http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-826364-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_d202e9e866984fe229f6facc38f1d740 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J5-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J5-00 |
| filingDate | 1956-01-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1960-01-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-826364-A |
| titleOfInvention | Cyclopentanopolyhydrophenanthrene compounds |
| abstract | The invention comprises compounds of the general formula <FORM:0826364/IV (b)/1> in which R is a hydrogen atom or an acyl radical other than -COCH2C(CH3)3 and -PO(OH)2, Y is halo, and Z is keto or b -hydroxy, together with a process for their preparation (including that of compounds wherein R is -COCH2C (CH3)3) by reacting a 2,4-dibromo-9a -halo-3,20 - diketo - 11 - oxygenated - 17a - hydroxy-21-acyloxy-allopregnane with a dehydrohalogenating agent, which may be a tertiary amine, e.g. collidine, or a nitrogenous ketone reagent, in which case the 3-keto group which couples with the reagent is subsequently liberated by reaction with a compound containing a free carbonyl group in the presence of an organic acid. The 21-acyl group may be finally removed by hydrolysis. Specified products of the invention are the 9a -chloro- and 9a -fluoro- D 1,4-3,20-diketo - (11b - hydroxy - or 11 - keto -) - 17a ,21-dihydroxy pregnadienes and the corresponding 21-acetates and propionates. In examples: (1) 9a - fluoro - 3,11,20 - triketo - 17a - hydroxy-21 - acetoxy - allopregnane is brominated in chloroform, and the resulting 2,4-dibromo derivative treated with 2,4-dinitrophenylhydrazine giving D 1,4 - 3,11,20 - triketo - 9a - fluoro-17a - hydroxy - 21 - acetoxypregnadiene-(2,4 - dinitrophenylhydrazone) which with pyruvic acid in aqueous acetic acid gives the free trione; (2) as in (1), using the corresponding 11b -hydroxy compound to give D 1,4-9a -fluoro-3,20 - diketo - 11b ,17a - dihydroxy - 21 - acetoxy-pregnadiene; (3) and (4), 9a - fluoro - 3,20-diketo - 11b ,17a - dihydroxy - 21 - acetoxy-allopregnane is brominated in acetic acid containing HBr, and the 2,4-dibromo compound dehydrobrominated with collidine in dimethyl-formamide to the product of (2), which (5), is saponified to 9a -fluorohydroretrocortin; (6), 9a - fluoro - 3,11,20 - triketo - 17a - hydroxy-21-acetoxy-allopregnane treated as in (4) to (6) yields 9a -fluoro-retrocortin. Specifications 826,362, 826,365 and 826,369 are referred to. |
| priorityDate | 1955-01-14-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 26.