US 12,324,812 B2
Glucopyranosyl derivatives and their uses
Zheng Gu, Dongguan (CN); Wuyong Wu, Dongguan (CN); Panpan Kang, Dongguan (CN); Weihua Wang, Dongguan (CN); Jianyu Liu, Dongguan (CN); and Xinshan Deng, Dongguan (CN)
Assigned to SUNSHINE LAKE PHARMA CO., LTD., Guangdong (CN)
Appl. No. 17/624,963
Filed by SUNSHINE LAKE PHARMA CO., LTD., Guangdong (CN)
PCT Filed Jul. 9, 2020, PCT No. PCT/CN2020/101014
§ 371(c)(1), (2) Date Jan. 5, 2022,
PCT Pub. No. WO2021/004498, PCT Pub. Date Jan. 14, 2021.
Claims priority of application No. 201910618876.5 (CN), filed on Jul. 10, 2019.
Prior Publication US 2023/0086354 A1, Mar. 23, 2023
Int. Cl. C07H 7/04 (2006.01); A61K 31/351 (2006.01); A61K 31/7048 (2006.01); A61K 45/06 (2006.01); A61P 3/10 (2006.01); C07D 309/10 (2006.01); C07H 17/04 (2006.01)
CPC A61K 31/7048 (2013.01) [A61K 31/351 (2013.01); A61K 45/06 (2013.01); A61P 3/10 (2018.01); C07D 309/10 (2013.01); C07H 17/04 (2013.01)] 15 Claims
 
1. A compound having Formula (I) or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a solvate, a pharmaceutically acceptable salt, a dimer, or a trimer thereof,

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wherein,
Y is —(CH2)q—, —O—, —NH—, —S—, —S (═O)— or —S (═O)2—; q is 0, 1, 2 or 3;
L is C1-6 alkylene or C1-6 alkenylene, wherein the L is unsubstituted or substituted with 1, 2 or 3 Ry;
R1 is H, deuterium, F, Cl, Br, I, —OH, —CN, —NO2, —NH2, —SH, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C1-6 alkylamino, C1-6 alkylthio, cyano C1-6 alkyl, amino C1-6 alkyl, hydroxy C1-6 alkyl or C3-6 cycloalkyl;
each of R5 and R6 is independently H, deuterium, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C3-6 cycloalkyl, 5-6 membered heterocyclyl, C6-10 aryl or 5-6 membered heteroaryl; or R5, R6 together with the nitrogen atom they are attached to, form a 5-6 membered heterocyclic ring or a 5-6 membered heteroaromatic ring;
R4 is F, Cl, Br, I, OH, CN, NO2, NH2, —SH, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 alkylamino, hydroxy C1-6 alkyl, cyano C1-6 alkyl, amino C1-6 alkyl, C3-6 cycloalkyl, 5-6 membered heterocyclyl, C6-10 aryl or 5-6 membered heteroaryl, wherein each of the C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 alkylamino, hydroxy C1-6 alkyl, cyano C1-6 alkyl, amino C1-6 alkyl, C3-6 cycloalkyl, 5-6 membered heterocyclyl, C6-10 aryl or 5-6 membered heteroaryl is independently unsubstituted or substituted with 1, 2 or 3 Rx;
each of R2 and R3 is independently H, deuterium, F, Cl, Br, I, OH, CN, NO2, NH2, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C1-6 alkylamino, C1-6 alkylthio, hydroxy C1-6 alkyl, cyano C1-6 alkyl, or amino C1-6 alkyl;
or R2, R3 together with

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they are attached to, form

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wherein the bond to the R2 group is identified by *, and the bond to the R3 group is identified by **;
each of R7 and R8 is independently H, deuterium, F, Cl, Br, I, OH, CN, NO2, NH2, —SH, C1-6 alkyl, C1-6 alkoxy, C1-6 alkylamino, C1-6 haloalkyl, C1-6 haloalkoxy, C3-8 cycloalkyl, 3-8 membered heterocyclyl, C6-10 aryl or 5-8 membered heteroaryl, wherein each of the C1-6 alkyl, C1-6 alkoxy, C1-6 alkylamino, C1-6 haloalkyl, C1-6 haloalkoxy, C3-8 cycloalkyl, 3-8 membered heterocyclyl, C6-10 aryl or 5-8 membered heteroaryl is independently unsubstituted or substituted with 1, 2 or 3 Rw;
or R7, R8 and the carbon atom to which they are attached form a C3-8 carbocyclic ring or a 3-8 membered heterocyclic ring, wherein each of the C3-8 carbocyclic ring and 3-8 membered heterocyclic ring is independently unsubstituted or substituted with 1, 2 or 3 Rw;
each Rx, Ry, and Rw is independently deuterium, F, Cl, Br, I, CN, NO2, OH, NH2, —SH, ═O, —C (═O) OH, —C(═O)NH2, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 alkylamino or C1-6 haloalkoxy;
wherein, the compound does not include

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