Compounds for optically active devices

Patent metadata

Field	Value
Publication number	US-10457658-B2
Application number	US-201615753192-A
Country	US
Kind code	B2
Filing date	Aug 3, 2016
Priority date	Aug 21, 2015
Publication date	Oct 29, 2019
Grant date	Oct 29, 2019

Abstract

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

First claim

The invention claimed is:

1. An optically active intraocular lens article, which comprises 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 selected from the group consisting of 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 and heteroaryl;
one of R 4 and R 5 is a group of formula (II)

and the other of R 4 and R 5 is selected from the group consisting of 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, and R 6 -Sp-[X 1 ] a *;

* each indicate the location of the linkage of the group containing the * to the rest of the compound,
R 6 is a carbyl group for a′=1 and for a′=0 is selected from the group consisting of 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 and heteroaryl;
Sp is selected from the group consisting of alkanediyl, alkenediyl and alkyndiyl having at least 10 carbon atoms and at most 20 carbon atoms;
X 1 and X 2 are independently of each other selected from the group consisting of O, S and N—R 17 ;
X 3 is O or S;
R 10 , R 11 , R 12 , R 13 and R 14 are at each occurrence independently of each other selected from the group consisting of H, F, Cl, Br, I, R 6 -Sp-[X 1 ] a *, alkyl having from 1 to 20 carbon atoms, partially or completely halogenated alkyl having from 1 to 20 carbon atoms, aryl and heteroaryl, provided that at least one of R 10 , R 11 , R 12 , R 13 and R 14 is R 15 ;
R 15 is at each occurrence independently selected from the group consisting of 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, and partially or completely halogenated thioalkyl having from 1 to 20 carbon atoms; and
R 17 is at each occurrence independently selected from the group consisting of 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 and heteroaryl,
provided that the compound of formula (I) comprises one group R 6 -Sp-[X 1 ] a -*.

2. The intraocular lens article according to claim 1 , wherein said compound of formula (I) is a compound of formula (I′)

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

and the other of R 4 and R 5 is selected from the group consisting of 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 and 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 selected from the group consisting of 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 and heteroaryl, provided that at least one of R 10 , R 11 , R 12 , R 13 , and R 14 is R 15 , and wherein any two groups of R 10 , R 11 , R 12 , R 13 and R 14 that are R 15 may also form a ring system.

3. The intraocular lens article according to claim 1 , wherein said compound of formula (I) is a compound of formula (I″)

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

and the other of R 4 and R 5 is selected from the group consisting of 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 and heteroaryl;

R 6 is selected from the group consisting of 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 and heteroaryl; and
one of R 10 , R 11 , R 12 , R 13 and R 14 is R 6 -Sp-[X 1 ] a *, with the others at each occurrence independently of each other selected from the group consisting of 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 and heteroaryl, provided that at least one of R 10 , R 11 , R 12 , R 13 and R 14 is R 15 , wherein any two adjacent groups of R 10 , R 11 , R 12 , R 13 and R 14 that are R 15 may also form a ring system.

4. The intraocular lens article according to claim 1 , wherein said compound of formula (I) is a compound of formula (I″)

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

and the other of R 4 and R 5 is R 6 -Sp-[X 1 ] a —*;

R 6 is selected from the group consisting of 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 and heteroaryl; and
R 10 , R 11 , R 12 , R 13 and R 14 are at each occurrence independently of each other selected from the group consisting of 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 and heteroaryl, provided that at least one of R 10 , R 11 , R 12 , R 13 and R 14 is R 15 , wherein any two adjacent groups of R 10 , R 11 , R 12 , R 13 and R 14 that are R 15 may also form a ring system.

5. The intraocular lens article according to claim 1 , wherein, in the compound of formula (I), R 1 , R 2 and R 3 are H.

6. The intraocular lens article according to claim 1 , wherein, in the compound of formula (I), R 4 is H and R 5 is a group of formula (II).

7. The intraocular lens article according to claim 1 , wherein, in the compound of formula (I), those of R 10 , R 11 , R 12 , R 13 and R 14 that are not R 15 are H.

8. The intraocular lens article according to claim 1 , wherein, in the compound of formula (I), Sp is selected from the group consisting of alkanediyl, alkenediyl and alkyndiyl, wherein at least one hydrogen has been replaced with R 16 , with R 16 being selected from the group consisting of OH, alkyl having from 1 to 10 carbon atoms, partially or completely halogenated alkyl having from 1 to 10 carbon atoms, alkoxy having from 1 to 10 carbon atoms, and partially or completely halogenated alkoxy having from 1 to 10 carbon atoms.

9. The intraocular lens article according to claim 1 , wherein, in the compound of formula (I), Sp is of formula (III)
—[C(R 7 )(R 8 )] b —  (III)

wherein
b is at least 1; and
R 7 and R 8 are independently of each other H or R 16 , provided that at l

Assignees

• Merck Patent Gmbh

Inventors

• Dobelmann-Mara Lars
• Riedmueller Stefan
• Schraub Martin

Classifications

• C08F20/38

  Esters containing sulfur · 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

• G02B1/041

  Lenses · CPC title

• C08F20/40

  Esters of unsaturated alcohols {, e.g. allyl (meth)acrylate} · CPC title