Immunopotentiating compounds

• US 8,063,063 B2
• Filed: 03/23/2007
• Issued: 11/22/2011
• Est. Priority Date: 03/23/2006
• Status: Expired due to Fees

• Current Assignee: Novartis Ag
• Original Assignee: Novartis Ag
• Inventors: Sutton, James, Valiante, Nicholas
• Primary Examiner(s): Seaman; D M
• Assistant Examiner(s): Rahmani; Niloofar
• Application Number:
  US12/294,237
• Publication Number:
  US 20090232844A1
• Time in Patent Office: 1,705 Days
• Field of Search: 546/118, 514/303
• US Class Current: 514/303
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 471/14 Ortho-condensed systems

Abstract

The invention provides novel compositions comprising Imidazopyridine compounds. Also provided are methods of administering the compositions in an effective amount to enhance the immune response of a subject. Further provided are novel compositions and methods of administering the compositions in combination with (an)other agent(s).

Claims

1. A compound of Formula (I):

2. The compound of claim 1, wherein R¹ and R² are each, independently, C_1-4 alkyl, wherein the C_1-4 alkyl is optionally substituted by 1, 2, or 3 substituents independently selected from OH and C_1-4 alkoxy.

3. The compound of claim 1, wherein R¹ is methyl and R² is n-propyl.

4. The compound of claim 1, wherein R³ is C_1-6 alkyl optionally substituted by 1, 2 or 3 substituents independently selected from halo, CN, NO₂, C_1-6 haloalkyl, C_6-10 aryl, C_3-14 cycloalkyl, heterocyclyl, OR^a, SR^a, C(═

O)R^b, C(═

O)NR^cR^d, C(═

O)OR^a, C(═

S)NR^cR^d, OC(═

O)R^b, OC(═

O)NR^cR^d, NR^cR^d, NR^cC(═

O)R^b, NR^cC(═

O)OR^a, NR^cS(═

O)₂R^b, S(═

O)R^b, S(═

O)NR^cR^d, S(═

O)₂OH, S(═

O)₂R^b, and S(═

O)₂NR^cR^d.

5. The compound of claim 1, wherein R³ is C_1-6 alkyl optionally substituted by 1 or 2 OH.

6. The compound of claim 1 wherein:

R⁴ and R⁵ are each, independently, selected from H, C_1-6 alkyl, C_6-10 aryl, —

NR⁷R⁸, and —

OR⁹, wherein each of the C_1-6 alkyl and C_6-10 aryl is optionally substituted by 1, 2 or 3 substituents independently selected from halo, OH, CN, NO₂, C_1-6 alkyl, C_1-6 haloalkyl, C_6-10 aryl, C_3-14 cycloalkyl, heterocyclyl, C_6-10 aryloxy, C_1-6 alkoxy and C_1-6 haloalkoxy;

R⁷ and R⁸ are each, independently, selected from H, C_1-6 alkyl, C_1-6 alkoxy, C_1-6 alkoxy-C_1-6 alkyl, C_6-10 aryl, C_6-10 aryl-C_1-6 alkyl, C_6-10 aryloxy-C_1-6 alkyl;

or R⁷ and R⁸ together with the N atom to which they are attached form a heterocyclyl group optionally substituted by 1, 2, 3, 4 or 5 substituents independently selected from halo, OH, CN, NO₂, C_1-6 alkyl, C_1-6 haloalkyl, C_6-10 aryloxy, C_1-6 alkoxy and C_1-6 haloalkoxy; and

R⁹ is C_1-6 alkyl, C_1-6 alkoxy-C_1-6 alkyl, C_6-10 aryl, C_6-10 aryl-C_1-6 alkyl, or C_6-10 aryloxy-C_1-6 alkyl.

7. The compound of claim 1 wherein:

R⁴ and R⁵ are each, independently, selected from H, C_6-10 aryl, azepanyl, morpholino, piperazinyl, piperidinyl, pyrrolidinyl, azetidinyl, aziridinyl, —

NHR⁸, and —

OR⁹; and

R⁸ and R⁹ are each, independently, selected from C_1-6 alkyl, C_1-6 alkoxy-C_1-6 alkyl, C_6-10 aryl, C_6-10 aryl-C_1-6 alkyl and C_6-10 aryloxy-C_1-6 alkyl.

8. The compound of claim 1 wherein:

R¹ is methyl;

R² is n-propyl;

R³ is C_3-6 alkyl optionally substituted by OH;

one of R⁴ and R⁵ is H and the other is selected from C_6-10 aryl, azepanyl, piperidinyl, pyrrolidinyl, azetidinyl, aziridinyl, —

NHR⁸, and —

OR⁹; and

R⁸ and R⁹ are each, independently, C_1-6 alkoxy-C_1-6 alkyl.

9. A compound of claim 1 wherein the compound is selected from the group consisting of:

10. A pharmaceutical composition, comprising:

the compound of claim 1 and a pharmaceutically acceptable excipient.