CH658387A5 - PHARMACEUTICAL PREPARATIONS. - Google Patents

PHARMACEUTICAL PREPARATIONS. Download PDF

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Publication number
CH658387A5
CH658387A5 CH1645/84A CH164584A CH658387A5 CH 658387 A5 CH658387 A5 CH 658387A5 CH 1645/84 A CH1645/84 A CH 1645/84A CH 164584 A CH164584 A CH 164584A CH 658387 A5 CH658387 A5 CH 658387A5
Authority
CH
Switzerland
Prior art keywords
acid
oxo
trimethyl
dimethyl
hydroxy
Prior art date
Application number
CH1645/84A
Other languages
German (de)
Inventor
Werner Dr Bollag
Original Assignee
Hoffmann La Roche
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Priority to CH1645/84A priority Critical patent/CH658387A5/en
Priority to DK99085A priority patent/DK99085A/en
Priority to CA000476065A priority patent/CA1243608A/en
Priority to IT19907/85A priority patent/IT1184729B/en
Priority to DE19853509455 priority patent/DE3509455A1/en
Priority to NL8500855A priority patent/NL8500855A/en
Priority to ZA852279A priority patent/ZA852279B/en
Priority to SE8501518A priority patent/SE8501518L/en
Priority to FR8504777A priority patent/FR2565823A1/en
Priority to JP60064065A priority patent/JPS60218372A/en
Priority to BE0/214732A priority patent/BE902055A/en
Priority to GB08508443A priority patent/GB2156676B/en
Priority to AU40836/85A priority patent/AU575386B2/en
Publication of CH658387A5 publication Critical patent/CH658387A5/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/008—Preparations for oily skin
    • 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
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/92—Oral administration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

658 387 658 387

2 2

Claims (4)

PATENTANSPRÜCHEPATENT CLAIMS 1. Pharmazeutisches oder kosmetisches Präparat, gekennzeichnet durch einen Gehalt an 4-Oxo- oder 4-Hydro-xy-13-cis-Vitamin A-Säure.1. Pharmaceutical or cosmetic preparation, characterized by a content of 4-oxo or 4-hydroxy-13-cis-vitamin A acid. 2. Präparat gemäss Anspruch 1 in Form von Kapseln mit 10—100 mg Wirkstoff.2. Preparation according to claim 1 in the form of capsules with 10-100 mg of active ingredient. 3. Verwendung von 4-Oxo- oder 4-Hydroxy-13-cis-Vit-amin A-Säure als Wirkstoffe bei der Herstellung von Arzneimitteln oder kosmetischen Mitteln.3. Use of 4-oxo or 4-hydroxy-13-cis-vitamin A acid as active ingredients in the manufacture of drugs or cosmetics. 4. Verwendung von 4-Oxo- oder 4-Hydroxy-13-cis-Vit-amin A-Säure gemäss Anspruch 3 als Wirkstoffe bei der Herstellung von Mitteln gegen Akne und Seborrhoe.4. Use of 4-oxo or 4-hydroxy-13-cis-vitamin A acid according to claim 3 as active ingredients in the production of agents against acne and seborrhea. Die Erfindung betrifft pharmazeutische oder kosmetische Präparate, die durch einen Gehalt an 4-Oxo- oder 4-Hydroxy-13-cis-Vitamin A-Säure gekennzeichnet sind.The invention relates to pharmaceutical or cosmetic preparations which are characterized by a content of 4-oxo or 4-hydroxy-13-cis-vitamin A acid. 4-Oxo- und 4-Hydroxy-13-cis-Vitamin A-Säure (in systematischer Nomenklatur:4-oxo- and 4-hydroxy-13-cis-vitamin A acid (in systematic nomenclature: (Z,E,E,E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-oxo-l-cyclo-(Z,E,E,E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-l-cyclo- hexen-1 -yl)-2,4,6,8-nonatetraensäure bzw. (Z,E,E,E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-l-hexen-1-yl)-2,4,6,8-nonatetraenoic acid or (Z,E,E,E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-l - cyclohexen-1 -yl)-2,4,6,8-nonatetraensäure)cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid) sind Metabolite der 13-cis-Vitamin A-Säure [J. Biol. Chem. 255,8057 (1980)].are metabolites of 13-cis-vitamin A acid [J. Biol. Chem. 255 , 8057 (1980)]. Es wurde nun gefunden, dass 4-Oxo- und 4-Hydroxy-13-cis-Vitamin A-Säure eine therapeutische Wirkung besitzen. Insbesondere können diese Verbindungen bei der Behandlung von Akne und Seborrhoe verwendet werden.It has now been found that 4-oxo and 4-hydroxy-13-cis-vitamin A acid have a therapeutic effect. In particular, these compounds can be used in the treatment of acne and seborrhea. Die erfindungsgemässen Präparate können Präparate für die systemische oder die topische Anwendung sein. Bevorzugt sind Präparate für die orale Applikation, z.B. Kapseln. Die Präparate können neben den Wirkstoffen übliche pharmazeutische Hilfsstoffe, wie Bindemittel, Füllstoffe oder An-tioxydantien enthalten. Eine Dosierungseinheit, z.B. eine Kapsel, kann etwa 10—100 mg Wirkstoff enthalten.The preparations according to the invention can be preparations for systemic or topical application. Preparations for oral administration, e.g. capsules, are preferred. In addition to the active ingredients, the preparations can contain customary pharmaceutical excipients, such as binders, fillers or antioxidants. A unit dose, e.g., a capsule, may contain about 10-100 mg of active ingredient. Zur Behandlung von Akne und Seborrhoe können die Wirkstoffe beim Menschen in Dosierungen von 0,5—5 mg/ kg täglich, vorzugsweise 1 —2 mg/kg täglich oral verabreicht werden.For the treatment of acne and seborrhea, the active ingredients can be administered orally in humans in dosages of 0.5-5 mg/kg daily, preferably 1-2 mg/kg daily. Zur topischen Applikation können die Verbindungen als Lösung oder Lotion vorliegen oder in Haarwaschmitteln (Shampoos) enthalten sein. Lösungen, Lotionen und Shampoos können etwa 0,01 —2%, vorzugsweise 0,1—0,5% Wirkstoff enthalten und einmal oder mehrmals täglich auf der Haut aufgetragen werden bzw. (Shampoos) einmal täglich oder 1 —2 mal wöchentlich zur Haarwäsche angewandt werden.For topical application, the compounds may be in the form of a solution or lotion, or may be included in shampoos. Solutions, lotions and shampoos can contain about 0.01-2%, preferably 0.1-0.5% active ingredient and be applied to the skin once or several times a day or (shampoos) once a day or 1-2 times a week to wash the hair be applied. Die nachfolgenden Beispiele erläutern die Erfindung weiter:The following examples further explain the invention: Extrakt wird mit Kochsalzlösung gewaschen, getrocknetund eingedampft und liefert ein Rohprodukt, aus dem durch Kristallisation aus Hexan/Äthylacetat reine (E,E,Z,Z)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-oxo-l-cyclo-5 hexen-1 -yl)-2,4,6,8-nonatetraensäure vom Schmelzpunkt 159 —160 :C erhalten wird.The extract is washed with brine, dried and evaporated to give a crude product from which pure (E,E,Z,Z)-3,7-dimethyl-9-(2,6,6-trimethyl-3 -oxo-1-cyclo-5-hexen-1-yl)-2,4,6,8-nonatetraenoic acid of melting point 159-160:C. 13,4 g dieser Säure werden in 600 ml Methanol bei 0 °C mit überschüssigem Diazomethan behandelt. Man lässt das Reaktionsgemisch auf Raumtemperatur aufwärmen und io dampft fiach 30 Minuten ein, wobei der13.4 g of this acid are treated with excess diazomethane in 600 ml of methanol at 0.degree. The reaction mixture is allowed to warm to room temperature and is evaporated for 30 minutes, with the (E,E,Z,Z)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-oxo-1 -cyclo-(E,E,Z,Z)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclo- hexen-l-yl)-2,4,6,8-nonatetraensäuremethylester als Rohprodukt erhalten wird. 14,2 g Rohprodukt werden in Acetonitril mit 1,48 g Dichlor-bis-benzonitril-Pd (II) und 15 2,5 ml Triäthylamin isomerisiert. Chromatographische Reinigung lieferthexen-1-yl)-2,4,6,8-nonatetraenoic acid methyl ester is obtained as a crude product. 14.2 g of crude product are isomerized in acetonitrile with 1.48 g of dichloro-bis-benzonitrile-Pd(II) and 15,2.5 ml of triethylamine. Chromatographic purification supplies (Z,E,E,E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-oxo-l-cyclo-(Z,E,E,E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-l-cyclo- hexen-l-yl)-2,4,6,8-nonatetraensäuremethylester. 13,3 g dieses Esters werden durch 30 Minuten Erhitzen mit 20 wässrig-äthanolischer Kalilauge (13,8 g KOH, 300 ml Äthanol) hydrolysiert. Das Reaktionsgemisch wird gekühlt, in Eiswasser gegossen, mit Essigsäure angesäuert und mit Äthylazetat extrahiert. Der Extrakt wird mit Kochsalzlösung gewaschen, getrocknet und eingedampft und das Roh-25 produkt aus Hexan/Äthylazetat kristallisiert. Umkristallisa-tion aus Äthylazetat/Hexan liefert reine (Z,E,E,E)-3,7-Dimethyl-9-(2,6,6-trimethyI-3-oxo-l-cyclo-hexen-1-yl)-2,4,6,8-nonatetraenoic acid methyl ester. 13.3 g of this ester are hydrolyzed by heating for 30 minutes with 20% aqueous ethanolic potassium hydroxide solution (13.8 g KOH, 300 ml ethanol). The reaction mixture is cooled, poured into ice water, acidified with acetic acid and extracted with ethyl acetate. The extract is washed with brine, dried and evaporated and the crude product is crystallized from hexane/ethyl acetate. Recrystallization from ethyl acetate/hexane gives pure (Z,E,E,E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-l-cyclo- hexen-l-yl)-2,4,6,8-nonatetraensäure vom Schmelzpunkt 164— 166°C.hexen-1-yl)-2,4,6,8-nonatetraenoic acid of melting point 164-166°C. 30 0,314 g (Z,E,E,E)-3,7-Dimethyl-9-(2,6,6,trimethyI-3-oxo-1 -cyclo-hexen-1 -yl)-2,4,6,8-nonatetraensäure werden in Methanol/Wasser 5 Minuten mit Natriumborhydrid behandelt. Das Reaktionsgemisch wird mit Essigsäure angesäuert und mit Methylenchlorid extrahiert. Der Extrakt 35 wird mit Kochsalzlösung gewaschen, getrocknet und eingedampft und aus Äthylacetat/Hexan kristallisiert. Man erhält reine30 0.314 g (Z,E,E,E)-3,7-dimethyl-9-(2,6,6,trimethyl-3-oxo-1-cyclo-hexen-1-yl)-2,4,6 ,8-nonatetraenoic acid are treated with sodium borohydride in methanol/water for 5 minutes. The reaction mixture is acidified with acetic acid and extracted with methylene chloride. The extract 35 is washed with brine, dried and evaporated and crystallized from ethyl acetate/hexane. You get pure (Z,E,E,E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-l-cyclohexen-1 -yl)-2„4,6,8-nonatetraensäure.(Z,E,E,E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid. 4040 Beispiel 2example 2 Herstellung einer Kapsel für orale Applikation:Preparation of a capsule for oral application: Eine wässrige Suspension von 27 Gew.-% Gelatine (Bloom 30), 41 Gew.-% Maltodextrin MD 05,7 Gew.-% 45 Natriumascorbat und 25 Gew.-%An aqueous suspension of 27% by weight gelatin (Bloom 30), 41% by weight Maltodextrin MD 05.7% by weight 45 Sodium Ascorbate and 25% by weight (Z,E,E,E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-oxo-l-cyclo-(Z,E,E,E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-l-cyclo- hexen-1 -yl)-2,4,6,8-nonatetraensäure werden auf eine mittlere Partikelgrösse von 0,5 um gemahlen und sprühgetrocknet. Jeweils 25 mg des so erhaltenen Pulso vers, 20 mg AVICEL PH 102, (mikrokristalline Zellulose), 34 mg Milchzucker und 6 mg POLYPLASDONE (querver-netztes Polyvinylpyrrolidon; Crosspovidon) werden gemischt und in Gelatinekapseln abgefüllt.hexen-1-yl)-2,4,6,8-nonatetraenoic acid are ground to an average particle size of 0.5 μm and spray-dried. 25 mg each of the Pulso vers obtained in this way, 20 mg AVICEL PH 102 (microcrystalline cellulose), 34 mg lactose and 6 mg POLYPLASDONE (cross-linked polyvinylpyrrolidone; crosspovidone) are mixed and filled into gelatine capsules. 5555 Beispiel 1 Herstellung der Wirkstoffe 56,2 g [5-(3-Oxo-2,6,6-trimethyl-l-cyclohexen-l-yl)-3-methyl-2,4-pentadienyl]triphenyl phosphonium bromide und 11,4 g 4-Hydroxy-3-methyl-2-butenolid werden in 250 ml Isopropanol bei 0—5 °C mit 94,3 ml 2,12 N KOH in Isopro- 60 panol (0,2 Mol) versetzt. Das Reaktionsgemisch wird 1 Stunde bei 5—10 °C belassen und dann auf Raumtemperatur aufgewärmt. Nach 30 Minuten wird das Reaktionsgemisch in 5%iger Kochsalzlösung gegossen, mit Schwefelsäure angesäuert und mit Äthylacetat extrahiert. Der organische 65Example 1 Preparation of the active substances 56.2 g of [5-(3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]triphenyl phosphonium bromide and 11, 94.3 ml of 2.12 N KOH in isopropanol (0.2 mol) are added to 4 g of 4-hydroxy-3-methyl-2-butenolide in 250 ml of isopropanol at 0-5 °C. The reaction mixture is left at 5-10°C for 1 hour and then warmed to room temperature. After 30 minutes the reaction mixture is poured into 5% brine, acidified with sulfuric acid and extracted with ethyl acetate. The organic 65 Beispiel 3 Herstellung einer Lotion: (Z,E,E,E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-oxo-l -cyclohexen-1 -yl)-Example 3 Preparation of a lotion: (Z,E,E,E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)- 2,4,6,8-nonatetraensäure 0,01— 2,0 g2,4,6,8-nonatetraenoic acid 0.01-2.0 g Feinsprit 10,0 —52,0 gfine spirits 10.0 —52.0 g Propylenglykol 0 — 50,0 gPropylene Glycol 0 — 50.0 g Polyäthylenglykol 0 — 50,0 gPolyethylene glycol 0 — 50.0 g Dimethylsulfoxid 0 — 50,0 g Der Wirkstoff wird im Gemisch der Lösungsmittel gelöst.dimethyl sulfoxide 0 - 50.0 g The active substance is dissolved in the mixture of solvents.
CH1645/84A 1984-04-02 1984-04-02 PHARMACEUTICAL PREPARATIONS. CH658387A5 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
CH1645/84A CH658387A5 (en) 1984-04-02 1984-04-02 PHARMACEUTICAL PREPARATIONS.
DK99085A DK99085A (en) 1984-04-02 1985-03-04 PHARMACEUTICAL PREPARATIONS CONTAINING A-VITAMIC ACID DERIVATIVES
CA000476065A CA1243608A (en) 1984-04-02 1985-03-08 Pharmaceutical preparations
IT19907/85A IT1184729B (en) 1984-04-02 1985-03-14 COSMETIC PHARMACEUTICAL PRODUCTS, IN PARTICULAR FOR THE TREATMENT OF ACNE AND SEBORRHEA
DE19853509455 DE3509455A1 (en) 1984-04-02 1985-03-15 PHARMACEUTICAL PREPARATIONS
NL8500855A NL8500855A (en) 1984-04-02 1985-03-22 PHARMACEUTICAL OR COSMETIC PREPARATIONS.
ZA852279A ZA852279B (en) 1984-04-02 1985-03-26 Pharmaceutical preparations
SE8501518A SE8501518L (en) 1984-04-02 1985-03-27 PHARMACEUTICAL PREPARATIONS
FR8504777A FR2565823A1 (en) 1984-04-02 1985-03-29 PHARMACEUTICAL AND COSMETOLOGICAL PREPARATIONS CONTAINING VITAMIN A DERIVATIVES
JP60064065A JPS60218372A (en) 1984-04-02 1985-03-29 Pharmaceutical or cosmetic composition
BE0/214732A BE902055A (en) 1984-04-02 1985-03-29 PHARMACEUTICAL PREPARATIONS.
GB08508443A GB2156676B (en) 1984-04-02 1985-04-01 Pharmaceutical preparations containing vitamin a derivatives
AU40836/85A AU575386B2 (en) 1984-04-02 1985-04-02 Pharmaceutical compositions of 4-oxo or 4-hydroxy-13-cis-vitamin

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1645/84A CH658387A5 (en) 1984-04-02 1984-04-02 PHARMACEUTICAL PREPARATIONS.

Publications (1)

Publication Number Publication Date
CH658387A5 true CH658387A5 (en) 1986-11-14

Family

ID=4215302

Family Applications (1)

Application Number Title Priority Date Filing Date
CH1645/84A CH658387A5 (en) 1984-04-02 1984-04-02 PHARMACEUTICAL PREPARATIONS.

Country Status (13)

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JP (1) JPS60218372A (en)
AU (1) AU575386B2 (en)
BE (1) BE902055A (en)
CA (1) CA1243608A (en)
CH (1) CH658387A5 (en)
DE (1) DE3509455A1 (en)
DK (1) DK99085A (en)
FR (1) FR2565823A1 (en)
GB (1) GB2156676B (en)
IT (1) IT1184729B (en)
NL (1) NL8500855A (en)
SE (1) SE8501518L (en)
ZA (1) ZA852279B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1282326C (en) * 1984-12-14 1991-04-02 Paul J. Jarosz Pharmaceutical composition containing 13-cis vitamin a acid as the active ingredient
US5879716A (en) * 1985-12-18 1999-03-09 Advanced Polymer Systems, Inc. Methods and compositions for topical delivery of benzoyl peroxide
US5955109A (en) * 1985-12-18 1999-09-21 Advanced Polymer Systems, Inc. Methods and compositions for topical delivery of retinoic acid
IL90069A (en) * 1988-04-26 1994-04-12 Us Health 13-cis- retinoic acid for use in the preparation of a medicament for treating conglobate and nodulocystic acne
TW442459B (en) * 1996-04-15 2001-06-23 Hoffmann La Roche Retinoid compounds, pharmaceutical composition comprising same and process for the preparation thereof
EP0802181B1 (en) * 1996-04-15 1999-12-22 F. Hoffmann-La Roche Ag Retinoids
EP1971331A2 (en) * 2005-12-09 2008-09-24 Basilea Pharmaceutica AG 4-oxo-(iso)tretinoin for the topical treatment of severe dermatological disorders

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4169103A (en) * 1978-04-12 1979-09-25 Hoffmann-La Roche Inc. Nonatetraenoic acid derivatives
WO1982002833A1 (en) * 1981-02-17 1982-09-02 Gail Sansone Bazzano The use of retinoids and their derivatives to increase the rate of growth of human scalp hair and to increase the rate of growth of fur in certain fur-bearing animals

Also Published As

Publication number Publication date
NL8500855A (en) 1985-11-01
ZA852279B (en) 1985-11-27
IT8519907A0 (en) 1985-03-14
GB2156676B (en) 1987-10-21
DK99085A (en) 1985-10-03
GB8508443D0 (en) 1985-05-09
FR2565823A1 (en) 1985-12-20
GB2156676A (en) 1985-10-16
IT1184729B (en) 1987-10-28
JPS60218372A (en) 1985-11-01
SE8501518D0 (en) 1985-03-27
CA1243608A (en) 1988-10-25
BE902055A (en) 1985-09-30
AU4083685A (en) 1985-10-10
DE3509455A1 (en) 1985-10-10
AU575386B2 (en) 1988-07-28
DK99085D0 (en) 1985-03-04
SE8501518L (en) 1985-10-03

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