US 11,718,636 B2
Glucosamine derivatives for the prevention or treatment of joint disorders
Xianqi Kong, Dollard-des-Ormeaux (CA); Jiasheng Lu, Shanghai (CN); Jiamin Gu, Suzhou (CN); Xiang Ji, Suzhou (CN); Daiqiang Hu, Suzhou (CN); Xiuchun Zhang, Suzhou (CN); Xinyong Lv, Suzhou (CN); Jinchao Ai, Suzhou (CN); Dongdong Wu, Suzhou (CN); Lin Wang, Suzhou (CN); Dongqing Zhu, Suzhou (CN); and Xiaolin He, Suzhou (CN)
Assigned to RISEN (SUZHOU) PHARMA TECH CO., LTD., Suzhou (CN)
Appl. No. 16/954,491
Filed by RISEN (SUZHOU) PHARMA TECH CO., LTD., Jiangsu (CN)
PCT Filed Dec. 17, 2018, PCT No. PCT/CA2018/051608
§ 371(c)(1), (2) Date Jun. 16, 2020,
PCT Pub. No. WO2019/119117, PCT Pub. Date Jun. 27, 2019.
Claims priority of provisional application 62/621,987, filed on Jan. 25, 2018.
Claims priority of application No. 201711364533.8 (CN), filed on Dec. 18, 2017.
Prior Publication US 2021/0079033 A1, Mar. 18, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07H 15/12 (2006.01); A61P 19/02 (2006.01); A61K 9/00 (2006.01); C07H 15/14 (2006.01); C07H 15/18 (2006.01); C07H 15/203 (2006.01); C07H 15/26 (2006.01); C07H 19/01 (2006.01); C07H 19/02 (2006.01); C07J 9/00 (2006.01)
CPC C07H 15/12 (2013.01) [A61K 9/0014 (2013.01); A61K 9/0053 (2013.01); A61P 19/02 (2018.01); C07H 15/14 (2013.01); C07H 15/18 (2013.01); C07H 15/203 (2013.01); C07H 15/26 (2013.01); C07H 19/01 (2013.01); C07H 19/02 (2013.01); C07J 9/00 (2013.01); C07B 2200/05 (2013.01)] 19 Claims
 
1. A compound of Formula (II), or a pharmaceutically acceptable salt or ester thereof:

OG Complex Work Unit Chemistry
where:
R1 is hydrogen, substituted alkyl, or acyl group derived from a carboxylic acid, or a peptide, optionally with a protecting group, a phosphonyl group, or a sulfonyl group;
R2 is hydrogen, acyl, or alkyl;
R3, R4, and R5 are independently hydrogen, substituted or unsubstituted alkyl, aryl, arylalkyl, alkylaryl, cyclic or heterocyclic moiety, or acyl group derived from a carboxylic acid, an amino acid, or a peptide, optionally with a protecting group, a phosphonyl group, or a sulfonyl group, provided that R3, R4, and R5 are not all acyl group at the same time, wherein when R5 is acyl group which is a carbonyl group that is attached through its carbon atom to an alkyl group, the alkyl group is methyl, ethyl, propyl, butyl, hexyl, isopropyl, tert-butyl, sec-butyl, isobutyl, cyclopropyl, cyclopentyl or cyclohexyl; and
n is an integer from 1 to 6;
provided that R1, R3, R4, and R5 are not all hydrogen at the same time; or
one or more of R1, R3, R4, and R5 are independently selected from alkoxycarbonyl, aryloxycarbonyl, and arylalkoxycarbonyl; or
R3 and R4, taken together with the atoms to which they are attached, form a substituted or unsubstituted heterocyclic ring.