NZ208693A - Formulations of etofenamate:2-(2-hydroxyethoxy)-ethyl n-(alpha,alpha,alpha-trifluoro-m-tolyl)anthranilate - Google Patents
Formulations of etofenamate:2-(2-hydroxyethoxy)-ethyl n-(alpha,alpha,alpha-trifluoro-m-tolyl)anthranilateInfo
- Publication number
- NZ208693A NZ208693A NZ208693A NZ20869384A NZ208693A NZ 208693 A NZ208693 A NZ 208693A NZ 208693 A NZ208693 A NZ 208693A NZ 20869384 A NZ20869384 A NZ 20869384A NZ 208693 A NZ208693 A NZ 208693A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formulation according
- adjuvant
- etofenamate
- weight
- acid
- Prior art date
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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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
-
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Dermatology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Color Television Image Signal Generators (AREA)
- Stereophonic System (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Fats And Perfumes (AREA)
Abstract
1. Cream formulation for etofenamate, characterized in that it contains 5 to 80% by weight of isopropyl myristate and 2 to 30% by weight of etofenamate.
Description
<div class="application article clearfix" id="description">
<p class="printTableText" lang="en">New Zealand Paient Spedficaiion for Paient Number £08693 <br><br>
208693 <br><br>
Priority Date(s): .7..?.? <br><br>
Complete Specification Filed: A?-: ^ <br><br>
c,ass: . mtki/a?. <br><br>
. Publication Date: tl 2 NOV 1985 <br><br>
| P.O. 4ournal, No: <br><br>
m drawings <br><br>
N.Z.No. <br><br>
NEW ZEALAND <br><br>
Patents Act 1953 <br><br>
COMPLETE SPECIFICATION <br><br>
N.Z. PATENT OFFICE ""*? ;2 8JUNI984 ;RECEIVED ;"ETOFENAMATE FORMULATION" ;We, TROPONWERKE GmbH & CO. KG, a company registered under the laws of the Federal Republic of Germany, of Koeln, Germany, do hereby declare the invention, for Which we pray that a ;Patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement : - ;- 1 — (followed by 1A) ;208693 ;- ifl- ;The present invention relates to an antiinflamma-tory medicament formulation which has an analgesic action and is to be applied topically, and which contains 2- (2-hydroxyethox^-ethyl N-(<v>V,<\'-trifluoro-m-tolyl)anthrani late, called Etofenamate below, as the essential active compound. Etofenamate has the following structure: ;Etofenamate is already known as a non-steroid medicament with a good antiinflammatory action and outstanding tolerance, compare Arzneimittelforschung 27 (I) Special Edition 6 b, 1299-1364, 1977. Etofenamate has hitherto been used in the form of alcohol-containing gels. Because of the alcohol, the gel has a cooling action when applied, and this has not been found pleasant by all patients. Furthermore, such a gel can be applied only to intact skin, and a desirable application in cases of trauma with open wounds is thus not possible. In addition, such a formulation is of only limited suitability for patients with an exceptionally dry skin. ;An object of the present invention is thus to overcome the disadvantages described by providing a new formulation which, however, has the antiinflammatory and analgesic action to the same degree as the gel form. ;Surprisingly, it has been possible to discover a cream formulation which has the required properties. ;The present invention thus relates to a cream formulation containing Etofenamate and an adjuvant. ;Etofenamate is a highly viscous oil, only traces ;208693 ;- 2 - ;of which dissolve in water. In a large number of galenical auxiliaries, it has only inadequate solubility, intei— actions, such as, for example, hydrolysis, transesterifi-cation, esterification and the like, take place, or de-mixing, phase separation and the like occurs. Although some formulations containing Etofenamate have proved homogeneous and stable, their absorption is inadequate in comparison with the known Etofenamate-containing gel. These disadvantages do not arise in the formulation according to the invention. In the formulation according to the invention, the absorption of Etofenamate by the skin is outstanding. ;The cream formulation according to the invention thus also contains, in addition to Etofenamate, an adjuvant and, if appropriate, agents which give the formula-tion consistency and/or emulsifiers and other auxiliaries, such as additives which promote circulation or have a warming effect or which have a pleasant odour. ;According to the invention, one or more compounds from the groups: triglycerides, and/or esters of mono-hydric and/or polyhydric alcohols, and/or higher alcohols, are used as the adjuvant. ;Adjuvants which are preferably used from the triglyceride group are one or more triglycerides of medium-chain carboxylic acids of C6 to C<j^ chain length in saturated or unsaturated and branched or straight-chain form, particularly preferably neutral oils, such as, for example, Miglyol 810 or Miglyol 812 or Viscoleo. ;Viscoleo is understood as meaning a mixture of saturated triglycerides of medium chain length and a fatty acid distribution of 45 - 60% of caprylic acid, 35 - 50% of capric acid and 2 - 10% of lauric acid, and Miglyol is understood as meaning a caprylic/capric acid triglyceride. ;An adjuvant from the group of esters of monohydric and/or polyhydric alcohols is preferably understood as meaning one or more esters of monohydric and/or polyhydric ;J ;- 3 - ;alcohols of Cj'C-jb chain length with carboxylic acid components of C^-C^g chain Length, particularly preferably propylene glycol diesters, ethyl oleat e, isopropyl myris-t at e, stearate or palmitate, diisopropyl adipate, diethyl 5 sebacate, oleyl oleate, hexyl laurate and isooctyl stearate, and very particularly preferably diisopropyl adipate and/or isopropyl myristate. ;An adjuvant from the group of higher alcohols is preferably understood as meaning oleyl alcohol and/or 2-10 octyl-dodecanol, particularly preferably 2-octyl-dodecanol, by itself. ;According to the invention, Etofenamate can be present in the formulations as a mixture with one or more adjuvants of all three groups or of only two groups or only 15 one group. ;Starting from these Etofenamate/adjuvant mixtures or solutions, various creams of a Liquid to semi-solid consistency can be prepared: 1. Oil-in-water emulsions, 2. Watei—in-oil emulsions and 3. MicroemuIsions. 20 According to the invention, it is necessary for the cream consisting of the active compound, and adjuvant to contain about 2 to about 30% by weight of Etofenamate as the active compound and about 5 to about 80% by weight of adjuvant or adjuvant mixtures as described above. The mi x-25 ture particularly preferably contains 5 - 15% by weight of Etofenamate, and particularly preferably 6 - 12% by weight. ;The formulation can furthermore also contain one or more agents to give it consistency and/or one or more emulsifiers and/or additives which promote circulation or O 30 have a warming effect and/or other auxiliaries, such as, ;for example, substances which have a pleasant odour, and/or also other active compounds. ;In many cases, agents which give the formulation consistency and emulsifiers are also identical, and strict 35 separation is thus not possible. ;As agents which give the formulation consistency, ;- 4 - ;there may be used one or more of the group of fatty alcohols of C^q to Cjq chain length, such as, for example, stearyl alcohol, hydrocarbons, such as petroleum jelly, paraffins, hard paraffins and waxes, such as beeswax or carnauba wax. It is furthermore also possible to use mono-glycerides, diglycerides and triglycerides, such as glycerol monostearate and glycerol distearate, and metal soaps, such as Al stearate, Aerosil and polyglycols, such as polyethylene glycols and polypropylene glycols. ;The consistency of the aqueous phase of water-con-taining formulations can be adjusted by means of hydrogel-forming agents, such as Veegum, cellulose derivatives (for example methyIceIlulose, hydroxyethyIceI luLose or carboxy-methyIceLluLose), carboxyvinyl polymers, alginic acid derivatives, gum arabicum and the Like. ;As the emuLsifier there may be used one or more from the group of ionic or non-ionic water-in-oil and oil-in-water emulsifiers. ;Compounds which are preferably used are salts of higher fatty acids and bile acids, such as triethanolamine stearate, alkyl sulphates, such as Na UauryL sulphate, aIkyLsulphonates, such as Na cetyIsulphonate, higher fatty alcohols, such as cetyl alcohol, lauryl alcohol and stearyl alcohol, sterol alcohols, such as cholesterol, fatty acid esters of polyhydric alcohols and polyols, such as ethylene monostearate, glycerol monooleate, sorbitan monolaurate, sorbitan trioleate, poLyoxyethylene-(20) sorbitan monolaurate and po lyoxyethy lene sorbitol hexaoleate, fatty alcohol ethers, such as polyoxyethylene Lauryl ether and polyoxyethylene oleyL ether, fatty acid esters of sucrose, such as sucrose distearate. Lecithin and derivatives, betaines and sulphobetaines, such as fatty acid ami do-alkylbetaine and/or polyoxyet.hylene/polyoxypropylene polymers, such as pluronics. ;Examples of additives which may be used which promote circulation or have a warming effect are benzyl nico- ;1086^5 ;- 5 - ;tinate, salicylic acid esters, for example methyIsa Iicy-late, ethereal oils, capsaicin, capsicum extract or nonylic acid vaniIlyI amide. ;The customary pharmacologically acceptable substances can be used as the odour substances, as long as they are compatible with the active compound and adjuvant. ;The amount of agents which give the formulation consistency and/or emulsifiers in the cream formulation, besides the Etofenamate and adjuvant, is up to about 70% by weight, and is preferably 5 to 25% by weight. ;Furthermore, the formulation also contains up to 85% by weight, preferably 40 to 60% by weight, of water. ;Formulations containing 2 to 30% by weight of Etofenamate, 5 - 80% by weight of adjuvant and 40 to 60% by weight of water are particularly preferred. ;The formulations, the composition of which can be seen from the examples, are furthermore particularly preferred. ;According to the invention, the antiinflammatory, analgesic formulations according to the invention are prepared by mixing the Etofenamate, dissolved in a suitable solvent, with any other molten fat/wax emulsifier constituents and then adding, with intensive mixing of the constituents, the aqueous phase, which has been brought to about the same temperature and contains preservatives, buffer and the like. Homogenisation is then carried out, for example by means of a rotor-stator device. ;The homogenisat ion temperature depends on the pai— ticular formulation and is generally between about 40°C and about 60°C. ;The Etofenamate formulation according to the invention contains the active compound in stable form and is capable of penetrating the skin without having the entraining function, for example, of isopropanol. Comparison studies with Etofenamate gel showed a bioequivalent absorption, which it was possible to demonstrate by an approxi- ;- 6 - ;mately equal absorption rate, timed to the maximum plasma level, maximum plasma level concentration, elimination from the plasma, area under the plasma level curves (AUC) and renal elimination in humans. ;5 The equivalence of the absorption is also shown by clinical trials, in which the activity was compared in a double-blind cross-over study against ointment containing 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid and against salicylic-containing ointments, and in which 10 the formulation according to the invention had a significantly Cp <0.05) better action, for example in lumbago cases in respect of the Schober distance and the spontaneous, movement and pressure pain, compared with the first comparison product, and proved significantly more 15 effective, for example in cases of acute gonathrosis in respect of the target parameters of joint mobility, joint range and spontaneous and movement pain, compared with the second comparison product. ;The present invention may be illustrated in more 20 detail by the following examples. ;:.X ;* <br><br>
- 7 - <br><br>
Example <br><br>
1 <br><br>
2 <br><br>
3 <br><br>
4 <br><br>
Etofenamate (mg) <br><br>
100 <br><br>
100 <br><br>
100 <br><br>
100 <br><br>
HjO <br><br>
(rag) <br><br>
522.5 <br><br>
512.5 <br><br>
509 <br><br>
522.5 <br><br>
Adjuvant (ng) <br><br>
Isopropyl myristate 100 <br><br>
Isopropyl nyristate 100 <br><br>
Diisopropyl adipatelOO <br><br>
Miglyol 8' 100 <br><br>
Emulsifier (mg) <br><br>
Myrj. 59 <br><br>
50 <br><br>
Myrj. 59 <br><br>
50 <br><br>
Myrj. 59 <br><br>
50 <br><br>
Myrj. 59 <br><br>
50 <br><br>
Benzyl alcohol (mg) <br><br>
15 <br><br>
15 <br><br>
15 <br><br>
15 <br><br>
Tylose MH 4000 (mg) <br><br>
7.5 <br><br>
7.5 <br><br>
7.5 <br><br>
7.5 <br><br>
Agent which gives consistency (mg) <br><br>
Cutina MD 175 <br><br>
Cutina MD 175 <br><br>
Cutina MD 175. <br><br>
Cutina MD 175 <br><br>
Citrate byffer solution (mg) <br><br>
30 <br><br>
30 <br><br>
30 <br><br>
30 <br><br>
Benzyl nicotinate <br><br>
- <br><br>
10 <br><br>
— <br><br>
208693 <br><br>
Example <br><br>
5 <br><br>
6 <br><br>
7 <br><br>
6 <br><br>
Etofenamate (mg) <br><br>
100 <br><br>
50 <br><br>
100 <br><br>
100 <br><br>
HjO <br><br>
(mg) <br><br>
613 <br><br>
679 <br><br>
603 <br><br>
605 <br><br>
Adjuvant <br><br>
(mg) <br><br>
Diisopropyl adipate <br><br>
130 <br><br>
Diisopropyl adipate 110 <br><br>
Diisopropyl adipate 1 jO <br><br>
Miglyol 81 <br><br>
Emulsifier (mg) <br><br>
Myrj. 59 50 <br><br>
^.59 <br><br>
59 <br><br>
ienzyl alcohol (mg) <br><br>
15 <br><br>
15 <br><br>
15 <br><br>
15 <br><br>
Tylose MH 4000 (mg) <br><br>
— <br><br>
— <br><br>
Agent which gives consistency (mg) <br><br>
Cutir.a GMS 37 <br><br>
Cutina GMS 41 <br><br>
Cut in a GMS 37 <br><br>
Cutina GMS 4 5 <br><br>
Citrate buffer solution (mg; <br><br>
30 <br><br>
30 <br><br>
30 <br><br>
30 <br><br>
Benzyl nicotinate <br><br>
— <br><br>
10 <br><br>
— <br><br>
— <br><br>
Cetyl alcohol <br><br>
10 <br><br>
10 <br><br>
10 <br><br>
'iO <br><br>
Veegum <br><br>
15 <br><br>
15 <br><br>
15 <br><br>
15 <br><br>
2086 9 <br><br>
9 - <br><br>
Example <br><br>
9 <br><br>
10 <br><br>
11 <br><br>
Etofenamate <br><br>
(mg) <br><br>
200 <br><br>
50 <br><br>
200 <br><br>
1^0 <br><br>
(mg) <br><br>
442 <br><br>
582 <br><br>
442 <br><br>
Adjuvant (mg) <br><br>
Isopropyl- <br><br>
myristate <br><br>
100 <br><br>
Isopropyl- <br><br>
myristate <br><br>
100 <br><br>
Diisopropyl-adipate 100 <br><br>
Emulsifier (mg) <br><br>
Myrj. 59 50 <br><br>
Mgd. 59 <br><br>
^.59 <br><br>
Benzyl alcohol (mg) <br><br>
15 <br><br>
15 <br><br>
15 <br><br>
Tylose MH 4000 (mg) <br><br>
8.0 <br><br>
8-0 <br><br>
8.0 <br><br>
Agent which gives consistency <br><br>
(mg) <br><br>
Cutina MD 155 <br><br>
Cutina MD 165 <br><br>
Cutina MD 155 <br><br>
Citrate byffer solution (mg; <br><br>
30 <br><br>
30 <br><br>
30 <br><br>
Benzyl nicotinate <br><br>
— <br><br>
— <br><br></p>
</div>
Claims (15)
1. A Formulation containing Etofenamate and one or more adjuvants and, if appropriate, agents which give the formulation consistency and/or emulsifiers and/or other auxiliaries.<br><br>
2. A Formulation according to claim 1, containing, as the adjuvant, one or more from the groups: triglycerides, esters of monohydric and/or polyhydric alcohols, and higher alcohols having from 2 to 18 carbon atoms.<br><br>
3. A Formulation according to claim 1 or 2, containing, as the adjuvant, one or more triglycerides of medium-chain carboxylic acids having from 6 to 14 carbon atoms in saturated or unsaturated and branched or straight-chain form.<br><br>
4. A Formulation according to claim 3, wherein the adjuvant is a neutral oil and/or Viscoleo.<br><br>
5. A Formulation according to one or more of claims 1 to 3, containing as adjuvant one or more esters of monohydric or polyhydric alcohols having 2 to 18 carbon atoms with carboxylic acid components of 6 to carbon atoms.<br><br>
6. A Formulation according to claim 5, wherein the adjuvant is selected from propylene glycol diesters, ethyl oleate, isopropyl myristate, stearate or palmitate, diisopropyl adipate, diethyl sebacate, oleyl oleate, hexyl laurate and isooctyl stearate.<br><br>
7. A Formulation according to claim 6, wherein the adjuvant is diisopropyl adipate and/or isopropyl myristate.<br><br>
8. A Formulation according to one or more of claims 1 to 3, containing as adjuvant oleyl alcohol and/or 2-octyl-dodecanol.<br><br>
9. A Formulation according to one or more of claims 1 to 8, containing 2 to 30% by weight of Etofenamate and 5 to 80%<br><br> 208693<br><br> - 12 -<br><br> r><br><br> by weight of adjuvant.<br><br>
10. A Formulation according to one or more of claims 1 to 8, containing up to 85% by weight of water.<br><br> ,
11. A Formulation according to claim 10 containing between and 60% by weight JuHntsWi<br><br> \ i/<br><br> o o<br><br>
12. A Formulation according to one or more of claims 1 to<br><br> 8, containing 2 to 30% by weight of Etofenamate, 5 to 80% by weight of adjuvant and 40 to 60% by weight of water.<br><br>
13. A process for the preparation of formulations according to one or more of claims 1 to 12, characterised in that Etofenamate, dissolved in a suitable solvent, is mixed with any other constituents, the aqueous phase is added, with intensive mixing, and the mixutre is then homogenised.<br><br>
14. Use of the formulation according to one or more of claims 1 to 13 as a topical analgesic and/or anti-inflammatory agent with the proviso that such use excludes treatment of the human body.<br><br>
15. A Formulation according to claim 1 substantially as herein described or exemplified.<br><br> G<br><br> TROPONWERKE GmbH & CO. By their attorneys HENRY HUGHES LIMITED<br><br> KG,<br><br> </p> </div>
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833323832 DE3323832A1 (en) | 1983-07-01 | 1983-07-01 | OVEN AMATE PREPARATION |
Publications (1)
Publication Number | Publication Date |
---|---|
NZ208693A true NZ208693A (en) | 1986-11-12 |
Family
ID=6202950
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NZ208693A NZ208693A (en) | 1983-07-01 | 1984-06-28 | Formulations of etofenamate:2-(2-hydroxyethoxy)-ethyl n-(alpha,alpha,alpha-trifluoro-m-tolyl)anthranilate |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0130516B1 (en) |
JP (1) | JPS6025921A (en) |
KR (1) | KR920006905B1 (en) |
AT (1) | ATE56867T1 (en) |
AU (1) | AU563760B2 (en) |
DE (2) | DE3323832A1 (en) |
FI (1) | FI842612A (en) |
NZ (1) | NZ208693A (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4810387A (en) * | 1985-09-28 | 1989-03-07 | Kleentek Industrial Co., Ltd. | Method for removing water soluble substances in non-water-soluble fluid |
US4738842A (en) * | 1986-01-17 | 1988-04-19 | Riker Laboratories | Topical antiinflammatory compositions |
DE3632359A1 (en) * | 1986-09-24 | 1988-04-07 | Troponwerke Gmbh & Co Kg | PREPARATIONS FOR MEDICINAL PRODUCTS |
WO1992011036A1 (en) * | 1990-12-21 | 1992-07-09 | Wade, Jonathan, Leslie | Adjuvants containing unsaturated lipid |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1165240A (en) * | 1980-07-09 | 1984-04-10 | The Procter & Gamble Company | Penetrating topical pharmaceutical compositions |
DE3045913A1 (en) * | 1980-12-05 | 1982-07-08 | Bayer Ag, 5090 Leverkusen | ANTIMYCOTIC AGENTS WITH HIGH ACTIVE SUBSTANCE RELEASE |
JPS57171912A (en) * | 1981-04-14 | 1982-10-22 | Sumitomo Chem Co Ltd | Cream |
-
1983
- 1983-07-01 DE DE19833323832 patent/DE3323832A1/en not_active Withdrawn
-
1984
- 1984-06-25 DE DE8484107249T patent/DE3483285D1/en not_active Expired - Fee Related
- 1984-06-25 AT AT84107249T patent/ATE56867T1/en not_active IP Right Cessation
- 1984-06-25 EP EP84107249A patent/EP0130516B1/en not_active Expired - Lifetime
- 1984-06-28 NZ NZ208693A patent/NZ208693A/en unknown
- 1984-06-28 FI FI842612A patent/FI842612A/en not_active Application Discontinuation
- 1984-06-29 KR KR1019840003755A patent/KR920006905B1/en not_active IP Right Cessation
- 1984-06-29 AU AU30023/84A patent/AU563760B2/en not_active Ceased
- 1984-06-30 JP JP59134137A patent/JPS6025921A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
FI842612A (en) | 1985-01-02 |
AU563760B2 (en) | 1987-07-23 |
AU3002384A (en) | 1985-01-03 |
EP0130516A3 (en) | 1986-07-30 |
KR920006905B1 (en) | 1992-08-22 |
EP0130516B1 (en) | 1990-09-26 |
FI842612A0 (en) | 1984-06-28 |
KR850000970A (en) | 1985-03-14 |
ATE56867T1 (en) | 1990-10-15 |
DE3483285D1 (en) | 1990-10-31 |
DE3323832A1 (en) | 1985-01-03 |
EP0130516A2 (en) | 1985-01-09 |
JPS6025921A (en) | 1985-02-08 |
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