GB942663A - Phenyl cyclohexane and -cyclohexene derivatives, new intermediates for the synthesis of the female sex hormone estrone and other steroids - Google Patents
Phenyl cyclohexane and -cyclohexene derivatives, new intermediates for the synthesis of the female sex hormone estrone and other steroidsInfo
- Publication number
- GB942663A GB942663A GB1220360A GB1220360A GB942663A GB 942663 A GB942663 A GB 942663A GB 1220360 A GB1220360 A GB 1220360A GB 1220360 A GB1220360 A GB 1220360A GB 942663 A GB942663 A GB 942663A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula shown
- methyl
- treating
- xiv
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula shown in Fig. 1 wherein R is H or CH3, R1 is CN, COOCH3 or COOC2 H5 and R2 is H, CH3 or C2H5 and also wherein RR1 is =H2 or =CHOH and R2, has the above significance; compounds of the formula shewn in Fig. II wherein R is H or CH3 and R1 is CH3 or C2H5 and the position 11 21 is unsaturated; compounds of th formula shown in Fig. IV wherein R is H or CH3; and compounds of the formula shown in Figs. VI, VII, VIII, IX, X, XI, XII, XIII, XIV and XVIII. The invention also comprises methods of preparing (a) a compound of the formula shown in Fig. III by cyclisation of a compound of the formula shown in Fig. XIV wherein R is H, R1 and R2 are selected fro methyl and ethyl by treatment with aqueous alkali; (b) a compound of the formula shown in Fig. XIV by condensing a compound of the formula shown in Fig. XV with a compound of the formula shown in Fig. XVI in the presence of alkoxides selected from sodium and potassium alkoxides and dimethyl sulphate (c) a compound of the formula shown in Fig. III by cyclisation of a compound of the general formula shown in Fig. XIV, wherein R is H, and R1 and R2 are selected from methyl and ethyl cyclisation being carried out by treating the compounds shown in Fig. XIV with alcoholic alkali whereby ketonic fission of the b -keto ester group results in elimination of -COOR, and there occurs saponification o -COOR2 to COOH and the usual aldol condensation occurs followed by elimination of water; (d) a compound of the general formula shown in Fig. II where R=H or CH3 and R1=CH3 or C2H5 by treating a compound of the general formula shown in Fig. XIV wherein R is H or CH3 and R1 and R2 are CH3 or C2H5 with sodium alkoxide whereby cyclisation and saponification occurs; (e) a compound of the formula shown in Fig. IV where R is H by reduction of the compound shewn in Fig. IV with lithium and anhydrous liquid ammonia; (f) a method of preparing a compound of the formul shown in Fig. IV where R is methyl by esterification of a compound of the formula shown in Fig IV where R is H with diazo methane or methanol/sulphuric acid; (g) a compound of the formula shown in Fig. IV where R is H by hydrogenation of the compound shown in Fig. V in the presence o palladium on charcoal catalyst followed by treatment with aqueous or alcoholic alkali; (h) a compound of the formula shown in Fig. VI by formylation of a compound of the formula shown in Fig. with ethyl or methyl formate in the presence of dry sodium alkoxide or potassium alkoxide in dr ether, benzene or petroleum ether; (i) a compound of the formula shown in Fig. VII by a similar process from a compound of the formula shown in Fig. IV; (j) a compound of the formula shown in Fig. XIII by treating a compound of the formula shown in Fig. VI with hydroxyamine hydrochloride in the presence of acetic acid; (k) a compound of the formula shown in Fig. XII by a similar process fro a compound of the formula shown in Fig. VII; (l) a compound of the formula shown in Fig. VII by treating a compound of the formula shown in Fig. XIII with sodium alkoxide or potassium alkoxide and a methyl halide; (m) a compound of the formula shown in Fig. IX by a similar process from a compound of the formula shown in Fig. XII; (n) a compound of the formula shown in Fig. X b treating a compound of the formula shown in Fig VIII with potassium carbonate in aqueous methanol; (o) a compound of the formula shown in Fig. XI by a similar process from a compound of the formula shown in Fig. IX; (p) a compound of the formula shown in Fig. XVII by reduction of a compound of the formula shown in Fig. X with lithium and anhydrous liquid ammonia followed by treatment with methanolic hydrogen chloride; (q) a compound of the formula shown in Fig. XVII by treatment of a compound of the formula shown in Fig. XI with methanolic hydrogen chloride; (r) a compound of the formula shown in Fig. XVIII by esterification of a compound of the formula shown in Fig. II in which R is H, R1 is C2H5 with diazomethane followed by methylation with sodium, sodium alkoxide or potassium alkoxide or sodium hydride and a methyl halide; (s) a compound of the formula shown in Fig. XVIII by esterification of a compound of the formula shown in Fig. II where R is CH3 and R1 is C2H5; (t) a compound of the formula shown in Fig. XVII comprising treating dimethyl, diethyl or ethyl methyl b -keto-adipate with b -dimethylamino-p-methoxypropiophenone hydrochloride to form a compound of the general formula shown in Fig. XIV wherein R is H and R1 and R2 are methyl or ethyl radicals, cyclising to form a compound of the formula shown in Fig. III by treatment with aqueous alkali, esterifying to form the methyl ester, formylating with methyl or ethyl formate in the presence of sodium- or potassium alkoxide to form a compound of the formula shown in Fig. VI, treating the latter with hydroxylamine hydrochloride in acetic acid to form a compound of the formula shown in Fig. XIII treating the latter with alkali alkoxide and a methyl halide to form a compound of the formula shown in Fig. VIII which is partially hydrolysed by treatment with potassium carbonate in aqueous methanol to produce a compound of the formula shown in Fig. X, reducing the latter compound with lithium and anhydrous ammonia followed by treatment with methanolic hydrogen chloride, and (u) a compound of the formula shown in Fig. XI by the reductio of the compound of the formula shown in Fig. X by lithium and anhydrous ammonia. Examples are furnished. Specification 942,664 is referred to. <FORM:0942663/C2/1>
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1220360A GB942663A (en) | 1960-04-06 | 1960-04-06 | Phenyl cyclohexane and -cyclohexene derivatives, new intermediates for the synthesis of the female sex hormone estrone and other steroids |
GB4137262A GB942664A (en) | 1960-04-06 | 1960-04-06 | Improved methods of producing dimethyl ª -ketoadipate and dimethyl ª -methyl ª -ketoadipate |
DEJ18198A DE1134985B (en) | 1960-04-06 | 1960-05-25 | Process for the production of precursors for OEstrons |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1220360A GB942663A (en) | 1960-04-06 | 1960-04-06 | Phenyl cyclohexane and -cyclohexene derivatives, new intermediates for the synthesis of the female sex hormone estrone and other steroids |
Publications (1)
Publication Number | Publication Date |
---|---|
GB942663A true GB942663A (en) | 1963-11-27 |
Family
ID=10000232
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1220360A Expired GB942663A (en) | 1960-04-06 | 1960-04-06 | Phenyl cyclohexane and -cyclohexene derivatives, new intermediates for the synthesis of the female sex hormone estrone and other steroids |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1134985B (en) |
GB (1) | GB942663A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012140243A1 (en) * | 2011-04-15 | 2012-10-18 | Laboratoire Biodim | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
US9994509B2 (en) | 2013-07-05 | 2018-06-12 | Hivih | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
-
1960
- 1960-04-06 GB GB1220360A patent/GB942663A/en not_active Expired
- 1960-05-25 DE DEJ18198A patent/DE1134985B/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012140243A1 (en) * | 2011-04-15 | 2012-10-18 | Laboratoire Biodim | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
US9604900B2 (en) | 2011-04-15 | 2017-03-28 | Laboratoire Biodim | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
US9994509B2 (en) | 2013-07-05 | 2018-06-12 | Hivih | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
Also Published As
Publication number | Publication date |
---|---|
DE1134985B (en) | 1962-08-23 |
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