SK329792A3 - Method of production of optic pure esters of (+)-r-2- phenoxypropione acids - Google Patents

Method of production of optic pure esters of (+)-r-2- phenoxypropione acids Download PDF

Info

Publication number: SK329792A3
Authority: SK; Slovakia
Prior art keywords: acid; halopropionic; phenoxypropionic; lipase; ester
Prior art date: 1985-02-27

Application number

SK3297-92A

Other languages

English (en)

Slovak (sk)

Inventor

Alexander Klibanov

Gerald Kircher

Original Assignee

Massachusetts Inst Technology

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.)

1985-02-27

Filing date

1992-11-03

Publication date

1995-02-08

1992-11-03 Application filed by Massachusetts Inst Technology filed Critical Massachusetts Inst Technology

1995-02-08 Publication of SK329792A3 publication Critical patent/SK329792A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 19
150000002148 esters Chemical class 0.000 title claims description 22
-1 (+)-r-2- phenoxypropione acids Chemical class 0.000 title description 4
238000004519 manufacturing process Methods 0.000 title description 4
239000002253 acid Substances 0.000 claims abstract description 58
238000005886 esterification reaction Methods 0.000 claims abstract description 15
230000032050 esterification Effects 0.000 claims abstract description 14
239000004367 Lipase Substances 0.000 claims description 26
102000004882 Lipase Human genes 0.000 claims description 26
108090001060 Lipase Proteins 0.000 claims description 26
235000019421 lipase Nutrition 0.000 claims description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 22
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 claims description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
230000000707 stereoselective effect Effects 0.000 claims description 9
GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 claims description 8
241000179532 [Candida] cylindracea Species 0.000 claims description 8
SXERGJJQSKIUIC-SSDOTTSWSA-N (2r)-2-phenoxypropanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=CC=C1 SXERGJJQSKIUIC-SSDOTTSWSA-N 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
241000235527 Rhizopus Species 0.000 claims description 4
239000003208 petroleum Substances 0.000 claims description 4
241000228245 Aspergillus niger Species 0.000 claims description 3
241000209140 Triticum Species 0.000 claims description 3
235000021307 Triticum Nutrition 0.000 claims description 3
244000168141 Geotrichum candidum Species 0.000 claims description 2
235000017388 Geotrichum candidum Nutrition 0.000 claims description 2
241000235395 Mucor Species 0.000 claims description 2
240000005384 Rhizopus oryzae Species 0.000 claims description 2
235000013752 Rhizopus oryzae Nutrition 0.000 claims description 2
210000000496 pancreas Anatomy 0.000 claims description 2
150000003138 primary alcohols Chemical class 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
150000007513 acids Chemical class 0.000 abstract description 15
229940040461 lipase Drugs 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
230000003287 optical effect Effects 0.000 description 12
SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical class OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 11
102000004190 Enzymes Human genes 0.000 description 10
108090000790 Enzymes Proteins 0.000 description 10
229940088598 enzyme Drugs 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
239000004009 herbicide Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
WNTGYJSOUMFZEP-SSDOTTSWSA-N (R)-mecoprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-SSDOTTSWSA-N 0.000 description 2
241000146387 Chromobacterium viscosum Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
102000019280 Pancreatic lipases Human genes 0.000 description 2
108050006759 Pancreatic lipases Proteins 0.000 description 2
240000004808 Saccharomyces cerevisiae Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
INMAEXGIVZJYIJ-ZCFIWIBFSA-N butyl (2r)-2-bromopropanoate Chemical compound CCCCOC(=O)[C@@H](C)Br INMAEXGIVZJYIJ-ZCFIWIBFSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
229940116369 pancreatic lipase Drugs 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000006340 racemization Effects 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000008096 xylene Substances 0.000 description 2
HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KATNUXHENWPMQJ-ZCFIWIBFSA-N butyl (2r)-2-chloropropanoate Chemical compound CCCCOC(=O)[C@@H](C)Cl KATNUXHENWPMQJ-ZCFIWIBFSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000003809 water extraction Methods 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
- 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
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK3297-92A 1985-02-27 1992-11-03 Method of production of optic pure esters of (+)-r-2- phenoxypropione acids SK329792A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/706,039 US4601987A (en)	1985-02-27	1985-02-27	Enzymatic production of optical isomers of 2-halopropionic acids

Publications (1)

Publication Number	Publication Date
SK329792A3 true SK329792A3 (en)	1995-02-08

Family

ID=24835974

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SK3297-92A SK329792A3 (en)	1985-02-27	1992-11-03	Method of production of optic pure esters of (+)-r-2- phenoxypropione acids
SK3296-92A SK329692A3 (en)	1985-02-27	1992-11-03	Method of production of optic pure esters of (+)-r-2- -phenoxypropione acids

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SK3296-92A SK329692A3 (en)	1985-02-27	1992-11-03	Method of production of optic pure esters of (+)-r-2- -phenoxypropione acids

Country Status (13)

Country	Link
US (1)	US4601987A (cs)
EP (1)	EP0206436B1 (cs)
AT (1)	ATE70563T1 (cs)
CZ (3)	CZ132286A3 (cs)
DD (3)	DD258625A1 (cs)
DE (1)	DE3682958D1 (cs)
ES (1)	ES8705351A1 (cs)
NZ (1)	NZ215099A (cs)
PL (1)	PL148128B1 (cs)
SK (2)	SK329792A3 (cs)
TR (1)	TR23363A (cs)
YU (3)	YU28686A (cs)
ZA (1)	ZA861473B (cs)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61227797A (ja) *	1985-04-01	1986-10-09	Kanegafuchi Chem Ind Co Ltd	光学活性グリコ−ル類の製造方法
US5322791A (en) *	1985-12-20	1994-06-21	Wisconsin Alumni Research Foundation	Process for preparing (S)-α-methylarylacetic acids
US4897357A (en) *	1985-12-31	1990-01-30	Ethyl Corporation	(S) α-cyano-3-phenoxy-benzyl acetate
GB8600245D0 (en) *	1986-01-07	1986-02-12	Shell Int Research	Preparation of 2-arylpropionic acids
US5032523A (en) *	1987-01-14	1991-07-16	Lion Corporation	Preparation of optically active esters
JP2707076B2 (ja) *	1987-05-01	1998-01-28	チッソ株式会社	光学活性化合物の製造法
DE3727243A1 (de) *	1987-08-15	1989-02-23	Hoechst Ag	Verfahren zur enzymatischen herstellung optisch aktiver phosphorhaltiger funktioneller essigsaeurederivate
JP2655893B2 (ja) *	1988-10-20	1997-09-24	ユニチカ株式会社	光学活性なβ−ハロ乳酸又はグリシジル酸の合成法
NL8802849A (nl) *	1988-11-18	1990-06-18	Stamicarbon	Werkwijze voor de enantioselectieve bereiding van d-(-)-3-hal-methylpropionzuur of derivaten daarvan en de bereiding van captopril daaruit.
JPH02273196A (ja) *	1989-03-08	1990-11-07	Wisconsin Alumni Res Found	ラセミ化合物の生体触媒分割のエナンチオ選択性の改良法
FR2646669B1 (fr) *	1989-05-02	1991-07-05	Rhone Poulenc Chimie	Procede de separation enantiomeriquement selective des esters des acides halogeno-2 propioniques
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
US5420037A (en) *	1989-09-26	1995-05-30	E. R. Squibb & Sons, Inc.	Process for separation of enantiomeric 3-mercapto-2-substituted alkanoic acid using lipase P30 and synthesis of captopril type compounds
US5276151A (en) *	1990-02-01	1994-01-04	Emory University	Method of synthesis of 1,3-dioxolane nucleosides
HU210548B (en) *	1990-06-19	1995-05-29	Sandoz Ag	Process for preparing 2-tetrahydrofurane derivatives
US5338730A (en) *	1990-06-19	1994-08-16	Sandoz Ltd.	Use of the (R) isomer of 2-[(2-octa-decyloxymethyl-tetrahydro-2-furanylmethoxy)-hydroxyphosphinyloxy]-N,N,N-trimethylethanaminium hydroxide inner salt-4-oxide in treating multiple sclerosis
US5106736A (en) *	1991-04-23	1992-04-21	E.R. Squibb & Sons, Inc.	Enzymatic process for enantiomer-specific perparation of mercapto alkanoic acid compounds
AT398081B (de) *	1991-04-29	1994-09-26	Chemie Linz Gmbh	Verfahren zur enzymatischen hydrolyse eines carbonsäurederivates
DE4117255A1 (de) *	1991-05-27	1992-12-03	Chemie Linz Deutschland	Verfahren zur enzymatischen hydrolyse eines carbonsaeurederivates
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
EP0538693A3 (en) *	1991-10-23	1994-08-17	Squibb & Sons Inc	Stereoselective preparation of halophenyl alcohols
US5324662A (en) *	1992-05-15	1994-06-28	E. R. Squibb & Sons, Inc.	Stereoselective microbial or enzymatic reduction of 3,5-dioxo esters to 3-hydroxy-5-oxo, 3-oxo-5-hydroxy, and 3,5-dihydroxy esters
US5420337A (en) *	1992-11-12	1995-05-30	E. R. Squibb & Sons, Inc.	Enzymatic reduction method for the preparation of compounds useful for preparing taxanes
US6277879B1 (en)	1994-08-03	2001-08-21	Sarawak Medichem Pharmaceuticals, Inc.	Calanolide analogues and methods of their use
US6369241B1 (en)	1999-04-26	2002-04-09	Sarawak Medichem Pharmaceuticals, Inc.	Methods for preparing antiviral calanolide compounds
KR100613691B1 (ko) *	2004-09-07	2006-08-21	한국화학연구원	토양 메타게놈 유래 신규 리파제 및 이를 이용하여 라세믹에틸 2-브로모프로피오네이트를 선택적으로 분할하는 방법
CN100436399C (zh) *	2006-06-27	2008-11-26	浙江工业大学	一种制备(s)-(-)-2-氯丙酸酯和(r)-(+)-2-氯丙酸的方法
CN104262091A (zh) *	2014-10-09	2015-01-07	王同俊	R-1-(2,5-二甲基苯基)乙醇及其酯的合成
CN104262092A (zh) *	2014-10-09	2015-01-07	王同俊	R-1-(2-甲基苯基)乙醇及其酯的合成
CN104262093A (zh) *	2014-10-09	2015-01-07	王同俊	R-1-(3-甲基苯基)乙醇及其酯的合成
CN104262095A (zh) *	2014-10-12	2015-01-07	王同俊	R-1-(4-氟苯基)乙醇及其酯的合成
CN104262094A (zh) *	2014-10-12	2015-01-07	王同俊	一种r-1-(4-氯苯基)乙醇及其酯的合成方法
CN104262096A (zh) *	2014-10-12	2015-01-07	王同俊	一种r-1-(4-溴苯基)乙醇及其酯的合成方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2055802A (en) *	1979-08-07	1981-03-11	Ici Ltd	Process for the preparation of the optical isomers of alpha -chloro (or bromo) propionic acid esters
JPS5794295A (en) *	1980-12-04	1982-06-11	Sagami Chem Res Center	Preparation of optically active ester and/or acid

1985
- 1985-02-27 US US06/706,039 patent/US4601987A/en not_active Expired - Fee Related
1986
- 1986-02-11 NZ NZ215099A patent/NZ215099A/xx unknown
- 1986-02-25 YU YU00286/86A patent/YU28686A/xx unknown
- 1986-02-26 EP EP86201209A patent/EP0206436B1/en not_active Expired - Lifetime
- 1986-02-26 PL PL1986258141A patent/PL148128B1/pl unknown
- 1986-02-26 CZ CS861322A patent/CZ132286A3/cs unknown
- 1986-02-26 DE DE8686201209T patent/DE3682958D1/de not_active Expired - Lifetime
- 1986-02-26 AT AT86201209T patent/ATE70563T1/de not_active IP Right Cessation
- 1986-02-26 TR TR106/86A patent/TR23363A/xx unknown
- 1986-02-26 DD DD86287364A patent/DD258625A1/de unknown
- 1986-02-27 ZA ZA861473A patent/ZA861473B/xx unknown
- 1986-02-27 ES ES552498A patent/ES8705351A1/es not_active Expired
1987
- 1987-03-02 DD DD87300374A patent/DD260085A1/de not_active IP Right Cessation
- 1987-03-02 DD DD87300375A patent/DD260086A1/de not_active IP Right Cessation
- 1987-10-22 YU YU01945/87A patent/YU194587A/xx unknown
- 1987-10-22 YU YU01946/87A patent/YU194687A/xx unknown
1992
- 1992-11-03 CZ CS923296A patent/CZ329692A3/cs unknown
- 1992-11-03 SK SK3297-92A patent/SK329792A3/sk unknown
- 1992-11-03 SK SK3296-92A patent/SK329692A3/sk unknown
- 1992-11-03 CZ CS923297A patent/CZ329792A3/cs unknown

Also Published As

Publication number	Publication date
CZ132286A3 (en)	1994-11-16
SK329692A3 (en)	1995-02-08
PL148128B1 (en)	1989-09-30
ZA861473B (en)	1987-01-28
EP0206436B1 (en)	1991-12-18
US4601987A (en)	1986-07-22
DD260086A1 (de)	1988-09-14
ES8705351A1 (es)	1987-05-01
YU28686A (en)	1988-04-30
CZ329692A3 (en)	1993-06-16
ATE70563T1 (de)	1992-01-15
PL258141A1 (en)	1987-06-15
DE3682958D1 (de)	1992-01-30
CZ329792A3 (en)	1993-06-16
EP0206436A2 (en)	1986-12-30
YU194587A (en)	1988-10-31
DD258625A1 (de)	1988-07-27
YU194687A (en)	1988-06-30
DD260085A1 (de)	1988-09-14
EP0206436A3 (en)	1988-09-21
TR23363A (tr)	1989-12-28
NZ215099A (en)	1988-04-29
ES552498A0 (es)	1987-05-01

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