Hydrophilic compounds for optically active devices

Patent metadata

Field	Value
Publication number	US-11111226-B2
Application number	US-202016868607-A
Country	US
Kind code	B2
Filing date	May 7, 2020
Priority date	Aug 21, 2015
Publication date	Sep 7, 2021
Grant date	Sep 7, 2021

Abstract

The present invention relates to novel compounds, particularly to hydrophilic compounds, comprising a photoactive unit, said novel compounds being particularly suitable for ophthalmic devices. The present application also relates to ophthalmic devices comprising such compounds.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
a is 0 or 1;
a′ is 0 or 1;
R 1 , R 2 and R 3 are at each occurrence independently H, F, Cl, Br, I, alkyl having from 1 to 20 carbon atoms, partially or completely halogenated alkyl having from 1 to 20 carbon atoms, aryl or heteroaryl;
one or both of R 4 and R 5 is a group of formula (II)

 and, if only one group of R 4 and R 5 is of formula (II) and a′ is 1, the other of R 4 and R 5 H, F, Cl, Br, I, alkyl having from 1 to 20 carbon atoms, partially or completely halogenated alkyl having from 1 to 20 carbon atoms, aryl, heteroaryl, or R 6 —Sp-[X 1] a —*; or
 one or both of R 4 and R 5 is a group of formula (II) and if only one group of R 4 and R 5 is of formula (II) and a′ is 0, the other of R 4 and R 5 is R 6′ -Sp-[X 1] a —*
R 6′ is a carbyl,

R 6 is a carbyl group for a′=1 and for a′=0 is H;
Sp is selected from the group consisting of alkanediyl, alkenediyl and alkyndiyl, wherein at least one hydrogen has been replaced with OH;
and wherein said alkanediyl, alkenediyl and alkyndiyl groups have 6-12 carbon atoms;
X 1 , X 2 and X 3 are independently of each other 0, S or N—R 17 ;
R 10 , R 11 , R 12 , R 13 and R 14 are at each occurrence independently of each other H, F, Cl, Br, I, R 6′ -Sp-[x1]a-* and R 15 , wherein any two adjacent groups of R 10 , R 11 , R 12 , R 13 or R 14 that are R 15 may also form a ring system;
R 15 is at each occurrence independently alkyl having from 1 to 20 carbon atoms, partially or completely halogenated alkyl having from 1 to 20 carbon atoms, alkoxy having from 1 to 20 carbon atoms, partially or completely halogenated alkoxy having from 1 to 20 carbon atoms, thioalkyl having from 1 to 20 carbon atoms, or partially or completely halogenated thioalkyl having from 1 to 20 carbon atoms; and
R 17 is at each occurrence independently H, F, Cl, Br, I, alkyl having from 1 to 20 carbon atoms, partially or completely halogenated alkyl having from 1 to 20 carbon atoms, aryl or heteroaryl,

provided that the compound of formula (I) comprises one group R 6 —Sp-[x 1 ] a -*
wherein* each indicate the location of the linkage of the group containing the * to the rest of the compound.

2. A compound according to claim 1 , said compound being of formula (I′)

wherein
one or both of R 4 and R 5 is a group of formula (II)

and, if only one group of R 4 and R 5 is of formula (II), the other of R 4 and R 5 is H, F, Cl, Br, I, alkyl having from 1 to 20 carbon atoms, partially or completely halogenated alkyl having from 1 to 20 carbon atoms, aryl or heteroaryl;
R 6 is a carbyl group; and
R 10 , R 11 , R 12 , R 13 and R 14 are at each occurrence independently of each other H, F, Cl, Br, I, or R 15 , wherein any two adjacent groups of R 10 , R 11 , R 12 , R 13 , R 14 that are R 15 may also form a ring system.

3. A compound according to claim 1 , wherein R 1 , R 2 and R 3 are H.

4. A compound according to claim 1 , wherein R 4 is H and R 5 is a group of formula (II).

5. A compound according to claim 1 , wherein R 10 , R 11 , R 12 , R 13 and R 14 are H.

6. A compound according to claim 1 , wherein Sp is of formula (III)
—[C(R 7 )(R 8 )]b-  (III)

wherein b is 6-12;
R 7 and R 8 are independently of each other H or OH, provided that at least one of the R 7 and R 8 in formula III is OH; and
wherein two neighboring groups C(R 7 )(R 8 ) may be replaced by an alkenediyl or two neighboring groups C(R 7 )(R 8 ) may be replaced by an alkyndiyl.

7. A compound according to claim 1 , wherein X 1 is O.

8. A compound according to claim 1 , wherein X 2 is O or S.

9. A compound according claim 1 , wherein X 3 is O or N—R 17 .

10. A compound according claim 1 , wherein such compound is an oligomer or polymer.

11. A compound according to claim 1 , wherein R 6 is a group of formula (IV-B) when a′ is 1

wherein X 4 is O, S, C(═O), C(═O)O or N—R 17 ;
c is 0 or 1; and
R 20 , R 21 , and R 22 are at each occurrence independently of each other H, F, alkyl having from 1 to 20 carbon atoms, partially or completely halogenated alkyl having from 1 to 20 carbon atoms, aryl or heteroaryl.

12. A compound according to claim 1 , wherein said compound comprises at least one unit M 1 the following formulae (I-B′), (I-B″-1) or (I-B″-2)

said at least one unit M 1 being, if there are two or more, at each occurrence the same or different, wherein X 4 is at each occurrence independently O, S, C(═O), C(═O)O—or N—R 17 ;
c is at each occurrence 0 or 1; and
R 20 , R 21 , and R 22 are at each occurrence independently of each other H, F, alkyl
having from 1 to 20 carbon atoms, partially or completely halogenated alkyl
having from 1 to 20 carbon atoms, aryl or heteroaryl
each indicate a linkage to an adjacent repeating unit of the oligomer or polymer.

13. A compound according to claim 12 , said compound further comprising at least one unit M 2 , which at each occurrence is independently ethylene, propylene, an acrylate, a methacrylate or a styrene.

14. A compound according to claim 13 , said compound comprising units M 1 and M 2 in a ratio m 1 :m 2 of from 0.01 to 100.

15. A compound according to claim 1 , wherein R 6 comprises an olefinically unsaturated group.

16. A compound according to claim 1 , wherein R 6 is a group of formula (IV-A) when a′ is 1

wherein
c is 0 or 1;
* each indicate the location of the linkage of the group containing the * to the rest of the compound of formula (II);
X 4 is O, S, C(═O), C(═O)O—or N—R 17 ; and
R 20 , R 21 , and R 22 are at each occurrence independently of each other H, F, alkyl
having from 1 to 20 carbon atoms, partially or completely halogenated alkyl
having from 1 to 20 carbon atoms, aryl or heteroaryl.

17. A compound according to claim 1 , wherein said compound is of formulae (I-A′), (I-A ″′ -1) or (I-A″′-2)

wherein
X 4 is O, S, C(═O), C(═O)O or N—R 17 ;
c is 0 or 1; and
R 20 , R 21 , and R 22 are at each occurrence independently of each other H, F, alkyl
having from 1 to 20 carbon atoms, partially or completely halogenated alkyl
having from 1 to 20 carbon atoms, aryl or heteroaryl.

18. A composition comprising the compound of claim 1 .

19. An article comprising the composition of claim 18 .

20. An article according to claim 19 , wherein said article is an optically active article.

21. An articl

Assignees

• Merck Patent Gmbh

Inventors

• Dobelmann-Mara Lars
• Riedmueller Stefan
• Schraub Martin

Classifications

• C07D335/06

  Benzothiopyrans; Hydrogenated benzothiopyrans · CPC title

• A61L27/50

  Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials} · CPC title

• C07D311/16 Primary

  substituted in position 7 · CPC title

• A61L2430/16

  for reconstruction of eye parts, e.g. intraocular lens, cornea · CPC title

• C07D311/42

  with oxygen or sulfur atoms in positions 2 and 4 · CPC title