WO2008064615A3 - Crystalline and amorphous forms of rimonabant and processes for obtaining them - Google Patents

Crystalline and amorphous forms of rimonabant and processes for obtaining them Download PDF

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Publication number
WO2008064615A3
WO2008064615A3 PCT/CZ2007/000108 CZ2007000108W WO2008064615A3 WO 2008064615 A3 WO2008064615 A3 WO 2008064615A3 CZ 2007000108 W CZ2007000108 W CZ 2007000108W WO 2008064615 A3 WO2008064615 A3 WO 2008064615A3
Authority
WO
WIPO (PCT)
Prior art keywords
rimonabant
solvent
formula
mixture
iii
Prior art date
Application number
PCT/CZ2007/000108
Other languages
French (fr)
Other versions
WO2008064615A2 (en
Inventor
Stanislav Radl
Ludek Ridvan
Josef Cerny
Petr Hruby
Hana Petrickova
Jaroslav Havlicek
Tomas Pekarek
Original Assignee
Zentiva As
Stanislav Radl
Ludek Ridvan
Josef Cerny
Petr Hruby
Hana Petrickova
Jaroslav Havlicek
Tomas Pekarek
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
Priority claimed from CZ20060760A external-priority patent/CZ300115B6/en
Priority claimed from SK5095-2007A external-priority patent/SK50952007A3/en
Application filed by Zentiva As, Stanislav Radl, Ludek Ridvan, Josef Cerny, Petr Hruby, Hana Petrickova, Jaroslav Havlicek, Tomas Pekarek filed Critical Zentiva As
Publication of WO2008064615A2 publication Critical patent/WO2008064615A2/en
Publication of WO2008064615A3 publication Critical patent/WO2008064615A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/34—Tobacco-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addiction (AREA)
  • Psychiatry (AREA)
  • Obesity (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Novel crystalline polymorphic Form III of rimonabant and an amorphous form of rimonabant. Crystalline form III of rimonabant is prepared by dissolving rimonabant in an aprotic polar solvent such as acetonitrile or tetrahydrofuran, pouring the solution into water and stirring the resulting mixture. Amorphous form of rimonabant is prepared by dissolving in and alcohol of formula ROH, wherein R is an alkyl, such as methanol or isopropyl alcohol, and stirring the mixture. Rimonabant of formula (I) is obtained in such a way that an ester of 5-(4-chlorophenyl)-l-(2,4-dichlorophenyl)-4-methyl-lH-pyrazole-3-carboxylic acid of formula (III), wherein R is a Cl-C5 alkyl group, phenyl group or a substituted phenyl group, preferably methyl or ethyl, is reacted, in a solvent, preferably in a solvent from the group of diethyl ether, tetrahydrofuran, dioxan, dichloromethane, acetonitrile, toluene or their mixtures, or in an excess of N-aminopiperidine, with N-aminopiperidine with catalysis by at least one Lewis acid at a temperature from 0° C to the boiling point of the solvent or mixture of solvents used. Pharmaceutical compositions containing the above forms and use of the above forms for the manufacture of a medicament the treatment of obesity, for curing of the habit of smoking or for the treatment of Alzheimer or Parkinson diseases are also described.
PCT/CZ2007/000108 2006-12-01 2007-12-03 Crystalline and amorphous forms of rimonabant and processes for obtaining them WO2008064615A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CZ20060760A CZ300115B6 (en) 2006-12-01 2006-12-01 Process for preparing N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxamide (rimonabant)
CZPV2006-760 2006-12-01
SKPP5095-2007 2007-07-23
SK5095-2007A SK50952007A3 (en) 2007-07-23 2007-07-23 Crystalline polymorphic form and amorphic form of N-piperidino-5- (4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3- carboxamide (rimonabant), process for preparing them, their use, pharmaceutical composition and a drug form containing them

Publications (2)

Publication Number Publication Date
WO2008064615A2 WO2008064615A2 (en) 2008-06-05
WO2008064615A3 true WO2008064615A3 (en) 2008-10-16

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CZ2007/000108 WO2008064615A2 (en) 2006-12-01 2007-12-03 Crystalline and amorphous forms of rimonabant and processes for obtaining them

Country Status (1)

Country Link
WO (1) WO2008064615A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008056377A2 (en) * 2006-11-06 2008-05-15 Cadila Healthcare Limited Polymorphic forms of rimonabant

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0656354A1 (en) * 1993-12-02 1995-06-07 Sanofi Substituted N-piperidino 3-pyrazolecarboxamide
WO2003040105A1 (en) * 2001-11-08 2003-05-15 Sanofi-Synthelabo Polymorphous form of rimonabant, preparation method and pharmaceutical compositions containing same
EP1816125A1 (en) * 2006-02-02 2007-08-08 Ranbaxy Laboratories, Ltd. Novel crystalline forms of an antagonist of CB1 cannabinoid receptor and preparation method thereof
WO2007103711A2 (en) * 2006-03-01 2007-09-13 Dr. Reddy's Laboratories Ltd. Polymorphic forms of rimonabant
WO2007121466A2 (en) * 2006-04-18 2007-10-25 Dr. Reddy's Laboratories Ltd. Process for preparing rimonabant
WO2008026219A2 (en) * 2006-09-01 2008-03-06 Hetero Drugs Limited Novel polymorphs of rimonabant
WO2008035023A1 (en) * 2006-09-19 2008-03-27 Cipla Limited Polymorphs of rimonabant
WO2008038143A2 (en) * 2006-06-22 2008-04-03 Medichem, S.A. Novel solid forms of rimonabant and synthetic processes for their preparation
WO2008081009A2 (en) * 2007-01-05 2008-07-10 Synthon B.V. Amorphous rimonabant and rimonabant solvates and processes for their preparation
EP1944297A1 (en) * 2007-01-09 2008-07-16 Miklós Vértessy Solid and crystalline rimonabant and processes for preparation, and pharmaceutical composition thereof

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0656354A1 (en) * 1993-12-02 1995-06-07 Sanofi Substituted N-piperidino 3-pyrazolecarboxamide
WO2003040105A1 (en) * 2001-11-08 2003-05-15 Sanofi-Synthelabo Polymorphous form of rimonabant, preparation method and pharmaceutical compositions containing same
EP1816125A1 (en) * 2006-02-02 2007-08-08 Ranbaxy Laboratories, Ltd. Novel crystalline forms of an antagonist of CB1 cannabinoid receptor and preparation method thereof
WO2007103711A2 (en) * 2006-03-01 2007-09-13 Dr. Reddy's Laboratories Ltd. Polymorphic forms of rimonabant
WO2007121466A2 (en) * 2006-04-18 2007-10-25 Dr. Reddy's Laboratories Ltd. Process for preparing rimonabant
WO2008038143A2 (en) * 2006-06-22 2008-04-03 Medichem, S.A. Novel solid forms of rimonabant and synthetic processes for their preparation
WO2008026219A2 (en) * 2006-09-01 2008-03-06 Hetero Drugs Limited Novel polymorphs of rimonabant
WO2008035023A1 (en) * 2006-09-19 2008-03-27 Cipla Limited Polymorphs of rimonabant
WO2008081009A2 (en) * 2007-01-05 2008-07-10 Synthon B.V. Amorphous rimonabant and rimonabant solvates and processes for their preparation
EP1944297A1 (en) * 2007-01-09 2008-07-16 Miklós Vértessy Solid and crystalline rimonabant and processes for preparation, and pharmaceutical composition thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BRITAIN ET AL: "Polymorphism in Pharmaceutical Solids passage", POLYMORPHISM IN PHARMACEUTICAL SOLIDS, 1999, pages 235 - 238, XP002278123 *
CAIRA M R: "CRYSTALLINE POLYMORPHISM OF ORGANIC COMPOUNDS", TOPICS IN CURRENT CHEMISTRY, SPRINGER, BERLIN, DE, vol. 198, 1998, pages 163 - 208, XP001156954, ISSN: 0340-1022 *

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Publication number Publication date
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