RU96119351A - SEPARATION OF AMLODIPINE ENANTIOMERS THROUGH THEIR DIASTEROMERIC TARTRATES - Google Patents
SEPARATION OF AMLODIPINE ENANTIOMERS THROUGH THEIR DIASTEROMERIC TARTRATESInfo
- Publication number
- RU96119351A RU96119351A RU96119351/04A RU96119351A RU96119351A RU 96119351 A RU96119351 A RU 96119351A RU 96119351/04 A RU96119351/04 A RU 96119351/04A RU 96119351 A RU96119351 A RU 96119351A RU 96119351 A RU96119351 A RU 96119351A
- Authority
- RU
- Russia
- Prior art keywords
- amlodipine
- dmso
- solvent
- hemi
- tartrate
- Prior art date
Links
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical class CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 title claims 3
- 238000000926 separation method Methods 0.000 title claims 2
- 150000003892 tartrate salts Chemical class 0.000 title 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 20
- 238000000034 method Methods 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 8
- 239000006184 cosolvent Substances 0.000 claims 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 229960001270 d- tartaric acid Drugs 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 229960000528 amlodipine Drugs 0.000 claims 2
- 150000004682 monohydrates Chemical class 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Claims (13)
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 |
|---|---|
| RU96119351A true RU96119351A (en) | 1998-12-27 |
| RU2132845C1 RU2132845C1 (en) | 1999-07-10 |
Family
ID=10752425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU96119351A RU2132845C1 (en) | 1994-03-24 | 1995-03-06 | Method of isolating r-(+)- and s-(-)-amplodipin isomers from mixtures thereof, (r)-(+) and s-(-)-amplodipin-hemi- l- or d-tartrate solvates and monohydrates |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2393150C2 (en) * | 2005-10-17 | 2010-06-27 | Ск Кемикалз Ко., Лтд. | Method of preparing chiral amlodipine gentisate |
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|---|---|---|---|---|
| GB9317773D0 (en) * | 1993-08-26 | 1993-10-13 | Pfizer Ltd | Therapeutic 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 |
| US7772220B2 (en) * | 2004-10-15 | 2010-08-10 | Seo Hong Yoo | Methods and compositions for reducing toxicity of a pharmaceutical compound |
| US20070072828A1 (en) * | 1998-07-24 | 2007-03-29 | Yoo Seo H | Bile preparations for colorectal disorders |
| US7303768B2 (en) * | 1998-07-24 | 2007-12-04 | Seo Hong Yoo | Preparation of aqueous clear solution dosage forms with bile acids |
| 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 |
| CA2466806A1 (en) * | 2001-10-24 | 2003-05-01 | 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) |
| EP3045174A1 (en) * | 2003-01-31 | 2016-07-20 | Daiichi Sankyo Company, Limited | Medicine for prevention of and treatment for arteriosclerosis and hypertension |
| US7145125B2 (en) | 2003-06-23 | 2006-12-05 | Advanced Optical Technologies, Llc | Integrating chamber cone light using LED sources |
| EP1687273A1 (en) * | 2003-11-20 | 2006-08-09 | Council Of Scientific And Industrial Research | Process for preparation of chiral amlodipine salts |
| US6846932B1 (en) * | 2003-11-20 | 2005-01-25 | 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 |
| WO2005089353A2 (en) * | 2004-03-16 | 2005-09-29 | Sepracor Inc. | (s)-amlodipine malate |
| CN101035541B (en) * | 2004-08-30 | 2012-05-30 | 柳署弘 | Neuroprotective effect of solubilized UDCA in focal ischemic model |
| AU2005295541B2 (en) * | 2004-10-15 | 2011-02-17 | Seo Hong Yoo | Methods and compositions for reducing toxicity of a pharmaceutical compound |
| JP4932728B2 (en) * | 2004-10-20 | 2012-05-16 | エムキュア ファーマシューティカルズ リミテッド | Process for producing enantiomers of amlodipine with high optical purity |
| DE602005025391D1 (en) * | 2004-11-01 | 2011-01-27 | Seo Hong Yoo | METHOD AND COMPOSITIONS FOR REDUCING NEURODE GENERATION 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 |
| DE602005024303D1 (en) * | 2004-12-02 | 2010-12-02 | Sk Chemicals Co Ltd | PROCESS FOR THE OPTICAL SEPARATION OF AMLODIPIN |
| HUP0500570A3 (en) * | 2005-06-08 | 2008-03-28 | Richter Gedeon Nyrt | Process for the preparation of (s)-(-)-amlodipine |
| CN101247832B (en) * | 2005-06-27 | 2011-12-28 | 第一三共株式会社 | Pharmaceutical preparation containing an angiotensin II receptor antagonist and a calcium channel blocker |
| 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 a hydrate thereof and a pharmaceutical composition containing the same |
| TWI399223B (en) * | 2006-09-15 | 2013-06-21 | Daiichi Sankyo Co Ltd | Solid dosage form of olmesartan and amlodipine |
| KR100828883B1 (en) * | 2006-10-27 | 2008-05-09 | 씨제이제일제당 (주) | Separation Method of S-(-)-Amlodipine from Racemic Amlodipine |
| KR100830003B1 (en) * | 2006-10-31 | 2008-05-15 | 씨제이제일제당 (주) | Crystalline S-(-)-Amlodipine Adipic Acid Anhydride and Method for Preparing the Same |
| KR100868160B1 (en) | 2007-02-14 | 2008-11-12 | 한미약품 주식회사 | Method for preparing S-(-)-amlodipine or salts thereof and intermediates used therein |
| RU2357781C1 (en) * | 2008-02-06 | 2009-06-10 | Емельяна Зиповна Гильдеева | Amlodipine optical isomer separation method |
| KR100979772B1 (en) | 2008-06-12 | 2010-09-02 | 에이치 엘 지노믹스(주) | Method of Making Optically Pure S-(-)-Amlodipine Benzenesulfonate |
| KR100989970B1 (en) | 2008-07-01 | 2010-10-26 | 미래파인켐 주식회사 | Separation Method of (S)-(-)-Amlodipine |
| KR101085169B1 (en) | 2009-03-25 | 2011-11-18 | (주)켐트로스 | Separation Method of Amlodipine Optical Isomers |
| 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 |
| CN115850159B (en) * | 2022-11-11 | 2025-03-14 | 常州瑞明药业有限公司 | A kind of preparation method of levamlodipine maleate |
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| 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 |
| DK397686A (en) * | 1985-08-21 | 1987-02-22 | Glaxo Spa | HETEROCYCLIC COMPOUNDS |
| 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 |
| AU2614288A (en) * | 1987-10-27 | 1989-05-23 | Byk Gulden Lomberg Chemische Fabrik Gmbh | New pyrrolidines |
| 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 RU RU96119351A patent/RU2132845C1/en not_active IP Right Cessation
- 1995-03-06 DK DK95912222T patent/DK0751938T3/en active
- 1995-03-06 CA CA002186263A patent/CA2186263C/en not_active Expired - Fee Related
- 1995-03-06 EP EP95912222A patent/EP0751938B1/en not_active Expired - Lifetime
- 1995-03-06 CZ CZ19962784A patent/CZ287324B6/en not_active IP Right Cessation
- 1995-03-06 PL PL95316535A patent/PL180085B1/en not_active IP Right Cessation
- 1995-03-06 BR BR9507137A patent/BR9507137A/en not_active IP Right Cessation
- 1995-03-06 KR KR1019960705266A patent/KR100188980B1/en not_active Expired - Fee Related
- 1995-03-06 AT AT95912222T patent/ATE166050T1/en not_active IP Right Cessation
- 1995-03-06 DE DE69502486T patent/DE69502486T2/en not_active Expired - Fee Related
- 1995-03-06 NZ NZ282404A patent/NZ282404A/en unknown
- 1995-03-06 WO PCT/EP1995/000847 patent/WO1995025722A1/en not_active Ceased
- 1995-03-06 JP JP7524336A patent/JP2843681B2/en not_active Expired - Fee Related
- 1995-03-06 US US08/704,612 patent/US5750707A/en not_active Expired - Fee Related
- 1995-03-06 HU HU9602597A patent/HU214720B/en not_active IP Right Cessation
- 1995-03-06 ES ES95912222T patent/ES2116737T3/en not_active Expired - Lifetime
- 1995-03-06 CN CN95192238A patent/CN1067055C/en not_active Expired - Fee Related
- 1995-03-06 AU AU19493/95A patent/AU677765B2/en not_active Ceased
- 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2393150C2 (en) * | 2005-10-17 | 2010-06-27 | Ск Кемикалз Ко., Лтд. | Method of preparing chiral amlodipine gentisate |
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