GB909126A - 16ª--17ª--alkylidenedioxy steroids and process for preparation - Google Patents
16ª--17ª--alkylidenedioxy steroids and process for preparationInfo
- Publication number
- GB909126A GB909126A GB836659A GB836659A GB909126A GB 909126 A GB909126 A GB 909126A GB 836659 A GB836659 A GB 836659A GB 836659 A GB836659 A GB 836659A GB 909126 A GB909126 A GB 909126A
- Authority
- GB
- United Kingdom
- Prior art keywords
- steroids
- hal
- prepared
- dione
- halo
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises steroids of the formula <FORM:0909126/IV (b)/1> (wherein :Cc-Cd-Ceis :C(a Hal).CH(OH). CH2-, :CH.CH(OH).CH(a Hal)-, :C(a Hal). CO.CH2-, :CH.CO.CH(a Hal)-, :C=CH-CH2, :C-CH=CH-, <FORM:0909126/IV (b)/2> :CH-CO.CH2-, :CH.CH(a or b OH).CH2-, <FORM:0909126/IV (b)/3> or :C(a Hal).CH(O alkanoyl). CH2-, A and B are hydrogen atoms or alkyl groups, Ca-Cb is -CH2CH2-, -CH=CH-, -CH2CH(CH3)- or -CH=C(CH3)- and Y is CH3, CH2OH or CH2O alkanoyl, the alkyl and alkanoyl groups each containing at most 6 carbon atoms); and their preparation (1) by reacting the corresponding 16 : 17-dihydroxy steroids with the appropriate aldehyde or ketone; (2) for compounds wherein the substituents in the 9:11-positions are 9a -halo-11b -hydroxy or 9b :11b -oxido by treating the corresponding 9(11)-unsaturated steroids with an N-halo-succinimide or -acetamide in presence of an acid, dehydrohalogenating if desired to form the 9b :11b -oxido steroids and if desired reacting these with the appropriate halo acid to form the 9a -halo-11b -hydroxy steroids again; (3) for compounds wherein Ca-Cb is CH=CH-, by halogenating the corresponding 2-alkoxyoxalyl-3-keto-D 4-16a :17a -alkylidenedioxy steroid, heating the resulting mixture with a base and dehydrohalogenating e.g. with a tertiary amine; (4) for compounds wherein the substituent in the 11-position is a keto group, by treating the corresponding 11-hydroxy steroids with chromic anhydride; and (5) for 21-alkanoyloxy-steroids, by acylation of the corresponding 21-hydroxysteroids. Detailed examples are given and the hydrolysis of a 21-acylate to a 21-ol also is described. 16a :17a -Dihydroxy-steroids are prepared by hydroxylation of the corresponding D 16-steroids, for example by osmylation and hydrolysis. 2 - Ethoxyoxalyl - 16a :17a - isopropylidenedioxy-4:9(11)-pregnadiene-3:20-dione is prepared from the corresponding 2-unsubstituted steroid and ethyl oxalate. 11b - Acetoxy - 9a - fluoro - 16a :17a :21-trihydroxy-1:4-pregnadiene-3:20-dione is prepared by partial hydrolysis of the 11b :16a :21-triacetoxy compound. 11a - Methanesulphonyloxy - 16a :17a - iso - propylidenedioxy-4-pregnene-3:20-dione is prepared from the 11a -hydroxy compound and methanesulphonyl chloride. 9a - Bromo - 11b :16a :17a -trihydroxy-4-pregnene-3:20-dione is prepared from the D 9(11)-compound and N-bromosuccinimide. Reference has been directed by the Comptroller to Specification 889,765.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72056458A | 1958-03-11 | 1958-03-11 | |
| US742742A US2990401A (en) | 1958-06-18 | 1958-06-18 | 11-substituted 16alpha, 17alpha-substituted methylenedioxy steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB909126A true GB909126A (en) | 1962-10-24 |
Family
ID=27110277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB836659A Expired GB909126A (en) | 1958-03-11 | 1959-03-11 | 16ª--17ª--alkylidenedioxy steroids and process for preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB909126A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0072989A1 (en) * | 1981-08-21 | 1983-03-02 | Schering Aktiengesellschaft | Corticoids, their preparation and their utilization |
| US4404200A (en) * | 1980-12-04 | 1983-09-13 | Aktiebolaget Draco | 4-Pregnene-derivatives, a process for their preparation, composition and method for the treatment of inflammatory conditions |
-
1959
- 1959-03-11 GB GB836659A patent/GB909126A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4404200A (en) * | 1980-12-04 | 1983-09-13 | Aktiebolaget Draco | 4-Pregnene-derivatives, a process for their preparation, composition and method for the treatment of inflammatory conditions |
| EP0072989A1 (en) * | 1981-08-21 | 1983-03-02 | Schering Aktiengesellschaft | Corticoids, their preparation and their utilization |
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