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US 2016/0244409 A1Published application
UV Absorbing Compounds, Compositions Comprising Same and Uses Thereof
AssigneeCoral Sunscreen Pty Ltd
InventorsMark YORK, John RYAN, Gregory Paul SAVAGE, Adam Gerhard MEYER, Karen JARVIS
Life of this patent
Estimating the term…
Abstract
There is provided a range of novel compounds which have been demonstrated to have useful UV absorbing properties. These compounds will find use in a range of applications such as active components in sunscreen formulations, paints, plastics, fabrics, glass and UV protective coatings.
Claims22
1:
- A compound of formula I, or a salt thereof:
- wherein, X, if present, is one or two carbon atoms forming part of the ring structure;
- R1 and R2 are independently selected from the group consisting of C1 to C10 alkyl, C1 to C10 alkenyl and C1 to C10 alkoxy, each of which groups may be substituted or unsubstituted;
- R3 is selected from the group consisting of substituted or unsubstituted C1 to C6 alkenyl, and
- wherein W is sulphur or oxygen and R7 is selected from the group consisting of C1 to C20 alkyl, C2 to C20 alkenyl, C2 to C20 alkynyl, aryl, heteroaryl, aroyl, C2 to C20 alkanone, C5 to C7 cycloalkyl, C4 to C7 cycloalkanone, C5 to C7 cycloalkenyl, C2 to C20 alkanoyl, C2 to C20 alkanoyloxy, C2 to C20 alkoxycarbonyl, C2 to C20 carbamoyl, C2 to C20 carboxyl, haloalkyl, N-alkyl, N-aryl, N-heterocyclyl, N—SO2—R20 and heterocyclic all of which groups may be substituted or unsubstituted and wherein R20 is selected from the group consisting of C1 to C6 alkyl and phenyl each of which may be substituted or unsubstituted with the proviso that R3 comprises a carbon atom directly attached to the ring structure in formula I and that carbon is double bonded to another atom;
- R4 is selected from the group consisting of hydrogen, C1 to C12 alkyl, C2 to C12 alkenyl, aryl, heteroaryl, C5 to C7 cycloalkyl, C5 to C7 cycloalkenyl, C1 to C12 alkanoyl, C1 to C12 alkanoyloxy, C1 to C12 carboalkoxy and C1 to C12 alkanone all of which groups may be substituted or unsubstituted;
- R5 is selected from the group consisting of C1 to C12 alkyl, C2 to C12 alkenyl, C2 to C12 alkynyl, aryl, heteroaryl, C5 to C9 cycloalkyl, C5 to C7 cycloalkenyl, C2 to C9 alkanoyl, C2 to C9 alkanoyloxy and carbamoyl all of which groups may be substituted or unsubstituted;
- R6 is selected from the group consisting of hydrogen, oxo, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C2 to C6 alkenyl and substituted or unsubstituted C2 to C6 alkanoyl;
- and
- R18 and R19 are independently selected from the group consisting of hydrogen, C1 to C6 alkyl, C1 to C6 alkenyl and C1 to C6 alkoxy, each of which groups may be substituted or unsubstituted,
- with the proviso that when R5 is alkyl or cycloalkyl and R4 is hydrogen then R7 is not an unsubstituted alkyl chain, an ester or an ether;
- and
- when R5 is unsubstituted benzyl then R7 is not hexyl;
- and
- wherein,
- the compound is not
13 more elements
2:
- The compound of claim 1 wherein the atom which is double bonded to the carbon attached directly to the ring is selected from the group consisting of a carbon atom, an oxygen atom, a nitrogen atom and a sulphur atom.
3:
- The compound of claim 1 wherein X is one carbon atom;
- R1 and R2 are independently selected from the group consisting of C1 to C6 alkyl, C1 to C6 alkenyl and C1 to C6 alkoxy, each of which groups may be substituted or unsubstituted;
- R3 is selected from the group consisting of substituted or unsubstituted C1 to C6 alkenyl and
- wherein W is sulphur or oxygen, preferably oxygen, and R7 is selected from the group consisting of C1 to C6 alkyl, trihaloalkyl, C2 to C6 alkenyl, C2 to C6 alkynyl, aryl, aroyl, C2 to C12 alkanone, C2 to C9 alkanoyl, C2 to C9 alkanoyloxy, C2 to C9 alkoxycarbonyl, C2 to C6 carboxyl, C1 to C6 haloalkyl, C4 to C7 cycloalkanone, N— C1 to C6 alkyl, N— C5 to C7 aryl, N— C5 to C7 heterocycly, N—SO2—R20 and C5 or C6 heterocyclic all of which groups may be substituted or unsubstituted and wherein R20 is selected from the group consisting of C1 to C6 alkyl and phenyl each of which may be substituted or unsubstituted with the proviso that R3 comprises a carbon atom directly attached to the ring structure in formula I and that carbon is double bonded to another atom;
- R4 is selected from the group consisting of hydrogen, C1 to C6 alkyl, C2 to C6 alkenyl, phenyl, heteroaryl, C6 cycloalkyl, C1 to C12 alkanoyl, C1 to C9 alkanoyloxy, C1 to C9 carboalkoxy and C1 to C6 alkanone all of which groups may be substituted or unsubstituted;
- R5 is selected from the group consisting of C1 to C6 alkyl, C2 to C6 alkenyl, phenyl, naphthyl, C6 cycloalkyl, C2 to C6 alkanoyl and C2 to C6 alkanoyloxy all of which groups may be substituted or unsubstituted;
- R6 is selected from the group consisting of hydrogen, oxo and substituted or unsubstituted C1 to C6 alkyl;
- and
- R18 and R19 are independently selected from the group consisting of hydrogen and C1 to C6 alkyl, each of which groups may be substituted or unsubstituted.
6 more elements
4:
- The compound of claim 1 wherein X is one carbon atom;
- R1 and R2 are independently selected from C1 to C4 alkyl substituted or unsubstituted;
- R3 is selected from the group consisting of arylsulfonyl and
- wherein W is sulphur or oxygen, preferably oxygen, and R7 is selected from the group consisting of C1 to C4 alkyl, trifluoro substituted C1 to C4 alkyl, C2 to C6 alkenyl, phenyl, phenylheterocyclic, alkylbenzoyl, phenyl substituted alkanone, C2 to C9 alkanoyloxy, C2 to C9 alkoxycarbonyl, C2 to C4 carboxyl, C5 or C6 heterocyclic, N— C1 to C6 alkyl, N— C6 aryl, N—SO2—R20, POSS substituted alkanoyloxy and POSS substituted carboalkoxy all of which groups may be substituted or unsubstituted and wherein R20 is selected from the group consisting of C1 to C6 alkyl and phenyl each of which may be substituted or unsubstituted with the proviso that R3 comprises a carbon atom directly attached to the ring structure in formula I and that carbon is double bonded to another atom;
- R4 is selected from the group consisting of hydrogen, C1 to C6 alkyl, C2 to C6 alkenyl, phenyl, C6 cycloalkyl, C1 to C12 alkanoyl and C1 to C12 alkanoyloxy all of which groups may be substituted or unsubstituted;
- R5 is selected from the group consisting of C1 to C6 alkyl, phenyl, naphtyl and C6 cycloalkyl all of which groups may be substituted or unsubstituted;
- R6 is hydrogen or oxo;
- and
- R16 and R19 are hydrogen.
6 more elements
5:
- The compound of claim 1 wherein X is one carbon, R1 and R2 are methyl, ethyl or propyl;
- R3 is selected from the group consisting of benzenesulfonyl and
- wherein W is sulphur or oxygen, preferably oxygen, and R7 is selected from the group consisting of
- wherein * represents the carbon atom which is attached to the carbonyl carbon and with the proviso that R3 comprises a carbon atom directly attached to the ring structure in formula I and that carbon is double bonded to another atom;
- R4 is selected from the group consisting of hydrogen, phenyl, butan-2-one and but-1-ene-2-yl propionate;
- R5 is selected from the group consisting of ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, phenyl and phenyl substituted with C1 to C3 alkoxy;
- R6 is hydrogen or oxo;
- and
- R18 and R19 are hydrogen.
6 more elements
6:
- The compound of claim 1 wherein X is one carbon;
- R1 and R2 are independently selected from the group consisting of methyl, ethyl, propyl and butyl;
- R4, R6, R18 and R19 are hydrogen;
- R3 is selected from the group consisting of benzenesulfonyl and
- wherein W is sulphur or oxygen, preferably oxygen, and R7 is selected from the group consisting of
- wherein * represents the carbon atom which is attached to the carbonyl carbon and with the proviso that R3 comprises a carbon atom directly attached to the ring structure in formula I and that carbon is double bonded to another atom;
- and
- R5 is selected from the group consisting of
5 more elements
7:
- The compound of claim 1 wherein R5 is directly attached to the nitrogen of the ring via a tertiary carbon.
8:
- The compound of claim 7 wherein when R5 is alkyl it is tert-butyl.
9:
- The compound of claim 1 wherein R1 and R2 are independently selected from the group consisting of C1 to C10 alkyl, C1 to C10 alkenyl and C1 to C10 alkoxy, each of which groups may be substituted with a group selected from alkyl, alkenyl, heteroaryl, heterocyclyl, alkynyl, aroyl, alkanone, cycloalkyl, cycloalkanone, cycloalkenyl, alkanoyl, alkanoyloxy, alkoxycarbonyl, carbamoyl, carboxyl, haloalkyl, N-alkyl, N-aryl and N-heterocyclyl.
10:
- The compound of claim 1 wherein R6 is selected from the group consisting of hydrogen, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C2 to C6 alkenyl and substituted or unsubstituted C2 to C6 alkanoyl.
11:
- The compound of claim 1 wherein X is 1 or two carbon atoms forming part of the ring structure.
12:
- The compound of claim 1 wherein the compound is a compound of formula IIa or IIb:
- wherein R1, R2 and R5 are as described in claim 1;
- Y, when present, is selected from nitrogen, N-alkyl, C6, C7, C8, C9, C10, C11 or C12 alkyl optionally substituted with oxo, hydroxyl, alkoxy and halo and may be oxygen linked to the ring;
- R8, when present, may be selected from the group consisting of C1 to C6 alkyl, substituted or unsubstituted, aryl, alkoxy, halo and amino.
1 more element
13:
- The compound of claim 12 wherein the compound is a compound of formula IIb and Y is selected from C8, C9, C10, C11 or C12 alkyl optionally substituted with oxo, hydroxyl, alkoxy and halo.
14:
- The compound of claim 13 wherein Y is C9 alkyl substituted with oxo.
15:
- The compound of claim 14 wherein R5 is t-butyl.
16:
- The compound of claim 1 wherein the compound is selected from the group consisting of:
17:
- A composition comprising a compound of claim 1, or a salt thereof, and a suitable carrier.
18:
- The composition of claim 17, wherein the composition is selected from the group consisting of a sunscreen composition, a coating composition and a glass or polymeric film-forming composition.
19-21:
- (canceled)
22:
- A method of protecting a surface or tissue from UV rays including the step of applying a compound of claim 1, or a salt thereof, to the surface or tissue.
23:
- The method of claim 22 wherein the surface is a surface of a fabric, clothing material, plastic, timber, masonry and glass.
24:
- The method of claim 22 wherein the tissue is the skin of a mammal.