Use of substitute 2,4-bis (alkylamino)pyrimidines

• US 20060188453A1
• Filed: 07/16/2004
• Published: 08/24/2006
• Est. Priority Date: 07/25/2003
• Status: Active Grant

• Current Assignee: Ciba Specialty Chemicals Corp (BASF SE)
• Original Assignee: Ciba Specialty Chemicals Corp (BASF SE)
• Inventors: Marquais-Bienewald, Sophie, Preuss, Andrea, Mehlin, Andreas, Holzl, Werner
• Granted Patent: US 7,722,893 B2
• Time in Patent Office: Days
• US Class Current: 424/49
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A61K 8/4953 containing pyrimidine ring derivatives, e.g. minoxidil
• CPC Class Codes: A61L 2/16 using chemical substances
• CPC Class Codes: A61L 2/18 Liquid substances or solutions comprising solids or dissolved gases
• CPC Class Codes: A61P 7/00 Drugs for disorders of the blood or the extracellular fluid
• CPC Class Codes: A61Q 11/00 Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
• CPC Class Codes: A61Q 17/005 Antimicrobial preparations
• CPC Class Codes: C11D 3/28 Heterocyclic compounds containing nitrogen in the ring
• CPC Class Codes: C11D 3/48 Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
• CPC Class Codes: D06M 13/355 having six-membered heterocyclic rings
• CPC Class Codes: Y10T 442/2525 Coating or impregnation functions biologically [e.g., insect repellent, antiseptic, insecticide, bactericide, etc.]

Abstract

The use of 2,4—bis(alkylamino)pyrimidines of formula (1) R₁ is C₁-C₁₂alkyl or C₆-C₁₀laryl; R₂ is hydrogen or C₁-C₁₂alkyl; or R₁ and R₂ together form a radical of formula (1a) R′ and R″ are each independently of the other hydrogen, C₁-C₆alkyl or C₁-C₆alkoxy, R₃ and R₅ are each independently of the other hydrogen or C₁-C₈alkyl; R₄ is C₁-C₂₀alkyl, unsubstituted phenyl, C₆-C₁₀aryl, C₆-C₁₀aryl—C₁-C₆alkyl, hydroxy—C₁-C₆alkyl, di—C₁-C₆al—ky—lamino—C ₁-C₆alkyl, mono—C₁-C₆alkylamino—C₁-C₆alkyl,—(CH₂)2—(O—(CH₂)₂)₁—₄-OH or —(CH₂)₂-(O—(CH₂)₂)₁—₄-NH₂; R₆ is C₁-C₂₀alkyl, C₆-C₁₀aryl, C₆-C₁₀aryl—C₁-C₆alkyl, hydroxy—C₁-C₆alkyl, di—C₁C₆alkylamino—C₁-C₆alkyl, mono—C₁-C₆alkylamino—C₁-C ₆alkyl, —(CH₂)₂-(O—(CH₂)₂)₁—₄-OH or —(CH₂)₂-(O—(CH₂)₂)₁—₄-NH₂; or R₃ and R ₄ and/or R₅ and R₆, together form a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring; in the antimicrobial treatment of surfaces.

Claims

1-21. -21. (canceled)

22. A method for the antimicrobial treatment of a surface, which comprises contacting said surface with an antimicrobially effective amount of a 2,4-bis(alkylamino)pyrimidine of formula

23. A method according to claim 22, wherein R₁ is C₁-C₈alkyl or phenyl.

24. A method according to claim 22, wherein R₂ is hydrogen or C₃-C₈alkyl.

25. A method according to claim 22, wherein R₃ and R₅ are each independently of the other hydrogen or C₁-C₈alkyl.

26. A method according to claim 22, wherein R₄ is C₁-Cl₂alkyl, unsubstituted phenyl, C₆-C₁₀aryl-C₁-C₆alkyl, hydroxy—

C₂-C₆alkyl, di—

C₁-C₄alkylamino—

C₁-C₄alkyl, mono—

C₁-C₄alkylamino—

C₁-C₄alkyl, —

(CH₂)₂-(O—

(CH₂)₂)₁,₂-OH or —

(CH₂)₂-(O—

(CH₂)₂)₁,₂-NH₂; and

R₆ is C₁-Cl₂alkyl, C₆-C₁₀aryl, C₆-C₁₀aryl-C₁-C₆alkyl, hydroxy—

C₂-C₆alkyl, di—

C₁-C₄alkylamino—

C₁-C₄alkyl, mono—

C₁-C₄alkylamino—

C₁-C₄alkyl, —

(CH₂)₂-(O—

(CH₂)₂)_{1 2}-OH or —

(CH₂)₂-(O—

(CH₂)₂)_{1 2}-NH₂.

27. A method according to claim 22, wherein R₁ is C₁-C₈alkyl or phenyl;

R₂ is hydrogen or hexyl; and

R₃ and R₅ are each independently of the other hydrogen or C₁-C₈alkyl;

R₄ is C₁-Cl₂alkyl, unsubstituted phenyl, C₆-C₁₀aryl-C₁-C₆alkyl, hydroxy—

C₂-C₆alkyl, di—

C₁-C₄alkylamino—

C₁-C₄alkyl, mono—

C₁-C₄alkylamino—

C₁-C₄alkyl, —

(CH₂)₂-(O—

(CH₂)₂)₁,₂-OH or —

(CH₂)₂-(O—

(CH₂)₂)₁,₂-NH₂; and

R₆ is C₁-Cl₂alkyl, C₆-C₁₀aryl, C₆-C₁₀aryl-C₁-C₆alkyl, hydroxy—

C₂-C₆alkyl, di—

C₁-C₄alkylamino—

C₁-C₄alkyl, mono—

C₁-C₄alkylamino—

C₁-C₄alkyl, —

(CH₂)₂-(O—

(CH₂)₂)₁,₂-OH or —

(CH₂)₂-(O—

(CH₂)₂)₁,₂-NH₂;

or R₃ and R₄ and/or R₅ and R₆ together form a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring.

28. A method according to claim 22, relating to compounds of formula

29. A method according to claim 22, wherein R₁ is C₁-C₄alkyl or phenyl;

R₂ is hydrogen or hexyl;

or R. and R₂ together form a radical of formula (la) as defined in claim 22, wherein R′

is hydrogen, C₁-C₃alkyl or C₁-C₃alkoxy, and R″

is C₁-C₃alkyl or C₁-C₃alkoxy;

R₃ and R₅ are each independently of the other hydrogen or C₁-C₈alkyl;

R₄ is C₁-Cl₂alkyl, unsubstituted phenyl, C₆-Cl₀aryl-C₁-C₆alkyl, hydroxy—

C₂-C₆alkyl, di—

C,-C₄alkylamino—

C,-C₄alkyl, mono—

C,-C₄alkylamino—

C₁-C₄alkyl, —

(CH₂)₂-(O—

(CH₂)₂)₁,₂-OH or —

(CH₂)₂-(O—

(CH₂)₂)₁,₂-NH₂; and

R₆ is C₁-Cl₂alkyl, C₆-Cl₀aryl, C₆-C₁₀aryl-Cl-C₆alkyl, hydroxy—

C₂-C₆alkyl, di—

C₁-C₄alkylamino—

C₁-C₄alkyl, mono—

C₁-C₄alkylamino—

C₁-C₄alkyl, —

(CH₂)₂-(O—

(CH₂)₂)₁,₂-OH or —

(CH₂)₂-(O—

(CH₂)₂)₁,₂-NH₂;

or R₃ and R₄ together, and R₅ and R₆ together, form a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring.

30. A method according to claim 22, wherein R₃ and R₅, and R₄ and R₆, have the same meanings.

31. A method according to claim 22, wherein the 2,4-bis(alkylamino)pyrimidine is of the formula

32. A process for the preparation of a compound of formula (1) according to claim 22, which comprises reacting a dichloropyrimidine compound of formula (1 b), wherein R₁ and R₂ are as defined in claim 22, with a primary or secondary amine, wherein R₃, R4, R₅ and R₆ are as defined above in claim 22, in a suitable solvent and an auxiliary base or using an excess of amine to form a compound of formula (1) according to the following Scheme:

33. A method according to claim 22, wherein the surface comprises textile fibre materials.

34. A method according to claim 22, wherein the treatment with a compound of formula (1) results in preservation.

35. A method according to claim 22, wherein a compound of formula (1) is incorporated into washing and cleaning formulations.

36. A method according to claim 22 wherein a compound of formula (1) imparts antimicrobial properties to, and preserves, plastics, paper, nonwovens, wood or leather.

37. A method according to claim 22, wherein a compound of formula (1) imparts antimicrobial properties to, and preserves, technical products selected from printing ink thickners consisting of starch or of cellulose derivatives, surface-coating compositions and paints.

38. A method according to claim 22, wherein a compound of formula (1) functions as a biocide in technical processes.

39. A method according to claim 22, wherein a compound of formula (1) is incorporated into a skin-care preparation or mouth-care preparation.

40. A personal care preparation containing from 0.01 to 15 % by weight, based on the total weight of the composition, of a compound of formula (1) according to claim 22 and a cosmetically tolerable adjuvant.

41. An oral composition containing from 0.01 to 15 % by weight, based on the total weight of the composition, of a compound of formula (1) according to claim 22 and an orally tolerable adjuvant.

42. A skin-care preparation containing from 0.01 to 15 % by weight, based on the total weight of the composition, of a compound of formula (1) according to claim 22 and adjuvants tolerated by the skin.