CA2160725A1 - Process for the preparation of a tetrazole derivative in two crystalline forms and novel crystalline form of said derivative - Google Patents

Process for the preparation of a tetrazole derivative in two crystalline forms and novel crystalline form of said derivative

Info

Publication number
CA2160725A1
CA2160725A1 CA002160725A CA2160725A CA2160725A1 CA 2160725 A1 CA2160725 A1 CA 2160725A1 CA 002160725 A CA002160725 A CA 002160725A CA 2160725 A CA2160725 A CA 2160725A CA 2160725 A1 CA2160725 A1 CA 2160725A1
Authority
CA
Canada
Prior art keywords
derivative
diazaspiro
tetrazol
biphenyl
methyl
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
Application number
CA002160725A
Other languages
French (fr)
Other versions
CA2160725C (en
Inventor
Antoine Caron
Dominique Chantreux
Colette Bouloumie
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis France
Original Assignee
Sanofi SA
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 Sanofi SA filed Critical Sanofi SA
Publication of CA2160725A1 publication Critical patent/CA2160725A1/en
Application granted granted Critical
Publication of CA2160725C publication Critical patent/CA2160725C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • A61P9/12—Antihypertensives

Abstract

The present invention relates to a process for the preparation of the 2-n.butyl-3-[[2'-(tetrazol-5-yl) biphenyl-4-yl] methyl]-1,3-diazaspiro[4.4]-non-1-en-4-one by reaction of the corresponding nitrile with an alkaline azide and triethylamine hydrochloride, recovering the 2-n.butyl-3-[[2'-(tetrazol-5-yl) biphenyl-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one in form of one of its alkaline salts in aqueous solution, by neutralization of said alkaline salt and crystallization of the 2-n.butyt-3-[[2'-(tetrazol-5-yl)-biphenyl-4-yl]methyl]-1,3-diazaspiro[4.4] non-1-en-4-one thus precipitated either in a solvent containing less than 10% of water or in a solvent containing more than 10% of water in order to obtain two different crystalline forms (Forms A and B). Furthermore a novel crystalline form (Form B) of 2-n.butyl-3-[[2'-(tetrazol-5-yl)biphenyl-4-yl] methyl]-1,3-diazaspiro[4.4] non-1-en-4-one and pharmaceutical compositions containing it are described. Form A has the X-ray powder diffraction pattern given in Table II:
TABLE II

dI/I o 18.98100.00 10.895.81 9.497.43 8.486.60 7.1346.23 6.6811.25 6.307.45 5.458.85 5.2216.82 5.0311.81 4.7115.91 4.5845.40 4.4426.12 4.3225.44 4.2225.86 4.1121.72 3.9325.46 3.8533.89 3.77 27.76 3.38 9.09 3.33 11.75 3.23 13.68 3.14 11.99 2.80 8.97 2.71 9.50 Form B has the X-ray powder diffraction pattern given in Table I:
TABLE I

d I/I o 11.22 100.00 7.90 12.02 7.52 13.79 7.23 18.60 6.27 20.14 6.09 6.47 5.86 7.42 5.60 98.76 5.41 19.45 5.05 24.67 4.97 20.36 4.91 12.92 4.80 27.33 4.61 15.90 4.49 14.73 4.36 9.86 4.17 62.84 4.07 15.39 3.97 30.34 3.88 14.32 3.83 13.56 3.75 37.28 3.53 26.48 3.46 12.42 3.40 27.88 3.27 11.03 3.18 10.42 3.15 7.28 3.12 6.11 3.05 15.50 3.01 9.49 2.81 7.11 2.78 9.40
CA002160725A 1994-10-19 1995-10-17 Process for the preparation of a tetrazole derivative in two crystalline forms and novel crystalline form of said derivative Expired - Fee Related CA2160725C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9412459 1994-10-19
FR9412459A FR2725987B1 (en) 1994-10-19 1994-10-19 PROCESS FOR THE PREPARATION OF A TETRAZOLE DERIVATIVE IN TWO CRYSTALLINE FORMS AND NOVEL CRYSTALLINE FORM THEREOF

Publications (2)

Publication Number Publication Date
CA2160725A1 true CA2160725A1 (en) 1996-04-20
CA2160725C CA2160725C (en) 2001-12-18

Family

ID=9467986

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002160725A Expired - Fee Related CA2160725C (en) 1994-10-19 1995-10-17 Process for the preparation of a tetrazole derivative in two crystalline forms and novel crystalline form of said derivative

Country Status (27)

Country Link
US (1) US5629331A (en)
EP (1) EP0708103B1 (en)
JP (1) JP3366786B2 (en)
KR (1) KR100251222B1 (en)
CN (1) CN1061656C (en)
AT (1) ATE198478T1 (en)
AU (1) AU698041B2 (en)
CA (1) CA2160725C (en)
CY (1) CY2277B1 (en)
CZ (2) CZ288629B6 (en)
DE (1) DE69519788T2 (en)
DK (1) DK0708103T3 (en)
ES (1) ES2155115T3 (en)
FI (1) FI114156B (en)
FR (1) FR2725987B1 (en)
GR (1) GR3035503T3 (en)
HK (1) HK1005135A1 (en)
HU (1) HU226461B1 (en)
IL (1) IL115688A (en)
NO (1) NO307516B1 (en)
NZ (1) NZ280293A (en)
PL (1) PL184193B1 (en)
PT (1) PT708103E (en)
RU (1) RU2144536C1 (en)
SI (1) SI0708103T1 (en)
TW (1) TW357147B (en)
ZA (1) ZA958850B (en)

Families Citing this family (31)

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Publication number Priority date Publication date Assignee Title
US5994348A (en) 1995-06-07 1999-11-30 Sanofi Pharmaceutical compositions containing irbesartan
TW442301B (en) * 1995-06-07 2001-06-23 Sanofi Synthelabo Pharmaceutical compositions containing irbesartan
FR2780403B3 (en) 1998-06-24 2000-07-21 Sanofi Sa NOVEL FORM OF IRBESARTAN, METHODS FOR OBTAINING SAID FORM AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
TR200100149T2 (en) 1998-07-06 2001-10-22 Bristol-Myers Squibb Company Biphenyl-sulfonamides as dual angiotensin endothelin receptor antagonists
WO2003050110A1 (en) * 2001-12-10 2003-06-19 Dr. Reddy's Laboratories Ltd. Amorphous form of 2-n-butyl-3-( (2-(1h-tetrazol-5-yl) (1,1'-biphenyl)-4-yl) methyl) -1,3-diazaspiro (4,4') non-1-en-4-one
US20050176794A1 (en) * 2002-07-16 2005-08-11 Ben-Zion Dolitzky Novel synthesis of irbesartan
EP2039693A3 (en) 2003-01-16 2009-06-17 Teva Pharmaceutical Industries Limited Novel synthesis of irbesartan
CA2515138A1 (en) * 2003-02-05 2004-08-26 Teva Pharmaceutical Industries Ltd. Synthesis of 2-butyl-3-(2'-(1-trityl-1h-tetrazol-5-yl)biphenyl-4-yl)-1,3-diazaspirol[4,4]-non-ene-4-one
AU2003242984A1 (en) * 2003-04-07 2004-11-01 Hetero Drugs Limited A novel crystalline form of irbesartan
WO2005051943A1 (en) * 2003-11-28 2005-06-09 Ranbaxy Laboratories Limited Processes for the preparation of highly pure irbesartan
PL1750862T3 (en) 2004-06-04 2011-06-30 Teva Pharma Pharmaceutical composition containing irbesartan
WO2006001026A1 (en) * 2004-06-23 2006-01-05 Hetero Drugs Limited Irbesartan polymorphs
SI21849A (en) * 2004-07-29 2006-02-28 Krka, Tovarna Zdravil, D.D., Novo Mesto Preparation of hydrochloride salts of tetrazole derivative
TWI346108B (en) 2004-08-23 2011-08-01 Bristol Myers Squibb Co A method for preparing irbesartan and intermediates thereof
GB2419592A (en) * 2004-10-26 2006-05-03 Cipla Ltd Process for the preparation of irbesartan hydrochloride
SI1812422T1 (en) 2004-11-11 2014-05-30 Lek Pharmaceuticals D.D. Polymorph form of irbesartan
ES2259909B1 (en) * 2005-02-28 2007-06-16 Inke, S.A. PROCEDURE FOR OBTAINING A PHARMACEUTICALLY ACTIVE COMPOUND AND ITS SYNTHESIS INTERMEDIATE.
EP1951714A1 (en) 2005-07-27 2008-08-06 Jubilant Organosys Limited Process for producing 2-(n-butyl)-3-[[2'-(tetrazol-5-yl)biphenyl- 4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one
SI1806130T1 (en) 2006-01-09 2010-06-30 KRKA@@d@d@@@Novo@mesto Solid pharmaceutical composition comprising irbesartan
WO2008041957A1 (en) * 2006-10-03 2008-04-10 Ulkar Kimya Sanayi Ve Ticaret As Method for producing pure crystalline form of 2-n-butyl-3-((2-(1h-tetrazole-5-yl) (1,1'-biphenyl)-4-methyl)-1,3-diazapspiro (4,4') non -1- en-4-one
EP1918288A1 (en) 2006-11-02 2008-05-07 Cadila Pharmaceuticals Limited A novel and improved process for the preparation of Irbesartan, an angiotensin-II receptor antagonist for the treatment of hypertension
PT2065035E (en) * 2007-11-28 2010-10-04 Lesvi Laboratorios Sl Pharmaceutical formulations containing irbesartan
WO2009072137A2 (en) * 2007-12-07 2009-06-11 Hetero Drugs Limited Process for pure irbesartan
KR101009383B1 (en) * 2008-04-30 2011-01-19 켐젠주식회사 Preparation of high purity 2-butyl-3-[[2?-1H-tetrazol-5-yl[1,1?-biphenyl]-4-yl]methyl]-1,3-diazaspiro[4,4]non-1-en-4-on
WO2010116380A2 (en) * 2009-04-08 2010-10-14 Ctx Life Sciences Pvt. Ltd. A one pot process for preparing 2-butyl-3-[[2'-(1h-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1,3-diazaspiro [4, 4] non-1-en-4-one (irbesartan)
AR078107A1 (en) * 2009-08-31 2011-10-12 Sanofi Aventis USE OF IRBESARTAN FOR THE PREPARATION OF A MEDICINAL PRODUCT FOR THE PREVENTION OF HOSPITALIZATION BY CARDIAC INSUFFICIENCY
US8080670B2 (en) 2010-05-04 2011-12-20 Divi's Laboratories, Ltd. Process for the preparation of irbesartan
FR2977253B1 (en) 2011-06-30 2013-08-09 Centre Nat Rech Scient ALCOXYLIC ORGANOSTANNIC REAGENT SUPPORTED, PREPARED AND USED FOR THE SYNTHESIS OF HETEROGENEOUS PHASE TETRAZOLES
WO2018002673A1 (en) 2016-07-01 2018-01-04 N4 Pharma Uk Limited Novel formulations of angiotensin ii receptor antagonists
US11655220B2 (en) 2020-10-22 2023-05-23 Hetero Labs Limited Process for the preparation of angiotensin II receptor blockers
CA3233738A1 (en) 2021-10-01 2023-04-06 Sanofi Process for preparing sartan active compounds having a tetrazole ring

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2697919B2 (en) * 1989-09-29 1998-01-19 キヤノン株式会社 Signal interpolation circuit and displacement measuring device provided with the circuit
IE70593B1 (en) * 1989-09-29 1996-12-11 Eisai Co Ltd Biphenylmethane derivative the use of it and pharmacological compositions containing same
IL99372A0 (en) * 1990-09-10 1992-08-18 Ciba Geigy Ag Azacyclic compounds

Also Published As

Publication number Publication date
AU3433595A (en) 1996-05-02
DE69519788T2 (en) 2001-08-30
FI114156B (en) 2004-08-31
NZ280293A (en) 1997-10-24
AU698041B2 (en) 1998-10-22
CA2160725C (en) 2001-12-18
HU226461B1 (en) 2008-12-29
EP0708103B1 (en) 2001-01-03
FR2725987A1 (en) 1996-04-26
NO954154D0 (en) 1995-10-18
US5629331A (en) 1997-05-13
IL115688A (en) 1999-09-22
CY2277B1 (en) 2003-07-04
PT708103E (en) 2001-06-29
CZ271095A3 (en) 1996-05-15
TW357147B (en) 1999-05-01
FR2725987B1 (en) 1997-01-10
KR100251222B1 (en) 2000-05-01
HUT73179A (en) 1996-06-28
CZ288624B6 (en) 2001-08-15
FI954992A (en) 1996-04-20
NO307516B1 (en) 2000-04-17
PL184193B1 (en) 2002-09-30
JP3366786B2 (en) 2003-01-14
JPH08208642A (en) 1996-08-13
NO954154L (en) 1996-04-22
IL115688A0 (en) 1996-01-19
CN1128261A (en) 1996-08-07
KR960014122A (en) 1996-05-22
CN1061656C (en) 2001-02-07
ATE198478T1 (en) 2001-01-15
SI0708103T1 (en) 2001-04-30
GR3035503T3 (en) 2001-06-29
ES2155115T3 (en) 2001-05-01
HU9503016D0 (en) 1995-12-28
ZA958850B (en) 1996-05-27
EP0708103A1 (en) 1996-04-24
DK0708103T3 (en) 2001-04-23
FI954992A0 (en) 1995-10-19
CZ288629B6 (en) 2001-08-15
RU2144536C1 (en) 2000-01-20
HK1005135A1 (en) 1998-12-24
DE69519788D1 (en) 2001-02-08
PL311012A1 (en) 1996-04-29

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