Prodrugs of azo compounds and their salts

Patent metadata

Field	Value
Publication number	US-2024209010-A1
Application number	US-202218278530-A
Country	US
Kind code	A1
Filing date	Feb 24, 2022
Priority date	Feb 24, 2021
Publication date	Jun 27, 2024
Grant date	—

Abstract

The present invention relates to compounds of formula I and therapeutic use of the same. The present invention also discloses pharmaceutical composition of compounds of formula I and method of treatment using the same.

First claim

1 . A compound of formula I, pharmaceutically acceptable salts or solvates thereof:

wherein; R 1 and R 3 are the same or different and independently selected from hydrogen,

wherein R 2 is selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; R 4 is selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl, —(CH 2 —CH 2 —O) n —, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; where n is from 1-20;
R 5 is selected from hydrogen, —OH, —OR 8 , and

wherein R 9 is selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, amino, alkyl-ester, alkoxy, heterocycloalkoxy, heteroaryloxy, cycloalkoxy, aryloxy, amino acid linked via ester or amide linkage at the point of attachment, —(CH 2 —CH 2 —O) n —, or NR 10 R 11 , where n is from 1-20, R 10 and Ru are the same or different and independently selected from hydrogen or optionally substituted alkyl; R 8 is selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;
R 6 is a phenylene group; wherein the phenylene group is zero to four times substituted by R 7 , wherein R 7 is selected from hydrogen, —OH, —OR 12 ,

wherein R 12 is selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; R 13 is selected from group consisting of optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkyl-ester, amino, alkoxy, heterocycloalkoxy, heteroaryloxy, cycloalkoxy, aryloxy, aminoaryl, or amino acid linked via ester or amide linkage at the point of attachment, —(CH 2 —CH 2 —O) n —, or NR 14 R 15 , where n is from 1-20; where R 14 and R 15 are each independently selected from hydrogen, optionally substituted alkyl, heterocycloalkyl, aryl group; R 16 is selected from optionally substituted alkylene(C 1-6 ) group; with the proviso that all substitutions at R 1 , R 3 , R 5 , R 7 are not hydrogen when R 6 is phenylene; when anyone substitution at R 1 or R 3 is other than hydrogen and R 6 is phenylene, then R 5 and R 7 is not hydrogen; when substitution at R 1 , R 3 , R 7 is hydrogen then R 5 is not —OH; when substitution at R 1 , R 3 , R 5 is hydrogen and R 6 is phenylene then single R 7 substitution on phenylene is not —OH or —O-(alkyl 1-3 ) at either ortho or para position; when substitution at R 1 , R 3 is hydrogen, R 5 is —OH and R 6 is phenylene then R 7 substitution on phenylene is not —OH para position.

2 . A compound of formula I-A, pharmaceutically acceptable salts or solvates thereof:

wherein; R 1 and R 3 are the same or different and independently selected from hydrogen,

wherein R 2 is selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; R 4 is selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl, —(CH 2 —CH 2 —O) n —, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl, where n is from 1-20; R 17 is selected from optionally substituted linear or branched alkylene group, wherein alkylene is optionally substituted with amino, alkylamino and dialkylamino group; R 18 is selected from NH 2 , —NR 20 R 21 , wherein R 20 and R 21 are each independently selected from hydrogen, optionally substituted alkyl, —C(O)—R 22 , wherein R 22 is selected from optionally substituted alkyl, cycloalkyl, heterocycloalkyl, heteroaryl, and aryl group;
R 5 is selected from hydrogen, —OH, —OR 8 , and

wherein R 9 is selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, amino, alkyl-ester, alkoxy, heterocycloalkoxy, heteroaryloxy, cycloalkoxy, aryloxy, amino acid linked via ester or amide linkage at the point of attachment, —(CH 2 —CH 2 —O) n —, or NR 10 R 11 , where n is from 1-20; R 10 and R 11 are the same or different and independently selected from hydrogen or optionally substituted alkyl, cycloalkyl, aryl, heterocycloalkyl, and heteroaryl group; R 8 is selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;
R 6 is a phenylene group, wherein the phenylene group is zero to four times substituted by R 7 , wherein R 7 is selected from hydrogen, —OH, —OR 12 ,

and—R 19 ; wherein R 12 is selected from the group consisting of optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; R 13 is selected from group consisting of optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkyl-ester, amino, alkoxy, heterocycloalkoxy, heteroaryloxy, cycloalkoxy, aryloxy, aminoaryl, or amino acid linked via ester or amide linkage at the point of attachment, —(CH 2 —CH 2 —O) n —, or NR 14 R 15 , where n is from 1-20; R 14 and R 15 are each independently selected from hydrogen, optionally substituted alkyl, heterocycloalkyl, aryl group; R 16 selected from optionally substituted alkylene (C1-6) group; R 19 is selected from —O—R 23 —O—C(O)—R 24 , —O—C(O)—R 23 —R 27 , and —O—R 23 — R 28 , wherein R 23 is optionally substituted linear or branched alkylene; R 24 is selected from optionally substituted alkoxy, cycloalkoxy, heterocycloalkoxy, heteroaryloxy, aryloxy group and —N(R 25 R 26 ), wherein R 25 , R 26 are each independently selected from hydrogen, optionally substituted alkyl and aryl, wherein alkyl and aryl are optionally substituted with OH, SH, F, Cl, Br, I, and optionally substituted hydroxyalkyl, amino group, or R 25 and R 26 is taken together to form an optionally substituted heterocycloalkyl ring, wherein the heterocycloalkyl ring is optionally substituted with alkyl, hydroxyalkyl, —OH, —SH, F, Cl, Br, I, and optionally substituted amino group;
R 27 is selected from optionally substituted alkyl, cycloalkyl, heterocycloalkyl, heteroaryl, aryl and —N(R 25 R 26 ) group;
R 28 is selected from optionally substituted alkyl, cycloalkyl, heterocycloalkyl, heteroaryl, and aryl group; wherein heterocycloalkyl, heteroaryl in R 28 is optionally substituted with alkyl, hydroxyalkyl group, OH, SH, F, Cl, Br, I, and optionally substituted, amino and oxo group;
R 29 and R 30 are each independently selected from hydrogen, and —R 23 —O—C(O)—O—R 31 ; wherein R 31 is selected from optionally substituted alkyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl group; with the proviso that all substitutions at R 1 , R 3 , R 5 , R 7 are not hydrogen when R 6 is phenylene; when anyone substitution at R 1 or R 3 is other than hydrogen and R 6 is phenylene, then R 5 and R 7 is not hydrogen; when substitution at R 1 , R 3 , R 7 is hydrogen then R 5 is not —OH; when substitution at R 1 , R 3 , R 5 is hydrogen and R 6 is phenylene then single R 7 substitu

Assignees

• Kashiv Biosciences Llc

Inventors

• Purohit Parva Yogeshchandra
• Sangle Ganesh Vishwanath
• Unadkat Vishal Bharatbhai
• Goswami Vishalgiri Gunvantgiri
• Pandya Heta Nishil
• Mehta Chirag Chimanlal

Classifications

• C07D487/10

  Spiro-condensed systems · CPC title

• C07D471/10

  Spiro-condensed systems · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D213/85

  in position 3 · CPC title