CA2352436A1 - Polymorphs of telmisartan, processes for preparing them and their use in the preparation of a pharmaceutical composition - Google Patents
Polymorphs of telmisartan, processes for preparing them and their use in the preparation of a pharmaceutical composition Download PDFInfo
- Publication number
- CA2352436A1 CA2352436A1 CA002352436A CA2352436A CA2352436A1 CA 2352436 A1 CA2352436 A1 CA 2352436A1 CA 002352436 A CA002352436 A CA 002352436A CA 2352436 A CA2352436 A CA 2352436A CA 2352436 A1 CA2352436 A1 CA 2352436A1
- Authority
- CA
- Canada
- Prior art keywords
- telmisartan
- organic solvent
- process according
- preparing
- polymorphs
- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention relates to polymorphs of 4'-[2-n-propyl-4-methyl-6(1- methylbenzimidazol -2-yl) benzimidazol -1-ylmethyl] biphenyl-2-carboxylic ac id (INN: telmisartan), and in particular the polymorphous form B of formula (I) , characterized by an endothermic peak at 183 ~ 2~C during thermal analysis by differential scanning calorimetry. The invention also relates to mixtures of said polymorphs, methods for producing telmisartan containing form B and to the use thereof in the preparation of a medicament.
Claims (9)
1) Polymorphic crystal modification B (form B) of telmisartan (formula I), characterised by an endothermic maximum at 183~2°C which occurs during thermal analysis using DSC.
2) Telmisartan, characterised in that it contains form B
according to claim 1.
according to claim 1.
3) Process for preparing telmisartan according to one of claims 1 and 2, characterised in that a) telmisartan is taken up in a mixture of solvents consisting of water, formic acid and an organic solvent miscible therewith, heated, and the resulting solution is then filtered, b) the organic solvent is distilled off, optionally while water is simultaneously added in metered amounts, c) the telmisartan form B is precipitated out of the remaining solution by the addition of a base and d) the product precipitated is centrifuged, washed and dried.
4) Process according to claim 3, characterised in that organic carboxylic acid esters, ketones or ethers are used as the organic solvent.
5) Process according to claim 3 or 4, characterised in that acetone, methylethylketone, methyl acetate, ethyl acetate, ethyl formate, ethyleneglycol dimethylether or tetrahydrofuran is used as the organic solvent.
6) Process according to claim 3, 4 or 5, characterised in that acetone, methylethylketone, methyl acetate, ethyl acetate or tetrahydrofuran is used as the organic solvent.
7) Process according to claim 3, 4, 5 or 6, characterised in that ethyl acetate is used as the organic solvent.
8) Process according to claim 3, 4, 5, 6 or 7, characterised in that ammonia is used as the base.
9) Use of telmisartan according to claim 1 or 2 for preparing a pharmaceutical composition.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19901921.5 | 1999-01-19 | ||
| DE19901921A DE19901921C2 (en) | 1999-01-19 | 1999-01-19 | Polymorphs of telmisartan, process for their preparation and their use in the manufacture of a medicament |
| PCT/EP2000/000065 WO2000043370A1 (en) | 1999-01-19 | 2000-01-07 | Telmisartan polymorphs, methods for producing same and their use in the preparation of a medicament |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2352436A1 true CA2352436A1 (en) | 2000-07-27 |
| CA2352436C CA2352436C (en) | 2010-03-23 |
Family
ID=7894715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2352436A Expired - Fee Related CA2352436C (en) | 1999-01-19 | 2000-01-07 | Polymorphs of telmisartan, processes for preparing them and their use in the preparation of a pharmaceutical composition |
Country Status (36)
| Country | Link |
|---|---|
| EP (1) | EP1144386B1 (en) |
| JP (1) | JP4700813B2 (en) |
| KR (1) | KR100658959B1 (en) |
| CN (1) | CN1144790C (en) |
| AR (1) | AR035475A1 (en) |
| AT (1) | ATE252564T1 (en) |
| AU (1) | AU765081B2 (en) |
| BG (1) | BG65027B1 (en) |
| BR (1) | BR0007584A (en) |
| CA (1) | CA2352436C (en) |
| CO (1) | CO5150238A1 (en) |
| CZ (1) | CZ297412B6 (en) |
| DE (2) | DE19901921C2 (en) |
| DK (1) | DK1144386T3 (en) |
| EA (1) | EA003065B1 (en) |
| EE (1) | EE04344B1 (en) |
| ES (1) | ES2208265T3 (en) |
| HK (1) | HK1041485B (en) |
| HR (1) | HRP20010514B1 (en) |
| HU (1) | HU227401B1 (en) |
| IL (2) | IL143634A0 (en) |
| MY (1) | MY122755A (en) |
| NO (1) | NO319823B1 (en) |
| NZ (1) | NZ513528A (en) |
| PE (1) | PE20001362A1 (en) |
| PL (1) | PL211829B1 (en) |
| PT (1) | PT1144386E (en) |
| RS (1) | RS50044B (en) |
| SA (1) | SA99200838B1 (en) |
| SK (1) | SK285429B6 (en) |
| TR (1) | TR200102074T2 (en) |
| TW (1) | TWI280241B (en) |
| UA (1) | UA56358C2 (en) |
| UY (1) | UY25980A1 (en) |
| WO (1) | WO2000043370A1 (en) |
| ZA (1) | ZA200104771B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9308197B2 (en) | 2006-10-06 | 2016-04-12 | Boehringer Ingelheim Vetmedica Gmbh | Angiotensin II receptor antagonist for the prevention or treatment of systemic diseases in cats |
| US9993432B2 (en) | 2008-11-27 | 2018-06-12 | Bayer Intellectual Property Gmbh | Pharmaceutical dosage form comprising nifedipine or nisoldipine and an angiotensin II antagonist and/or a diuretic |
| US10314782B2 (en) | 2009-05-20 | 2019-06-11 | Boehringer Ingelheim Vetmedica Gmbh | Oral suspension comprising telmisartan |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6737432B2 (en) | 2001-10-31 | 2004-05-18 | Boehringer Ingelheim Pharma Kg | Crystalline form of telmisartan sodium |
| DE10153737A1 (en) * | 2001-10-31 | 2003-05-28 | Boehringer Ingelheim Pharma | Crystalline sodium salt of telmisartan, process for its preparation and its use for the manufacture of a medicament |
| PT1467712E (en) * | 2002-01-16 | 2008-01-09 | Boehringer Ingelheim Pharma | Bilayer pharmaceutical tablet comprising telmisartan and hydrochlorothiazide |
| DE10314702A1 (en) | 2003-03-31 | 2004-10-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Process for the preparation of telmisartan |
| GB2414019A (en) * | 2004-05-11 | 2005-11-16 | Cipla Ltd | One-step preparation of telmisartan by condensation and hydrolysis |
| JP2008503595A (en) | 2004-10-15 | 2008-02-07 | テバ ファーマシューティカル インダストリーズ リミティド | Preparation of telmisartan |
| US7943781B2 (en) | 2004-10-18 | 2011-05-17 | Dr. Reddy's Laboratories Limited | Process for preparing telmisartan |
| US8637078B2 (en) | 2005-11-24 | 2014-01-28 | Boehringer Ingelheim International Gmbh | Bilayer tablet comprising telmisartan and diuretic |
| EP2443094B1 (en) | 2009-06-19 | 2013-03-20 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for the preparation of telmisartan |
| EP2277866A1 (en) | 2009-06-22 | 2011-01-26 | Inke, S.A. | Process for preparing telmisartan |
| WO2011002425A2 (en) | 2009-07-02 | 2011-01-06 | Bilgig Mahmut | Pharmaceutical composition increasing solubility and stability |
| EP2448576A2 (en) | 2009-07-02 | 2012-05-09 | Mahmut Bilgic | Solubility enhancing pharmaceutical composition |
| EA025946B1 (en) | 2010-10-27 | 2017-02-28 | Крка, Товарна Здравил, Д. Д., Ново Место | Multilayer pharmaceutical composition comprising telmisartan and amlodipine |
| ITMI20102416A1 (en) * | 2010-12-27 | 2012-06-28 | Chemelectiva S R L | INTERMEDIATE FOR THE PREPARATION OF AN ACTIVE PRINCIPLE AND PROCESS FOR ITS PREPARATION |
| EP2612658A1 (en) | 2012-01-05 | 2013-07-10 | Laboratorios Lesvi, S.L. | Pharmaceutical compositions of 4'-[(1,4'dimethyl-2'-propyl[2,6'-bi-1h-benzimidazol]-1'-yl)methyl]-[1,1'-biphenyl]-2-carboxylic acid and is 6-chloro-3,4-dihydro-2h-1,2,4-benzothiadiazine-7-sulfonamide-1,1-dioxide |
| JP6147546B2 (en) * | 2013-04-10 | 2017-06-14 | 株式会社トクヤマ | Method for producing telmisartan A-type crystals with reduced acetic acid |
| EP2979691A1 (en) | 2014-07-30 | 2016-02-03 | Boehringer Ingelheim International GmbH | Oral disintegrating tablet |
| JP6275596B2 (en) * | 2014-09-03 | 2018-02-07 | 株式会社トクヤマ | Method for producing ammonium salt of telmisartan |
| JP5871294B1 (en) | 2015-02-27 | 2016-03-01 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Immediate release oral tablets |
| KR20170001921A (en) | 2015-06-26 | 2017-01-05 | 대원제약주식회사 | A pharmaceutical composition comprising telmisartan with increased stability and a preparation method thereof |
| KR20170012703A (en) | 2015-07-22 | 2017-02-03 | 대원제약주식회사 | A pharmaceutical composition comprising telmisartan and a preparation method thereof |
| EP3463309B1 (en) | 2016-05-30 | 2020-06-17 | Boehringer Ingelheim International GmbH | Fixed dose combination of telmisartan, hydrochlorothiazide and amlodipine |
| KR102044223B1 (en) * | 2016-09-12 | 2019-11-13 | 성균관대학교산학협력단 | Solid dispersions comprising Telmisartan and the preparation method thereof |
| CN106749037B (en) * | 2016-12-21 | 2019-06-21 | 山东大学 | A kind of unformed Telmisartan-glutaric acid eutectic and its preparation method and application |
| CN106749036B (en) * | 2016-12-21 | 2019-06-21 | 山东大学 | A kind of unformed Telmisartan-pimelic acid eutectic and its preparation method and application |
| WO2019008077A1 (en) | 2017-07-07 | 2019-01-10 | Boehringer Ingelheim Vetmedica Gmbh | Angiotensin ii receptor antagonist for the prevention or treatment of systemic diseases in cats |
| CN109851562A (en) * | 2019-01-30 | 2019-06-07 | 浙江省食品药品检验研究院 | A kind of Telmisartan crystal and preparation method thereof |
| WO2023001880A1 (en) | 2021-07-22 | 2023-01-26 | Krka, D. D., Novo Mesto | Bilayer tablet comprising telmisartan and indapamide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI9210098B (en) * | 1991-02-06 | 2000-06-30 | Dr. Karl Thomae | Benzimidazoles, drugs with this compounds, and process for their preparation |
| US5139114A (en) * | 1991-03-18 | 1992-08-18 | Abex Corporation | Visible brake block wear indicator |
-
1999
- 1999-01-19 DE DE19901921A patent/DE19901921C2/en not_active Expired - Fee Related
- 1999-12-17 PE PE1999001284A patent/PE20001362A1/en not_active Application Discontinuation
- 1999-12-26 SA SA99200838A patent/SA99200838B1/en unknown
-
2000
- 2000-01-07 AT AT00901510T patent/ATE252564T1/en active
- 2000-01-07 EP EP00901510A patent/EP1144386B1/en not_active Expired - Lifetime
- 2000-01-07 EE EEP200100375A patent/EE04344B1/en not_active IP Right Cessation
- 2000-01-07 PL PL349425A patent/PL211829B1/en unknown
- 2000-01-07 AU AU22881/00A patent/AU765081B2/en not_active Ceased
- 2000-01-07 DK DK00901510T patent/DK1144386T3/en active
- 2000-01-07 SK SK1020-2001A patent/SK285429B6/en not_active IP Right Cessation
- 2000-01-07 EA EA200100730A patent/EA003065B1/en not_active IP Right Cessation
- 2000-01-07 IL IL14363400A patent/IL143634A0/en active IP Right Grant
- 2000-01-07 JP JP2000594786A patent/JP4700813B2/en not_active Expired - Lifetime
- 2000-01-07 CN CNB00802880XA patent/CN1144790C/en not_active Expired - Fee Related
- 2000-01-07 TR TR2001/02074T patent/TR200102074T2/en unknown
- 2000-01-07 KR KR1020017008958A patent/KR100658959B1/en not_active IP Right Cessation
- 2000-01-07 HU HU0105148A patent/HU227401B1/en not_active IP Right Cessation
- 2000-01-07 DE DE50004150T patent/DE50004150D1/en not_active Expired - Lifetime
- 2000-01-07 ES ES00901510T patent/ES2208265T3/en not_active Expired - Lifetime
- 2000-01-07 WO PCT/EP2000/000065 patent/WO2000043370A1/en active IP Right Grant
- 2000-01-07 CZ CZ20012634A patent/CZ297412B6/en not_active IP Right Cessation
- 2000-01-07 RS YUP-511/01A patent/RS50044B/en unknown
- 2000-01-07 NZ NZ513528A patent/NZ513528A/en not_active IP Right Cessation
- 2000-01-07 CA CA2352436A patent/CA2352436C/en not_active Expired - Fee Related
- 2000-01-07 PT PT00901510T patent/PT1144386E/en unknown
- 2000-01-07 BR BR0007584-1A patent/BR0007584A/en active Pending
- 2000-01-17 TW TW089100637A patent/TWI280241B/en not_active IP Right Cessation
- 2000-01-17 MY MYPI20000130A patent/MY122755A/en unknown
- 2000-01-18 CO CO00002435A patent/CO5150238A1/en unknown
- 2000-01-18 UY UY25980A patent/UY25980A1/en not_active Application Discontinuation
- 2000-01-19 AR ARP000100241A patent/AR035475A1/en active Pending
- 2000-07-01 UA UA2001085811A patent/UA56358C2/en unknown
-
2001
- 2001-06-07 IL IL143634A patent/IL143634A/en not_active IP Right Cessation
- 2001-06-12 ZA ZA200104771A patent/ZA200104771B/en unknown
- 2001-06-27 BG BG105654A patent/BG65027B1/en active Active
- 2001-07-10 HR HR20010514A patent/HRP20010514B1/en not_active IP Right Cessation
- 2001-07-18 NO NO20013560A patent/NO319823B1/en not_active IP Right Cessation
-
2002
- 2002-04-24 HK HK02103090.1A patent/HK1041485B/en not_active IP Right Cessation
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9308197B2 (en) | 2006-10-06 | 2016-04-12 | Boehringer Ingelheim Vetmedica Gmbh | Angiotensin II receptor antagonist for the prevention or treatment of systemic diseases in cats |
| US9585873B2 (en) | 2006-10-06 | 2017-03-07 | Boehringer Ingelheim Vetmedica Gmbh | Angiotensin II receptor antagonist for the prevention or treatment of systemic diseases in cats |
| US9949954B2 (en) | 2006-10-06 | 2018-04-24 | Boehringer Ingelheim Vetmedica Gmbh | Angiotensin II receptor antagonist for the prevention or treatment of systemic diseases in cats |
| US10357479B2 (en) | 2006-10-06 | 2019-07-23 | Boehringer Ingelheim Vetmedica Gmbh | Angiotensin II receptor antagonist for the prevention or treatment of systemic diseases in cats |
| US9993432B2 (en) | 2008-11-27 | 2018-06-12 | Bayer Intellectual Property Gmbh | Pharmaceutical dosage form comprising nifedipine or nisoldipine and an angiotensin II antagonist and/or a diuretic |
| US10314782B2 (en) | 2009-05-20 | 2019-06-11 | Boehringer Ingelheim Vetmedica Gmbh | Oral suspension comprising telmisartan |
| US10537523B2 (en) | 2009-05-20 | 2020-01-21 | Boehringer Ingelheim Vetmedica Gmbh | Oral suspension comprising telmisartan |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160107 |