US2004259958A1PendingUtilityA1
Non-halogenated phenoxy and/or benzyloxy substituted phenols, antimicrobial compositions containing the same, and methods of using the same
Priority: Dec 20, 2000Filed: Jun 14, 2004Published: Dec 23, 2004
Est. expiryDec 20, 2020(expired)· nominal 20-yr term from priority
C07C 43/23A61K 8/347C07C 43/295A01N 31/16A61Q 11/00
42
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Claims
Abstract
Antimicrobial compounds, compositions containing the same, and methods of using of the same for reducing the presence of microorganisms on a substrate or in a fluid environment comprising an antimicrobial effective carrier and at least one antimicrobial compounds including non-halogenated phenoxy and/or benzyloxy substituted phenol compounds.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . The compound of Formula (1):
wherein
R 1 is selected from the group
R 2 and R 3 are each independently selected from the group consisting of hydrogen; an alkyl group; a cycloalkyl group; an alkenyl group; a cycloalkenyl group; a hydroxyalkyl group; a hydroxycycloalkyl group; an alkyl group substituted with phenyl in which phenyl is optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; phenyl optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; and benzyl optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group;
R 4 is selected from the group consisting of hydrogen, an alkyl group, a cycloalkyl group, benzyl, and phenyl;
R 5 is selected from the group consisting of hydroxyl, benzyl, alkoxy, hydroxyalkyl, and cycloalkyl optionally substituted with hydroxyl; and
R 6 and R 7 are each independently selected from the group consisting of hydrogen; an alkyl group; a cycloalkyl group; an alkenyl group; a cycloalkenyl group; benzyl, an alkoxy group; phenyl optionally substituted with an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; an alkyl group substituted with phenyl in which phenyl is optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; phenoxy; and benzyloxy;
with the proviso that:
a) when R 1 is a
and R 2 and R 4 are each hydrogen, and
1) when R 3 is hydrogen, then R 6 is not hydrogen, methyl, tert-butyl, phenyl, or phenoxy;
2) when R 5 is hydroxyl and one of R 3 and R 6 is hydrogen, then the other ot R 3 and R 6 is not selected from the group consisting of hydrogen, n-propyl, n-butyl, n-pentyl, 1-methylethyl, 2-methylpropyl, 3-methylbutyl, benzyl, or cyclohexyl;
3) when R 3 and R 6 are each hydrogen, then R 5 is not benzyl;
4) when R 5 is hydroxyl and R 3 is ethyl, then R 6 is not methyl;
5) when R 5 is hydroxyl and R 3 is tert-butyl, then R 6 is not tert-butyl;
b) when R 1 is a
R 3 , R 4 and R 6 are each hydrogen, and R 5 is hydroxyl, then R 2 is not selected from the group consisting of phenyl and tert-butyl;
c) when R 1 is a
R 5 is hydroxyl, and R 6 is hydrogen, then none of R 2 , R 3 , and R 4 is C 1 -C 4 alkyl, the other two of R 2 , R 3 , and R 4 being hydrogen;
d) when R 1 is a
at least one of R 2 , R 3 and R 4 is not hydrogen, and
e) when R 1 is a
each of R 2 , and R 3 is hydrogen, R 7 and R 4 is tert-butyl, then R 7 is not hydrogen
2 . The compound of claim 1 wherein each of R 3 , and R 6 are selected from the group consisting of straight and branched alkyl groups.
3 . The compound of claim 1 wherein each of R 3 , R 5 , and R 6 is a cycloalkyl group.
4 . The compound of claim 1 further including a member selected from the group consisting of 2-(2-hydroxyphenoxy)-5-heptylphenol, 2-(2-hydroxyphenoxy)-5-octylphenol, 2-but-2-enyl-6-(2-methoxyphenoxy)phenol, 2-(2-methoxyphenoxy)-6-butylphenol, 2-(2-hydroxyphenoxy),6-(3-hydroxypropyl)phenol, 6-(2-hydroxypropyl)-2-(2-methoxyphenoxy)phenol, 6-(3-hydroxypropyl)-2-(2-methoxyphenoxy)phenol, 6-(3-hydroxy-1-methylpropyl)-2-(2-hydroxyphenoxy)phenol, 6-(1-methyl-3-hydroxypropyl)-2-(2-methoxyphenoxy)phenol, 2-(2-hydroxyphenoxy)-6-(2-hydroxycyclohexyl)phenol, 2-(2-hydroxyphenoxy)-6-(3-hydroxycyclohexyl)phenol, 2-(2-methoxyphenoxy)-6-prop-2-enylphenol, 2-(2-methoxyphenoxy)-6-(1-methylprop-2-enyl)phenol, 2-(2-methoxyphenoxy)-6-propylphenol, 2-tert-butyl-6-phenylmethoxyphenol, 2-phenylmethoxy-4-cyclohexylphenol, 2-(2-hydroxy-4-tert-butylphenoxy)-6-propylphenol, 2-(2-hydroxyphenoxy)-5-cyclohexylmethylphenol, 2-(2-hydroxyphenoxy)-6-cyclohexylphenol.
5 . An antimicrobial composition comprising an antimicrobial effective amount of at least one antimicrobial compound of Formula (II):
wherein
R 1 is selected from the group
R 2 and R 3 are each independently selected from the group consisting of hydrogen; an alkyl group; a cycloalkyl group; an alkenyl group; a cycloalkenyl group; a hydroxyalkyl group; a hydroxycycloalkyl group; an alkyl group substituted with phenyl in which phenyl is optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; phenyl optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; and benzyl optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group;
R 4 is selected from the group consisting of hydrogen, an alkyl group, a cycloalkyl group, benzyl, and phenyl;
R 5 is selected from the group consisting of hydroxyl, benzyl, alkoxy, hydroxyalkyl, and cycloalkyl optionally substituted with hydroxyl; and
R 6 and R 7 are each independently selected from the group consisting of hydrogen; an alkyl group; a cycloalkyl group; an alkenyl group; a cycloalkenyl group; benzyl, an alkoxy group; phenyl optionally substituted with an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; an alkyl group substituted with phenyl in which phenyl is optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; phenoxy; and benzyloxy;
with the proviso that:
a) when R 1 is
and R 2 and R 4 are each hydrogen, and
1) when R 3 is hydrogen, then R 6 is not hydrogen or methyl;
2) when R 3 is hydrogen and R 5 is hydroxyl, then R 6 is not hydrogen;
3) when R 3 is tert-butyl and R 5 is hydroxyl, then R 6 is not 4-tert-butyl;
b) when R 1 is
then none of R 2 , R 3 and R 4 is C 1 -C 4 alkyl, the other two of R 2 , R 3 and R 4 being hydrogen;
c) when R 1 is a
then each of R 2 , R 3 , R 4 and R 7 are not hydrogen; and
an antimicrobial effective carrier.
6 . The antimicrobial composition of claim 5 wherein the antimicrobial effective carrier is selected from the group consisting of water, saline, alcohol, glycerin, propylene glycol, mineral oil, petrolatum, and mixtures thereof.
7 . The antimicrobial composition of claim 5 wherein R 1 is
each of R 3 and R 4 are hydrogen, and R 2 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
8 . The antimicrobial composition of claim 5 wherein R 1 is
each of R 2 and R 4 are hydrogen, and R 3 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
9 . The antimicrobial composition of claim 5 wherein R 1 is
each of R 2 and R 3 are hydrogen, and R 4 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
10 . The antimicrobial composition of claim 5 wherein R 1 is
and R 5 is alkoxy.
11 . The antimicrobial composition of claim 10 wherein each of R 3 and R 4 is hydrogen and R 2 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
12 . The antimicrobial composition of claim 10 wherein each of R 2 and R 4 is hydrogen and R 3 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
13 . The antimicrobial composition of claim 10 wherein each of R 2 and R 3 is hydrogen and R 4 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
14 . The antimicrobial composition of claim 5 wherein the antimicrobial effective amount is from about 0.0001 to 10% by weight of the total weight of the antimicrobial composition.
15 . The antimicrobial composition of claim 14 wherein the antimicrobial effective amount is from about 0.001 to 5% by weight.
16 . The antimicrobial composition of claim 5 wherein the antimicrobial compounds of Formula (II) are selected from the group consisting of 2-(2-Hydroxy-4-methylPhenoxy)-5-ethylPhenol, 2-(2-HydroxyPhenoxy)-5-heptylPhenol, 2-(2-HydroxyPhenoxy)-5-octylPhenol, 2-but-2-enyl-6-(2-methoxyphenoxy)phenol, 2-(2-methoxyphenoxy)-6-butylphenol, 2-(2-hydroxyphenoxy)-6-(3-hydroxypropyl)phenol, 6-(2-hydroxypropyl)-2-(2-methoxyphenoxy)phenol, 6-(3-hydroxypropyl)-2-(2-methoxyphenoxy)phenol, 6-(3-hydroxy-1-methylpropyl)-2-(2-hydroxyphenoxy)phenol, 6-(3-hydroxy-1-methylpropyl)-2-(2-methoxyphenoxy)phenol, 2-(2-hydroxyphenoxy)-6-(2-hydroxycyclohexyl)phenol, 2-(2-hydroxyphenoxy)-6-(3-hydroxycyclohexyl)phenol, 2-(2-methoxyphenoxy)-6-prop-2-enylphenol, 2-(2-methoxyphenoxy)-6-(1-methylprop-2-enyl)phenol, 2-(2-methoxyphenoxy)-6-propylphenol, 2-tert-butyl-6-phenylmethoxyphenol, 2-(4-(1-methyl-1-ethylpropyl)-phenylmethoxy)phenol, 2-phenylmethoxy-4-cyclohexylphenol, 2-(2-hydroxy-4-tert-butylphenoxy)-6-propylphenol, 2-(2-hydroxyphenoxy)-5-cyclohexylmethylphenol, 2-(2-hydroxyphenoxy)-6-cyclohexylphenol, 2-(2-methoxyphenoxy)-6-but-2-enylphenol, 2-(2-methoxyphenoxy)-5-phenylmethylphenol.
17 . An oral composition comprising an antimicrobial effective amount of at least one antimicrobial compound of Formula (III):
wherein
R 1 is selected from the group
R 2 and R 3 are each independently selected from the group consisting of hydrogen; an alkyl group; a cycloalkyl group; an alkenyl group; a cycloalkenyl group; a hydroxyalkyl group; a hydroxycycloalkyl group; an alkyl group substituted with phenyl in which phenyl is optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; phenyl optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; and benzyl optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group;
R 4 is selected from the group consisting of hydrogen, an alkyl group, a cycloalkyl group, benzyl, and phenyl;
R 5 is selected from the group consisting of hydroxyl, benzyl, alkoxy, hydroxyalkyl, and cycloalkyl optionally substituted with hydroxyl; and
R 6 and R 7 are each independently selected from the group consisting of hydrogen; an alkyl group; a cycloalkyl group; an alkenyl group; a cycloalkenyl group; benzyl, an alkoxy group; phenyl optionally substituted with an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; an alkyl group substituted with phenyl in which phenyl is optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; phenoxy; and benzyloxy;
with the proviso that
a) when R 1 is
then each of R 2 , R 3 , R 4 , and R 6 is not hydrogen; and
b) when R 1 is
then none of R 2 , R 3 and R 4 is C 1 -C 4 alkyl, the other two of R 2 , R 3 and R 4 being hydrogen; and
an orally acceptable carrier.
18 . The oral composition of claim 17 wherein the orally acceptable carrier is selected from the group consisting of water, saline, alcohol, glycerin, propylene glycol and mixtures thereof.
19 . The oral composition of claim 17 wherein R 1 is
each of R 3 and R 4 are hydrogen, and R 2 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
20 . The oral composition of claim 17 wherein R 1 is
each of R 2 and R 4 are hydrogen, and R 3 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
21 . The oral composition of claim 17 wherein R 1 is
each of R 2 and R 3 are hydrogen, and R 4 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
22 . The oral composition of claim 17 wherein R 1 is
and R 5 is alkoxy.
23 . The oral composition of claim 22 wherein each of R 3 and R 4 is hydrogen and R 2 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
24 . The oral composition of claim 22 wherein each of R 2 and R 4 is hydrogen and R 3 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
25 . The oral composition of claim 22 wherein each of R 2 and R 3 is hydrogen and R 4 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
26 . The oral composition of claim 17 wherein the antimicrobial effective amount is from about 0.0001 to 10% by weight of the total weight of the oral composition.
27 . The oral composition of claim 26 wherein the antimicrobial effective amount is from about 0.001 to 5% by weight.
28 . An oral composition comprising an antimicrobial effective amount of at least one antimicrobial compound of Formula (IV):
wherein
R 1 is selected from the group consisting of
R 2 and R 3 are each independently selected from the
group consisting of hydrogen; an alkyl group; a cycloalkyl group; an alkenyl group; a cycloalkenyl group; a hydroxyalkyl group; a hydroxycycloalkyl group; an alkyl group substituted with phenyl in which phenyl is optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; phenyl optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; and benzyl optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group;
R 4 is selected from the group consisting of hydrogen, an alkyl group, a cycloalkyl group, benzyl, and phenyl;
R 5 is selected from the group consisting of hydroxyl, benzyl, alkoxy, hydroxyalkyl, and cycloalkyl optionally substituted with hydroxyl; and
R 6 and R 7 are each independently selected from the group consisting of hydrogen; an alkyl group; a cycloalkyl group; an alkenyl group; a cycloalkenyl group; benzyl, an alkoxy group; phenyl optionally substituted with an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; an alkyl group substituted with phenyl in which phenyl is optionally substituted with a member selected from the group consisting of an alkyl group, a cycloalkyl group, a hydroxyalkyl group, and a hydroxycycloalkyl group; phenoxy; and benzyloxy;
with the proviso that
when R 1 is
then each of R 2 , R 3 , R 4 , and R 6 is not hydrogen; and an orally acceptable carrier.
29 . The oral composition of claim 28 further comprising at least one essential oil.
30 . The oral composition of claim 29 wherein the essential oil is selected from the group consisting of thymol, menthol, eucalyptol, methyl salicylate, and combinations thereof.
31 . The oral composition of claim 30 , wherein the essential oil comprises:
an amount of from about 0.005 to 0.5% menthol; an amount of from about 0.005 to 0.5% eucalyptol; an amount of from about 0.005 to 0.5% methyl salicytate; and an amount of from about 0.005 to 0.5% thymol.
32 . The oral composition of claim 28 wherein the antimicrobial compounds of Formula (IV) are selected from the group consisting of 2-(2-Hydroxy-4-methylPhenoxy)-5-ethylPhenol, 2-(2-HydroxyPhenoxy)-5-heptylPhenol, 2-(2-HydroxyPhenoxy)-5-octylPhenol, 2-but-2-enyl-6-(2-methoxyphenoxy)phenol, 2-(2-methoxyphenoxy)-6-butylphenol, 2-(2-hydroxyphenoxy)-6-(3-hydroxypropyl)phenol, 6-(2-hydroxypropyl)-2-(2-methoxyphenoxy)phenol, 6-(3-hydroxypropyl)-2-(2-methoxyphenoxy)phenol, 6-(3-hydroxy-1-methylpropyl)-2-(2-hydroxyphenoxy)phenol, 6-(3-hydroxy-1-methylpropyl)-2-(2-methoxyphenoxy)phenol, 2-(2-hydroxyphenoxy)-6-(2-hydroxycyclohexyl)phenol, 2-(2-hydroxyphenoxy)-6-(3-hydroxycyclohexyl)phenol, 2-(2-methoxyphenoxy)-6-prop-2-enylphenol, 2-(2-methoxyphenoxy)-6-(1-methylprop-2-enyl)phenol, 2-(2-methoxyphenoxy)-6-propylphenol, 2-tert-butyl-6-phenylmethoxyphenol, 2-(4-(1-methyl-1-ethylpropyl)-phenylmethoxy)phenol, 2-phenylmethoxy-4-cyclohexylphenol, 2-(2-hydroxy-4-tert-butylphenoxy)-6-propylphenol, 2-(2-hydroxyphenoxy)-5-cyclohexylmethylphenol, 2-(2-hydroxyphenoxy)-6-cyclohexylphenol, 2-(2-methoxyphenoxy)-6-but-2-enylphenol, 2-(2-methoxyphenoxy)-5-phenylmethylphenol.
33 . A method of reducing the presence of microorganisms on a substrate comprising treating the substrate with an effective amount of the antimicrobial composition of claim 5 .
34 . The method of claim 33 wherein the antimicrobial effective carrier is selected from the group consisting of water, saline, alcohol, glycerin, propylene glycol, mineral oil, petrolatum, and mixtures thereof.
35 . The method of claim 33 wherein the antimicrobial effective amount is from about 0.0001 to 10% by weight.
36 . The method of claim 35 wherein the antimicrobial effective amount is from about 0.001 to 5% by weight.
37 . The method of claim 33 wherein the antimicrobial composition is in the form of a member selected from the group consisting of a deodorant, a soap, an ointment, and a cream.
38 . A method of reducing the presence of microorganisms in an oral cavity comprising administering into the oral cavity an effective amount of the oral composition of claim 17 .
39 . The method of claim 38 wherein the orally acceptable carrier is selected from the group consisting of water, saline, alcohol, glycerin, propylene glycol, and mixtures thereof.
40 . The method of claim 38 wherein R 1 is
each of R 3 and R 4 are hydrogen, and R 2 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
41 . The method of claim 40 wherein R 1 is
each of R 2 and R 4 are hydrogen, and R 3 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
42 . The method of claim 40 wherein R 1 is
each of R 2 and R 3 are hydrogen, and R 4 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
43 . The method of claim 40 wherein R 1 is
and R 5 is alkoxy.
44 . The method of claim 43 wherein each of R 3 and R 4 is hydrogen and R 2 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
45 . The method of claim 43 wherein each of R 2 and R 4 is hydrogen and R 3 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
46 . The method of claim 43 wherein each of R 2 and R 3 is hydrogen and R 4 is selected from the group consisting of alkyl, hydroxyalkyl, cycloalkyl, hydroxycycloalkyl, alkenyl, phenyl and benzyl.
47 . The method of claim 38 wherein the effective amount is from about 0.0001 to 10% by weight.
48 . The method of claim 47 wherein the effective amount is from about 0.001 to 5% by weight.
49 . The method of claim 48 wherein the oral composition is in the form of a member selected from the group consisting of a mouthrinse, a dentifrice, a chewing gum, a lozenge, a dispersible oral film, and an oral film forming dentifrice.Join the waitlist — get patent alerts
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