NL8005738A - Werkwijze voor de bereiding van de carbamylderivaten van alfa-hydroxyzuren alsmede van de overeenkomstige alfa-hydroxyzuren. - Google Patents

Werkwijze voor de bereiding van de carbamylderivaten van alfa-hydroxyzuren alsmede van de overeenkomstige alfa-hydroxyzuren. Download PDF

Info

Publication number: NL8005738A
Authority: NL; Netherlands
Prior art keywords: pseudomonas; oxazolidinedione; substituted; hydrolysis; process according
Prior art date: 1979-10-17

Application number

NL8005738A

Other languages

English (en)

Dutch (nl)

Original Assignee

Eni Ente Naz Idrocarb

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.)

1979-10-17

Filing date

1980-10-17

Publication date

1981-04-22

1980-10-17 Application filed by Eni Ente Naz Idrocarb filed Critical Eni Ente Naz Idrocarb

1981-04-22 Publication of NL8005738A publication Critical patent/NL8005738A/nl

Links

239000002253 acid Substances 0.000 title description 3
150000007513 acids Chemical class 0.000 title 2
QGLZXHRNAYXIBU-UHFFFAOYSA-N aldicarb Chemical class CNC(=O)ON=CC(C)(C)SC QGLZXHRNAYXIBU-UHFFFAOYSA-N 0.000 title 1
238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims description 19
230000007062 hydrolysis Effects 0.000 claims description 11
238000006460 hydrolysis reaction Methods 0.000 claims description 11
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 9
244000005700 microbiome Species 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 claims description 7
230000000707 stereoselective effect Effects 0.000 claims description 7
101100099821 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cbs-1 gene Proteins 0.000 claims description 5
241000589774 Pseudomonas sp. Species 0.000 claims description 5
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 4
241000589516 Pseudomonas Species 0.000 claims description 4
244000309466 calf Species 0.000 claims description 4
239000001963 growth medium Substances 0.000 claims description 4
210000004185 liver Anatomy 0.000 claims description 4
229960002510 mandelic acid Drugs 0.000 claims description 4
230000007071 enzymatic hydrolysis Effects 0.000 claims description 3
238000006047 enzymatic hydrolysis reaction Methods 0.000 claims description 3
239000000758 substrate Substances 0.000 claims description 3
241000590020 Achromobacter Species 0.000 claims description 2
241000186046 Actinomyces Species 0.000 claims description 2
241000589158 Agrobacterium Species 0.000 claims description 2
241000589155 Agrobacterium tumefaciens Species 0.000 claims description 2
241000186063 Arthrobacter Species 0.000 claims description 2
241000193830 Bacillus <bacterium> Species 0.000 claims description 2
241000193764 Brevibacillus brevis Species 0.000 claims description 2
241000222120 Candida <Saccharomycetales> Species 0.000 claims description 2
241000186216 Corynebacterium Species 0.000 claims description 2
241001600125 Delftia acidovorans Species 0.000 claims description 2
241000193385 Geobacillus stearothermophilus Species 0.000 claims description 2
241000588748 Klebsiella Species 0.000 claims description 2
241000192041 Micrococcus Species 0.000 claims description 2
241000586779 Protaminobacter Species 0.000 claims description 2
241000588769 Proteus <enterobacteria> Species 0.000 claims description 2
241000589540 Pseudomonas fluorescens Species 0.000 claims description 2
241000192023 Sarcina Species 0.000 claims description 2
241000607720 Serratia Species 0.000 claims description 2
241000187747 Streptomyces Species 0.000 claims description 2
238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical compound O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 claims 4
239000013543 active substance Substances 0.000 claims 3
241000186146 Brevibacterium Species 0.000 claims 1
241001236817 Paecilomyces <Clavicipitaceae> Species 0.000 claims 1
241000235648 Pichia Species 0.000 claims 1
241000223252 Rhodotorula Species 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000284 extract Substances 0.000 description 5
235000013372 meat Nutrition 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
150000001261 hydroxy acids Chemical class 0.000 description 4
239000002609 medium Substances 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
UBNRGKDXTQNNLW-OGFXRTJISA-N carbamic acid (2R)-2-hydroxy-2-phenylacetic acid Chemical compound NC(O)=O.O[C@@H](C(O)=O)c1ccccc1 UBNRGKDXTQNNLW-OGFXRTJISA-N 0.000 description 3
239000008103 glucose Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
SBYYYVAMWBVIIX-UHFFFAOYSA-N 5-phenyl-1,3-oxazolidine-2,4-dione Chemical compound O1C(=O)NC(=O)C1C1=CC=CC=C1 SBYYYVAMWBVIIX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000001888 Peptone Substances 0.000 description 2
108010080698 Peptones Proteins 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 2
235000011180 diphosphates Nutrition 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
235000019319 peptone Nutrition 0.000 description 2
239000000843 powder Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241001467578 Microbacterium Species 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000589776 Pseudomonas putida Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
210000001557 animal structure Anatomy 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
150000001277 beta hydroxy acids Chemical class 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000012531 culture fluid Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
229940091173 hydantoin Drugs 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000003100 immobilizing effect Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
229910052500 inorganic mineral Chemical class 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000011707 mineral Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000002888 oleic acid derivatives Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000001475 oxazolidinediones Chemical class 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Microbiology (AREA)
General Chemical & Material Sciences (AREA)
Biotechnology (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NL8005738A 1979-10-17 1980-10-17 Werkwijze voor de bereiding van de carbamylderivaten van alfa-hydroxyzuren alsmede van de overeenkomstige alfa-hydroxyzuren. NL8005738A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT2654779		1979-10-17
IT26547/79A IT1125486B (it)	1979-10-17	1979-10-17	Processo per la preparazione di carbamil derivati di alfa-idrossiacidi e dei corrispondenti alfa-idrossiacidi

Publications (1)

Publication Number	Publication Date
NL8005738A true NL8005738A (nl)	1981-04-22

Family

ID=11219745

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8005738A NL8005738A (nl)	1979-10-17	1980-10-17	Werkwijze voor de bereiding van de carbamylderivaten van alfa-hydroxyzuren alsmede van de overeenkomstige alfa-hydroxyzuren.

Country Status (20)

Country	Link
US (2)	US4332905A (fr)
JP (1)	JPS5685288A (fr)
AT (1)	AT373914B (fr)
AU (1)	AU540872B2 (fr)
BE (1)	BE885587A (fr)
BR (1)	BR8006668A (fr)
CA (1)	CA1146889A (fr)
CH (1)	CH652418A5 (fr)
DE (1)	DE3039132C2 (fr)
DK (1)	DK161718C (fr)
ES (2)	ES496505A0 (fr)
FI (1)	FI71167C (fr)
FR (1)	FR2467843B1 (fr)
GB (1)	GB2061269B (fr)
IE (1)	IE50297B1 (fr)
IT (1)	IT1125486B (fr)
LU (1)	LU82827A1 (fr)
NL (1)	NL8005738A (fr)
NO (1)	NO155698C (fr)
SE (1)	SE8007282L (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4415657A (en) *	1980-12-30	1983-11-15	Kanegafuchi Chemical Industry Company, Limited	Process for preparation of an optically active monoalkyl ester of β-(S)-aminoglutaric acid
JPS5931693A (ja) *	1982-08-13	1984-02-20	Kanegafuchi Chem Ind Co Ltd	光学活性オキサゾリジノン誘導体の製造方法
JP2542941B2 (ja) *	1990-02-02	1996-10-09	チッソ株式会社	光学活性ヒドロキシラクトン類の製造方法
WO1994018181A1 (fr) *	1993-02-01	1994-08-18	Monsanto Company	Procede de preparation de n-substitue-oxazolidine-2,4-diones

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1220422B (de) *	1963-09-07	1966-07-07	Merck Ag E	Verfahren zur Herstellung eines neuen Bis-pyridyl-methyl-disulfids
US4065353A (en) *	1975-05-12	1977-12-27	Snamprogetti, S.P.A.	Method for the preparation of D-carbamyl aminoacids and the corresponding D-aminoacids
JPS5391189A (en) *	1976-12-30	1978-08-10	Kanegafuchi Chem Ind Co Ltd	Preparation of d-n-carbamoyl-alpha-amino acids
JPS557001A (en) *	1978-03-15	1980-01-18	Kanegafuchi Chem Ind Co Ltd	Preparation of n-carbamoyl-d-thienylglycine

1979
- 1979-10-17 IT IT26547/79A patent/IT1125486B/it active
1980
- 1980-09-16 AU AU62446/80A patent/AU540872B2/en not_active Ceased
- 1980-09-17 IE IE1948/80A patent/IE50297B1/en not_active IP Right Cessation
- 1980-09-17 US US06/188,074 patent/US4332905A/en not_active Expired - Lifetime
- 1980-09-17 DK DK394580A patent/DK161718C/da not_active IP Right Cessation
- 1980-09-18 CA CA000360509A patent/CA1146889A/fr not_active Expired
- 1980-09-29 GB GB8031391A patent/GB2061269B/en not_active Expired
- 1980-09-30 FI FI803116A patent/FI71167C/fi not_active IP Right Cessation
- 1980-10-01 CH CH7331/80A patent/CH652418A5/it not_active IP Right Cessation
- 1980-10-07 FR FR8021444A patent/FR2467843B1/fr not_active Expired
- 1980-10-07 AT AT0498280A patent/AT373914B/de not_active IP Right Cessation
- 1980-10-07 LU LU82827A patent/LU82827A1/fr unknown
- 1980-10-08 BE BE0/202375A patent/BE885587A/fr not_active IP Right Cessation
- 1980-10-15 BR BR8006668A patent/BR8006668A/pt unknown
- 1980-10-15 NO NO803080A patent/NO155698C/no unknown
- 1980-10-16 DE DE3039132A patent/DE3039132C2/de not_active Expired
- 1980-10-16 SE SE8007282A patent/SE8007282L/ unknown
- 1980-10-16 JP JP14374780A patent/JPS5685288A/ja active Pending
- 1980-10-17 NL NL8005738A patent/NL8005738A/nl not_active Application Discontinuation
- 1980-10-17 ES ES496505A patent/ES496505A0/es active Granted
1981
- 1981-12-15 ES ES508579A patent/ES508579A0/es active Granted
1982
- 1982-02-16 US US06/348,707 patent/US4489208A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA1146889A (fr)	1983-05-24
FR2467843A1 (fr)	1981-04-30
ES8306467A1 (es)	1983-06-01
NO155698B (no)	1987-02-02
DK161718B (da)	1991-08-05
NO155698C (no)	1987-05-13
FI71167B (fi)	1986-08-14
FI71167C (fi)	1986-11-24
ATA498280A (de)	1983-07-15
FR2467843B1 (fr)	1986-04-25
IT7926547A0 (it)	1979-10-17
CH652418A5 (it)	1985-11-15
GB2061269A (en)	1981-05-13
AU6244680A (en)	1982-08-26
DE3039132C2 (de)	1982-09-02
US4489208A (en)	1984-12-18
ES8205017A1 (es)	1982-05-16
US4332905A (en)	1982-06-01
ES496505A0 (es)	1982-05-16
AU540872B2 (en)	1984-12-06
IE50297B1 (en)	1986-03-19
FI803116A7 (fi)	1981-04-18
GB2061269B (en)	1983-09-28
BR8006668A (pt)	1981-04-22
DK161718C (da)	1992-01-20
BE885587A (fr)	1981-04-08
JPS5685288A (en)	1981-07-11
LU82827A1 (fr)	1981-06-04
AT373914B (de)	1984-03-12
IT1125486B (it)	1986-05-14
SE8007282L (sv)	1981-04-18
ES508579A0 (es)	1983-06-01
NO803080L (no)	1981-04-21
DK394580A (da)	1981-04-18
IE801948L (en)	1981-04-17
DE3039132A1 (de)	1981-04-30

Legal Events

Date	Code	Title
1982-09-01	BA	A request for search or an international-type search has been filed
1982-09-01	BB	A search report has been drawn up
1985-01-01	A85	Still pending on 85-01-01
1986-09-01	BC	A request for examination has been filed
1995-06-01	BV	The patent application has lapsed

Publication	Publication Date	Title
NL192118C (nl)	1997-02-04	Enzymatische microbiologische werkwijze voor de bereiding van optisch aktieve aminozuren uit hydanthoinen en/of racemische carbamoylverbindin- gen.
FI95397B (fi)	1995-10-13	Menetelmä (S)-ketoprofeenin valmistamiseksi
US4629701A (en)	1986-12-16	Process for preparing optically active carboxylic acids and antipode esters thereof
JPH0342074B2 (fr)	1991-06-26
NL8005738A (nl)	1981-04-22	Werkwijze voor de bereiding van de carbamylderivaten van alfa-hydroxyzuren alsmede van de overeenkomstige alfa-hydroxyzuren.
US4242452A (en)	1980-12-30	Process for preparing N-carbamoyl-D-thienylglycines
JPH0260599A (ja)	1990-03-01	酵素分解方法
JPS60180596A (ja)	1985-09-14	Ｌ‐α‐アミノ酸の製法
US4584270A (en)	1986-04-22	Process for preparing optically-active 4-amino-3-hydroxybutyric acid
JP2693555B2 (ja)	1997-12-24	ジオキシゲナーゼおよびその製造方法
US3139386A (en)	1964-06-30	Method for producing l-methionine
JPS58201992A (ja)	1983-11-25	微生物によるβ−置換プロピオン酸またはそのアミドの製造法
JPS5857156B2 (ja)	1983-12-19	発酵法によるコエンチ−ムｑ↓１↓０の製造法
JPH0870878A (ja)	1996-03-19	トロポロニルアラニンの製造法
JPH01228489A (ja)	1989-09-12	Ｄ−Ｎ−カルバミル−α−アミノ酸の製造法
JPH0525476B2 (fr)	1993-04-13
JPH01181797A (ja)	1989-07-19	Ｄ−スレオ−３−（３，４−ジヒドロキシフェニル）セリン誘導体の製造法
JPS61152292A (ja)	1986-07-10	Ｌ−セリンの製造法
JPS63107946A (ja)	1988-05-12	光学活性なビフェニル誘導体およびその製造法
JPH0455674B2 (fr)	1992-09-04
JPS60256393A (ja)	1985-12-18	分枝鎖脂肪又は芳香族ｌ‐アミノ酸の発酵的製法
JPH01191697A (ja)	1989-08-01	光学活性カルボン酸及びその対掌体エステルの製造法
JPH0394696A (ja)	1991-04-19	光学活性体の製造方法
JPH01191696A (ja)	1989-08-01	光学活性カルボン酸及びその対掌体エステルの製造法
JPH0353915B2 (fr)	1991-08-16