Substituted imidazo ring systems and methods

Patent metadata

Field	Value
Publication number	US-9328110-B2
Application number	US-201414205114-A
Country	US
Kind code	B2
Filing date	Mar 11, 2014
Priority date	Nov 25, 2003
Publication date	May 3, 2016
Grant date	May 3, 2016

Abstract

Imidazo ring systems substituted at the 1-position, pharmaceutical compositions containing the compounds, intermediates, methods of making the compounds, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

First claim

What is claimed is:

1. A compound of the Formula (I-1):

wherein:
X is alkylene optionally interrupted by one or more —O— groups;
Z is —C(O)—;
R 1-1 is selected from the group consisting of:
hydrogen,
alkyl,
aryl,
alkylene-aryl,
heteroaryl,
alkylene-heteroaryl, and
alkyl, aryl, alkylene-aryl, heteroaryl, or alkylene-heteroaryl substituted by one or more substituents selected from the group consisting of:
halogen,
cyano,
nitro,
alkoxy,
dialkylamino,
alkylthio,
haloalkyl,
haloalkoxy, and
alkyl;

R 2 is selected from the group consisting of:
hydrogen,
alkyl,
alkenyl,
alkylene-Y-alkyl,
alkyene-Y-alkenyl, and
alkyl or alkenyl substituted by one or more substituents selected from the group consisting of hydroxyl and halogen;

R A and R B are each independently selected from the group consisting of:
hydrogen,
alkyl,
alkenyl,
alkoxy, and
alkylthio;

Y is selected from the group consisting of —O— and —S(O) 0-2 — or a pharmaceutically acceptable salt thereof.

2. The compound or salt of claim 1 wherein R 1-1 is alkyl; and R 2 is selected from the group consisting of alkyl, alkylene-Y-alkyl, and alkyl substituted by hydroxyl.

3. The compound or salt of claim 1 wherein Y is —O—.

4. The compound or salt of claim 1 wherein:
R 2 is selected from the group consisting of hydrogen, alkyl, alkylene-O-alkyl, and alkyl substituted by one or more substituents selected from the group consisting of hydroxyl and halogen.

5. The compound or salt of claim 4 wherein R 1-1 is selected from the group consisting of alkyl, aryl, and alkylene-aryl.

6. The compound or salt of claim 4 wherein R 1-1 is alkyl.

7. The compound or salt of claim 4 wherein R 1-1 is C 1-8 alkyl.

8. The compound or salt of claim 4 wherein R 1-1 is —(CH 2 ) 1-7 CH 3 .

9. The compound or salt of claim 1 , which is
5-(4-Amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)pentan-2-one.

Assignees

• 3M Innovative Properties Co

Inventors

• Krepski Larry R
• Dellaria Jr Joseph F
• Duffy Daniel E
• Radmer Matthew R
• Amos David T

Classifications

• A61P37/06

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

• A61P37/08

  Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14) · CPC title

• A61P7/00

  Drugs for disorders of the blood or the extracellular fluid · CPC title

• A61P37/04

  Immunostimulants · CPC title

• A61P39/02

  Antidotes · CPC title