Carbon monoxide releasing molecules and associated methods

Patent metadata

Field	Value
Publication number	US-9840488-B2
Application number	US-201615007033-A
Country	US
Kind code	B2
Filing date	Jan 26, 2016
Priority date	Jan 26, 2015
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

The present disclosure relates to carbon monoxide releasing molecules (“CORMs”), and methods of synthesizing and applying the molecules. More specifically, this disclosure relates to structurally tunable CORMS, compounds containing CORMS (and salts thereof). An exemplary compound includes:

First claim

What is claimed is:

1. A compound, or salt thereof, comprising the formula:

wherein:
Y is a member selected from the group consisting of O or S;
X is a member selected from the group consisting of O or S;
R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 are each a member selected from the group consisting of —H, —COOH, —CSOH, —COOR′, —CONH 2 , —CONHR′, CON(R′) 2 , —COR′, —F, —Cl, —Br, —I, —CN, —NO 2 , —OH, —OR′, —SH, —SR′, —O—CO—R′, —NH 2 , —NHR′, —NR 2 ′, —NH(R′) 2 , —NH—CO—R′, —NR′—CO—R′, —SO 3 R′, —OSO 2 R′, —C 5-15 aryl, —C 1-12 alkyl, —C 2-12 alkenyl, C 2-12 alkynyl, C 1-12 alkyl-C 5-15 aryl, C 2-12 alkenyl-C 5-15 aryl, an amino acid, an aminoglycoside, a carbohydrate, and a heterocycle containing O, N, or S;
wherein the —C 5-15 aryl is optionally substituted with —COOH, —CSOH, —COOR′, —CONH 2 , —CONHR′, CON(R′) 2 , —COR′, —F, —Cl, —Br, —I, —CN, —NO 2 , —OH, —OR′, —SH, —SR′, —O—CO—R′, —NH 2 , —NHR′, —NR 2 ′, —NH(R′), —NH—CO—R′, —NR′—CO—R′, —SO 3 R′, or —OSO 2 R′;
wherein the —C 1-12 alkyl, the —C 2-12 alkenyl, the C 2-12 alkynyl, the C 1-12 alkyl-C 5-15 aryl, the C 2-12 alkenyl-C 5-15 aryl, or the heterocycle is optionally substituted with —COOH, —CSOH, —COOR′, —CONH 2 , —CONHR′, CON(R′) 2 , —COR′, —F, —Cl, —Br, —I, —CN, —NO 2 , —OH, —OR′, —SH, —SR′, —O—CO—R′, —NH 2 , —NHR′, —NR 2 ′, —NH(R′) 2 , —NH—CO—R′, —NR′—CO—R′, —SO 3 R′, —OSO 2 R′, —P(aryl) 3 , P(alkyl) 3 , or PO 3 2 , or HPO 3 ;
wherein R′ is a member selected from the group consisting of C 5-15 aryl, —C 1-12 alkyl, and —C 2-12 alkenyl; and

R 3 is a member selected from the group consisting of —H, —COOH, —CSOH, —COOR″, —CONH 2 , —CONHR″, CON(R″) 2 , —COR″, —F, —Cl, —Br, —I, —CN, —NO 2 , —OH, —OR″, —SH, —SR″, —O—CO—R″, —NH 2 , —NHR″, —NR 2 ″, —NH(R″) 2 , —NH—CO—R″, —NR″—CO—R″, —SO 3 R″, —OSO 2 R″, —P(aryl) 3 , P(alkyl) 3 , PO 3 2 , HPO 3 , C 5-15 aryl, C 1-12 alkyl, —C 2-12 alkenyl, C 2-12 alkynyl, C 1-12 alkyl-C 5-15 aryl, C 2-12 alkenyl-C 5-15 aryl, amino acids, aminoglycosides, carbohydrates, or heterocycles containing O, N, or S;
wherein the C 5-15 aryl, the C 1-12 alkyl, the —C 2-12 alkenyl, the C 2-12 alkynyl, the C 1-12 alkyl-C 5-15 aryl, the C 2-12 alkenyl-C 5-15 aryl, or the heterocycle is optionally substituted with —COOH, —CSOH, —COOR″, —CONH 2 , —CONHR″, CON(R″) 2 , —COR″, —F, —Cl, —Br, —I, —CN, —NO 2 , —OH, —OR″, —SH, —SR″, —O—CO—R″, —NH 2 , —NHR″, —NR 2 ′, —NH(R″) 2 , —NH—CO—R″, —NR″—CO—R″, —SO 3 R″, —OSO 2 R″, —P(aryl) 3 , P(alkyl) 3 , PO 3 2 , or HPO 3 ;
wherein R″ is a member selected from the group consisting of C 5-15 aryl, —C 1-12 alkyl, —C 2-12 alkenyl, and C 2-12 alkynyl, each of which is optionally unsubstituted or substituted with phosphonium; and

R 9 is —H or —COR″″,
wherein R″″ is a member selected from the group consisting of C 5-15 aryl, —C 1-12 alkyl, —C 2-12 alkenyl, and C 2-12 alkynyl.

2. The compound of claim 1 , wherein R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 are the same.

3. The compound of claim 1 , wherein the compound is:

4. The compound of claim 1 , wherein the compound is:

5. The compound of claim 1 , wherein the compound is:

6. The compound of claim 1 , wherein the compound is:

7. The compound of claim 1 , wherein the compound is:

8. The compound of claim 1 , wherein the compound is:

9. The compound of claim 1 , wherein the compound is:

10. The compound of claim 1 , wherein the compound is:

11. The compound of claim 1 , wherein the compound is:

12. The compound of claim 1 , wherein the compound is:

13. A composition, comprising the compound of claim 1 .

14. The composition of claim 13 , further comprising a pharmaceutically acceptable carrier.

Assignees

• Berreau Lisa M
• Anderson Stacey N
• Univ Utah State

Inventors

• Berreau Lisa M
• Anderson Stacey N

Classifications

• C07D409/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D311/92 Primary

  Naphthopyrans; Hydrogenated naphthopyrans · CPC title

• C07F9/65522

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title