http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-749198-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_c902faf6ae746c51fc8010672fc22894 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J13-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J13-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 |
| filingDate | 1953-08-26-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1956-05-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-749198-A |
| titleOfInvention | Carbonyloxysteroids |
| abstract | The invention comprises compounds of the formula <FORM:0749198/IV(a)/1> (wherein R is hydrogen, an alkali metal or a hydrocarbon radical containing up to eight carbon atoms inclusive, and R1 is an a - or b -hydroxyl group or ketonic oxygen), and a process for the preparation of a steroid D 17(20)-unsaturated-21-oic acid of the formula St = CH.CO2H or a salt or an ester thereof (wherein St is a cyclopentanophenanthrene nucleus attached to the side-chain at C17) by contacting a steroid of the formula St1.CO.CX2.CO.R (wherein X is chlorine, bromine or iodine, St1 is a cyclopentanophenanthrene nucleus attached to the side chain at C17 and having a 17-hydrogen atom, and R is hydrogen or -COO hydrocarbon) with a base, in the presence of hydroxyl or alkoxide ions. The intermediate dihalo compounds are prepared from compounds of the formula St1.CO.CH:C(OM)R wherein M is hydrogen or an alkali metal, by treatment with chlorine, bromine or iodine, and the two-stage process may be effected without isolation of the intermediate dihalo derivatives. Specified bases for the process are alkali metal alkoxides, hydroxides and carbonates, potassium propionate, basic ion-exchange resins and quaternary ammonium hydroxides, and an additional source of hydroxyl or alkoxyl ions, e.g. water, and the lower alkanols is normally employed. In examples (1) 11-keto-21:21-dibromo-21-ethoxy-oxalylprogesterone is treated with methanolic sodium methoxide, the mixture diluted with water and 3:11-diketo-4:17(20)-pregnadien-21-oic acid methyl ester isolated by methylene chloride extraction and chromatography. Other esters are similarly prepared using the appropriate sodium alkoxide. (2) As in (1) using aqueous potassium hydroxide as the base yields the corresponding acid as its potassium salt. (3) 3:11 - diketo - 4:17(20) - pregnadien - 21-oic acid is similarly obtained from an 11-keto-21:21 - dihalo - 21 - ethoxyoxalyl - or 21-formylprogesterone. (4) The sodium enolate of 11 - keto - 21 - ethoxyoxalylprogesterone is brominated in the presence of potassium acetate, and then treated with methanolic sodium methoxide to yield the methyl ester of 3:11-diketo - 4:17(20) - pregnadien - 21 - oic acid. Other examples describe the preparation of 3a -hydroxy - 11 - keto - 17(20) - pregnen - 21 - oic acid and its methyl ester; 3-keto-4:17(20)-pregnadien-21-oic acid methyl ester; 3a :11a -dihydroxy - 17(20) - pregnen - 21 - oic acid methyl ester; 3 - keto - 11a - hydroxy - 4:17(20)-pregnadien - 21 - oic acid and its methyl ester; 3 - keto - 11b - hydroxy - 4:17(20)-pregnadien - 21 - oic acid ethyl ester; 3b - hydroxy - 11 - keto - 17(20) - pregnen - 21 - oic acid ethyl ester; 3a - acetoxy - 11b - hydroxy-17(20) - pregnen - 21 - oic acid; 3b - acetoxy-11 - keto - 17(20) - allopregnen - 21 - oic acid methyl ester and 3-keto-9(11)-oxido-17(20)-pregnen-21-oic acid propyl ester. Specifications 724,163, 733,448, 749,196 and 749,199 are referred to. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3994933-A |
| priorityDate | 1952-08-30-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 51.