WO2004089938A1 - A novel crystalline form of irbesartan - Google Patents

A novel crystalline form of irbesartan Download PDF

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Publication number
WO2004089938A1
WO2004089938A1 PCT/IN2003/000146 IN0300146W WO2004089938A1 WO 2004089938 A1 WO2004089938 A1 WO 2004089938A1 IN 0300146 W IN0300146 W IN 0300146W WO 2004089938 A1 WO2004089938 A1 WO 2004089938A1
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Prior art keywords
irbesartan
novel crystalline
crystalline form
ray powder
powder diffraction
Prior art date
Application number
PCT/IN2003/000146
Other languages
French (fr)
Inventor
Reddy Bandi Parthasaradhi
Reddy Kura Rathnakar
Reddy Rapolu Raji
Reddy Matta Ramakrishna
Original Assignee
Hetero Drugs Limited
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 Hetero Drugs Limited filed Critical Hetero Drugs Limited
Priority to PCT/IN2003/000146 priority Critical patent/WO2004089938A1/en
Priority to AU2003242984A priority patent/AU2003242984A1/en
Publication of WO2004089938A1 publication Critical patent/WO2004089938A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/10Heterocyclic 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

Definitions

  • the present invention relates to a novel crystalline form of irbesartan, to process for its preparation and a pharmaceutical composition containing it.
  • the object of the present invention is to provide a stable novel crystalline form of irbesartan, a process for preparing it and a pharmaceutical composition containing it.
  • a novel crystalline form of irbesartan designated as form C, characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 8.3, 8.7, 10.1, 11.8, 15.0, 15.5, 16.4, 16.8, 17.5, 18.3, 19.1, 20.3, 21.1, 21.7, 23.6, 25.1, 25.5, 26.4, 26.8, 27.2, 28.1, 29.0 and 29.4 degrees.
  • Figure 1 shows typical form C x-ray powder diffraction spectrum.
  • irbesartan is mixed with a suitable solvent and irbesartan form C is isolated from the mixture.
  • a suitable solvent is heated to reflux and the contents are filtered at about 5°C to 25°C.
  • the suitable solvent is tetrahydrofuran or 1,4-dioxane; or a mixture thereof.
  • Suitable solvent mixed with any other solvent/s like water may be used as long as irbesartan form C can be isolated from the solvent mixture.
  • Previously known form of irbesartan or irbesartan prepared by a known method may be used in the process.
  • a pharmaceutical composition comprising irbesartan form C.
  • Irbesartan form C may be formulated in a form suitable for oral administration or injection.
  • Figure 1 is a x-ray powder diffraction spectrum of irbesartan form C. x-Ray powder diffraction spectrum was measured on a Siemens D5000 x- ray powder diffractometer having a copper-K ⁇ radiation.
  • Example 1 Irbesartan (5.0 gm, obtained by the process described in example 5 of US 5,270,317) is mixed with tetrahydrofuran (350 ml), heated to reflux and maintained under reflux temperature for 30 minutes. The contents are cooled to 10°C. The separated crystals are collected by filtration to give 4.2 gm irbesaratan form C.
  • Example 2 Example 1 is repeated using irbesartan form A for irbesartan to give irbesartan form C.
  • Example 3 Example 1 is repeated using irbesartan form B for irbesartan to give irbesartan form C.
  • Example 4 The mixture of Irbesartan (5.0 gm, obtained by process described in example 5 of US 5,270,317) and 1.4-dioxane (100 ml) is stirred for 5 hours at 20°C to 25°C. The solid is collected by filtration to give 4.7 gm irbesaratan form C.
  • Example 5 Irbesartan (5.0 gm, obtained by process described in example 5 of US

Abstract

The present invention relates to a novel crystalline form of irbesartan, to process for its preparation and a pharmaceutical composition containing it.

Description

A NOVEL CRYSTALLINE FORM OF IRBESARTAN
FIELD OF THE INVENTION
The present invention relates to a novel crystalline form of irbesartan, to process for its preparation and a pharmaceutical composition containing it.
BACKGROUND OF THE INVENTION
Irbesartan or 2-Butyl-3-[[2'-(1 H-tetrazol-5-yl)[1 , 1 '-biphenyl]-4-yl]methyl]-1 ,3- diazaspiro[4.4]non-1-en-4-one, which has the formula (1) :
Figure imgf000002_0001
is a powerful angiotensin II receptor antagonist.
US 5,629,331 describes two crystalline forms of irbesartan (form A, B). It has now been found that irbesartan can be prepared in a novel crystalline form (form C). The novel crystalline form is at least as stable as form A or form B and is not spontaneously converted to the previously known forms. The novel form is found to be suitable for pharmaceutical preparations.
The object of the present invention is to provide a stable novel crystalline form of irbesartan, a process for preparing it and a pharmaceutical composition containing it.
DETAILED DESCRIPTION OF THE INVENTION
According to one aspect of the present invention, there is provided a novel crystalline form of irbesartan, designated as form C, characterized by an x-ray powder diffraction pattern having peaks expressed as 2Θ at about 8.3, 8.7, 10.1, 11.8, 15.0, 15.5, 16.4, 16.8, 17.5, 18.3, 19.1, 20.3, 21.1, 21.7, 23.6, 25.1, 25.5, 26.4, 26.8, 27.2, 28.1, 29.0 and 29.4 degrees. Figure 1 shows typical form C x-ray powder diffraction spectrum.
According to another aspect of the present invention, there is provided a process for preparation of the form C of irbesartan. Thus, irbesartan is mixed with a suitable solvent and irbesartan form C is isolated from the mixture. Preferably, the mixture of irbesartan and a suitable solvent is heated to reflux and the contents are filtered at about 5°C to 25°C. The suitable solvent is tetrahydrofuran or 1,4-dioxane; or a mixture thereof. Suitable solvent mixed with any other solvent/s like water may be used as long as irbesartan form C can be isolated from the solvent mixture. Previously known form of irbesartan or irbesartan prepared by a known method may be used in the process.
According to another aspect of the present invention there is provided a pharmaceutical composition comprising irbesartan form C. Irbesartan form C may be formulated in a form suitable for oral administration or injection.
BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a x-ray powder diffraction spectrum of irbesartan form C. x-Ray powder diffraction spectrum was measured on a Siemens D5000 x- ray powder diffractometer having a copper-Kα radiation.
The following examples are given for the purpose of illustrating the present invention and should not be considered as limitations on the scope or spirit of the invention.
Example 1 Irbesartan (5.0 gm, obtained by the process described in example 5 of US 5,270,317) is mixed with tetrahydrofuran (350 ml), heated to reflux and maintained under reflux temperature for 30 minutes. The contents are cooled to 10°C. The separated crystals are collected by filtration to give 4.2 gm irbesaratan form C.
Example 2 Example 1 is repeated using irbesartan form A for irbesartan to give irbesartan form C. Example 3 Example 1 is repeated using irbesartan form B for irbesartan to give irbesartan form C.
Example 4 The mixture of Irbesartan (5.0 gm, obtained by process described in example 5 of US 5,270,317) and 1.4-dioxane (100 ml) is stirred for 5 hours at 20°C to 25°C. The solid is collected by filtration to give 4.7 gm irbesaratan form C.
Example 5 Irbesartan (5.0 gm, obtained by process described in example 5 of US
5,270,317) is added to a mixture of tetrahydrofuran (320 ml) and water (3 ml). The contents are heated to reflux, maintained under reflux temperature for 30 minutes and then cooled to 10°C. The separated crystals are collected by filtration to give 3.8 gm irbesaratan form C.

Claims

We claim:
1. A crystalline irbesartan form C, characterized by an x-ray powder diffraction pattern having peaks expressed as 2Θ at about 8.3, 8.7, 10.1, 11.8, 15.0, 15.5, 16.4, 16.8, 17.5, 18.3, 19.1 , 20.3, 21.1, 21.7, 23.6, 25.1 , 25.5, 26.4,
26.8, 27.2, 28.1 , 29.0 and 29.4 degrees.
2. A crystalline irbesartan form C of claim 1 , further characterized by an x-ray powder diffraction pattern as in figure 1.
3. A process for preparation of irbesartan form C of claim 1 , comprising the steps of: a) mixing irbesartan and tetrahydrofuran or 1 ,4-dioxane; and b) Isolating irbesartan form C from the mixture.
4. A process according to claim 3, wherein irbesartan is mixed with tetrahydrofuran.
5. A process according to claim 3, wherein irbesartan is mixed with 1 ,4- dioxane.
6. A pharmaceutical composition comprising the crystalline irbesartan form C of claim 1 and a pharmaceutically acceptable carrier.
PCT/IN2003/000146 2003-04-07 2003-04-07 A novel crystalline form of irbesartan WO2004089938A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IN2003/000146 WO2004089938A1 (en) 2003-04-07 2003-04-07 A novel crystalline form of irbesartan
AU2003242984A AU2003242984A1 (en) 2003-04-07 2003-04-07 A novel crystalline form of irbesartan

Applications Claiming Priority (1)

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WO (1) WO2004089938A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006050923A1 (en) * 2004-11-11 2006-05-18 Lek Pharmaceuticals D.D. Polymorph form of irbesartan

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0420237A1 (en) * 1989-09-29 1991-04-03 Eisai Co., Ltd. Biphenylmethane derivative, the use of it and pharmacological compositions containing same
EP0475898A1 (en) * 1990-09-10 1992-03-18 Ciba-Geigy Ag Azacyclic compounds
US5629331A (en) * 1994-10-19 1997-05-13 Sanofi Process for the preparation of a tetrazole derivative in two crystalline forms and novel the crystalline forms thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0420237A1 (en) * 1989-09-29 1991-04-03 Eisai Co., Ltd. Biphenylmethane derivative, the use of it and pharmacological compositions containing same
EP0475898A1 (en) * 1990-09-10 1992-03-18 Ciba-Geigy Ag Azacyclic compounds
US5629331A (en) * 1994-10-19 1997-05-13 Sanofi Process for the preparation of a tetrazole derivative in two crystalline forms and novel the crystalline forms thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006050923A1 (en) * 2004-11-11 2006-05-18 Lek Pharmaceuticals D.D. Polymorph form of irbesartan

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