GB1094390A - Preparation of í¸-pregnatriene compounds - Google Patents
Preparation of í¸-pregnatriene compoundsInfo
- Publication number
- GB1094390A GB1094390A GB5015765A GB5015765A GB1094390A GB 1094390 A GB1094390 A GB 1094390A GB 5015765 A GB5015765 A GB 5015765A GB 5015765 A GB5015765 A GB 5015765A GB 1094390 A GB1094390 A GB 1094390A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- pregnatetraen
- hydroperoxy
- cycloethylenedioxy
- pregnen
- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- 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
- C07J15/00—Stereochemically pure steroids containing carbon, hydrogen, halogen or oxygen having a partially or totally inverted skeleton, e.g. retrosteroids, L-isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
D 1,3,5(10) - 19 - nor - 9b ,17a - pregnatrienes and 17a - (hydroxy or hydroperoxy) - D 1,3,5(10) - 19 - nor-9b -pregnatrienes are prepared by hydrogenation of the corresponding D 9(11)-pregnatetraenes with approximately one molar equivalent of hydrogen in the presence of a catalyst consisting of or containing a metal of Group VIII of the Periodic Chart. 20 - Cycloethylenedioxy - 3 - methoxy - D 1,3,5(10),9(11) - 19 - nor - 17a - pregnatetraene is prepared by the sequence D 5-pregnen-3b ,17a ,19, 20b -tetrol (by reduction of 20-one, prepared in turn by saponification of the 17-acetate) --> 3,19,20 - triacetate --> D 5 - 17a - pregnene - 3b , 19 - diol - 20 - one diacetate --> 20 - ketal --> D 4 - 3 - one --> 20 - cycloethylenedioxy - D 4-17a - pregnen - 3 - one - 19 - acid --> 20 - cycloethylenedioxy - D 1,3,5(10),9(11) - 19 - nor - 17a -pregnatetraen-3-ol \-required 3-ether. 3 - Methoxy - D 1,3,5(10),9(11) - 19 - nor - 17a -pregnatetraen - 20 - one is prepared from the free 3-ol, prepared in turn by the sequence D 5 - 17a - pregnene - 3b ,19-diol - 20 - one diacetate --> D 4 - 17a - pregnen - 19 - ol - 3,20 -dione --> 19-oic acid --> required product. The corresponding 16a -methyl compounds are prepared similarly. D 1,3,5(10),9(11) - 19 - nor - pregnatetraene - 3,17a -diol-20-one is prepared from D 4-pregnen-17a -ol-3,20-dione - 19 - oic acid, itself prepared from the 19-ol. D 1,3,5(10),9(11) - 19 - nor - pregnatetraen - 3 - ol - 20 - one is prepared similarly, and is converted to the 3-tetrahydropyranyl ether, this to 3 - tetrahydropyranyloxy - 17a - hydroperoxy - D 1,3,5(10),9(11) - 19 - nor - pregnatetraen-20-one and this to 17a -hydroperoxy-D 1,3,5(10),9(11) -19-nor-pregnatetraen-3-ol-20-one. D 1,3,5(10),9(11) - 19 - nor - pregnatetraene - 3,17a , 20b -triol is prepared by reduction of the 20-one, and both are converted to the 3-hydroxyethoxy ethers. 3 - Methoxy - D 1,3,5(10),9(11) - 19 - nor - pregnatetraen-17a -ol-20-one and the 20b -ol are prepared by etherification of the 3-ols. The 20b -ol is then converted to the 20-acetate. By similar methods are prepared 16a -methyl-D 1,3,5(10),9(11)\h - 19 - nor -pregatetraen - 3 - ol - 20-one and the 17a -hydroperoxy derivative thereof. The first named of these is then converted to the 3-methylether and this to the 17a -hydroperoxy derivative. The 16b -methyl compounds are prepared similarly. 3 - Methoxy - 20 - cycloethylenedioxy - D 1,3,5(10),9(11) - 19 - nor - pregnatetraen-17a -ol is prepared by ketalization.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41692664A | 1964-12-08 | 1964-12-08 | |
| US41691364A | 1964-12-08 | 1964-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1094390A true GB1094390A (en) | 1967-12-13 |
Family
ID=27023527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5015765A Expired GB1094390A (en) | 1964-12-08 | 1965-11-25 | Preparation of í¸-pregnatriene compounds |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH462156A (en) |
| DE (1) | DE1493125A1 (en) |
| GB (1) | GB1094390A (en) |
| NL (1) | NL6515930A (en) |
-
1965
- 1965-11-25 GB GB5015765A patent/GB1094390A/en not_active Expired
- 1965-12-01 DE DE19651493125 patent/DE1493125A1/en active Pending
- 1965-12-08 NL NL6515930A patent/NL6515930A/xx unknown
- 1965-12-08 CH CH1690065A patent/CH462156A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1493125A1 (en) | 1969-08-07 |
| CH462156A (en) | 1968-09-15 |
| NL6515930A (en) | 1966-06-09 |
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