DK143537B - PROCEDURE FOR THE PREPARATION OF A STABLE WATER-CLEAR GEL-SHAPE OR LOTION CONTAINING A STEROID AND NEOMYCIN SALT - Google Patents
PROCEDURE FOR THE PREPARATION OF A STABLE WATER-CLEAR GEL-SHAPE OR LOTION CONTAINING A STEROID AND NEOMYCIN SALT Download PDFInfo
- Publication number
- DK143537B DK143537B DK147575A DK147575A DK143537B DK 143537 B DK143537 B DK 143537B DK 147575 A DK147575 A DK 147575A DK 147575 A DK147575 A DK 147575A DK 143537 B DK143537 B DK 143537B
- Authority
- DK
- Denmark
- Prior art keywords
- weight
- steroid
- approx
- neomycin
- benzoate
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
-
- 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
Description
143537 i o143537 in o
Den foreliggende opfindelse angår en fremgangsmåde til fremstilling af en stabil, vandig klar, gelformig salve eller lotion indeholdende et steroid valgt blandt fluocinolon-acetonid og $-methason-17-benzoat og et nearay-The present invention relates to a process for the preparation of a stable, aqueous clear, gel-like ointment or lotion containing a steroid selected from fluocinolone-acetonide and β-methasone-17-benzoate;
CC
cinsalt valgt blandt neomycinsulfat og neomycinchlorid, ved hvilken steroidet opløses i et glycolopløsningsmiddel og en alkohol.cine salt selected from neomycin sulfate and neomycin chloride, wherein the steroid is dissolved in a glycol solvent and an alcohol.
Anvendelse af topisk aktivt steroid til behandling af lokale inflammatoriske tilstande er en anerkendt terapeu-tisk fremgangsmåde. Steroidet suspenderes eller opløses sædvanligvis i ét grundlag til anvendelse på et område med inflammation. I tilfælde hvor inflammationen er kompliceret som følge af bakterieinfektioner, kombineres et topisk aktivt antimikrobielt stof med steroidet til bekæmpelse af 1-* bakterieinfektioner.Use of topically active steroid for the treatment of local inflammatory conditions is a recognized therapeutic approach. The steroid is usually suspended or dissolved in one basis for use in an area of inflammation. In cases where the inflammation is complicated by bacterial infections, a topically active antimicrobial substance is combined with the steroid to control 1- * bacterial infections.
S-Methason-17-benzoat er et nylig opdaget topisk steroid. Fremstillingen af denne forbindelse er beskrevet i britisk patentskrift nr. 1.191.965, japansk patentskrift nr. 983.947, svensk patentskrift nr. 330.538, sydafrikansk 20 patentskrift nr. 681.303 og fransk patentskrift nr. M-8027.S-Methasone-17-benzoate is a recently discovered topical steroid. The preparation of this compound is disclosed in British Patent No. 1,191,965, Japanese Patent No. 983,947, Swedish Patent No. 330,538, South African Patent No. 681,303 and French Patent No. M-8027.
Med henblik på opnåelse af maksimal topisk virkning af steroidet inkorporeres dette i salvegrundlag, jfr. britisk patentskrift nr. 1.316.556 og USA-patentskrift nr.In order to achieve maximum topical effect of the steroid, this is incorporated into ointment basis, cf. British Patent No. 1,316,556 and U.S. Pat.
3.749.773.3749773.
25 Dette grundlag indeholder ethanol, propylenglycol, geleret ved inkorporering af en carboxyvinylpolymer neutraliseret med en amin. Dette danner en klar gel med steroidet.This basis contains ethanol, propylene glycol, gelled by incorporation of a carboxyvinyl polymer neutralized with an amine. This forms a clear gel with the steroid.
Det kan påføres topisk, og tillader maksimal absorption af steroidet. Når der i et sådant grundlag indeholdende ste-30 roidet inkorporeres et antimikrobielt stof, som f.eks. neo-mycinsulfat, dannes der imidlertid et koaguleret bundfald.It can be applied topically, allowing maximum absorption of the steroid. When in such a base containing the steroid an antimicrobial agent such as e.g. neo-mycine sulfate, however, a coagulated precipitate is formed.
Dette er naturligvis uønsket. Endvidere har det ved mikrobiologiske forsøg med agarplade-standardmetoden vist sig, at der ikke er noget neomycinsulfat til stede til tilveje-35 bringelse af den ønskede antimikrobielle aktivitet.Of course, this is undesirable. Furthermore, in microbiological experiments with the standard agar plate method, it has been found that no neomycin sulfate is present to provide the desired antimicrobial activity.
Fra beskrivelsen 'til USA patent nr. 3.529.060 er det endvidere kendt at inkorporere et antiinflammatorisk steroid, S-methason-17-benzoat, og neomycinsulfat i en salFurther, from U.S. Pat. No. 3,529,060, it is known to incorporate an anti-inflammatory steroid, S-methasone-17-benzoate, and neomycin sulfate in a sal
OISLAND
143537 2 ve, som indeholder et traditionelt farmaceutisk grundlag fremstillet ud fra lanolin og paraffin, og som efterlader et fedtet lag på hudens overflade.Contains a traditional pharmaceutical basis made from lanolin and paraffin, which leaves a greasy layer on the skin's surface.
Det har vist sig, at der kan fremstilles en stabil, 5 vandig klar, gelformig salve eller lotion indeholdende et steroid valgt blandt fluocinolon-acetonid og |3-bethason-17--benzoat og et neomycinsalt valgt blandt neomycinsulfat og neomycinchlorid, og fremgangsmåden ifølge opfindelsen er ejendommelig ved, at 10 a) steroidet opløses i en blanding af fra ca. 20 til ca. 60 vægtprocent glycolopløsningsmiddel valgt blandt glycerol, ethylenglycol, propylen-glycol og butylenglycol, og fra ca. 3 til ca.It has been found that a stable aqueous clear gel ointment or lotion containing a steroid selected from fluocinolone acetonide and β-bethasone 17-benzoate and a neomycin salt selected from neomycin sulfate and neomycin chloride can be prepared, and the method of The invention is characterized in that the 10 a) dissolves the steroid in a mixture of from ca. 20 to approx. 60% by weight glycol solvent selected from glycerol, ethylene glycol, propylene glycol and butylene glycol, and from ca. 3 to approx.
25 vægtprocent alkohol valgt blandt ethylalko-15 hol og isopropylalkohol, b) til den under a) dannede opløsning sættes fra ca. 0,5 til ca. 5 vægtprocent cellulose valgt blandt hydroxypropylcellulose og hydroxypropyl-methylcellulose, 20 c) til den under b) dannede blanding sættes en van dig opløsning af neomycinsaltet, hvorpå d) der tilsættes tilstrækkeligt natriumchlorid til dannelse af en klar gel, og e) pH-vsrdien om nødvendigt indstilles til 4-5, hvor-2 5 hos de ovenfor angivne vægtprocenter er på basis af den samlede vægt af den færdige salve eller lotion.25% by weight of alcohol selected from ethyl alcohol and isopropyl alcohol; b) to the solution formed under a) is added from ca. 0.5 to approx. 5% by weight of cellulose selected from hydroxypropylcellulose and hydroxypropylmethylcellulose, c) to the mixture formed under b), add an aqueous solution of the neomycin salt, d) add sufficient sodium chloride to form a clear gel, and e) the pH need to be adjusted to 4-5, where -25 of the percentages given above are based on the total weight of the final ointment or lotion.
Den ved fremgangsmåden ifølge opfindelsen fremstillede klare, gelformige salve eller lotion har en helt anden 30 karakter end de kendte salver. Den klare, gelformige salve eller lotion fremstillet ved fremgangsmåden ifølge opfindelsen er således transparent og let at fordele på huden, og den efterlader ingen uønskede fedtede rester på huden.The clear, gel-shaped ointment or lotion prepared by the process of the invention has a completely different character from the known ointments. Thus, the clear, gel-like ointment or lotion prepared by the method of the invention is transparent and easy to disperse on the skin, leaving no unwanted greasy residue on the skin.
Den er derfor en kosmetisk elegant og for brugeren langt 35 mere attraktiv form end de kendte salver.It is therefore a cosmetically elegant and for the user far 35 more attractive shape than the known ointments.
Natriumchlorid sættes til suspensionen til tilvejebringelse af en klar gel.Sodium chloride is added to the suspension to provide a clear gel.
33
OISLAND
143537143537
En særlig fordelagtig udførelsesform for fremgangsmåden ifølge opfindelsen består i, at a) 0,025 vægtprocent |3-methason-17-benzoat oplø- 5 ses i ca. 15 vægtprocent ethanol og 35 vægtpro cent propylenglycol, b) til opløsningen af steroidet sættes ca. 1,5 vægtprocent hydroxypropylmethylcellulose med en viskositet fra ca. 80 til ca. 120.000 cps, 10 c) i vand opløses ca. 0,35% neomycinbase i form af tf,5 vægtprocent neomycinsulfat i en opløsning indeholdende 1 vægtprocent polyethylenglycol 4000 som fortykkelsesmiddel og 40 vægtprocent vand, og opløsningen sættes til b), hvorpå 15 d) der tilsættes en tilstrækkelig mængde natrium- chlorid til opløsning af neomycinsulfat, og e) den fremkomne blandings pH-værdi indstilles til 4,0-5,0, hvorhos de ovenfor angivne vægtprocenter er på basis af den 20 samlede vægt af den færdige salve eller lotion.A particularly advantageous embodiment of the process according to the invention consists in that a) 0.025 wt.% Of 3-methasone-17-benzoate is dissolved in ca. 15% by weight ethanol and 35% by weight propylene glycol; b) to the solution of the steroid is added approx. 1.5 wt% hydroxypropylmethyl cellulose with a viscosity of approx. 80 to approx. 120,000 cps, 10 c) dissolve in water approx. 0.35% neomycin base in the form of tf, 5% by weight of neomycin sulfate in a solution containing 1% by weight of polyethylene glycol 4000 as a thickening agent and 40% by weight of water, and the solution is added to b), to which 15 d) a sufficient amount of sodium chloride is added to dissolve and e) adjust the pH of the resulting mixture to 4.0-5.0, where the percentages given above are based on the total weight of the final ointment or lotion.
Ved denne udførelsesform fremstilles præparater, som har særlig gode kosmetiske egenskaber med hensyn til klarhed, konsistens og hudforenelighed.In this embodiment, compositions having particularly good cosmetic properties in terms of clarity, consistency and skin compatibility are prepared.
Ved undersøgelse af præparatet fremstillet ved frem- 25 gangsmåden ifølge opfindelsen viser det sig, at neomycinet ikke er inaktiveret, og steroidet er desuden helt disponibelt.Upon examination of the preparation prepared by the method of the invention, it appears that the neomycin is not inactivated and the steroid is also completely available.
Til forhindring af oxidation kan der til præparatet eventuelt sættes en lille mængde, f.eks. o,l vægtprocent, egnet antioxidant som f.eks. natriumbisulfit, og chelaterings-30 midler.To prevent oxidation, a small amount may be added to the composition, e.g. o, 1% by weight, suitable antioxidant, e.g. sodium bisulfite, and chelating agents.
Den fremkomne gel er hovedsagelig klar og har en i alt væsentligt ensartet konsistens og er endvidere karakteriseret ved, at den er selv-konserverende, idet det ikke er nødvendigt at tilsætte de gængse konserveringsmidler, 35 som f.eks. parabener.The resulting gel is essentially clear and has a substantially uniform consistency and is further characterized in that it is self-preserving, since it is not necessary to add the usual preservatives, such as e.g. parabens.
Fremgangsmåden ifølge opfindelsen illustreres nærmere i følgende eksempler.The method according to the invention is further illustrated in the following examples.
' U3537 4 O Eksempel 1Example 1
Der fremstilles en klar gel ud fra følgende bestanddele :A clear gel is prepared from the following ingredients:
Indhold i 5 vægtprocent_ Bestanddele_1000,00 g 0,025 1. p-methason-17-benzoat 0,2625 gx 0,35 2. neomycinsulfat USP, mængden bestem-Content in 5% by weight_ Ingredients_1000.00 g 0.025 1. p-methasone-17-benzoate 0.2625 gx 0.35 2. neomycin sulfate USP, the amount determined
Cbase- mes efter analyse for den rene ba- form) seform, ca. 5,00 g 3. hydroxypropylmethylcellulose 15,00 g 4. propylenglycol USP 350,00 g 5. ethvlalkohol USP 166,67 g xx 6. polyethylenglycol 4000 USP 10,00 g 7. dinatriumsaltet af ethylendiamin- tetraeddikesyre USP 1,00 g ^ 8. natriumbisulfit USP 1,00 g 9. natriumclorid USP granulat 10,00 g 10. saltsyre 1 N ca. 3,00 ml 11. vand, renset USP til 1000,00 g x 5% overskud til oparbejdningstab.Cbase after analysis for the pure base form, ca. 5.00 g 3. hydroxypropylmethyl cellulose 15.00 g 4. propylene glycol USP 350.00 g 5. ethyl alcohol USP 166.67 g xx 6. polyethylene glycol 4000 USP 10.00 g 7. the disodium salt of ethylene diamine tetraacetic acid USP 1.00 g ^ 8. sodium bisulfite USP 1.00 g 9. sodium chloride USP granulate 10.00 g 10. hydrochloric acid 1 N approx. 3.00 ml 11. water, purified USP to 1000.00 g x 5% excess for work-up losses.
20 xx 11% overskud til fremstillingstab.20 xx 11% profit for manufacturing losses.
Gelen fremstilles ved opløsning af β-methason-17-ben- zoat i alkoholen samt propylenglycol under anvendelse af et egnet blandingsapparat. Til denne blanding sættes hydroxy-25 propylmethylcellulose, og der omrøres, indtil methylcellulo-sen er vædet.The gel is prepared by dissolving β-methasone-17-benzoate in the alcohol as well as propylene glycol using a suitable mixing apparatus. To this mixture is added hydroxypropyl methyl cellulose and stirred until the methyl cellulose is wet.
I en separat beholder blandes neomycinsulfat sammen med polyethylenglycol 4000, dinatriumsaltet af ethylen- diamintetraeddikesyre og natriumbisulfat og ca. 400 g vand.In a separate container, neomycin sulfate is mixed with polyethylene glycol 4000, the disodium salt of ethylene diamine tetraacetic acid and sodium bisulfate, and ca. 400 g of water.
30 Når opløsningen er komplet, sættes den til p-methason-17-ben-zoat-opløsningen. Natriumchloridet opløst i ca. 40 g. vand sættes til den fremkomne blanding. Under omrøring indstilles pH-værdien med saltsyre til 4,0-5,0, og der tilsættes tilstrækkelig vand til opnåelse af 1000 g. Der fås en klar gel 35 indeholdende 0,025 vægtprocent β-methason-17-benzoat og 0,35 vægtprocent neomycin.When complete, the solution is added to the p-methasone-17-benzoate solution. The sodium chloride dissolved in ca. 40 g of water are added to the resulting mixture. With stirring, adjust the pH with hydrochloric acid to 4.0-5.0 and add enough water to obtain 1000 g. A clear gel 35 containing 0.025% by weight of β-methasone-17-benzoate and 0.35% by weight of neomycin is obtained. .
5 143537 O Eksempel 2Example 2
Der gås frem som beskrevet 1 eksempel 1, idet β-me-thason-17-benzoat erstattes med fluocinolon-acetonid, og der fås ligeledes en klar gel.Proceed as described in Example 1, replacing β-methasone-17-benzoate with fluocinolone-acetonide, and a clear gel is also obtained.
55
Eksempel 3Example 3
Den ifølge eksempel 1 fremstillede gels biologiske aktivitet sammenlignes med en vandig opløsning af neomycin-sulfat. Den anvendte forsøgsmetode er agarplademetoden, idet ]_q der anvendes S. aureus ATCC 6538P som forsøgsorganisme. Følgende resultater opnås: Hæmnings- Neomycin- Hæmningszone base zoneThe biological activity of the gel of Example 1 is compared to an aqueous solution of neomycin sulfate. The test method used is the agar plate method, using S. aureus ATCC 6538P as the test organism. The following results are obtained: Inhibition Neomycin Inhibition zone base zone
Præparat (mm) (mcg/ml) (mm) 8 15---Preparation (mm) (mcg / ml) (mm) 8 15 ---
Præparat ifølge eksempel 1 8,6 3.500 8,0Preparation of Example 1 8.6 3,500 8.0
Placebo i.z. xx 3.000 7,8 x gennemsnit af to observationer.Placebo i.z. xx 3,000 7.8 x average of two observations.
20 xx ingen zone.20 xx no zone.
Det i ovennævnte forsøg anvendte placebo indeholder alle ingredienserne undtagen neomycin og p-methason-17-ben- zoat. Ovenstående resultater viser, at ved anvendelse af den her omhandlede fremgangsmåde bibeholder neomycinsulfatet 25 dets antimikrobielle aktivitet, idet hæmningszonen nærmer sig hæmningszonen for en vandig opløsning af neomycinsulfat.The placebo used in the above experiment contains all the ingredients except neomycin and p-methasone-17 benzoate. The above results show that, using the method of the present invention, the neomycin sulfate 25 retains its antimicrobial activity as the inhibition zone approaches the inhibition zone for an aqueous solution of neomycin sulfate.
Eksempel 4 2Q Til illustration af præparatets kliniske effektivi tet foretages dobbeltblindforsøg med 10 normale voksne personer. Præparat A indeholder 8-methason-17-benzoat i et kendt gelpræparat, og præparat B er fremstillet ved fremgangsmåden ifølge eksempel 1.Example 4 2Q To illustrate the clinical efficacy of the preparation, double-blind trials are performed with 10 normal adult subjects. Preparation A contains 8-methasone-17-benzoate in a known gel preparation and Preparation B is prepared by the method of Example 1.
^ Præparaterne A og B påføres begge underarme på 10 patienter på vilkårlig måde, idet der foretages tre påføringer af hvert præparat på hver patient.^ Compositions A and B are both applied to the forearms of 10 patients at random, with three applications of each preparation to each patient.
143537 6143537 6
OISLAND
Armene tildækkes derpå i 20 timer, og områderne bedømmes én time og otte timer efter fjernelse af dæklaget.The arms are then covered for 20 hours, and the areas are assessed one hour and eight hours after removal of the cover layer.
Blegning af et område, dvs. vasokonstriktion, betegnes som positiv, dvs. der er sket en absorption af ste-5 roidet. De opnåede resultater er som følger:Bleaching of an area, i.e. vasoconstriction, is termed positive, i.e. an absorption of the steroid has occurred. The results obtained are as follows:
Samlet antal Antal med posi- påføringer tiv blegning 1 time 8 timerTotal number Number of positives for bleaching 1 hour 8 hours
Gel A 30 23 27 10 Gel B 30 19 24Gel A 30 23 27 10 Gel B 30 19 24
Af ovenstående resultater fremgår det klart, at neomycinet i det ved fremgangsmåden ifølge opfindelsen fremstillede præparat ikke inaktiverer eller forstyrrer absorp-15 tionen af steroidet.From the above results, it is clear that the neomycin in the composition of the present invention does not inactivate or interfere with the absorption of the steroid.
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46025474A | 1974-04-11 | 1974-04-11 | |
| US46025474 | 1974-04-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK147575A DK147575A (en) | 1975-10-12 |
| DK143537B true DK143537B (en) | 1981-09-07 |
| DK143537C DK143537C (en) | 1982-02-01 |
Family
ID=23827960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK147575A DK143537C (en) | 1974-04-11 | 1975-04-07 | PROCEDURE FOR PREPARING A STABLE, WATER-CLEAR, GEL-shaped SALVE OR LOTION CONTAINING A STEROID AND NEOMYCIN SALT |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS535729B2 (en) |
| AU (1) | AU7776275A (en) |
| CA (1) | CA1049409A (en) |
| DE (2) | DE2504615C3 (en) |
| DK (1) | DK143537C (en) |
| FR (1) | FR2267107B1 (en) |
| GB (1) | GB1455552A (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4604384A (en) * | 1982-06-24 | 1986-08-05 | Smith Robert A | Pharmaceutical gel composition |
| US4489070A (en) * | 1983-05-13 | 1984-12-18 | Schering Corporation | Betamethasone dipropionate cream |
| DE3333240A1 (en) * | 1983-09-12 | 1985-03-28 | Schering AG, 1000 Berlin und 4709 Bergkamen | MEDIUM FOR TRANSDERMAL APPLICATION OF MEDICINAL PRODUCTS |
| AU592065B2 (en) * | 1984-10-09 | 1990-01-04 | Dow Chemical Company, The | Sustained release dosage form based on highly plasticized cellulose ether gels |
| FR2588189B1 (en) * | 1985-10-03 | 1988-12-02 | Merck Sharp & Dohme | LIQUID-GEL PHASE TRANSITION PHARMACEUTICAL COMPOSITION |
| DE3614095A1 (en) * | 1986-04-25 | 1987-10-29 | Goedecke Ag | OXYALKYLCELLULOSE CONTAINING GEL PREPARATION |
| DE59009378D1 (en) * | 1990-04-05 | 1995-08-10 | Sagitta Arzneimittel Gmbh | Pharmaceutical composition containing diclofenac sodium for topical use. |
| AU2000268609A1 (en) * | 2000-09-14 | 2002-03-26 | Robert Theiler | Intraarticular agent for the treatment of osteoarthritis |
| PL2366408T3 (en) * | 2010-03-01 | 2013-01-31 | Salvat Lab Sa | Aqueous clear solutions of fluocinolone acetonide for treatment of otic inflammation |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1017746B (en) * | 1954-02-09 | 1957-10-17 | Upjohn Co | Process for the preparation of free flowing, non-settling therapeutically effective suspensions |
| US3485915A (en) * | 1966-04-22 | 1969-12-23 | Revlon | Thickened hydroxypropyl cellulose compositions |
| DE2015300A1 (en) * | 1969-04-01 | 1970-10-29 | Syntex Corp., Panania;PM | topical anti-inflammatory preparations and methods of their use |
| DK135267A (en) * | 1971-02-25 |
-
1975
- 1975-01-30 AU AU77762/75A patent/AU7776275A/en not_active Expired
- 1975-02-04 DE DE19752504615 patent/DE2504615C3/en not_active Expired
- 1975-03-20 JP JP3426675A patent/JPS535729B2/ja not_active Expired
- 1975-03-21 GB GB955575A patent/GB1455552A/en not_active Expired
- 1975-04-07 FR FR7510763A patent/FR2267107B1/fr not_active Expired
- 1975-04-07 DK DK147575A patent/DK143537C/en not_active IP Right Cessation
- 1975-04-10 DE DE19752515594 patent/DE2515594C3/en not_active Expired
- 1975-04-10 CA CA224,302A patent/CA1049409A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK147575A (en) | 1975-10-12 |
| DK143537C (en) | 1982-02-01 |
| JPS535729B2 (en) | 1978-03-01 |
| FR2267107B1 (en) | 1978-07-28 |
| DE2504615B2 (en) | 1977-07-14 |
| AU7776275A (en) | 1976-08-05 |
| DE2515594B2 (en) | 1978-12-07 |
| DE2504615C3 (en) | 1980-10-02 |
| CA1049409A (en) | 1979-02-27 |
| DE2515594C3 (en) | 1982-06-03 |
| JPS50132122A (en) | 1975-10-20 |
| FR2267107A1 (en) | 1975-11-07 |
| GB1455552A (en) | 1976-11-17 |
| DE2515594A1 (en) | 1975-10-30 |
| DE2504615A1 (en) | 1975-10-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2554428C2 (en) | ||
| KR930010584B1 (en) | Steroid lotion | |
| JP2585216B2 (en) | New pharmaceutical composition | |
| CA1256375A (en) | Ophthalmic solution containing pranoprofen | |
| JP2001505546A (en) | Antibacterial treatment for herpes simplex virus and other infectious diseases | |
| EA017660B1 (en) | Antiinflammatory and antiallergic gel | |
| DK143537B (en) | PROCEDURE FOR THE PREPARATION OF A STABLE WATER-CLEAR GEL-SHAPE OR LOTION CONTAINING A STEROID AND NEOMYCIN SALT | |
| PH26546A (en) | Topical preparation containing ofloxacin | |
| EP0100827B1 (en) | Pharmaceutical composition containing an aliphatic aminosulphonic acid | |
| US4013792A (en) | Process for the production of base for topical steroids | |
| CN106727277A (en) | A kind of mentholated nasal cavity in-situ gel spray and preparation method thereof | |
| US4034114A (en) | Treatment of skin keratoses with retinal | |
| US4840798A (en) | Astringent gel composition and method for use | |
| JP3170277B2 (en) | Topical treatment for blepharitis | |
| EP1196159B1 (en) | Use of tosylchloramide(s) for treating diseases of the skin, mucous membranes, organs and tissues | |
| KR960008315B1 (en) | Endermic gel base | |
| JPH01275516A (en) | Dandruff-preventive agent and hair-cosmetic | |
| REINIGER et al. | A Critical Study of a New Cerumenolytic Agent | |
| DE2126204A1 (en) | Lysozyme preparations | |
| US3471615A (en) | Griseofulvin-perezone composition | |
| JPS58140018A (en) | Remedy for superficial mycosis | |
| RU2134559C1 (en) | Eye drops "cornealon" | |
| JPH01163119A (en) | Composition for suppressing or controlling at least one kind of single cell organism containing quaternary ammonium fluoride | |
| JPH05155734A (en) | Additive for cosmetic | |
| JPS6084218A (en) | Eye medicine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed | ||
| PBP | Patent lapsed |