GB841411A - New 19-nor-steroid compounds and process for the preparation thereof - Google Patents
New 19-nor-steroid compounds and process for the preparation thereofInfo
- Publication number
- GB841411A GB841411A GB10590/58A GB1059058A GB841411A GB 841411 A GB841411 A GB 841411A GB 10590/58 A GB10590/58 A GB 10590/58A GB 1059058 A GB1059058 A GB 1059058A GB 841411 A GB841411 A GB 841411A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- hydroxy
- prepared
- oestrane
- acetic
- 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
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises compounds of the formulae <FORM:0841411/IV(b)/1> (wherein R is an alkenyl or alkynyl group containing 2 to 6 carbon atoms and R1 is hydrogen or a carboxylic acyl group of at most 10 carbon atoms) and their preparation by reaction of the corresponding 17-keto-steroids with an appropriate organometallic compound derived from the hydrocarbon RH, including Grignard reagents and alkali metal or alkaline earth metal compounds of alkynes formed in situ from the alkyne and an alkali metal or an amide or alcoholate thereof. The esters are prepared by esterification of the free hydroxy compounds, suitable esterifying acids being acetic, propionic, butyric, valeric, caproic, isocaproic, succinic, tartaric, cyclopentyl-acetic, b -cyclopentyl-propionic, cyclohexyl-acetic, gammacyclohexyl-butyric, phenylacetic, b -phenylpropionic and benzoic acids, glycine and phenylalanine. The 17-alkenyl compounds may also be prepared by partial reduction of the 17-alkynyl compounds, preferably with hydrogen and a catalyst such as nickel or palladium on barium or calcium sulphate. Examples are given, the groups R being variously ethynyl, hex-5-ynyl, vinyl, pent-4-eryl, allyl, methylethynyl, propargyl and but-3-enyl. D 4 - and D 5(10) - 17b - hydroxy - oestrene an D 3 : 5 - 17b - hydroxy - oestradiene are all prepared by reduction of oestradiol-3-alkyl-ethers with an alkali metal in the presence of liquid ammonia or an aliphatic primary amine and are all converted to the corresponding 17-oxo compounds by oxidation with chromium trioxide. 17b - hydroxy - oestrane is prepared by catalytic reduction of D 4-17b -hydroxy-oestrane and is similarly converted to 17-oxo-oestrane.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL841411X | 1957-04-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB841411A true GB841411A (en) | 1960-07-13 |
Family
ID=19845017
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10590/58A Expired GB841411A (en) | 1957-04-10 | 1958-04-02 | New 19-nor-steroid compounds and process for the preparation thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB841411A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102225960A (en) * | 2011-04-27 | 2011-10-26 | 长沙楚源生物科技有限公司 | Preparation method of allylestrenol |
CN102675393A (en) * | 2012-04-09 | 2012-09-19 | 浙江仙琚制药股份有限公司 | Method for preparing 19-demethyl-4-androstenedione |
-
1958
- 1958-04-02 GB GB10590/58A patent/GB841411A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102225960A (en) * | 2011-04-27 | 2011-10-26 | 长沙楚源生物科技有限公司 | Preparation method of allylestrenol |
CN102225960B (en) * | 2011-04-27 | 2012-11-07 | 长沙楚源生物科技有限公司 | Preparation method of allylestrenol |
CN102675393A (en) * | 2012-04-09 | 2012-09-19 | 浙江仙琚制药股份有限公司 | Method for preparing 19-demethyl-4-androstenedione |
CN102675393B (en) * | 2012-04-09 | 2014-05-07 | 浙江仙琚制药股份有限公司 | Method for preparing 19-demethyl-4-androstenedione |
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