WO2008062274A2 - Pharmaceutical formulations of nsaids for parentral use - Google Patents
Pharmaceutical formulations of nsaids for parentral use Download PDFInfo
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- WO2008062274A2 WO2008062274A2 PCT/IB2007/003515 IB2007003515W WO2008062274A2 WO 2008062274 A2 WO2008062274 A2 WO 2008062274A2 IB 2007003515 W IB2007003515 W IB 2007003515W WO 2008062274 A2 WO2008062274 A2 WO 2008062274A2
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- WO
- WIPO (PCT)
- Prior art keywords
- meloxicam
- solution
- pharmaceutical composition
- concentration
- pyrrolidone
- Prior art date
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Classifications
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- 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
- A61K31/549—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 having two or more nitrogen atoms in the same ring, e.g. hydrochlorothiazide
-
- 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
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
Definitions
- the invention relates to novel stable formulations comprising non- steroidal antiinflammatory drug (NSAIDs), as injectables.
- NSAIDs non- steroidal antiinflammatory drug
- the object of present invention is to provide a clear and stable solution of NSAIDs such as meloxicam as injectables without incorporation of any additives.
- Nonsteroidal anti-inflammatory drugs as a therapeutic class, exhibit analgesic, anti-inflammatory, antipyretic, and platelet inhibitory properties.
- these drugs have side effects such as gastrointestinal (GI) toxicities, gastric mucosal ulcerations and hemorrhage due to inhibition of prostaglandin production.
- GI gastrointestinal
- the mechanism of action of NSAIDs has been attributed to their ability to inhibit the cyclooxygenase enzyme (cox).
- cox-1 is responsible for mediating the production of prostaglandin while cox-2 is primarily associated with inflammation, pain, and fever.
- the traditional NSAIDs are nonselective cox inhibitors.
- Cox-2 selective NSAIDs are, therefore, ideal anti-inflammatory drugs with minimum drug-related side effects, since they spare cox-1 activity.
- Meloxicam which belong to the class of NSAIDs is used for pain related symptoms in both humans and animals.
- Meloxicam is practically insoluble in water.
- Meloxicam can be graded in Class II, of the Biopharmaceutical Classification System, which means low aqueous solubility and rapid absorption (high permeability) through the gastrointestinal tract Poor solubility and wettability of meloxicam, causes problems in preparation of pharmaceutical formulations, to be administered by the parenteral route.
- the use of cosolvents has been employed by several workers to solubilize meloxicam.
- EP-A-O 945 134 discloses pH dependent solubility characteristics of meloxicam and its salts, such as sodium salt, ammonium salts, and meglumine salts, in the aqueous solution.
- WO 2005/105101 discloses formulations containing aqueous solutions of meloxicam or meloxicam salt in concentration of 0.1 to 50 mg/ml.
- additives include pH adjusters, solubilizers, gelling agents, viscosity enhancers, preservatives, oils, antioxidants, emulsifiers, foam-forming agent etc.
- meloxicam as such has been soluble to produce clear stable parenteral soluf ' standing need of the industry to provide clear and stable products in which only meloxicam has been solubilized.
- the present invention provides clear stable novel formulations comprising of nonsteroidal anti-inflammatory drug (NSAIDs), for the parenteral use.
- the non-steroidal antiinflammatory drag (NSAIDs) used for present invention is meloxicam or its salt, in diverse therapeutically recommended strengths.
- NSAIDs nonsteroidal antiinflammatory drag
- meloxicam as such and meloxicam with its salts were utilized for the purpose of formulation.
- the objective of the present invention is to prepare clear and stable solution of NSAIDs such as meloxicam or its salt for parenteral use without incorporation of any additive in solution.
- the solution used in the present invention comprise of solvent selected from the family of 2-pyrrolidone such as N-Methyl 2-Pyrrolidone , 2 Pyrrolidone and mixture thereof , along with ethanol and optional use of water for injection.
- Ethanol used in the fo ⁇ nulation acts as a co solvent and or preservative.
- meloxicam has very poor aqueous solubility, wettability and hence the uses of the meloxicam salts become inevitable if one has to prepare a clear aqueous solution or injection. It is also reported that if meloxicam has to use for the preparation of injection, then oil base vehicle system is required along with certain additives like solubilizer or emulsifier or others.
- the present invention is based on preparation of meloxicam injection without any additives, without any additives means it doses not includes additives such as gelling agent, viscosity enhancers, oils antioxidants, emulsif ⁇ ers, foam- forming agents, buffer etc.
- concentration of the meloxicam or its salts used in the present invention is in the range of 0.1 mg/ml to 50 mg/ml.
- the Injectable composition of meloxicam or its salts contains solvent system with optional use of salt forming agent. Though the salt forming agents are essentially not required for the present formulations, they may optionally add in the formulation in molar ration ranging from 0.00 lto 0.9 moles.
- the present invention contains formulation of meloxicam and meloxicam salt; the meloxicam salt mentions here are sodium salt, ammonium salt and meglumine salt etc.
- solvent system selected in such a way that it provides clear and stable solution for meloxicam and or meloxicam salts, such as mention above.
- the related substances mention in the meloxicam monograph is a crucial factor to determine the stability of the present formulations.
- compositions were carried out for meloxicam with change in concentration of the N-Methyl 2-prrolidone (NMP) and ethanol in vehicle system.
- NMP N-Methyl 2-prrolidone
- the various compositions were also carried out for meloxicam injection to optimize use of the other solvent of the 2-pyrrolidone group such as 2-pyrrolidone (2-P).
- the concentration of meloxicam as such, in compositions with NMP in present invention is ranging from about 1 mg / ml to about 25 mg /ml solution, preferably about 1 mg / ml to about 22 mg /ml solution more preferably of about 5 mg / ml to about 25 mg /ml.
- the concentration of meloxicam with its salts in compositions with NMP in present invention is ranging from about lmg/ml to about 50 mg /ml in solution with out use of any additives as mention above.
- NMP N-Methyl 2-prrolidone
- NMP N-Methyl 2-prrolidone
- the concentration of meloxicam as such, in compositions with 2-pyrrolidone is ranging from about 1 mg/ml to about 6.5 mg/ml, preferably about 5 mg/ml to about 6.5 mg/ml in solution.
- the concentration of meloxicam with its salts in compositions with 2- Pyrrolidone is ranging from about 1 mg/ml to about 50 mg/ml.
- the concentration of 2-prrolidone in composition mention above is in the range of about 55 to about 80 % preferably about 55 to about 70% and ethanol concentration in the range of about 10 to about 25 % preferably about 10 to about 20%, water for injection added to sufficient to produce 100% volume.
- the concentration of 2-prrolidone in above composition is in the range of about 20to about 80 % preferably about 20 to about 50% and ethanol concentration in the range of about 5 to about 25 % preferably about 10 to about 20%, water for injection added to sufficient to produce 100% volume wherein the solution contains inorganic acid or base and Meloxicam in a molar ratio of between 0.01: 1 and 0.9:1.
- Meloxicam contains chemically a amide linkage in between, as a result of hydrolysis of amide linkage leads to formation of impurity B in the final formulation when pH >8-9. It is observed that formulation of meloxicam with alkaline salt, mostly sodium or potassium etc has pH range 6.5-9, preferably 8.5-9, has impurity B as a major impurity. Thus it is necessary that meloxicam injection produced without the alkaline salt will have preference. Thus composition prepared in the present invention, it is possible to prepare meloxicam injection in concentration range 1 mg/ml to 22mg/ml, with out use of salt forming agent of meloxicam, such as Sodium or potassium etc., in aqueous solution with out incorporation of additive
- compositions of drug product prepared using meloxicam as such and meloxicam with its salt are provided with % composition of components being provided in table two and three:
- Table 2 comparative formulations of Meloxicam injection strength: 2% Meloxicam
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- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Abstract
The novel stable pharmaceutical composition comprising non-steroidal anti inflammatory drug (NSAIDs), as injectables, which provides a clear and stable pharmaceutical composition without incorporation of any additives.
Description
PHARMACEUTICAL FORMULATIONS OF NSAIDs FOR PARENTRAL USE.
FIELD OF THE INVENTION
The invention relates to novel stable formulations comprising non- steroidal antiinflammatory drug (NSAIDs), as injectables. The object of present invention is to provide a clear and stable solution of NSAIDs such as meloxicam as injectables without incorporation of any additives.
BACKGROUND OF THE INVENTION:
Nonsteroidal anti-inflammatory drugs (NSAIDs) as a therapeutic class, exhibit analgesic, anti-inflammatory, antipyretic, and platelet inhibitory properties. However, these drugs have side effects such as gastrointestinal (GI) toxicities, gastric mucosal ulcerations and hemorrhage due to inhibition of prostaglandin production. The mechanism of action of NSAIDs has been attributed to their ability to inhibit the cyclooxygenase enzyme (cox). Out of the 2 isoforms of cyclooxygenase, cox-1 is responsible for mediating the production of prostaglandin while cox-2 is primarily associated with inflammation, pain, and fever. The traditional NSAIDs are nonselective cox inhibitors. Cox-2 selective NSAIDs are, therefore, ideal anti-inflammatory drugs with minimum drug-related side effects, since they spare cox-1 activity. Meloxicam which belong to the class of NSAIDs is used for pain related symptoms in both humans and animals.
Like many other NSAIDs, Meloxicam is practically insoluble in water. Meloxicam can be graded in Class II, of the Biopharmaceutical Classification System, which means low aqueous solubility and rapid absorption (high permeability) through the gastrointestinal tract Poor solubility and wettability of meloxicam, causes problems in preparation of pharmaceutical formulations, to be administered by the parenteral route. The use of cosolvents has been employed by several workers to solubilize meloxicam. EP-A-O 945 134 discloses pH dependent solubility characteristics of meloxicam and its salts, such as sodium salt, ammonium salts, and meglumine salts, in the aqueous solution. WO 2005/105101 discloses formulations containing aqueous solutions of meloxicam or meloxicam salt in concentration of 0.1 to 50 mg/ml. To stabilize the formulation it is essential to include additives include pH adjusters, solubilizers, gelling agents, viscosity enhancers, preservatives, oils, antioxidants, emulsifiers, foam-forming agent etc. Surprisingly, it has been possible to produce stable clear aqueous solution of meloxicam salts only. There is no report in which meloxicam as such has been soluble to produce clear stable parenteral soluf '
standing need of the industry to provide clear and stable products in which only meloxicam has been solubilized.
DETAILED DESCRIPTION OF THE INVENTION:
The present invention provides clear stable novel formulations comprising of nonsteroidal anti-inflammatory drug (NSAIDs), for the parenteral use. The non-steroidal antiinflammatory drag (NSAIDs) used for present invention is meloxicam or its salt, in diverse therapeutically recommended strengths. During the course of present study, meloxicam as such and meloxicam with its salts were utilized for the purpose of formulation. The objective of the present invention is to prepare clear and stable solution of NSAIDs such as meloxicam or its salt for parenteral use without incorporation of any additive in solution. The solution used in the present invention comprise of solvent selected from the family of 2-pyrrolidone such as N-Methyl 2-Pyrrolidone , 2 Pyrrolidone and mixture thereof , along with ethanol and optional use of water for injection. Ethanol used in the foπnulation acts as a co solvent and or preservative. In prior art it is reported that meloxicam has very poor aqueous solubility, wettability and hence the uses of the meloxicam salts become inevitable if one has to prepare a clear aqueous solution or injection. It is also reported that if meloxicam has to use for the preparation of injection, then oil base vehicle system is required along with certain additives like solubilizer or emulsifier or others. The present invention is based on preparation of meloxicam injection without any additives, without any additives means it doses not includes additives such as gelling agent, viscosity enhancers, oils antioxidants, emulsifϊers, foam- forming agents, buffer etc. The concentration of the meloxicam or its salts used in the present invention is in the range of 0.1 mg/ml to 50 mg/ml. The Injectable composition of meloxicam or its salts contains solvent system with optional use of salt forming agent. Though the salt forming agents are essentially not required for the present formulations, they may optionally add in the formulation in molar ration ranging from 0.00 lto 0.9 moles. The present invention contains formulation of meloxicam and meloxicam salt; the meloxicam salt mentions here are sodium salt, ammonium salt and meglumine salt etc. In present invention solvent system selected in such a way that it provides clear and stable solution for meloxicam and or meloxicam salts, such as mention above. The related substances mention in the meloxicam monograph is a crucial factor to determine the stability of the present formulations.
The various compositions were carried out for meloxicam with change in concentration of the N-Methyl 2-prrolidone (NMP) and ethanol in vehicle system. The
various compositions were also carried out for meloxicam injection to optimize use of the other solvent of the 2-pyrrolidone group such as 2-pyrrolidone (2-P).
Table: 1: The typical composition used is cited below:
The concentration of meloxicam as such, in compositions with NMP in present invention is ranging from about 1 mg / ml to about 25 mg /ml solution, preferably about 1 mg / ml to about 22 mg /ml solution more preferably of about 5 mg / ml to about 25 mg /ml. The concentration of meloxicam with its salts in compositions with NMP in present invention is ranging from about lmg/ml to about 50 mg /ml in solution with out use of any additives as mention above. The concentration of N-Methyl 2-prrolidone (NMP) in composition for meloxicam as such is in the range of about 50 % to about 80 % preferably about 55 % to about 70 % and ethanol concentration in the range of about 10 % to about 20 % preferably in about 10 % to about 20%, water for injection added to sufficient to produce 100% volume. For meloxicam with its salt the concentration of N-Methyl 2-prrolidone (NMP) for above compositions is in the range of about 20 % to about 80 % preferably about 20 % to about 50 % and ethanol concentration in the range of about 5 % to about 25 % preferably in about 10 % to about 20 % water for injection added to sufficient to produce 100% volume wherein the solution contains inorganic acid or base and Meloxicam in a molar ratio of between 0.01:1 and 0.9:1
This variation in the concentration of NMP and Ethanol in composition mention above, gives clear, stable solution of the meloxicam and or its salt in presence of the water for injection at various concentration of meloxicam ranging from 0.1- 50 mg /ml in solution.
The concentration of meloxicam as such, in compositions with 2-pyrrolidone is ranging from about 1 mg/ml to about 6.5 mg/ml, preferably about 5 mg/ml to about 6.5 mg/ml in solution. The concentration of meloxicam with its salts in compositions with 2- Pyrrolidone is ranging from about 1 mg/ml to about 50 mg/ml. For meloxicam as such, the
concentration of 2-prrolidone in composition mention above is in the range of about 55 to about 80 % preferably about 55 to about 70% and ethanol concentration in the range of about 10 to about 25 % preferably about 10 to about 20%, water for injection added to sufficient to produce 100% volume. For meloxicam with its salt the concentration of 2-prrolidone in above composition is in the range of about 20to about 80 % preferably about 20 to about 50% and ethanol concentration in the range of about 5 to about 25 % preferably about 10 to about 20%, water for injection added to sufficient to produce 100% volume wherein the solution contains inorganic acid or base and Meloxicam in a molar ratio of between 0.01: 1 and 0.9:1.
Meloxicam contains chemically a amide linkage in between, as a result of hydrolysis of amide linkage leads to formation of impurity B in the final formulation when pH >8-9. It is observed that formulation of meloxicam with alkaline salt, mostly sodium or potassium etc has pH range 6.5-9, preferably 8.5-9, has impurity B as a major impurity. Thus it is necessary that meloxicam injection produced without the alkaline salt will have preference. Thus composition prepared in the present invention, it is possible to prepare meloxicam injection in concentration range 1 mg/ml to 22mg/ml, with out use of salt forming agent of meloxicam, such as Sodium or potassium etc., in aqueous solution with out incorporation of additive
This variation in the concentration of solvent and Ethanol in composition mention above, gives clear, stable solution of the meloxicam and or its salt in presence of the water for injection at various concentration of meloxicam ranging from 0.1- 50 mg /ml solution.
The preferred compositions of drug product prepared using meloxicam as such and meloxicam with its salt are provided with % composition of components being provided in table two and three:
Table 2 : comparative formulations of Meloxicam injection strength: 2% Meloxicam
Table 3: comparative formulations of Meloxicam injection Strength: 0.5% Meloxicam
* Water for injection
The stable pharmaceutical compositions described above is obtained through following non-limiting examples.
Example 1 :
Preparation of 0.5 % solution of meloxicam with N- methyl 2-Pyrollidone
Dissolve 5 g meloxicam in 0.54 liters of N- methyl 2-Pyrollidone and stir till a clear solution is formed. Add 0.14 liters of ethyl alcohol to the solution and stir for 5 min. Adjust pH with 5 % Sodium hydroxide up to 8.8. Make up the required volume up to one liter with WFI and filter through 0.22-micron nylon filter, sealed and packed in sterilized vials.
Example 2 :
Preparation of 2 % solution of meloxicam with N- methyl 2-Pyrollidone
Dissolve 20 g meloxicam in 0.700 liters of N- methyl Pyrollidone and stir till a clear solution is formed. Add 0.200 liters of alcohol to the solution and stir for 5 min. Adjust pH with 5 % Sodium hydroxide up to 8.8. Make up the required volume up to
one liter with WFI and filter through 0.22-micron nylon filter, sealed and packed in sterilized vials.
Example 3 :
Preparation of 0.5 % solution of meloxicam with N- methyl 2-PyroIlidone with out additives
Dissolve 5 g meloxicam in 0.54 liters of N- methyl 2-Pyrollidone and stir till a clear solution is formed. Add 0.14 liters of ethyl alcohol to the solution and stir for 5 min. make up the required volume up to one liter with WFI and filter through 0.22-micron nylon filter, sealed and packed in sterilized vials.
Example 4 :
Preparation of 2 % solution of meloxicam with N- methyl 2-Pyrollidone with out additives
Dissolve 20 g meloxicam in 0.700 liters of N- methyl Pyrollidone and stir till a clear solution is formed. Add 0.200 liters of alcohol to the solution and stir for 5 min. Make up the required volume up to one liter with WFI and filter through 0.22-micron nylon filter, sealed and packed in sterilized vials.
Example 5 :
Preparation of 0.5 % solution of meloxicam with 2-Pyrollidone
Dissolve 5 g meloxicam in 0.54 liters of 2-Pyrollidone and stir till a clear solution is formed. Add 0.14 liters of ethyl alcohol to the solution and stir for 5 min. Adjust pH with 5 % Sodium hydroxide up to 8.8. Make up the required volume up to one liter with WFI and filter through 0.22-micron nylon filter, sealed and packed in sterilized vials.
Example 6 :
Preparation of 2 % solution of meloxicam with 2-Pyrollidone
Dissolve 20 g meloxicam in 0.700 liters of 2- Pyrollidone and stir till a clear solution is formed. Add 0.200 liters of alcohol to the solution and stir for 5 min. Adjust pH with 5 % Sodium hydroxide up to 8.8. make up the required volume up to one liter with WFI and filter through 0.22-micron nylon filter, sealed and packed in sterilized vials.
Example 7 :
Preparation of 0.5 % solution of meloxicam with 2-Pyrollidone with out additives
Dissolve 5 g meloxicam in 0.54 liters of 2-PyroUidone and stir till a clear solution is formed. Add 0.14 liters of ethyl alcohol to the solution and stir for 5 min. make up the required volume up to one liter with WFI and filter through 0.22-micron nylon filter, sealed and packed in sterilized vials
Claims
1. The stable pharmaceutical composition of Meloxicam or its pharmaceutically acceptable salt thereof as injectables consisting of, a. pyrrolidone as solvent. b. ethanol. c. water for injection d. optionally involving the use of one or more salt forming agent.
2. The pharmaceutical composition as claimed in claim 1, wherein the pyrrolidone solvent consisting N-methyl-2-pyrrolidone, 2-pyrrolidone or mixtures thereof.
3. The pharmaceutical composition as claimed in claim 1, wherein the Pyrrolidone solvent concentration ranging from about 20 to about 80 %.
4. The pharmaceutical composition as claimed in claim 1, wherein the Pyrrolidone solvent concentration preferably ranging from about 45 to about 80 %.
5. The pharmaceutical composition as claimed in claim 1, wherein the Pyrrolidone solvent concentration preferably ranging from about 55 to about 70 %.
6. The stable pharmaceutical composition as claimed in claim 1, comprising the concentration of ethanol ranging from about 5 % to about 25%.
7. The stable pharmaceutical composition as claimed in claim 1, comprising the concentration of ethanol ranging from about 10 % to about 20%.
8. The stable pharmaceutical composition as claimed in claim 1, consisting of water preferably in concentration ranging from about 1% to about 20%.
9. The pharmaceutical composition according to claim 1, consisting of salt forming agent which forms preferable salts of sodium, potassium, ammonium, meglumine or mixture thereof.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1904/MUM/2006 | 2006-11-20 | ||
| IN1904MU2006 | 2006-11-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2008062274A2 true WO2008062274A2 (en) | 2008-05-29 |
| WO2008062274A3 WO2008062274A3 (en) | 2009-04-23 |
Family
ID=39430108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB2007/003515 WO2008062274A2 (en) | 2006-11-20 | 2007-11-16 | Pharmaceutical formulations of nsaids for parentral use |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2008062274A2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019214715A1 (en) | 2018-05-11 | 2019-11-14 | 南京清普生物科技有限公司 | Meloxicam composition, preparation and preparation method and use thereof |
| WO2021224815A1 (en) * | 2020-05-06 | 2021-11-11 | Cadila Healthcare Limited | Stable aqueous parenteral solutions of nonsteroidal anti-inflammatory drug (nsaid) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4374826A (en) * | 1980-07-21 | 1983-02-22 | Pfizer Inc. | Sulfonamide compositions |
| US20020035107A1 (en) * | 2000-06-20 | 2002-03-21 | Stefan Henke | Highly concentrated stable meloxicam solutions |
| US20050187212A1 (en) * | 2002-09-17 | 2005-08-25 | Nippon Boehringer Ingelheim Co., Ltd. | Pharmaceutical composition for topical delivery of meloxicam |
-
2007
- 2007-11-16 WO PCT/IB2007/003515 patent/WO2008062274A2/en active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4374826A (en) * | 1980-07-21 | 1983-02-22 | Pfizer Inc. | Sulfonamide compositions |
| US20020035107A1 (en) * | 2000-06-20 | 2002-03-21 | Stefan Henke | Highly concentrated stable meloxicam solutions |
| US20050187212A1 (en) * | 2002-09-17 | 2005-08-25 | Nippon Boehringer Ingelheim Co., Ltd. | Pharmaceutical composition for topical delivery of meloxicam |
Non-Patent Citations (1)
| Title |
|---|
| ROWE ET AL.: 'Handbook of Pharmaceutical Excipients', 2006 pages 633 - 634 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019214715A1 (en) | 2018-05-11 | 2019-11-14 | 南京清普生物科技有限公司 | Meloxicam composition, preparation and preparation method and use thereof |
| EP3777862A4 (en) * | 2018-05-11 | 2021-07-07 | Nanjing Delova Biotech Co. Ltd. | Meloxicam composition, preparation and preparation method and use thereof |
| JP2021521212A (en) * | 2018-05-11 | 2021-08-26 | 南京清普生物科技有限公司 | Meloxicam compositions, formulations and methods and applications thereof |
| JP7374501B2 (en) | 2018-05-11 | 2023-11-07 | 南京清普生物科技有限公司 | Meloxicam compositions, preparations and their manufacturing methods and applications |
| WO2021224815A1 (en) * | 2020-05-06 | 2021-11-11 | Cadila Healthcare Limited | Stable aqueous parenteral solutions of nonsteroidal anti-inflammatory drug (nsaid) |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008062274A3 (en) | 2009-04-23 |
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