WO2012028925A3 - Process for the preparation of telmisartan - Google Patents

Process for the preparation of telmisartan Download PDF

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Publication number
WO2012028925A3
WO2012028925A3 PCT/IB2011/001973 IB2011001973W WO2012028925A3 WO 2012028925 A3 WO2012028925 A3 WO 2012028925A3 IB 2011001973 W IB2011001973 W IB 2011001973W WO 2012028925 A3 WO2012028925 A3 WO 2012028925A3
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
propyl
telmisartan
dmpbb
give
Prior art date
Application number
PCT/IB2011/001973
Other languages
French (fr)
Other versions
WO2012028925A2 (en
Inventor
Chakrapani Lakkoju
Naga Raju Koneti
Sridhar Kokkalla
Sambhu Prasad Sarma Mallela
Nanoranjan Choudary Boyapati
Original Assignee
Ogene Systems (I) Pvt Ltd
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
Application filed by Ogene Systems (I) Pvt Ltd filed Critical Ogene Systems (I) Pvt Ltd
Publication of WO2012028925A2 publication Critical patent/WO2012028925A2/en
Publication of WO2012028925A3 publication Critical patent/WO2012028925A3/en

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
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Methyl-4-(butyramido)-3-methyl-5-nitrobenzoate is treated with sulphur containing reducing agent to give methyl-4-methyl-2-propyl-lH-benzimidazole-6-carboxylate, which is further hydrolyzed to the corresponding acid, 2-n-propyl-4-methyl-6- carboxy benzimidazole. The critical intermediate l,4'-dimethyl-2'-propyl-lH,3'H- 2,6'-bisbenzimidazol (DMPBB) is prepared by treating the above acid with N- mehtyl-o-phenylenediamine dihydrochloride under acidic conditions. Reaction of 4'-halomethylbiphenyl-2-carboxylic acid alkyl ester with DMPBB in presence of base to give Telmisartan ester which is further converted to Telmisartan of Formula (I).
PCT/IB2011/001973 2010-09-03 2011-08-29 An improved process for the preparation of telmisartan WO2012028925A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2561CH2010 2010-09-03
IN2561CHE2010 2010-09-03

Publications (2)

Publication Number Publication Date
WO2012028925A2 WO2012028925A2 (en) 2012-03-08
WO2012028925A3 true WO2012028925A3 (en) 2012-04-26

Family

ID=44801033

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2011/001973 WO2012028925A2 (en) 2010-09-03 2011-08-29 An improved process for the preparation of telmisartan

Country Status (1)

Country Link
WO (1) WO2012028925A2 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103787982A (en) * 2012-10-31 2014-05-14 上海特化医药科技有限公司 Telmisartan preparation method and intermediate of telmisartan
JP6210599B2 (en) * 2014-02-26 2017-10-11 株式会社トクヤマ Process for producing 4-methyl-6 (1-methylbenzimidazol-2-yl) -2-n-propyl-1H-benzimidazole
CN104974096B (en) * 2015-07-07 2019-02-01 威海迪素制药有限公司 A kind of preparation method of telmisartan intermediate
CN106008356B (en) * 2016-06-07 2023-02-28 浙江华海药业股份有限公司 Preparation method of telmisartan
KR102653426B1 (en) 2017-11-13 2024-03-29 에코랍 유에스에이 인코퍼레이티드 A novel single-reactor homogeneous method for large-scale production of 2-substituted benzimidazoles
CN108250148B (en) * 2017-12-29 2021-06-08 江苏中邦制药有限公司 Refining method of telmisartan key intermediate
CN112441984B (en) * 2019-08-29 2024-04-19 上海特化医药科技有限公司 Benzimidazole-substituted phenyl n-butyramide-based compound and preparation method thereof
CN111170947A (en) * 2019-10-23 2020-05-19 江苏中邦制药有限公司 Preparation method of telmisartan impurity J
CN111041516B (en) * 2019-12-19 2021-06-25 湖南大学 New preparation method of telmisartan intermediate of antihypertensive drug
CN111808027A (en) * 2020-05-25 2020-10-23 重庆康刻尔制药有限公司 Purification method of telmisartan intermediate

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5591762A (en) * 1991-02-06 1997-01-07 Dr. Karl Thomae Gmbh Benzimidazoles useful as angiotensin-11 antagonists
WO2006044648A1 (en) * 2004-10-15 2006-04-27 Teva Pharmaceutical Industries Ltd. Process for preparing telmisartan

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6358986B1 (en) 1999-01-19 2002-03-19 Boehringer Ingelheim Pharma Kg Polymorphs of telmisartan
DE19917524C2 (en) 1999-04-17 2001-09-20 Boehringer Ingelheim Pharma Process for the nitration of aniline derivatives
CN1182122C (en) 2001-07-30 2004-12-29 中国科学院上海药物研究所 Synthesis path of Timisatem
CN1204124C (en) 2001-10-15 2005-06-01 中国科学院上海药物研究所 New preparation method of timixatan
US6770762B2 (en) 2002-01-18 2004-08-03 Boehringer Ingelheim Pharma Gmbh & Co. Kg Process for preparing and purifying 1,7′-dimethyl-2′-propyl-2,5′-bi-1H-benzimidazole
AU2003902860A0 (en) 2003-06-06 2003-06-26 Daicel Chemical Industries, Ltd Benzimidazole compounds
DE102005034279A1 (en) 2005-07-22 2007-01-25 Boehringer Ingelheim Pharma Gmbh & Co. Kg Preparation of 1,7'-dimethyl-2'-propyl-2,5'-bi-1H-benzimidazole
EP2280947B1 (en) 2008-05-02 2014-11-26 Boehringer Ingelheim International GmbH Production of 1,7´-dimethyl-2´-propyl-2,5´-bi-1h-benzimidazole

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5591762A (en) * 1991-02-06 1997-01-07 Dr. Karl Thomae Gmbh Benzimidazoles useful as angiotensin-11 antagonists
WO2006044648A1 (en) * 2004-10-15 2006-04-27 Teva Pharmaceutical Industries Ltd. Process for preparing telmisartan

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
REDDY KIKKURU SRIRAMI ET AL: "An Efficient and Impurity-Free Process for Telmisartan: An Antihypertensive Drug", ORGANIC PROCESS RESEARCH AND DEVELOPMENT, AMERICAN CHEMICAL SOCIETY, US, vol. 11, 1 January 2007 (2007-01-01), pages 81 - 85, XP002548424, ISSN: 1083-6160, [retrieved on 20061012], DOI: 10.1021/OP060200G *
RIES ET AL: "6-Substituted benzimidazoles as new nonpeptide angiotensin II receptor antagonists: Synthesis, biological activity, and structure-activity relationships", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 36, no. 25, 1 January 1993 (1993-01-01), pages 4040 - 4051, XP002142236, ISSN: 0022-2623, DOI: 10.1021/JM00077A007 *
YANG ET AL.: "Facile Synthesis of Novel Nonpeptide Angiotensin II Receptor Antagonists", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 40, no. 6, 2003, pages 1107 - 1112, XP002668702 *

Also Published As

Publication number Publication date
WO2012028925A2 (en) 2012-03-08

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