IE42308L - 16,16-disubstituted androstenes - Google Patents
16,16-disubstituted androstenesInfo
- Publication number
- IE42308L IE42308L IE760412A IE41276A IE42308L IE 42308 L IE42308 L IE 42308L IE 760412 A IE760412 A IE 760412A IE 41276 A IE41276 A IE 41276A IE 42308 L IE42308 L IE 42308L
- Authority
- IE
- Ireland
- Prior art keywords
- carbon atoms
- radicals
- radical
- alkyl radical
- group
- Prior art date
Links
- 150000001443 androstenes Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- 239000003098 androgen Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000001419 dependent effect Effects 0.000 abstract 2
- 208000002874 Acne Vulgaris Diseases 0.000 abstract 1
- 206010039792 Seborrhoea Diseases 0.000 abstract 1
- 206010000496 acne Diseases 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 210000004907 gland Anatomy 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 208000017520 skin disease Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/0037—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
Pharmaceutically utilisable 3-ketosteroids which are disubstituted in position 16 and have the formula I <IMAGE> in which R3 are alkyl radicals with 1 to 5 carbon atoms, alkenyl or cycloalkyl radicals with 3 to 6 carbon atoms or phenylalkyl radicals with 1 to 3 carbon atoms in the alkyl radical, it being possible for the phenyl radicals to be substituted, R4 is the hydroxyl group or the radical -OR6 where R6 is an acyl radical with 2 to 7 carbon atoms, an alkyl radical with 1 to 4 carbon atoms, or the benzyl group which can be substituted, and R5 is a hydrogen atom or an alkyl radical with 1 to 5 carbon atoms, it also being possible for R4 and R5, together with the carbon atom to which they are bonded, to form the carbonyl group, are obtained by removing the protective group in the compound of the formula I in which the double bond is in the 5,6 position and the 3-carbonyl group is protected by ketal, hemithioketal or thioketal. The double bond rearranges during the elimination and provides the required 4,5 bond in the final product. The prepared compounds are particularly valuable for the treatment of androgen-dependent skin disorders such as acne and seborrhoea and of other androgen-dependent disorders associated with skin and hair glands.
[GB1538227A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11819/75A GB1538227A (en) | 1975-03-21 | 1975-03-21 | 16,16-disubstituted steroids of the androstene series |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42308L true IE42308L (en) | 1976-09-21 |
| IE42308B1 IE42308B1 (en) | 1980-07-16 |
Family
ID=9993275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE412/76A IE42308B1 (en) | 1975-03-21 | 1976-03-01 | 16, 16-disubstituted steroids of the androstene series |
Country Status (15)
| Country | Link |
|---|---|
| JP (2) | JPS51118756A (en) |
| AT (1) | AT357700B (en) |
| AU (1) | AU501246B2 (en) |
| BE (1) | BE839751A (en) |
| CA (1) | CA1069498A (en) |
| CH (2) | CH621560A5 (en) |
| DE (1) | DE2610497C2 (en) |
| DK (1) | DK143757C (en) |
| FR (2) | FR2304345A1 (en) |
| GB (1) | GB1538227A (en) |
| IE (1) | IE42308B1 (en) |
| IL (2) | IL49132A (en) |
| NL (1) | NL184111C (en) |
| SE (2) | SE7603410L (en) |
| ZA (1) | ZA761324B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1602960A (en) * | 1977-05-25 | 1981-11-18 | Beecham Group Ltd | Process for preparing 16,16-disubstituted steroids of the androstene series |
| DE2943778A1 (en) * | 1979-10-26 | 1981-05-07 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | 17-Alpha:alkyl-4,15-androstadiene-3-one derivs. - topical antiandrogens effective against acne, seborrhoea, alopecia and hirsutism |
| DE3514272A1 (en) * | 1985-04-17 | 1986-10-23 | Schering AG, 1000 Berlin und 4709 Bergkamen | DERMATICA |
| GB9021546D0 (en) * | 1990-10-04 | 1990-11-21 | Beecham Group Plc | Novel composition |
| EP0555309A1 (en) * | 1990-10-31 | 1993-08-18 | BEECHAM GROUP plc | Topical composition with retinoid penetration enhancer |
| GB9205194D0 (en) * | 1992-03-10 | 1992-04-22 | Smithkline Beecham Plc | Novel composition |
| US20050009797A1 (en) * | 2001-12-19 | 2005-01-13 | Mitsuaki Nakamura | Androstane derivative having substituent in 7- abd 17--positions |
| CN108558975B (en) * | 2018-04-26 | 2021-03-02 | 昆明理工大学 | 12β-Hydroxy-androsta 4,14-dien-16-one compounds and their application |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3853926A (en) * | 1973-05-29 | 1974-12-10 | Searle & Co | 17{62 -hydroxy-16,16-dimethylester-4-en-3-one |
-
1975
- 1975-03-21 GB GB11819/75A patent/GB1538227A/en not_active Expired
-
1976
- 1976-03-01 IE IE412/76A patent/IE42308B1/en unknown
- 1976-03-02 IL IL49132A patent/IL49132A/en unknown
- 1976-03-12 DE DE2610497A patent/DE2610497C2/en not_active Expired
- 1976-03-15 FR FR7607328A patent/FR2304345A1/en active Granted
- 1976-03-16 AT AT191376A patent/AT357700B/en not_active IP Right Cessation
- 1976-03-18 BE BE165323A patent/BE839751A/en not_active IP Right Cessation
- 1976-03-18 SE SE7603410A patent/SE7603410L/en not_active Application Discontinuation
- 1976-03-19 AU AU12207/76A patent/AU501246B2/en not_active Expired
- 1976-03-19 NL NLAANVRAGE7602949,A patent/NL184111C/en not_active IP Right Cessation
- 1976-03-19 CA CA248,260A patent/CA1069498A/en not_active Expired
- 1976-03-19 JP JP51030741A patent/JPS51118756A/en active Granted
- 1976-03-19 DK DK123476A patent/DK143757C/en active
- 1976-03-22 CH CH354376A patent/CH621560A5/en not_active IP Right Cessation
- 1976-04-04 ZA ZA761324A patent/ZA761324B/en unknown
-
1979
- 1979-03-09 CH CH228479A patent/CH631996A5/en not_active IP Right Cessation
- 1979-03-13 SE SE7902256A patent/SE7902256L/en not_active Application Discontinuation
- 1979-10-19 IL IL58505A patent/IL58505A0/en unknown
-
1980
- 1980-02-26 FR FR8004184A patent/FR2445340A1/en active Granted
-
1985
- 1985-12-24 JP JP60291811A patent/JPS61178920A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IE42308B1 (en) | 1980-07-16 |
| JPS51118756A (en) | 1976-10-18 |
| IL49132A0 (en) | 1976-05-31 |
| NL7602949A (en) | 1976-09-23 |
| FR2304345B1 (en) | 1980-11-07 |
| FR2445340A1 (en) | 1980-07-25 |
| AT357700B (en) | 1980-07-25 |
| DE2610497C2 (en) | 1986-10-16 |
| FR2304345A1 (en) | 1976-10-15 |
| AU501246B2 (en) | 1979-06-14 |
| BE839751A (en) | 1976-09-20 |
| DK123476A (en) | 1976-09-22 |
| CA1069498A (en) | 1980-01-08 |
| CH621560A5 (en) | 1981-02-13 |
| JPS61178920A (en) | 1986-08-11 |
| DK143757C (en) | 1982-03-22 |
| JPS625920B2 (en) | 1987-02-07 |
| ATA191376A (en) | 1979-12-15 |
| IL49132A (en) | 1980-05-30 |
| DE2610497A1 (en) | 1976-10-07 |
| CH631996A5 (en) | 1982-09-15 |
| ZA761324B (en) | 1977-02-23 |
| FR2445340B1 (en) | 1983-02-11 |
| GB1538227A (en) | 1979-01-10 |
| SE7603410L (en) | 1976-09-22 |
| IL58505A0 (en) | 1980-01-31 |
| AU1220776A (en) | 1977-09-22 |
| NL184111B (en) | 1988-11-16 |
| NL184111C (en) | 1989-04-17 |
| JPS6355488B2 (en) | 1988-11-02 |
| DK143757B (en) | 1981-10-05 |
| SE7902256L (en) | 1979-03-13 |
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