GB1095902A - Guanidine derivatives - Google Patents
Guanidine derivativesInfo
- 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
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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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.
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)
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)
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 |
-
1965
- 1965-04-07 BR BR168736/65A patent/BR6568736D0/en unknown
- 1965-04-08 GB GB15025/65A patent/GB1095902A/en not_active Expired
- 1965-04-08 FR FR12484A patent/FR1463818A/en not_active Expired
- 1965-04-08 CH CH489965A patent/CH486429A/en not_active IP Right Cessation
- 1965-04-08 ES ES0311586A patent/ES311586A1/en not_active Expired
- 1965-04-09 DE DE1965ST023662 patent/DE1493210B2/en active Granted
- 1965-04-09 DO DO1965001173A patent/DOP1965001173A/en unknown
Cited By (40)
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 |
---|---|
DE1493210A1 (en) | 1969-04-03 |
FR1463818A (en) | 1966-07-22 |
DOP1965001173A (en) | 1971-05-30 |
CH486429A (en) | 1970-02-28 |
BR6568736D0 (en) | 1973-08-14 |
ES311586A1 (en) | 1965-07-16 |
DE1493210B2 (en) | 1976-04-22 |
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