IL92122A - Process for making optically active glycid esters - Google Patents

Process for making optically active glycid esters

Info

Publication number: IL92122A
Authority: IL; Israel
Prior art keywords: enzyme; membrane; formula; organic solution; group
Prior art date: 1988-10-26

Application number

IL9212289A

Other languages

English (en)

Hebrew (he)

Other versions

IL92122A0 (en

Original Assignee

Sepracor Inc

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.)

1988-10-26

Filing date

1989-10-26

Publication date

1996-06-18

1989-02-10 Priority claimed from US07/309,769 external-priority patent/US5274300A/en

1989-10-26 Application filed by Sepracor Inc filed Critical Sepracor Inc

1990-07-12 Publication of IL92122A0 publication Critical patent/IL92122A0/xx

1996-06-18 Publication of IL92122A publication Critical patent/IL92122A/en

Links

OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical class OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 title claims description 36
238000004519 manufacturing process Methods 0.000 title abstract description 29
238000000034 method Methods 0.000 claims abstract description 292
239000012528 membrane Substances 0.000 claims abstract description 162
150000002148 esters Chemical class 0.000 claims abstract description 135
238000006243 chemical reaction Methods 0.000 claims abstract description 123
-1 glycidic acid ester Chemical class 0.000 claims abstract description 112
230000008569 process Effects 0.000 claims abstract description 73
150000001875 compounds Chemical class 0.000 claims abstract description 61
239000006227 byproduct Substances 0.000 claims abstract description 30
239000002904 solvent Substances 0.000 claims abstract description 28
230000000707 stereoselective effect Effects 0.000 claims abstract description 16
238000010931 ester hydrolysis Methods 0.000 claims abstract description 12
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 16
102000004190 Enzymes Human genes 0.000 claims description 261
108090000790 Enzymes Proteins 0.000 claims description 260
229940088598 enzyme Drugs 0.000 claims description 256
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 229
239000000243 solution Substances 0.000 claims description 130
108090001060 Lipase Proteins 0.000 claims description 74
102000004882 Lipase Human genes 0.000 claims description 74
239000004367 Lipase Substances 0.000 claims description 73
235000019421 lipase Nutrition 0.000 claims description 73
239000000203 mixture Substances 0.000 claims description 72
238000006460 hydrolysis reaction Methods 0.000 claims description 67
230000007062 hydrolysis Effects 0.000 claims description 66
229940040461 lipase Drugs 0.000 claims description 66
239000003960 organic solvent Substances 0.000 claims description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
239000000463 material Substances 0.000 claims description 36
125000004432 carbon atom Chemical group C* 0.000 claims description 33
230000003301 hydrolyzing effect Effects 0.000 claims description 31
230000003287 optical effect Effects 0.000 claims description 31
108091005804 Peptidases Proteins 0.000 claims description 30
239000004365 Protease Substances 0.000 claims description 30
239000003795 chemical substances by application Substances 0.000 claims description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 25
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
CVZUMGUZDAWOGA-UHFFFAOYSA-N methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate Chemical group COC(=O)C1OC1C1=CC=C(OC)C=C1 CVZUMGUZDAWOGA-UHFFFAOYSA-N 0.000 claims description 20
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 19
239000007864 aqueous solution Substances 0.000 claims description 18
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 17
230000000269 nucleophilic effect Effects 0.000 claims description 17
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 16
238000006047 enzymatic hydrolysis reaction Methods 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
241000222120 Candida <Saccharomycetales> Species 0.000 claims description 14
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 14
238000002425 crystallisation Methods 0.000 claims description 14
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YKNYRRVISWJDSR-UHFFFAOYSA-N methyl oxirane-2-carboxylate Chemical compound COC(=O)C1CO1 YKNYRRVISWJDSR-UHFFFAOYSA-N 0.000 claims description 14
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
239000006185 dispersion Substances 0.000 claims description 13
230000007071 enzymatic hydrolysis Effects 0.000 claims description 13
125000000547 substituted alkyl group Chemical group 0.000 claims description 13
239000012510 hollow fiber Substances 0.000 claims description 12
125000003107 substituted aryl group Chemical group 0.000 claims description 12
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 10
108090000371 Esterases Proteins 0.000 claims description 10
239000003153 chemical reaction reagent Substances 0.000 claims description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 8
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
239000003849 aromatic solvent Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
238000007142 ring opening reaction Methods 0.000 claims description 6
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150000001340 alkali metals Chemical class 0.000 claims description 5
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239000011734 sodium Substances 0.000 claims description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
108050006759 Pancreatic lipases Proteins 0.000 claims description 4
102000019280 Pancreatic lipases Human genes 0.000 claims description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
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108090000317 Chymotrypsin Proteins 0.000 claims description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
241000179532 [Candida] cylindracea Species 0.000 claims description 3
229960002376 chymotrypsin Drugs 0.000 claims description 3
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
238000000926 separation method Methods 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
239000008096 xylene Substances 0.000 claims description 3
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
241000589540 Pseudomonas fluorescens Species 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
229940117389 dichlorobenzene Drugs 0.000 claims description 2
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
150000002443 hydroxylamines Chemical class 0.000 claims description 2
239000007790 solid phase Substances 0.000 claims description 2
230000008093 supporting effect Effects 0.000 claims description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 claims 2
YSULOORXQBDPCU-UHFFFAOYSA-N 2-(trimethylazaniumyl)ethanehydrazonate;hydrochloride Chemical compound [Cl-].C[N+](C)(C)CC(=O)NN YSULOORXQBDPCU-UHFFFAOYSA-N 0.000 claims 2
241000124008 Mammalia Species 0.000 claims 2
108010019160 Pancreatin Proteins 0.000 claims 2
108010055297 Sterol Esterase Proteins 0.000 claims 2
102000000019 Sterol Esterase Human genes 0.000 claims 2
108090000631 Trypsin Proteins 0.000 claims 2
102000004142 Trypsin Human genes 0.000 claims 2
125000003275 alpha amino acid group Chemical group 0.000 claims 2
125000003277 amino group Chemical group 0.000 claims 2
239000013592 cell lysate Substances 0.000 claims 2
238000005374 membrane filtration Methods 0.000 claims 2
239000012982 microporous membrane Substances 0.000 claims 2
239000012038 nucleophile Substances 0.000 claims 2
229940055695 pancreatin Drugs 0.000 claims 2
125000003944 tolyl group Chemical group 0.000 claims 2
239000012588 trypsin Substances 0.000 claims 2
229960001322 trypsin Drugs 0.000 claims 2
FPMXPTIRDWHULR-UHFFFAOYSA-N 2-pyridin-1-ium-1-ylacetate;hydrochloride Chemical compound [Cl-].OC(=O)C[N+]1=CC=CC=C1 FPMXPTIRDWHULR-UHFFFAOYSA-N 0.000 claims 1
239000004953 Aliphatic polyamide Substances 0.000 claims 1
240000006439 Aspergillus oryzae Species 0.000 claims 1
235000002247 Aspergillus oryzae Nutrition 0.000 claims 1
239000002033 PVDF binder Substances 0.000 claims 1
239000004372 Polyvinyl alcohol Substances 0.000 claims 1
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229920003231 aliphatic polyamide Polymers 0.000 claims 1
239000004760 aramid Substances 0.000 claims 1
229920003235 aromatic polyamide Polymers 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
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229920002678 cellulose Polymers 0.000 claims 1
238000005119 centrifugation Methods 0.000 claims 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 1
229920001577 copolymer Polymers 0.000 claims 1
230000002209 hydrophobic effect Effects 0.000 claims 1
150000003949 imides Chemical class 0.000 claims 1
239000003112 inhibitor Substances 0.000 claims 1
125000001624 naphthyl group Chemical group 0.000 claims 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims 1
150000002924 oxiranes Chemical group 0.000 claims 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
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DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims 1
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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 40
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NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 34
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Classifications

- 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
- 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
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Wood Science & Technology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (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)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

IL9212289A 1988-10-26 1989-10-26 Process for making optically active glycid esters IL92122A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US26517188A	1988-10-26	1988-10-26
US07/309,769 US5274300A (en)	1988-10-26	1989-02-10	Enzymatic hydrolysis of glycidate esters in the presence of bisulfite anion
US07/335,636 US6521445B1 (en)	1988-10-26	1989-04-10	Process for preparing optically active glycidate esters

Publications (2)

Publication Number	Publication Date
IL92122A0 IL92122A0 (en)	1990-07-12
IL92122A true IL92122A (en)	1996-06-18

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ID=27401773

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9212289A IL92122A (en)	1988-10-26	1989-10-26	Process for making optically active glycid esters

Country Status (9)

Country	Link
US (1)	US6521445B1 (de)
EP (2)	EP0657544B1 (de)
JP (1)	JP2693248B2 (de)
AT (2)	ATE161583T1 (de)
AU (1)	AU4497289A (de)
CA (1)	CA2001515C (de)
DE (2)	DE68928516D1 (de)
IL (1)	IL92122A (de)
WO (1)	WO1990004643A1 (de)

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NL8801311A (nl) *	1988-05-20	1989-12-18	Stamicarbon	Fenylglycidaatstereoisomeren, omzettingsprodukten daarvan met 2-nitrothiofenol en de bereiding van diltiazem.
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
FI93833C (fi) *	1992-05-14	1995-06-12	Orion Yhtymae Oy	Menetelmä propionihappojohdosten valmistamiseksi
US5273895A (en) *	1992-10-26	1993-12-28	Sepracor, Inc.	Enantioselective production of chiral carboxylic acids
NL9202208A (nl) *	1992-12-18	1994-07-18	Dsm Nv	Werkwijze voor de enzymatische bereiding van optisch aktieve glycidezure esters.
CA2161849A1 (en) *	1994-11-01	1996-05-02	Kazuo Nakahama	Production of optically active compounds
TW438787B (en)	1997-02-27	2001-06-07	Tanabe Seiyaku Co	Process for preparing optically active trans-3-substituted glycidic acid ester
WO1999037754A2 (en) *	1998-01-26	1999-07-29	Pharm-Eco Laboratories, Inc.	Enzyme activated supports for enantiomeric separations
WO2014030106A2 (en) *	2012-08-18	2014-02-27	Unimark Remedies Ltd.	Process for preparation of optically active (2r,3s)-3-(4- methoxyphenyl)glycidic acid methyl ester and cis lactam and uses thereof

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US3635795A (en) *	1968-12-27	1972-01-18	Merck & Co Inc	Enzymatic resolution of racemic (cis-1,2-epoxypropyl) phosphonic acid compounds
US4585768A (en) *	1984-04-10	1986-04-29	Tanabe Seiyaku Co., Ltd.	1,5-benzothiazepine derivatives and processes for preparing the same
US4732853A (en) *	1984-11-21	1988-03-22	President And Fellows Of Harvard College	Method of making chiral epoxy alcohols
IT1189069B (it) *	1986-03-14	1988-01-28	Donegani Guido Ist	Processo per la preparazione biotecnologica della l(-)-carnitina cloruro
EP0488999B1 (de) *	1986-04-16	1997-07-09	Sumitomo Chemical Company Limited	Verfahren zur Herstellung von optisch-aktiven Cyclopropancarbonsäure
JPS6315398A (ja) *	1986-07-07	1988-01-22	株式会社東芝	状態監視用端末装置
US4800162A (en) *	1987-04-01	1989-01-24	Sepracor, Inc.	Method for resolution of steroisomers in multiphase and extractive membrane reactors
JP2627627B2 (ja) *	1987-11-09	1997-07-09	昭和飛行機工業株式会社	保冷コンテナ
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
JPH0678A (ja) *	1992-06-22	1994-01-11	Fujiwara Techno Art:Kk	固体培養装置の空気調和装置における加湿方法

1989
- 1989-04-10 US US07/335,636 patent/US6521445B1/en not_active Expired - Lifetime
- 1989-10-25 CA CA002001515A patent/CA2001515C/en not_active Expired - Lifetime
- 1989-10-26 IL IL9212289A patent/IL92122A/en not_active IP Right Cessation
- 1989-10-26 EP EP95200168A patent/EP0657544B1/de not_active Expired - Lifetime
- 1989-10-26 AT AT95200168T patent/ATE161583T1/de not_active IP Right Cessation
- 1989-10-26 JP JP1511470A patent/JP2693248B2/ja not_active Expired - Lifetime
- 1989-10-26 DE DE68928516T patent/DE68928516D1/de not_active Expired - Lifetime
- 1989-10-26 AT AT89912309T patent/ATE126541T1/de not_active IP Right Cessation
- 1989-10-26 AU AU44972/89A patent/AU4497289A/en not_active Abandoned
- 1989-10-26 DE DE68923883T patent/DE68923883T2/de not_active Expired - Lifetime
- 1989-10-26 WO PCT/US1989/004784 patent/WO1990004643A1/en not_active Ceased
- 1989-10-26 EP EP89912309A patent/EP0440723B1/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0440723B1 (de)	1995-08-16
ATE161583T1 (de)	1998-01-15
CA2001515A1 (en)	1990-04-26
US6521445B1 (en)	2003-02-18
WO1990004643A1 (en)	1990-05-03
CA2001515C (en)	2005-05-10
JP2693248B2 (ja)	1997-12-24
DE68923883T2 (de)	1995-12-14
EP0440723A1 (de)	1991-08-14
DE68923883D1 (de)	1995-09-21
IL92122A0 (en)	1990-07-12
EP0657544B1 (de)	1997-12-29
ATE126541T1 (de)	1995-09-15
DE68928516D1 (de)	1998-02-05
AU4497289A (en)	1990-05-14
EP0440723A4 (en)	1992-05-20
JPH04501360A (ja)	1992-03-12
EP0657544A1 (de)	1995-06-14

Legal Events

Date	Code	Title
1996-11-14	FF	Patent granted
1997-03-18	KB	Patent renewed
2000-01-31	KB	Patent renewed
2001-06-14	RH	Patent void
2004-01-04	KB	Patent renewed
2008-01-06	KB	Patent renewed

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EP0602740B1 (de)	1999-02-24	Verfahren zur enzymatischen Herstellung von optisch aktiven Estern einer Transglycidsäure
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US7067291B2 (en)	2006-06-27	Biocatalytic preparation of enantiomerically enriched aminopentanenitrile
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JPH07115992A (ja)	1995-05-09	光学活性化合物の酵素による製造法