CA2186263A1 - Separation of the Enantiomers of Amlodipine Via Their Diastereomeric Tartrates - Google Patents
Separation of the Enantiomers of Amlodipine Via Their Diastereomeric TartratesInfo
- Publication number
- CA2186263A1 CA2186263A1 CA2186263A CA2186263A CA2186263A1 CA 2186263 A1 CA2186263 A1 CA 2186263A1 CA 2186263 A CA2186263 A CA 2186263A CA 2186263 A CA2186263 A CA 2186263A CA 2186263 A1 CA2186263 A1 CA 2186263A1
- Authority
- CA
- Canada
- Prior art keywords
- amlodipine
- separation
- enantiomers
- tartrates
- diastereomeric
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Abstract
A method for the separation of R-(+)- and S-(-)-isomers of amlodipine (I) from mixtures thereof, which comprises the reaction of the mixture of isomers with either L- or D-tartaric acid in an organic solvent containing sufficient dimethyl sulphoxide (DMSO) for the precipitation of, respectively, a DMSO solvate of an L-tartrate salt of R-(+)-amlodipine, or a DMSO solvate of a D-tartrate salt of S-(-)-amlodipine.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9405833.6 | 1994-03-24 | ||
GB9405833A GB9405833D0 (en) | 1994-03-24 | 1994-03-24 | Separation of the enantiomers of amlodipine |
PCT/EP1995/000847 WO1995025722A1 (en) | 1994-03-24 | 1995-03-06 | Separation of the enantiomers of amlodipine via their diastereomeric tartrates |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2186263A1 true CA2186263A1 (en) | 1995-09-28 |
CA2186263C CA2186263C (en) | 1999-05-11 |
Family
ID=10752425
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002186263A Expired - Fee Related CA2186263C (en) | 1994-03-24 | 1995-03-06 | Separation of the enantiomers of amlodipine via their diastereomeric tartrates |
Country Status (27)
Country | Link |
---|---|
US (2) | US5750707A (en) |
EP (1) | EP0751938B1 (en) |
JP (1) | JP2843681B2 (en) |
KR (1) | KR100188980B1 (en) |
CN (1) | CN1067055C (en) |
AT (1) | ATE166050T1 (en) |
AU (1) | AU677765B2 (en) |
BR (1) | BR9507137A (en) |
CA (1) | CA2186263C (en) |
CO (1) | CO4230248A1 (en) |
CZ (1) | CZ287324B6 (en) |
DE (1) | DE69502486T2 (en) |
DK (1) | DK0751938T3 (en) |
ES (1) | ES2116737T3 (en) |
FI (1) | FI113646B (en) |
GB (1) | GB9405833D0 (en) |
HU (1) | HU214720B (en) |
IL (1) | IL113008A (en) |
MY (1) | MY111979A (en) |
NO (1) | NO306110B1 (en) |
NZ (1) | NZ282404A (en) |
PE (1) | PE48895A1 (en) |
PL (1) | PL180085B1 (en) |
RU (1) | RU2132845C1 (en) |
TW (1) | TW448156B (en) |
WO (1) | WO1995025722A1 (en) |
ZA (1) | ZA952362B (en) |
Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9317773D0 (en) * | 1993-08-26 | 1993-10-13 | Pfizer Ltd | Therapeutic compound |
US7303768B2 (en) * | 1998-07-24 | 2007-12-04 | Seo Hong Yoo | Preparation of aqueous clear solution dosage forms with bile acids |
US20070072828A1 (en) * | 1998-07-24 | 2007-03-29 | Yoo Seo H | Bile preparations for colorectal disorders |
US7772220B2 (en) * | 2004-10-15 | 2010-08-10 | Seo Hong Yoo | Methods and compositions for reducing toxicity of a pharmaceutical compound |
US20050158408A1 (en) * | 1998-07-24 | 2005-07-21 | Yoo Seo H. | Dried forms of aqueous solubilized bile acid dosage formulation: preparation and uses thereof |
US6333342B1 (en) | 1998-11-04 | 2001-12-25 | Isotechnika, Inc | Methods of pharmacological treatment using S(−) amlodipine |
CN1100038C (en) | 2000-02-21 | 2003-01-29 | 张喜田 | Separation of Amlodipine antimer |
GB0020842D0 (en) * | 2000-08-23 | 2000-10-11 | Pfizer Ltd | Therapeutic compositions |
US6737430B2 (en) | 2000-11-09 | 2004-05-18 | Pfizer, Inc. | Mutual prodrug of amlodipine and atorvastatin |
IL161448A0 (en) | 2001-10-24 | 2004-09-27 | Sepracor Inc | Method of resolving amlodipine racemate |
CN1152013C (en) * | 2001-11-22 | 2004-06-02 | 张喜田 | Levo-amlodipine salt able to generate hydrate and its hydrate and preparation |
US20030176706A1 (en) * | 2002-03-18 | 2003-09-18 | Joshi Rohini Ramesh | Process for the preparation of [S(-) amlodipine - L (+)- hemitartarate] |
EP1348697A1 (en) * | 2002-03-28 | 2003-10-01 | Council Of Scientific & Industrial Research | Process for the preparation of S(-)-amlodipine-L(+)-hemitartrate |
KR100476636B1 (en) * | 2002-09-11 | 2005-03-17 | 한림제약(주) | Process for the preparation of S-(-)-amlodipine by use of L-(+)-tartrate |
US20040072879A1 (en) * | 2002-10-10 | 2004-04-15 | Dr. Reddy's Laboratories Limited | Crystalline 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine maleate salt (Amlodipine) |
BRPI0406987A (en) * | 2003-01-31 | 2006-01-10 | Sankyo Co | Medicament for the prevention and / or treatment of atherosclerosis, medicaments for inhibiting vascular smooth muscle cell proliferation, neointimal formation of blood vessels and vascular remodeling, medicament for the prevention of restenosis following percutaneous coronary intervention, and, medicines for the prophylaxis and / or treatment of hypertension or diseases caused by hypertension or diseases caused by hypertension, heart disease, angina pectoris, myocardial infarction, arrhythmia, sudden death, heart failure, cardiac hypertrophy, kidney diseases, diabetic nephropathy, glomerulonephritis, nephrosclerosis, cerebrovascular diseases, cerebral infarction, and cerebral hemorrhage |
US7145125B2 (en) | 2003-06-23 | 2006-12-05 | Advanced Optical Technologies, Llc | Integrating chamber cone light using LED sources |
US6846932B1 (en) * | 2003-11-20 | 2005-01-25 | Council Of Scientific And Industrial Research | Process for preparation of chiral amlodipine salts |
EP1687273A1 (en) * | 2003-11-20 | 2006-08-09 | Council Of Scientific And Industrial Research | Process for preparation of chiral amlodipine salts |
CN1231469C (en) * | 2003-12-05 | 2005-12-14 | 石家庄制药集团欧意药业有限公司 | Optically active amlodipine resolving process |
US20060035940A1 (en) * | 2004-03-16 | 2006-02-16 | Sepracor Inc. | (S)-Amlodipine malate |
KR101414810B1 (en) * | 2004-08-30 | 2014-07-18 | 주식회사 유스팜인터내셔널 | Neuroprotective effect of solubilized udca in focal ischemic model |
EP1809330B1 (en) * | 2004-10-15 | 2011-04-27 | Seo Hong Yoo | Compositions for reducing toxicity of cisplatin, carboplatin, and oxaliplatin |
ES2307209T3 (en) * | 2004-10-20 | 2008-11-16 | Emcure Pharmaceuticals Limited | PROCEDURE FOR THE PRODUCTION OF AN AMLODIPINE CHARMER WITH A HIGH OPTIC PURITY. |
KR101358078B1 (en) * | 2004-11-01 | 2014-02-06 | 주식회사 유스팜인터내셔널 | Methods and compositions for reducing neurodegeneration in amyotrophic lateral sclerosis |
KR101152608B1 (en) | 2004-12-02 | 2012-06-07 | 에스케이케미칼주식회사 | Optical resolution method of (R)- or (S)-amlodipine isomer from (R,S)-amlodipine mixture |
US7772400B2 (en) | 2004-12-02 | 2010-08-10 | Sk Chemicals Co., Ltd. | Optical resolution method of amlodipine |
HUP0500570A3 (en) * | 2005-06-08 | 2008-03-28 | Richter Gedeon Nyrt | Process for the preparation of (s)-(-)-amlodipine |
WO2007001066A1 (en) * | 2005-06-27 | 2007-01-04 | Daiichi Sankyo Company, Limited | Pharmaceutical preparation containing an angiotensin ii receptor antagonist and a calcium channel blocker |
KR101235116B1 (en) * | 2005-10-17 | 2013-02-20 | 에스케이케미칼주식회사 | Process for preparation of chiral amlodipine gentisate |
CN100436417C (en) * | 2006-04-11 | 2008-11-26 | 石药集团中奇制药技术(石家庄)有限公司 | Resolution method of optically active amlodipine |
KR100913791B1 (en) * | 2006-07-21 | 2009-08-26 | 한미약품 주식회사 | S---amlodipine camsylate or hydrate thereof and pharmaceutical composition containing same |
TWI399223B (en) * | 2006-09-15 | 2013-06-21 | Daiichi Sankyo Co Ltd | Solid dosage form of olmesartan medoxomil and amlodipine |
KR100828883B1 (en) * | 2006-10-27 | 2008-05-09 | 씨제이제일제당 (주) | Method for the separation of S---amlodipine from racemic amlodipine |
KR100830003B1 (en) * | 2006-10-31 | 2008-05-15 | 씨제이제일제당 (주) | Crystalline S---amlodipine adipic acid salt anhydrous and preparation method thereof |
KR100868160B1 (en) | 2007-02-14 | 2008-11-12 | 한미약품 주식회사 | Method of preparing s---amlodipine or salt thereof and intermediate used therein |
KR100979772B1 (en) | 2008-06-12 | 2010-09-02 | 에이치 엘 지노믹스(주) | Process for preparing optically pure S---amlodipine benzensulfonate |
KR100989970B1 (en) | 2008-07-01 | 2010-10-26 | 미래파인켐 주식회사 | Resolution method of S---amlodipine |
KR101085169B1 (en) | 2009-03-25 | 2011-11-18 | (주)켐트로스 | Process for separating the enantiomers of amlodipine |
KR101705535B1 (en) * | 2009-04-01 | 2017-02-28 | 주식회사 씨트리 | Method for Preparing an Optically Active 1-(3-hydroxyphenyl)ethylamine |
RU2537361C1 (en) * | 2013-07-18 | 2015-01-10 | Общество С Ограниченной Ответственностью "Синтегал" | Optic isomers of (+) and (-)-benzhydrylureas and (+) and (-)-1-[(3-chlorophenyl)-phenyl-methyl]urea, pharmaceutical composition based on thereof and method of thereof obtaining |
CN113041244B (en) | 2019-11-08 | 2022-06-21 | 施慧达药业集团(吉林)有限公司 | Composition containing levamlodipine besylate hydrate and preparation method thereof |
CN111100064B (en) * | 2020-01-08 | 2024-01-02 | 湖南理工学院 | Method for enriching, recovering and resolving alkaline chiral medicine amlodipine from waste liquid |
CN111777547B (en) * | 2020-07-17 | 2021-10-08 | 江西施美药业股份有限公司 | Method for inducing crystallization and resolution of levamlodipine |
US11452690B1 (en) | 2021-01-27 | 2022-09-27 | ECI Pharmaceuticals, LLC | Oral liquid compositions comprising amlodipine besylate and methods of using the same |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5364872A (en) * | 1984-04-16 | 1994-11-15 | Yamanouchi Pharmaceutical Co., Ltd. | Dihydropyridine-3,5-dicarboxylic acid ester derivatives |
GR850872B (en) * | 1984-04-16 | 1985-11-25 | Yamanouchi Pharma Co Ltd | |
US5326772A (en) * | 1984-09-28 | 1994-07-05 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Diaryl compounds for their use |
FR2586417B1 (en) * | 1985-08-21 | 1991-08-30 | Glaxo Spa | HETEROCYCLIC COMPOUNDS, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITION |
DK142287A (en) * | 1986-03-27 | 1987-09-28 | Byk Gulden Lomberg Chem Fab | OPTIC ACTIVE 1,4-DIHYDROPYRIDINE DERIVATIVES |
NZ220022A (en) * | 1986-04-22 | 1990-04-26 | Byk Gulden Lomberg Chem Fab | 1,4-dihydropyridine derivatives and pharmaceutical compositions |
JPH03500647A (en) * | 1987-10-27 | 1991-02-14 | ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | New pyrrolidine |
GB8804630D0 (en) * | 1988-02-27 | 1988-03-30 | Pfizer Ltd | Preparation of r-& s-amlodipine |
GB8822170D0 (en) * | 1988-09-21 | 1988-10-26 | Pfizer Ltd | Therapeutic agents |
IT1230752B (en) * | 1989-02-17 | 1991-10-29 | Boehringer Biochemia Srl | PROCESS FOR THE PREPARATION OF 1,4 POLY-SUBSTITUTED DIHYDROPYRIDINS IN AN ANTIOMERICALLY PURE FORM. |
DE3906460C1 (en) * | 1989-03-01 | 1990-11-15 | Goedecke Ag, 1000 Berlin, De |
-
1994
- 1994-03-24 GB GB9405833A patent/GB9405833D0/en active Pending
-
1995
- 1995-02-08 TW TW084101060A patent/TW448156B/en not_active IP Right Cessation
- 1995-03-06 HU HU9602597A patent/HU214720B/en not_active IP Right Cessation
- 1995-03-06 CZ CZ19962784A patent/CZ287324B6/en not_active IP Right Cessation
- 1995-03-06 CN CN95192238A patent/CN1067055C/en not_active Expired - Fee Related
- 1995-03-06 CA CA002186263A patent/CA2186263C/en not_active Expired - Fee Related
- 1995-03-06 KR KR1019960705266A patent/KR100188980B1/en not_active IP Right Cessation
- 1995-03-06 ES ES95912222T patent/ES2116737T3/en not_active Expired - Lifetime
- 1995-03-06 WO PCT/EP1995/000847 patent/WO1995025722A1/en active IP Right Grant
- 1995-03-06 AU AU19493/95A patent/AU677765B2/en not_active Ceased
- 1995-03-06 JP JP7524336A patent/JP2843681B2/en not_active Expired - Fee Related
- 1995-03-06 BR BR9507137A patent/BR9507137A/en not_active IP Right Cessation
- 1995-03-06 NZ NZ282404A patent/NZ282404A/en unknown
- 1995-03-06 AT AT95912222T patent/ATE166050T1/en not_active IP Right Cessation
- 1995-03-06 PL PL95316535A patent/PL180085B1/en not_active IP Right Cessation
- 1995-03-06 DK DK95912222T patent/DK0751938T3/en active
- 1995-03-06 RU RU96119351A patent/RU2132845C1/en not_active IP Right Cessation
- 1995-03-06 US US08/704,612 patent/US5750707A/en not_active Expired - Fee Related
- 1995-03-06 DE DE69502486T patent/DE69502486T2/en not_active Expired - Fee Related
- 1995-03-06 EP EP95912222A patent/EP0751938B1/en not_active Expired - Lifetime
- 1995-03-13 CO CO95009744A patent/CO4230248A1/en unknown
- 1995-03-16 PE PE1995264250A patent/PE48895A1/en not_active Application Discontinuation
- 1995-03-16 IL IL11300895A patent/IL113008A/en not_active IP Right Cessation
- 1995-03-20 MY MYPI95000696A patent/MY111979A/en unknown
- 1995-03-23 ZA ZA952362A patent/ZA952362B/en unknown
-
1996
- 1996-09-23 NO NO963991A patent/NO306110B1/en unknown
- 1996-09-23 FI FI963775A patent/FI113646B/en active
-
1998
- 1998-05-05 US US09/071,810 patent/US6046338A/en not_active Expired - Fee Related
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |