Enamine compounds for absorbance of electromagnetic energy

Patent metadata

Field	Value
Publication number	US-11512042-B2
Application number	US-201615518748-A
Country	US
Kind code	B2
Filing date	Dec 23, 2016
Priority date	Dec 23, 2015
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

The present invention describes compounds and uses thereof in applications relating to absorption of electromagnetic energy. Preferred compounds are double bond-containing compounds capable of absorbing electromagnetic radiation energy and having improved properties.

First claim

The invention claimed is:

1. A compound of formula I, or a salt or a cis/trans isomer thereof:

wherein:
R 1 is phenyl, which may be substituted or unsubstituted;
R 2 is hydrogen;
R 3 and R 4 together form a 5-membered nitrogen heterocycle fused with a benzene ring, each of which may themselves be substituted or unsubstituted; and
R 5 is selected from C 1 to C 20 haloalkyl, C 1 to C 20 haloalkenyl, a fluorine-containing group, C 1 to C 20 secondary or tertiary alkyl wherein secondary and tertiary are defined at the carbon attached to the carbonyl carbon of formula I, C 2 to C 20 alkenyl, ester, amide, C 1 to C 20 alkanoyl, C 1 to C 20 alkenoyl, aryl, C 5 to C 7 cycloalkenyl, or heterocyclic, each of which groups may be substituted or unsubstituted.

2. The compound of claim 1 , wherein R 3 and R 4 together form a pyrrolidine fused with a benzene ring, each of which may themselves be substituted or unsubstituted.

3. The compound of claim 1 , wherein R 3 and R 4 together form a cyclic structure which includes the nitrogen atom to which they are attached, said cyclic structure being selected from the group consisting of:

wherein, the asterisk indicates the enamine nitrogen atom to which R 3 and R 4 are directly attached; and
R 7 and R 8 are selected from hydrogen, F, Br, Cl, C 1 to C 20 alkyl, C 1 to C 6 fluoroalkyl, nitro, C 1 to C 6 alkoxy, —C(O)O—C 1 to C 9 alkyl, —C(O)O—C 1 to C 4 alkyl-carbamate, carboxymethyl, carboxyethyl, a divalent presentation of another compound of formula I, —C(O)O-PEG or —C(O)O-PDMS, each of which may be optionally substituted.

4. The compound of claim 1 , wherein R 5 is selected from C 1 to C 6 fluoroalkyl, C 2 to C 6 fluoroalkenyl, C 5 or C 6 fluoro aryl, C 1 to C 6 perfluoroalkyl, C 1 to C 6 secondary or tertiary alkyl, C 2 to C 9 alkenyl, C 1 to C 9 alkanoyl, C 1 to C 6 cyanoalkyl, phenyl, C 1 to C 9 ester, C 1 to C 9 amide, and 5- to 7-membered heterocyclic, all of which groups may be substituted or unsubstituted.

5. The compound of claim 1 , wherein R 5 is selected from the group consisting of:

6. A compound of claim 1 of formula II, or a salt or a cis/trans isomer thereof:

wherein:
R 1 is phenyl, which is substituted or unsubstituted;
R 3 and R 4 together form a 5-membered nitrogen heterocycle fused with a benzene ring, each of which may themselves be substituted or unsubstituted;
Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are independently selected from a nitrogen or a carbon atom; and
each incidence of R 6 is independently selected from hydrogen, hydroxyl, halo, nitro, cyano, C 1 to C 12 alkyl, C 1 to C 12 alcohol, C 2 to C 12 alkenyl, C 1 to C 12 alkoxy, alkoxysilane, C 1 to C 6 amide, sulphonamide, or C 1 to C 12 haloalkyl, each of which may be substituted or unsubstituted.

7. The compound of claim 6 wherein the compound is a compound of formula IIa, or a salt or a cis/trans isomer thereof:

8. A compound of claim 1 of formula VI, or a salt or a cis/trans isomer thereof:

wherein:
R 3 and R 4 together form a 5-membered nitrogen heterocycle fused with a benzene ring, each of which may themselves be substituted or unsubstituted; and
R 17 , R 18 and R 19 are independently selected from methyl, ethyl or propyl; and
each incidence of R 16 is independently selected from hydrogen, hydroxyl, halo, nitro, cyano, C 1 to C 12 alkyl, C 1 to C 12 alcohol, C 2 to C 12 alkenyl, C 1 to C 12 alkoxy, sulphonamide, or C 1 to C 12 haloalkyl, each of which may be substituted or unsubstituted.

9. The compound of claim 8 , wherein R 16 is hydrogen and R 3 and R 4 together form an optionally substituted indoline ring system.

10. A composition comprising a compound of claim 1 , or a salt or a cis/trans isomer thereof, and a suitable carrier.

11. A method of protecting a surface or tissue from UV rays including the step of applying a compound of claim 1 , or a salt or a cis/trans isomer thereof, to the surface or tissue.

12. The method of claim 11 wherein the surface is selected from a surface of a fabric, clothing material, lens, plastic, timber, masonry or glass, or the tissue is the skin of a mammal.

13. A compound of formula I, or a salt or cis/trans thereof:

wherein, R 1 is phenyl, which may be substituted or unsubstituted;
R 2 is hydrogen;
R 3 and R 4 together form a 5-membered nitrogen heterocycle fused with a benzene ring, each of which may themselves be substituted or unsubstituted;
R 5 is selected from the group consisting of C 1 to C 20 haloalkyl, C 1 to C 20 haloalkenyl, a fluorine-containing group, C 1 to C 20 alkyl, C 2 to C 20 alkenyl, ester, amide, C 1 to C 20 alkanoyl, C 1 to C 20 alkenoyl, aryl, C 5 to C 7 cycloalkenyl, and heterocyclic, each of which groups may be substituted or unsubstituted, and
wherein substituted in the above definitions of R 1 , R 3 , R 4 and R 5 includes substitution with one or more substituents selected from the group consisting of alkyl, alkenyl, alkylalkanoate, aryl, alkylaryl, heteroaryl, heterocyclyl, alkynyl, aroyl, alkanone, cycloalkyl, cycloalkaneone, cycloalkenyl, alkanoyl, alkanoyloxy, alkoxycarbonyl, carbamoyl, carboxyl, halo, cyano, nitro, haloalkyl, N-alkyl, N-aryl and N-heterocyclyl, wherein each of these substituents may themselves be substituted with the same or different substituents.

14. The compound of claim 13 , wherein R 3 and R 4 together form a pyrrolidine fused with benzene ring, which may each be substituted or unsubstituted.

15. The compound of claim 13 , wherein R 3 and R 4 together form a substituted or unsubstituted indoline group.

16. The compound of claim 13 , wherein R 5 is selected from the group consisting of C 1 to C 12 haloalkyl, C 2 to C 12 haloalkenyl, C 5 or C 6 aryl, C 1 to C 12 perhaloalkyl, C 1 to C 12 alkyl, C 1 to C 12 alkenyl, C 1 to C 12 alkanoyl, phenyl, ester, amide, and 5-to 7-membered heterocyclic, all of which groups may be substituted or unsubstituted.

17. The compound of claim 1 , wherein the compound is selected from the group consisting of:

Assignees

• Commw Scient Ind Res Org

Inventors

• York Mark
• Ryan John

Classifications

• C09D5/32

  Radiation-absorbing paints {(protection against X-, gamma- or corpuscular radiation G21F)} · CPC title

• C08K5/3435

  Piperidines · CPC title

• A61K8/4926

  having six membered rings · CPC title

• C07C255/58

  containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton · CPC title

• C07D209/08

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring · CPC title