US 12,083,088 B2
Substituted esters containing polyols and saccharides for treating hepatotoxicity and fatty liver diseases
Oliver Yoa-Pu Hu, Taipei (TW); Tung-Yuan Shih, Taipei (TW); Cheng-Huei Hsiong, Taipei (TW); and Hsin-Tien Ho, Taipei (TW)
Assigned to SINEW PHARMA INC., Taipei (TW)
Filed by SINEW PHARMA INC., Taipei (TW)
Filed on Mar. 3, 2022, as Appl. No. 17/686,013.
Application 17/686,013 is a division of application No. 16/573,506, filed on Sep. 17, 2019, granted, now 11,285,123.
Application 16/573,506 is a division of application No. 15/564,526, granted, now 10,456,371, issued on Oct. 29, 2019, previously published as PCT/CN2016/100187, filed on Sep. 26, 2016.
Claims priority of provisional application 62/222,959, filed on Sep. 24, 2015.
Claims priority of provisional application 62/257,697, filed on Nov. 19, 2015.
Claims priority of application No. PCT/CN2016/078039 (WO), filed on Mar. 31, 2016.
Prior Publication US 2022/0265587 A1, Aug. 25, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/225 (2006.01); A61K 31/194 (2006.01); A61K 45/06 (2006.01); A61K 47/26 (2006.01); A61P 1/16 (2006.01); C07C 51/215 (2006.01); C07C 69/42 (2006.01); C07C 69/63 (2006.01); C07D 319/06 (2006.01); C07D 407/12 (2006.01); C07H 13/04 (2006.01); A61K 31/047 (2006.01); A61K 31/428 (2006.01); A61K 31/7004 (2006.01)
CPC A61K 31/194 (2013.01) [A61K 45/06 (2013.01); A61K 47/26 (2013.01); A61P 1/16 (2018.01); C07C 51/215 (2013.01); C07C 69/42 (2013.01); C07D 319/06 (2013.01); C07D 407/12 (2013.01); C07H 13/04 (2013.01); A61K 31/047 (2013.01); A61K 31/428 (2013.01); A61K 31/7004 (2013.01); A61K 2300/00 (2013.01)] 81 Claims
 
1. A compound represented by Formula (II):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt or stereoisomer thereof,
wherein:
(i) R1 is hydrogen;
R2 is a saccharide group represented by Formula (Ia):

OG Complex Work Unit Chemistry
each X is independently —C(═O)—; and
m is 3, 4, 5, 6, 7, 8, 9, or 10; or
(ii) R1 is a C3-C18 alkyl polyol represented by Formula A:
CH2(CHOH)nCH2OH   Formula A
or a stereoisomer thereof,
wherein:
n is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16; and
R2 is a saccharide group represented by Formula (Ia):

OG Complex Work Unit Chemistry
each X is independently —C(═O)—; and
m is 3, 4, 5, 6, 7, 8, 9, or 10; or
(iii) R1 is a saccharide group represented by Formula (Ia):

OG Complex Work Unit Chemistry
R2 is a saccharide group represented by Formula (Ia):

OG Complex Work Unit Chemistry
each X is independently —C(═O)—; and
m is 3, 4, 5, 6, 7, 8, 9, or 10; or
(iv) R1 is hydrogen;
R2 is a Co-Cis alkyl polyol represented by Formula A:
CH2(CHOH)nCH2OH   Formula A
or a stereoisomer thereof,
wherein:
n is 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16;
each X is independently —C(═O)—; and
m is 3, 4, 5, 6, 7, 8, 9, or 10.
 
12. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and the compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof.