NO315750B1 - Resolusjon av arylalkansyrer - Google Patents

Resolusjon av arylalkansyrer Download PDF

Info

Publication number: NO315750B1
Authority: NO; Norway
Prior art keywords: ketoprofen; biotransformation; enantiomer; ester; acid
Prior art date: 1991-08-22

Application number

NO19940570A

Other languages

English (en)

Norwegian (no)

Other versions

NO940570D0 (no

NO940570L (no

Inventor

Christopher Thomas Evans

Richard Anthony Wisdom

Peter Joseph Stabler

Germano Carganico

Original Assignee

Menarini Lab

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.)

1991-08-22

Filing date

1994-02-18

Publication date

2003-10-20

1994-02-18 Application filed by Menarini Lab filed Critical Menarini Lab

1994-02-18 Publication of NO940570D0 publication Critical patent/NO940570D0/no

1994-02-18 Publication of NO940570L publication Critical patent/NO940570L/no

2003-10-20 Publication of NO315750B1 publication Critical patent/NO315750B1/no

Links

239000002253 acid Substances 0.000 title claims description 13
150000007513 acids Chemical class 0.000 title description 3
238000000034 method Methods 0.000 claims description 13
DKYWVDODHFEZIM-NSHDSACASA-N dexketoprofen Chemical compound OC(=O)[C@@H](C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-NSHDSACASA-N 0.000 claims description 12
DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 12
102000004190 Enzymes Human genes 0.000 claims description 8
108090000790 Enzymes Proteins 0.000 claims description 8
239000011942 biocatalyst Substances 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 6
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 description 2
241000223230 Trichosporon Species 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims 3
DKYWVDODHFEZIM-LLVKDONJSA-N (2r)-2-(3-benzoylphenyl)propanoic acid Chemical compound OC(=O)[C@H](C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-LLVKDONJSA-N 0.000 claims 1
125000004494 ethyl ester group Chemical group 0.000 claims 1
125000004492 methyl ester group Chemical group 0.000 claims 1
244000005700 microbiome Species 0.000 claims 1
230000036983 biotransformation Effects 0.000 description 22
229960002783 dexketoprofen Drugs 0.000 description 11
230000000694 effects Effects 0.000 description 9
229960000991 ketoprofen Drugs 0.000 description 8
239000002609 medium Substances 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000012010 growth Effects 0.000 description 6
PXTPHOZOKYFBLV-UHFFFAOYSA-N 2-(3-benzoylphenyl)-2-methylbutanoic acid Chemical compound CCC(C)(C(O)=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 PXTPHOZOKYFBLV-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
239000008272 agar Substances 0.000 description 3
239000001963 growth medium Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
241000223231 Trichosporon beigelii Species 0.000 description 2
238000005273 aeration Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000007423 decrease Effects 0.000 description 2
CQSMNXCTDMLMLM-UHFFFAOYSA-N ethyl 2-(3-benzoylphenyl)propanoate Chemical compound CCOC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 CQSMNXCTDMLMLM-UHFFFAOYSA-N 0.000 description 2
239000008103 glucose Substances 0.000 description 2
238000011835 investigation Methods 0.000 description 2
-1 ketoprofen ester Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
235000013619 trace mineral Nutrition 0.000 description 2
239000011573 trace mineral Substances 0.000 description 2
HGRGFZWEVKNHJT-UHFFFAOYSA-N 2-(3-benzoylphenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 HGRGFZWEVKNHJT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000178951 Endomyces Species 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
230000009603 aerobic growth Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
230000002210 biocatalytic effect Effects 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000010367 cloning Methods 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
238000004090 dissolution Methods 0.000 description 1
238000010931 ester hydrolysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
241000894007 species Species 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
IERBVBGUKBHALB-UHFFFAOYSA-K tripotassium;phosphate;dihydrate Chemical compound O.O.[K+].[K+].[K+].[O-]P([O-])([O-])=O IERBVBGUKBHALB-UHFFFAOYSA-K 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero 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
- 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
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- 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
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/44—Polycarboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Genetics & Genomics (AREA)
General Chemical & Material Sciences (AREA)
Biotechnology (AREA)
Microbiology (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)

NO19940570A 1991-08-22 1994-02-18 Resolusjon av arylalkansyrer NO315750B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB919118149A GB9118149D0 (en)	1991-08-22	1991-08-22	Araylalkanoic acid resolution
PCT/EP1992/001892 WO1993004189A1 (en)	1991-08-22	1992-08-19	Arylalkanoic acid resolution

Publications (3)

Publication Number	Publication Date
NO940570D0 NO940570D0 (no)	1994-02-18
NO940570L NO940570L (no)	1994-02-18
NO315750B1 true NO315750B1 (no)	2003-10-20

Family

ID=10700381

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19940570A NO315750B1 (no)	1991-08-22	1994-02-18	Resolusjon av arylalkansyrer

Country Status (22)

Country	Link
US (1)	US5516690A (bg)
EP (1)	EP0599967B1 (bg)
JP (1)	JP3174328B2 (bg)
KR (1)	KR100240696B1 (bg)
AT (1)	ATE161053T1 (bg)
AU (1)	AU662556B2 (bg)
BG (1)	BG62056B1 (bg)
CA (1)	CA2116003C (bg)
CZ (1)	CZ283141B6 (bg)
DE (2)	DE599967T1 (bg)
DK (1)	DK0599967T3 (bg)
ES (1)	ES2058047T3 (bg)
FI (1)	FI103807B (bg)
GB (1)	GB9118149D0 (bg)
GR (2)	GR940300068T1 (bg)
HU (1)	HU213748B (bg)
NO (1)	NO315750B1 (bg)
RO (1)	RO115970B1 (bg)
RU (1)	RU2119955C1 (bg)
SK (1)	SK280179B6 (bg)
UA (1)	UA27817C2 (bg)
WO (1)	WO1993004189A1 (bg)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5912164A (en) *	1993-03-03	1999-06-15	Laboratorios Menarini S.A.	Stereoselective hydrolysis of chiral carboxylic acid esters using esterase from ophiostoma or ceratocystis
GB9304256D0 (en) *	1993-03-03	1993-04-21	Chiros Ltd	Arylalkanoic acid resolution
GB9304351D0 (en) *	1993-03-03	1993-04-21	Chiros Ltd	Arylalkanoic acid resolution and microorganisms for use therein
US6242243B1 (en) *	1998-03-30	2001-06-05	Council Of Scientific & Industrial Research	Trichosporon sp RRLY-15 (DSM 11829) and its use to prepare S(+)-6-methoxy-methyl-2-naphthalene acetic acid
US20030059903A1 (en) *	2001-04-03	2003-03-27	Degussa Ag	Process for the production of L-amino acids using strains of the family enterobacteriaceae that contain an attenuated aceA gene
US7223582B2 (en) *	2002-01-17	2007-05-29	Korea Research Institute Of Bioscience And Biotechnology	Esterase, its DNA, its overexpression and production of optically active aryl propionic acids using the same
JP6306188B2 (ja) *	2013-12-16	2018-04-04	ゾエティス・サービシーズ・エルエルシー	長時間作用型ケトプロフェン組成物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3680132D1 (de) *	1985-04-01	1991-08-14	Kanegafuchi Chemical Ind	Verfahren zur herstellung von optisch aktiver indolin-2-carbonsaeure.
HU197942B (en) *	1985-12-20	1989-06-28	Wisconsin Alumni Res Found	Process for producing (s)-alpha-methyl-aryl-acetic acids
US5322791A (en) *	1985-12-20	1994-06-21	Wisconsin Alumni Research Foundation	Process for preparing (S)-α-methylarylacetic acids
US4857469A (en) *	1987-04-09	1989-08-15	Toyo Jozo Co., Ltd.	Process for preparing optically active mercapto compound
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
ATE151813T1 (de) *	1990-02-26	1997-05-15	Rhone Poulenc Inc	Stereospezifische trennung durch hydrolyse von 2- arylpropionsäureestern mit leberenzymen

1991
- 1991-08-22 GB GB919118149A patent/GB9118149D0/en active Pending
1992
- 1992-08-19 DE DE0599967T patent/DE599967T1/de active Pending
- 1992-08-19 AU AU24685/92A patent/AU662556B2/en not_active Expired
- 1992-08-19 CZ CZ94364A patent/CZ283141B6/cs not_active IP Right Cessation
- 1992-08-19 WO PCT/EP1992/001892 patent/WO1993004189A1/en active IP Right Grant
- 1992-08-19 RU RU94015601A patent/RU2119955C1/ru active
- 1992-08-19 CA CA002116003A patent/CA2116003C/en not_active Expired - Lifetime
- 1992-08-19 UA UA94005318A patent/UA27817C2/uk unknown
- 1992-08-19 HU HU9400462A patent/HU213748B/hu unknown
- 1992-08-19 SK SK176-94A patent/SK280179B6/sk not_active IP Right Cessation
- 1992-08-19 KR KR1019940700492A patent/KR100240696B1/ko not_active IP Right Cessation
- 1992-08-19 US US08/193,004 patent/US5516690A/en not_active Expired - Lifetime
- 1992-08-19 EP EP92918204A patent/EP0599967B1/en not_active Expired - Lifetime
- 1992-08-19 ES ES92918204T patent/ES2058047T3/es not_active Expired - Lifetime
- 1992-08-19 JP JP51163292A patent/JP3174328B2/ja not_active Expired - Lifetime
- 1992-08-19 RO RO94-00247A patent/RO115970B1/ro unknown
- 1992-08-19 DK DK92918204T patent/DK0599967T3/da active
- 1992-08-19 AT AT92918204T patent/ATE161053T1/de active
- 1992-08-19 DE DE69223516T patent/DE69223516T2/de not_active Expired - Lifetime
1994
- 1994-02-16 BG BG98484A patent/BG62056B1/bg unknown
- 1994-02-18 NO NO19940570A patent/NO315750B1/no not_active IP Right Cessation
- 1994-02-18 FI FI940792A patent/FI103807B/fi not_active IP Right Cessation
- 1994-10-31 GR GR940300068T patent/GR940300068T1/el unknown
1998
- 1998-03-06 GR GR980400474T patent/GR3026303T3/el unknown

Also Published As

Publication number	Publication date
EP0599967B1 (en)	1997-12-10
WO1993004189A1 (en)	1993-03-04
AU2468592A (en)	1993-03-16
FI940792A (fi)	1994-02-18
HUT69778A (en)	1995-09-28
CA2116003A1 (en)	1993-03-04
GR940300068T1 (en)	1994-10-31
DK0599967T3 (da)	1998-08-24
CA2116003C (en)	2004-11-16
NO940570D0 (no)	1994-02-18
KR100240696B1 (ko)	2000-01-15
UA27817C2 (uk)	2000-10-16
BG98484A (bg)	1994-01-03
GR3026303T3 (en)	1998-06-30
CZ283141B6 (cs)	1998-01-14
DE69223516D1 (de)	1998-01-22
NO940570L (no)	1994-02-18
SK17694A3 (en)	1995-02-08
EP0599967A1 (en)	1994-06-08
ES2058047T3 (es)	1998-01-16
FI103807B1 (fi)	1999-09-30
GB9118149D0 (en)	1991-10-09
US5516690A (en)	1996-05-14
RU94015601A (ru)	1996-07-10
HU9400462D0 (en)	1994-06-28
JPH06510182A (ja)	1994-11-17
DE69223516T2 (de)	1998-05-20
JP3174328B2 (ja)	2001-06-11
RO115970B1 (ro)	2000-08-30
ES2058047T1 (es)	1994-11-01
FI940792A0 (fi)	1994-02-18
HU213748B (en)	1997-09-29
AU662556B2 (en)	1995-09-07
FI103807B (fi)	1999-09-30
SK280179B6 (sk)	1999-09-10
DE599967T1 (de)	1995-06-14
ATE161053T1 (de)	1997-12-15
RU2119955C1 (ru)	1998-10-10
CZ36494A3 (en)	1994-08-17
BG62056B1 (bg)	1999-01-29

Legal Events

Date	Code	Title	Description
2012-09-10	MK1K	Patent expired

Publication	Publication Date	Title
JP3717535B2 (ja)	2005-11-16	新規微生物およびＬ−α−アミノ酸の製法
EP0195717A2 (en)	1986-09-24	Process for the biotechnological preparation of optically active alpha-arylalkanoic acids
NO147570B (no)	1983-01-24	Fremgangsmaate for fremstilling av d-fenylglycin ved enzymatisk omdannelse av d,l-fenylhydantoin
Ushio et al.	1986	Stereochemical control in microbial reduction 4. Effect of cultivation conditions on the reduction of β-keto esters by methylotrophic yeasts.
DK165124B (da)	1992-10-12	Fremgangsmaade til fremstilling af en 5-hydroxy-s541-macrolidforbindelse
NO315750B1 (no)	2003-10-20	Resolusjon av arylalkansyrer
WO2017016199A1 (zh)	2017-02-02	一种沙链霉菌的用途及香兰素的生产方法
JP3694065B2 (ja)	2005-09-14	環状Ｓ−α−アミノカルボン酸およびＲ−α−アミノカルボキサミドの生物工学的製造方法
KR0136574B1 (ko)	1998-04-25	발효에 의한 2-(4-히드록시페녹시)프로피온산의 제조 방법
KR20100043230A (ko)	2010-04-28	에틸-3,4-에폭시부티레이트의 미생물에 의한 동적 분리
DK171744B1 (da)	1997-04-28	Fremgangsmåde til fremstilling af pyrodruesyre
JPH01104195A (ja)	1989-04-21	２−アリールオキシプロピオン酸の製造方法
JPH04234991A (ja)	1992-08-24	新規微生物
BE824987A (fr)	1975-05-15	Procede pour la preparation de la beta-ergocriptine
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