KR850001151A - r-알레닐-r-아미노부티르산의 제조방법 - Google Patents
r-알레닐-r-아미노부티르산의 제조방법 Download PDFInfo
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- KR850001151A KR850001151A KR1019840003936A KR840003936A KR850001151A KR 850001151 A KR850001151 A KR 850001151A KR 1019840003936 A KR1019840003936 A KR 1019840003936A KR 840003936 A KR840003936 A KR 840003936A KR 850001151 A KR850001151 A KR 850001151A
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- acid
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- 238000000034 method Methods 0.000 title claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 14
- 239000002253 acid Substances 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- IDKITPVRIHWVDP-UHFFFAOYSA-N 4-azaniumylocta-5,6-dienoate Chemical compound CC=C=CC(N)CCC(O)=O IDKITPVRIHWVDP-UHFFFAOYSA-N 0.000 claims 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 230000002862 amidating effect Effects 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- -1 phosphorus compound Chemical class 0.000 claims 2
- JHGBTLOBGZXLOW-UHFFFAOYSA-N 4-amino-5-methylhepta-5,6-dienoic acid Chemical compound C=C=C(C)C(N)CCC(O)=O JHGBTLOBGZXLOW-UHFFFAOYSA-N 0.000 claims 1
- BRQOJNOREYSFHX-UHFFFAOYSA-N 4-amino-7-bromohepta-5,6-dienoic acid Chemical compound OC(=O)CCC(N)C=C=CBr BRQOJNOREYSFHX-UHFFFAOYSA-N 0.000 claims 1
- KRNBGPNMGGACJK-UHFFFAOYSA-N 4-amino-7-chloro-5-methylhepta-5,6-dienoic acid Chemical compound ClC=C=C(C)C(N)CCC(O)=O KRNBGPNMGGACJK-UHFFFAOYSA-N 0.000 claims 1
- SYSJROGBRPXYML-UHFFFAOYSA-N 4-amino-7-chlorohepta-5,6-dienoic acid Chemical compound OC(=O)CCC(N)C=C=CCl SYSJROGBRPXYML-UHFFFAOYSA-N 0.000 claims 1
- XWILORJMRMFKPM-UHFFFAOYSA-N 4-aminohepta-5,6-dienoic acid Chemical compound C=C=CC(N)CCC(O)=O XWILORJMRMFKPM-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical class CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/30—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
Abstract
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Description
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Claims (18)
- 일반식(IA) 화합물을 가수분해하거나; R5가 하이드록시인 일반식(I) 화합물의 유리산을 에스테르화하거나; R5가 하이드록시인 일반식(I) 화합물을 아미드화하거나; R4가 수소인 일반식(I) 화합물을 아미드화하거나; 일반식(I) 화합물의 유리염기를 산과 반응시켜 약학적으로 허용되는 산부가염으로 전환시키거나; 일반식(I) 화합물의 유리산을 염기와 반응시켜 약학적으로 허용되는 산성염으로 전환시키거나; 산성염을 산과 반응시켜 상응하는 유리산으로 전환시키거나; 에스테르를 산과 반응시켜 유리산으로, 또는 염기와 반응시켜 상응하는 약학적으로 허용되는 염으로 전환시키거나; 아미드를 염기와 반응시켜 아민으로, 또는 산과 반응시켜 산부가염으로 전환시킴을 특징으로 하여 일반식(I) 화합물 및 그의 약학적으로 허용되는 염을 제조하는 방법.상기 식에서,R1은 수소, 할로, C1내지 C4알킬, C7내지 C9알킬페닐 또는 치환된 페닐 또는 C7내지 C9알킬페닐(여기에서 치환체는 할로, C1내지 C4알킬, C1내지 C4알콕시, C1내지 C4티오알킬 또는 C1내지 C4아미노알킬이다), 또는 C1내지 C4설포닐- 또는 설포실알킬, 설포닐- 또는 설폭실아릴, 또는 C1내지 C4설포닐- 또는 설폭실 할로알킬이고;R2및 R3은 독립적으로 수소, 할로, C1내지 C4알킬, C7내지 C9알킬페닐 또는 치환된 페닐 또는 C7내지 C9알킬페닐 (여기에서 치환체는 할로, C1내지 C4알킬 C1내지 C4알콕시,C1내지 C4디오알킬,또는 C1내지 C4아미노알킬이다)이고:R4는 수소, 알킬부분이 C1내지 C22알킬카보닐, 알콕시부분이 C1내지 C22인 알콕시카보닐 또는 다음 일반식(II)의 그룹이고,(여기에서, R6은 수소, C1내지 C4알킬, 벤질 또는 p-하이드록시벤질이다);R5는 하이드록실, C1내지 C22알콕시, C1내지 C22알킬아미노 또는 다음 일반식(III)의 그룹이며,(여기에서, R7은 수소, C1내지 C4알킬, 벤질 또는 p-하이드록시벤질이다);A는 -CH=CH- 또는 일반식(IV)의 그룹이다;[여기에서, R8, R8' 및 R8"은 독립적으로 수소, C1내지 C4알킬, 페닐 또는 치환된 페닐(여기에서 치환체는 할로, 또는 C1내지 C4알콕시이다)이며, n은 0 또는 1의 정수이다.]
- 제1항에 있어서, R1, R2및 R3가 독립적으로 수소 또는 C1내지 C4알킬이고, R5가 하이드록실 또는 C1내지 C22아실기이며 A는 일반식(IV)의 그룹인 화합물을 제조하는 방법.상기 식에서, R8, R8' 및 R8"은 독립적으로 수소, C1내지 C4알킬, 페닐 또는 치환된 페닐(여기에서 치환체는 할로, 또는 C1내지 C4알콕시이다)이며; n은 0 또는 1의 정수이다.
- 제2항에 있어서, R1, R2및 R3가 수소인 화합물을 제조하는 방법.
- 제3항에 있어서, 4-아미노-5,6-헵타디에노산 또는 그의 약학적으로 허용되는 염을 제조하는 방법.
- 제3항에 있어서, 옥틸 4-아미노-5,6-헵타디에노에이트파라-톨루엔 설폰산을 제조하는 방법.
- 제3항에 있어서, 에틸 4-아미노-5,6-헵타디에노에이트파라-톨루엔 설폰산 또는 그의 염산염을 제조하는 방법.
- 제2항에 있어서, R1, R2및 R3가 독립적으로 수소 또는 메틸인 화합물을 제조하는 방법.
- 제7항에 있어서, 4-아미노-5-메틸-5,6-헵타디에노산 또는 그의 약학적으로 허용되는 염을 제조하는 방법.
- 제7항에 있어서, 4-아미노-7-메틸-5,6-헵타디에노산 또는 그의 약학적으로 허용되는 염을 제조하는 방법.
- 제7항에 있어서, 4-아미노-5,6-옥타디에노산 또는 그의 약학적으로 허용되는 염을 제조하는 방법.
- 제7항에 있어서, 옥틸 4-아미노-5-메틸-5,6-헵타디에노산 또는 그의 파라-톨루엔-설폰산염을 제조하는 방법.
- 제3항에 있어서, 4-N-3급-부틸옥시카보닐-5,6-헵타디에노산을 제조하는 방법.
- 제1항에 있어서, R1또는 R2가 독립적으로 수소 또는 할로이며, R3이 수소이고 R5가 하이드록실 또는 C1내지 C22아실기이고, A는 일반식(IV)의 그룹인 화합물을 제조하는 방법.상기 식에서, R8R8' 및 R8"은 독립적으로 수소, C1내지 C4알킬, 페닐 또는 치환된 페닐(여기에서 치환체는 할로, 또는 C1내지 C4알콕시이다)이며; n은 0 또는 1의 정수이다.
- 제13항에 있어서, 4-아미노-7-클로로-5,6-헵타디에노산 및 그의 약학적으로 허용되는 염을 제조하는 방법.
- 제13항에 있어서, 4-아미노-7-브로모-5,6-헵타디에노산 및 그의 약학적으로 허용되는 염을 제조하는 방법.
- 제1항에 있어서, R1또는 R2가 독립적으로 수소 또는 할로이며, R3이 C1내지 C4알킬이며, R5가 하이드록실 또는 C1내지 C22아실기이고, A는 일반식(IV)의 그룹인 화합물을 제조하는 방법.상기 식에서, R8, R8' 및 R8"은 독립적으로 수소, C1내지 C4알킬, 페닐 또는 치환된 페닐(여기에서 치환체는 할로, 또는 C1내지 C4알콕시이다)이며; n은 0 또는 1의 정수이다.
- 제16항에 있어서, 4-아미노-7-클로로-5-메틸-5,6-헵타디에노산 및 그의 약학적으로 허용되는 염을 제조하는 방법.
- 제1항에 있어서, R1, R2, R3및 R4가 모두 수소이고, R5가 하이드록실이며 A는 -CH=CH-인 화합물, 즉 4-아미노-2,5,6-헵타트리에노산 및 그의 약학적으로 허용되는 염을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51169183A | 1983-07-07 | 1983-07-07 | |
| US511691 | 1983-07-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR850001151A true KR850001151A (ko) | 1985-03-16 |
Family
ID=24036025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840003936A KR850001151A (ko) | 1983-07-07 | 1984-07-06 | r-알레닐-r-아미노부티르산의 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0134481B1 (ko) |
| JP (1) | JPS6036448A (ko) |
| KR (1) | KR850001151A (ko) |
| AT (1) | ATE31407T1 (ko) |
| AU (1) | AU566709B2 (ko) |
| CA (1) | CA1252477A (ko) |
| DE (1) | DE3468103D1 (ko) |
| DK (1) | DK335784A (ko) |
| ES (2) | ES8605468A1 (ko) |
| FI (1) | FI842723A (ko) |
| HU (1) | HU198902B (ko) |
| NO (1) | NO842759L (ko) |
| NZ (1) | NZ208805A (ko) |
| ZA (1) | ZA845237B (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5208345A (en) * | 1990-12-17 | 1993-05-04 | Merrell Dow Pharmaceuticals Inc. | Process for the production of (S)-vinyl and allenyl gaba |
| IL100360A (en) * | 1990-12-17 | 1998-08-16 | Merrell Dow Pharma | HISTORY OF PYROLIDINONE USED AS SUBSTANCE (S) -Vinyl and Alanyl GABA |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960927A (en) * | 1975-03-18 | 1976-06-01 | Richardson-Merrell Inc. | Olefinic derivatives of amino acids |
| US4178463A (en) * | 1978-01-30 | 1979-12-11 | Merrell Toraude Et Compagnie | Process for making 4-aminohex-5-enoic acid |
| GB2120244B (en) * | 1982-05-17 | 1985-05-01 | Merrell Toraude & Co | Aminoalkadiene derivative |
-
1984
- 1984-07-06 FI FI842723A patent/FI842723A/fi not_active Application Discontinuation
- 1984-07-06 HU HU842666A patent/HU198902B/hu not_active IP Right Cessation
- 1984-07-06 DK DK335784A patent/DK335784A/da not_active Application Discontinuation
- 1984-07-06 JP JP59141292A patent/JPS6036448A/ja active Pending
- 1984-07-06 EP EP84107917A patent/EP0134481B1/en not_active Expired
- 1984-07-06 ES ES534115A patent/ES8605468A1/es not_active Expired
- 1984-07-06 KR KR1019840003936A patent/KR850001151A/ko not_active Application Discontinuation
- 1984-07-06 NZ NZ208805A patent/NZ208805A/xx unknown
- 1984-07-06 CA CA000458364A patent/CA1252477A/en not_active Expired
- 1984-07-06 DE DE8484107917T patent/DE3468103D1/de not_active Expired
- 1984-07-06 NO NO842759A patent/NO842759L/no unknown
- 1984-07-06 AT AT84107917T patent/ATE31407T1/de not_active IP Right Cessation
- 1984-07-06 AU AU30375/84A patent/AU566709B2/en not_active Ceased
- 1984-07-06 ZA ZA845237A patent/ZA845237B/xx unknown
-
1985
- 1985-07-16 ES ES545264A patent/ES545264A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6036448A (ja) | 1985-02-25 |
| DK335784A (da) | 1985-01-08 |
| ES534115A0 (es) | 1986-04-01 |
| DK335784D0 (da) | 1984-07-06 |
| HUT34435A (en) | 1985-03-28 |
| AU566709B2 (en) | 1987-10-29 |
| FI842723A0 (fi) | 1984-07-06 |
| ATE31407T1 (de) | 1988-01-15 |
| CA1252477A (en) | 1989-04-11 |
| ES8603169A1 (es) | 1986-01-01 |
| ES8605468A1 (es) | 1986-04-01 |
| NO842759L (no) | 1985-01-08 |
| AU3037584A (en) | 1985-01-10 |
| DE3468103D1 (de) | 1988-01-28 |
| ZA845237B (en) | 1986-02-26 |
| EP0134481A1 (en) | 1985-03-20 |
| EP0134481B1 (en) | 1987-12-16 |
| HU198902B (en) | 1989-12-28 |
| ES545264A0 (es) | 1986-01-01 |
| FI842723A (fi) | 1985-01-08 |
| NZ208805A (en) | 1989-01-27 |
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