GB979891A - Process for the production of new steroid compounds - Google Patents
Process for the production of new steroid compoundsInfo
- Publication number
- GB979891A GB979891A GB264961A GB264961A GB979891A GB 979891 A GB979891 A GB 979891A GB 264961 A GB264961 A GB 264961A GB 264961 A GB264961 A GB 264961A GB 979891 A GB979891 A GB 979891A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- gona
- des
- methoxy
- acyloxy
- 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
- C07J61/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by contraction of only one ring by one or two atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/573—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing hydroxy groups
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises 13b -alkyl homologues of pharmacologically active 18-nor estradiol compounds of the natural series, the alkyl group containing at least two carbon atoms, particularly 3, 17b -dihydroxy-13b -n-propyl-18-norestra-1, 3, 5(10)-triene and its 17-benzoate, together with a synthesis of these compounds from a 4, 5-secogon-9-ene-3, 5-dione of the formula:- <FORM:0979891/C1/1> by cyclization in alkaline media, isomerization by heating of the resulting 17b -acyloxy-13b -alkyl-gona-4, 9-dien-3-one to the corresponding 17b -acyloxy-13b -alkyl-3-hydroxy-18-nor estra- 1, 3, 5(10)-triene, saponification and, if desired, subsequent esterification or etherification. The intermediate 4, 5-secogon-9-ene-3, 5-dione is in turn prepared from 6-methoxy-3, 4-dihydronaphthyl-[2, 1-d]-isoxazole by reaction with an alkyl halide, condensation of the resulting 2-alkyl-2-cyano-6-methoxy-tetralone-1 with dimethyl succinate to form the corresponding 13b -alkyl-5-methoxy- 15 - methoxycarbonyl - des: A-gona-5, 7, 9, 14-tetraene-17-one, reaction of the latter with an alkali metal mixed hydride to effect simultaneous reduction and saponification to form a racemate of 13b -alkyl-5-methoxy-17b -hydroxy-des: A-gona-5, 7, 9, 14-tetraen-15-carboxylic acid, resolution of the racemate and removal of the carbonyl substituent from the separated laevo-rotatory enanteomorph by means of mineral acid to form the corresponding 13b -alkyl-17b -hydroxy-5-methoxy-des: A-gona-5, 7, 9, 14-tetraene, reduction of the 14-double bond by catalytic hydrogenation followed by reaction with an alkali metal in liquid ammonia to form a 13b -alkyl-17b -hydroxy-des: A-gon-9-en-5-one, esterification of the latter at C17 and reaction with pyrrolidine to form 5-pyrrolidyl-17b -acyloxy-des: A-gona-5(10), 9(11)-diene, followed by condensation with a 1, 3-dihalogeno-2-butene to form the corresponding 17b -acyloxy-13b -alkyl-3-halogeno-4, 5-secogona-2, 9-dien-5-one, which upon acid hydrolysis yields the desired intermediate. The complete synthesis is illustrated by a detailed example. The novel compounds exhibit a powerfyl estrogenic action. Specifications 914,732, 979,892, 979,895, 979,896, 979,897 and 979,898 are referred to.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR816402A FR1257033A (en) | 1960-01-22 | 1960-01-22 | 2-cyano-6-methoxy tetralone-1 alkylation process in position 2 |
| FR832449A FR1365257A (en) | 1960-07-08 | 1960-07-08 | Novel 19-nor-testosterone analogue, esters thereof and method of preparation |
| FR837026A FR1365262A (en) | 1960-08-29 | 1960-08-29 | New analogue of estradiol, its functional derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB979891A true GB979891A (en) | 1965-01-06 |
Family
ID=27245385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB264961A Expired GB979891A (en) | 1960-01-22 | 1961-01-23 | Process for the production of new steroid compounds |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE599343A (en) |
| CH (1) | CH395982A (en) |
| ES (1) | ES263632A1 (en) |
| GB (1) | GB979891A (en) |
-
1960
- 1960-12-28 ES ES0263632A patent/ES263632A1/en not_active Expired
-
1961
- 1961-01-20 BE BE599343A patent/BE599343A/en unknown
- 1961-01-20 CH CH68361A patent/CH395982A/en unknown
- 1961-01-23 GB GB264961A patent/GB979891A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH395982A (en) | 1965-07-31 |
| ES263632A1 (en) | 1961-06-01 |
| BE599343A (en) | 1961-07-20 |
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