IL96227A - Process for making vinyl-gaba - Google Patents

Process for making vinyl-gaba

Info

Publication number: IL96227A
Authority: IL; Israel
Prior art keywords: water; hydrolysis; acid; vinyl; process according
Prior art date: 1989-11-07

Application number

IL9622790A

Other languages

English (en)

Hebrew (he)

Other versions

IL96227A0 (en

Original Assignee

Merrell Dow Pharma

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.)

1989-11-07

Filing date

1990-11-02

Publication date

1994-10-21

1990-11-02 Application filed by Merrell Dow Pharma filed Critical Merrell Dow Pharma

1991-08-16 Publication of IL96227A0 publication Critical patent/IL96227A0/xx

1994-10-21 Publication of IL96227A publication Critical patent/IL96227A/en

Links

238000000034 method Methods 0.000 title claims description 14
238000004519 manufacturing process Methods 0.000 title abstract description 6
230000007062 hydrolysis Effects 0.000 claims abstract description 14
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 14
OYVDXEVJHXWJAE-UHFFFAOYSA-N 5-ethenylpyrrolidin-2-one Chemical compound C=CC1CCC(=O)N1 OYVDXEVJHXWJAE-UHFFFAOYSA-N 0.000 claims abstract 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
239000012046 mixed solvent Substances 0.000 claims description 4
PJDFLNIOAUIZSL-UHFFFAOYSA-N vigabatrin Chemical compound C=CC(N)CCC(O)=O PJDFLNIOAUIZSL-UHFFFAOYSA-N 0.000 claims 2
229920002554 vinyl polymer Polymers 0.000 abstract description 20
229960003692 gamma aminobutyric acid Drugs 0.000 abstract description 16
-1 vinyl GABA Chemical compound 0.000 abstract description 16
239000007787 solid Substances 0.000 description 15
239000002002 slurry Substances 0.000 description 14
239000002253 acid Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
238000010992 reflux Methods 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
238000005903 acid hydrolysis reaction Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000008367 deionised water Substances 0.000 description 4
229910021641 deionized water Inorganic materials 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000011591 potassium Substances 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1

Classifications

- 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
- 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
- C07C227/22—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyrrole Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL9622790A 1989-11-07 1990-11-02 Process for making vinyl-gaba IL96227A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US43270789A	1989-11-07	1989-11-07

Publications (2)

Publication Number	Publication Date
IL96227A0 IL96227A0 (en)	1991-08-16
IL96227A true IL96227A (en)	1994-10-21

Family

ID=23717279

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9622790A IL96227A (en)	1989-11-07	1990-11-02	Process for making vinyl-gaba

Country Status (14)

Country	Link
US (1)	US6090979A (de)
EP (1)	EP0427197B1 (de)
JP (1)	JP3116328B2 (de)
KR (1)	KR0163042B1 (de)
AT (1)	ATE104951T1 (de)
AU (1)	AU629419B2 (de)
CA (1)	CA2028782C (de)
DE (1)	DE69008487T2 (de)
DK (1)	DK0427197T3 (de)
ES (1)	ES2055848T3 (de)
HU (1)	HUT55345A (de)
IE (1)	IE64393B1 (de)
IL (1)	IL96227A (de)
ZA (1)	ZA908751B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0546230A1 (de) *	1991-12-10	1993-06-16	Merrell Dow Pharmaceuticals Inc.	Neue Verfahren zur Herstellung von 4-Amino-5-Hexensäure
EP2537827B1 (de)	2011-06-24	2014-06-11	Targeon SAS	Verfahren zur Herstellung von 4-Amino-5-Hexensäure aus Succinimid
CN110072521B (zh)	2016-12-16	2022-11-29	爱杜西亚药品有限公司	包含t型钙通道阻断剂的药物组合
CN116120200B (zh) *	2021-11-15	2025-08-29	武汉武药科技有限公司	氨己烯酸原料药、氨己烯酸固体组合物及其制备方法
CN116621720B (zh) *	2023-07-21	2023-10-27	成都硕德药业有限公司	一种氨己烯酸的制备方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2221441B1 (de) *	1973-03-13	1976-05-21	Choay Sa
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
US4254284A (en) *	1978-01-30	1981-03-03	Merrell Toraude Et Compagnie	Process for preparing 4-aminohex-5-ynoic acid
US4235778A (en)	1978-01-30	1980-11-25	Merrell Toraude Et Compagnie	2-Pyrrolidone compounds and processes for making same
JPS5639050A (en) *	1979-09-06	1981-04-14	Toray Ind Inc	Preparation of omega-aminoalkanecarboxylic acid
US4371706A (en) *	1980-05-06	1983-02-01	Phillips Petroleum Company	Preparation of alkali metal aminoalkanoates
DK373383A (da) *	1982-08-20	1984-02-21	Midit	Fremgangsmaade til fremstilling af omega-aminosyrederivater
GB2133002B (en) *	1982-12-30	1986-01-29	Merrell Toraude & Co	Process for preparing 4-amino-5-hexenoic acid
US4529818A (en) *	1983-06-07	1985-07-16	Phillips Petroleum Company	Continuous process for the production of alkali metal n-methylaminobutyrate

1990
- 1990-10-29 AU AU65597/90A patent/AU629419B2/en not_active Expired
- 1990-10-29 CA CA002028782A patent/CA2028782C/en not_active Expired - Lifetime
- 1990-10-31 ZA ZA908751A patent/ZA908751B/xx unknown
- 1990-10-31 JP JP02292198A patent/JP3116328B2/ja not_active Expired - Lifetime
- 1990-11-02 IL IL9622790A patent/IL96227A/en not_active IP Right Cessation
- 1990-11-05 KR KR1019900017806A patent/KR0163042B1/ko not_active Expired - Lifetime
- 1990-11-06 DE DE69008487T patent/DE69008487T2/de not_active Expired - Lifetime
- 1990-11-06 AT AT9090121208T patent/ATE104951T1/de not_active IP Right Cessation
- 1990-11-06 ES ES90121208T patent/ES2055848T3/es not_active Expired - Lifetime
- 1990-11-06 EP EP90121208A patent/EP0427197B1/de not_active Expired - Lifetime
- 1990-11-06 HU HU907046A patent/HUT55345A/hu unknown
- 1990-11-06 IE IE400490A patent/IE64393B1/en not_active IP Right Cessation
- 1990-11-06 DK DK90121208.4T patent/DK0427197T3/da active
1997
- 1997-08-18 US US08/912,770 patent/US6090979A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP3116328B2 (ja)	2000-12-11
JPH03153652A (ja)	1991-07-01
KR0163042B1 (ko)	1999-01-15
DE69008487D1 (de)	1994-06-01
AU629419B2 (en)	1992-10-01
HUT55345A (en)	1991-05-28
ES2055848T3 (es)	1994-09-01
IE904004A1 (en)	1991-05-08
US6090979A (en)	2000-07-18
DK0427197T3 (da)	1994-05-30
EP0427197A1 (de)	1991-05-15
CA2028782C (en)	2003-10-14
DE69008487T2 (de)	1994-09-08
ZA908751B (en)	1991-08-28
CA2028782A1 (en)	1991-05-08
EP0427197B1 (de)	1994-04-27
AU6559790A (en)	1991-05-16
IE64393B1 (en)	1995-08-09
IL96227A0 (en)	1991-08-16
ATE104951T1 (de)	1994-05-15
KR910009637A (ko)	1991-06-28

Legal Events

Date	Code	Title	Description
1997-01-10	KB	Patent renewed
2001-04-30	HC	Change of name of proprietor(s)
2001-04-30	HP	Change in proprietorship
2001-04-30	KB	Patent renewed
2005-02-20	KB	Patent renewed
2006-09-05	HC	Change of name of proprietor(s)	Owner name: AVENTIS INC. Free format text: FORMER NAME:MERRELL PHARMACEUTICALS INCORPORATED
2009-05-03	FF	Patent granted
2011-06-30	EXP	Patent expired

Publication	Publication Date	Title
RU2158266C2 (ru)	2000-10-27	Способ получения пуриновых соединений, используемое в нем промежуточное соединение и способ его получения
IL96227A (en)	1994-10-21	Process for making vinyl-gaba
EP0678501B1 (de)	1997-07-30	Verfahren zur Herstellung von N-Chloracetylglutamin
US4760164A (en)	1988-07-26	Process for producing α-L-aspartyl-L-phenylalanine methyl ester
US4284797A (en)	1981-08-18	Process for separating mixtures of 3- and 4-nitrophthalic acid
WO1991012256A1 (en)	1991-08-22	Process for preparing l-alpha-glycerylphosphoryl-d-myoinositol and its salts
US4841092A (en)	1989-06-20	Preparation of tris(2-cyanoethyl)amine
US2561323A (en)	1951-07-17	Method of preparing glutamic acid mono esters
JP4271348B2 (ja)	2009-06-03	１，３−アダマンタンジカルボン酸ジ−ｔｅｒｔ−ブチルの製造方法
US3419616A (en)	1968-12-31	Preparation of ninhydrin
US2461847A (en)	1949-02-15	Process for the preparation of dl-threonine
US4301288A (en)	1981-11-17	Process for 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid
JP4120015B2 (ja)	2008-07-16	新規な脂環式テトラカルボン酸二無水物、その中間体及びそれらの製造法
EP0306936A2 (de)	1989-03-15	Verfahren zur Herstellung von Aminooxyessigsäure-Salzen
US4550193A (en)	1985-10-29	Process for the preparation of 2,3-dimercaptosuccinic acid and its lower alkyl esters
KR810001695B1 (ko)	1981-10-27	테레프탈산아미드 유도체의 제법
CA1066291A (en)	1979-11-13	3-formyl-4-methyl-2,6-dihydroxypyridine and a process for its preparation
KR820001386B1 (ko)	1982-08-04	치환 이미다졸의 제조방법
CA2014533A1 (en)	1990-10-24	Process for the production of 4 - hydroxy -6- polyfluoroalkylpyrimidines
JPH0236178A (ja)	1990-02-06	４−ヒドロキシクマリンの製造法
CN1120037A (zh)	1996-04-10	制备吲哚衍生物的方法
HK1012348B (en)	2002-04-12	Preparation of purines
JPS6348282A (ja)	1988-02-29	ベンゾピラノピリジン誘導体
EP0161499A1 (de)	1985-11-21	Verfahren zur Herstellung von Aminophthalidisochinolinen
KR930023330A (ko)	1993-12-18	3-아미노-4-메톡시아세트아닐리드의 제조방법