Photochromic bis-naphthopyran compounds and methods for their manufacture
AssigneeJohnson & Johnson Vision Care, Inc.
InventorsWeili Zhao, Erick M. Carreira
Life of this patent
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Abstract
The invention provides photochromic bis-naphthopyran compounds as well as methods for their manufacture and their use. The bis-naphthopyran compounds of the invention exhibit a wide range of color, i.e., from pink to purple to blue gray, upon activation by a source of UV light. Additionally, the bis-naphthopyran compounds of the present invention exhibit broad coloration ability, fast response as to both color change on activation and return to original color, and good fatigue-resistance.
Claims4
A composition comprising a compound of the formula:
- wherein X is sulfur or oxygen;
- R′, R″ are the same or different and are each independently hydrogen, hydroxy, halogen, nitro, cyano, allyl, linear or branched (C1-C20)alkyl, (C3-C20)cycloalkyl, (C1-C20)alkoxy, (C1-C20)alkylacetylenyl, phenylacetylenyl, (C1-C20)alkenyl, phenylvinyl, halo(C1-C20)alkyl, halo(C3-C20)cycloalkyl, halo(C1-C20)alkoxy, aryl, aryloxy or heteroaryl optionally substituted with (C1-C6)alkyl or (C1-C6)alkoxy;
- arylalkyl or heteroarylalkyl;
- nitrogen-containing heterocyclic ring having 5 or 6 atoms optionally substituted (C1-C6)alkyl or (C1-C6)alkoxy, —N(R1)R2, CON(R1)R2, wherein R1 and R2 may be the same or different and are each independently hydrogen, (C1-C20)alkyl, (C3-C20)cycloalkyl, and optionally substituted phenyl;
- —OCOR, —COOR or —COR, wherein R represents hydrogen, (C1-C20)alkyl, (C3-C20)cycloalkyl, or aryl or heteroaryl optionally substituted with (C1-C6)alkyl or (C1-C6)alkoxy;
- A′, A″ may be same or different and are each independently:
- linear or branched (C1-C12)alkyl, (C3-C12)cycloalkyl, aryl(C1-C6)alkyl or heteroaryl(C1-C6)alkyl, (C1-C6)alkoxy(C1-C6)alkyl, (C1-C12)alkoxy, halo(C1-C12)alkyl, (C1-C12)haloalkoxy, (C1-C12)alkylthio;
- optionally substituted aryl groups;
- optionally substituted heteroaryl groups;
- a group of the following formulae:
- wherein B is hydrogen, (C1-C12)alkyl or optionally substituted aryl;
- unsubstituted or mono-substituted pyrazolyl, pyridyl, imidazolyl, pyrazolinyl, imidazolinyl, or acridinyl, each of the said substituents selected from the group consisting of (C1-C6)alkyl, (C1-C6)alkoxy, fluoro, chloro, and phenyl.
- (f) a group of the following formulae:
- wherein C, D may be the same or different and are each independently carbon, oxygen, (C1-C12)alkyl nitrogen, or (C1-C12)acyl nitrogen;
- R3 and R4 are each hydrogen or (C1-C12)alkyl;
- and
- wherein the phenyl moiety is optionally substituted with (C1-C12)alkyl, (C1-C12)alkoxy, (C2-C12)acyl, fluoro, or chloro;
- n is an integer from 1 to 8;
- and
- m is an integer from 0 to 3;
- and
- a photochromic compound selected from the group consisting of naphthopyran, spirooxazine, one or more nonphotochromic dyes, or a combination thereof.
A composition comprising a compound selected from the group consisting of:
- 5,5′-Bis[3-(p-methoxyphenyl)-[3H]-naphtho[2,1-b]pyran-3-yl]-2,2′-bithiophene;
- 5,5′-Bis[3-(p-methylphenyl)-[3H]-naphtho[2,1-b]pyran-3-yl]-2,2′-bithiophene;
- 5,5′-Bis[3-(p-fluorophenyl)-[3H]-naphtho[2,1-b]pyran-3-yl]-2,2′-bithiophene;
- 5,5′-Bis[3-(o-fluorophenyl)-[3H]-naphtho[2,1-b]pyran-3-yl]-2,2′-bithiophene;
- 5,5′″-Bis[3-(p-methoxyphenyl)-[3H]-naphtho[2,1-b]pyran-3-yl]-[2,2′,5′,2″,5″,2′″]-quaterthiophene;
- 5,5′″-Bis[3-(naphthalene-2-yl)-[3H]-naphtho[2,1-b]pyran-3-yl]-[2,2′,5′,2″,5″,2′″]-quaterthiophene;
- or
- 5,5′″-Bis[3-(o-fluorophenyl)-[3H]-naphtho[2,1-b]pyran-3-yl]-[2,2′,5′,2″,5″,2′″]-quaterthiophene
- and a photochromic compound selected from the group consisting of naphthopyran, spirooxazine, one or more nonphotochromic dyes, or a combination thereof.
Dependencies are inferred from the claim text.