http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-887721-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_7780e9d205ef3d354fe484bbc65b155c |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J1-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J1-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 |
| filingDate | 1958-04-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1962-01-24-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-887721-A |
| titleOfInvention | Cyclopentanophenanthrene derivatives |
| abstract | The invention comprises 19-androstenes of the formula <FORM:0887721/IV (b)/1> wherein R is an alkyl, alkenyl or alkinyl group containing not more than six carbon atoms, R1 and R2 each represent hydrogen or a hydrocarbon carboxylic acyl group of from 2-12 carbons atoms, and their preparation from the corresponding 17a -alkyl or alkinyl derivative of 19-nor-D 4-androsten-17b -ol-3-one by enol esterification, selective hydrolysis of the enol ester group and reduction of the D 3 bond with an alkali metal double hydride, preferably with sodium borohydride and optionally saponifying 17-ester group, hydrogenating a 17-alkinyl group to the corresponding 17-alkenyl or alkyl group and acylating either or both the 3- and 17-hydroxy groups. The enol esterification is effected with isopropenyl acetate or with an acid anhydride and an acid catalyst, and specified acyl groups are acetyl, propinyl, butyroyl, hemisuccinyl, caproyl, benzoyl, trimethylacetyl, phenoxyacetyl, phenoxypropionyl, phenylpropionyl, cyclopentylpropionyl, dichlorophenoxyacetyl, and b -chloropropionyl. The saponification process is preferably conducted with lithium aluminium hydride. In examples: (1) 17a -methyl-19-nor-testosterone is refluxed with acetic anhydride and pyridine, the resulting acetate heated with isopropenyl acetate and H2SO4 and the diacetate of 17a -methyl-19-nor-D 3,5-androstadiene 3b ,17b -diol reduced with NaBH4 and saponified with ethereal LiAlH4 to 17a -methyl-19-nor-D 5-androstene-3b ,17b -diol, characterised (2) to (4) as its 3-acetate, 3,17-diacetate, and 3-propionate-17-acetate; (5) 17a -ethinyl-19-nortestosterone treated as in (1) gives 17a -ethinyl-19-nor-D 5 androstene-3b ,17b -diol which (6) is hydrogenated over Pd on CaCO3 to the 17a -vinyl compound and then over Pd on charcoal to 17a - ethyl - 19 - nor - D 5 - androstene - 3b , 17b - diol; (8) and (9) the 17-acetate of the 17a -ethinyl compound is similarly reduced in two stages; (10) 17a -ethinyl-19-nor-testosterone is heated with acetic anhydride and p-toluene sulphonic acid giving the diacetate of 17a -ethinyl-19-nor-D 3,5-androstadiene-3,17b -diol; (11) and (12), the dipropionate is likewise obtained and converted to the 17-propionate of 17a -ethinyl-19-nor-D 5-androstene-3b ,17b -diol, and its 17-vinyl and 17-ethyl analogues; (13) to (15) and (19) illustrate similar reactions with 17a -propionyl-, and 17a -butinyl compounds; (16) to (18) 17a -ethinyl-19-nor-D 5 androstene-3b ,17b -diol is characterised as its 3-acetate, 3,17-diacetate, and 3-propionate-17-acetate. |
| priorityDate | 1957-04-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 48.