetzungsprodukte mit 2-Nitrothiophenol und Herstellung von Diltiazen
EP0344791A2 (de) *	1988-06-02	1989-12-06	Montedison S.p.A.	Verfahren zur enzymatischen Auftrennung von optischen Isomeren aus racemischen Esterderivaten von 3-Merkapto-2-alkylpropionsäure
EP0362556A1 (de) *	1988-09-02	1990-04-11	Tanabe Seiyaku Co., Ltd.	Verfahren zur Herstellung von optisch aktiven 3-Phenylglycidsäureestern
EP0498706A1 (de) *	1991-02-08	1992-08-12	Synthelabo	Verfahren zur Herstellung von (-)-(2R,3S)-2,3-Epoxy-3-(4-Methoxyphenyl)propionat-methylester

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3833774C1 (de) *	1988-10-05	1990-04-26	Fischer-Werke Artur Fischer Gmbh & Co Kg, 7244 Waldachtal, De
US5108916A (en) *	1989-06-05	1992-04-28	Rhone-Poulenc Rorer, S.A.	Process for stereoselectively hydrolyzing, transesterifying or esterifying with immobilized isozyme of lipase from candida rugosa
US5244803A (en) *	1989-09-13	1993-09-14	Tanabe Seiyaku Co., Ltd.	Process for preparing optically active 3-phenylglycidic acid esters
JPH0779706B2 (ja) *	1990-03-22	1995-08-30	田辺製薬株式会社	２―クロロ―３―ヒドロキシ―３―フエニルプロピオン酸エステル類の製法
IT1240651B (it) *	1990-05-17	1993-12-17	Zambon Spa	Processo per la risoluzione di derivati glicidici
NL9202208A (nl) *	1992-12-18	1994-07-18	Dsm Nv	Werkwijze voor de enzymatische bereiding van optisch aktieve glycidezure esters.

1990
- 1990-05-17 IT IT02034890A patent/IT1249777B/it active IP Right Grant
1991
- 1991-05-03 CH CH1329/91A patent/CH682670A5/it not_active IP Right Cessation
- 1991-05-14 CA CA002042535A patent/CA2042535C/en not_active Expired - Lifetime
- 1991-05-14 DE DE4115697A patent/DE4115697C2/de not_active Expired - Fee Related
- 1991-05-14 AT AT0099591A patent/AT400446B/de not_active IP Right Cessation
- 1991-05-15 FR FR9105866A patent/FR2662178B1/fr not_active Expired - Fee Related
- 1991-05-16 SE SE9101482A patent/SE509297C2/sv not_active IP Right Cessation
- 1991-05-16 NL NL9100854A patent/NL194616C/nl not_active IP Right Cessation
- 1991-05-16 BE BE9100458A patent/BE1005406A0/fr not_active IP Right Cessation
- 1991-05-16 JP JP3210541A patent/JP3060187B2/ja not_active Expired - Lifetime
- 1991-05-16 GB GB9110610A patent/GB2246351B/en not_active Expired - Fee Related
- 1991-05-16 ES ES9101193A patent/ES2033203B1/es not_active Expired - Fee Related
- 1991-09-30 GB GB9120710A patent/GB2247020B/en not_active Expired - Fee Related
1995
- 1995-03-14 US US08/404,284 patent/US5571704A/en not_active Expired - Lifetime
- 1995-06-07 US US08/487,584 patent/US6346632B1/en not_active Expired - Fee Related
1999
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Also Published As

Publication number	Publication date
IT1249777B (it)	1995-03-18
JP2000139492A (ja)	2000-05-23
US5571704A (en)	1996-11-05
FR2662178A1 (fr)	1991-11-22
CA2042535C (en)	1998-06-16
DE4115697C2 (de)	2000-09-07
GB9110610D0 (en)	1991-07-03
GB9120710D0 (en)	1991-11-13
GB2247020B (en)	1993-12-15
NL194616B (nl)	2002-05-01
ATA99591A (de)	1995-05-15
IT9020348A0 (it)	1990-05-17
SE509297C2 (sv)	1999-01-11
JP3060187B2 (ja)	2000-07-10
FR2662178B1 (fr)	1995-05-05
US6346632B1 (en)	2002-02-12
DE4115697A1 (de)	1991-11-21
ES2033203A1 (es)	1993-03-01
GB2246351B (en)	1993-12-15
GB2246351A (en)	1992-01-29
JPH04228095A (ja)	1992-08-18
CH682670A5 (it)	1993-10-29
AT400446B (de)	1995-12-27
JP3223317B2 (ja)	2001-10-29
GB2247020A (en)	1992-02-19
SE9101482D0 (sv)	1991-05-16
IT9020348A1 (it)	1991-11-17
ES2033203B1 (es)	1993-12-16
CA2042535A1 (en)	1991-11-18
SE9101482L (sv)	1991-11-18
NL9100854A (nl)	1991-12-16
NL194616C (nl)	2002-09-03

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2005-11-30	RE	Patent lapsed	Effective date: 20050531
2007-12-31	RE	Patent lapsed	Effective date: 20050531

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