BRPI0416648A2 - process for the preparation of pharmaceutically acceptable chiral salts of amlodipine - Google Patents
process for the preparation of pharmaceutically acceptable chiral salts of amlodipineInfo
- Publication number
- BRPI0416648A2 BRPI0416648A2 BRPI0416648-5A BRPI0416648A BRPI0416648A2 BR PI0416648 A2 BRPI0416648 A2 BR PI0416648A2 BR PI0416648 A BRPI0416648 A BR PI0416648A BR PI0416648 A2 BRPI0416648 A2 BR PI0416648A2
- Authority
- BR
- Brazil
- Prior art keywords
- preparation
- pharmaceutically acceptable
- amlodipine
- amiodipine
- chiral salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 title abstract 4
- 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 abstract 2
- 229960000528 amlodipine Drugs 0.000 title abstract 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 150000003892 tartrate salts Chemical class 0.000 abstract 1
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
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4422—1,4-Dihydropyridines, e.g. nifedipine, nicardipine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
PROCESSO PARA A PREPARAÇçO DE SAIS QUIRAIS FARMACEUTICAMENTE ACEITÁVEIS DE AMLODIPINA. A presente invenção refere-se a um processo para a preparação de sais farmaceuticamente aceitáveis de Amiodipina quiral, mais especificamente S(-) Amiodipina e R(+) Amiodipina sem isolar a base livre quiral na qual o produto tem uma pureza ótica variando entre 95 e 99% é descrito na presente invenção. O processo compreende resolver uma base RS de Arnlodipina usando ácido tartárico L(+) ou D(-) seguido pela reação do sal de tartrato separado com um ácido orgânico para obter o sal correspondente ao ácido usado com um ee variando a partir de 96 - 99%.PROCESS FOR THE PREPARATION OF PHARMACEUTICALLY ACCEPTABLE AMLODIPINE CHALAL SALTS. The present invention relates to a process for the preparation of pharmaceutically acceptable salts of chiral Amiodipine, more specifically S (-) Amiodipine and R (+) Amiodipine without isolating the chiral free base in which the product has an optical purity ranging from 95 ° C. and 99% is described in the present invention. The process comprises resolving an Arnlodipine RS base using L (+) or D (-) tartaric acid followed by reacting the separated tartrate salt with an organic acid to obtain the acid corresponding salt used with an ee ranging from 96 - 99%.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1440DE2003 | 2003-11-20 | ||
| PCT/IN2004/000324 WO2005049571A1 (en) | 2003-11-20 | 2004-10-19 | Process for preparation of chiral amlodipine salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0416648A2 true BRPI0416648A2 (en) | 2009-01-13 |
Family
ID=34611190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0416648-5A BRPI0416648A2 (en) | 2003-11-20 | 2004-10-19 | process for the preparation of pharmaceutically acceptable chiral salts of amlodipine |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1687273A1 (en) |
| KR (1) | KR20060086432A (en) |
| CN (1) | CN1882543A (en) |
| BR (1) | BRPI0416648A2 (en) |
| WO (1) | WO2005049571A1 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7858801B2 (en) * | 2004-10-20 | 2010-12-28 | Emcure Pharmaceuticals Limited | Process for producing enantiomer of amlodipine in high optical purity |
| KR101235116B1 (en) * | 2005-10-17 | 2013-02-20 | 에스케이케미칼주식회사 | Process for preparation of chiral amlodipine gentisate |
| KR100843400B1 (en) * | 2006-11-14 | 2008-07-04 | 씨제이제일제당 (주) | Crystalline S-(-)-Amlodipine Maleic Acid Anhydride and Method for Making the Same |
| CN101468986B (en) * | 2007-12-26 | 2010-12-29 | 香港南北兄弟国际投资有限公司 | Resolution method of dihydropyrimidine racemic compound |
| KR100979772B1 (en) * | 2008-06-12 | 2010-09-02 | 에이치 엘 지노믹스(주) | Method of Making Optically Pure S-(-)-Amlodipine Benzenesulfonate |
| KR101313842B1 (en) * | 2010-09-15 | 2013-10-01 | 대화제약 주식회사 | A manufacturing method of esamlodipine besilate and its hydrate |
| CN102516159B (en) * | 2011-12-15 | 2013-10-09 | 扬子江药业集团江苏海慈生物药业有限公司 | Method for producing S-(-)-amlodipine besylate |
| CN104592099A (en) * | 2014-12-30 | 2015-05-06 | 山东鲁抗医药股份有限公司 | Refining method for improving optical purity of levoamlodipine besylate |
| CN111689894B (en) * | 2019-03-13 | 2023-05-02 | 鲁南制药集团股份有限公司 | Levamlodipine besylate crystal form |
| CN112110850B (en) * | 2019-06-20 | 2023-05-02 | 鲁南制药集团股份有限公司 | Novel crystal form of levamlodipine besylate |
| 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 |
| CN116332832A (en) * | 2023-03-29 | 2023-06-27 | 安徽美致诚药业有限公司 | Maleic acid levo-amlodipine amorphous crystal form and preparation method thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9405833D0 (en) * | 1994-03-24 | 1994-05-11 | Pfizer Ltd | Separation of the enantiomers of amlodipine |
| MXPA03005885A (en) * | 2000-12-29 | 2005-04-19 | Pfizer Ltd | Process for making amlodipine maleate. |
| US6608206B1 (en) * | 2002-10-30 | 2003-08-19 | Council Of Scientific & Industrial Research | Process for making S(-) Amlodipine salts |
-
2004
- 2004-10-19 CN CNA2004800343754A patent/CN1882543A/en active Pending
- 2004-10-19 KR KR1020067009616A patent/KR20060086432A/en not_active Ceased
- 2004-10-19 EP EP04791865A patent/EP1687273A1/en not_active Withdrawn
- 2004-10-19 BR BRPI0416648-5A patent/BRPI0416648A2/en not_active IP Right Cessation
- 2004-10-19 WO PCT/IN2004/000324 patent/WO2005049571A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060086432A (en) | 2006-07-31 |
| CN1882543A (en) | 2006-12-20 |
| WO2005049571A1 (en) | 2005-06-02 |
| EP1687273A1 (en) | 2006-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08F | Application fees: application dismissed [chapter 8.6 patent gazette] |
Free format text: REFERENTE AS 3A, 4A, 5A, 6A E 7A ANUIDADES. |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: REFERENTE AO DESPACHO 8.6 PUBLICADO NA RPI 2158 DE 15/05/2012. |