WO2003057692A1 - Nuevas formas cristalinas del meloxicam y procedimientos para su preparacion e interconversion - Google Patents

Nuevas formas cristalinas del meloxicam y procedimientos para su preparacion e interconversion Download PDF

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Publication number
WO2003057692A1
WO2003057692A1 PCT/ES2002/000539 ES0200539W WO03057692A1 WO 2003057692 A1 WO2003057692 A1 WO 2003057692A1 ES 0200539 W ES0200539 W ES 0200539W WO 03057692 A1 WO03057692 A1 WO 03057692A1
Authority
WO
WIPO (PCT)
Prior art keywords
meloxicam
crystalline form
temperature
water
preparation
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.)
Ceased
Application number
PCT/ES2002/000539
Other languages
English (en)
Spanish (es)
French (fr)
Inventor
Laura Coppi
Martí Bartra Sanmarti
Montserrat Closa Calvo
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.)
Esteve Quimica SA
Original Assignee
Esteve Quimica 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
Priority to KR1020047008796A priority Critical patent/KR100919927B1/ko
Priority to HU0402536A priority patent/HUP0402536A3/hu
Priority to AU2002350753A priority patent/AU2002350753B2/en
Priority to JP2003558007A priority patent/JP2005516030A/ja
Priority to EP02785450A priority patent/EP1462451B1/en
Priority to SI200230288T priority patent/SI1462451T1/sl
Priority to CA002470164A priority patent/CA2470164A1/en
Priority to MXPA04005338A priority patent/MXPA04005338A/es
Application filed by Esteve Quimica SA filed Critical Esteve Quimica SA
Priority to NZ533521A priority patent/NZ533521A/en
Priority to DE60209537T priority patent/DE60209537T2/de
Publication of WO2003057692A1 publication Critical patent/WO2003057692A1/es
Anticipated expiration legal-status Critical
Priority to NO20042630A priority patent/NO20042630L/no
Priority to NO20042936A priority patent/NO326746B1/no
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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

Definitions

  • the present invention relates to the crystalline forms of meloxicam and to methods for its preparation and interconversion. More specifically, it refers to the new crystalline forms II, III and V of meloxicam; to the processes for obtaining said new crystalline forms II, III and V; and, finally, to the processes of interconversion of forms II, III, IV and V in form I.
  • meloxicam is obtained by reacting 4-hydroxy-2-methyl-2H-1, 2- benzothiazine-3-carboxylate of isopropyl 1,1-dioxide (or other carboxylic acid derivatives) and 2 -amino-5- methyl thiazole in xylene at reflux with partial distillation.
  • the meloxicam thus obtained, so that it is of an adequate quality, has to be purified.
  • This purification is carried out by crystallization in organic solvents such as dichloroethane or 1,2-dichlorobenzene (see DE 2756113).
  • meloxicam is understood as the crude product obtained in any of the preparation reactions of said compound known in the state of the art; for example, by the reaction of 4-hydroxy-2-methyl-2H-l, 2-benzothiazine-3-carboxylate of isopropyl 1,1-dioxide (or other carboxylic acid derivatives) and 2-amino-5-methylthiazole in Xylene at reflux with partial distillation.
  • the meloxicam is dissolved in a mixture composed of water, NaOH and an organic solvent selected from: an alcohol, such as ethanol, xylene, toluene and dimethylformamide (DMF), and at a temperature that is maintained during the 50 ° C process at reflux temperature.
  • an organic solvent selected from: an alcohol, such as ethanol, xylene, toluene and dimethylformamide (DMF)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Cosmetics (AREA)
PCT/ES2002/000539 2001-12-11 2002-11-19 Nuevas formas cristalinas del meloxicam y procedimientos para su preparacion e interconversion Ceased WO2003057692A1 (es)

Priority Applications (12)

Application Number Priority Date Filing Date Title
CA002470164A CA2470164A1 (en) 2001-12-11 2002-11-19 New crystalline forms of meloxicam and processes for their preparation and interconversion.
AU2002350753A AU2002350753B2 (en) 2001-12-11 2002-11-19 Novel crystalline forms of meloxicam and the preparation and interconversion methods thereof
JP2003558007A JP2005516030A (ja) 2001-12-11 2002-11-19 新規な結晶性の形態のメロキシカム並びにそれらの製造及び相互転換方法
EP02785450A EP1462451B1 (en) 2001-12-11 2002-11-19 Novel crystalline forms of meloxicam and the preparation and interconversion methods thereof
SI200230288T SI1462451T1 (sl) 2001-12-11 2002-11-19 Nove kristalne oblike meloksikama in priprava in medsebojno zamenljivi postopki pri le-teh
MXPA04005338A MXPA04005338A (es) 2001-12-11 2002-11-19 Nuevas formas cristalinas del meloxicam y procedimientos para su preparacion e interconversion.
NZ533521A NZ533521A (en) 2001-12-11 2002-11-19 New crystalline forms of meloxicam and processes for their preparation and interconversion
KR1020047008796A KR100919927B1 (ko) 2001-12-11 2002-11-19 멜록시캄의 신규한 결정형 그리고 그들의 제조 및상호전환 방법
HU0402536A HUP0402536A3 (en) 2001-12-11 2002-11-19 Novel crystalline forms of meloxicam and the preparation and interconversion methods thereof
DE60209537T DE60209537T2 (de) 2001-12-11 2002-11-19 Neue kristalline formen von meloxicam, deren herstellung und verfahren zu deren umwandlung ineinander
NO20042630A NO20042630L (no) 2001-12-18 2004-06-23 Tablettert, oral, enterisk belagt, farmasoytisk doseringsform inneholdende en syrelabil benzimidazol
NO20042936A NO326746B1 (no) 2001-12-11 2004-07-12 Nye krystallinske former av meloksikam og fremgangsmater for deres fremstilling og interkonversjon

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES200102743A ES2223209B1 (es) 2001-12-11 2001-12-11 Nuevas formas cristalinas del meloxicam y procedimientos para su preparacion e interconversion.
ESP0102743 2001-12-11

Publications (1)

Publication Number Publication Date
WO2003057692A1 true WO2003057692A1 (es) 2003-07-17

Family

ID=8499703

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/ES2002/000539 Ceased WO2003057692A1 (es) 2001-12-11 2002-11-19 Nuevas formas cristalinas del meloxicam y procedimientos para su preparacion e interconversion

Country Status (18)

Country Link
US (1) US6967248B2 (enExample)
EP (1) EP1462451B1 (enExample)
JP (1) JP2005516030A (enExample)
KR (1) KR100919927B1 (enExample)
AT (1) ATE318813T1 (enExample)
AU (1) AU2002350753B2 (enExample)
CA (1) CA2470164A1 (enExample)
DE (1) DE60209537T2 (enExample)
DK (1) DK1462451T3 (enExample)
ES (2) ES2223209B1 (enExample)
HU (1) HUP0402536A3 (enExample)
MX (1) MXPA04005338A (enExample)
NO (1) NO326746B1 (enExample)
NZ (1) NZ533521A (enExample)
PL (1) PL370435A1 (enExample)
PT (1) PT1462451E (enExample)
WO (1) WO2003057692A1 (enExample)
ZA (1) ZA200404475B (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008524197A (ja) * 2004-12-18 2008-07-10 エギシュ ヂョヂセルヂャール エンニュ・エル・テー 高純度メロキシカム及びメロキシカムカリウム塩の製法

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020035107A1 (en) 2000-06-20 2002-03-21 Stefan Henke Highly concentrated stable meloxicam solutions
DE10161077A1 (de) 2001-12-12 2003-06-18 Boehringer Ingelheim Vetmed Hochkonzentrierte stabile Meloxicamlösungen zur nadellosen Injektion
US8992980B2 (en) 2002-10-25 2015-03-31 Boehringer Ingelheim Vetmedica Gmbh Water-soluble meloxicam granules
EP1568369A1 (en) 2004-02-23 2005-08-31 Boehringer Ingelheim Vetmedica Gmbh Use of meloxicam for the treatment of respiratory diseases in pigs
DE102004021281A1 (de) * 2004-04-29 2005-11-24 Boehringer Ingelheim Vetmedica Gmbh Verwendung von Meloxicam-Formulierungen in der Veterinärmedizin
DE102004030409A1 (de) * 2004-06-23 2006-01-26 Boehringer Ingelheim Vetmedica Gmbh Neue Verwendung von Meloxicam in der Veterinärmedizin
ITMI20041918A1 (it) 2004-10-11 2005-01-11 A M S A Anonima Materie Sintetiche Affini Spa Processo di purificazione di meloxicam
FR2889847B1 (fr) 2005-08-18 2007-10-05 Sanofi Aventis Sa Derives de 5-pyridazinyl-1-azabicyclo[3.2.1]octave, leur preparation en therapeutique.
SG166115A1 (en) * 2005-09-30 2010-11-29 Boehringer Ingelheim Vetmed Pharmaceutical preparation containing meloxicam
GB2443891B (en) * 2006-11-20 2009-04-08 Norbrook Lab Ltd Process for the purification of meloxicam
EP2244712B1 (en) * 2008-01-22 2015-08-05 Thar Pharmaceuticals Inc. In vivo studies of crystalline forms of meloxicam
EP2488145B1 (en) * 2009-10-12 2024-04-24 Boehringer Ingelheim Vetmedica GmbH Containers for compositions comprising meloxicam
SG183846A1 (en) 2010-03-03 2012-10-30 Boehringer Ingelheim Vetmed Use of meloxicam for the long-term treatment of musculoskeletal disorders in cats
US9795568B2 (en) 2010-05-05 2017-10-24 Boehringer Ingelheim Vetmedica Gmbh Low concentration meloxicam tablets
CN103772378B (zh) * 2014-01-26 2016-02-24 悦康药业集团有限公司 一种美洛昔康化合物及其片剂
US20210322316A1 (en) * 2016-11-18 2021-10-21 Pacira Pharmaceuticals, Inc. Zinc meloxicam complex microparticles and anesthetic formulations and processes for making the same
EP3541815A4 (en) * 2016-11-18 2020-07-15 Pacira Pharmaceuticals, Inc. ZINC MELXICAM COMPLEX MICROPARTICLE MULTIVESICULAR LIPOSOME FORMULATIONS AND METHODS OF MAKING THE SAME
US20220184095A1 (en) 2019-04-22 2022-06-16 Mylan Specialty L.P. Meloxicam co-crystal compositions
AU2021375409A1 (en) 2020-11-06 2023-06-29 Mylan Laboratories Ltd Pharmaceutical composition comprising meloxicam
CN116421567B (zh) * 2023-04-27 2025-02-07 浙江萃泽医药科技有限公司 一种稳定冻干制剂及其制备方法和应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2756113A1 (de) * 1977-12-16 1979-06-21 Thomae Gmbh Dr K Neue 4-hydroxy-2h-1,2-benzothiazin- 3-carboxamid-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
US6355666B1 (en) * 2000-06-23 2002-03-12 Medinox, Inc. Protected forms of pharmacologically active agents and uses therefor

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LUGER P. ET AL: "Structure and physicochemical properties of meloxicam, a new NSAID", EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 4, no. 3, 1996, AMSTERDAM, NL, pages 175 - 187, XP002074736 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008524197A (ja) * 2004-12-18 2008-07-10 エギシュ ヂョヂセルヂャール エンニュ・エル・テー 高純度メロキシカム及びメロキシカムカリウム塩の製法

Also Published As

Publication number Publication date
NZ533521A (en) 2005-07-29
DK1462451T3 (da) 2006-06-12
ES2223209B1 (es) 2005-10-01
JP2005516030A (ja) 2005-06-02
PL370435A1 (en) 2005-05-30
EP1462451B1 (en) 2006-03-01
KR100919927B1 (ko) 2009-10-07
PT1462451E (pt) 2006-07-31
EP1462451A1 (en) 2004-09-29
NO326746B1 (no) 2009-02-09
DE60209537D1 (de) 2006-04-27
CA2470164A1 (en) 2003-07-17
US6967248B2 (en) 2005-11-22
US20030109701A1 (en) 2003-06-12
MXPA04005338A (es) 2005-03-31
ATE318813T1 (de) 2006-03-15
DE60209537T2 (de) 2006-11-16
HUP0402536A2 (hu) 2005-04-28
ZA200404475B (en) 2005-06-07
NO20042936L (no) 2004-09-13
KR20040082380A (ko) 2004-09-24
AU2002350753B2 (en) 2008-05-08
AU2002350753A1 (en) 2003-07-24
ES2223209A1 (es) 2005-02-16
HUP0402536A3 (en) 2011-03-28
ES2259725T3 (es) 2006-10-16

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