http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1198941-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_d202e9e866984fe229f6facc38f1d740 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61K31-415 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/E21D11-28 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D405-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D403-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D401-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D413-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D409-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D417-04 |
| classificationIPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D263-30 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D277-20 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D409-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/E21D11-28 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-415 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D413-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D235-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D417-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D401-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D403-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D405-04 |
| filingDate | 1968-02-01-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_2e05652eeb94035432eb26b1968bd2b9 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_f2d5dfc13545ffc96b993b61a324dda2 |
| publicationDate | 1970-07-15-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1198941-A |
| titleOfInvention | Benzimidazole Derivatives |
| abstract | 1,198,941. Benzimidazole derivatives. MERCK & CO. Inc. 1 Feb., 1968 [3 Feb., 1967; 9 Jan., 1968], No. 5259/68. Heading C2C. Novel compounds (I) in which X is O or S; R 1 is a five-membered monocyclic heteroaromatic ring containing 1-3 O, S or N atoms; R 2 is H, OH, C 1-8 alkyl, C 1-8 alkoxy, aralkyl, acyl, acyloxy, carboxyalkoxy, carbamoyl, N-alkylcarbamoyl, or alkoxycarbonyl; R 3 is H, or C 1-8 alkyl and R 4 is H, aralkyl, haloaralkyl, cycloalkyl, C 1-8 alkylamino, di - (C 1-8 alkyl)amino, alkylenimino, hetero - interrupted alkylenimino, cycloalkylamino or a radical R-, RO- or RS- in which R is a C 1-8 univalent aliphatic hydrocarbon, C 1-8 univalent aliphatic halohydrocarbon, aryl, haloaryl, alkaryl, aminoaryl or heterocyclic radical and their acid addition salts and metal complexes when R 2 is H are prepared by: (a) reacting an appropriate 5- NH(R 3 )-substituted benzimidazole with R 4 - C(X)Y where Y is a halogen atom; (b) reacting an appropriate 5-RS-CO-N(R 3 )- substituted benzimidazole with a compound ROH to give a compound (I) in which X is O and R 4 is RO (R being radical R from ROH); (c) reacting an appropriate 5-isothiocyanato benzimidazole with a compound ROH or RSH to give a compound (I) in which X is S and R 4 is RO- or RS-; (d) reacting a compound (I) in which X is O with phosphorus pentasulphide to give a compound (I) in which X is S; (e) reacting an appropriate 5-NH(R 3 )- substituted benzimidazole with an alkyl isocyanate or isothiocyanate to give a compound (I) in which R 4 is alkylamino; (f) reacting an appropriate 5-NH(R 3 )- substituted benzimidazole with a dialkylcarbamoyl halide to give a compound (I) in which X is O and R 4 is dialkylamino; (g) reacting a compound (I) in which X is O and R 4 is alkylthio with a dialkylamine, alkylenimine or hetero-interrupted alkylenimine to give a compound (I) in which R 4 is dialkylamino, alkylenimino or hetero-interrupted alkylenimino; (h) reacting an appropriate 5- isothiocyanato-benzimidazole with a dialkylamine, alkylenimine or hetero-interrupted alkylenimine to give a compound (I) in which X is S and R 4 is dialkylamino, alkylenimino or hetero-interrupted alkylenimino; or (i) introducing the group R 2 into an appropriate benzimidazole by reacting an alkali metal salt of a compound (I) in which R 2 is H with an alkyl, aralkyl or acyl halide, or by reacting a compound (I) in which R 2 is H with an alkyl isocyanate to give a compound (I) where R 2 is carbamoyl, or by reacting a compound (I) in which R 2 is H with an alkyl haloformate to give a compound (I) in which R 2 is alkoxycarbonyl; followed in any of (a)-(i) by salt formation, where desired. Intermediates isolated are 5-nitro-2-(4<SP>1</SP>-thiazolyl)-benzimidazole, prepared by nitration of the 5 - unsubstituted compound; 5 - nitro - 2 - (2<SP>1</SP> - furyl) - benzimidazole, 5 - nitro - 2 - (2<SP>1</SP>- pyrryl) - benzimidazole and 5 - nitro - 2 - (2<SP>1</SP>- thienyl) - benzimidazole, prepared by reacting the appropriate furan-, pyrrole- or thiophene- 2 - aldehyde with o - amino - p - nitro - aniline; 5 - amino - 2 - (4<SP>1 </SP>- thiazolyl) - benzimidazole, prepared by reduction of the 5-nitro compound; 5 - isothiocyanato - 2 - (4<SP>1 </SP>- thiazolyl) - benzimidazole, prepared from the 5-phenoxythiocarbonylamino compound by heating in pyridino; 5 - nitro - 1 - methoxy - 2 - (4<SP>1 </SP>- thiazolyl)- benzimidazole, prepared by nitration of the 5- unsubstituted compound and 5-amino-1-methoxy - 2 - (4<SP>1</SP>- thiazolyl) - benzimidazole hydrochloride, prepared by reduction of the previous intermediate. Pharmaceutical compositions comprise a novel compound (I) in conjunction with a suitable carrier or diluent and are suitable for oral or parenteral administration as anthelmintics or antifungal agents. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-1581217-A1 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3983130-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AU-2003286757-B2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3985755-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-B486280-I5 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-7622592-B2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-1581217-A4 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2005042513-A1 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/JP-2006513159-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3853894-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-7230020-B2 |
| priorityDate | 1967-02-03-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
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