CA1251734A - Stabilized injectable solutions of piroxicam - Google Patents
Stabilized injectable solutions of piroxicamInfo
- Publication number
- CA1251734A CA1251734A CA000492481A CA492481A CA1251734A CA 1251734 A CA1251734 A CA 1251734A CA 000492481 A CA000492481 A CA 000492481A CA 492481 A CA492481 A CA 492481A CA 1251734 A CA1251734 A CA 1251734A
- Authority
- CA
- Canada
- Prior art keywords
- piroxicam
- solution
- volume
- methylglucamine
- mole
- 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.)
- Expired
Links
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 229960002702 piroxicam Drugs 0.000 title claims abstract description 74
- 239000000243 solution Substances 0.000 claims abstract description 72
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 36
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims abstract description 33
- 239000002904 solvent Substances 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000126 substance Substances 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 7
- 229940102223 injectable solution Drugs 0.000 claims description 6
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000008363 phosphate buffer Substances 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 5
- 238000002347 injection Methods 0.000 claims 2
- 239000007924 injection Substances 0.000 claims 2
- 238000007911 parenteral administration Methods 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 235000013772 propylene glycol Nutrition 0.000 description 11
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- PGBYMPJXTSIZEC-UHFFFAOYSA-N 4-hydroxy-2-methyl-n-pyridin-2-yl-1,2-benzothiazine-3-carboxamide Chemical compound CN1SC2=CC=CC=C2C(O)=C1C(=O)NC1=CC=CC=N1 PGBYMPJXTSIZEC-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002152 aqueous-organic solution Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- -1 i.e. Chemical compound 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000003509 long acting drug Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Organic Chemistry (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Finger-Pressure Massage (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843437232 DE3437232A1 (de) | 1984-10-10 | 1984-10-10 | Stabilisierte injektionsloesungen von piroxicam |
| DEP3437232.6 | 1984-10-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1251734A true CA1251734A (en) | 1989-03-28 |
Family
ID=6247603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000492481A Expired CA1251734A (en) | 1984-10-10 | 1985-10-08 | Stabilized injectable solutions of piroxicam |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4628053A (forum.php) |
| EP (1) | EP0177870B1 (forum.php) |
| JP (1) | JPS6191116A (forum.php) |
| KR (1) | KR890001001B1 (forum.php) |
| CN (1) | CN85107838B (forum.php) |
| AT (1) | ATE62416T1 (forum.php) |
| AU (1) | AU557184B2 (forum.php) |
| CA (1) | CA1251734A (forum.php) |
| DD (1) | DD238329A5 (forum.php) |
| DE (2) | DE3437232A1 (forum.php) |
| DK (1) | DK165901C (forum.php) |
| FI (1) | FI84315C (forum.php) |
| GR (1) | GR852439B (forum.php) |
| HU (1) | HU195111B (forum.php) |
| IE (1) | IE58267B1 (forum.php) |
| IL (1) | IL76624A0 (forum.php) |
| NO (1) | NO166687C (forum.php) |
| NZ (1) | NZ213758A (forum.php) |
| PH (1) | PH23058A (forum.php) |
| PT (1) | PT81264B (forum.php) |
| SU (1) | SU1482509A3 (forum.php) |
| ZA (1) | ZA857783B (forum.php) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2545910B1 (fr) * | 1983-05-11 | 1988-07-22 | Valeo | Dispositif pour ameliorer l'efficacite d'un echangeur de chaleur dans un boitier d'une installation de climatisation, et boitier de cette installation |
| IT1196307B (it) * | 1984-10-22 | 1988-11-16 | Chiesi Farma Spa | Formulazioni farmaceutiche acquose di piroxicam monoidrato |
| US5807568A (en) * | 1994-12-27 | 1998-09-15 | Mcneil-Ppc, Inc. | Enhanced delivery of topical compositions containing flurbiprofen |
| IT1283252B1 (it) * | 1996-03-15 | 1998-04-16 | Pulitzer Italiana | Soluzioni di piroxicam iniettabili per via parenterale |
| WO1998001138A1 (fr) * | 1996-07-04 | 1998-01-15 | Nippon Kayaku Kabushiki Kaisha | Injections de succinate sodique de methylprednisolone |
| US6136799A (en) * | 1998-04-08 | 2000-10-24 | Abbott Laboratories | Cosolvent formulations |
| DE10030345A1 (de) * | 2000-06-20 | 2002-01-10 | Boehringer Ingelheim Vetmed | Hochkonzentrierte stabile Meloxicamlösungen |
| 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 |
| US8314124B2 (en) * | 2004-02-06 | 2012-11-20 | Active Biotech Ab | Crystalline salts of quinoline compounds and methods for preparing them |
| 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 |
| NZ567627A (en) * | 2005-09-30 | 2011-08-26 | Boehringer Ingelheim Vetmed | Granulation process for making a divisible tablet containing meloxicam |
| JP5832716B2 (ja) * | 2005-10-19 | 2015-12-16 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドナトリウムの結晶，及びその製造方法 |
| BRPI0713694A2 (pt) * | 2006-06-12 | 2012-10-30 | Teva Pharma | composição farmacêutica, processo para preparar composição farmacêutica, embalagens vedada, métodos para tratar um indivìduo afligido com uma forma de esclerose múltipla, e para aliviar um sintoma de esclerose múltipla em um indivìduo afligido com uma forma de esclerose múltipla, e, uso da composição farmacêutica |
| PT2682120T (pt) | 2007-12-20 | 2016-11-07 | Teva Pharma | Preparações de laquinimod estáveis |
| ES2633658T3 (es) * | 2008-09-03 | 2017-09-22 | Teva Pharmaceutical Industries Ltd. | Moduladores 2-oxo-1,2-dihidro-quinolina de la función inmunitaria |
| JP5359333B2 (ja) * | 2009-02-05 | 2013-12-04 | ゼリア新薬工業株式会社 | コロソリン酸含有水性液剤 |
| KR20160148050A (ko) * | 2009-07-30 | 2016-12-23 | 테바 파마슈티컬 인더스트리즈 리미티드 | 라퀴니모드를 이용한 크론병의 치료 |
| EP3064206B1 (en) * | 2009-08-10 | 2019-03-20 | Active Biotech AB | Treatment of huntington's disease using laquinimod |
| CN102647971B (zh) | 2009-10-12 | 2016-03-16 | 贝林格尔.英格海姆维特梅迪卡有限公司 | 用于包含美洛昔康的组合物的容器 |
| WO2011107150A1 (en) | 2010-03-03 | 2011-09-09 | Boehringer Ingelheim Vetmedica Gmbh | Use of meloxicam for the long-term treatment of musculoskeletal disorders in cats |
| US20110218191A1 (en) * | 2010-03-03 | 2011-09-08 | Boehringer Ingelheim Vetmedica Gmbh | Use of meloxicam for the long term-treatment of kidney disorders in cats |
| DE102010014290A1 (de) * | 2010-04-08 | 2011-10-13 | Hans Otto Meyer zu Spelbrink | Mittel zur prophylaktischen und therapeutischen Behandlung von Herpes-Infektionen |
| US9795568B2 (en) | 2010-05-05 | 2017-10-24 | Boehringer Ingelheim Vetmedica Gmbh | Low concentration meloxicam tablets |
| AU2012322706A1 (en) | 2011-10-12 | 2014-05-22 | Teva Pharmaceutical Industries Ltd. | Treatment of multiple sclerosis with combination of laquinimod and fingolimod |
| BR112014018485A8 (pt) | 2012-02-03 | 2017-07-11 | Teva Pharma | Uso de laquinimod para tratar pacientes com a doença de crohn que falharam com a primeira linha de terapia anti-tnf |
| TW201400117A (zh) | 2012-06-05 | 2014-01-01 | Teva Pharma | 使用拉喹莫德治療眼發炎疾病 |
| CN104955522A (zh) | 2012-11-07 | 2015-09-30 | 梯瓦制药工业有限公司 | 拉喹莫德胺盐 |
| US9233927B2 (en) | 2013-03-14 | 2016-01-12 | Teva Pharmaceutical Industries, Ltd. | Crystals of laquinimod sodium and improved process for the manufacture thereof |
| KR101749425B1 (ko) * | 2015-11-17 | 2017-06-22 | 연세대학교 산학협력단 | 난용성 약물의 서방형 제제 |
| PL3664800T3 (pl) * | 2017-08-09 | 2024-11-18 | Dechra Veterinary Products, Llc | Preparaty terapeutyczne zawierające inhibitor cox-2 i ich zastosowania |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE629650A (forum.php) * | 1967-05-18 | 1900-01-01 | ||
| US3591584A (en) * | 1968-08-27 | 1971-07-06 | Pfizer | Benzothiazine dioxides |
| DE2602363C2 (de) * | 1976-01-22 | 1984-04-12 | Bayer Ag, 5090 Leverkusen | Wäßrige, injizierbare Niclofolan- Formulierungen |
| 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 |
| DE3217315C2 (de) * | 1982-05-08 | 1986-05-22 | Gödecke AG, 1000 Berlin | Arzneimittelzubereitungen mit einem Gehalt an Oxicam-Derivaten |
| AT376879B (de) * | 1982-10-27 | 1985-01-10 | Gerot Pharmazeutika | Verfahren zur herstellung einer injektionsloesung |
-
1984
- 1984-10-10 DE DE19843437232 patent/DE3437232A1/de not_active Ceased
-
1985
- 1985-09-30 EP EP85112378A patent/EP0177870B1/de not_active Expired - Lifetime
- 1985-09-30 DE DE8585112378T patent/DE3582468D1/de not_active Expired - Fee Related
- 1985-09-30 AT AT85112378T patent/ATE62416T1/de not_active IP Right Cessation
- 1985-10-07 US US06/784,903 patent/US4628053A/en not_active Expired - Fee Related
- 1985-10-08 KR KR1019850007399A patent/KR890001001B1/ko not_active Expired
- 1985-10-08 CA CA000492481A patent/CA1251734A/en not_active Expired
- 1985-10-08 GR GR852439A patent/GR852439B/el unknown
- 1985-10-08 JP JP60224617A patent/JPS6191116A/ja active Granted
- 1985-10-08 PT PT81264A patent/PT81264B/pt not_active IP Right Cessation
- 1985-10-09 IL IL76624A patent/IL76624A0/xx not_active IP Right Cessation
- 1985-10-09 HU HU853920A patent/HU195111B/hu not_active IP Right Cessation
- 1985-10-09 DD DD85281570A patent/DD238329A5/de not_active IP Right Cessation
- 1985-10-09 AU AU48421/85A patent/AU557184B2/en not_active Ceased
- 1985-10-09 CN CN85107838A patent/CN85107838B/zh not_active Expired
- 1985-10-09 PH PH32905A patent/PH23058A/en unknown
- 1985-10-09 DK DK461385A patent/DK165901C/da not_active IP Right Cessation
- 1985-10-09 NZ NZ213758A patent/NZ213758A/xx unknown
- 1985-10-09 FI FI853926A patent/FI84315C/fi not_active IP Right Cessation
- 1985-10-09 IE IE248385A patent/IE58267B1/en not_active IP Right Cessation
- 1985-10-09 NO NO854011A patent/NO166687C/no unknown
- 1985-10-09 SU SU853966192A patent/SU1482509A3/ru active
- 1985-10-09 ZA ZA857783A patent/ZA857783B/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |