CA1243608A - Pharmaceutical preparations - Google Patents
Pharmaceutical preparationsInfo
- Publication number
- CA1243608A CA1243608A CA000476065A CA476065A CA1243608A CA 1243608 A CA1243608 A CA 1243608A CA 000476065 A CA000476065 A CA 000476065A CA 476065 A CA476065 A CA 476065A CA 1243608 A CA1243608 A CA 1243608A
- Authority
- CA
- Canada
- Prior art keywords
- oxo
- acid
- dimethyl
- cyclohexen
- trimethyl
- 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.)
- Expired
Links
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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Birds (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Abstract
Abstract Pharmaceutical or cosmetic preparations containing 4-oxo- or 4-hydroxy-13-cis-vitamin A acid as the active substance can be used for the treatment of acne or seborrhoea.
Description
The invention is concerned with pharmaceutical or cos~
metic preparations which contain 4-oxo- or ~-hydroxy~13~cis--vitamin A acid.
~-oxo- and 4-hyd~oxy-13-cis-vitamin A acid [i~ system-atic nomenclature: (Z,E,E,E)-3,7-dimethyl -9-(2,6,6,t~i-methyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid and (Z,E,E,E)-3,7-dimethyl-9-(2,6,6-trimethyl -3-hydroxy-1--cyclohexen-l-yl)-2,4,6,8-nonatetraenoic acid, respectively]
are metabolites of 13-cis-vitamin A acid ~J. Biol. Chem.
255, 8057 (198~)].
It has now been found that 4-oxo- and 4-hydroxy-13-cis--vitamin A acid have a therapeutic activity. In particular, these compounds can be used in the treatment of acne and seborrhoea.
The preparations in accordance with the invention can be preparations for systemic or topical use. Preparations for oral administration, e.g. capsules, are preferred. In addition to the active substances the preparations can con-tain usual pharmaceutical adjuvants such as binding agents, filling materials or antioxidan~s. A dosage unit, e.g. a capsule, can contain about 10-100 mg of active substance~
For the treatmen~ of acne and seborrhoea the active substances can be administered orally to human beings in ~ dosages of 0.5-5 mg/kg daily, preferably 1-~ mg~kg daily.
For topical application the compounds can be present as a solution or lotion or can be incorporated in hair washes (shampoos). Solutions, lotions and shampoos can contain about 0.01-Z%, preferably 0.1-0.5%, of ac~ive substance and can be applied to the skin once or several times daily or Mé/1701.85 .
.~ .
3~
(shampaos) can be used for washing the hair once daily or once or twice a week.
The following Examples ill~strate the invention ~urther~
Example 1 Manufacture of the active substances 56.2 g of [5-(3-oxo-2,6,6 -trimethyl-l-cyclohexen-l--yl~-3-methyl-2,4-pentadienyl]triphenylphosphonium bromide and 11.4 g of 4-hydroxy-3-methyl-2-butenolide in 250 ml of isopropanol are treated at 0-5C with 94.3 ml of 2.12 N KOH
in isopropanol (0.2 mol~. The reaction mixture is left at 5-10C for 1 hour and then warmed ~o room tempera~ure. After 30 minutes the reaction mixture is poured into 5% sodium chloride solution, acidified with sulphuric acid and extracted with ethyl acetate. The organic extract is washed with sodium chloride solution, dried and evaporated and yields a crude product from which pure tE,E,Z,Z)-3,7-di-methyl-s-~2,6,6 -trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,S,8--nonatetraenoic acid of melting point 159-160C is obtained ; 25 by crystallization from hexane/ethyl acetate.
13.~ g of this acid in 600 ml of methanol are treated at O~C with excess diazomethane. The reaction mixture is left to warm to room temperature and is evaporated after 30 min-utes, whereby methyl (E,E,Z,Z)-3,7-dimethyl-9-(2,6,6-tri-methyl-3-oxo -1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate is obtained as the crude product. 14.2 g of crude product are isomerized in acetonitrile with 1.48 g of dichloro-bis-ben-zonitrile-Pd (II) and 2.5 ml of triethylam;ne. Chromato-graphic purification yields methyl (Z,E,E,E)-3,7-dimethyl-g--(2~6~6-trimethyl -3-oxo-1-cyclohexen-1-yl)-2,4,6,8 nona-tetraenoate. 13.3 g of this ester are hydroly2ed by heating for 30 minutes with aqueous-ethanolic potassium hydroxide , ~", (13.8 g of KOH, 300 ml of ethanol). The reactio~ mixture is cooled, poured into ice-water, acidified with acetic acid and extracted with ethyl aceta~e. The extract is washed with sodium chloride solution, dried and evaporated and the crud~
product is crystallized from hexanetethyl acetate.
Recrystallization from ethyl acetate/hexane yields pure (Z,E,E,E)-3,7-dimethyl-9-(2,6,6 -t~imeth~1-3-oxo-1-c~clo-hexen-1-yl)-2,4,6,8-nonatetraenoic acid of melting point 164-166C.
0.314 g of (Z,E,E,E3-3,7-dimethyl-9-(2,6,6-trimethyl-3--oxo -l-cyclohexen-l-yl)-2,~,6,8-nonatetraenoic acid in methanol/water is treated with sodium borohydride for 5 minutes. The reaction mixture is acidified with acetic acid and extracted with methylene chloride. The extract is washed with sodium chloride solution, dried and evaporated and the residue is crystallized from ethyl acetate/hexane.
Pure (Z,E,E,~)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1--cyclohexen-l-yl)-2 J 4,6,8-nonatetraenoic acid is obtained.
ExamPle ?~
- 25 Manufacture of a caPsule for oral administration:
.
~n aqueous suspension o~ 27 wt.~ of gelatine (Bloom 30)~
41 wt.% of maltodextrin ~D 05, 7 wt.% of sodium ascorbate and 25 wt.~ of ~,E,E,E)-3,7-dimethyl-9-t2.6,6-trimethyl-3--oxo -1-cyclohexe~-1-yl)-2,4,6,8-nonatetraenoic acid are milled to an average particle size of 0.5 ~m and spray--dried. In each case 25 mg of the thus-obtained powder, 20 mg of AVICEL PH 102, (microcrystalline cellulose), 34 mg of lactose and 6 mg of PQLYPLASDONE (cross-lin~ed polyvinyl-pyrrolidone; c~oss povidone) are mîxed and filled into gelatine capsules.
*Trade Marks , -~ .
ExamPle 3 Manufacture 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-nona-tetraenoic acid 0.01 - 2.0 g Rectified alcohol 10.0 - 52.0 g Propylene glycol 0 - 50.0 g Polyethylene glycol 0 - 50.0 g Dimethyl sulphoxide 0 - 50.0 g The active substance is dissolved in the mixture of the solvents.
' '"'
metic preparations which contain 4-oxo- or ~-hydroxy~13~cis--vitamin A acid.
~-oxo- and 4-hyd~oxy-13-cis-vitamin A acid [i~ system-atic nomenclature: (Z,E,E,E)-3,7-dimethyl -9-(2,6,6,t~i-methyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid and (Z,E,E,E)-3,7-dimethyl-9-(2,6,6-trimethyl -3-hydroxy-1--cyclohexen-l-yl)-2,4,6,8-nonatetraenoic acid, respectively]
are metabolites of 13-cis-vitamin A acid ~J. Biol. Chem.
255, 8057 (198~)].
It has now been found that 4-oxo- and 4-hydroxy-13-cis--vitamin A acid have a therapeutic activity. In particular, these compounds can be used in the treatment of acne and seborrhoea.
The preparations in accordance with the invention can be preparations for systemic or topical use. Preparations for oral administration, e.g. capsules, are preferred. In addition to the active substances the preparations can con-tain usual pharmaceutical adjuvants such as binding agents, filling materials or antioxidan~s. A dosage unit, e.g. a capsule, can contain about 10-100 mg of active substance~
For the treatmen~ of acne and seborrhoea the active substances can be administered orally to human beings in ~ dosages of 0.5-5 mg/kg daily, preferably 1-~ mg~kg daily.
For topical application the compounds can be present as a solution or lotion or can be incorporated in hair washes (shampoos). Solutions, lotions and shampoos can contain about 0.01-Z%, preferably 0.1-0.5%, of ac~ive substance and can be applied to the skin once or several times daily or Mé/1701.85 .
.~ .
3~
(shampaos) can be used for washing the hair once daily or once or twice a week.
The following Examples ill~strate the invention ~urther~
Example 1 Manufacture of the active substances 56.2 g of [5-(3-oxo-2,6,6 -trimethyl-l-cyclohexen-l--yl~-3-methyl-2,4-pentadienyl]triphenylphosphonium bromide and 11.4 g of 4-hydroxy-3-methyl-2-butenolide in 250 ml of isopropanol are treated at 0-5C with 94.3 ml of 2.12 N KOH
in isopropanol (0.2 mol~. The reaction mixture is left at 5-10C for 1 hour and then warmed ~o room tempera~ure. After 30 minutes the reaction mixture is poured into 5% sodium chloride solution, acidified with sulphuric acid and extracted with ethyl acetate. The organic extract is washed with sodium chloride solution, dried and evaporated and yields a crude product from which pure tE,E,Z,Z)-3,7-di-methyl-s-~2,6,6 -trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,S,8--nonatetraenoic acid of melting point 159-160C is obtained ; 25 by crystallization from hexane/ethyl acetate.
13.~ g of this acid in 600 ml of methanol are treated at O~C with excess diazomethane. The reaction mixture is left to warm to room temperature and is evaporated after 30 min-utes, whereby methyl (E,E,Z,Z)-3,7-dimethyl-9-(2,6,6-tri-methyl-3-oxo -1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate is obtained as the crude product. 14.2 g of crude product are isomerized in acetonitrile with 1.48 g of dichloro-bis-ben-zonitrile-Pd (II) and 2.5 ml of triethylam;ne. Chromato-graphic purification yields methyl (Z,E,E,E)-3,7-dimethyl-g--(2~6~6-trimethyl -3-oxo-1-cyclohexen-1-yl)-2,4,6,8 nona-tetraenoate. 13.3 g of this ester are hydroly2ed by heating for 30 minutes with aqueous-ethanolic potassium hydroxide , ~", (13.8 g of KOH, 300 ml of ethanol). The reactio~ mixture is cooled, poured into ice-water, acidified with acetic acid and extracted with ethyl aceta~e. The extract is washed with sodium chloride solution, dried and evaporated and the crud~
product is crystallized from hexanetethyl acetate.
Recrystallization from ethyl acetate/hexane yields pure (Z,E,E,E)-3,7-dimethyl-9-(2,6,6 -t~imeth~1-3-oxo-1-c~clo-hexen-1-yl)-2,4,6,8-nonatetraenoic acid of melting point 164-166C.
0.314 g of (Z,E,E,E3-3,7-dimethyl-9-(2,6,6-trimethyl-3--oxo -l-cyclohexen-l-yl)-2,~,6,8-nonatetraenoic acid in methanol/water is treated with sodium borohydride for 5 minutes. The reaction mixture is acidified with acetic acid and extracted with methylene chloride. The extract is washed with sodium chloride solution, dried and evaporated and the residue is crystallized from ethyl acetate/hexane.
Pure (Z,E,E,~)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1--cyclohexen-l-yl)-2 J 4,6,8-nonatetraenoic acid is obtained.
ExamPle ?~
- 25 Manufacture of a caPsule for oral administration:
.
~n aqueous suspension o~ 27 wt.~ of gelatine (Bloom 30)~
41 wt.% of maltodextrin ~D 05, 7 wt.% of sodium ascorbate and 25 wt.~ of ~,E,E,E)-3,7-dimethyl-9-t2.6,6-trimethyl-3--oxo -1-cyclohexe~-1-yl)-2,4,6,8-nonatetraenoic acid are milled to an average particle size of 0.5 ~m and spray--dried. In each case 25 mg of the thus-obtained powder, 20 mg of AVICEL PH 102, (microcrystalline cellulose), 34 mg of lactose and 6 mg of PQLYPLASDONE (cross-lin~ed polyvinyl-pyrrolidone; c~oss povidone) are mîxed and filled into gelatine capsules.
*Trade Marks , -~ .
ExamPle 3 Manufacture 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-nona-tetraenoic acid 0.01 - 2.0 g Rectified alcohol 10.0 - 52.0 g Propylene glycol 0 - 50.0 g Polyethylene glycol 0 - 50.0 g Dimethyl sulphoxide 0 - 50.0 g The active substance is dissolved in the mixture of the solvents.
' '"'
Claims (2)
1. A pharmaceutical or cosmetic preparation which contains 4-oxo- or 4-hydroxy-13-cis-vitamin A acid.
2. A preparation according to claim 1 in the form of capsules containing 10-100 mg of active substance.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1645/84 | 1984-04-02 | ||
| CH1645/84A CH658387A5 (en) | 1984-04-02 | 1984-04-02 | PHARMACEUTICAL PREPARATIONS. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1243608A true CA1243608A (en) | 1988-10-25 |
Family
ID=4215302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000476065A Expired CA1243608A (en) | 1984-04-02 | 1985-03-08 | Pharmaceutical preparations |
Country Status (13)
| Country | Link |
|---|---|
| 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)
| 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 |
| US5955109A (en) * | 1985-12-18 | 1999-09-21 | Advanced Polymer Systems, Inc. | Methods and compositions for topical delivery of retinoic acid |
| US5879716A (en) * | 1985-12-18 | 1999-03-09 | Advanced Polymer Systems, Inc. | Methods and compositions for topical delivery of benzoyl peroxide |
| 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 |
| EP0802181B1 (en) * | 1996-04-15 | 1999-12-22 | F. Hoffmann-La Roche Ag | Retinoids |
| TW442459B (en) * | 1996-04-15 | 2001-06-23 | Hoffmann La Roche | Retinoid compounds, pharmaceutical composition comprising same and process for the preparation thereof |
| WO2007065289A2 (en) * | 2005-12-09 | 2007-06-14 | Basilea Pharmaceutica Ag | 4-oxo-(iso)tretinoin for the topical treatment of severe dermatological disorders |
Family Cites Families (2)
| 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 |
-
1984
- 1984-04-02 CH CH1645/84A patent/CH658387A5/en not_active IP Right Cessation
-
1985
- 1985-03-04 DK DK99085A patent/DK99085A/en not_active Application Discontinuation
- 1985-03-08 CA CA000476065A patent/CA1243608A/en not_active Expired
- 1985-03-14 IT IT19907/85A patent/IT1184729B/en active
- 1985-03-15 DE DE19853509455 patent/DE3509455A1/en not_active Withdrawn
- 1985-03-22 NL NL8500855A patent/NL8500855A/en not_active Application Discontinuation
- 1985-03-26 ZA ZA852279A patent/ZA852279B/en unknown
- 1985-03-27 SE SE8501518A patent/SE8501518L/en not_active Application Discontinuation
- 1985-03-29 FR FR8504777A patent/FR2565823A1/en active Pending
- 1985-03-29 JP JP60064065A patent/JPS60218372A/en active Pending
- 1985-03-29 BE BE0/214732A patent/BE902055A/en not_active IP Right Cessation
- 1985-04-01 GB GB08508443A patent/GB2156676B/en not_active Expired
- 1985-04-02 AU AU40836/85A patent/AU575386B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| IT8519907A0 (en) | 1985-03-14 |
| GB8508443D0 (en) | 1985-05-09 |
| SE8501518L (en) | 1985-10-03 |
| DK99085D0 (en) | 1985-03-04 |
| ZA852279B (en) | 1985-11-27 |
| NL8500855A (en) | 1985-11-01 |
| AU575386B2 (en) | 1988-07-28 |
| DK99085A (en) | 1985-10-03 |
| AU4083685A (en) | 1985-10-10 |
| BE902055A (en) | 1985-09-30 |
| IT1184729B (en) | 1987-10-28 |
| CH658387A5 (en) | 1986-11-14 |
| SE8501518D0 (en) | 1985-03-27 |
| GB2156676A (en) | 1985-10-16 |
| DE3509455A1 (en) | 1985-10-10 |
| GB2156676B (en) | 1987-10-21 |
| JPS60218372A (en) | 1985-11-01 |
| FR2565823A1 (en) | 1985-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |