Compounds for optically active devices

Patent metadata

Field	Value
Publication number	US-11753387-B2
Application number	US-201816486312-A
Country	US
Kind code	B2
Filing date	Feb 14, 2018
Priority date	Feb 15, 2017
Publication date	Sep 12, 2023
Grant date	Sep 12, 2023

Abstract

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

First claim

The invention claimed is:

1. A compound of formula (I′):

wherein
X is O, S or NR 0 ,
Y is independently of each other O, S or a bond,
—[B]— is selected from formula (1) to formula (4),

X 1 , X 2 , X 3 , X 4 are each independently of each other CR′ or N,
X 5 is each independently O, S, C═O or NR 0 ,
X 6 , X 7 are each independently CR′ or N,
R is at each occurrence independently H, a linear or branched alkyl group having 1 to 10 C atoms, or a cycloalkyl group having 3 to 6 C atoms,
R′ is at each occurrence independently H, F, a linear or branched, non-halogenated, partially or completely halogenated alkyl group having 1 to 20 C atoms, a linear or branched hydroxyalkyl group having 1 to 20 C atoms, a non-halogenated, partially or completely halogenated cycloalkyl group having 3 to 6 C atoms, a linear or branched, non-halogenated, partially or completely halogenated alkoxy group having 1 to 20 C atoms, or a linear or branched, non-halogenated, partially or completely halogenated thioalkyl group having 1 to 20 C atoms,
R 0 is at each occurrence independently a linear or branched alkyl group having 1 to 10 C atoms or a cycloalkyl group having 3 to 6 C atoms,
R 1 is a polymerizable group selected from:
an alkenyl group of formula (5),

wherein
X 10 is O, S, C(═O), or C(═O)O,
R 8 , R 9 , R 10 are at each occurrence independently of each other selected from H, F, a linear or branched, non-fluorinated, partially or completely fluorinated alkyl having 1 to 20 C atoms or aryl with 6 to 14 C atoms, and
c is 0 or 1;
trialkoxysilyl groups or dialkoxyalkylsilyl groups where the alkyl and/or alkoxy groups are each independently linear or branched having 1 to 6 C atoms; and
silyl groups of formula (6), (7) or (8),

where alkyl means at each occurrence independently of each other a linear or branched alkyl group having 1 to 6 C atoms and the asterisk “*” denotes at each occurrence independently of each other a linkage to the linker [-R 2 -Y] n and/or [Y-R 2 ] m ,

R 2 — is —(C(R) 2 ) o — or —(C(R) 2 ) p —X 8 —(C(R) 2 ) q —(X 9 ) s —(C(R) 2 ) r —;
o is 1 to 20,
X 8 , X 9 are at each occurrence independently O, S or NR 0 ,
s is 0 or 1,
p, q are at each occurrence independently 1 to 10,
r is at each occurrence independently 0 to 10, wherein the overall number of atoms for —(C(R) 2 ) p —X 8 —(C(R) 2 ) q —(X 9 ) s —(C(R) 2 ) r — is up to 20 atoms,
R 3 , R 4 , R 5 , R 6 are at each occurrence independently R′,
R 7 is R′.

2. The compound according to claim 1 , wherein -[B]- is of formula (1) or formula (2).

3. The compound according to claim 1 , wherein X 1 , X 3 , and X 4 in formulae (1) or (2) are CR′ and R′ has at each occurrence independently a meaning as indicated in claim 1 .

4. The compound according to claim 1 , wherein X 2 is CR′ and R′ has a meaning as indicated in claim 1 .

5. The compound according to claim 1 , wherein at least one R′ within X 1 , X 2 , X 3 , X 4 , X 6 or X 7 in formulae (1) to (4) is not H.

6. The compound according to claim 1 , wherein —R 2 — is at each occurrence independently —(C(R) 2 ) o —, and R and o have the meanings indicated in claim 1 .

7. The compound according to claim 1 , wherein R 1 is at each occurrence independently an acryl or methacryl radical.

8. The compound according to claim 1 , wherein the compound is selected from the group consisting of:

9. An oligomer or polymer comprising a polymerized compound of formula (I′) according to claim 1 .

10. A composition comprising at least one compound of formula (I′) according to claim 1 .

11. A composition comprising at least one oligomer or polymer according to claim 9 .

12. An article comprising at least one oligomer or polymer of claim 9 .

13. An article according to claim 12 , wherein said article is an intraocular lens.

14. The article according to claim 12 , wherein said article is an ophthalmic device.

15. The article according to claim 14 , wherein said ophthalmic device is a lens, a keratoprosthesis, a cornea inlay, or a cornea ring.

16. The article according to claim 12 , wherein said article is an eye implant.

17. A process of changing the optical properties of an article according to claim 12 , said process comprising:
providing an article according to claim 12 , and
subsequently exposing said article to irradiation having a wavelength of at least 200 nm and at most 1500 nm.

18. An article according to claim 13 , wherein the ophthalmic device comprises one or more optic components and one or more haptic components, wherein the one or more optic components serve as a lens and the one or more haptic components are attached to the one or more optic components and hold the one or more optic components in place in the eye.

19. An article according to claim 13 , wherein the article has a one-piece design.

20. An article according to claim 13 , wherein the article has a multi-piece design.

21. A process of forming an article, said process comprising:
introducing a compound according to claim 1 into a mold and polymerizing said compound to form a blank,
transforming the blank into the article, wherein said article is an ophthalmic device.

22. A process of forming an article, said process comprising:
polymerizing a compound according to claim 1 to form an oligomer or polymer composition,
introducing the oligomer or polymer composition into a mold to form a blank, and
shaping the blank by cutting, optic lathe cutting, optic milling, and/or haptic milling to form the article, wherein said article is an ophthalmic device.

23. A copolymer comprising a polymerized compound of formula (I′) according to claim 1 wherein the polymerizable group R 1 forms part of a co-polymer backbone.

24. The copolymer according to claim 19 , wherein said copolymer comprises one or more constitutional units M 0 of formula (5-p-1:

Assignees

• Johnson & Johnson Surgical Vision Inc

Inventors

• Dobelmann-Mara Lars
• Riedmueller Stefan
• Schraub Martin

Classifications

• C07D209/12 Primary

  Radicals substituted by oxygen atoms · CPC title

• C07D307/79 Primary

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

• C07D333/64

  Oxygen atoms · CPC title

• C07D405/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D409/02

  containing two hetero rings · CPC title