http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-619498-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_54453a3de4d42e42b9e7e8e6471366e6 http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_4b2d259c31f60b58a0d054d69d8ac69a http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_c26a74ec6951ca4f2e89a72989f0149b http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_73ee0bacab5a7576a6a3244747f6ea99 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C279-26 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C279-26 |
| filingDate | 1945-12-08-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1949-03-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-619498-A |
| titleOfInvention | Manufacture of biguanide derivatives |
| abstract | Biguanide derivatives, useful as chemotherapeutic agents or intermediates therefor, and of the general formula p <FORM:0619498/IV(b)/1> wherein A represents a halogenophenyl radical, R represents a hydrocarbon radical and R1 hydrogen or a hydrocarbon radical or R and R1 form, with the nitrogen atom, the radical of a heterocyclic amine, and R11 represents an alkyl radical, and wherein R and R1 may bear neutral or basic substituents, are manufactured by the interaction of an amine RR1NH with an aryldicyandiamide A-NH-C(:NR11)-NH-CN, e.g. by heating the substituted dicyandiamide with a salt of the amine, preferably in the presence of a solvent. In examples: (1) o - ethyl - o 1 - p - chlorophenyldicyandiamide is heated with isopropylamine hydrochloride in nitrobenzene to produce N1-p-chlorophenyl - N2 - ethyl - N5 - isopropylbiguanide monohydrochloride; (2) o -methyl-o 1-p-chlorophenyldicyandiamide is fused with methylamine hydrochloride and the product is treated with caustic soda solution to liberate N1-p-chlorphenyl - N2 : N5 - dimethylbiguanide; (3) the starting material of (2) is heated with ethylamine hydrochloride in nitrobenzene to give N1-p-chlorophenyl - N2 - methyl - N5 - ethylbiguanide monohydrochloride; (4) the ethylamine hydrochloride in (3) is replaced by methylamine hydrochloride, yielding the hydrochloride of the product of (2); (5) the isopropylamine hydrochloride in (1) is replaced by methylamine hydrochloride, producing N1-p-chlorophenyl-N2-ethyl-N5-methylbiguanide hydrochloride; (6) ethylamine hydrochloride similarly yields N1-p-chlorophenyl-N2 : N5-diethylbiguanide; (7) the ethylamine hydrochloride in (3) is replaced by piperidine hydrochloride, yielding N1-p-chlorophenyl - N2 - methyl - N5 : N5 - pentamethylene biguanide hydrochloride; (8) o -methyl-o 1-p-chlorophenyldicyandiamide is heated with p-chloroaniline hydrochloride in aqueous dioxane to form N1 : N5-di-p-chlorophenyl-N2-methylbiguanide hydrochloride, from which the base may be liberated with sodium hydroxide; (9) the corresponding N2-ethyl compounds are similarly prepared; (10) o -methyl-o 1-p-iodophenyldicyandiamide is treated as in (1) to give N1 - p - iodophenyl - N2 - methyl - N5 - isopropyl - biguanide hydrochloride; (11) the corresponding N2-ethyl compound is similarly prepared; (12) o -methyl-o 1-p-bromophenyldicyandiamide similarly yields N1-p-bromophenyl-N2-methyl-N5-isopropylbiguanide hydrochloride; (13) the isopropylamine hydrochloride in (1) is replaced by benzylamine hydrochloride, producing N1-p-chlorophenyl - N2 - ethyl - N5 - benzylbiguanide hydrochloride; (14) the ethylamine hydrochloride in (3) is replaced by n-propylamine hydrochloride, yielding N1-p-chlorophenyl-N2-methyl - N5 - n - propylbiguanide hydrochloride; (15) the corresponding N2-ethyl compound is similarly prepared; (16) and (17) the n-propylamine in (14) and (15) is replaced by n-butylamine, producing the corresponding N5-n-butyl compounds; (18) the ethylamine hydrochloride in (3) is replaced by methylisopropylamine hydrochloride, yielding N1-p-chlorophenyl-N2-methyl - N5 - methyl - N5 - isopropylbiguanide (isolated in the form of its acetate); (19) the corresponding N2-ethyl compound is similarly prepared; (20) and (21) diethylamine hydrochloride similarly yields the corresponding N5 : N5-diethyl compounds; (22) and (23) dimethylamine hydrochloride similarly yields the corresponding N5 : N5-dimethyl compounds; (24) the diethylamine hydrochloride in (21) is replaced by piperidine hydrochloride, producing N1 - p - chlorophenyl - N2 - ethyl - N5 : N5 - penta - methylenebiguanide; (25) the ethylamine hydrochloride in (18) is replaced by methylaniline hydrochloride, yielding N1-p-chlorophenyl - N2 - methyl - N5 - phenyl - N5 - methyl - biguanide acetate. Specifications 577,843 and 619,497 are referred to. |
| priorityDate | 1945-12-08-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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