GB1426353A - 15alpha,16alpha-methylene-5alpha-androstanes - Google Patents
15alpha,16alpha-methylene-5alpha-androstanesInfo
- Publication number
- GB1426353A GB1426353A GB681973A GB681973A GB1426353A GB 1426353 A GB1426353 A GB 1426353A GB 681973 A GB681973 A GB 681973A GB 681973 A GB681973 A GB 681973A GB 1426353 A GB1426353 A GB 1426353A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methylene
- acetoxy
- prepared
- androstan
- give
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (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)
Abstract
1426353 15,16-Methylene-androstane compounds SCHERING AG 12 Feb 1973 [11 Feb 1972] 6819/73 Heading C2U Novel steroids of the formula (wherein R is H, acyl, C 1-4 alkyl or an oxygencontaining heterocyclic group and C<SP>1</SP>-C<SP>2</SP> is a single or double bond between the 1- and 2- carbon atoms) are prepared by chemical or microbiological oxidation of the corresponding ring A-saturated 3#-hydroxy-steroids containing a protected 17#-hydroxy group, followed, if desired, by #<SP>1</SP>-dehydrogenation (for example by bromination and dehydrobromination) and/or, if desired or necessary, by conversion to a free 17#-ol which if desired may subsequently be esterified or etherified. 17# - Benzoyloxy - 15α,16α - methylene - 5α- androstan-3#-ol is prepared by oxygenating 3#- acetoxy - 5α - pregn - 16 - en - 20 - one to give 17α - hydroxy - 3# - acetoxy - 5α - pregn - 15- en - 20 - one, reducing this to the 20-ol. refluxing this in a solvent with a zinc-copple couple and methylene iodide to give 3#-acetoxy-15α,16α- methylene - 5α - pregnane - 17α,20# - diol, oxidizing this with periodic acid to give 3#-acetoxy- 15α,16α - methylene - 5α - androstan - 17 - one, reducing this to the 17#-ol, converting this to the 17-benzoate and hydrolysing the 3-acetoxy group. 17# - Tetrahydropyranyloxy - 15α,16α- methylene - 5α - androstan - 3# - ol is prepared by hydrolysis of 17#-tetrahydropyranyloxy-3#- acetoxy - 15α, 16α - methylene - 5α - androstane, in turn prepared by etherification of the corresponding 17#-ol. The novel steroids are androgenic and anabolic agents and may be made up into pharmaceutical compositions with suitable carriers.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19722207422 DE2207422A1 (en) | 1972-02-11 | 1972-02-11 | 15ALPHA, 16ALPHA-METHYLENE-5ALPHA-ANDROSTANE |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1426353A true GB1426353A (en) | 1976-02-25 |
Family
ID=5836212
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB681973A Expired GB1426353A (en) | 1972-02-11 | 1973-02-12 | 15alpha,16alpha-methylene-5alpha-androstanes |
Country Status (9)
Country | Link |
---|---|
JP (1) | JPS4886855A (en) |
AT (1) | AT323345B (en) |
BE (1) | BE795239A (en) |
CH (1) | CH588506A5 (en) |
DE (1) | DE2207422A1 (en) |
DK (1) | DK130988B (en) |
FR (1) | FR2181720B1 (en) |
GB (1) | GB1426353A (en) |
NL (1) | NL7301923A (en) |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1643035B2 (en) * | 1967-08-11 | 1976-01-15 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 15BETA, 16BETA-METHYLEN-5ALPHA -ANDROST-L-ENE, PROCESS FOR THEIR MANUFACTURING AND THE PRODUCTS CONTAINED |
-
0
- BE BE795239D patent/BE795239A/en unknown
-
1972
- 1972-02-11 DE DE19722207422 patent/DE2207422A1/en active Pending
-
1973
- 1973-01-16 DK DK24173A patent/DK130988B/en unknown
- 1973-02-08 AT AT112573A patent/AT323345B/en not_active IP Right Cessation
- 1973-02-09 CH CH186273A patent/CH588506A5/xx not_active IP Right Cessation
- 1973-02-09 FR FR7304679A patent/FR2181720B1/fr not_active Expired
- 1973-02-09 NL NL7301923A patent/NL7301923A/xx not_active Application Discontinuation
- 1973-02-12 GB GB681973A patent/GB1426353A/en not_active Expired
- 1973-02-12 JP JP1735673A patent/JPS4886855A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
DK130988C (en) | 1975-10-13 |
CH588506A5 (en) | 1977-06-15 |
FR2181720A1 (en) | 1973-12-07 |
FR2181720B1 (en) | 1975-11-21 |
DK130988B (en) | 1975-05-12 |
JPS4886855A (en) | 1973-11-15 |
AT323345B (en) | 1975-07-10 |
DE2207422A1 (en) | 1973-08-16 |
BE795239A (en) | 1973-08-09 |
NL7301923A (en) | 1973-08-14 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |