http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EA-200900015-A1
Outgoing Links
| Predicate | Object |
|---|---|
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J31-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J41-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J21-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P5-46 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J41-0083 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J31-006 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J21-006 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P5-24 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J71-001 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J71-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J31-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J21-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J41-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J71-00 |
| filingDate | 2007-05-18-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 2009-04-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | EA-200900015-A1 |
| titleOfInvention | THE INDUSTRIAL METHOD FOR SYNTHESIS OF 17α-ACETOXY-11β- [4- (N, N-DIMETHYLAMINO) PHENYL] -19-NORPREGNA-4,9-DIEN-3,20-DIONA AND NEW INTERMEDIATE CONNECTIONS RECEIVED UNITED SOURCE, UNITED SOURCE |
| abstract | The present invention relates to a new industrial method for the synthesis of unsolvated 17α-acetoxy-11β- [4- (N, N-dimethylamino) phenyl] -19-norpregna-4,9-diene-3,20-dione [CDB-2914] of the formula ( I), which is a strong antiprogestogen and antiglucocorticoid agent. The present invention also relates to compounds of formulas (VII) and (VIII) used as intermediates in the process. The method of the present invention is as follows: i) 3- (ethylenedioxy) estra-5 (10), 9 (11) -diene-17-one of formula (X) is reacted with potassium acetylide obtained in situ in dry tetrahydrofuran known by the method, ii) the obtained 3-ethylenedioxy) -17α-ethynyl-17β-hydroxy-estra-5 (10), 9 (11) -diene of the formula (IX) is reacted with phenylsulphenyl chloride in dichloromethane in the presence of triethylamine and acetic acid, iii ) the resulting mixture of isomers of 3- (ethylenedioxy) -21- (phenylsulfinyl) -19-norpregn-5 (10), 9 (11), 17 (20), 20-tetraene of formula (VIII) is first reacted with sodium methoxide in me anole, then with trimethylphosphite, iv) the obtained 3- (ethylenedioxy) -17α-hydroxy-20-methoxy-19-norpregn-5 (10), 9 (11), 20-triene of formula (VII) are reacted with hydrogen chloride in methanol, then v) the resulting 3- (ethylenedioxy) -17α-hydroxy-19-norpregn-5 (10), 9 (11) -diene-20-one of formula (VI) is reacted with ethylene glycol in dichloromethane in the presence of trimethyl orthoformate and p-toluenesulfonic acid by a known method, vi) the resulting 3,3,20,20-bis (ethylenedioxy) -17α-hydroxy-19-norpregn-5 (10), 9 (11) -diene of the formula (V) are reacted with hydrogen peroxide in a mixture of pyridine and dichloromethane in the presence of hexachloroacetone according to a known method, vii) the obtained 3,3,20,20-bis (ethylenedioxy) -17α-hydroxy-5,10-epoxy-19-norpregn-9 (11) -en of formula (IV) containing a mixture of 5α , 10α and 5β, β-epoxides of approximately 1: 1 are isolated from the solution and reacted with the Grignard reagent obtained |
| priorityDate | 2006-06-14-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 55.