Compounds, compositions, methods of using, and methods for preparing compounds

Patent metadata

Field	Value
Publication number	US-12377069-B2
Application number	US-202318494818-A
Country	US
Kind code	B2
Filing date	Oct 26, 2023
Priority date	May 15, 2018
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

In some embodiments of the invention, inventive compounds (e.g., Formula (I), (IA), (II), and (III), and urolithin derivatives) are disclosed. Other embodiments include compositions (e.g., pharmaceutical compositions) comprising the inventive compound. Still other embodiments of the invention include compositions (e.g., pharmaceutical compositions) for treating, for example, certain diseases using the inventive compounds. Some embodiments include methods of using the inventive compound (e.g., in compositions or in pharmaceutical compositions) for administering and treating (e.g., diseases). Further embodiments include methods for making the inventive compounds. Additional embodiments of the invention are also discussed herein.

First claim

What is claimed is:

1. A pharmaceutical composition comprising a compound selected from

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

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

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 X 1 and X 2 is a single bond or a double bond;
the bond between X 7 and X 8 is a single bond or a double bond;
X 1 , X 2 , X 7 , and X 8 are the same or different and each can be independently selected from CH, CH 2 , O, S, C—NH 2 , C—N═CH 2 , C(H)(NH 2 ), C═O, C═N—NH 2 , C═NH, C═N— cycloalkyl, C═N—S(O) H, C═NC(EtOH) 3 , C═NCH(EtOH) 2 , C═NEtOH, C(CH 3 )(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, CH 2 , C—NH 2 , C—N═CH 2 , C(H)(NH 2 ), C═N—NH 2 , C═NH, C═N-cycloalkyl, C═N—S(O) H, C═NC(EtOH) 3 , C═NCH(EtOH) 2 , C═NEtOH, C(CH 3 )(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), —COCH 3 , carboxy (—CO 2 H), ethynyl (—CCH), cyano (—CN), sulfo (—SO 3 H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl;
X 1 and X 2 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), —COCH 3 , carboxy (—CO 2 H), ethynyl (—CCH), cyano (—CN), sulfo (—SO 3 H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl;
X 7 and X 8 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), —COCH 3 , carboxy (—CO 2 H), ethynyl (—CCH), cyano (—CN), sulfo (—SO 3 H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl;
R 1 , R 2 , R 3 , R 4 , and R 5 are the same or different and each is independently selected from H, OH, halogen, methanoyl (—COH), —OCF 3 , —COCH 3 , carbonyl, carboxy (—CO 2 H), ethynyl (—CCH), cyano (—CN), amine, —NO 2 , sulfo (—SO 3 H), C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, methyl, ethyl, perfluorinated methyl, perfluorinated ethyl, cycloalkyl, or heterocyclyl, which H, OH, methanoyl (—COH), —COCH 3 , carbonyl, carboxy (—CO 2 H), ethynyl (—CCH), sulfo (—SO 3 H), C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, methyl, ethyl, cycloalkyl, or heterocyclyl are optionally substituted with one or more of halogen, hydroxy (—OH), methanoyl (—COH), —COCH 3 , carboxy (—CO 2 H), ethynyl (—CCH), cyano (—CN), sulfo (—SO 3 H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl;
X 3 , X 4 , X 5 , and X 6 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), —COCH 3 , carboxy (—CO 2 H), ethynyl (—CCH), cyano (—CN), sulfo (—SO 3 H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl, and with the proviso that X 1 and X 2 do not form —O—(CO)— or —(CO)—O— and

with the proviso that the compound is not

or

2. The pharmaceutical composition of claim 1 , wherein X 1 , X 2 , X 7 , and X 8 are the same or different and each can be independently selected from CH 2 , O, C(H)(NH 2 ), C═O, C═N—NH 2 , C═NH, C═N-cycloalkyl, C═N-adamantane, C═NC(EtOH) 3 , C═NCH(EtOH) 2 , C═NEtOH, C(CH 3 )(OH), or C(H)(cycloalkyl).

3. The pharmaceutical composition of claim 1 , wherein X 1 and X 2 are the same, X 7 and X 8 is the same, X 1 and X 7 is the same, X 2 and X 8 is the same, or a combination thereof.

4. The pharmaceutical composition of claim 1 , wherein X 3 , X 4 , X 5 , and X 6 are the same or different and each is independently selected from CH or N.

5. The pharmaceutical composition of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 are the same or different and each is independently selected from H, OH, halogen, methanoyl (—COH), —OCF 3 , —COCH 3 , carbonyl, carboxy (—CO 2 H), cyano (—CN), amine, —NO 2 , methoxy, ethoxy, methyl, ethyl, perfluorinated methyl, perfluorinated ethyl, cycloalkyl, bicycloalkyl, heterocyclyl, or imidazolyl.

6. The pharmaceutical composition of claim 1 , wherein the compound is selected from Formula (IA)

salts of formula (IA), optical isomers of formula (IA), geometric isomers of formula (IA), and salts of isomers of formula (IA).

7. The pharmaceutical composition of claim 1 , wherein X 1 and X 2 are the same or different and each is independently selected from CH 2 , O, C(H)(NH 2 ), C═O, C═N—NH 2 , C═NH, C═N-cycloalkyl, C═NC(EtOH) 3 , C═NCH(EtOH) 2 , C═NEtOH, C(CH 3 )(OH), or C(H)(cycloalkyl), which CH 2 , C(H)(NH 2 ), C═N—NH 2 , C═NH, C═N-cycloalkyl, C═NC(EtOH) 3 , C═NCH(EtOH) 2 , C═NEtOH, C(CH 3 )(OH), or C(H)(cycloalkyl), are optionally substituted with one or more of halogen, hydroxy (—OH), methanoyl (—COH), —COCH 3 , carboxy (—CO 2 H), ethynyl (—CCH), cyano (—CN), sulfo (—SO 3 H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl.

8. The pharmaceutical composition of claim 1 , wherein X 1 and X 2 are the same or different and each is independently selected from CH 2 , O, C═O, C═NH, C—N— cycloalkyl, C═NC(EtOH) 3 , C═NCH(EtOH) 2 , C═NEtOH, C(CH 3 )(OH), or C(H)(cycloalkyl).

9. The pharmaceutical composition of claim 1 , wherein R 1 and R 2 are the same or different and each is independently selected from H, OH, halogen, methanoyl (—COH), —OCF 3 , —COCH 3 , carbonyl, carboxy (—CO 2 H), ethynyl (—CCH), cyano (—CN), amine, —NO 2 , sulfo (—SO 3 H), C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, methyl, ethyl, perfluorinated methyl, perfluorinated ethyl, which H, OH, methanoyl (—COH), —COCH 3 , carbonyl, carboxy (—CO 2 H), ethynyl (—CCH), sulfo (—SO 3 H), C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, methyl, or ethyl, are optionally substituted with one or more of halogen, hydroxy (—OH), methanoyl (—COH), —COCH 3 , carboxy (—CO 2 H), ethynyl (—CCH), cyano (—CN), sulfo (—SO 3 H), methyl, ethyl, perfluorinated methyl, or perfluorinated ethyl.

10. The pharmaceutical composition of claim 1 , wherein R 1 and R 2 are the same or different and each is independently selected from H, OH, halogen, methanoyl (—COH), —OCF 3 , —COCH 3 , carbonyl, carboxy (—CO 2 H), cyano (—CN), amine, —NO 2 , methox

Assignees

• Univ Louisville Res Found Inc
• The Inst For Stem Cell Biology And Regenerative Medicine Instem

Inventors

• Jala Venkatakrishna Rao
• Bodduluri Haribabu
• Singh Rajbir
• Vemula Praveen Kumar
• Chandrashekharappa Sandeep
• Hiwale Ankita Arun

Classifications

• C07D311/80 Primary

  Dibenzopyrans; Hydrogenated dibenzopyrans · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61P1/00

  Drugs for disorders of the alimentary tract or the digestive system · CPC title

• A61P37/06

  Immunosuppressants, e.g. drugs for graft rejection · CPC title

• A61P1/16

  for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics · CPC title