GB577843A - Biguanide derivatives - Google Patents

Biguanide derivatives

Info

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
Application number
GB888944A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB888944A priority Critical patent/GB577843A/en
Priority to ES0172113A priority patent/ES172113A1/en
Publication of GB577843A publication Critical patent/GB577843A/en
Priority to CY7148A priority patent/CY71A/en
Priority to MY5400007A priority patent/MY5400007A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20Derivatives 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
    • C07C279/24Y being a hetero atom
    • C07C279/26X 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.
GB888944A 1944-05-10 1944-05-10 Biguanide derivatives Expired GB577843A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (9)

* Cited by examiner, † Cited by third party
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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