US 12,410,124 B2
Carbamate-substituted styryl sulfone compounds, preparation method and use thereof
Xinan Lv, Beijing (CN); Junyi Liu, Beijing (CN); Shouxin Zhou, Beijing (CN); Xiang Ao, Beijing (CN); and Zhizhong Ma, Beijing (CN)
Assigned to Huaxiashengsheng Pharmaceutical Beijing Co., Ltd., Beijing (CN)
Appl. No. 17/628,017
Filed by HUAXIASHENGSHENG PHARMACEUTICAL BEIJING CO., LTD., Bejing (CN)
PCT Filed Jul. 18, 2019, PCT No. PCT/CN2019/096502
§ 371(c)(1), (2) Date Jan. 18, 2022,
PCT Pub. No. WO2021/007840, PCT Pub. Date Jan. 21, 2021.
Prior Publication US 2022/0267263 A1, Aug. 25, 2022
Int. Cl. C07C 317/28 (2006.01); C07D 207/08 (2006.01); C07D 213/643 (2006.01); C07D 265/30 (2006.01); C07D 307/54 (2006.01); C07D 333/36 (2006.01)
CPC C07C 317/28 (2013.01) [C07D 207/08 (2013.01); C07D 213/643 (2013.01); C07D 265/30 (2013.01); C07D 307/54 (2013.01); C07D 333/36 (2013.01)] 17 Claims
 
1. A compound of general formula I or pharmaceutically acceptable salts thereof:

OG Complex Work Unit Chemistry
wherein,
at least one of R1 and R2 is independently selected from: carbamoyloxy unsubstituted or substituted by one or two R3; the other one of R1 and R2 is independently selected from: carbamoyloxy unsubstituted or substituted by one or two R3, C1-6 alkoxy unsubstituted or substituted by one to six halogen, —N(R4)2 or —OR5; C1-6 alkylacyloxy or C7-10 arylacyloxy unsubstituted or substituted by one to six halogen, —N(R4)2 or —OR5, sulfonyloxy substituted by C1-3 alkyl or C6-8 aryl; —OSi(R6)3, and —OH;
W is C1-6 alkylene or C2-6 alkenylene unsubstituted or substituted by one to three halogen, nitro, C1-6 alkyl, —N(R4)2 or —OR5;
each R is independently selected from: halogen; nitro; —OR7; —N(R4)2; and C1-6 alkyl, C6-10 aryl or C5-9 heteroaryl, unsubstituted or substituted by one to six halogen, nitro, —N(R4)2 or —OR5;
n is an integer from 0 to 5;
wherein,
each R3 is independently selected from: C1-6 saturated alkyl, C2-4 alkenyl, C2-4 alkynyl, C6-10 aryl, C5-9 heteroaryl, C1-6 alkylacyl or C7-10 arylacyl, unsubstituted or substituted by one to six halogen, nitro, —N(R4)2 or —OR5; sulfonyl substituted by C1-3 alkyl or C6-8 aryl; or two R3 together with the nitrogen atom to which they are attached form a 5- to 7-membered nitrogen-containing saturated heterocyclyl, provided that at least one of R1 and R2 is carbamoyloxy substituted by two R3, the 5- to 7-membered nitrogen-containing saturated heterocyclyl is unsubstituted or substituted by one or two R6;
each R4 is independently —H or C1-6 saturated alkyl;
each R5 is independently selected from —H, C1-6 saturated alkyl, C2-4 alkenyl, C6-10 aryl, and C5-9 heteroaryl;
each R6 is independently selected from C1-6 alkyl, C1-6 alkoxy and C6-8 aryl, unsubstituted or substituted by one to six halogen;
each R7 is independently selected from H; C1-6 saturated alkyl, C2-4 alkenyl, C2-4 alkynyl, C6-10 aryl, C5-9 heteroaryl, C1-6 alkylacyl or C7-10 arylacyl, unsubstituted or substituted by one to six halogen, N(R4)2 or OR5; sulfonyl substituted by C1-3 alkyl or C6-8 aryl; and Si(R6)3.