http://rdf.ncbi.nlm.nih.gov/pubchem/patent/ES-368120-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_b0d43ca03213c433892c1e9948cb7b17 |
| classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/Y10S435-911 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/Y10S435-913 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61K31-573 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61K31-58 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J71-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J71-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-573 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-58 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A63H33-16 |
| filingDate | 1969-06-07-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1971-05-01-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | ES-368120-A1 |
| titleOfInvention | PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF 14 ALPHA, 17 ALPHA, 17 ALPHA-METHYLEDIOXIPREGNANE. |
| abstract | The invention comprises #4, #1'4, #4,6 and #1,4,6 steroids of formula wherein R 1 is C 1-8 aliphatic hydrocarbyl (optionally substituted by C 2-7 alkoxycarbonyl), C 1-10 aryl (optionally substituted by halo, C 1-6 alkyl and/or C 1-6 alkoxy), aryl-C 1-6 -alkyl, C 3-6 cycloalkyl, 2-furyl or 2-thienyl R 2 is H or halo R 3 is oxo, H(#-OH) or H(#-halo) and R 4 is H or acyl and their preparation from the corresponding 14[alpha],17[alpha]-diols by reaction with a compound of formula R 1 CHO or R 1 CH(OR 5 ) 2 , where R 5 is C 1-6 alkyl. In addition: compounds I wherein R 3 is H(#-OH) are obtainable by microbial hydroxylation of the corresponding 11-unsubstituted compounds compounds I wherein R 3 is OXO are obtainable by oxidation of the corresponding 11[alpha]-ols and compounds I, wherein R 2 is halo and R 3 is H(#-OH) or H(#-halo) are obtainable by reacting the corresponding #9(11)-9,11-unsubstituted compounds with HClO, HBrO, 5,5-dimethyl-1,3- dibromo - hydantoin (Example 22) or N- chlorosuccinimide/HCl. Compounds I are interconvertible by introduction of #1 or #6 unsaturation, oxidation of 11#-OH to 11-OXO, esterification of 21-OH and hydrolysis of 21-OAcyl. 11#,17[alpha],21 - Trihydroxy - 4,14 - pregnadiene- 3,20-dione 21-acetate is formed as a by-product in the preparation of compounds I by reacting 11#,14[alpha],17[alpha],21 - tetrahydroxy - 4 - pregnene- 3,20 - dione 21-acetate with nonanal/perchloric acid and crotonaldehyde/perchloric acid (Examples 6 and 9). 21 - Hydroxy - 14[alpha],17[alpha] - ethylidenedioxy- 1,4,9(11) - pregnatriene - 3,20 - dione 21-acetate is prepared by reacting thionyl chloride with 11#,21 - dihydroxy - 14[alpha],17[alpha] - ethylidenedioxy- 1,4 - pregnadiene - 3,20 - dione 21 - acetate. 11[alpha],21 - Dihydroxy - 14[alpha],17[alpha] - ethylidenedioxy - 4 - pregnene - 3,20 - dione 21-acetate is prepared from the corresponding free 21-ol, which is prepared by microbial hydroxylation of 21 - hydroxy - 14[alpha],17[alpha] - ethylidenedioxy-4- pregnene-3,20-dione, which is prepared from its 21-acetate, which in turn is prepared by reacting 14[alpha],17[alpha],21 - trihydroxy - 4 - pregnene - 3,20- dione 21-acetate with paraldehyde. 11[alpha],14[alpha],17[alpha],21 - Tetrahydroxy - 4 - pregnene- 3,20-dione is prepared by microbial hydroxylation of 14[alpha],17[alpha],21-trihydroxy-4-pregnene-3,20- dione which in turn is prepared by microbial hydroxylation of cortexolone. Compounds I are stated to possess antiinflammatory activity and may be made up with carriers into pharmaceutical compositions for oral, parenteral and topical administration. |
| priorityDate | 1968-06-07-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 41.