http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-101622268-B
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_f9a36328274867f46f8fc1fb9c868703 |
| classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/Y02P20-55 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J51-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P15-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J41-0094 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J21-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P15-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J21-006 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J41-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J41-0083 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J41-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J21-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J51-00 |
| filingDate | 2008-06-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| grantDate | 2012-09-05-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_975936e71b60268031e6211e137811c5 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_834e5695af7b7d64d606da72ff48494d http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_02f263583607dc20475e798923c6f67f http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_8c3203dfe6f55ed5e1c6eb1d00dc1dde http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_5e53068b29bd5fe86f71d2bfca13c63d http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_c79921dddd62733f89aad31e5a1e3a99 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_c14821be1032d9152e71286d23a6a126 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_5859b65604613287c61f4621378cb0ec http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_074fcd7b7b2e974b849c1ec41e0d6196 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_a9d55ce06d5c18a2b326c11221fa842c http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_b0d46025d66cdcf968b3d9cb7216142a http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_a4a2ff45a9928dc03493dea85ec62af7 |
| publicationDate | 2012-09-05-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | CN-101622268-B |
| titleOfInvention | Industrial method for the synthesis of 17-acetoxy-11beta-[4-(dimethylamino)-phenyl]-21-methoxy-19-norpregna-4,9-dien-3,20-dione and the key intermediates of the process |
| abstract | The present invention relates to a process for the synthesis of the known 17-acetoxy-11-ss-[4-(dimethylamino)-phenyl]-21-methoxy-19-norpregna-4,9-dien-3,20-dione (further on CDB-4124) of formula (I) from 3,3-[1,2-etandiyl-bis(oxy)]-oestr-5(10),9(l l)-dien-17-one of formula (II). Compound CDB-4124 belongs to the group of anti-hormones. The process according to the invention is the following: i) formation of an epoxide on the double bond in position 5(10) of 3,3-[l,2-ethandiyl- bis(oxy)]-oestr-5(10),9(l l)-dien-17-one of formula (II) with hydrogen peroxide; ii) addition of hydrogen cyanide formed in situ on position 17 of the obtained 5,10a- epoxy-3,3-[l,2-ethandiyl-bis(oxy)]-5a-oestr-9(l l)-en-17-one of formula (III); iii) silylation of the hydroxyl group in position 17 of the formed 5,10a-epoxy-3,3-[l,2- ethandiyl-bis(oxy)]-17a-hydroxy-5a-oestr-9(l l)-en-17ss-carbonitrile of formula (IV) with trimethyl chlorosilane; iv) reacting the obtained 5,10a-epoxy-3,3-[l,2-ethandiyl-bis(oxy)]-17-[trimethyl-silyl-oxy]-5a-oestr-9(l l)-en-17ss-carbonitrile of formula (V) with 4-(dimethylamino)-phenyl magnesium bromide Grignard reagent in the presence of CuCl (Teutsch reaction); v) silylation ofthe hydroxyl group in position 5 of the formed l lss-[4-(dimethyl-amino)-phenyl] -3,3 - [1,2-ethandiyl-bis(oxy)] -5 -hydroxy- 17a- [trimethylsilyl-(oxy)] -5 a-oestr-9-en-17ss-carbonitrile of formula (VI) with trimethyl chlorosilane; vi) reacting the obtained llss-[4-(dimethylamino)-phenyl]-3,3-[l,2-ethandiyl-bis(oxy)]-5,17a-bis-[trimethyl-silyl-(oxy)]-5a-oestr-9-en-17ss-carbonitrile of formula (VII) with diisobutyl aluminum hydride and after addition of acid to the reaction mixture; vii) methoxy-methylation of the obtained l lss-[4-(dimethylamino)-phenyl]-3,3-[1,2-ethandiyl-bis(oxy)]-5, 17a-bis-[trimethyl-silyl-(oxy)]-5a-oestr-9-en-17ss-carbaldehide of formula (VIII) with methoxy-methyl Grignard reagent formed in situ, while hydrolyzing the trimethylsilyl protective groups. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/CN-105358248-A |
| priorityDate | 2007-06-27-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 37.