Compositions and methods for treating diseases and conditions

Patent metadata

Field	Value
Publication number	US-10487076-B2
Application number	US-201515533978-A
Country	US
Kind code	B2
Filing date	Dec 10, 2015
Priority date	Dec 10, 2014
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

Abstract

A compound of Formula II, or a salt, ester, solvate, hydrate or prodrug thereof:

where:

X 1 is a branched or unbranched C 1-10 alkyl, (CH 2 ) s —NH—(CH 2 ) t , (CH 2 ) s —O—(CH 2 ) t , or (CH 2 ) s —C(NH 2 )—(CH 2 ) v —NH—(CH 2 ) t , where s, t and v are each, independently an integer from 1 to 5;

A and B are each, independently, C 6-10 aryl, C 6-10 aryl-C 1-6 alkyl, C 3-9 heteroaryl, or C 3-9 heteroaryl-C 1-6 alkyl, each optionally substituted with 1, 2 or 3 independently selected R g groups;

C and D are each, independently, C 3-7 cycloalkyl, C 3-7 cycloalkyl-C 1-6 alkyl, C 3-7 heterocycloalkyl, C 3-7 heterocycloalkyl-C 1-6 alkyl, C 6-10 aryl, C 6-10 aryl-C 1-6 alkyl, C 3-9 heteroaryl, or C 3-9 heteroaryl-C 1-6 alkyl, each optionally substituted with 1, 2 or 3 independently selected R g groups;

each R g is, independently, halogen, C 1-6 alkyl, C 1-6 haloalkyl, hydroxyl, C 1-6 alkoxy, C 1-6 haloalkoxy, amino, C 1-6 alkylamino, or di-C 1-6 alkylamino; and

n 1 and p 1 are each, independently, integers from 1 to 10.

First claim

What is claimed is:

1. A compound, or a salt, ester, solvate, hydrate or prodrug thereof, having a structure of:

wherein X 1 is a branched or unbranched C 1-10 alkyl, (CH 2 ) s —NH—(CH 2 ) t , (CH 2 ) s , —O—(CH 2 ) t , or (CH 2 ) s —C(NH 2 )—(CH 2 ) v —NH—(CH 2 ) t , wherein s, t and v are each, independently an integer from 1 to 5;
n 1 and p 1 are each, independently, integers from 1 to 10;
R 20 —R 33 are each independently hydrogen, halogen, or C 1-6 haloalkyl, provided at least one of R 20 —R 33 is halogen.

2. The compound of claim 1 , wherein at least one of R 20 —R 33 is fluorine.

3. The compound of claim 1 , wherein R 25 and R 30 are fluorine.

4. The compound of claim 2 , wherein X 1 is a branched or unbranched C 1-10 alkyl.

5. The compound of claim 1 , wherein R 26 and R 29 are fluorine.

6. The compound of claim 1 , wherein R 21 and R 22 are each fluorine.

7. The compound of claim 1 , wherein X 1 is a branched C 1-10 alkyl.

8. The compound of claim 1 , wherein X 1 is —CH(CH 3 )CH 2 —.

9. A compound, or a salt, ester, solvate, hydrate or prodrug thereof, having a structure of:

10. A compound of structure:

11. A pharmaceutical composition comprising:
a compound of claim 1 ; and
a pharmaceutically acceptable carrier, excipient, or diluent.

12. A pharmaceutical composition comprising:
a compound of claim 9 ; and
a pharmaceutically acceptable carrier, excipient, or diluent.

13. A pharmaceutical composition comprising:
a compound of claim 10 ; and
a pharmaceutically acceptable carrier, excipient, or diluent.

14. A compound of structure:

wherein X 1 is a branched or unbranched C 1-10 alkyl, (CH 2 ) s —NH—(CH 2 ) t ,(CH 2 ) s —O—(CH 2 ) t , or (CH 2 ) s —C(NH 2 )—(CH 2 ) v —NH—(CH 2 ) t , where s, t and v are each, independently an integer from 1 to 5;
n 1 and p 1 are each, independently, integers from 1 to 10;
R 20 —R 33 are each independently hydrogen, halogen, or C 1-6 haloalkyl, provided at least one of R 20 —R 33 is halogen.

Assignees

• Univ Of Pittsburgh—Of The Commonwealth System Of Higher Education
• Us Gov Veterans Affairs

Inventors

• Chen Beibei
• Mallampalli Rama K

Classifications

• C07D239/30

  Halogen atoms or nitro radicals · CPC title

• A61P11/08

  Bronchodilators · CPC title

• A61P11/00

  Drugs for disorders of the respiratory system · CPC title

• A61K31/506

  not condensed and containing further heterocyclic rings · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title