Hydrophilic compounds for optically active devices

Patent metadata

Field	Value
Publication number	US-10723713-B2
Application number	US-201615753195-A
Country	US
Kind code	B2
Filing date	Aug 3, 2016
Priority date	Aug 21, 2015
Publication date	Jul 28, 2020
Grant date	Jul 28, 2020

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
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), 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 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;
a is 0 or 1;
Sp is alkanediyl, alkenediyl or alkyndiyl, wherein at least one hydrogen has been replaced with OH;
X 1 , X 2 and X 3 are independently of each other O, S or N—R 17 ;
R 15 is at each occurrence independently an 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;
R 17 is at each occurrence independently selected from 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 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 are H, F, Cl, Br, I, or 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;
R 6 is a carbyl group, and
* each indicate the location of the linkage of the group containing the * to the rest of the compound.

2. A compound of formula (I″)

wherein
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 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 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;
a is 0 or 1;
Sp is an alkanediyl, alkenediyl or alkyndiyl, wherein at least one hydrogen has been replaced with OH;
X 1 , X 2 and X 3 are independently of each other are O, S or N—R 17 ;
R 15 is at each occurrence independently selected from 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;
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;
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 and R 14 that are R 15 may also form a ring system;
R 6 is a carbyl group and
* each indicate the location of the linkage of the group containing the * to the rest of the compound.

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 2 , 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 at least 1;
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 present is OH; and
wherein if b is at least two, two neighboring groups C(R 7 )(R 8 ) may be replaced by an alkenediyl or wherein if b is at least three, 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 to claim 1 , wherein X 3 is O or N—R 17 .

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

11. A compound according to claim 10 , wherein R 6 is a polymerized group of formula (IV-B)

Wherein
the * adjacent to the [X 4 ] c indicates the location of the linkage of the group containing the * to the remainder of the following partial structure of formula (II) and the other two * each indicate a linkage to an adjacent repeating unit of the oligomer or polymer,

X 4 is selected from the group consisting of O, S, C(═O), C(═O)O and 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 11 , wherein said compound comprises at least one unit M 1 selected from formulae (I-B″-1), or (I-B″-2),

wherein one of R 10 , R 11 , R 12 , R 13 and R 14 is a group of formula R 6 —Sp-[X 1 ] a —* and R 6 is a group of formula (IV-B);

wherein one of R 10 , R 11 , R 12 , R 13 and R 14 is a group of formula R 6 —Sp-[X 1 ] a —* and R 6 is a group of formula (IVB);
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; and
* 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 accord

Assignees

• Merck Patent Gmbh

Inventors

• Dobelmann-Mara Lars
• Riedmueller Stefan
• Schraub Martin

Classifications

• C07D311/42

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

• A61P27/02

  Ophthalmic agents · CPC title

• 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

• C07D215/227

  only one oxygen atom which is attached in position 2 · CPC title