NO318758B1 - Fremgangsmate for enzymatisk opplosning av en racemisk blanding av stereospesifikke GABA-T-inhibitorer. - Google Patents
Fremgangsmate for enzymatisk opplosning av en racemisk blanding av stereospesifikke GABA-T-inhibitorer. Download PDFInfo
- Publication number
- NO318758B1 NO318758B1 NO19950157A NO950157A NO318758B1 NO 318758 B1 NO318758 B1 NO 318758B1 NO 19950157 A NO19950157 A NO 19950157A NO 950157 A NO950157 A NO 950157A NO 318758 B1 NO318758 B1 NO 318758B1
- Authority
- NO
- Norway
- Prior art keywords
- gaba
- formula
- compound
- enantiomer
- phenylacetyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 10
- 230000002255 enzymatic effect Effects 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 17
- 239000003112 inhibitor Substances 0.000 title abstract description 7
- 230000000707 stereoselective effect Effects 0.000 title abstract description 4
- 102100035923 4-aminobutyrate aminotransferase, mitochondrial Human genes 0.000 title description 7
- 101710115046 4-aminobutyrate aminotransferase, mitochondrial Proteins 0.000 title 1
- 108010073038 Penicillin Amidase Proteins 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 2
- 239000010410 layer Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 abstract description 42
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 abstract description 21
- PJDFLNIOAUIZSL-UHFFFAOYSA-N vigabatrin Chemical compound C=CC(N)CCC(O)=O PJDFLNIOAUIZSL-UHFFFAOYSA-N 0.000 abstract description 10
- 108090000340 Transaminases Proteins 0.000 abstract description 3
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 abstract description 2
- 102000003929 Transaminases Human genes 0.000 abstract description 2
- 238000001727 in vivo Methods 0.000 abstract description 2
- 108010060511 4-Aminobutyrate Transaminase Proteins 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 206010015037 epilepsy Diseases 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 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 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 206010010904 Convulsion Diseases 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000002427 irreversible effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- -1 vinyl GABA Chemical compound 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000020176 deacylation Effects 0.000 description 2
- 238000005947 deacylation reaction Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XWILORJMRMFKPM-ZCFIWIBFSA-N (4s)-4-aminohepta-5,6-dienoic acid Chemical compound C=C=C[C@@H](N)CCC(O)=O XWILORJMRMFKPM-ZCFIWIBFSA-N 0.000 description 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 1
- 102000004400 Aminopeptidases Human genes 0.000 description 1
- 108090000915 Aminopeptidases Proteins 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000008238 Muscle Spasticity Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 208000029650 alcohol withdrawal Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005282 allenyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 108010003977 aminoacylase I Proteins 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 239000011942 biocatalyst Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 102000014898 transaminase activity proteins Human genes 0.000 description 1
- 229960005318 vigabatrin Drugs 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
- 229940011671 vitamin b6 Drugs 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
-
- 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
- C12P13/001—Amines; Imines
-
- 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
-
- 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
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
- C12P41/007—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (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)
- Proteomics, Peptides & Aminoacids (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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/915,446 US5316944A (en) | 1992-07-17 | 1992-07-17 | Enzymatic resolution of a racemic mixture of gamma-amino acids using penicillin acylase |
| PCT/US1993/005737 WO1994002628A1 (en) | 1992-07-17 | 1993-06-15 | Enzymatic resolution of a racemic mixture of stereospecific gaba-t inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO950157L NO950157L (no) | 1995-01-16 |
| NO950157D0 NO950157D0 (no) | 1995-01-16 |
| NO318758B1 true NO318758B1 (no) | 2005-05-02 |
Family
ID=25435755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19950157A NO318758B1 (no) | 1992-07-17 | 1995-01-16 | Fremgangsmate for enzymatisk opplosning av en racemisk blanding av stereospesifikke GABA-T-inhibitorer. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5316944A (da) |
| EP (1) | EP0651821B1 (da) |
| JP (1) | JP3213717B2 (da) |
| KR (1) | KR100250100B1 (da) |
| AT (1) | ATE156860T1 (da) |
| AU (1) | AU662998B2 (da) |
| CA (1) | CA2136840C (da) |
| DE (1) | DE69313118T2 (da) |
| DK (1) | DK0651821T3 (da) |
| ES (1) | ES2106355T3 (da) |
| FI (1) | FI106266B (da) |
| GR (1) | GR3024491T3 (da) |
| HU (1) | HU216309B (da) |
| NO (1) | NO318758B1 (da) |
| NZ (1) | NZ253926A (da) |
| WO (1) | WO1994002628A1 (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001523969A (ja) * | 1997-05-01 | 2001-11-27 | ジー．ディー．サール アンド カンパニー | キラルベータアミノ酸の製造方法および製造装置 |
| NL1009814C2 (nl) * | 1998-08-06 | 2000-02-08 | Dsm Nv | Werkwijze voor de bereiding van een N-geacyleerd aminonitril. |
| US6897058B2 (en) | 2000-09-08 | 2005-05-24 | Dsm Ip Assets B.V. | Method for the preparation of enantiomerically enriched amines |
| WO2002020821A2 (en) * | 2000-09-08 | 2002-03-14 | Dsm N.V. | Process for the preparation of enantiomerically enriched amines |
| FR2853315B1 (fr) * | 2003-04-04 | 2006-07-07 | Solvay | Procede pour la fabrication de derives d'aminoacides |
| WO2014060925A2 (en) * | 2012-10-15 | 2014-04-24 | Mahesh Kandula | Compositions and methods for the treatment of neurological and neurodegenerative diseases |
| CN105777586A (zh) * | 2016-04-14 | 2016-07-20 | 安徽省逸欣铭医药科技有限公司 | S（+）氨己烯酸酯衍生物及其制备方法和用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2120244B (en) * | 1982-05-17 | 1985-05-01 | Merrell Toraude & Co | Aminoalkadiene derivative |
| DE3247764A1 (de) * | 1982-12-23 | 1984-06-28 | Ernst Leitz Wetzlar Gmbh, 6330 Wetzlar | Fotografische kamera |
| GB2133002B (en) * | 1982-12-30 | 1986-01-29 | Merrell Toraude & Co | Process for preparing 4-amino-5-hexenoic acid |
| US4636470A (en) * | 1984-08-17 | 1987-01-13 | Stauffer Chemical Company | Resolution of racemates of amino acids |
-
1992
- 1992-07-17 US US07/915,446 patent/US5316944A/en not_active Expired - Lifetime
-
1993
- 1993-06-15 EP EP93915370A patent/EP0651821B1/en not_active Expired - Lifetime
- 1993-06-15 NZ NZ253926A patent/NZ253926A/en not_active IP Right Cessation
- 1993-06-15 DE DE69313118T patent/DE69313118T2/de not_active Expired - Lifetime
- 1993-06-15 AU AU45377/93A patent/AU662998B2/en not_active Expired
- 1993-06-15 JP JP50445294A patent/JP3213717B2/ja not_active Expired - Lifetime
- 1993-06-15 CA CA002136840A patent/CA2136840C/en not_active Expired - Lifetime
- 1993-06-15 AT AT93915370T patent/ATE156860T1/de active
- 1993-06-15 KR KR1019950700170A patent/KR100250100B1/ko not_active IP Right Cessation
- 1993-06-15 HU HU9500129A patent/HU216309B/hu unknown
- 1993-06-15 DK DK93915370.6T patent/DK0651821T3/da active
- 1993-06-15 WO PCT/US1993/005737 patent/WO1994002628A1/en active IP Right Grant
- 1993-06-15 ES ES93915370T patent/ES2106355T3/es not_active Expired - Lifetime
-
1995
- 1995-01-13 FI FI950155A patent/FI106266B/fi not_active IP Right Cessation
- 1995-01-16 NO NO19950157A patent/NO318758B1/no not_active IP Right Cessation
-
1997
- 1997-08-21 GR GR970402130T patent/GR3024491T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ253926A (en) | 1996-10-28 |
| ES2106355T3 (es) | 1997-11-01 |
| CA2136840C (en) | 1997-01-14 |
| CA2136840A1 (en) | 1994-02-03 |
| DK0651821T3 (da) | 1997-09-01 |
| WO1994002628A1 (en) | 1994-02-03 |
| DE69313118D1 (de) | 1997-09-18 |
| GR3024491T3 (en) | 1997-11-28 |
| ATE156860T1 (de) | 1997-08-15 |
| FI950155A0 (fi) | 1995-01-13 |
| JPH07509132A (ja) | 1995-10-12 |
| US5316944A (en) | 1994-05-31 |
| HU9500129D0 (en) | 1995-05-29 |
| KR100250100B1 (ko) | 2000-03-15 |
| HUT70466A (en) | 1995-10-30 |
| HU216309B (hu) | 1999-06-28 |
| KR950702638A (ko) | 1995-07-29 |
| EP0651821A1 (en) | 1995-05-10 |
| DE69313118T2 (de) | 1997-12-11 |
| AU4537793A (en) | 1994-02-14 |
| EP0651821B1 (en) | 1997-08-13 |
| NO950157L (no) | 1995-01-16 |
| FI106266B (fi) | 2000-12-29 |
| NO950157D0 (no) | 1995-01-16 |
| FI950155A (fi) | 1995-01-13 |
| AU662998B2 (en) | 1995-09-21 |
| JP3213717B2 (ja) | 2001-10-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |