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US 11,299,512 B2Granted
Cyclic di-nucleotide compounds and methods of use
AssigneesImmuneSensor Therapeutics, Inc., Board of Regents, The University of Texas System
InventorsBoyu Zhong, Heping Shi, Yuanwei Dai, Qi Wei, Chuo Chen, Zhijian Chen, Lijun Sun
Life of this patent
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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.
Claims34
A compound, wherein the compound is of Formula Ic:
- wherein
- Z12 and Z15 are N;
- Z13, Z14, Z16 and Z17 are independently CH or N;
- R3 is C2alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6alkoxy, C1-6hydroxyalkoxy, amino, C1-6alkylamino, di(C1-6alkyl)amino, or azido groups;
- R4 is hydroxyl;
- R9 and R10 are independently hydroxyl;
- thiol;
- C1-6alkyl;
- C1-6alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6alkoxy, C1-6hydroxyalkoxy, amino, C1-6alkylamino, di(C1-6alkyl)amino, or azido groups;
- C1-6alkoxy;
- C1-6alkoxy functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6hydroxyalkoxy, amino, C1-6alkylamino, di(C1-6alkyl)amino, or azido groups;
- C3-5alkenyl-O—;
- C3-5alkynyl-O—;
- oligo(ethylene glycol);
- poly(ethylene glycol);
- borano (—BH3−);
- or —NR7R8;
- R7 and R8 are independently hydrogen;
- C1-6alkyl;
- C1-6alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6alkoxy, C1-6hydroxyalkoxy, amino, C1-6alkylamino, di(C1-6alkyl)amino, or azido groups;
- cyclic —(C1-6alkyl)-;
- cyclic —(C1-6alkyl)- functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6alkoxy, C1-6hydroxyalkoxy, amino, C1-6alkylamino, or di(C1-6alkyl)amino groups;
- cyclic —(C1-6oxaalkyl)-;
- or cyclic —(C1-6oxaalkyl)-functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6hydroxyalkoxy, amino, C1-6alkylamino, or di(C1-6alkyl)amino groups;
- or a pharmaceutically acceptable salt thereof.
22 more elements
A compound, wherein the compound is of Formula Ic:
- wherein
- Z12 and Z15 are N;
- Z13 and Z16 are CH;
- Z14 and Z17 are independently CH or N;
- R3 is C2alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6alkoxy, C1-6hydroxyalkoxy, amino, C1-6alkylamino, di(C1-6alkyl)amino, or azido groups;
- R4 is hydroxyl;
- R9 and R10 are independently hydroxyl or thiol;
- or a pharmaceutically acceptable salt thereof.
5 more elements
A compound, wherein the compound is of Formula Ic:
- wherein
- Z12 and Z15 are N;
- Z13, Z14, Z16 and Z17 are independently CH or N;
- R3 is C1-6alkyl functionalized with one or more halogen, thiol, or hydroxyl;
- R4 is hydroxyl;
- R9 and R10 are independently hydroxyl;
- thiol;
- C1-6alkyl;
- C1-6alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6alkoxy, C1-6hydroxyalkoxy, amino, C1-6alkylamino, di(C1-6alkyl)amino, or azido groups;
- C1-6alkoxy;
- C1-6alkoxy functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6hydroxyalkoxy, amino, C1-6alkylamino, di(C1-6alkyl)amino, or azido groups;
- C3-5alkenyl-O—;
- C3-5alkynyl-O—;
- oligo(ethylene glycol);
- poly(ethylene glycol);
- borano (—BH3−);
- or —NR7R8;
- R7 and R8 are independently hydrogen;
- C1-6alkyl;
- C1-6alkyl functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6alkoxy, C1-6hydroxyalkoxy, amino, C1-6alkylamino, di(C1-6alkyl)amino, or azido groups;
- cyclic —(C1-6alkyl)-;
- cyclic —(C1-6alkyl)- functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6alkoxy, C1-6hydroxyalkoxy, amino, C1-6alkylamino, or di(C1-6alkyl)amino groups;
- cyclic —(C1-6oxaalkyl)-;
- or cyclic —(C1-6oxaalkyl)-functionalized with one or more halogen, thiol, hydroxyl, carboxyl, C1-6hydroxyalkoxy, amino, C1-6alkylamino, or di(C1-6alkyl)amino groups;
- or a pharmaceutically acceptable salt thereof.
22 more elements
A compound, wherein the compound is of Formula Ic:
- wherein
- Z12 and Z15 are N;
- Z13 and Z16 are CH;
- Z14 and Z17 are independently CH or N;
- R3 is C1-6alkyl functionalized with one or more halogen, thiol, or hydroxyl;
- R4 is hydroxyl;
- R9 and R10 are independently hydroxyl or thiol;
- or a pharmaceutically acceptable salt thereof.
5 more elements
Dependencies are inferred from the claim text.