US 12,377,069 B2
Compounds, compositions, methods of using, and methods for preparing compounds
Venkatakrishna Rao Jala, Louisville, KY (US); Haribabu Bodduluri, Louisville, KY (US); Rajbir Singh, Louisville, KY (US); Praveen Kumar Vemula, Bangalore (IN); Sandeep Chandrashekharappa, Bangalore (IN); and Ankita Arun Hiwale, Bangalore (IN)
Assigned to UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION, INC., Louisville, KY (US); and THE INSTITUTE FOR STEM CELL BIOLOGY AND REGENERATIVE MEDICINE (INSTEM), Bangalore (IN)
Filed by UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION, INC., Louisville, KY (US); and THE INSTITUTE FOR STEM CELL BIOLOGY AND REGENERATIVE MEDICINE (INSTEM), Bangalore (IN)
Filed on Oct. 26, 2023, as Appl. No. 18/494,818.
Application 18/494,818 is a continuation of application No. 17/053,811, abandoned, previously published as PCT/US2019/032117, filed on May 14, 2019.
Claims priority of provisional application 62/671,737, filed on May 15, 2018.
Prior Publication US 2024/0173288 A1, May 30, 2024
Int. Cl. A61K 31/352 (2006.01); A61P 1/00 (2006.01); A61P 1/16 (2006.01); A61P 35/00 (2006.01); A61P 37/06 (2006.01); C07D 311/80 (2006.01)
CPC A61K 31/352 (2013.01) [A61P 1/00 (2018.01); A61P 1/16 (2018.01); A61P 35/00 (2018.01); A61P 37/06 (2018.01); C07D 311/80 (2013.01)] 19 Claims
OG exemplary drawing
 
1. A pharmaceutical composition comprising a compound selected from

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salts of formula (I), optical isomers of formula (I), geometric isomers of formula (I), salts of isomers of formula (I),

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salts of formula (II), optical isomers of formula (II), geometric isomers of formula (II), salts of isomers of formula (II),

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salts of formula (III), optical isomers of formula (III), geometric isomers of formula (III), and salts of isomers of formula (III),
wherein
the bond between X1 and X2 is a single bond or a double bond;
the bond between X7 and X8 is a single bond or a double bond;
X1, X2, X7, and X8 are the same or different and each can be independently selected from CH, CH2, O, S, C—NH2, C—N═CH2, C(H)(NH2), C═O, C═N—NH2, C═NH, C═N— cycloalkyl, C═N—S(O) H, C═NC(EtOH)3, C═NCH(EtOH)2, C═NEtOH, C(CH3)(OH), N, NH, C— halogen, C(H)(halogen), C-(halogen)2, C-cycloalkyl, C-heterocyclyl, C-aryl, C-heteroaryl, C(H)(cycloalkyl), C(H)(heterocyclyl), C(H)(aryl), or C(H)(heteroaryl), which CH, CH2, C—NH2, C—N═CH2, C(H)(NH2), C═N—NH2, C═NH, C═N-cycloalkyl, C═N—S(O) H, C═NC(EtOH)3, C═NCH(EtOH)2, C═NEtOH, C(CH3)(OH), C(H)(halogen), C-cycloalkyl, C-heterocyclyl, C-aryl, C-heteroaryl, C(H)(cycloalkyl), C(H)(heterocyclyl), C(H)(aryl), or C(H)(heteroaryl), are optionally substituted with one or more of halogen, hydroxy (—OH), methanoyl (—COH), —COCH3, carboxy (—CO2H), ethynyl (—CCH), cyano (—CN), sulfo (—SO3H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl;
X1 and X2 are optionally further cyclized to form a 5 or 6 membered cycloalkyl, 5 or 6 membered heterocyclyl, 5 or 6 membered aryl, or 5 or 6 membered heteroaryl, which 5 or 6 membered cycloalkyl, 5 or 6 membered heterocyclyl, 5 or 6 membered aryl, or 5 or 6 membered heteroaryl are optionally substituted with one or more of halogen, hydroxy (—OH), methanoyl (—COH), —COCH3, carboxy (—CO2H), ethynyl (—CCH), cyano (—CN), sulfo (—SO3H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl;
X7 and X8 are optionally further cyclized to form a 5 or 6 membered cycloalkyl, 5 or 6 membered heterocyclyl, 5 or 6 membered aryl, or 5 or 6 membered heteroaryl, which 5 or 6 membered cycloalkyl, 5 or 6 membered heterocyclyl, 5 or 6 membered aryl, or 5 or 6 membered heteroaryl are optionally substituted with one or more of halogen, hydroxy (—OH), methanoyl (—COH), —COCH3, carboxy (—CO2H), ethynyl (—CCH), cyano (—CN), sulfo (—SO3H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl;
R1, R2, R3, R4, and R5 are the same or different and each is independently selected from H, OH, halogen, methanoyl (—COH), —OCF3, —COCH3, carbonyl, carboxy (—CO2H), ethynyl (—CCH), cyano (—CN), amine, —NO2, sulfo (—SO3H), C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C3 alkoxy, methyl, ethyl, perfluorinated methyl, perfluorinated ethyl, cycloalkyl, or heterocyclyl, which H, OH, methanoyl (—COH), —COCH3, carbonyl, carboxy (—CO2H), ethynyl (—CCH), sulfo (—SO3H), C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C3 alkoxy, methyl, ethyl, cycloalkyl, or heterocyclyl are optionally substituted with one or more of halogen, hydroxy (—OH), methanoyl (—COH), —COCH3, carboxy (—CO2H), ethynyl (—CCH), cyano (—CN), sulfo (—SO3H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl;
X3, X4, X5, and X6 are the same or different and each is independently selected from CH or N, which CH is optionally substituted with one or more of halogen, hydroxy (—OH), methanoyl (—COH), —COCH3, carboxy (—CO2H), ethynyl (—CCH), cyano (—CN), sulfo (—SO3H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl, and with the proviso that X1 and X2 do not form —O—(CO)— or —(CO)—O— and
with the proviso that the compound is not

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or

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