WO1998055113A1 - Semisolid pharmaceutical formulation containing dexketoprofen trometamol - Google Patents
Semisolid pharmaceutical formulation containing dexketoprofen trometamol Download PDFInfo
- Publication number
- WO1998055113A1 WO1998055113A1 PCT/EP1998/003333 EP9803333W WO9855113A1 WO 1998055113 A1 WO1998055113 A1 WO 1998055113A1 EP 9803333 W EP9803333 W EP 9803333W WO 9855113 A1 WO9855113 A1 WO 9855113A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- tromethamine
- agent
- pharmaceutical formulation
- gel
- dexketoprofen
- Prior art date
Links
Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- 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
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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]
Definitions
- the present invention relates to a process for the preparation of a semisolid pharmaceutical formulation (gel or cream) containing dexketoprofen tro etamol and different amines as neutralizing agents, for the topical treatment of inflammatory processes in humans.
- the pharmaceutical formulations obtained by said process are also object of the present invention and show advantages deriving from their high storage stability without noticeable changes in the appearance of the product in time, a well as from their lower allergenic and photoallergenic activities.
- NSAID used in therapy for example arylpropionic or arylacetic acids derivatives
- Carboxyvinyl polymers can be used as gelifying agents in the preparation of gels with this type of NSAID, these polymers need the mandatory presence of a neutralizing base to increase their viscosity and to attain their correct gelification.
- the base In order to obtain a good gelification with this type of compounds, the base has to neutralize both the gelifying agent and the active principle.
- the most widely used bases for this purpose are amines, such as triethanolamine and diethanolamine .
- tromethamine DCI trometamol, 2-amino-2-(hydroxyethyl )-l, 3-propanediol
- tromethamine has also been used as neutralizing agent in the preparation of gels for therapeutic use, due to its suitable physical- chemical characteristics as well as to its low toxicity (Bremecker K.D. Pharm. Ind. 51 (2) 199-202 (1989)).
- Tromethamine has remarkable advantages both from the physical-chemical and from the toxicologic point of view, compared with the commonly used amines, such as triethanolamine and diethanolamine.
- triethanolamine and diethanolamine proved to be potentially harmful, in particular carcinogenic, compounds both in in vi tro cellular models (Santa aria A. et al. ⁇ cotoxicol. Environ. Saf.
- tromethamine itself is used as a medicament in respiratory and metabolic acidosis syndromes (USP XXIII and European Pharmacopoeia 3rd Ed.).
- tromethamine has recently been used also as neutralizing agent in the preparation of gels for the therapeutic use.
- the physical characteristics of the resulting pharmaceutical formulations are similar to those obtained with triethanolamine, as far as pH, viscosity, organoleptic characteristics and storage stability are concerned (Kim H. et al. JP 07309938, 1995 and Tamburick S. et al. Pharm. Res. 13 (2) 279-83 (1996)).
- tromethamine as neutralizing agent allows, due to its lower basicity, to add the a ine in larger amounts than the stoic iometric and, as a consequence, the maximum viscosity area does not take place after the stoichiometric addition of the amine, as it happens when using triethanolamine or diethanolamine, but after the addition of larger amounts of the amine, the buffering power of the resulting formulation being much higher
- Tromethamine has been used in pharmaceutical semisolid formulations (gels and liposomes) for the treatment of acne and psoriasis ( Charu P.M. WO 9533489, 1995 and Hager J.-C. DE 4322158, 1995), in oxytocic gels containing prostaglandins ⁇ , A and F2a (Kravciv M. et al.
- ketorolac tromethamine salt for the administration of this compound in the form of dentifrice gel (Cavanaugh P.F. et al. WO-9628144 Al ,
- the present invention aims therefore at obtaining gels of the analgesic and antiinflammatory medicament dexketoprofen trometamol having a complete storage stability without noticeable changes in the appearance of the product in time.
- a polyacrylic gel of an arylpropionic acid can be prepared starting from the active principle as the free acid, dissolving it in a suitable solvent such as ethanol and adding it with a dispersion formed by carbomer and water; finally, neutralizing it with a physiologically compatible amine, such as triethanolamine, diethanolamine or tromethamine, to obtain the desired gel.
- a physiologically compatible amine such as triethanolamine, diethanolamine or tromethamine
- the dexketoprofen trometamol gel prepared with tromethamine turned out to be remarkably less photoallergenic than conventional gels.
- dexketoprofen trometamol as therapeutical agent together with diethanolamine or triethanolamine may be considered when a reduction in the amine content in the gel is desired.
- the process for the preparation of a gel containing dexketoprofen trometamol at a concentration ranging between 1.5 and 4.5% typically comprises the formation first of a dispersion containing 0.5 to 5% of carbomer, 10-40% of ethanol and 60-90% of demineralized water, optionally in the presence of a suitable essence oil (0.05-0.5%).
- This dispersion is then added with a solution containing dexketoprofen trometamol (from 1.5 to 4.5% on the total amount of gel) and a suitable amine (from 0.5 to 3% on the total amount of gel), such as tromethamine, triethanolamine or diethanolamine, in demineralized water (4-10% on the basis of the total amount of gel).
- a suitable amine from 0.5 to 3% on the total amount of gel
- pH is checked to range between 5 and 7, preferably between 6 and 6.5.
- the gel is de-aerated under mild vacuum.
- dexketoprofen trometamol can also be prepared in si tu.
- the process consists in the preparation of a 1-3% dexketoprofen solution on the basis of the total amount of gel in ethanol (25-40%) containing a suitable essence oil (0.05-0.5%), which solution is then added with a dispersion of 0.5-5% of carbomer in water. After a suitable time from 15 to 30 min. for the correct homogenization of the formed dispersion, tromethamine is added in an equimolar amount to dexketoprofen (between
- a physiologically compatible amine such as triethanolamine, diethanolamine or tromethamine
- the gels of the invention have a long-term storage stability under conventional conditions (15-35°C) for long periods of time and exhibit excellent antiinflam a- tory and analgesic effects without involving noticeable toxic effects when directly applied to the skin.
- Example 1 Preparation of a gel starting from tromethamine ( + )-(S)-2-( 3-benzoylphenyl )propionate using tromethamine as neutralizing agent.
- a 200 L reactor equipped with a stirrer is loaded with 40.8 L of ethanol, 0.1 kg of a suitable essence oil, 57.5 L of demineralized water and 1.5 kg of carbomer.
- the mixture is stirred to a homogeneous dispersion (15 min).
- the resulting dispersion is added with a solution of 1.4 kg of tromethamine, 1.85 kg of tromethamine (+)-(S)-2-(3-benzoylphenyl)propionate and 5.65 L of water, stirring to obtain a correct incorporation (15 min). After this time, stirring is stopped and pH is checked to range from 6 to 6.5. Finally, the resulting gel is de-aerated under mild vacuu .
- Example 2 Preparation of a gel starting from tromethamine ( + )-(S )-2-( 3-benzoylphenyl )propionate using diethanolamine as neutralizing agent.
- a 200 L reactor equipped with a stirrer is loaded with 40.8 L of ethanol, 0.1 kg of a suitable essence oil, 57.5 L of demineralized water and 1.5 kg of carbomer.
- the mixture is stirred to a homogeneous dispersion (15 min).
- the resulting dispersion is added with a solution of 1.04 kg of diethanolamine, 1.85 kg of tromethamine (+ )-(S)-2-( 3-benzoylphenyl )propionate and 6.01 L of water, stirring to obtain a correct incorporation (15 min). After this time, stirring is stopped and pH is checked to range from 6 to 6.5. Finally, the resulting gel is de-aerated under mild vacuum.
- Example 3 Preparation of a gel starting from tromethamine ( + )-( S )-2-( 3-benzoylphenyl )propionate using triethanolamine as neutralizing agent.
- a 200 L reactor equipped with a stirrer is loaded with 40.8 L of ethanol, 0.1 kg of a suitable essence oil, 57.5 L of demineralized water and 1.5 kg of carbomer.
- the mixture is stirred to a homogeneous dispersion (15 min).
- the resulting dispersion is added with a solution of 1.58 kg of triethanolamine, 1.85 kg of tromethamine (+)-(S)-2-(3-benzoylphenyl)propionate and 5.47 L of water, stirring to obtain a correct incorporation (15 min). After this time, stirring is stopped and pH is checked to range from 6 to 6.5. Finally, the resulting gel is de-aerated under mild vacuum.
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)
- Inorganic Chemistry (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
UA99116289A UA57075C2 (en) | 1997-06-04 | 1998-04-06 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
NZ501487A NZ501487A (en) | 1997-06-04 | 1998-06-04 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
JP50151599A JP2002502407A (en) | 1997-06-04 | 1998-06-04 | Semi-solid drug formulation containing dexketoprofentromethamol |
EP98937444A EP0996437B1 (en) | 1997-06-04 | 1998-06-04 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
DE69800804T DE69800804T2 (en) | 1997-06-04 | 1998-06-04 | SEMI-SOLID PHARMACEUTICAL PREPARATIONS CONTAINING DEXKETOPROFEN-TROMETAMOL |
BRPI9810072-6A BR9810072B1 (en) | 1997-06-04 | 1998-06-04 | semi-solid pharmaceutical formulation containing dexketoprofen trometamol and process for preparing it. |
KR1019997011315A KR100543558B1 (en) | 1997-06-04 | 1998-06-04 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
CA002293589A CA2293589C (en) | 1997-06-04 | 1998-06-04 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
AT98937444T ATE201137T1 (en) | 1997-06-04 | 1998-06-04 | SEMI-SOLID PHARMACEUTICAL PREPARATIONS CONTAINING DEXKETOPROFEN-TROMETAMOLE |
PL337156A PL190779B1 (en) | 1997-06-04 | 1998-06-04 | Method for manufacture of semi-solid pharmaceutical compound containing, as therapeutic agent, the (+)-(s)-2-(3-benzoylphenyl) propionic acid salt with thrometamine and semi-solid pharmaceutical compound containing thrometamol dexketoprophene |
EA199900998A EA002026B1 (en) | 1997-06-04 | 1998-06-04 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
AU86244/98A AU728442B2 (en) | 1997-06-04 | 1998-06-04 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
EEP199900556A EE03905B1 (en) | 1997-06-04 | 1998-06-04 | Semi-solid pharmaceutical preparations containing dexketoprofen trometamol |
SK1649-99A SK284317B6 (en) | 1997-06-04 | 1998-06-04 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
HU0002734A HU226686B1 (en) | 1997-06-04 | 1998-06-04 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
DK98937444T DK0996437T3 (en) | 1997-06-04 | 1998-06-04 | Semifast pharmaceutical formulation containing dexketoprofentrometamol |
BG103926A BG64299B1 (en) | 1997-06-04 | 1999-11-25 | Semisolid pharmaceutical form containing dexketoprophene trometamol |
HK00106945A HK1027753A1 (en) | 1997-06-04 | 2000-11-01 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
GR20010401170T GR3036319T3 (en) | 1997-06-04 | 2001-08-03 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES009701213A ES2124196B1 (en) | 1997-06-04 | 1997-06-04 | PROCEDURE FOR THE MANUFACTURE OF A SEMI-SOLID PHARMACEUTICAL FORM CONTAINING DEXKETOPROPHEN TROMETAMOL AND ITS USE IN THE TOPICAL TREATMENT OF INFLAMMATION. |
ESP9701213 | 1997-06-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998055113A1 true WO1998055113A1 (en) | 1998-12-10 |
Family
ID=8299560
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/003333 WO1998055113A1 (en) | 1997-06-04 | 1998-06-04 | Semisolid pharmaceutical formulation containing dexketoprofen trometamol |
Country Status (29)
Country | Link |
---|---|
EP (1) | EP0996437B1 (en) |
JP (1) | JP2002502407A (en) |
KR (1) | KR100543558B1 (en) |
CN (1) | CN1195510C (en) |
AT (1) | ATE201137T1 (en) |
AU (1) | AU728442B2 (en) |
BG (1) | BG64299B1 (en) |
BR (1) | BR9810072B1 (en) |
CA (1) | CA2293589C (en) |
CU (1) | CU22866A3 (en) |
CZ (1) | CZ290118B6 (en) |
DE (1) | DE69800804T2 (en) |
DK (1) | DK0996437T3 (en) |
EA (1) | EA002026B1 (en) |
EC (1) | ECSP014108A (en) |
EE (1) | EE03905B1 (en) |
ES (2) | ES2124196B1 (en) |
GR (1) | GR3036319T3 (en) |
HK (1) | HK1027753A1 (en) |
HN (1) | HN2001000137A (en) |
HU (1) | HU226686B1 (en) |
ID (1) | ID26240A (en) |
NZ (1) | NZ501487A (en) |
PL (1) | PL190779B1 (en) |
PT (1) | PT996437E (en) |
SK (1) | SK284317B6 (en) |
TR (1) | TR199903018T2 (en) |
UA (1) | UA57075C2 (en) |
WO (1) | WO1998055113A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19935159A1 (en) * | 1999-07-27 | 2001-02-22 | Schuster Wolfgang | Muscle relaxant lotion containing natural active agents and penetration enhancing carrier |
FR2797766A1 (en) * | 1999-08-27 | 2001-03-02 | Menarini France | Paste in gel form for topical application, containing an anti-inflammatory, an antibiotic or a phlebotonic |
WO2013022410A2 (en) | 2011-08-08 | 2013-02-14 | Mahmut Bilgic | Production method for effervescent formulations comprising dexketoprofen |
EP2764875A1 (en) * | 2013-02-06 | 2014-08-13 | Galenicum Health S.L. | Process for preparing a stable pharmaceutical composition comprising dexketoprofen trometamol |
WO2016016353A1 (en) * | 2014-07-30 | 2016-02-04 | Pierre Fabre Medicament | Stearate emulsions |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2667465C2 (en) * | 2015-10-28 | 2018-09-19 | Закрытое Акционерное Общество "Фармфирма "Сотекс" | Pharmaceutical composition for external use containing a salt of dexketoprofen, and a process for its preparation |
CN109303762A (en) * | 2017-07-28 | 2019-02-05 | 韩美药品株式会社 | Semisolid preparation and preparation method thereof containing Ketoprofen |
KR101935830B1 (en) * | 2018-02-13 | 2019-01-07 | 주식회사 오스테오시스 | External counterpulsation system and control method thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE886486A (en) * | 1979-12-05 | 1981-04-01 | Menarini Sas | PHARMACEUTICAL FORM "GEL" CONTAINING 2- (3-BENZOYL-PHENYL) -PROPIONIC ACID AND ITS USE IN THERAPEUTICS FOR LOCAL USE |
US5091182A (en) * | 1990-07-23 | 1992-02-25 | Syntex (U.S.A.) Inc. | Dispensing units for ketorolac topical gel formlations |
WO1994011332A1 (en) * | 1992-11-10 | 1994-05-26 | Laboratorios Menarini S.A. | A novel arylpropionic derivative, a process for the preparation and the use thereof as an analgesic agent |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2319340A1 (en) * | 1975-07-28 | 1977-02-25 | Roussel Uclaf | NEW SALT OF A-METHYL BENZOYL-5-THIOPHENE-2 ACETIC ACID, METHOD OF PREPARATION AND APPLICATION AS A MEDICINAL PRODUCT |
IT1207994B (en) * | 1986-01-03 | 1989-06-01 | Therapicon Srl | WATER SOLUBLE SALTS OF ANTI-INFLAMMATORY AND ANALGESIC ADAPTITY COMPOUNDS, THEIR PREPARATION AND USE IN PHARMACEUTICAL COMPOSITIONS. |
US4960892A (en) * | 1988-06-10 | 1990-10-02 | American Home Products Corporation | Naphthalenepropionic acid derivatives as anti-inflammatory/anti-allergic agents |
-
1997
- 1997-06-04 ES ES009701213A patent/ES2124196B1/en not_active Expired - Lifetime
-
1998
- 1998-04-06 UA UA99116289A patent/UA57075C2/en unknown
- 1998-06-04 DE DE69800804T patent/DE69800804T2/en not_active Expired - Lifetime
- 1998-06-04 AT AT98937444T patent/ATE201137T1/en active
- 1998-06-04 ID IDW991478A patent/ID26240A/en unknown
- 1998-06-04 EA EA199900998A patent/EA002026B1/en not_active IP Right Cessation
- 1998-06-04 DK DK98937444T patent/DK0996437T3/en active
- 1998-06-04 SK SK1649-99A patent/SK284317B6/en not_active IP Right Cessation
- 1998-06-04 CN CNB988057417A patent/CN1195510C/en not_active Expired - Lifetime
- 1998-06-04 AU AU86244/98A patent/AU728442B2/en not_active Expired
- 1998-06-04 CZ CZ19994313A patent/CZ290118B6/en not_active IP Right Cessation
- 1998-06-04 TR TR1999/03018T patent/TR199903018T2/en unknown
- 1998-06-04 NZ NZ501487A patent/NZ501487A/en not_active IP Right Cessation
- 1998-06-04 BR BRPI9810072-6A patent/BR9810072B1/en not_active IP Right Cessation
- 1998-06-04 PT PT98937444T patent/PT996437E/en unknown
- 1998-06-04 JP JP50151599A patent/JP2002502407A/en active Pending
- 1998-06-04 EP EP98937444A patent/EP0996437B1/en not_active Expired - Lifetime
- 1998-06-04 ES ES98937444T patent/ES2156446T3/en not_active Expired - Lifetime
- 1998-06-04 HU HU0002734A patent/HU226686B1/en unknown
- 1998-06-04 PL PL337156A patent/PL190779B1/en unknown
- 1998-06-04 KR KR1019997011315A patent/KR100543558B1/en not_active IP Right Cessation
- 1998-06-04 WO PCT/EP1998/003333 patent/WO1998055113A1/en active IP Right Grant
- 1998-06-04 CA CA002293589A patent/CA2293589C/en not_active Expired - Lifetime
- 1998-06-04 EE EEP199900556A patent/EE03905B1/en unknown
-
1999
- 1999-11-25 BG BG103926A patent/BG64299B1/en unknown
- 1999-11-30 CU CU1999212A patent/CU22866A3/en unknown
-
2000
- 2000-11-01 HK HK00106945A patent/HK1027753A1/en not_active IP Right Cessation
-
2001
- 2001-06-27 HN HN2001000137A patent/HN2001000137A/en unknown
- 2001-06-29 EC EC2001004108A patent/ECSP014108A/en unknown
- 2001-08-03 GR GR20010401170T patent/GR3036319T3/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE886486A (en) * | 1979-12-05 | 1981-04-01 | Menarini Sas | PHARMACEUTICAL FORM "GEL" CONTAINING 2- (3-BENZOYL-PHENYL) -PROPIONIC ACID AND ITS USE IN THERAPEUTICS FOR LOCAL USE |
US5091182A (en) * | 1990-07-23 | 1992-02-25 | Syntex (U.S.A.) Inc. | Dispensing units for ketorolac topical gel formlations |
WO1994011332A1 (en) * | 1992-11-10 | 1994-05-26 | Laboratorios Menarini S.A. | A novel arylpropionic derivative, a process for the preparation and the use thereof as an analgesic agent |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19935159A1 (en) * | 1999-07-27 | 2001-02-22 | Schuster Wolfgang | Muscle relaxant lotion containing natural active agents and penetration enhancing carrier |
FR2797766A1 (en) * | 1999-08-27 | 2001-03-02 | Menarini France | Paste in gel form for topical application, containing an anti-inflammatory, an antibiotic or a phlebotonic |
WO2013022410A2 (en) | 2011-08-08 | 2013-02-14 | Mahmut Bilgic | Production method for effervescent formulations comprising dexketoprofen |
EP2764875A1 (en) * | 2013-02-06 | 2014-08-13 | Galenicum Health S.L. | Process for preparing a stable pharmaceutical composition comprising dexketoprofen trometamol |
WO2016016353A1 (en) * | 2014-07-30 | 2016-02-04 | Pierre Fabre Medicament | Stearate emulsions |
FR3024360A1 (en) * | 2014-07-30 | 2016-02-05 | Pf Medicament | EMULSIONS TO STEARATES |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0101178B1 (en) | Topical anti-inflammatory compositions | |
CY1108488T1 (en) | Solid Compositions Containing Gamma-Aminobutyric Acid Derivatives and Method for Their Preparation | |
CH630260A5 (en) | ANTIBIOTIC COMPOSITIONS BASED ON A TETRACYCLINE. | |
KR20160091424A (en) | Compositions for continuous administration of DOPA decarboxylase inhibitors | |
JPH078786B2 (en) | Percutaneously absorbable hydrous preparation of arylpropionic acid derivative and method for producing the same | |
JP2008542260A (en) | Novel injectable composition and method for its preparation | |
EP0996437B1 (en) | Semisolid pharmaceutical formulation containing dexketoprofen trometamol | |
EP3097907B1 (en) | A gel formulation comprising analgesic and anesthesic agents | |
US4621075A (en) | Gel-form topical antibiotic compositions | |
US4602040A (en) | Meclofenamic acid topical pharmaceutical composition | |
JP3608209B2 (en) | Crotamiton combination external preparation | |
EP2292218B1 (en) | Topical application of nimesulide and thiocolchicoside | |
MXPA99011180A (en) | Semisolid pharmaceutical formulation containing dexketoprofen trometamol | |
JPH08259464A (en) | Local anesthetic composition | |
EP2340016B1 (en) | Topical formulation of 3-(2,2,2-trimethylhydrazinium) propionate dihydrate | |
GB2327041A (en) | Topical Analgesic Composition | |
EP0492747B1 (en) | Pharmaceutical preparation for topical application | |
JPS63287721A (en) | Anti-inflammatory analgesic gel agent | |
JP3313894B2 (en) | Transdermal absorption enhancer and skin external preparation | |
GB2236250A (en) | Ibuprofen solutions and topical compositions | |
JPH05117141A (en) | Antiinflammatory analgesic gel preparation containing adrenal essence | |
JP3522832B2 (en) | Percutaneous absorption enhancer and external preparation for skin | |
IL100595A (en) | Pharmaceutical preparation for topical application comprising a clonixinate salt |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 98805741.7 Country of ref document: CN |
|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH GM GW HU ID IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW SD SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG |
|
CFP | Corrected version of a pamphlet front page | ||
CR1 | Correction of entry in section i | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1998937444 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 2293589 Country of ref document: CA Ref document number: 2293589 Country of ref document: CA Kind code of ref document: A Ref document number: 1999 501515 Country of ref document: JP Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 164999 Country of ref document: SK Ref document number: PA/a/1999/011180 Country of ref document: MX Ref document number: PV1999-4313 Country of ref document: CZ Ref document number: 86244/98 Country of ref document: AU Ref document number: 09445095 Country of ref document: US Ref document number: 1019997011315 Country of ref document: KR Ref document number: 501487 Country of ref document: NZ Ref document number: 1999/03018 Country of ref document: TR Ref document number: 199900998 Country of ref document: EA |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWP | Wipo information: published in national office |
Ref document number: 1998937444 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: PV1999-4313 Country of ref document: CZ |
|
WWP | Wipo information: published in national office |
Ref document number: 1019997011315 Country of ref document: KR |
|
WWG | Wipo information: grant in national office |
Ref document number: 86244/98 Country of ref document: AU |
|
WWG | Wipo information: grant in national office |
Ref document number: 1998937444 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: PV1999-4313 Country of ref document: CZ |
|
WWG | Wipo information: grant in national office |
Ref document number: 1019997011315 Country of ref document: KR |