Photostable compounds, absorbing compounds and uses thereof

Patent metadata

Field	Value
Publication number	US-10315994-B2
Application number	US-201615518743-A
Country	US
Kind code	B2
Filing date	Nov 28, 2016
Priority date	Nov 27, 2015
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

The present invention describes compounds and uses thereof in applications relating to absorption of electromagnetic energy. Preferred compounds are double bond-containing cyclic compounds capable of absorbing electromagnetic radiation energy and having improved photostability due to the presence and location of one or more fluorine groups in relation to the double bond of the ring.

First claim

The invention claimed is:

1. A compound of formula II, or a salt thereof:

wherein, the dotted line may be a bond;
X is one or two carbon atoms forming part of the ring structure;
R 1 and R 2 are independently selected from hydrogen, substituted C 1 to C 6 alkyl, or unsubstituted C 1 to C 6 alkyl;
W is O;
R a , R b , and R 3 , when present, are independently selected from hydrogen, halo, C 1 to C 20 alkyl, C 2 to C 20 alkenyl, C 2 to C 20 alkynyl, aryl, heteroaryl, aroyl, C 2 to C 12 alkanone, C 5 to C 7 cycloalkyl, C 4 to C 7 cycloalkanone, C 5 to C 7 cycloalkenyl, C 2 to C 12 alkanoyl, C 2 to C 12 alkacanoyloxy, C 2 to C 12 alkoxycarbonyl, C 2 to C 12 carbamoyl, C 2 to C 12 carboxyl, haloalkyl, N-alkyl, N-aryl, N-heterocyclyl or heterocyclic, all of which groups may be substituted or unsubstituted, or R b and R 3 may together form an alkene, an alkyne, a phenyl ring or a heteroaryl ring each of which is optionally substituted with at least one halogen or halogen-containing group, and wherein at least one of R a , R b and R 3 comprises a halogen;
R 4 is hydrogen;
R 5 is selected from C 1 to C 12 alkyl, C 2 to C 12 alkenyl, C 2 to C 12 alkynyl, aryl, amine, heteroaryl, heterocyclyl, C 5 to C 7 cycloalkyl, C 5 to C 7 cycloalkenyl, C 2 to C 9 alkanoyl, C 1 to C 12 alkanoyloxy or carbamoyl all of which groups may be substituted or unsubstituted;
R 6 is hydrogen; and
R 18 and R 19 are hydrogen,
with the proviso that when R 1 and R 2 are methyl, R a , R b , and R 3 are all fluorine, W is O and R 4 is hydrogen then R 5 is not any of 4-dimethylaminophenyl, 4-methoxyphenyl, 4-methylphenyl, 4-tert-butylphenyl, isopropyl or 1-naphthyl.

2. The compound of claim 1 wherein at least one of R a and R b are fluorine or wherein R b and R 3 combine to form a 6-membered ring with one or more fluorine substituents on the ring.

3. The compound of claim 1 wherein R 3 is selected from halo, C 1 to C 9 alkyl, C 2 to C 9 alkenyl, C 5 -C 6 aryl, C 5 -C 6 heteroaryl, C 2 to C 12 alkanone, C 5 -C 6 cycloalkyl, C 5 -C 6 cycloalkanone, C 5 -C 6 cycloalkenyl, C 2 to C 9 alkanoyl, C 2 to C 9 alkanoyloxy, C 2 to C 9 alkoxycarbonyl, C 2 to C 9 carbamoyl, C 2 to C 9 carboxyl, haloalkyl, N-alkyl, N-aryl, N-heterocyclyl or C 5 -C 6 heterocyclic, all of which groups may be substituted or unsubstituted.

4. The compound of claim 1 wherein R 3 is C 1 to C 6 perfluoroalkyl.

5. The compound of claim 1 wherein R a , R b and R 3 and the carbon to which they are attached, together form a moiety selected from the group consisting of:

wherein, R 1 ′ and R 2 ′, may be selected from any group as defined for R 1 and R 2 , respectively, and R 12 may be selected from hydrogen, C 1 -C 6 alkyl or C 1 -C 6 alkoxy.

6. The compound of claim 1 wherein R 5 is selected from C 1 to C 6 alkyl, C 2 to C 6 alkenyl, phenyl, aryl, naphthyl, C 6 cycloalkyl, C 2 to C 6 alkanoyl or C 2 to C 6 alkanoyloxy all of which groups may be substituted or unsubstituted.

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

wherein, a dotted line may be a bond, n is from 0 to 5, R 1 ′, R 2 ′, R a ′, R b ′ and R 3 ′ may be selected from any group as defined in any one of the preceding claims for R 1 , R 2 , R a , R b and R 3 , respectively, and each incidence of R 12 and R 13 is independently selected from hydrogen, C 1 -C 6 alkyl and C 1 -C 6 alkoxy.

8. The compound of claim 1 wherein the compound is selected from:

9. The compound of claim 1 , wherein the dotted line is not a bond.

10. The compound of claim 1 , wherein X is one carbon.

11. A composition comprising a compound of claim 1 , or a salt thereof, and a suitable carrier.

12. 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.

Assignees

• Commw Scient Ind Res Org
• Commomwealth Scient And Industrial Research Organization

Inventors

• Ryan John
• York Mark

Classifications

• C07D211/82

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• A61K8/4926

  having six membered rings · CPC title

• A61Q17/04

  Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations · CPC title

• C09D5/32

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

• C07D211/70 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title