GB619498A - Manufacture of biguanide derivatives - Google Patents
Manufacture of biguanide derivativesInfo
- Publication number
- GB619498A GB619498A GB26159/45A GB2615945A GB619498A GB 619498 A GB619498 A GB 619498A GB 26159/45 A GB26159/45 A GB 26159/45A GB 2615945 A GB2615945 A GB 2615945A GB 619498 A GB619498 A GB 619498A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrochloride
- methyl
- chlorophenyl
- replaced
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB26159/45A GB619498A (en) | 1945-12-08 | 1945-12-08 | Manufacture of biguanide derivatives |
ES176029A ES176029A2 (en) | 1945-12-08 | 1946-12-07 | PROCEDURE FOR OBTAINING BIGUANIDAS DERIVATIVES |
CY7949A CY79A (en) | 1945-12-08 | 1949-09-07 | Manufacture of biguanide derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB26159/45A GB619498A (en) | 1945-12-08 | 1945-12-08 | Manufacture of biguanide derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB619498A true GB619498A (en) | 1949-03-10 |
Family
ID=10239295
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB26159/45A Expired GB619498A (en) | 1945-12-08 | 1945-12-08 | Manufacture of biguanide derivatives |
Country Status (3)
Country | Link |
---|---|
CY (1) | CY79A (en) |
ES (1) | ES176029A2 (en) |
GB (1) | GB619498A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115745846A (en) * | 2022-12-09 | 2023-03-07 | 石家庄市普力制药有限公司 | Preparation method of metformin hydrochloride |
-
1945
- 1945-12-08 GB GB26159/45A patent/GB619498A/en not_active Expired
-
1946
- 1946-12-07 ES ES176029A patent/ES176029A2/en not_active Expired
-
1949
- 1949-09-07 CY CY7949A patent/CY79A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115745846A (en) * | 2022-12-09 | 2023-03-07 | 石家庄市普力制药有限公司 | Preparation method of metformin hydrochloride |
CN115745846B (en) * | 2022-12-09 | 2024-03-19 | 石家庄市普力制药有限公司 | Preparation method of metformin hydrochloride |
Also Published As
Publication number | Publication date |
---|---|
ES176029A2 (en) | 1947-01-16 |
CY79A (en) | 1949-09-07 |
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