IP Library Patent Application 19061328
Patent Application
App. No. 19/061,328

NEAR-IR GLUCOSE SENSORS

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Patent No.
US None
App. No.
19/061,328
Abstract

Glucose-sensing luminescent dyes, polymers, and sensors are provided. Additionally, systems including the sensors and methods of using these sensors and systems are provided.

Claims (67)

1 - 160 . (canceled)

161 . A compound of Formula (IV-I):

or an isomer, a tautomer, a solvate, or a salt thereof, wherein:

R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , and R 14 are each independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 10 heteroalkyl, halogen, —C(O)R′, —COOR′, —C(O)NH 2 , —C(O)NR′R″, —CF 3 , —CN, —SO 3 H, —SO 2 CF 3 , —SO 2 R′, —SO 2 NR′R″, —N(R′) 2 , —N(R′) 3 + , —NO 2 , —OR′, —NHC(O)R′, —OC(O)R′, or phenyl, wherein R′ and R″ are each independently H or C 1 -C 6 alkyl; or R′ and R″ together with the nitrogen atom forms a 5- or 6-membered heterocycle optionally containing one additional heteroatom selected from S, O, or N;

R 2 and R 15 are each independently, H or C 1 -C 6 alkyl;

R 9 and R 10 are independently H, C 1 -C 6 alkyl, or —NHC(O)C(CH 3 )CH 2 ;

L 1 and L 3 are independently a bond or a linker group selected from optionally substituted C 1 -C 10 alkylene, optionally substituted C 2 -C 10 alkenylene, optionally substituted C 2 — C 10 alkynylene, optionally substituted C 2 -C 20 heteroalkylene, optionally substituted —(CH 2 CH 2 O) n CH 2 —, optionally substituted —CH 2 (CH 2 CH 2 O) n —, optionally substituted —(CH 2 CH 2 O) n CH 2 CH 2 —, optionally substituted —CH 2 CH 2 (CH 2 CH 2 O) n —, optionally substituted (CH 2 CH 2 O) n —, wherein n is an integer between 1 and 10;

L 2 is a bond, optionally substituted phenylene, optionally substituted-alkylene-phenylene-, optionally substituted-phenylene-alkylene-, or optionally substituted 5- or 6-membered heteroarylene;

Y 1 is —Si(R d )(R e )—, wherein R d and R c are each H, —OH, C 1 -C 6 alkyl, C 6 -C 10 aryl, C 1 -C 6 alkoxy, or C 6 -C 10 aryloxy;

R 20 , R 21 , R 23 , and R 24 are each independently H; C 1 -C 6 alkyl optionally substituted with —NH 2 or —NH 3 ′; C 2 -C 6 alkenyl; or benzyl optionally substituted with —B(OR 2 ) 2 ;

R 22 , R 25 , R 26 , and R 27 are each independently H or C 1 -C 6 alkyl;

alternatively, (R 21 and R 20 ) and/or (R 23 and R 24 ) together with the nitrogen atom to which they are attached, form a 6-, 5-, or 4-membered saturated or partially saturated ring;

alternatively, (R 21 and R 22 ), (R 24 and R 25 ), (R 23 and R 27 ), and/or (R 26 and R 20 ), together with the atoms to which they are attached, form an optionally substituted 6- or 5-membered saturated, unsaturated, or partially saturated ring.

162 - 166 . (canceled)

167 . The compound of claim 161 , having the following structure of formula (IV-IB):

or an isomer, a tautomer, a solvate, or a salt thereof, wherein:

R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , and R 14 are each independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 10 heteroalkyl, halogen, —C(O)R′, —COOR′, —C(O)NH 2 , —C(O)NR′R″, —CF 3 , —CN, —SO 3 H, —SO 2 CF 3 , —SO 2 R′, —SO 2 NR′R″, —N(R′) 2 , —N(R′) 3 + , —NO 2 , —OR′, —NHC(O)R′, —OC(O)R′, or phenyl;

R′ and R″ are each independently H or C 1 -C 6 alkyl; or optionally R′ and R″ in —SO 2 NR′R″ can together form a 5- or 6-membered heterocycle with the nitrogen atom to which they are attached, wherein the heterocycle optionally contains one additional heteroatom selected from S, O, or N;

R d and R c are each H, C 1 -C 6 alkyl, C 6 -C 10 aryl, C 1 -C 6 alkoxy, or C 6 -C 10 aryloxy;

R 2 and R 15 are each independently, H or C 1 -C 6 alkyl;

R 9 and R 10 are independently H, C 1 -C 6 alkyl, or —NHC(O)C(CH 3 )CH 2 ;

L 1 and L 3 are independently a bond or a linker group selected from optionally substituted C 1 -C 10 alkylene, optionally substituted C 2 -C 10 alkenylene, optionally substituted C 2 — C 10 alkynylene, optionally substituted C 2 -C 20 heteroalkylene, optionally substituted-(CH 2 CH 2 O) n CH 2 —, optionally substituted —CH 2 (CH 2 CH 2 O) n —, optionally substituted —(CH 2 CH 2 O) n CH 2 CH 2 —, optionally substituted —CH 2 CH 2 (CH 2 CH 2 O) n —, optionally substituted (CH 2 CH 2 O) n —, wherein n is an integer between 1 and 5;

L 2 is a bond; phenylene optionally substituted with at least one substituent selected from C 1 -C 3 alkyl, C 1 -C 3 alkoxy, or halogen; optionally substituted —C 1 -C 3 alkylene-phenylene-; optionally substituted-phenylene-C 1 -C 3 alkylene-;

R 20 , R 21 , R 23 , and R 24 are each independently H; C 1 -C 6 alkyl optionally substituted with —NH 2 or —NH 3 ′; C 2 -C 6 alkenyl; or benzyl optionally substituted with —B(OR 2 ) 2 ;

R 22 , R 25 , R 26 , and R 27 are each independently H or C 1 -C 6 alkyl;

alternatively, (R 21 and R 20 ) and/or (R 23 and R 24 ) together with the nitrogen atom to which they are attached, form a 6-, 5-, or 4-membered saturated or partially saturated ring;

alternatively, (R 21 and R 22 ), (R 24 and R 25 ), (R 23 and R 27 ), and/or (R 26 and R 20 ), together with the atoms to which they are attached, form an optionally substituted 6- or 5-membered saturated, unsaturated, or partially saturated ring; and

wherein when L 2 is a bond, at least one of R 20 , R 21 , R 23 , and R 24 is benzyl optionally substituted with —B(OR 2 ) 2 ;

provided that the compound is not compounds 27, 54, 63, 64, 65, 66, 67, 69, 73, 74, 75, 76, 77, 81, 82, and 83.

168 - 169 . (canceled)

170 . The compound of claim 161 , wherein L 2 is a bond; phenylene optionally substituted with at least one substituent selected from C 1 -C 3 alkyl, C 1 -C 3 alkoxy, or halogen;

171 . The compound of claim 161 , wherein L 2 is selected from a bond, optionally substituted phenylene, optionally substituted-alkylene-phenylene-, optionally substituted-phenylene-alkylene-, or optionally substituted 5- or 6-membered heteroarylene; wherein the optional substituent is halogen, C 1 -C 3 alkyl, or C 1 -C 3 alkoxy.

172 . The compound of claim 161 , wherein L 2 is selected from a bond,

173 . The compound of claim 161 a wherein L 2 is

each is optionally substituted.

174 . The compound of claim 161 , wherein R d and R c are each methyl.

175 . The compound of claim 161 , wherein R 9 , R 10 , or both, is —NHC(O)C(CH 3 )CH 2 .

176 . (canceled)

177 . The compound of claim 161 , wherein L 1 , L 3 , or both, is C 1 -C 10 alkylene, C 2 -C 20 heteroalkylene, —(CH 2 CH 2 O) n CH 2 —, —(CH 2 CH 2 O) n CH 2 CH 2 —, or —(CH 2 CH 2 O) n —.

178 . (canceled)

179 . The compound of claim 161 , wherein L 1 and L 3 is —CH 2 —CH 2 —CH 2 — or —(CH 2 CH 2 O) 4 CH 2 CH 2 —.

180 . The compound of claim 161 , wherein:

a)_R 1 1, R 14 , and R 12 are H;

b) R 22 , R 25 , R 26 , and R 27 are H: or

c) R 1 , R 5 , and R 6 are H;

d) R 2 and R 15 are each H.

181 . (canceled)

182 . (canceled)

183 . The compound of claim 161 , wherein at least one of R 3 , R 4 , R 7 , and R′ is selected from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, halogen, —SO 2 NR′R″, —CN, and —NO 2 .

184 . The compound of claim 161 wherein at least one of R 3 , R 4 , R 7 , and R′ is selected from methyl, —CF 3 , methoxy, halogen, —SO 2 N(Me) 2 , —SO 2 NHMe, —CN, —NO 2 , and

185 . (canceled)

186 . The compound of claim 161 , wherein R 20 , R 21 , R 23 , and R 24 are each independently H; C 1 -C 4 alkyl optionally substituted with —NH 2 or —NH 3 ; C 2 -C 4 alkenyl; or benzyl optionally substituted with —B(OR 2 ) 2 ; or alternatively, (R 21 and R 22 ), (R 24 and R 25 ), (R 23 and R 27 ), and/or (R 26 and R 20 ), together with the atoms to which they are attached, form an optionally substituted 6- or 5-membered saturated, unsaturated, or partially saturated ring.

187 . The compound of claim 161 , wherein R 20 , R 21 , R 23 , and R 24 are each independently H, C 1 -C 6 alkyl, or benzyl optionally substituted with —B(OR 2 ) 2 .

188 . (canceled)

189 . (canceled)

190 . The compound of claim 167 selected from

or an isomer, a tautomer, a solvate, or a salt thereof

191 . The compound of claim 167 selected from

192 . (canceled)

193 . (canceled)

194 . A composition comprising a compound of claim 161 .

195 . A sensor for detecting an analyte comprising a polymer, wherein the polymer comprises one or more residues of claim 161 .

196 - 211 . (canceled)

212 . A method of measuring blood glucose concentration in a mammalian subject, comprising:

a) implanting a sensor of claim 161 into subcutaneous tissue of a mammalian subject;

b) measuring at least one wavelength of light in the glucose-concentration-dependent luminescent signal from the sensor with a detector to produce a detected luminescent signal; and

c) processing the detected luminescent signal to produce a glucose concentration.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2026
From: GAMSEY, SOYA; BERNAT, VIACHASLAU; KUTYAVIN, ALEX; CLARY, JACOB WILLIAM; PRADHAN, SULOLIT
To: PROFUSA, INC.
Reel/Frame 073677/0016 →