GB2138287A - Topical compositions containing meclofenamic acid - Google Patents
Topical compositions containing meclofenamic acid Download PDFInfo
- Publication number
- GB2138287A GB2138287A GB08409412A GB8409412A GB2138287A GB 2138287 A GB2138287 A GB 2138287A GB 08409412 A GB08409412 A GB 08409412A GB 8409412 A GB8409412 A GB 8409412A GB 2138287 A GB2138287 A GB 2138287A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polyethylene glycol
- weight
- meclofenamic acid
- approximately
- acid
- 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.)
- Granted
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Classifications
-
- 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
- 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
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- 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
- A61K47/02—Inorganic compounds
-
- 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
-
- 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
- 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
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
A clear gel and a cream pharmaceutical composition for the treatment of inflammation containing meclofenamic acid are disclosed. The clear gel composition is prepared by dissolving meclofenamic acid or a salt thereof in polyethylene glycol monolaurate and polyethylene glycol lanolin oil and adding isopropyl alcohol with mixing and finally adding colloidal silicon dioxide with mixing. The cream composition is prepared by adding meclofenamic acid or the sodium or other salt thereof to an emulsion prepared by mixing a warm aqueous solution of sorbic acid with a melt of polyethylene glycol monostearate, glyceryl monostearate, caprylic and capric triglyceride and mineral oil.
Description
SPECIFICATION
Topical pharmaceutical compositions containing meclofenamic acid
This invention relates to topically active compositions containing meclofenamic acid in suitable topical vehicles. Also encompassed within the scope of this invention is the process for production of the topically active compositions.
Although not completely understood, the effects of nonsteroidal anti-inflammatory drugs (NSAID) is thought to be due to their interference with prostaglandin biosynthesis. This activity is likely to be related to the inhibition of cyclooxygenase and lipoxygenase in arachidonic acid metabolism.
Side effects, mostly associated with gastro-intestinal disturbances, have been reported with oral NSAID therapy. Topical application should be considered a valuable alternative mode of administration. Direct application to inflamed joints should result in appreciably lower systemic blood levels and hence better tolerance.
The non-steroidal anti-inflammatory drug, meclofenamic acid, its production and its use in the treatment of arthritis by oral administration are described in Unites States Patent Specification No. 3,313,848.
Meclofenamic acid is 2-[(2,6-dichloro-3-methyl-phenyl)amino] benzoic acid; it is also sometimes known as meclophenamic acid.
P. Schiantarelli et al, Arzneim-Forsch, Drug Res., 32 (1 ) and United States Patent Specification No.
4,185,100 describe the use of combinations containing topically active anti-inflammatory corticosteroid and non-steroidal anti-inflammatory agents for the topical treatment of cutaneous disorders.
Meclofenamic acid is virtually water-insoluble and, therefore, a hydroalcoholic gel could not be formulated at the desired concentration of drug. The drug is also insoluble in glycerin, isopropyl myristate and mineral oil. The use of the latter two solvents is described in United States Patent Specification No.4,185,100. Its solubility in propylene glycol, ethyl alcohol and linoleic acid is somewhat less than 5%.
According to one aspect of the present invention, there is provided a stable non-aqueous clear gel composition comprising a polyethylene glycol ester, a water-soluble lanolin oil, a thickening agent, an alcohol, and from 3 to 10% by weight, based on the weight of the composition, of meclofenamic acid or a salt thereof.
This aspect of the present invention is based on the discovery that meclofenamic acid is soluble in the following water-miscible solvents to an extent of at best 5% at room temperature and more with the aid of heating up to 50"C:- polyethylene glycol 400,
polyethylene glycol -8 monolaurate,
polyethylene glycol glucose ethers also referred to as [PEG Glucose Ethers (Glucam-P 10, P-20)],
polethylene glycol - 75 lanolin oil also referred to as (Lantrol AWS), and
polypropylene (PPG)-5-Ceteth-10 Phosphate, also referred to as (Crodafos SG).
Meclofenamic acid was found to have a highly favourable octanol/water partition coefficient and we have now discovered novel gel and cream formulations which provide maximal topical activity for meclofenamic acid.
Broadly speaking the gel formulation is a clear gel of meclofenamic acid in a co-solvent system of a polyethylene glycol ester, water-soluble lanolin oil, an alcohol and a thickening agent.
The polyethylene glycol ester is preferably selected from polyethylene glycol mono- and dilaurate and polyethylene glycol mono- and dioleate. The more preferred polyethylene glycol esters are polyethylene glycol-8 monolaurate, polethylene glycol -8 and -8 dilaurate, polyethylene glycol -8 monoleate and polyethylene glycol -8 dioleate. The most preferred polyethylene glycol ester is polyethylene glycol 400 monolaurate.
The preferred water-soluble lanolin oil is a polyethylene glycol lanolin oil and the most preferred is polyethylene glycol -75 lanolin oil.
The preferred thickening agent is colloidal silicon dioxide.
The alcohol is preferably selected from those containing 3 or 4 carbon atoms, i.e. propyl, isopropyl, butyl, sec-butyl and tert-butyi. The most preferred is isopropyl alcohol.
The meclofenamic acid is present in the range of 3 to 10% by weight and preferably approximately 5% by weight. The acid may be in free acid form, or as a salt, preferably the sodium salt.
The polyethylene glycol ester is present preferably in the range from 30 to 60% by weight and more preferably approximately 50% by weight. The water-soluble lanolin is present preferably in the range of up to 20% by weight and more preferably approximately 10% by weight. The thickening agent is present preferably from 5 to 10% by weight and more preferably approximately 5% by weight. Sufficient alcohol is used to bring the total constituents to 100%.
The gel formulation may be prepared, in accordance with another aspect of the present invention, by dissolving meclofenamic acid in a heated and stirred solution of polyethylene glycol ester and water-soluble lanolin oil; allowing the solution to cool and adding the alcohol with continued stirring until the solution cools to room temperature; and adding a thickening agent with high shear stirring; and optionally finally adding sufficient alcohol to make a clear gel.
According to a further aspect of the present invention, there is provided a cream composition comprising polyethylene glycol ester, a glyceryl or propylene monostearate, a triglyceride, a mineral oil, a preservative, and from 3 to 10% by weight, based on the composition, of meclofenamic acid or a salt thereof.
The meclofenamic acid may be as the free acid or as a salt thereof, e.g. the sodium salt thereof.
The polyethylene glycol ester is preferably selected from polyethylene glycol monostearate and polyethylene glycol monolaurate. The more preferred polyethylene glycol esters are polyethylene glycol 40, 45,50,75 and -6-32 monostearate and polyethylene glycol -75 and -150 monolaurate. The most preferred polyethylene glycol ester is polyethylene glycol -6-32 monostearate.
The triglyceride is preferably selected from capryiic/capric triglyceride, caprylic/capric/stearic triglyceride and hydrogenated palm oil triglyceride. The most preferred triglyceride is caprylic/capric triglyceride.
The preservative is preferably selected from sorbic acid and benzoic acid and a combination of methylparaben and propylparaben. The most preferred preservative is sorbic acid.
The meclofenamic acid or the sodium or other salt thereof is present in the range of from 3 to 10% by weight, preferably approximately 5% by weight. Meclofenamic acid itself is the preferred form of the active ingredient.
The polyethylene glycol ester and glyceryl or propylene monostearate are each preferably present in the range from 5 to 12% by weight and more preferably approximately 9% by weight The triglyceride is preferably present in the range from 3 to 10% by weight and more preferably approximately 5% by weight.
The mineral oil is preferably present in the range from 5 to 10% by weight and more preferably approximately 8% by weight.
The preservative is present in sufficient amount to function as a preservative. Usually approximately 0.1% by weight is sufficient
The cream formulation may be prepared, in accordance with a yet further aspect of the present invention, by adding meclofenamic acid or the sodium or other salt thereof to an emulsion prepared by mixing a warm aqueous solution of preservative with a melt of a polyethylene glycol ester, glyceryl or propylene monostearate, a triglyceride and mineral oil. The pH is adjusted to the range 4.5 to 5 and the cream homogenized and cooled to room temperature.
In order to further illustrate the practice of the present invention, the following examples are included.
Example 1
A clear gel containing 5% meclofenamic acid was prepared from the following ingredients: Ingredients 1000.009
5.0 1. meclofenamic acid 50.009 50.0 2. PEG-8 laurate (PEG 400
monolaurate) q.s. or 500.00g 10.0 3. PEG-75 lanolin oil
(Lantrol AWS) q.s. or 100.009
5.0 4. silicon dioxide
colloidal NF q.s. or 50.009 30.0 5. isopropyl alcohol
USP q.s. to 1000.00g The PEG-8 laurate (Polyethylene glycol 400 monolaurate) and PEG-75 lanolin oil (Lantrol AWS) were heated to 90"C. To the resulting solution was added meclofenamic acid with heating to maintain a temperature of 90"C and with stirring until the meclofenamic acid dissolved. The solution was allowed to cool to 40"C, and 300g. of isopropyl alcohol were added. Stirring was continued until the solution cooled to room temperature. Colloidal silicon dioxide NP was added to the solution with high shear mixing for 10 minutes. Sufficient isopropyl alcohol was added to make 10009 and mixed until a uniform, clear, pale yellow gel containing 5% meclofenamic acid was obtained.
Example 2
A gel containing 5% sodium meclofenamate was prepared according to the process of EXAMPLE 1 by replacing the meclofenamic acid with 50.00g of sodium meclofenamate.
Example3
Example 3
A cream containing 5% meclofenamic acid was prepared from the following ingredients: Ingredients 1000.00g 5.00 1. meclofenamic acid 50.009
9.00 2. polyethylene glycol
-6-32 monostearate 90.009
9.00 3. glyceryl monostearate 90.009
5.00 4. caprylic/capric
triglyceride 50.009 8.00 5. mineral oil 80.009 0.1 6. sorbic acid
(preservative) 1g - 7. triethanolamine q.s. to
pH 4.5 - 5.0
- 8. water, distilled
q.s. to 1000.009
The polyethylene glycol -6-32 monostearate, glyceryl monostearate, caprylic/caprictriglyceride and
mineral oil were combined in a suitable jacketed tank and melted by heating to 60"C.
An aqueous solution of sorbic acid was prepared in a jacketed tank equipped with a paddle mixer by dissolving the sorbic acid with mixing in the minimum amount of water preheated to 60"C. The aqueous solution of sorbic acid was added with agitation to the melted polyethylene glycol -6-32 monostearate, glyceryl monostearate, caprylic/capric triglyceride and mineral oil to form an emulsion. The meclofenamic acid was added to the emulsion with continued agitation and while maintaining the temperature at 60"C.
The pH of the resulting cream was adjusted to 4.5 - 5.0 with the addition of triethanolamine and the cream was circulated through an in-line homogenizer and allowed to cool to room temperature.
Example 4
A cream containing 5% sodium meclofenamate was prepared according to the procedure of EXAMPLE 3 by replacing the meclofenamic acid with 50.009 of sodium meclofenamate.
Claims (13)
1. A stable non-aqueous clear gel composition comprising a polyethylene glycol ester, a water-soluble lanolin oil, a thickening agent, an alcohol, and from 3 to 10% by weight, based on the weight of the composition, of meclofenamic acid or a salt thereof.
2. A gel composition according to Claim 1, wherein the polyethylene glycol ester is selected from polyethylene glycol mono- and dilaurate and polyethylene glycol mono- and dioleate; the water-soluble lanolin oil is a polyethylene glycol lanolin oil; the thickening agent is colloidal silicon dioxide; and the alcohol contains 3 to 4 carbon atoms.
3. A gel composition according to Claim 2, wherein the polyethylene glycol ester is selected from polyethylene glycol -8 monolaurate, polyethylene glycol -4 and -8 dilaurate, polyethylene glycol -8 monoleate and polyethylene glycol -8 dioleate; and the alcohol is selected from propyl, isopropyl, butyl, sec-butyl and tert-butyl alcohols.
4. A gel composition according to Claim 1,2 or 3, comprising from 3 to 10% by weight of meclofenamic acid, from 30 to 60% by weight of a polyethylene glycol ester, up to 20% by weight of a water-soluble lanolin oil, from 5 to 10% by weight of a thickening agent, and sufficient alcohol to constitute the balance of the composition.
5. A gel composition according to Claim 4, comprising approximately 5% by weight of meclofenamic acid, having approximately 50% by weight of polyethylene glycol -8 monolaurate, aproximately 10% by weight of polyethylene glycol -75 lanolin oil, approximately 5% by weight of colloidal silicon dioxide, and approximately 30% by weight of isopropyl alcohol.
6. A process for producing a gel according to Claim 1, which comprises the steps of:
(a) dissolving meclofenamic acid in a heated and stirred solution of the polyethylene glycol ester and the
water-soluble lanolin oil;
(b) adding the alcohol and cooling to room temperature;
(c) adding the thickening agent with high shear stirring until a clear gel is obtained.
7. A cream composition comprising polyethylene glycol ester, a glyceryl or propylene monostearate, a triglyceride, a mineral oil, a preservative, and from 3 to 10% by weight, based on the composition, of meclofenamic acid or a salt thereof.
8. A cream composition according to Claim 7, wherein the polyethylene glycol is selected from polyethylene glycol monostearate and polyethylene glycol monolaurate; the triglyceride is selected from caprylic/capric triglyceride, caprylic/capric/stearic triglyceride and hydrogenated palm oil triglyceride; and the preservative is selected from sorbic acid and benzoic acid and a combination of methyiparaben and propylparaben.
9. A cream composition according to Claim 8, wherein the polyethylene glycol ester is selected from polyethylene glycol 40,45,50,75 and -6-32 monostearate and polyethylene glycol -75 and -150 monolaurate.
10. A cream composition according to Claim 7, 8 or 9, comprising from 3 to 10% by weight of meclofenamic acid, from 5 to 12% by weight of polyethylene glycol ester, from 5 to 12% by weight of glyceryl or propylene monostearate, from 3 to 10% by weight of triglyceride, from 5 to 10% by weight of mineral oil and approximately 0. 1% by weight of preservative.
11. A cream composition according to Claim 10, comprising approximately 5% by weight of meclofenamic acid, approximately 9% by weight of polyethylene glycol -6-32 monostearate, approximately 9% by weight of glyceryl monostearate, approximately 5% by weight of caprylic/capric triglyceride, approximately 8% by weight of mineral oil, and sorbic acid preservative, the pH of the composition being adjusted from 4.5 to 5.0
12. A process for producing a cream according to Claim 7, which comprises the steps of:
(a) melting a mixture of polyethylene glycol ester, glyceryl or propylene monostearate, a triglyceride and
mineral oil;
(b) adding an aqueous solution of the preservative with mixing to form an emulsion;
(c) adding meclofenamic acid to the emulsion with agitation; and
(d) adjusting the pH to 4.5 to 5.0.
13. A composition according to any one of Claims 1 to 5 and 7 to 11, wherein the meclofenamic acid is in the form of its free acid or is in the form of the sodium salt.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48597383A | 1983-04-18 | 1983-04-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2138287A true GB2138287A (en) | 1984-10-24 |
| GB2138287B GB2138287B (en) | 1986-03-05 |
Family
ID=23930121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08409412A Expired GB2138287B (en) | 1983-04-18 | 1984-04-11 | Topical compositions containing meclofenamic acid |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU560035B2 (en) |
| BE (1) | BE899366A (en) |
| CA (1) | CA1229554A (en) |
| DE (1) | DE3414377A1 (en) |
| FR (1) | FR2544198B1 (en) |
| GB (1) | GB2138287B (en) |
| NL (1) | NL8400933A (en) |
| NZ (1) | NZ207874A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6322518A (en) * | 1986-07-02 | 1988-01-30 | ア．メナリニ・エツセ．ア．エツセ | Gel-like pharmaceutical composition containig n-(2,6-dichloro-m-tolyl)anthranilic acid |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0318488A4 (en) * | 1986-08-18 | 1990-02-26 | Biota Scient Management | Stimulation of angiogenesis and promotion of endothelialisation. |
| US5332577A (en) * | 1988-12-27 | 1994-07-26 | Dermamed | Transdermal administration to humans and animals |
| US5241925A (en) * | 1988-12-27 | 1993-09-07 | Dermamed | Apparatus and techniques for administering veterinary medicaments |
| US5324521A (en) * | 1989-12-18 | 1994-06-28 | Dermamed | Systems for transdermal administration of medicaments |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1550139A (en) * | 1975-07-04 | 1979-08-08 | Gaba Ag | Anti-inflammatory compositions for oral application |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4185100A (en) * | 1976-05-13 | 1980-01-22 | Johnson & Johnson | Topical anti-inflammatory drug therapy |
| NL175882C (en) * | 1977-03-28 | Procter & Gamble | PHARMACEUTICAL PREPARATION CONTAINING AN ANTI-INFLAMMATORY COMPOUND. | |
| JPS5826815A (en) * | 1981-08-10 | 1983-02-17 | Ikeda Mohandou:Kk | Nonsteroid antiphlogistic ointment and its preparation |
-
1984
- 1984-02-23 CA CA000448165A patent/CA1229554A/en not_active Expired
- 1984-02-29 AU AU25148/84A patent/AU560035B2/en not_active Ceased
- 1984-03-22 FR FR8404440A patent/FR2544198B1/en not_active Expired
- 1984-03-23 NL NL8400933A patent/NL8400933A/en not_active Application Discontinuation
- 1984-04-06 BE BE6/47951A patent/BE899366A/en not_active IP Right Cessation
- 1984-04-11 GB GB08409412A patent/GB2138287B/en not_active Expired
- 1984-04-16 DE DE19843414377 patent/DE3414377A1/en not_active Withdrawn
- 1984-04-17 NZ NZ20787484A patent/NZ207874A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1550139A (en) * | 1975-07-04 | 1979-08-08 | Gaba Ag | Anti-inflammatory compositions for oral application |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6322518A (en) * | 1986-07-02 | 1988-01-30 | ア．メナリニ・エツセ．ア．エツセ | Gel-like pharmaceutical composition containig n-(2,6-dichloro-m-tolyl)anthranilic acid |
| EP0252033A3 (en) * | 1986-07-02 | 1988-03-30 | A. Menarini S.A.S. | Utilization of the "gel" pharmaceutical form containing n-(2.6-dichloro-m-tolil)-anthranilic acid (mechlophenamic acid) utilizable in therapy for topical usage |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ207874A (en) | 1987-01-23 |
| AU560035B2 (en) | 1987-03-26 |
| CA1229554A (en) | 1987-11-24 |
| BE899366A (en) | 1984-10-08 |
| FR2544198A1 (en) | 1984-10-19 |
| GB2138287B (en) | 1986-03-05 |
| FR2544198B1 (en) | 1987-11-20 |
| NL8400933A (en) | 1984-11-16 |
| AU2514884A (en) | 1984-10-25 |
| DE3414377A1 (en) | 1984-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |