GB577843A - Biguanide derivatives - Google Patents
Biguanide derivativesInfo
- Publication number
- GB577843A GB577843A GB888944A GB888944A GB577843A GB 577843 A GB577843 A GB 577843A GB 888944 A GB888944 A GB 888944A GB 888944 A GB888944 A GB 888944A GB 577843 A GB577843 A GB 577843A
- Authority
- GB
- United Kingdom
- Prior art keywords
- biguanide
- chlorophenyl
- preparation
- methyl
- aqueous
- 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
Substituted biguanides of the general formula A-NX-C(NH)-NH-C(NH)-NRR1, wherein A represents an aryl group, X represents hydrogen or an alkyl group, R represents a hydrocarbon radical and R1 represents hydrogen or a hydrocarbon radical or, alternatively, R and R1 may be joined together to form a divalent aliphatic hydrocarbon chain, and wherein the groups A, R and R1 may bear one or more non-acidic constituents, are obtained by the interaction of an aryl-dicyandiamide of the general formula A-NX-C(NH)-NH-CN with an amine of the general formula NHRR1. The aryl-dicyandiamide components may be prepared as described in Specification 576,401. Examples relate to (1) the preparation of Na -p-chlorophenyl - No - diethyl - biguanide by the interaction of p-chlorophenyl-dicyandiamide and diethylamine aqueous ethyl alcohol containing copper sulphate, separation of the copper complex, treatment of this with aqueous hydrochloric acid and sodium sulphide, separation of the copper as sulphide and treatment of the solution with caustic soda to precipitate the biguanide; (2) to (28), the preparation similarly of (2) Na -p-chlorophenyl-No -dimethyl-biguanide; (3) Na -p-chlorophenyl-No -methyl-No -isopropyl-biguanide, (4) Na -p-chlorophenyl-No -dibutyl-biguanide, (5) Na -p-chlorophenyl-No -ethyl-No -b -diethylaminoethyl-biguanide, (7) Na - p - chlorophenyl - No : No - tetramethylene - biguanide, (8) Na - phenyl - No - diethyl - biguanide, (9) Na - p - tolyl - No - dimethyl - biguanide, (10) Na - p - anisyl - No - dimethyl - biguanide, (11) Na - p - anisyl - No - diethyl - biguanide, (12) Na - p - nitrophenyl - No - di - methyl - biguanide, (13) Na -p-nitrophenyl-Na -diethyl-biguanide, (14) Na -3 : 4-dimethylphenyl-No -diethyl-biguanide, (15) Na -p-chlorophenyl-No -allyl-biguanide, (16) Na -p-chlorophenyl-No -ethyl-biguanide, (17) Na -p-chlorophenyl-No -n-amyl-biguanide, (18) Na -p-chlorophenyl-No - n - propyl - biguanide, (19) Na - p - chlorophenyl - No - isopropyl - biguanide, (20) Na - p - chlorophenyl - No - n - butyl - biguanide acetate, (21) Na -p-chlorophenyl-No -isobutyl-biguanide hydrochloride, (22) Na - p - chlorophenyl - No - tert.-butyl-biguanide hydrochloride, (23) Na -p-chlorophenyl - No - ethyl - No - b - diethylamino - ethyl - biguanide, (24) Na - p - chlorophenyl - No - methyl - No - n - propyl - biguanide, (25) Na - p - acetylaminophenyl - No - methyl - No - isopropyl - biguanide acetate, (26) Na -p-chlorophenyl-No -methyl-biguanide, (27) Na -p-chlorophenyl-No -(1 - methyl - 4 - diethylamino) - butyl - biguanide carbonate, (28) Na -p-chlorophenyl-Na -methyl-No -diethyl-biguanide, (29) the preparation of Na - p - chlorophenyl - No : No - pentamethylene biguanide by the interaction of p-chlorophenyl-dicyandiamide and piperidine in aqueous b -ethoxyethanol containing copper sulphate and isolation of the product as in (1); (3) to (33) the preparation similarly of (3) Na -p-chlorophenyl-No - cyclohexyl - biguanide, (31) Na - p - chlorophenyl - No - b - diethylaminoethyl - biguanide, (32) Na - p - chlorophenyl - No - b - diethylamino - propyl - biguanide, (33) Na - p - anisyl - No : No - pentamethylene-biguanide; (34) the preparation of Na : No -diphenyl-biguanide hydrochloride by the interaction of phenyldicyandiamide with aniline hydrochloride in aqueous dioxane; (35) to (40) the preparation similarly of (35) Na -p-chlorophenyl-No -phenyl-biguanide, (36) Na - p - chlorophenyl - No - b - naphthyl - biguanide, (37) Na - p - chlorophenyl - No - p - anisyl - biguanide, (38) Na : No - di - p - tolyl - biguanide, (39) Na : No -di-p-anisyl-biguanide hydrochloride, (40) Na - p - anisyl - No : No - pentamethylene - biguanide; (41) the preparation of Na -p-chlorophenyl-No : No -pentamethylene-biguanide by the interaction of p-chlorophenyldicyandianide and piperidine in aqueous ethyl alcohol containing bronze powder, dilution of the reaction mixture with aqueous hydrochloric acid, removal of the copper bronze, and isolation of the product as in (1); (42) the preparation of Na - p - chlorophenyl - No - iso - propyl-biguanide acetate by the interaction of p-chlorophenyl dicyandiamide and isopropylamine hydrochloride in aqueous ethyl alcohol, containing hydrated copper oxide, removal of the alcohol by distillation, isolation of the product as in (1) and conversion into the acetate; (43) the preparation of Na -p-chlorophenyl-N -isopropyl-biguanide acetate by the interaction of p-chlorophenyldicyandiamide and isopropylamine in aqueous ethyl alcohol containing zinc chloride removal of the alcohol by distillation, treatment of aqueous caustic soda to obtain the biguanide and conversion into the acetate; (44) the preparation of Na -p-chlorophenyl-No : No -pentamethylene-biguanide by heating under reflux p-chlorophenyldicyandiamide and piperidine. The salts of the biguanides with acetic, lactic, methanesulphonic, methylene - disalicylic, methylene - bis - 2 : 3 - hydroxynaphthoic and hydrochloric acids are referred to. Na -p-chlorophenyl-Na -methyl-dicyandiamide (example 28) is obtained by reaction of p-chlorophenyl-dicyandiamide with dimethyl sulphate in methyl alcohol containing caustic soda.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB888944A GB577843A (en) | 1944-05-10 | 1944-05-10 | Biguanide derivatives |
ES0172113A ES172113A1 (en) | 1944-05-10 | 1946-01-10 | A PROCEDURE FOR OBTAINING BIGUANIDA DERIVATIVES |
CY7148A CY71A (en) | 1944-05-10 | 1948-08-25 | Biguanide derivatives |
MY5400007A MY5400007A (en) | 1944-05-10 | 1954-12-31 | Biguanide derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB888944A GB577843A (en) | 1944-05-10 | 1944-05-10 | Biguanide derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB577843A true GB577843A (en) | 1946-06-03 |
Family
ID=9861250
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB888944A Expired GB577843A (en) | 1944-05-10 | 1944-05-10 | Biguanide derivatives |
Country Status (4)
Country | Link |
---|---|
CY (1) | CY71A (en) |
ES (1) | ES172113A1 (en) |
GB (1) | GB577843A (en) |
MY (1) | MY5400007A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2467371A (en) * | 1944-05-10 | 1949-04-19 | Ici Ltd | Biguanide derivatives |
US2475081A (en) * | 1945-10-08 | 1949-07-05 | Ici Ltd | Biguanide derivatives |
US2479498A (en) * | 1946-08-08 | 1949-08-16 | American Cyanamid Co | Preparation of 1,2-disubstituted-3-cyanoguanidines |
US2498252A (en) * | 1947-06-19 | 1950-02-21 | Ici Ltd | Biguanide compounds |
US2548654A (en) * | 1945-05-25 | 1951-04-10 | Ici Ltd | N-aryl n-dialkyl biguanides |
US5376686A (en) * | 1991-04-05 | 1994-12-27 | Otsuka Pharmaceutical Co., Ltd. | Biguanide derivatives, manufacturing method thereof, and disinfectants containing the derivatives |
US5387656A (en) * | 1990-07-23 | 1995-02-07 | Alliedsignal Inc. | Substituted cyanoguanidines as curing agents for epoxy resins |
US5534565A (en) * | 1992-12-21 | 1996-07-09 | Alliedsignal Inc. | Solvent free epoxy resin compositions containing substituted cyanoguanidines |
CN111018748A (en) * | 2019-12-27 | 2020-04-17 | 广东省生物医药技术研究所 | Compound (S) -1- (1-naphthyl) ethyl biguanide and preparation method and application thereof |
-
1944
- 1944-05-10 GB GB888944A patent/GB577843A/en not_active Expired
-
1946
- 1946-01-10 ES ES0172113A patent/ES172113A1/en not_active Expired
-
1948
- 1948-08-25 CY CY7148A patent/CY71A/en unknown
-
1954
- 1954-12-31 MY MY5400007A patent/MY5400007A/en unknown
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2467371A (en) * | 1944-05-10 | 1949-04-19 | Ici Ltd | Biguanide derivatives |
US2548654A (en) * | 1945-05-25 | 1951-04-10 | Ici Ltd | N-aryl n-dialkyl biguanides |
US2475081A (en) * | 1945-10-08 | 1949-07-05 | Ici Ltd | Biguanide derivatives |
US2479498A (en) * | 1946-08-08 | 1949-08-16 | American Cyanamid Co | Preparation of 1,2-disubstituted-3-cyanoguanidines |
US2498252A (en) * | 1947-06-19 | 1950-02-21 | Ici Ltd | Biguanide compounds |
US5387656A (en) * | 1990-07-23 | 1995-02-07 | Alliedsignal Inc. | Substituted cyanoguanidines as curing agents for epoxy resins |
US5376686A (en) * | 1991-04-05 | 1994-12-27 | Otsuka Pharmaceutical Co., Ltd. | Biguanide derivatives, manufacturing method thereof, and disinfectants containing the derivatives |
US5534565A (en) * | 1992-12-21 | 1996-07-09 | Alliedsignal Inc. | Solvent free epoxy resin compositions containing substituted cyanoguanidines |
CN111018748A (en) * | 2019-12-27 | 2020-04-17 | 广东省生物医药技术研究所 | Compound (S) -1- (1-naphthyl) ethyl biguanide and preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
CY71A (en) | 1948-08-25 |
ES172113A1 (en) | 1946-02-16 |
MY5400007A (en) | 1954-12-31 |
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