http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-819016-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_60c87d786b8f797a438789e91ce9d0c1 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J31-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J31-00 |
| filingDate | 1956-04-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_3244f048f59fe9cd9367f59a6688d17f |
| publicationDate | 1959-08-26-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-819016-A |
| titleOfInvention | Derivatives of steroids |
| abstract | The invention comprises 21-xanthogenates and 21-xanthogenic acids of D 4-pregnenes and D 1,4-pregnadienes having keto groups in positions 3 and 20, a hydroxy group in position 17a , and a keto or hydroxy group in position 11, and their 6a -methyl analogues, and a process for their preparation by reacting the corresponding 21-hydroxy steroid, dissolved in an organic solvent at least partially miscible with water, with an alkali metal hydroxide, treating the resulting alcoholate with carbon disulphide, isolating the 21-xanthogenic acid by precipitation with a strong acid and if desired converting it to a 21-xanthogenate by reaction with an appropriate base. Suitable solvents do not react with alkali and carbon disulphide and preferably dissolve at least 5 per cent of water, e.g. dioxane, acetone, methyl ethyl ketone and dimethylformamide, and specified xanthogengenates are those of alkali metals, calcium, zinc, ethanol amine, diethylamine, N-ethyl piperidine, diisopropylamine, diethylaminopropylamine, n-butylamine and triethanolamine. A table gives the solubility of hydrocortisone 21-xanthogenic acid in aqueous solutions of ethylamine, triethylamine, b -diethylamino- and b - dimethylamino - ethanol, t - butylamine, 1-amino - 2 - propanol, 1 - diethylamino - 2 - propanol, ammonia and NaOH, with the formation of the corresponding salts. In examples: (1) cortisone in dioxane is treated with aqueous KOH, then CS2 in dioxane, benzene added, the mixture acidified and the 21-xanthogenic acid derivative of cortisone isolated from the benzene phase; (2) to (5), similarly are prepared the 21-xanthogenic acids of hydrocortisone, 1-dehydrocortisone, prednisolone and D 4-pregnene - 3,20 - dione - 11a ,17a ,21 - triol; (6) as in (1) using methyl isobutyl ketone as solvent; (7) 6a -methyl-cortisone in dimethylformamide is stirred with aqueous KOH and CS2, the aqueous layer removed and the potassium salt of 6a -methylcortisone 21-xanthogenic acid precipitated with ether; (8) to (12), the potassium xanthogenates of cortisone, hydrocortisone and prednisolone are prepared; (13) to (18) hydrocortisone 21-xanthogenic acid is treated with ethanolamine, diethylamine, tetraethyl ammonium hydroxide (from Ag2O and the corresponding iodide), N - ethylpiperidine, calcium hydroxide, and zinc hydroxide in aqueous alcohol giving the corresponding salts.ALSO:The invention comprises 21-xanthogenic acids of 3,20-diketo-17a -hydroxy- D 4-pregnenes and D 1,4-pregnadienes containing an 11-hydroxy or keto substituent and optionally a 6a -methyl group, which are rendered water-soluble by salt formation with inorganic or organic bases and are then suitable for intravenous injection for treatment of shock or for dermatological ointments. Specified xanthogenates are those of the alkali metals, calcium, zinc, ethanolamine, diethylamine, N-ethyl piperidine, di-isopropylamine, diethylaminopropylamine, n-butylamine and triethanolamine. |
| priorityDate | 1956-04-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 90.