http://rdf.ncbi.nlm.nih.gov/pubchem/patent/HU-230730-B1
Outgoing Links
Predicate | Object |
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assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_f9a36328274867f46f8fc1fb9c868703 |
classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C2603-16 |
classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J7-002 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C51-31 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J73-005 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-005 |
classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-473 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J73-00 |
filingDate | 2011-06-30-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_52590446501fe40d20017637b0090ca5 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_b121b696968330f08011829fed459982 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_66addb9d25f09a9ef33da22fcc3b62c4 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_00dd4431453eb30cda7eeea8f0f8dc27 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_b60a10828e3fd1d4c2d09cb64762cde1 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_3e65f9b818a1311445fa2e19c564b0c2 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_834229d7d37553711cc33ac03856b640 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_9b2fe9a0a9674bb30ca2ab9237daff64 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_0304a4371cd5ca39176575ad27fb368e http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_00dbf149d2224eeaab289e914dde5013 |
publicationDate | 2017-12-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
publicationNumber | HU-230730-B1 |
titleOfInvention | Process for preparing (5alpha,17beta)-N-[2,5-bis-(trifluoromethyl)phenyl]-3-oxo-4-aza-5-androst-1-ene-17-carboxylic acid amide |
abstract | The synthesis consists of reaction steps as follows: oxidizing the a,ß-unsaturated ketone system of ring "A" of pregn-4-ene-3,20-dion- of formula (II) with sodium metaperiodate in tert-butanol in the presence of potassium permanganate and alkali metal carbonate, reacting the obtained 3,5-seco acid with an ester of chloroformic acid in the presence of tertier organic base below 0°C, reacting the obtained new compound after isolation or without isolation with ammonia or ammonium acetate, cyclization of the resulting carboxamides with an acid, cathalytic hydrogenating the obtained ene lactame, and oxidizing the side chain at position 17 of the obtained pregnane compound with an alkali metal hypobromide in aqueous dioxane below 10°C. Thereafter on one hand the obtained (5a,17ß)-3-oxo-4-aza-5-androstane-17-carboxylic acid is reacted with chloroformic acid ester, the obtained new compound is reacted with 2,5-bis(trifluoromethyl)-aniline in the presence of a Lewis acid, the obtained amide is reacted with trimethyl chlorosilane in inert atmosphere in the presence of ?,?,?',?'-tetramethyl-ethylendiamine, then en excess iodine is added to the reaction mixture and the product of the iodination reaction is crystallized from acetonitrile, then the obtained 2-iodo-3-oxo-4-aza-17ß-carboxamide is reacted with potassium tert-butylate to furnish final product. On the other hand, (5a,17ß)-3-oxo-4-aza-5-androstane-17-carboxylic acid is transformed into methylester by known method, this latter is transformed into methyl (2a,5a,17ß)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate according to known method, the obtained compound is reacted with potassium-tert-butylate, the obtained (5a,17ß)-3-oxo-4-aza-5-androst-1-ene-17-carboxylic acid is reacted with an ester of chloroformic acid, then the obtained new compound is coupled with 2,5-bis(trifluoromethyl)-aniline in the presence of a Lewis acid catalyst to gain final product. |
priorityDate | 2011-06-30-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 236.