GB1095902A - Guanidine derivatives - Google Patents

Guanidine derivatives

Info

Publication number
GB1095902A
GB1095902A GB15025/65A GB1502565A GB1095902A GB 1095902 A GB1095902 A GB 1095902A GB 15025/65 A GB15025/65 A GB 15025/65A GB 1502565 A GB1502565 A GB 1502565A GB 1095902 A GB1095902 A GB 1095902A
Authority
GB
United Kingdom
Prior art keywords
bis
carbon atoms
group
hexamethylene
alkyl
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
GB15025/65A
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.)
STWB Inc
Original Assignee
Sterling Drug Inc
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 Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of GB1095902A publication Critical patent/GB1095902A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/43—Guanidines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • 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
    • C07C279/265—X and Y being nitrogen atoms, i.e. biguanides containing two or more biguanide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/42—Y being a hetero atom

Abstract

The invention comprises compounds of the formula <FORM:1095902/C2/1> in which R denotes an alkyl radical of 6-16 carbon atoms or a radical alkyl-Y-alkylene, in which Y is oxygen or sulphur and the alkyl and alkylene groups together contain 3-15 carbon atoms, R1 denotes hydrogen or an alkyl radical of 1-6 carbon atoms, x is 1 or 2 and A denotes any of the following bridging groups: (1) an alkylene group of 2-12 carbon atoms; (2) a group -(CH2)m-Y-(CH2)n-, in which m and n denote integers from 2 to 6; (3) a group <FORM:1095902/C2/2> (4) a group <FORM:1095902/C2/3> in which Z and Z1 are each alkylene of 1-3 carbon atoms; (5) a group <FORM:1095902/C2/4> in which Q denotes -O-, -S-, -SO- or -SO2-; (6) a diphenyl residue; or (7) a stilbene residue. A number of groups which A and R may denote are specified. The compounds in which x is 2 (bisbiguanides) may be prepared (1) by reacting a bridged bis-(3-cyanoguanidine) of the formula NC-NH-C(:NH)-NH-A-NH-C(:NH)-NH-CN (or an amidino-O-alkylurea equivalent thereof) with an amine R(R1)NH in salt form; or (2) by reacting a diamine H2N-A-NH2, optionally in salt form, with a 1-alkyl-3-cyanoguanidine of the formula R-N(R1)-C(:NH)-NH-CN. The compounds in which x is 1 (bisguanidines) may be prepared by reacting an appropriate N-alkyl-S-alkylisothiuronium halide with an appropriate bridged diamine. The products form mono- and di-acid salts with inorganic or organic acids, including mono- or di-carboxylic, sulphonic, sulphinic, phosphonic and phosphinic acids, organic acids of arsenic or antimony, acidic phenolic compounds and Lewis acids. A number of suitable acids are specified. The products also form co-ordination complexes with various heavy-metal ions, e.g. those of vanadium, chromium, manganese, cobalt, nickel, copper, zinc, palladium, rhenium and osmium. In typical examples: (1) 1,1-hexamethylene-bis - (3 - cyanoguanidine) and n - hexylamine hydrochloride yield 1,11-hexamethylene-bis [5-hexylbiguanide], (2) p-phenylene diamine and 1 - n - octyl - 3 - cyanoguanidine yield 1,11-(p-phenylene) - bis - [5 - (n - octyl) biguanide; (3) N - hexyl - S - ethylisothiuronium iodide and hexamethylene diamine yield 1,11-hexamethylene - bis - (3 - hexylguanidine). Other specified products include a cobalt complex of 1,11-hexamethylene - bis - [5 - (2 - ethylhexyl) biguanide], 1,11 - hexamethylene - bis - [5-(2-ethoxyethyl) biguanide], 1,11-hexamethylene-bis - [5 - (3 - isopropylmercaptopropyl) biguanide], 1,11 - thiobis - (p - phenylene) bis - (5-octylbiguanide), 1,11 - sulphinyl bis - (p-phenylene) bis - (5 - octylbiguanide), 1,11-sulphonyl bis - (p - phenylene) bis - (5 - octylbiguanide), 1,11 - (4,41 - stilbene) bis - (5 - octylbiguanide), 1,11 - [1,4 - cyclohexane bis-(methylene)] bis - (3 - hexylguanidine), 1,11-(p,p1 - biphenylene) bis - (3 - hexylguanidine), 1,11 - (2,3,5,6 - tetrachloro - p - xylylene) bis-[5 - (2 - ethylhexyl) biguanide], and 1,11-hexamethylene - [3 - (5 - methylmercaptopentyl)-guanidine]. The products show antibacterial and fungicidal activity (see Division A5).ALSO:As disinfectants, fungicides and skin and hair conditioners, use is made of bisbiguanides and bisguanidines of the formula <FORM:1095902/A5-A6/1> in which x is 1 or 2, R denotes an alkyl radical of 6-16 carbon atoms or a radical alkyl-Y-alkylene, in which Y is oxygen or sulphur and the alkyl and alkylene groups together contain 3-15 carbon atoms, R1 denotes hydrogen or an alkyl radical of 1-6 carbon atoms, and A denotes any of the following bridging groups:-(1) an alkylene group of 2-12 carbon atoms, (2) a group -(CH2)m-Y-(CH2)n-, in which m and n denote integers from 2 to 6, (3) a group <FORM:1095902/A5-A6/2> (4) a group <FORM:1095902/A5-A6/3> in which Z and Z1 are each alkylene of 1-3 carbon atoms, (5) a group <FORM:1095902/A5-A6/4> in which Q denotes -O-, -S-, -SO- or -SO2, (6) a diphenyl residue or (7) a stilbene residue (see Division C2). The compounds may be used as such or as their mono- or di-addition salts with acids. Comparative experimental results are given of the use of some of the compounds as bactericides, bacteriostats, fungicides and fungistats, and example 4 describes the treatment of cotton cloth with one of the compounds to impart an anti-bacterial finish thereto. It is stated also that some of the products are active against influenza virus and that other products have antihelmintic activity.
GB15025/65A 1964-04-09 1965-04-08 Guanidine derivatives Expired GB1095902A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US35861464A 1964-04-09 1964-04-09

Publications (1)

Publication Number Publication Date
GB1095902A true GB1095902A (en) 1967-12-20

Family

ID=23410360

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15025/65A Expired GB1095902A (en) 1964-04-09 1965-04-08 Guanidine derivatives

Country Status (7)

Country Link
BR (1) BR6568736D0 (en)
CH (1) CH486429A (en)
DE (1) DE1493210B2 (en)
DO (1) DOP1965001173A (en)
ES (1) ES311586A1 (en)
FR (1) FR1463818A (en)
GB (1) GB1095902A (en)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0125092A1 (en) * 1983-05-09 1984-11-14 Imperial Chemical Industries Plc Bisbiguanide compounds
EP0125827A1 (en) * 1983-05-09 1984-11-21 Imperial Chemical Industries Plc Polyether bisbiguanides
EP0126558A1 (en) * 1983-05-09 1984-11-28 Imperial Chemical Industries Plc Bisbiguanide derivatives
US4567174A (en) * 1984-05-07 1986-01-28 Imperial Chemical Industries Plc Bis(1-substituted biguanide) derivatives
US4574123A (en) * 1983-05-09 1986-03-04 Imperial Chemical Industries Plc 4,4'-Alkylenedipiperidine derivatives
US4590070A (en) * 1983-10-14 1986-05-20 Imperial Chemical Industries Plc Contraceptive methods
US4602042A (en) * 1983-10-14 1986-07-22 Imperial Chemical Industries Plc Contraceptive methods
FR2631038A1 (en) * 1988-05-03 1989-11-10 Ici Plc PROCESS FOR IMPROVING THE ADHESIVE OF AN ADHESIVE ON THE SURFACE OF A HARD TISSUE
EP0507317A2 (en) * 1991-04-05 1992-10-07 Otsuka Pharmaceutical Co., Ltd. Biguanide derivatives, manufacturing method thereof, and disinfectants containing the derivatives
WO1998020913A1 (en) * 1996-11-13 1998-05-22 Bausch & Lomb Incorporated Method for providing rapid disinfection of contact lenses
US5965088A (en) * 1997-10-23 1999-10-12 Lever; Andrea M. Method for providing rapid disinfection of contact lenses
AT411060B (en) * 2000-10-23 2003-09-25 P O C Oil Industry Technology New polymeric guanidine derivatives, used as disinfectant in (veterinary) medicine, waste liquor purification or domestic or trade application, are polycondensates of diamine with oxyalkylene chain and guanidine acid addition salt
FR2841778A1 (en) * 2002-07-05 2004-01-09 Oreal Composition for dyeing keratinic fibers, e.g. human hair, comprises a polyguanidine derivative
WO2008013555A1 (en) * 2006-07-26 2008-01-31 Watervisions International, Inc. Broad spectrum antimicrobial purification materials and methods for purifying fluids
WO2014113835A1 (en) * 2013-01-25 2014-07-31 Sealife Pharma Gmbh New bioactive polymers
WO2014174237A1 (en) 2013-04-26 2014-10-30 Biointeractions Limited Bioactive coatings
AT516070A1 (en) * 2014-07-31 2016-02-15 Sealife Pharma Gmbh Process for the preparation of polyguanidines
WO2016055644A1 (en) * 2014-10-10 2016-04-14 Lead Discovery Siena S.R.L. Linear guanidine derivatives, methods of preparation and uses thereof
EP3524055A1 (en) 2018-02-08 2019-08-14 BCSK Biocid GmbH Antibacterial and spermicidal lubricant
USRE49522E1 (en) 2013-04-26 2023-05-09 Biointeractions Ltd. Bioactive coatings

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3562385A (en) * 1968-12-23 1971-02-09 Merck & Co Inc Dental antiplaque and anticalculus compositions
IL39245A (en) * 1971-04-21 1974-12-31 Murphy Chemical Ltd Diguanidino alkanes and fungicidal compositions containing them
BE793229A (en) * 1971-12-23 1973-06-22 Merck & Co Inc GUANIDINE DERIVATIVES WITH ANTI-ACNE ACTION
NO135634C (en) * 1972-03-16 1977-05-04 Farmaceutisk Ind As
IE37842B1 (en) * 1972-06-30 1977-10-26 Procter & Gamble Oral compositions for plaque caries and calculus retardation with reduced staining tendencies
GB1365030A (en) * 1972-11-30 1974-08-29 Merck & Co Inc Oral compositions
DE2651467A1 (en) * 1976-11-11 1978-05-18 Bayer Ag SUBSTITUTED O-PHENYLENE DIAMINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0125092A1 (en) * 1983-05-09 1984-11-14 Imperial Chemical Industries Plc Bisbiguanide compounds
EP0125827A1 (en) * 1983-05-09 1984-11-21 Imperial Chemical Industries Plc Polyether bisbiguanides
EP0126558A1 (en) * 1983-05-09 1984-11-28 Imperial Chemical Industries Plc Bisbiguanide derivatives
US4574123A (en) * 1983-05-09 1986-03-04 Imperial Chemical Industries Plc 4,4'-Alkylenedipiperidine derivatives
US4670592A (en) * 1983-05-09 1987-06-02 Imperial Chemical Industries Plc Bisbiguanide compounds
US4590070A (en) * 1983-10-14 1986-05-20 Imperial Chemical Industries Plc Contraceptive methods
US4602042A (en) * 1983-10-14 1986-07-22 Imperial Chemical Industries Plc Contraceptive methods
AU573234B2 (en) * 1983-10-14 1988-06-02 Victoria University Of Manchester, The Polymeric biguanide as contraceptive
US4567174A (en) * 1984-05-07 1986-01-28 Imperial Chemical Industries Plc Bis(1-substituted biguanide) derivatives
GR890100292A (en) * 1988-05-03 1990-03-12 Ici Plc Cleaning agent for dentine surfaces
FR2631038A1 (en) * 1988-05-03 1989-11-10 Ici Plc PROCESS FOR IMPROVING THE ADHESIVE OF AN ADHESIVE ON THE SURFACE OF A HARD TISSUE
BE1002203A5 (en) * 1988-05-03 1990-10-09 Ici Plc SURFACE TREATMENT OF HARD FABRIC.
US5023107A (en) * 1988-05-03 1991-06-11 Imperial Chemical Industries Plc Hard tissue surface treatment
EP0507317A2 (en) * 1991-04-05 1992-10-07 Otsuka Pharmaceutical Co., Ltd. Biguanide derivatives, manufacturing method thereof, and disinfectants containing the derivatives
EP0507317A3 (en) * 1991-04-05 1993-02-24 Otsuka Pharmaceutical Co., Ltd. Biguanide derivatives, manufacturing method thereof, and disinfectants containing the derivatives
US5376686A (en) * 1991-04-05 1994-12-27 Otsuka Pharmaceutical Co., Ltd. Biguanide derivatives, manufacturing method thereof, and disinfectants containing the derivatives
WO1998020913A1 (en) * 1996-11-13 1998-05-22 Bausch & Lomb Incorporated Method for providing rapid disinfection of contact lenses
US5965088A (en) * 1997-10-23 1999-10-12 Lever; Andrea M. Method for providing rapid disinfection of contact lenses
AT411060B (en) * 2000-10-23 2003-09-25 P O C Oil Industry Technology New polymeric guanidine derivatives, used as disinfectant in (veterinary) medicine, waste liquor purification or domestic or trade application, are polycondensates of diamine with oxyalkylene chain and guanidine acid addition salt
FR2841778A1 (en) * 2002-07-05 2004-01-09 Oreal Composition for dyeing keratinic fibers, e.g. human hair, comprises a polyguanidine derivative
WO2008013555A1 (en) * 2006-07-26 2008-01-31 Watervisions International, Inc. Broad spectrum antimicrobial purification materials and methods for purifying fluids
US7427409B2 (en) 2006-07-26 2008-09-23 Water Visions International, Inc. Broad spectrum antimicrobial purification materials and methods for purifying fluids
US9567294B2 (en) 2013-01-25 2017-02-14 Sealife Pharma Gmbh Bioactive polymers
WO2014113835A1 (en) * 2013-01-25 2014-07-31 Sealife Pharma Gmbh New bioactive polymers
AT513858A4 (en) * 2013-01-25 2014-08-15 Sealife Pharma Gmbh New bioactive polymers
AT513858B1 (en) * 2013-01-25 2014-08-15 Sealife Pharma Gmbh New bioactive polymers
EA031075B1 (en) * 2013-01-25 2018-11-30 Силайф Фарма Гмбх Polyguanidine derivatives as biocides
WO2014174237A1 (en) 2013-04-26 2014-10-30 Biointeractions Limited Bioactive coatings
US10206945B2 (en) 2013-04-26 2019-02-19 Biointeractions Ltd. Bioactive coatings
EP3699220A1 (en) 2013-04-26 2020-08-26 Biointeractions Ltd Bioactive coatings
USRE49522E1 (en) 2013-04-26 2023-05-09 Biointeractions Ltd. Bioactive coatings
USRE49528E1 (en) 2013-04-26 2023-05-16 Biointeractions Ltd. Bioactive coatings
AT516070B1 (en) * 2014-07-31 2016-08-15 Sealife Pharma Gmbh Process for the preparation of polyguanidines
AT516070A1 (en) * 2014-07-31 2016-02-15 Sealife Pharma Gmbh Process for the preparation of polyguanidines
US10335431B2 (en) 2014-07-31 2019-07-02 Sealife Pharma Gmbh Method for producing polyguanidines
US11013760B2 (en) 2014-07-31 2021-05-25 Sealife Pharma Gmbh Polyguanidine polymers and methods of use thereof
WO2016055644A1 (en) * 2014-10-10 2016-04-14 Lead Discovery Siena S.R.L. Linear guanidine derivatives, methods of preparation and uses thereof
US10004702B2 (en) 2014-10-10 2018-06-26 Lead Discovery Siena S.R.L. Linear guanidine derivatives, methods of preparation and uses thereof
EP3524055A1 (en) 2018-02-08 2019-08-14 BCSK Biocid GmbH Antibacterial and spermicidal lubricant
WO2019154983A1 (en) 2018-02-08 2019-08-15 Bcsk Biocid Gmbh Antibacterial and spermicidal lubricant

Also Published As

Publication number Publication date
DOP1965001173A (en) 1971-05-30
BR6568736D0 (en) 1973-08-14
DE1493210B2 (en) 1976-04-22
ES311586A1 (en) 1965-07-16
CH486429A (en) 1970-02-28
FR1463818A (en) 1966-07-22
DE1493210A1 (en) 1969-04-03

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