http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-988801-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_4acae202b6a15394281949545e70d2f6 |
| classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/H01M2300-0051 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J5-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J9-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J9-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J5-00 |
| filingDate | 1962-01-24-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1965-04-14-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-988801-A |
| titleOfInvention | New steroid compounds and processes for their preparation and conversion into pharmacologically-useful compounds |
| abstract | The invention comprises lower alkyl esters of 20 - carboalkoxy - 5b - pregnan - 11 - on - 21 - oic acids, having the general formula <FORM:0988801/C2/1> wherein R1 represents a hydrogen atom or an oxacyclic group, R1 and R3 are the same and each represents an alkyl group having 1-6 carbon atoms, and R4 is a hydrogen atom or a benzyl group and processes for the preparation thereof (a) wherein R4 is a hydrogen atom by reacting a 20-carboalkoxy-5b -pregnan-11-on-21-oic acid ester with formaldehyde to form the corresponding 20 - carboalkoxy - 20 - hydroxy-methylene - 5b - pregnan - 11 - one - 21 - oic acid - 5b - pregnan - 11 -one - 21 - oic acid ester; (b) wherein R4 is a benzyl group, by reacting a 3#c-acyloxy-20-carboalkoxy-5b -pregnan-11-on-21-oic acid alkyl ester with an alkali metal to give the corresponding alkali metal derivative at the 20-position, and condensing the latter with benzyloxychloromethane to form the corresponding 3#c - oxacyclo - 20 - carbo-alkoxy - 20 - benzyloxy - methylene -5b - pregnan - 11 -on - 21 - oic acid alkyl ester. The 3#c - oxacyclo - 20 - carbalkoxy - 5b - pregnan11-on-21-oic acid alkyl ester is obtained by reacting a 3#c-acyloxy-5b -androstane-11,17-dione with a cyanoacetic acid lower alkyl ester (1-6 carbon atoms) to obtain 3#c-acyloxy-20-cyano - 5b - pregn - 17(20) - en : 11 - on - 21-oic acid alkyl ester, catalytically hydrogenating the latter to obtain the corresponding 3#c-acyloxy - 20 - cyano - 5b - pregnan - 11 - on - 21 - oic acid lower alkyl ester, treating the latter with an alkali metal base to obtain 3#c-hydroxy-5b -pregnan - 11 - one - 20 - carboxy - 21 - oic acid, esterifying the latter with a lower aliphatic alcohol in the presence of a dehydrating agent to obtain 3#c-hydroxy-20-carboalkoxy-5b -pregnan - 11 - on - 21 - oic acid alkyl ester and treating the latter with an oxacyclic compound having a double bond in #c-position relative to the oxygen atom e.g. 2,3-dihydropyran, to obtain the desired compound. 3#c,21-Dihydroxy - 20,20 - bis - hydroxymethylene - 5b -pregnan - 11 - one is obtained by subjecting 3 - oxacyclo - 20 - carbalkoxy - 20 - benzyloxy-methylene - 5b - pregnan - 11 - on - 21 - oic acid alkyl ester to acid hydrolysis to obtain the corresponding 3#c-hydroxy-compound, treating this compound with a mixed metal hydride to obtain 3#c,11b ,21 - trihydroxy - 20 - hydroxy-methylene - 20 - benzyloxymethylene - 5b -pregnane, subjecting this compound to catalytic hydrogenolysis to form 3#c,11b ,21-tri-hydroxy - 20,20 - bis - hydroxy - methylene-5b -pregnane, acylating this compound to obtain 3#c,21 - diacyloxy - 11b - hydroxy - 20,20 - bis-acyloxymethylene - 5b - pregnane, oxidizing this compound to obtain 3#c,21-diacyloxy-20,20-bis - acyloxymethylene - 5b - pregnane - 11-one, which is saponified. Specifications 967,078, 988,805 and 988,806 are referred to. |
| priorityDate | 1961-01-24-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 31.