GB1383334A - 15alpha,16alpha-methylene-steroids - Google Patents
15alpha,16alpha-methylene-steroidsInfo
- Publication number
- GB1383334A GB1383334A GB794372A GB794372A GB1383334A GB 1383334 A GB1383334 A GB 1383334A GB 794372 A GB794372 A GB 794372A GB 794372 A GB794372 A GB 794372A GB 1383334 A GB1383334 A GB 1383334A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methylene
- acyloxy
- prepared
- novel
- steroids
- 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
- 230000001590 oxidative effect Effects 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 150000003431 steroids Chemical class 0.000 abstract 2
- 229910007565 Zn—Cu Inorganic materials 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000001195 anabolic effect Effects 0.000 abstract 1
- 230000001548 androgenic effect Effects 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 abstract 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 238000010525 oxidative degradation reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/0065—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified
- C07J7/0075—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified substituted in position 17 alfa
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/008—3 membered carbocyclic rings in position 15/16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
1383334 15α,16α-Methylene-steroids SCHERING AG 21 Feb 1972 [24 Feb 1971] 7943/72 Heading C2U Novel steroids of the formula (wherein R 1 is H or a C 1-4 aliphatic hydrocarbon group and R 2 is H or acyl), are prepared by (a) hydrolysing a novel 3#-acyloxy-15α,16α,methylene-#<SP>5</SP>-androsten-17-one (prepared by oxidative degradation of a 3#-acyloxy-15α,16α-methylene- #<SP>5</SP>-pregnene-17α,20#-diol), to the 3#ol oxidizing this by the Oppenauer method to the novel 15α,16α - methylene - #<SP>4</SP> - androstene - 3,17- dione, reducing this with a complex metal hydride to the corresponding 3#,17#-diol and oxidizing this to the required 3-one (wherein R 1 and R 2 are each H), which may subsequently be esterified; or (b) converting the starting material for process (a) to a 17α-hydrocarbyl- 15α,16α - methylene - #<SP>5</SP> - androstene - 3#,17#- diol by reaction with a suitable hydrocarbonmetal compound, if desired hydrogenating any 17α-alkynyl group to a 17α-alkenyl or 17α-alkyl group, and then oxidizing to give the required product (wherein R 2 is H and R 1 is an aliphatic hydrocarbon group), which may subsequently be esterified. 3# - Acyloxy - 15α,16α - methylene - #<SP>5</SP>- pregnene-17α,20#-diols (e.g. the 3#-acetoxy compound), are prepared by the action of methylene iodide and a Zn-Cu couple on the corresponding 3# - acyloxy - #<SP>5</SP>,<SP>15</SP> - pregnadiene- 17α,20#-diols, prepared in turn by reduction of the corresponding 20-ones. The novel steroids of the above formula are stated to display a high androgenic activity combined with a favourably differentiated anabolic activity, and they may be made up into pharmaceutical compositions with suitable carriers.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2109555A DE2109555C3 (en) | 1971-02-24 | 1971-02-24 | New 15 a, 16 a -methylene steroids, drugs containing them and processes for their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1383334A true GB1383334A (en) | 1974-02-12 |
Family
ID=5800118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB794372A Expired GB1383334A (en) | 1971-02-24 | 1972-02-21 | 15alpha,16alpha-methylene-steroids |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3749742A (en) |
| AT (2) | AT315393B (en) |
| AU (1) | AU456892B2 (en) |
| BE (1) | BE779797A (en) |
| CA (1) | CA963000A (en) |
| CH (1) | CH581149A5 (en) |
| CS (2) | CS167346B2 (en) |
| DD (1) | DD96065A5 (en) |
| DE (1) | DE2109555C3 (en) |
| DK (1) | DK130987B (en) |
| ES (1) | ES400056A1 (en) |
| FI (1) | FI49029C (en) |
| FR (1) | FR2126334B1 (en) |
| GB (1) | GB1383334A (en) |
| HU (1) | HU162901B (en) |
| IE (1) | IE36121B1 (en) |
| IL (1) | IL38828A (en) |
| NL (1) | NL7202466A (en) |
| NO (1) | NO135527C (en) |
| SE (1) | SE377338B (en) |
| ZA (1) | ZA721052B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3994937A (en) * | 1972-02-11 | 1976-11-30 | Schering Aktiengesellschaft | 15α,16α-Methylene-4-estren-17β-ols |
| DE2456068A1 (en) * | 1974-11-23 | 1976-08-12 | Schering Ag | PROCESS FOR THE PRODUCTION OF OESTREN3,17-DIONE DERIVATIVES |
| DE102007027635A1 (en) | 2007-06-12 | 2008-12-18 | Bayer Schering Pharma Aktiengesellschaft | 17β-cyano-19-androst-4-ene derivative, its use and the derivative-containing drug |
| BE1027859B1 (en) * | 2019-12-13 | 2021-07-14 | Georges Debled | Steroid hormone for the prevention of diseases associated with aging |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1643005C3 (en) * | 1967-02-09 | 1975-05-22 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 15,16beta-methylen-testosterone, process for their preparation and agents containing these steroids |
-
1971
- 1971-02-24 DE DE2109555A patent/DE2109555C3/en not_active Expired
-
1972
- 1972-02-03 DK DK46972AA patent/DK130987B/en unknown
- 1972-02-17 ZA ZA721052A patent/ZA721052B/en unknown
- 1972-02-21 CS CS7705*A patent/CS167346B2/cs unknown
- 1972-02-21 CH CH242872A patent/CH581149A5/xx not_active IP Right Cessation
- 1972-02-21 GB GB794372A patent/GB1383334A/en not_active Expired
- 1972-02-21 CS CS1097A patent/CS167345B2/cs unknown
- 1972-02-22 FI FI720473A patent/FI49029C/en active
- 1972-02-22 ES ES400056A patent/ES400056A1/en not_active Expired
- 1972-02-22 NO NO532/72A patent/NO135527C/no unknown
- 1972-02-23 SE SE7202242A patent/SE377338B/xx unknown
- 1972-02-23 HU HUSC377A patent/HU162901B/hu unknown
- 1972-02-23 FR FR7206063A patent/FR2126334B1/fr not_active Expired
- 1972-02-23 AU AU39293/72A patent/AU456892B2/en not_active Expired
- 1972-02-23 DD DD161073A patent/DD96065A5/xx unknown
- 1972-02-23 AT AT147172A patent/AT315393B/en not_active IP Right Cessation
- 1972-02-23 AT AT403073A patent/AT323349B/en not_active IP Right Cessation
- 1972-02-23 IL IL38828A patent/IL38828A/en unknown
- 1972-02-24 IE IE232/72A patent/IE36121B1/en unknown
- 1972-02-24 US US00229205A patent/US3749742A/en not_active Expired - Lifetime
- 1972-02-24 BE BE779797A patent/BE779797A/en unknown
- 1972-02-24 CA CA135,480A patent/CA963000A/en not_active Expired
- 1972-02-24 NL NL7202466A patent/NL7202466A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7202466A (en) | 1972-08-28 |
| IL38828A0 (en) | 1972-04-27 |
| AT315393B (en) | 1974-05-27 |
| CS167345B2 (en) | 1976-04-29 |
| FR2126334A1 (en) | 1972-10-06 |
| DE2109555C3 (en) | 1980-10-30 |
| DK130987C (en) | 1975-10-06 |
| HU162901B (en) | 1973-04-28 |
| FI49029C (en) | 1975-03-10 |
| CA963000A (en) | 1975-02-18 |
| ZA721052B (en) | 1972-10-25 |
| BE779797A (en) | 1972-08-24 |
| FR2126334B1 (en) | 1975-03-14 |
| IE36121B1 (en) | 1976-08-18 |
| CH581149A5 (en) | 1976-10-29 |
| FI49029B (en) | 1974-12-02 |
| CS167346B2 (en) | 1976-04-29 |
| DE2109555A1 (en) | 1972-09-07 |
| AU456892B2 (en) | 1974-12-16 |
| SE377338B (en) | 1975-06-30 |
| AU3923372A (en) | 1973-08-23 |
| ES400056A1 (en) | 1974-12-16 |
| DD96065A5 (en) | 1973-03-05 |
| DK130987B (en) | 1975-05-12 |
| US3749742A (en) | 1973-07-31 |
| IE36121L (en) | 1972-08-24 |
| NO135527C (en) | 1977-04-20 |
| AT323349B (en) | 1975-07-10 |
| IL38828A (en) | 1975-12-31 |
| DE2109555B2 (en) | 1980-03-06 |
| NO135527B (en) | 1977-01-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |