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 derivativeInfo
- 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
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
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
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)
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 |
CA2336714A1 (en) | 1998-07-06 | 2000-01-13 | 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 |
ATE340793T1 (en) * | 2002-07-16 | 2006-10-15 | Teva Pharma | NEW SYNTHESIS OF IRBESARTAN |
SI1509517T1 (en) * | 2003-01-16 | 2008-10-31 | Teva Pharma | Novel synthesis of irbesartan |
WO2004072064A1 (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 |
WO2004089938A1 (en) * | 2003-04-07 | 2004-10-21 | 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 |
DE602005025755D1 (en) | 2004-06-04 | 2011-02-17 | Teva Pharma | IRBESARTAN PHARMACEUTICAL COMPOSITION CONTAINING |
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 |
ES2454197T3 (en) * | 2004-11-11 | 2014-04-09 | Lek Pharmaceuticals D.D. | Irbesartan polymorphic forms |
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 |
ES2340701T3 (en) | 2006-01-09 | 2010-06-08 | Krka, D.D., Novo Mesto | SOLID PHARMACEUTICAL COMPOSITION UNDERSTANDING 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 |
DE602007007968D1 (en) * | 2007-11-28 | 2010-09-02 | Lesvi Laboratorios Sl | Pharmaceutical formulations with irbesartan |
US20100234614A1 (en) * | 2007-12-07 | 2010-09-16 | 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 |
US8609859B2 (en) * | 2009-04-08 | 2013-12-17 | Ctx Life Sciences Pvt. Ltd. | 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 |
WO2023052309A1 (en) | 2021-10-01 | 2023-04-06 | Sanofi | Process for preparing sartan active compounds having a tetrazole ring |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IE70593B1 (en) * | 1989-09-29 | 1996-12-11 | Eisai Co Ltd | Biphenylmethane derivative the use of it and pharmacological compositions containing same |
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 |
IL99372A0 (en) * | 1990-09-10 | 1992-08-18 | Ciba Geigy Ag | Azacyclic compounds |
-
1994
- 1994-10-19 FR FR9412459A patent/FR2725987B1/en not_active Expired - Fee Related
-
1995
- 1995-10-17 CA CA002160725A patent/CA2160725C/en not_active Expired - Fee Related
- 1995-10-17 US US08/544,027 patent/US5629331A/en not_active Expired - Lifetime
- 1995-10-17 CZ CZ19952710A patent/CZ288629B6/en not_active IP Right Cessation
- 1995-10-18 AT AT95402322T patent/ATE198478T1/en active
- 1995-10-18 RU RU95118109/04A patent/RU2144536C1/en active
- 1995-10-18 NO NO954154A patent/NO307516B1/en not_active IP Right Cessation
- 1995-10-18 CN CN95118711A patent/CN1061656C/en not_active Expired - Lifetime
- 1995-10-18 SI SI9530469T patent/SI0708103T1/en unknown
- 1995-10-18 DK DK95402322T patent/DK0708103T3/en active
- 1995-10-18 EP EP95402322A patent/EP0708103B1/en not_active Expired - Lifetime
- 1995-10-18 PL PL95311012A patent/PL184193B1/en not_active IP Right Cessation
- 1995-10-18 TW TW084110953A patent/TW357147B/en not_active IP Right Cessation
- 1995-10-18 DE DE69519788T patent/DE69519788T2/en not_active Expired - Lifetime
- 1995-10-18 PT PT95402322T patent/PT708103E/en unknown
- 1995-10-18 ES ES95402322T patent/ES2155115T3/en not_active Expired - Lifetime
- 1995-10-19 JP JP27151295A patent/JP3366786B2/en not_active Expired - Lifetime
- 1995-10-19 ZA ZA958850A patent/ZA958850B/en unknown
- 1995-10-19 HU HU9503016A patent/HU226461B1/en unknown
- 1995-10-19 KR KR1019950036285A patent/KR100251222B1/en not_active IP Right Cessation
- 1995-10-19 FI FI954992A patent/FI114156B/en not_active IP Right Cessation
- 1995-10-19 NZ NZ280293A patent/NZ280293A/en not_active IP Right Cessation
- 1995-10-19 AU AU34335/95A patent/AU698041B2/en not_active Ceased
- 1995-10-19 IL IL11568895A patent/IL115688A/en not_active IP Right Cessation
-
1998
- 1998-05-19 HK HK98104339A patent/HK1005135A1/en not_active IP Right Cessation
-
2000
- 2000-07-07 CZ CZ20002544A patent/CZ288624B6/en not_active IP Right Cessation
-
2001
- 2001-03-05 GR GR20010400343T patent/GR3035503T3/en unknown
-
2002
- 2002-05-15 CY CY0200030A patent/CY2277B1/en unknown
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |
Effective date: 20151019 |