US 11,866,588 B2
Polymerizable near-IR dyes
Soya Gamsey, San Francisco, CA (US); Alex Kutyavin, Lake Stevens, WA (US); and Jacob William Clary, Moss Beach, CA (US)
Assigned to Profusa, Inc., Emeryville, CA (US)
Filed by Profusa, Inc., South San Francisco, CA (US)
Filed on Jun. 21, 2019, as Appl. No. 16/448,186.
Application 16/448,186 is a continuation of application No. PCT/US2017/067847, filed on Dec. 21, 2017.
Claims priority of provisional application 62/437,599, filed on Dec. 21, 2016.
Prior Publication US 2020/0140690 A1, May 7, 2020
Int. Cl. C09B 69/10 (2006.01); C09B 23/00 (2006.01); C09B 23/08 (2006.01); C09B 23/10 (2006.01); C09K 11/06 (2006.01); C09B 23/01 (2006.01)
CPC C09B 69/105 (2013.01) [C09B 23/0066 (2013.01); C09B 23/083 (2013.01); C09B 23/107 (2013.01); C09K 11/06 (2013.01); C09K 2211/1466 (2013.01)] 20 Claims
 
1. A polymerizable near-IR dye having a structure according to formula (I):

OG Complex Work Unit Chemistry
or a tautomer, salt, hydrate, or solvate thereof,
wherein:
Z1 is absent, O, NRZ1, or S;
RZ1 is H, optionally substituted C1-C10 alkyl, or optionally substituted C2-C10 heteroalkyl;
X1 is absent, optionally substituted C6-C10 arylene, or optionally substituted C1-C10 heteroarylene;
Z2 is absent, NRX1, O, S, NRX2C(O), OC(O), SC(O), C(O)O, C(O)NRX3, C(S)O, or C(O)S;
Z3 is absent or H;
RX1, RX2, and RX3 are each independently H, optionally substituted C1-C10 alkyl, or optionally substituted C1-C10 heteroalkyl;
L1 is absent, optionally substituted C1-C30 alkylene, or optionally substituted C1-C30 heteroalkylene;
Q1 is NRZ3C(O)C(RQ1)CH2, OC(O)C(RQ1)CH2, or SC(O)C(RQ1)CH2;
RZ3 is H, optionally substituted C1-C10 alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted C1-C10 heteroalkyl, or optionally substituted C1-C10 cycloheteroalkyl;
RQ1 is H, Me, Et, or n-Pr;
each of Y1 and Y4, independently, is absent or optionally substituted C1-C4 alkylene or optionally substituted C2-C4 heteroalkylene;
each of Y2 and Y3, independently, is absent or, together with the carbon atoms to which each is attached, form optionally substituted C6-C10 aryl or optionally substituted C2-C10 heteroaryl;
Y5 is absent or N or CR7;
R7 is H, optionally substituted C1-C10 alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted C1-C10 heteroalkyl, or optionally substituted C1-C10 cycloheteroalkyl;
each of W1 and W2, independently, is NR2, S, O, Se, or CR3R4;
R2, R3, and R4 are independently H, optionally substituted C1-C30 alkyl, optionally substituted C1-C30 heteroalkyl, or -L2-Q2;
L2 is optionally substituted C1-C30 alkylene or optionally substituted C1-C30 heteroalkylene;
Q2 is H, C(RQ1)CH2, C6H4CHCH2, NRZ3C(O)C(RQ1)CH2, OC(O)C(RQ1)CH2, or SC(O)C(RQ1)CH2;
each of R5 and R6, independently, is -L3-Q3, optionally substituted C1-C30 alkyl, or optionally substituted C6-C10 aryl;
L3 is optionally substituted C1-C30 alkylene or optionally substituted C1-C30 heteroalkylene;
Q3 is H, C(RQ1)CH2, C6H4CHCH2, NRZ3C(O)C(RQ1)CH2, OC(O)C(RQ1)CH2, or SC(O)C(RQ1)CH2; and
each k is independently 0 or 1.