http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1004974-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_2dbb2d7ecbd600cf89fbdd230f4a466c |
| classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/Y02P20-55 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D207-34 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D207-34 |
| filingDate | 1964-03-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1965-09-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1004974-A |
| titleOfInvention | New amidines, process for their preparation and pharmaceutical compositions containing them |
| abstract | The invention comprises compounds of formula <FORM:1004974/C2/1> and their acid addition salts, wherein A is a straight or branched chain alkylene radical having 1 to 5 carbon atoms, R is an alkyl group having up to 4 carbon atoms and R1 is a carbamoyl, mono- or di-alkyl carbamoyl wherein the alkyl groups have up to 4 carbon atoms, alkoxy carbonyl, aralkoxycarbonyl or carboxylic acyl group, acyl groups specified being aliphatic acyl amidino-acyl, benzoyl, or pyridylcarbonyl groups, or a group of formula Z-X-CO, where X is a p-phenylene, chloro-p-phenylene, furylene or 1-methyl-pyrrelene radical and Z is a nitro, amino, formamido, acetamido, ureido, amidino, guanidino, amidinoacetamido, guanidinoacetamido, 3-guanidinopropionamido- or 4-guanidinobutyramido group, and their preparation by (a) reacting a compound of formula <FORM:1004974/C2/2> wherein R1 may, in addition to the above definition, contain a cyano-substituent, with hydrogen chloride in the presence of an alkanol having up to 6 carbon atoms to form a compound of formula <FORM:1004974/C2/3> wherein any cyano-group in R1 is similarly converted and R11 is an alkyl group having up to 6 carbon atoms, and reacting this product with ammonia, (b) acylating compounds wherein R1 is a hydrogen atom, (c) hydrogenating a nitro-product to an amino-product, (d) reacting an amino-product with potassium cyanate to give a ureido-product, with cyanamide to give a guanidino-product, or with a guanidino carboxylic acid to give a guanidinoacylamino-product, or (e) reacting an amino-product with an N-benzyloxycarbonyl amino-acid, to obtain the corresponding amide, removing the protecting group, and reacting the free amino group with S-methyl isothiouronium bromide to convert it to a guanidino-group. Compounds of formula <FORM:1004974/C2/4> are prepared by acylation or, if R1 is to be a carbamoyl group, by reacting the free amino-compound with potassium cyanate. Compounds of the first general formula wherein R1 is a hydrogen atom are prepared by treating a 4 - nitro - 2 - (g - cyano - alkylcarbamoyl) - pyrrole as in process (a) above, and hydrogenating the 4-nitro-product. 4 - Amino - 2 - (g - cyano - alkylcarbamoyl)-pyrrols are prepared by reacting a 4-nitro-pyrrole-2-carboxylic acid halide, formed by reacting the acid with thionyl chloride, with the appropriate cyanoamine and hydrogenating the nitro-product after, if desired, introducing a 1-butyl group by reaction with butyl iodide. 1 - Methyl - 4 - nitro -pyrrole - 2 - carboxylic acid is prepared by treating the corresponding 2-cyano-pyrrole with hydrogen chloride in ethanol to give an imino-ether as in process (a) above, hydrolysing this product to give the 2-carboxylic acid ethyl ester, and saponifying this product to give the free acid. 4-Benzyloxycarbonylamino-butyric acid is prepared by reaction of benzyl chloroformate and 4-amino-butyric acid. The compounds of the invention have anti-tubercular and virucidal activity, and may be used in the form of their non-toxic acid addition salts in combination with a pharmaceutical carrier in forms suitable for oral, parenteral or rectal administration, e.g. as capsules, compressed tablets, pills, powders, granules, solutions, suspensions, emulsions, syrups, elixirs and suppositories. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-5175182-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-5472976-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4766142-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-5017599-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-1556035-A2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-5310752-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-1556035-A4 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-5049579-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2004026264-A2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/JP-H0780843-B2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-9214707-A1 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/JP-S6277362-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4738980-A |
| priorityDate | 1963-04-04-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
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