Phenylethynylnaphthalene dyes and methods for their use

Patent metadata

Field	Value
Publication number	US-2018237641-A1
Application number	US-201615553546-A
Country	US
Kind code	A1
Filing date	Feb 26, 2016
Priority date	Feb 26, 2015
Publication date	Aug 23, 2018
Grant date	—

Abstract

Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I), including salts thereof, wherein R 1a , R 1b , R 1c , R 1d , R 1e , R 1f , R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i , R 2j , x and y are as defined herein. Methods associated with preparation and use of such compounds are also provided.

First claim

1 . A compound having the following structure (I):

or a salt thereof, wherein:
R 1a , R 1b , R 1c , R 1d , R 1e and R 1f are each independently absent, H, halo, nitro, C 1 -C 6 alkyl, —SO 3 − , —SO 3 alkyl, C 1 -C 6 alkoxy, aryl, aryloxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyloxy, arylcarbonyl, arylcarbonyloxy, amino, alkylamino, arylamino, aralklyamino, -L 1 -(R 3 ) z -L 2 -M or -L 1 -(R 3 ) z -L 2 -S—S-L 2 -(R 3 ) z -L 1 -I, where I represents, independently, a further compound of structure (I); or one of R 1a , R 1b , R 1c , R 1d , R 1e or R 1f joins with another one of R 1a , R 1b , R 1c , R 1d , R 1e or R 1f to form a carbocyclic or heterocyclic ring and the remaining R 1a R 1b , R 1c , R 1d , R 1e and R 1f are each independently absent, H, halo, nitro, C 1 -C 6 alkyl, —OSO 2 − , —OSO 2 alkyl, C 1 -C 6 alkoxy, aryl, aryloxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyloxy, arylcarbonyl, arylcarbonyloxy, amino, alkylamino, arylamino, aralklyamino, -L 1 -(R 3 ) z -L 2 -M or -L 1 -(R 3 ) z -L 2 -S—S-L 2 -(R 3 ) z -L 1 -I, where I represents, independently, a further compound of structure (I);
R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i and R 2j are each independently H, halo, C 1 -C 6 alkoxy, aryloxy, amino, alkylamino, arylamino, aralklyamino, heterocyclyl, -L 1 -(R 3 ) z -L 2 -M or -L 1 -(R 3 ) z -L 2 -S—S-L 2 -(R 3 ) z -L 1 -I, where I represents, independently, a further compound of structure (I); or one or more of R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i or R 2j join with another one or more of R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i or R 2j on the same ring to form a mono or fused bicyclic carbocyclic or heterocyclic ring and the remaining R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i and R 2j are each independently H, halo, C 1 -C 6 alkoxy, aryloxy, amino, alkylamino, arylamino, aralklyamino, heterocyclyl, -L 1 -(R 3 ) z -L 2 -M or -L 1 -(R 3 ) z -L 2 -S—S-L 2 -(R 3 ) z -L 1 -I, where I represents, independently, a further compound of structure (I);
R 3 is, at each occurrence, independently a mono or bivalent functional group selected from the group consisting of polyalkyether, polyalkylenether, hydroxylalkoxy, hydroxylalkyl, hydroxylalkylene, aminoalkylene, aminoalkoxy, hydroxylpolyalkyether, hydroxylpolyalkylenether, aminopolyalkyether, aminopolyalkylenether, phosphate, thiophosphate, phospho, thiophospho, phosphoalkyl, phosphoalkylene, phosphoalkylether, thiophosphoalkyl, thiophosphoalkylene, thiophosphoalkylether, phosphoramidite and activated phosphorous;
M is absent, H or a moiety capable of bonding with an analyte molecule or a solid support; or M is an analyte molecule or solid support; and
L 1 and L 2 are, at each occurrence, independently an optional linker;
x and y are each independently an integer from 0 to 4, and the sum of x and y is 2 or greater;
z is an integer from 1 to 10; and

provided at least one of R 1a , R 1b , R 1c , R 1d , R 1e , R 1f , R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i or R 2j is -L 1 -(R 3 ) z -L 2 -M or -L 1 -(R 3 ) z -L 2 -S—S-L 2 -(R 3 ) z -L 1 -I, where I represents, independently, a further compound of structure (I).

2 . The compound of claim 1 , wherein the sum of x and y is 2.

3 . The compound of claim 1 , wherein x is 0 and y is 2.

4 . The compound of claim 1 , wherein the compound has the following structure (Ia):

5 . The compound of claim 4 , wherein the compound has the following structure (Ia′):

6 . The compound of claim 1 , wherein R 1a is -L 1 -(R 3 ) z -L 2 -M.

7 - 12 . (canceled)

13 . The compound of claim 1 , wherein at least one of R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i or R 2j is amino, alkylamino, arylamino, aralklyamino or heterocyclyl.

14 - 17 . (canceled)

18 . The compound of claim 1 , wherein one or more of R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i Or R 2j join with another one or more of R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i or R 2j on the same ring to form a mono or fused bicyclic carbocyclic or heterocyclic ring and the remaining R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , R 2h , R 2i and R 2j are each independently H, halo, C 1 -C 6 alkoxy, aryloxy, amino, alkylamino, arylamino, aralklyamino, heterocyclyl, -L 1 -(R 3 ) z -L 2 -M or -L 1 -(R 3 ) z -L 2 -S—S-L 2 -(R 3 ) z -L 1 -I, where I represents, independently, a further compound of structure (I).

19 . The compound of claim 18 , wherein the compound has one of the following structures:

20 . The compound of claim 1 , wherein at least one of R 2a , R 2b , R 2d , R 2e , R 2f , R 2g , R 2i or R 2j is halo, alkoxy or aryloxy.

21 - 24 . (canceled)

25 . The compound of claim 1 , wherein each of R 2a , R 2b , R 2d , R 2e , R 2f , R 2g , R 2i and R 2j is H.

26 . The compound of claim 1 , wherein R 1a , R 1b , R 1c , R 1d , R 1e and R 1f are each independently absent, H, halo, nitro, C 1 -C 6 alkyl, —SO 3 − , —SO 3 alkyl, C 1 -C 6 alkoxy, aryl, aryloxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyloxy, arylcarbonyl, arylcarbonyloxy, amino, alkylamino, arylamino, aralklyamino, -L 1 -(R 3 ) z -L 2 -M or -L 1 -(R 3 ) z -L 2 -S—S-L 2 -(R 3 ) z -L 1 -I, where I represents, independently, a further compound of structure (I).

27 - 35 . (canceled)

36 . The compound of claim 1 , wherein one of R 1a , R 1b , R 1c , R 1d , R 1e or R 1f joins with another one of R 1a , R 1b , R 1c , R 1d , R 1e or R 1f to form a carbocyclic or heterocyclic ring and the remaining R 1a , R 1b , R 1c , R 1d , R 1e and R 1f are each independently absent, H, halo, nitro, C 1 -C 6 alkyl, —OSO 2 − , —OSO 2 alkyl, C 1 -C 6 alkoxy, aryl, aryloxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyloxy, arylcarbonyl, arylcarbonyloxy, amino, alkylamino, arylamino, aralklyamino, -L 1 -(R 3 ) z -L 2 -M or -L 1 -(R 3 ) z -L 2 -S—S-L 2 -(R 3 ) z -L 1 -I, where I represents, independently, a further compound of structure (I).

37 . The compound of claim 1 , wherein the compound has one of the following structures:

38 - 41 . (canceled)

42 . The compound of claim 1 , wherein —(R 3 ) z -L 2 -M has one of the following structures:

43 . The compound of claim 1

Assignees

• Sony Corp America
• Sony Corp

Inventors

• Battrell C Frederick
• Matray Tracy
• Sherif Hesham
• Vanbrunt Michael

Classifications

• C09B69/109

  containing other specific dyes · CPC title

• G01N33/52

  Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper {and including single- and multilayer analytical elements (immunological elements G01N33/54386; involving labelled immunochemicals G01N33/58; for haemoglobin or occult blood G01N33/72)} · CPC title

• C09B69/101

  containing an anthracene dye · CPC title

• C07F9/2429

  of arylalkanols · CPC title

• C09B69/00

  Dyes not provided for by a single group of this subclass · CPC title