GB932857A - Steroid compounds and compositions thereof - Google Patents
Steroid compounds and compositions thereofInfo
- Publication number
- GB932857A GB932857A GB12797/61A GB1279761A GB932857A GB 932857 A GB932857 A GB 932857A GB 12797/61 A GB12797/61 A GB 12797/61A GB 1279761 A GB1279761 A GB 1279761A GB 932857 A GB932857 A GB 932857A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- compounds
- hydroxy
- keto
- amine
- 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
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero 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 compounds having the formulae: <FORM:0932857/IV(a)/1> and <FORM:0932857/IV(a)/2> and the corresponding D 1,4, D 1,4,6 and D 4,6 compounds, wherein X is hydrogen, hydroxyl or an acylated hydroxyl, the acyl group being derived from monocarboxylic acids containing 1-10 carbon atoms and R2 and R3 are the same or different and represent hydrogen, or alkyl groups containing 1-4 carbon atoms or together with a nitrogen atom form a heterocyclic ring; and pharmaceutically acceptable acid addition salts and quaternary alkyl ammonium derivatives thereof, and therapeutic compositions thereof. The D 1,4- and D 1,4,6-compounds in which R2 and R3 are both alkyl groups or form a heterocyclic ring are obtained by reacting the corresponding progesterone derivative with an amine addition salt and formaldehyde. For D 4- and D 4,6-, and also D 1,4- and D 1,4,6-compounds in which R2 and R3 are hydrogens, the 3-hydroxy compound is reacted with an amine salt and formaldehyde to form a 3-hydroxy-21-dimethylamino-methyl compound, a molecule of dimethylamine is eliminated by forming a quaternary ammonium compound which is treated with water or aqueous alkali to form a 21-methylene compound, the 3-hydroxy group is oxidised to 3-keto and the resulting compound is treated with ammonia or free amine to form the desired 3-keto-D 4-21-substituted compound. For the preparation of 6-bromo or chloro or 6-methyl compounds pregnenolone or 17-hydroxypregnenolone is treated with a peracid to form a 5a ,6a -epoxide, the epoxide ring is opened with CH3MgBr, HCI, or HBr to form 5a -hydroxy-6b -methyl, 5a -hydroxy-6b -chloro and 5a -hydroxy-6b -bromo steroids, which are converted to 21-methylene compounds as above, oxidised with chromic acid and dehydrated to form 3-keto-D 4-21-methylene compounds and reacted with ammonia or an amine to obtain the desired 3-keto-D 4,6-substituted 21-amino compounds. For the preparation of 6-fluoro compounds, pregnenolone or 17-hydroxypregnenolone is reacted with N-bromoacetamide and anhydrous HF to obtain a 5a -bromo-6b -fluoro compound, this compound is converted to a 21-methylene compound as above, the 3-hydroxy group is oxidised to 3-keto, the bromine atom removed with alkaline agent and the resulting 3-keto-D 4-6b -fluoro-21-methy-lene compound is reacted with an amine to produce a 21-amino compound. Double bonds may be introduced in the intermediate 21-methylene compounds in 1,2-position with selenium dioxide or in 6,7-position with chloranil. The therapeutic compositions, having progestational activity, comprise the active compounds of a pharmaceutical carrier. Specifications 897,839 and 924,981 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28181A US3033855A (en) | 1960-05-11 | 1960-05-11 | 21-aminomethyl derivatives of progesterone |
Publications (1)
Publication Number | Publication Date |
---|---|
GB932857A true GB932857A (en) | 1963-07-31 |
Family
ID=21842018
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB12797/61A Expired GB932857A (en) | 1960-05-11 | 1961-04-10 | Steroid compounds and compositions thereof |
Country Status (2)
Country | Link |
---|---|
US (1) | US3033855A (en) |
GB (1) | GB932857A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3627756A (en) * | 1970-04-23 | 1971-12-14 | Searle & Co | N-dialkylaminoalkyl-n-(2{62 ,19-epoxy-5{60 -androstan-17{62 -yl)amines/formamides and 3{60 -halo derivatives thereof |
US4197296A (en) * | 1977-03-23 | 1980-04-08 | Glaxo Group Limited | Androstanes |
-
1960
- 1960-05-11 US US28181A patent/US3033855A/en not_active Expired - Lifetime
-
1961
- 1961-04-10 GB GB12797/61A patent/GB932857A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US3033855A (en) | 1962-05-08 |
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