US2022340613A1PendingUtilityA1
Cyclic di-nucleotide compounds and methods of use
Assignee: IMMUNESENSOR THERAPEUTICS INCPriority: Mar 18, 2016Filed: Mar 17, 2022Published: Oct 27, 2022
Est. expiryMar 18, 2036(~9.7 yrs left)· nominal 20-yr term from priority
A61K 31/7084C07H 21/02C07H 19/213A61K 45/06C07H 21/00C07H 21/04A61P 35/00A61P 37/02A61P 43/00A61P 31/00A61P 37/04A61K 9/51
70
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Claims
Abstract
Disclosed are cyclic-di-nucleotide cGAMP analogs, methods of synthesizing the compounds, pharmaceutical compositions comprising the compounds thereof, and use of compounds and compositions in medical therapy.
Claims
exact text as granted — not AI-modified1 - 80 . (canceled)
81 . A method for treating a cancer responsive to activation of the STING pathway by administering a compound, wherein the compound is of Formula Ic:
wherein
Z 12 and Z 15 are N;
Z 13 , Z 14 , Z 16 and Z 17 are independently CH or N;
R 3 is C 2 alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 alkoxy, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino, or azido groups;
R 4 is hydroxyl;
R 9 and R 10 are independently hydroxyl; thiol; C 1-6 alkyl; C 1-6 alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 alkoxy, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino, or azido groups; C 1-6 alkoxy; C 1-6 alkoxy functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino, or azido groups; C 3-5 alkenyl-O—; C 3-5 alkynyl-O—; oligo(ethylene glycol); poly(ethylene glycol); borano (—BH 3 − ); or —NR 7 R 8 ;
R 7 and R 8 are independently hydrogen; C 1-6 alkyl; C 1-6 alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 alkoxy, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino, or azido groups; cyclic —(C 1-6 alkyl)-; cyclic —(C 1-6 alkyl)-functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 alkoxy, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, or di(C 1-6 alkyl)amino groups; cyclic —(C 1-6 oxaalkyl)-; or cyclic —(C 1-6 oxaalkyl)-functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, or di(C 1-6 alkyl)amino groups;
or is a pharmaceutically acceptable salt thereof.
82 . The method of claim 81 , wherein Z 13 and Z 16 are CH, and Z 14 and Z 17 are N.
83 . The method of claim 81 , wherein R 9 and R 10 are independently hydroxyl or thiol.
84 . The method of claim 81 , wherein R 3 is C 2 alkyl functionalized with one or more thiol, hydroxyl, carboxyl, C 1-6 hydroxyalkoxy, amino, or C 1-6 alkylamino groups.
85 . The method of claim 81 , wherein R 3 is C 2 alkyl functionalized with one or more halogen, thiol, or hydroxyl.
86 . The method of claim 81 , wherein the compound is of Formula Ic:
wherein
Z 12 and Z 15 are N;
Z 13 and Z 16 are CH;
Z 14 and Z 17 are independently CH or N;
R 3 is C 2 alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 alkoxy, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino, or azido groups;
R 4 is hydroxyl;
R 9 and R 10 are independently hydroxyl or thiol;
or is a pharmaceutically acceptable salt thereof.
87 . The method of claim 86 , wherein R 3 is C 2 alkyl functionalized with one or more thiol, hydroxyl, carboxyl, C 1-6 hydroxyalkoxy, amino, or C 1-6 alkylamino groups.
88 . The method of claim 86 , wherein R 3 is C 2 alkyl functionalized with one or more halogen, thiol, or hydroxyl.
89 . A method for treating a cancer responsive to activation of the STING pathway by administering a compound of Formula Ic:
wherein
Z 12 and Z 15 are N;
Z 13 , Z 14 , Z 16 and Z 17 are independently CH or N;
R 3 is C 1-6 alkyl functionalized with one or more halogen, thiol, or hydroxyl;
R 4 is hydroxyl;
R 9 and R 10 are independently hydroxyl; thiol; C 1-6 alkyl; C 1-6 alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 alkoxy, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino, or azido groups; C 1-6 alkoxy; C 1-6 alkoxy functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino, or azido groups; C 3-5 alkenyl-O—; C 3-5 alkynyl-O—; oligo(ethylene glycol); poly(ethylene glycol); borano (—BH 3 − ); or —NR 7 R 8 ;
R 7 and R 8 are independently hydrogen; C 1-6 alkyl; C 1-6 alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 alkoxy, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino, or azido groups; cyclic —(C 1-6 alkyl)-; cyclic —(C 1-6 alkyl)-functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 alkoxy, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, or di(C 1-6 alkyl)amino groups; cyclic —(C 1-6 oxaalkyl)-; or cyclic —(C 1-6 oxaalkyl)-functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C 1-6 hydroxyalkoxy, amino, C 1-6 alkylamino, or di(C 1-6 alkyl)amino groups;
or a pharmaceutically acceptable salt thereof.
90 . The method of claim 89 , wherein the compound has the structure:
or is a pharmaceutically acceptable salt thereof.
91 . The method of claim 89 , wherein the compound is of Formula Ic:
wherein
Z 12 and Z 15 are N;
Z 13 and Z 16 are CH;
Z 14 and Z 17 are independently CH or N;
R 3 is C 1-6 alkyl functionalized with one or more halogen, thiol, or hydroxyl;
R 4 is hydroxyl;
R 9 and R 10 are independently hydroxyl or thiol;
or a pharmaceutically acceptable salt thereof.
92 . The method of claim 91 , wherein R 3 is C 1 -6alkyl functionalized with hydroxyl.
93 . The method of claim 91 , wherein R 3 is C 1 -6alkyl functionalized with thiol.
94 . The method of claim 91 , wherein R 3 is C 1 -6alkyl functionalized with halogen.
95 . A compound, wherein the compound is selected from:
or is a pharmaceutically acceptable salt thereof.
96 . The compound of claim 95 , wherein the compound is selected from:
or is a pharmaceutically acceptable salt thereof.
97 . The compound of claim 95 , wherein the compound is selected from:
or is a pharmaceutically acceptable salt thereof.
98 . The compound of claim 95 , wherein the compound is selected from:
or is a pharmaceutically acceptable salt thereof.
99 . The compound of claim 95 , wherein the compound is selected from:
or is a pharmaceutically acceptable salt thereof.
100 . The compound of claim 95 , wherein the compound is selected from:
or is a pharmaceutically acceptable salt thereof.
101 . The compound of claim 95 , wherein the compound is
or is a pharmaceutically acceptable salt thereof.
102 . The compound of claim 95 , wherein the compound is
or is a pharmaceutically acceptable salt thereof.
103 . The compound of claim 95 , wherein the compound is
or is a pharmaceutically acceptable salt thereof.
104 . The compound of claim 95 , wherein the compound is
or is a pharmaceutically acceptable salt thereof.
105 . The compound of claim 95 , wherein the compound is
or is a pharmaceutically acceptable salt thereof.
106 . The compound of claim 95 , wherein the compound is
or is a pharmaceutically acceptable salt thereof.
107 . A compound, wherein the compound is selected from:
or is a pharmaceutically acceptable salt thereof.
108 . A compound, wherein the compound is selected from:
or is a pharmaceutically acceptable salt thereof.Join the waitlist — get patent alerts
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