IL108029A - Enzymatic preparation of optically active transglycidic acid esters and their use for the preparation of benz(othi) azepines - Google Patents

Enzymatic preparation of optically active transglycidic acid esters and their use for the preparation of benz(othi) azepines

Info

Publication number: IL108029A
Authority: IL; Israel
Prior art keywords: ester; preparation; process according; trans; optically active
Prior art date: 1992-12-18

Application number

IL10802993A

Other languages

English (en)

Other versions

IL108029A0 (en

Original Assignee

Dsm Nv

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.)

1992-12-18

Filing date

1993-12-15

Publication date

1998-09-24

1993-12-15 Application filed by Dsm Nv filed Critical Dsm Nv

1994-04-12 Publication of IL108029A0 publication Critical patent/IL108029A0/xx

1998-09-24 Publication of IL108029A publication Critical patent/IL108029A/en

Links

150000002148 esters Chemical class 0.000 title claims abstract description 40
238000002360 preparation method Methods 0.000 title claims abstract description 13
150000001538 azepines Chemical class 0.000 title claims description 4
239000002253 acid Substances 0.000 title abstract description 6
230000002255 enzymatic effect Effects 0.000 title description 4
102000004190 Enzymes Human genes 0.000 claims abstract description 30
108090000790 Enzymes Proteins 0.000 claims abstract description 30
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 claims abstract description 10
239000000203 mixture Substances 0.000 claims abstract description 10
-1 trans-3-phenylglycidic acid ester Chemical class 0.000 claims abstract description 9
HALONVPKHYIEQU-JGVFFNPUSA-N (2r,3s)-3-phenyloxirane-2-carboxylic acid Chemical compound OC(=O)[C@@H]1O[C@H]1C1=CC=CC=C1 HALONVPKHYIEQU-JGVFFNPUSA-N 0.000 claims abstract description 6
239000011541 reaction mixture Substances 0.000 claims abstract description 5
230000007062 hydrolysis Effects 0.000 claims description 15
238000006460 hydrolysis reaction Methods 0.000 claims description 15
238000000034 method Methods 0.000 claims description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
230000007071 enzymatic hydrolysis Effects 0.000 claims description 8
238000006047 enzymatic hydrolysis reaction Methods 0.000 claims description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 6
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 6
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 4
241000222120 Candida <Saccharomycetales> Species 0.000 claims description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 3
229960001701 chloroform Drugs 0.000 claims 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
230000029936 alkylation Effects 0.000 claims 1
238000005804 alkylation reaction Methods 0.000 claims 1
238000005859 coupling reaction Methods 0.000 claims 1
150000004702 methyl esters Chemical class 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
241001661345 Moesziomyces antarcticus Species 0.000 abstract description 13
230000035484 reaction time Effects 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 2
150000008038 benzoazepines Chemical class 0.000 abstract 1
150000007657 benzothiazepines Chemical class 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 16
108090001060 Lipase Proteins 0.000 description 12
239000004367 Lipase Substances 0.000 description 12
102000004882 Lipase Human genes 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
235000019421 lipase Nutrition 0.000 description 12
239000002904 solvent Substances 0.000 description 7
238000004448 titration Methods 0.000 description 7
239000000872 buffer Substances 0.000 description 6
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
239000007983 Tris buffer Substances 0.000 description 4
241000179532 [Candida] cylindracea Species 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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 description 4
229960004166 diltiazem Drugs 0.000 description 4
239000000758 substrate Substances 0.000 description 4
239000011942 biocatalyst Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
230000000694 effects Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
FHGWEHGZBUBQKL-UHFFFAOYSA-N 1,2-benzothiazepine Chemical compound S1N=CC=CC2=CC=CC=C12 FHGWEHGZBUBQKL-UHFFFAOYSA-N 0.000 description 2
DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 2
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
230000000707 stereoselective effect Effects 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
OSHCSILDMWBLRX-UHFFFAOYSA-N (4-methoxyphenyl) oxirane-2-carboxylate Chemical compound C1=CC(OC)=CC=C1OC(=O)C1OC1 OSHCSILDMWBLRX-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
240000006439 Aspergillus oryzae Species 0.000 description 1
235000002247 Aspergillus oryzae Nutrition 0.000 description 1
229940127291 Calcium channel antagonist Drugs 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
238000003476 Darzens condensation reaction Methods 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
229930012538 Paclitaxel Natural products 0.000 description 1
108020004511 Recombinant DNA Proteins 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
GWVJLVHNKMLXRM-RPWUZVMVSA-N [(2s,3s)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrobenzo[i][1,5]benzothiazepin-3-yl] acetate Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C(C=CC=2C3=CC=CC=2)=C3S1 GWVJLVHNKMLXRM-RPWUZVMVSA-N 0.000 description 1
GYKFWCDBQAFCLJ-RTWAWAEBSA-N [(2s,3s)-8-chloro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=C(Cl)C=C2S1 GYKFWCDBQAFCLJ-RTWAWAEBSA-N 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000000480 calcium channel blocker Substances 0.000 description 1
229950000308 clentiazem Drugs 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
244000005700 microbiome Species 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1

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
- 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
- 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
- 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)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL10802993A 1992-12-18 1993-12-15 Enzymatic preparation of optically active transglycidic acid esters and their use for the preparation of benz(othi) azepines IL108029A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL9202208A NL9202208A (nl)	1992-12-18	1992-12-18	Werkwijze voor de enzymatische bereiding van optisch aktieve glycidezure esters.

Publications (2)

Publication Number	Publication Date
IL108029A0 IL108029A0 (en)	1994-04-12
IL108029A true IL108029A (en)	1998-09-24

Family

ID=19861657

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10802993A IL108029A (en)	1992-12-18	1993-12-15	Enzymatic preparation of optically active transglycidic acid esters and their use for the preparation of benz(othi) azepines

Country Status (11)

Country	Link
US (1)	US5407828A (de)
EP (1)	EP0602740B1 (de)
JP (1)	JP3781788B2 (de)
AT (1)	ATE176931T1 (de)
CA (1)	CA2111595C (de)
DE (1)	DE69323600T2 (de)
DK (1)	DK0602740T3 (de)
ES (1)	ES2129491T3 (de)
FI (1)	FI102974B1 (de)
IL (1)	IL108029A (de)
NL (1)	NL9202208A (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1249777B (it) *	1990-05-17	1995-03-18	Zambon Spa	Processo per la preparazione di intermedi per la sintesi del diltiazem
JP3610600B2 (ja) *	1994-08-22	2005-01-12	チッソ株式会社	光学活性エンド−２−ノルボルネオール類の製造方法
ES2216495T3 (es)	1998-02-17	2004-10-16	G.D. SEARLE & CO.	Procedimiento para la resolucion enzimatica de lactamas.
IT1302261B1 (it) *	1998-09-24	2000-09-05	Zambon Spa	Processo per la risoluzione cinetica enzimatica di 3-fenilglicidatiper transesterificazione con amminoalcoli
US20080249310A1 (en) *	2004-07-23	2008-10-09	Thijs Kuilman	Process For the Preparation of (2R,3R)-2-Hydroxy-3-Amino-3-Aryl-Propionamide and (2R,3R)-2-Hydroxy-3-Amino-3-Aryl-Propionic Acid Alkyl Ester
CN107446960A (zh) *	2017-09-30	2017-12-08	湖南理工学院	一种采用生物酶催化立体选择性拆分2,3‑二苯基丙酸对映体的方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5273898A (en) *	1986-10-17	1993-12-28	Noro Nordisk A/S	Thermally stable and positionally non-specific lipase isolated from Candida
WO1988002775A1 (en) *	1986-10-17	1988-04-21	Novo Industri A/S	Positionally non-specific lipase from candida sp, a method for producing it, its use and a recombinant dna process for producing it
WO1989002916A1 (en) *	1987-09-28	1989-04-06	Novo-Nordisk A/S	Method for immobilizing lipase
NL8801311A (nl) *	1988-05-20	1989-12-18	Stamicarbon	Fenylglycidaatstereoisomeren, omzettingsprodukten daarvan met 2-nitrothiofenol en de bereiding van diltiazem.
IL91453A0 (en) *	1988-09-02	1990-04-29	Tanabe Seiyaku Co	Preparation of optically active 3-phenyl-glycidic acid esters
US6521445B1 (en) *	1988-10-26	2003-02-18	Sepracor, Inc.	Process for preparing optically active glycidate esters
US5244803A (en) *	1989-09-13	1993-09-14	Tanabe Seiyaku Co., Ltd.	Process for preparing optically active 3-phenylglycidic acid esters
FR2672600B1 (fr) *	1991-02-08	1994-10-14	Synthelabo	Procede de preparation du (-)-(2r,3s)-2,3-epoxy-3-(4-methoxyphenyl) propionate de methyle.

1992
- 1992-12-18 NL NL9202208A patent/NL9202208A/nl not_active Application Discontinuation
1993
- 1993-12-13 DK DK93203495T patent/DK0602740T3/da active
- 1993-12-13 US US08/165,344 patent/US5407828A/en not_active Expired - Lifetime
- 1993-12-13 EP EP93203495A patent/EP0602740B1/de not_active Expired - Lifetime
- 1993-12-13 ES ES93203495T patent/ES2129491T3/es not_active Expired - Lifetime
- 1993-12-13 AT AT93203495T patent/ATE176931T1/de active
- 1993-12-13 DE DE69323600T patent/DE69323600T2/de not_active Expired - Lifetime
- 1993-12-15 IL IL10802993A patent/IL108029A/en not_active IP Right Cessation
- 1993-12-16 CA CA002111595A patent/CA2111595C/en not_active Expired - Fee Related
- 1993-12-16 JP JP31669193A patent/JP3781788B2/ja not_active Expired - Fee Related
- 1993-12-17 FI FI935712A patent/FI102974B1/fi active

Also Published As

Publication number	Publication date
CA2111595C (en)	2004-12-14
US5407828A (en)	1995-04-18
EP0602740A1 (de)	1994-06-22
JPH06335399A (ja)	1994-12-06
NL9202208A (nl)	1994-07-18
DK0602740T3 (da)	1999-09-27
FI102974B (fi)	1999-03-31
EP0602740B1 (de)	1999-02-24
FI935712L (fi)	1994-06-19
DE69323600D1 (de)	1999-04-01
DE69323600T2 (de)	1999-09-23
ES2129491T3 (es)	1999-06-16
FI102974B1 (fi)	1999-03-31
FI935712A0 (fi)	1993-12-17
ATE176931T1 (de)	1999-03-15
CA2111595A1 (en)	1994-06-19
JP3781788B2 (ja)	2006-05-31
IL108029A0 (en)	1994-04-12

Legal Events

Date	Code	Title
1999-01-26	FF	Patent granted
1999-07-14	KB	Patent renewed
2000-06-01	KB	Patent renewed
2004-02-08	KB	Patent renewed
2008-01-22	KB	Patent renewed
2011-12-29	KB	Patent renewed
2014-07-31	EXP	Patent expired

Publication	Publication Date	Title
US4732853A (en)	1988-03-22	Method of making chiral epoxy alcohols
EP0343714B1 (de)	1994-11-02	Phenylglycidat-Stereoisomere, Umsetzungsprodukte mit 2-Nitrothiophenol und Herstellung von Diltiazen
EP0602740B1 (de)	1999-02-24	Verfahren zur enzymatischen Herstellung von optisch aktiven Estern einer Transglycidsäure
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