GB1425636A - 15alpha,16alpha-methylene-delta4-oestren-17beta-ols - Google Patents
15alpha,16alpha-methylene-delta4-oestren-17beta-olsInfo
- Publication number
- GB1425636A GB1425636A GB682173A GB682173A GB1425636A GB 1425636 A GB1425636 A GB 1425636A GB 682173 A GB682173 A GB 682173A GB 682173 A GB682173 A GB 682173A GB 1425636 A GB1425636 A GB 1425636A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methylene
- dimethyl
- propylenedioxy
- prepared
- methyl
- 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
- A61K31/567—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 position 17 alpha, e.g. mestranol, norethandrolone
-
- 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
-
- 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
-
- 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
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
1425636 15,16 - Methylene - estr - 4 - enes SCHERING AG 12 Feb 1973 [11 Feb 1972] 6821/73 Heading C2U [Also in Division A5] Novel steroids of the formula wherein R<SP>1</SP> is C 1-5 alkyl; R<SP>2</SP> is H or acyl; R<SP>3</SP> is H or an optionally substituted aliphatic hydrocarbon group of at most 5 carbon atoms (exclusive of substituents); and X is O or H (OR<SP>4</SP>) in which OR<SP>4</SP> is in the alpha or beta position and R<SP>4</SP> is H or acyl are prepared from steroids of the formulµ wherein Y is a protected keto group and the dotted lines in the rings indicate the presence of a #<SP>5</SP>- or #<SP>5(10)</SP>-double bond and when a #<SP>5(10)</SP>- double bond is present then the 10-H atom is absent, by reduction in the 17-position or conversion to a 17α-substituted-17#-ol followed when required, by hydrolysis to a free #<SP>4</SP>-3-one and, if desired, by hydrogenation of a 17α- unsaturated group and/or reduction to a 3-ol and/or acylation of a free OH group. 3,3 - (2<SP>1</SP>,2<SP>1</SP> - Dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy)- 18 - methyl - 15α,16α - methylene - #<SP>5</SP> or #<SP>5(10)</SP>- estren-17-one is prepared from 3,3-(2<SP>1</SP>,2<SP>1</SP>-dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy) - 18 - methyl - 19- nor - #<SP>5,16</SP> or <SP>15(10),16</SP> - pregnadien - 20 - one (prepared from the #<SP>4</SP>-3-one and 2,2-dimethyl-1,3- propane-diol) by oxygenation to give the corresponding #<SP>15</SP> - 17α - ol, reduction of this to the corresponding 20-ol, reaction of this with methylene iodide in the presence of a Zn-Cu couple to give 17α,20# - dihydroxy - 3,3 - (2<SP>1</SP>,2<SP>1</SP>- dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy) - 18 - methyl- 15α,16α - methylene - 19 - nor - #<SP>5</SP>- or #<SP>5(10)</SP>- pregnene and oxidation of this. 3,3-(2<SP>1</SP>,2<SP>1</SP> -dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy) - 15α,16α- methylene - #<SP>5</SP> or <SP>15(10)</SP> - estren - 17 - one is prepared similarly via corresponding intermediates. The novel steroids are stated to possess a strong androgenic and anabolic activity or a strong gestagenic activity and they may be made up into pharmaceutical compositions with suitable carriers. The gestagenic compounds can be used, possibly together with estrogens, in contraceptive preparations (see Heading A5B).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2207421A DE2207421C3 (en) | 1972-02-11 | 1972-02-11 | 15?, 16? -Methylene-4-oestrene-17? -ols or acylates, processes for their production and medicaments containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1425636A true GB1425636A (en) | 1976-02-18 |
Family
ID=5836211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB682173A Expired GB1425636A (en) | 1972-02-11 | 1973-02-12 | 15alpha,16alpha-methylene-delta4-oestren-17beta-ols |
Country Status (29)
| Country | Link |
|---|---|
| JP (1) | JPS5829317B2 (en) |
| KR (1) | KR780000156B1 (en) |
| AT (1) | AT327413B (en) |
| AU (1) | AU467306B2 (en) |
| BE (1) | BE795241A (en) |
| CA (1) | CA997753A (en) |
| CH (2) | CH590883A5 (en) |
| CS (1) | CS193019B2 (en) |
| DD (1) | DD102379A5 (en) |
| DE (1) | DE2207421C3 (en) |
| DK (1) | DK131037B (en) |
| EG (1) | EG10914A (en) |
| ES (1) | ES410933A1 (en) |
| FI (1) | FI52225C (en) |
| FR (1) | FR2181719B1 (en) |
| GB (1) | GB1425636A (en) |
| GR (1) | GR63160B (en) |
| HU (1) | HU165253B (en) |
| IE (1) | IE37266B1 (en) |
| IL (1) | IL41506A (en) |
| NL (1) | NL177217C (en) |
| NO (2) | NO140304C (en) |
| PH (1) | PH9370A (en) |
| PL (1) | PL81084B1 (en) |
| RO (1) | RO73527A (en) |
| SE (3) | SE403781B (en) |
| SU (1) | SU513628A3 (en) |
| YU (1) | YU35035B (en) |
| ZA (1) | ZA73944B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007027637A1 (en) | 2007-06-12 | 2008-12-18 | Bayer Schering Pharma Aktiengesellschaft | 17β-cyano-19-nor-androst-4-ene derivative, its use and the derivative-containing drug |
| DE102007027636A1 (en) | 2007-06-12 | 2008-12-18 | Bayer Schering Pharma Aktiengesellschaft | 17β-Cyano-18α-homo-19-nor-androst-4-ene derivative, its use and the derivative-containing drug |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT274653B (en) * | 1966-11-10 | 1969-09-25 | Alexander Schoeller & Co Kg | Stackable, rectangular, closed plastic transport container for fine-grained bulk goods and liquids |
-
0
- BE BE795241D patent/BE795241A/en not_active IP Right Cessation
-
1972
- 1972-02-11 DE DE2207421A patent/DE2207421C3/en not_active Expired
- 1972-12-29 PL PL1972159970A patent/PL81084B1/pl unknown
-
1973
- 1973-01-11 DD DD168198A patent/DD102379A5/xx unknown
- 1973-01-16 DK DK24273AA patent/DK131037B/en not_active IP Right Cessation
- 1973-01-23 FI FI730169A patent/FI52225C/en active
- 1973-01-24 ES ES410933A patent/ES410933A1/en not_active Expired
- 1973-01-31 YU YU243/73A patent/YU35035B/en unknown
- 1973-01-31 CS CS73748A patent/CS193019B2/en unknown
- 1973-02-06 CA CA163,029A patent/CA997753A/en not_active Expired
- 1973-02-06 IE IE190/73A patent/IE37266B1/en unknown
- 1973-02-07 EG EG49/73A patent/EG10914A/en active
- 1973-02-08 AT AT112473A patent/AT327413B/en not_active IP Right Cessation
- 1973-02-09 GR GR1318A patent/GR63160B/en unknown
- 1973-02-09 FR FR7304678A patent/FR2181719B1/fr not_active Expired
- 1973-02-09 IL IL41506A patent/IL41506A/en unknown
- 1973-02-09 ZA ZA730944A patent/ZA73944B/en unknown
- 1973-02-09 PH PH14330*UA patent/PH9370A/en unknown
- 1973-02-09 CH CH186373A patent/CH590883A5/xx not_active IP Right Cessation
- 1973-02-09 SU SU1891803A patent/SU513628A3/en active
- 1973-02-09 CH CH535776A patent/CH593995A5/xx not_active IP Right Cessation
- 1973-02-09 NO NO528/73A patent/NO140304C/en unknown
- 1973-02-10 KR KR7300246A patent/KR780000156B1/en active
- 1973-02-10 RO RO7373805A patent/RO73527A/en unknown
- 1973-02-10 HU HUSE1666A patent/HU165253B/hu unknown
- 1973-02-12 SE SE7301935A patent/SE403781B/en unknown
- 1973-02-12 GB GB682173A patent/GB1425636A/en not_active Expired
- 1973-02-12 AU AU52076/73A patent/AU467306B2/en not_active Expired
- 1973-02-12 NL NLAANVRAGE7301974,A patent/NL177217C/en not_active IP Right Cessation
- 1973-02-12 JP JP48017357A patent/JPS5829317B2/en not_active Expired
-
1975
- 1975-12-22 SE SE7514513A patent/SE409329B/en not_active IP Right Cessation
-
1977
- 1977-12-07 SE SE7713896A patent/SE426834B/en not_active IP Right Cessation
-
1978
- 1978-08-14 NO NO782754A patent/NO143065C/en unknown
Also Published As
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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 |