Claims
- 1. A compound having the formula ##STR6## wherein: Y is an alkylene group containing from 4 to 18 carbon atoms and separating the two 4-(R--NH)--1-pyridinyl groups by from 4 to 18 carbon atoms;
- R is an alkyl group containing from 6 to 18 carbon atoms, a cycloalkyl group containing from 5 to 7 carbon atoms, benzyl, or phenyl substituted by methylenedioxy or one or two substituents selected from the group consisting of halogen, lower-alkyl, lower-alkoxy, nitro, cyano and trifluoromethyl;
- R.sub.1 is hydrogen or lower alkyl;
- A is an anion;
- m is 1 or 3;
- n is 1 or 2;
- x is 1, 2 or 3; and
- wherein
- (m)(2)=(n)(x).
- 2. A compound having the formula ##STR7## wherein: Y is an alkylene group containing from 4 to 18 carbon atoms and separating the two 4--(R--NH)-1-pyridinyl groups by from 4 to 18 carbon atoms;
- R is an alkyl group containing from 6 to 18 carbon atoms;
- R.sub.1 is hydrogen or lower alkyl;
- A is an anion;
- m is 1 or 3;
- n is 1 or 2;
- x is 1, 2 or 3; and
- wherein
- (m)(2)=(n)(x).
- 3. A compound according to claim 2 wherein R.sub.1 is hydrogen, Y is (CH.sub.2).sub.w and w is from 4 to 18.
- 4. A compound according to claim 3 wherein w is from 8 to 12.
- 5. A compound according to claim 4 wherein R is an alkyl group containing from 7 to 9 carbon atoms.
- 6. A compound according to claim 5 wherein A is chloride or bromide.
- 7. A compound having the formula ##STR8## wherein: Y is an alkylene group containing from 4 to 18 carbon atoms and separating the two 4--(R--NH)-1-pyridinyl groups by from 4 to 18 carbon atoms;
- R is a cycloalkyl group containing from 5 to 7 carbon atoms;
- R.sub.1 is hydrogen or lower alkyl;
- A is an anion;
- m is 1 or 3;
- n is 1 or 2;
- x is 1, 2 or 3; and
- wherein
- (m)(2)=(n)(x).
- 8. A compound according to claim 7 wherein R.sub.1 is hydrogen, Y is (CH.sub.2).sub.w and w is from 4 to 18.
- 9. A compound according to claim 8 wherein w is from 8 to 12 and R is cyclohexyl.
- 10. A compound having the formula ##STR9## wherein: Y is an alkylene group containing from 4 to 18 carbon atoms and separating the two 4-(R-NH)-1-pyridinyl groups by from 4 to 18 carbon atoms;
- R is phenyl substituted by methylenedioxy or one or two substituents selected from the group consisting of halogen, lower-alkyl, lower-alkoxy, nitro, cyano and trifluoromethyl;
- R.sub.1 is hydrogen or lower alkyl;
- A is an anion;
- m is 1 or 3;
- n is 1 or 2;
- x is 1, 2 or 3; and
- wherein
- (m)(2)=(n)(x).
- 11. A compound according to claim 10 wherein R.sub.1 is hydrogen, Y is (CH.sub.2).sub.w and w is from 4 to 18.
- 12. A compound according to claim 11 wherein w is from 8 to 12 and R is p-chlorophenyl.
- 13. A compound having the formula ##STR10## wherein: Y is an alkylene group containing from 4 to 18 carbon atoms and separating the two 4-(R-NH)-1-pyridinyl groups by from 4 to 18 carbon atoms;
- R is benzyl;
- R.sub.1 is hydrogen or lower alkyl;
- A is an anion;
- m is 1 or 3;
- n is 1 or 2;
- x is 1, 2 or 3; and
- wherein
- (m)(2)=(n)(x).
- 14. A compound according to claim 13 wherein R.sub.1 is hydrogen, Y is (CH.sub.2).sub.w and w is from 8 to 12.
- 15. 1,12-Bis-[4-(heptylamino)-1-pyridinium]dodecane dibromide according to claim 6.
- 16. 1,12-Bis-[4-(heptylamino)-1-pyridinium]dodecane dichloride according to claim 6.
- 17. 1,10-Bis-[4-(octylamino)-1-pyridinium]decane dibromide according to claim 6.
- 18. 1,10-Bis-[4-(octylamino)-1-pyridinium]decane dichloride according to claim 6.
- 19. 1,12-Bis-[4-(2-ethylhexylamino)-1-pyridinium]-dodecane dibromide according to claim 6.
- 20. 1,12-Bis-[4-(2-ethylhexylamino)-1-pyridinium]dodecane dichloride according to claim 6.
- 21. A compound selected from the group consisting of:
- 1,9-bis-[4-(heptylamino)-1-pyridinium]nonane dibromide,
- 1,10-bis-[4-(2-ethylhexylamino)-1-pyridinium]-decane dibromide,
- 1,10-bis-[4-(octylamino)-1-pyridinium]decane dichloride,
- 1,9-bis-[4-(octylamino)-1-pyridinium]nonane dibromide,
- 1,12-bis-[4-(heptylamino)-1-pyridinium]dodecane dichloride,
- 1,8-bis-[4-(octylamino)-1-pyridinium]octane dibromide and
- 1,10-bis-[4-(octylamino)-1-pyridinium]decane dibromide.
- 22. 1.9-Bis-[4-(heptylamino)-1-pyridinium]nonane dibromide according to claim 21.
- 23. 1,10-Bis-[4-(2-ethylhexylamino)-1-pyridinium]-decane dibromide according to claim 21.
- 24. 1,10-Bis-[4-(propylamino)-1-pyridinium]decane dibromide.
- 25. An antimicrobial composition suitable for topical administration comprising an effective amount of a compound according to claim 1 wherein A is a pharmaceutically acceptable anion and a compatible, pharmaceutically acceptable carrier.
- 26. A skin-cleansing composition comprising an antimicrobially effective amount of a compound according to claim 1 wherein A is a pharmaceutically acceptable anion, a compatible, pharmaceutically acceptable surfactant and a compatible, pharmaceutically acceptable carrier.
- 27. A skin-cleansing composition comprising an antimicrobially effective amount of a compound according to claim 5 wherein A is a pharmaceutically acceptable anion, a compatible pharmaceutically acceptable surfactant and a compatible, pharmaceutically acceptable carrier.
- 28. An oral hygiene composition for the prevention of dental plaque comprising an effective amount of a compound according to claim 21 wherein A is a pharmaceutically acceptable anion and a compatible, pharmaceutically acceptable carrier.
- 29. An antimicrobial composition suitable for application to inanimate surfaces comprising an effective amount of a compound according to claim 1 in admixture with a compatible vehicle.
- 30. A method for controlling microorganisms which comprises contacting said microorganisms with an antimicrobially effective amount of a compound of the formula ##STR11## wherein: Y is an alkylene group containing from 4 to 18 carbon atoms and separating the two 4-(R-NH)-1-pyridinyl groups by from 4 to 18 carbon atoms;
- R is hydrogen, an alkyl group containing from 1 to 18 carbon atoms, a cycloalkyl group containing from 5 to 7 carbon atoms, benzyl, or phenyl substituted by methylenedioxy or one or two substituents selected from the group consisting of halogen, lower-alkyl, lower-alkoxy, nitro, cyano and trifluoromethyl;
- R.sub.1 is hydrogen or lower alkyl;
- A is an anion;
- m is 1 or 3;
- n is 1 or 2;
- x is 1, 2 or 3; and
- wherein
- (m)(2)=(n)(x).
- 31. A method according to claim 30 wherein R is hydrogen.
- 32. A method according to claim 30 wherein R is an alkyl group containing from 1 to 18 carbon atoms, a cycloalkyl group containing from 5 to 7 carbon atoms, benzyl, or phenyl substituted by methylenedioxy or one or two substituents selected from the group consisting of halogen, lower-alkyl, lower-alkoxy, nitro, cyano and trifluoromethyl.
- 33. A method for controlling microorganisms which comprises contacting said microorganisms with an antimicrobially effective amount of a compound according to claim 3.
- 34. A method for controlling microorganisms which comprises contacting said microorganisms with an antimicrobially effective amount of a compound according to claim 5.
- 35. A method according to claim 34 wherein the antimicrobially effective agent is 1,12-bis-[4-(heptylamino)-1-pyridinium]dodecane dibromide.
- 36. A method according to claim 34 wherein the antimicrobially effective agent is 1,12-bis-[4-(heptylamino)-1-pyridinium]dodecane dichloride.
- 37. A method according to claim 34 wherein the antimicrobially effective agent is 1,10-bis-[4-(octylamino)-1-pyridinium]decane dibromide.
- 38. A method according to claim 34 wherein the antimicrobially effective agent is 1,10-bis-[4-(octylamino)-1-pyridinium]decane dichloride.
- 39. A method according to claim 34 wherein the antimicrobially effective agent is 1,12-bis-[4-(2-ethylhexylamino)-1-pyridinium]dodecane dibromide.
- 40. A method according to claim 34 wherein the antimicrobially effective agent is 1,12-bis-[4-(2-ethylhexylamino)-1pyridinium]dodecane dichloride.
- 41. A method of treating teeth for preventing the formation of dental plaque thereon which comprises contacting the teeth with an effective amount of a compound according to claim 21.
- 42. A method according to claim 41 wherein the dental plaque-preventive agent is 1,9-bis-[4-(heptylamino)-1-pyridinium]nonane dibromide.
- 43. A method according to claim 41 wherein the dental plaque-preventive agent is 1,10-bis-[4-(2-ethylhexylamino)-1-pyridinium]decane dibromide.
- 44. A method according to claim 41 wherein the dental plaque-preventive agent is 1,10-bis-[4-(octylamino)-1-pyridinium]decane dichloride.
- 45. A method according to claim 41 wherein the dental plaque-preventive agent is 1,9-bis-[4-(octylamino)-1-pyridinium]nonane dibromide.
Priority Claims (1)
Number |
Date |
Country |
Kind |
5784/77 |
Feb 1977 |
GBX |
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CROSS-REFERENCE TO RELATED APPLICATION
This application is a continuation-in-part of prior copending application Ser. No. 721,315, filed Sept. 7, 1976, now abandoned, in turn a continuation-in-part of application Ser. No. 661,101, filed Feb. 25, 1976 and now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
3055902 |
Walker |
Sep 1962 |
|
3786058 |
Edwards |
Jan 1974 |
|
Non-Patent Literature Citations (2)
Entry |
Walker et al., J. Org. Chem., vol. 26, pp. 2740-2747, (1961). |
Austin, J. Pharm. Pharmacol., vol. 11, pp. 80-93, (1959). |
Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
721315 |
Sep 1976 |
|
Parent |
661101 |
Feb 1976 |
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