MA26869A1 - Synthese asymetrique de pregabaline - Google Patents

Synthese asymetrique de pregabaline

Info

Publication number
MA26869A1
MA26869A1 MA26738A MA26738A MA26869A1 MA 26869 A1 MA26869 A1 MA 26869A1 MA 26738 A MA26738 A MA 26738A MA 26738 A MA26738 A MA 26738A MA 26869 A1 MA26869 A1 MA 26869A1
Authority
MA
Morocco
Prior art keywords
pregabalin
pregabaline
asymmetric synthesis
synthesis
asymmetric
Prior art date
Application number
MA26738A
Other languages
English (en)
Inventor
Joseph Burk Mark
Simon Hoekstra Marvin
Arthur Mulhern Thomas
Andrew Ramsden James
Prakash Goel Om
Frederick Mich Thomas
Original Assignee
Warner Lambert Co
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.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26874236&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=MA26869(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Warner Lambert Co filed Critical Warner Lambert Co
Publication of MA26869A1 publication Critical patent/MA26869A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/23—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton
    • 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
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Psychiatry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catalysts (AREA)

Abstract

DEPOSANT Société dite : WARNER-LAMBERT COMPANY REVENDICATION DE PRIORITES US 25 Janvier 2000 60/178,261 ?Synthèse asymétrique de prégabaline" L'invention propose un procédé pour la préparation d'acide (S)-(+)-3-(aminomethyl)-5-méthylhexanoïque (prégabaline) ou d'un de ses sels par une synthèse par hydrogénation asymétrique. La prégabaline est utile pour le traitement et la prévention d'attaques cérébrales, de la douleur et de troubles psychotiques. La présente invention propose également des intermédiaires utiles dans la production de la prégabaline.
MA26738A 2000-01-27 2002-07-23 Synthese asymetrique de pregabaline MA26869A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17835900P 2000-01-27 2000-01-27
US19042700P 2000-03-17 2000-03-17

Publications (1)

Publication Number Publication Date
MA26869A1 true MA26869A1 (fr) 2004-12-20

Family

ID=26874236

Family Applications (1)

Application Number Title Priority Date Filing Date
MA26738A MA26869A1 (fr) 2000-01-27 2002-07-23 Synthese asymetrique de pregabaline

Country Status (50)

Country Link
US (1) US6891059B2 (fr)
EP (1) EP1250311B1 (fr)
JP (2) JP4235384B2 (fr)
KR (1) KR100549748B1 (fr)
CN (1) CN1210253C (fr)
AP (1) AP1438A (fr)
AR (1) AR028499A1 (fr)
AT (1) ATE261930T1 (fr)
AU (1) AU777046B2 (fr)
BG (1) BG65560B1 (fr)
BR (1) BRPI0107863B8 (fr)
CA (1) CA2396090C (fr)
CO (1) CO5251411A1 (fr)
CR (1) CR6703A (fr)
CU (1) CU23221A3 (fr)
CY (1) CY2004011I1 (fr)
CZ (1) CZ302838B6 (fr)
DE (1) DE60102356T2 (fr)
DK (1) DK1250311T3 (fr)
DZ (1) DZ3268A1 (fr)
EA (1) EA004934B1 (fr)
EE (1) EE05216B1 (fr)
EG (1) EG24138A (fr)
ES (1) ES2219493T3 (fr)
GE (1) GEP20043236B (fr)
HN (1) HN2001000010A (fr)
HR (1) HRP20020627B1 (fr)
HU (1) HU228815B1 (fr)
IL (2) IL150633A0 (fr)
IS (1) IS2038B (fr)
MA (1) MA26869A1 (fr)
ME (1) ME00921B (fr)
MX (1) MXPA02007307A (fr)
MY (1) MY127152A (fr)
NO (1) NO327958B1 (fr)
NZ (1) NZ519551A (fr)
OA (1) OA12167A (fr)
PA (1) PA8510501A1 (fr)
PE (1) PE20011063A1 (fr)
PL (1) PL203985B1 (fr)
PT (1) PT1250311E (fr)
RS (1) RS50257B (fr)
SI (1) SI1250311T1 (fr)
SK (1) SK287303B6 (fr)
SV (1) SV2002000295A (fr)
TN (1) TNSN01016A1 (fr)
TR (1) TR200400953T4 (fr)
TW (1) TWI288128B (fr)
UA (1) UA75584C2 (fr)
WO (1) WO2001055090A1 (fr)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL189872B1 (pl) 1996-07-24 2005-10-31 Warner Lambert Co Zastosowanie izobutylogaby i jej pochodnych do wytwarzania leku do leczenia bólu
BRPI0107863B8 (pt) * 2000-01-27 2017-04-25 Warner-Lambert Company método para preparar um derivado do ácido (s)-3- ciano-5-metilhexanoico, composto intermediário, seu método de preparação e método para preparar a pregabalina
US6687187B2 (en) * 2000-08-11 2004-02-03 Phonak Ag Method for directional location and locating system
EP1543831A1 (fr) * 2003-12-18 2005-06-22 Pfizer GmbH Arzneimittelwerk Gödecke Composition de pregabaline
ES2292107T3 (es) * 2004-03-12 2008-03-01 Warner-Lambert Company Llc Ligandos de bifosfina simetricos en c1 y su uso en la sintesis asimetrica de pregabalina.
UA82292C2 (uk) * 2004-04-14 2008-03-25 Пфайзер Продактс Инк. Спосіб стереоселективного біоперетворення аліфатичних динітрилів в ціанокарбонові кислоти (варіанти)
HRP20100054T1 (hr) * 2004-06-21 2010-05-31 Warner-Lambert Company Llc Dobivanje pregabalina i njemu sličnih spojeva
CN101160281A (zh) 2005-04-06 2008-04-09 特瓦制药工业有限公司 结晶形态的普瑞巴林
EP1768950A2 (fr) * 2005-04-11 2007-04-04 Teva Pharmaceutical Industries Ltd. Procede de fabrication de (s)-pregabaline
US7488846B2 (en) 2005-04-11 2009-02-10 Teva Pharmaceuical Industries Ltd. Pregabalin free of lactam and a process for preparation thereof
DE602006017995D1 (de) * 2005-05-10 2010-12-16 Teva Pharma Verfahren zur herstellung von pregabalin und salzen daraus
WO2006122255A1 (fr) 2005-05-10 2006-11-16 Teva Pharmaceutical Industries Ltd. Pregabaline exempte d'acide isobutylglutarique et son procede de preparation
US20070043241A1 (en) 2005-05-10 2007-02-22 Lilach Hedvati Optical resolution of 3-carbamoylmethyl-5-methylhexanoic acid
US20060270871A1 (en) * 2005-05-30 2006-11-30 Khanduri Chandra H Polymorphic form i of pregabalin and processes for its preparation
CN100410242C (zh) * 2005-06-23 2008-08-13 江苏恩华药业股份有限公司 普瑞巴林中间体及其制备方法
ES2398579T3 (es) 2005-09-19 2013-03-20 Teva Pharmaceutical Industries Ltd Una síntesis asimétrica de ácido (S)-(+)-3-(aminometil)-5-metilhexanoico
NL2000281C2 (nl) * 2005-11-02 2007-08-07 Pfizer Prod Inc Vaste farmaceutische samenstellingen die pregabaline bevatten.
EP1904486A2 (fr) * 2006-04-24 2008-04-02 Teva Pharmaceutical Industries Ltd Procede de synthese d'acide 3-isobutylglutarique
WO2007139933A2 (fr) 2006-05-24 2007-12-06 Teva Pharmaceutical Industries Ltd. Procédés pour la préparation d'acide r-(+)-3-(carbamoyl méthyl)-5-méthylhexanoïque et de sels de celui-ci
EP1912931A2 (fr) * 2006-05-31 2008-04-23 Teva Pharmaceutical Industries Ltd. Préparation de (s)-prégabaline nitrile
US20080026433A1 (en) * 2006-05-31 2008-01-31 Lilach Hedvati Use of enzymatic resolution for the preparation of intermediates of pregabalin
EP1903027A1 (fr) 2006-09-13 2008-03-26 Novartis AG Procédé de préparation de l' acide amino-4 butyrique ou de ses derivés et leur utilisation pour la préparation des inhibiteurs NEP
KR101036536B1 (ko) * 2007-03-22 2011-05-24 테바 파마슈티컬 인더스트리즈 리미티드 (ｓ)-(+)-3-(아미노메틸)-5-메틸 헥산산의 합성
WO2009001372A2 (fr) 2007-06-25 2008-12-31 Manne Satyanarayana Reddy Nouveau procédé pour la préparation de la prégabaline
KR100846419B1 (ko) * 2007-08-10 2008-07-15 한국과학기술원 프레가발린의 신규한 제조 방법
KR20090101462A (ko) * 2007-10-03 2009-09-28 테바 파마슈티컬 인더스트리즈 리미티드 프레가발린-4-엘리미네이트, 프레가발린 5-엘리미네이트, 기준 마커 및 표준물로서의 이들의 용도, 및 이들을 낮은 수준으로 함유하는 프레가발린의 제조 방법
EP2053040A1 (fr) * 2007-10-26 2009-04-29 Chemo Ibérica, S.A. Intermédiaires de la Prégabaline et leurs procédés de préparation et Prégabaline
EP2225199A2 (fr) * 2007-12-18 2010-09-08 Watson Pharma Private Limited Procédé perfectionné pour la préparation de (s)-prégabaline
CN101965328A (zh) * 2007-12-26 2011-02-02 基因里克斯(英国)有限公司 普瑞巴林的制备方法
KR20100110863A (ko) * 2008-01-10 2010-10-13 스미또모 가가꾸 가부시키가이샤 시클로프로판카르복실산 화합물의 제조 방법 및 그의 중간체
EP2110372A1 (fr) 2008-04-16 2009-10-21 Chemo Ibérica, S.A. Intermédiaires pour la préparation de prégabaline et leur procédé de préparation
SG157299A1 (en) 2008-05-09 2009-12-29 Agency Science Tech & Res Diagnosis and treatment of kawasaki disease
EP2294207B1 (fr) 2008-05-21 2012-09-26 Sandoz AG Procédé pour l'hydrolyse enzymatique stéréosélective d'un ester d'acide 5-méthyl-3-nitrométhyl-hexanoïque
EP2297090A1 (fr) * 2008-06-23 2011-03-23 Teva Pharmaceutical Industries Ltd. Synthèse enzymatique stéréosélective de l ester (s) ou (r)-isobutylglutarique
WO2010070593A2 (fr) 2008-12-19 2010-06-24 Pfizer Ireland Pharmaceuticals Esters de malonate
CN101987826A (zh) * 2009-08-04 2011-03-23 铜陵凯顺生物科技有限公司 一种(3s)-3-氨甲基-5-甲基己酸的合成方法
WO2011141923A2 (fr) 2010-05-14 2011-11-17 Lupin Limited Synthèse améliorée d'un ester alkylique optiquement pur de l'acide (s) - 3-cyano-5-méthyl-hexanoïque, intermédiaire de la (s)-prégabaline
US8212072B2 (en) 2010-08-13 2012-07-03 Divi's Laboratories, Ltd. Process for the preparation of pregabalin
WO2012025861A1 (fr) 2010-08-23 2012-03-01 Pfizer Manufacturing Ireland Procédé de préparation de dérivés d'acide (s)-3-cyano-5-méthylhexanoïque et de prégabaline
CN102464594B (zh) * 2010-11-17 2014-06-25 凯瑞斯德生化(苏州)有限公司 普瑞巴林的中间体化合物的制备方法
US9422230B2 (en) 2013-05-09 2016-08-23 Council Of Scientific And Industrial Research Process for the preparation of an anticonvulsant agent pregabalin hydrochloride
WO2016075082A1 (fr) 2014-11-10 2016-05-19 Sandoz Ag Amination réductrice stéréosélective d'aldéhydes alpha-chiraux au moyen d'ω-transaminases pour la synthèse de précurseurs de la prégabaline et du brivaracétam
WO2017019791A1 (fr) 2015-07-27 2017-02-02 Teva Pharmaceuticals International Gmbh Synthèse de (s)-prégabaline

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS588390B2 (ja) * 1978-05-23 1983-02-15 住友化学工業株式会社 光学活性ω↓−シアノ↓−α↓−アシルアミノ酸誘導体の製造法
US4939288A (en) * 1989-01-23 1990-07-03 Monsanto Company Method of preparing (R)-succinic acid derivatives
US6197819B1 (en) 1990-11-27 2001-03-06 Northwestern University Gamma amino butyric acid analogs and optical isomers
US5171892A (en) 1991-07-02 1992-12-15 E. I. Du Pont De Nemours And Company Chiral phospholanes via chiral 1,4-diol cyclic sulfates
US5616793A (en) 1995-06-02 1997-04-01 Warner-Lambert Company Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid
US5637767A (en) * 1995-06-07 1997-06-10 Warner-Lambert Company Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid
US5840965A (en) * 1996-06-24 1998-11-24 E. I. Du Pont De Nemours And Company Process for the production of purified telephthalic acid
PL189872B1 (pl) 1996-07-24 2005-10-31 Warner Lambert Co Zastosowanie izobutylogaby i jej pochodnych do wytwarzania leku do leczenia bólu
US6127418A (en) 1997-08-20 2000-10-03 Warner-Lambert Company GABA analogs to prevent and treat gastrointestinal damage
JP2002508345A (ja) 1997-12-17 2002-03-19 カイロテック・テクノロジー・リミテッド 不斉水素化
WO1999052852A1 (fr) 1998-04-09 1999-10-21 Chirotech Technology Limited Hydrogenation asymetrique
BRPI0107863B8 (pt) * 2000-01-27 2017-04-25 Warner-Lambert Company método para preparar um derivado do ácido (s)-3- ciano-5-metilhexanoico, composto intermediário, seu método de preparação e método para preparar a pregabalina

Also Published As

Publication number Publication date
IS6430A (is) 2002-06-19
SK10782002A3 (sk) 2002-11-06
SK287303B6 (sk) 2010-06-07
HRP20020627A2 (en) 2004-08-31
ES2219493T3 (es) 2004-12-01
EE200200403A (et) 2003-10-15
AU2213801A (en) 2001-08-07
BG65560B1 (bg) 2008-12-30
CZ20022520A3 (cs) 2002-10-16
BR0107863B1 (pt) 2013-06-18
IL150633A0 (en) 2003-02-12
ME00921B (me) 2012-06-20
JP4886753B2 (ja) 2012-02-29
OA12167A (en) 2006-05-08
UA75584C2 (uk) 2006-05-15
DZ3268A1 (fr) 2001-08-02
CR6703A (es) 2003-06-24
IL150633A (en) 2009-08-03
HRP20020627B1 (hr) 2011-01-31
CZ302838B6 (cs) 2011-12-07
IS2038B (is) 2005-08-15
EA004934B1 (ru) 2004-10-28
NO327958B1 (no) 2009-10-26
HUP0204307A2 (hu) 2003-06-28
EA200200642A1 (ru) 2002-12-26
AR028499A1 (es) 2003-05-14
JP2009073841A (ja) 2009-04-09
ATE261930T1 (de) 2004-04-15
BR0107863A (pt) 2002-11-05
RS50257B (sr) 2009-07-15
CO5251411A1 (es) 2003-02-28
JP4235384B2 (ja) 2009-03-11
YU56202A (sh) 2006-01-16
SV2002000295A (es) 2002-06-07
TNSN01016A1 (fr) 2005-11-10
MY127152A (en) 2006-11-30
CY2004011I1 (el) 2010-07-28
NZ519551A (en) 2004-02-27
DE60102356T2 (de) 2005-02-17
AP2002002588A0 (en) 2002-09-30
TR200400953T4 (tr) 2004-07-21
DK1250311T3 (da) 2004-08-16
WO2001055090A1 (fr) 2001-08-02
EP1250311B1 (fr) 2004-03-17
MXPA02007307A (es) 2002-11-29
NO20023582L (no) 2002-09-02
PT1250311E (pt) 2004-07-30
PL203985B1 (pl) 2009-11-30
US6891059B2 (en) 2005-05-10
CU23221A3 (es) 2007-07-20
PL357077A1 (en) 2004-07-12
CA2396090C (fr) 2006-01-10
DE60102356D1 (de) 2004-04-22
HN2001000010A (es) 2001-06-13
AU777046B2 (en) 2004-09-30
HU228815B1 (en) 2013-05-28
PA8510501A1 (es) 2002-02-21
CN1396905A (zh) 2003-02-12
EE05216B1 (et) 2009-10-15
KR20020073187A (ko) 2002-09-19
BRPI0107863B8 (pt) 2017-04-25
US20030212290A1 (en) 2003-11-13
EP1250311A1 (fr) 2002-10-23
EG24138A (en) 2008-08-06
TWI288128B (en) 2007-10-11
JP2003520841A (ja) 2003-07-08
BG106849A (en) 2003-03-31
SI1250311T1 (en) 2004-10-31
PE20011063A1 (es) 2001-10-18
CN1210253C (zh) 2005-07-13
KR100549748B1 (ko) 2006-02-08
NO20023582D0 (no) 2002-07-26
AP1438A (en) 2005-05-23
HUP0204307A3 (en) 2003-07-28
CA2396090A1 (fr) 2001-08-02
GEP20043236B (en) 2004-05-25

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