CA2470164A1 - New crystalline forms of meloxicam and processes for their preparation and interconversion. - Google Patents
New crystalline forms of meloxicam and processes for their preparation and interconversion. Download PDFInfo
- Publication number
- CA2470164A1 CA2470164A1 CA002470164A CA2470164A CA2470164A1 CA 2470164 A1 CA2470164 A1 CA 2470164A1 CA 002470164 A CA002470164 A CA 002470164A CA 2470164 A CA2470164 A CA 2470164A CA 2470164 A1 CA2470164 A1 CA 2470164A1
- Authority
- CA
- Canada
- Prior art keywords
- meloxicam
- crystalline form
- temperature
- water
- preparing
- 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.)
- Abandoned
Links
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 title claims abstract description 157
- 229960001929 meloxicam Drugs 0.000 title claims abstract description 140
- 238000000034 method Methods 0.000 title claims abstract description 70
- 238000002360 preparation method Methods 0.000 title description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 108
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 78
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 65
- 238000010992 reflux Methods 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 35
- 238000001816 cooling Methods 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 239000002244 precipitate Substances 0.000 claims description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 28
- 239000000725 suspension Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 14
- 239000008096 xylene Substances 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- 238000001237 Raman spectrum Methods 0.000 claims description 7
- 238000002329 infrared spectrum Methods 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 claims 1
- 230000011514 reflex Effects 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 16
- 239000011521 glass Substances 0.000 description 13
- 238000010907 mechanical stirring Methods 0.000 description 13
- 239000004809 Teflon Substances 0.000 description 11
- 229920006362 Teflon® Polymers 0.000 description 11
- 230000009466 transformation Effects 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000003760 magnetic stirring Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 4
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 3
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000029087 digestion Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GUABFMPMKJGSBQ-UHFFFAOYSA-N 5-methyl-1,3-thiazol-2-amine Chemical compound CC1=CN=C(N)S1 GUABFMPMKJGSBQ-UHFFFAOYSA-N 0.000 description 2
- 102000001708 Protein Isoforms Human genes 0.000 description 2
- 108010029485 Protein Isoforms Proteins 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101000605127 Homo sapiens Prostaglandin G/H synthase 2 Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- -1 isopropyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate Chemical compound 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- ZHWSBDIYCSOTBY-UHFFFAOYSA-N propan-2-yl 4-hydroxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound C1=CC=C2S(=O)(=O)N(C)C(C(=O)OC(C)C)=C(O)C2=C1 ZHWSBDIYCSOTBY-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
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
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ESP0102743 | 2001-12-11 | ||
| ES200102743A ES2223209B1 (es) | 2001-12-11 | 2001-12-11 | Nuevas formas cristalinas del meloxicam y procedimientos para su preparacion e interconversion. |
| PCT/ES2002/000539 WO2003057692A1 (es) | 2001-12-11 | 2002-11-19 | Nuevas formas cristalinas del meloxicam y procedimientos para su preparacion e interconversion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2470164A1 true CA2470164A1 (en) | 2003-07-17 |
Family
ID=8499703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002470164A Abandoned CA2470164A1 (en) | 2001-12-11 | 2002-11-19 | New crystalline forms of meloxicam and processes for their preparation and 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) |
Families Citing this family (21)
| 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 |
| HU227359B1 (en) * | 2004-12-18 | 2011-04-28 | Egis Gyogyszergyar Nyilvanosan Mikodi Ruszvunytarsasag | Process for producing meloxicam and meloxicam potassium salt of high purity |
| 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. |
| BRPI0617208A2 (pt) * | 2005-09-30 | 2011-07-19 | Boehringer Ingelheim Vetmed | preparação farmacêutica contendo meloxicam |
| GB2443891B (en) * | 2006-11-20 | 2009-04-08 | Norbrook Lab Ltd | Process for the purification of meloxicam |
| WO2009094155A1 (en) * | 2008-01-22 | 2009-07-30 | Thar Pharmaceuticals | In vivo studies of crystalline forms of meloxicam |
| DK2488145T3 (da) * | 2009-10-12 | 2024-07-22 | Boehringer Ingelheim Vetmedica Gmbh | Beholdere til sammensætninger omfattende meloxicam |
| CA2791805A1 (en) | 2010-03-03 | 2011-09-09 | Boehringer Ingelheim Vetmedica Gmbh | 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 |
| CN109983013A (zh) * | 2016-11-18 | 2019-07-05 | 帕西拉制药有限公司 | 美洛昔康锌复合物微粒多囊脂质体制剂及其制备方法 |
| US20210322316A1 (en) * | 2016-11-18 | 2021-10-21 | Pacira Pharmaceuticals, Inc. | Zinc meloxicam complex microparticles and anesthetic formulations and processes for making the same |
| EP3958841A1 (en) | 2019-04-22 | 2022-03-02 | Mylan Specialty L.P. | Meloxicam co-crystal compositions |
| WO2022097024A1 (en) | 2020-11-06 | 2022-05-12 | 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)
| 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 |
-
2001
- 2001-12-11 ES ES200102743A patent/ES2223209B1/es not_active Expired - Fee Related
-
2002
- 2002-11-19 PL PL02370435A patent/PL370435A1/xx not_active Application Discontinuation
- 2002-11-19 KR KR1020047008796A patent/KR100919927B1/ko not_active Expired - Fee Related
- 2002-11-19 AU AU2002350753A patent/AU2002350753B2/en not_active Ceased
- 2002-11-19 HU HU0402536A patent/HUP0402536A3/hu unknown
- 2002-11-19 AT AT02785450T patent/ATE318813T1/de not_active IP Right Cessation
- 2002-11-19 NZ NZ533521A patent/NZ533521A/en not_active IP Right Cessation
- 2002-11-19 JP JP2003558007A patent/JP2005516030A/ja active Pending
- 2002-11-19 ES ES02785450T patent/ES2259725T3/es not_active Expired - Lifetime
- 2002-11-19 MX MXPA04005338A patent/MXPA04005338A/es active IP Right Grant
- 2002-11-19 CA CA002470164A patent/CA2470164A1/en not_active Abandoned
- 2002-11-19 EP EP02785450A patent/EP1462451B1/en not_active Expired - Lifetime
- 2002-11-19 PT PT02785450T patent/PT1462451E/pt unknown
- 2002-11-19 DE DE60209537T patent/DE60209537T2/de not_active Expired - Lifetime
- 2002-11-19 DK DK02785450T patent/DK1462451T3/da active
- 2002-11-19 WO PCT/ES2002/000539 patent/WO2003057692A1/es not_active Ceased
- 2002-12-09 US US10/314,542 patent/US6967248B2/en not_active Expired - Fee Related
-
2004
- 2004-06-07 ZA ZA200404475A patent/ZA200404475B/xx unknown
- 2004-07-12 NO NO20042936A patent/NO326746B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1462451A1 (en) | 2004-09-29 |
| ES2223209A1 (es) | 2005-02-16 |
| ES2259725T3 (es) | 2006-10-16 |
| NO326746B1 (no) | 2009-02-09 |
| KR100919927B1 (ko) | 2009-10-07 |
| KR20040082380A (ko) | 2004-09-24 |
| NO20042936L (no) | 2004-09-13 |
| WO2003057692A1 (es) | 2003-07-17 |
| MXPA04005338A (es) | 2005-03-31 |
| DE60209537T2 (de) | 2006-11-16 |
| DK1462451T3 (da) | 2006-06-12 |
| ZA200404475B (en) | 2005-06-07 |
| PL370435A1 (en) | 2005-05-30 |
| PT1462451E (pt) | 2006-07-31 |
| US20030109701A1 (en) | 2003-06-12 |
| ES2223209B1 (es) | 2005-10-01 |
| NZ533521A (en) | 2005-07-29 |
| ATE318813T1 (de) | 2006-03-15 |
| AU2002350753A1 (en) | 2003-07-24 |
| US6967248B2 (en) | 2005-11-22 |
| DE60209537D1 (de) | 2006-04-27 |
| HUP0402536A3 (en) | 2011-03-28 |
| HUP0402536A2 (hu) | 2005-04-28 |
| JP2005516030A (ja) | 2005-06-02 |
| AU2002350753B2 (en) | 2008-05-08 |
| EP1462451B1 (en) | 2006-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |