GB978855A - 1,1-(alkylene)bis(5-arylbiguanides), acid-addition salts thereof, and disinfecting oranitizing compositions containing same - Google Patents

1,1-(alkylene)bis(5-arylbiguanides), acid-addition salts thereof, and disinfecting oranitizing compositions containing same

Info

Publication number
GB978855A
GB978855A GB1312961A GB1312961A GB978855A GB 978855 A GB978855 A GB 978855A GB 1312961 A GB1312961 A GB 1312961A GB 1312961 A GB1312961 A GB 1312961A GB 978855 A GB978855 A GB 978855A
Authority
GB
United Kingdom
Prior art keywords
alkyl
nitro
formula
hydrogen
halogen
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
GB1312961A
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 GB978855A publication Critical patent/GB978855A/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
    • 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

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0978855/C1/1> (wherein CnH2n represents a bivalent alkylene bridge in which the free valence bonds are on two different carbon atoms and n is an integer from 2 to 12, and Q and Q1 each represent substituted phenyl having the formula <FORM:0978855/C1/2> wherein Y is hydrogen, halogen, trifluoromethyl, nitro, C1- 6 alkyl-O-, C1- 6 alkyl-S-, C1- 6 alkyl-SO- or C1- 6 alkyl-SO2-, Z is hydrogen, halogen, nitro, C1- 6 alkyl or C1- 6 alkyl-O-, R is alkyl, halo-C1- 6 alkyl, C2- 6 alkenyl, benzyl, ar-halobenzyl, ar-nitrobenzyl, ar-C1- 6 alkylbenzyl, ar-C1- 6 alkoxybenzyl, cyclohexyl, phenyl, C1- 6 alkylphenyl, nitrophenyl, C1- 6 alkoxyphenyl, halophenyl or, when neither Y nor Z is nitro, ar-aminobenzyl or aminophenyl, and X is -S-, -SO- or -SO2-) and acid addition salts thereof (including those with acidic resins-see Division C3), and their preparation by (a) reacting a 1,11(alkylene) bis (3-cyanoguanidine) of the formula <FORM:0978855/C1/3> with approximately two molecular proportions of an arylamine, preferably as an acid addition salt, of the formula <FORM:0978855/C1/4> (wherein R1 represents any of the values of R except ar-aminobenzyl or aminophenyl), or (b) reacting an alkylenediamine, as an acid addition salt, of the formula <FORM:0978855/C1/5> with approximately two molecular proportions of a 1-aryl-3-cyanoguanidine of the formula <FORM:0978855/C1/6> optionally followed in either case by (a) reduction of a compound wherein R1 is ar-nitrobenzyl or nitrophenyl and neither Y nor Z is nitro to the corresponding ar-aminobenzyl or aminophenyl compound, (b) oxidation of a compound wherein X is -S- or -SO- to the corresponding compound wherein X is -SO- or -SO2-, respectively, and/or (c) salt formation or conversion of a salt to the free base. The 1-aryl-3-cyanoguanidine starting materials are prepared by reacting approximately equimolecular amounts of a corresponding arylamine acid addition salt and an alkali metal dicyanamide. 4-n-Propylsulphinyl-3-chloroaniline is prepared by oxidizing 4-n-propylmercapto-3-chloroaniline hydrochloride with hydrogen peroxide in aqueous acetic acid, and is converted to the hydrochloride. The compounds of the invention have bactericidal, bacteriostatic, fungicidal and fungistatic activity, some of them have antiviral activity and others have amebacidal activity (see Division A5). Reference is made to the treatment with them of various disorders in animals.ALSO:The invention comprises addition salts of compounds of the general formula <FORM:0978855/C3/1> (wherein CnH2n represents a bivalent alkylene bridge in which the free valence bonds are on two different carbon atoms and n is an integer from 2 to 12, and Q and Q1 each represent substituted phenyl having the formula <FORM:0978855/C3/2> wherein Y is hydrogen, halogen, trifluoromethyl, nitro, C1-6 alkyl -O-, C1-6 alkyl-S-, C1-6 alkyl-SO- or C1-6 alkyl-SO2, Z is hydrogen, halogen, nitro, C1-6 alkyl or C1-6 alkyl-O-, R is alkyl, halo-C1-6 alkyl, C2-6 alkenyl, benzyl, ar-halobenzyl, ar-nitrobenzyl, ar-C1-6 alkylbenzyl, ar-C1-6 alkoxybenzyl, cyclohexyl, phenyl, C1-6 alkylphenyl, nitrophenyl, C1-6 alkoxyphenyl, halophenyl or, when neither Y nor Z is nitro, ar-aminobenzyl or aminophenyl, and X is -S-, -SO- or -SO2-) with acidic resins, e.g. sulphonated polystyrene.ALSO:The invention comprises disinfecting and sanitizing compositions containing a compound of the general formula <FORM:0978855/A5-A6/1> (wherein CnH2n represents a bivalent alkylene bridge in which the free valence bonds are on two different carbon atoms and n is an integer from 2 to 12, and Q and Q1 each represent substituted phenyl having the formula <FORM:0978855/A5-A6/2> wherein Y is hydrogen, halogen, trifluoromethyl, nitro, C1-6 alkyl-O-, C1-6 alkyl-S-, C1-6 alkyl-SO- or C1-6 alkyl-SO2-, Z is hydrogen, halogen, nitro, C1-6 alkyl or C1-6 alkyl-O-, R is alkyl, halo-C1-6 alkyl, C2-6 alkenyl, benzyl, ar-halobenzyl, ar-nitrobenzyl, ar-C1-6 alkylbenzyl, ar-C1-6 alkoxybenzyl, cyclohexyl, phenyl, C1-6 alkylphenyl, nitrophenyl, C1-6 alkoxyphenyl, halophenyl or, when neither Y or Z is nitro, ar-aminobenzyl or aminophenyl, and X is -S-, -SO- or -SO2-), or an acid addition salt thereof (including those with acidic resins), many are specified, and a carrier. The active ingredients may be used in soap solution or sulfonate detergent solution to treat cotton cloth.
GB1312961A 1960-04-18 1961-04-12 1,1-(alkylene)bis(5-arylbiguanides), acid-addition salts thereof, and disinfecting oranitizing compositions containing same Expired GB978855A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US2269260A 1960-04-18 1960-04-18

Publications (1)

Publication Number Publication Date
GB978855A true GB978855A (en) 1964-12-23

Family

ID=21810934

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1312961A Expired GB978855A (en) 1960-04-18 1961-04-12 1,1-(alkylene)bis(5-arylbiguanides), acid-addition salts thereof, and disinfecting oranitizing compositions containing same

Country Status (3)

Country Link
CH (3) CH437649A (en)
FR (2) FR1309831A (en)
GB (1) GB978855A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4359555A (en) 1979-06-29 1982-11-16 Ciba-Geigy Corporation Salts formed from formamidines with polymers containing sulfonic acid groups
GB2349644A (en) * 1999-05-01 2000-11-08 Biointeractions Ltd Infection resistant polymers, methods for their preparation, and their uses

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0113070B1 (en) * 1982-12-20 1988-01-13 American Cyanamid Company The use of substituted nitro and cyanoguanidines for increasing crop yield

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4359555A (en) 1979-06-29 1982-11-16 Ciba-Geigy Corporation Salts formed from formamidines with polymers containing sulfonic acid groups
GB2349644A (en) * 1999-05-01 2000-11-08 Biointeractions Ltd Infection resistant polymers, methods for their preparation, and their uses
US7771743B1 (en) 1999-05-01 2010-08-10 Biointeractions, Ltd. Infection resistant polymers, their preparation and uses

Also Published As

Publication number Publication date
FR1582M (en) 1962-11-26
FR1309831A (en) 1962-11-23
CH407980A (en) 1966-02-28
CH437649A (en) 1967-06-15
CH421939A (en) 1966-10-15

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