GB1096732A - Novel 16-alkyl-steroids - Google Patents
Novel 16-alkyl-steroidsInfo
- Publication number
- GB1096732A GB1096732A GB727765A GB727765A GB1096732A GB 1096732 A GB1096732 A GB 1096732A GB 727765 A GB727765 A GB 727765A GB 727765 A GB727765 A GB 727765A GB 1096732 A GB1096732 A GB 1096732A
- Authority
- GB
- United Kingdom
- Prior art keywords
- keto
- reduction
- ones
- formula
- alkyl
- 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
-
- 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
- A61K31/569—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 substituted in position 17 alpha, e.g. ethisterone
-
- 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
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Abstract
Novel steroids of the Formula I <FORM:1096732/C2/1> <FORM:1096732/C2/2> (wherein R1 is H2 or O; R2 is OH or O-acyl; R3 is H or C1- 4 alkyl, alkenyl or alkynyl or R2 + R3 is keto; P is H, CH3 or C2H5; and Q is H, CH3 or C2H5) are prepared by separating the 16a -isomer from steroid mixtures of the Formula II (wherein X is a lower hydrocarbon radical) by extraction, crystallization or chromatography and converting this isomer to the D 4-3-keto-estrene by Birch reduction (the order of these processes can be reversed) followed, when required, by removel of the 3-keto group and/or introduction or interconversion of 17-substitutents by known methods, such as, for 3-keto removal, thioketalization and reductive splitting, and, for 17-position transformations, oxidation of 17b -ols to 17-ones, condensation of 17-ones with hydrocarbon metal compounds to give 17a -hydrocarbon-17b -ols (when it may be necessary to protect the 3-keto group, e.g. by enol ether formation), 17-ol esterification, and reduction of 17a -alkynes to alkenes and alkanes. Starting materials of the Formula II are prepared by reduction of the corresponding 16-methylene compounds or by reaction of 16-unsubstituted 17-ones with oxalyl esters and treatment of the product with an alkyl halide. This reduction may be preceded by the 17-position transformations detailed above.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6402049A NL6402049A (en) | 1964-02-29 | 1964-02-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1096732A true GB1096732A (en) | 1967-12-29 |
Family
ID=19789441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB727765A Expired GB1096732A (en) | 1964-02-29 | 1965-02-19 | Novel 16-alkyl-steroids |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE660312A (en) |
| BR (1) | BR6567566D0 (en) |
| CH (1) | CH495965A (en) |
| DE (1) | DE1543266A1 (en) |
| DK (1) | DK116508B (en) |
| FR (1) | FR1453828A (en) |
| GB (1) | GB1096732A (en) |
| NL (1) | NL6402049A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082780A (en) * | 1975-11-27 | 1978-04-04 | Takeda Chemical Industries, Ltd. | Estradiol derivatives |
| US8003783B2 (en) | 2003-03-24 | 2011-08-23 | Sterix Limited | 17B-hydroxysteroid dehydrogenase inhibitors |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2100319C3 (en) * | 1970-01-07 | 1974-10-31 | Takeda Chemical Industries, Ltd., Osaka (Japan) | New estran compounds, their manufacture and medicinal products containing them |
-
1964
- 1964-02-29 NL NL6402049A patent/NL6402049A/xx unknown
-
1965
- 1965-02-19 GB GB727765A patent/GB1096732A/en not_active Expired
- 1965-02-24 CH CH249865A patent/CH495965A/en not_active IP Right Cessation
- 1965-02-26 BE BE660312D patent/BE660312A/ unknown
- 1965-02-26 DE DE1965N0026296 patent/DE1543266A1/en active Pending
- 1965-02-26 BR BR16756665A patent/BR6567566D0/en unknown
- 1965-02-27 FR FR7317A patent/FR1453828A/en not_active Expired
- 1965-03-01 DK DK104865A patent/DK116508B/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082780A (en) * | 1975-11-27 | 1978-04-04 | Takeda Chemical Industries, Ltd. | Estradiol derivatives |
| US8003783B2 (en) | 2003-03-24 | 2011-08-23 | Sterix Limited | 17B-hydroxysteroid dehydrogenase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1453828A (en) | 1966-09-30 |
| CH495965A (en) | 1970-09-15 |
| BE660312A (en) | 1965-08-26 |
| DK116508B (en) | 1970-01-19 |
| NL6402049A (en) | 1965-08-30 |
| DE1543266A1 (en) | 1969-11-06 |
| BR6567566D0 (en) | 1973-08-02 |
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