RU2001132570A

RU2001132570A - Urea-substituted imidazoquinolines

Info

Publication number: RU2001132570A
Application number: RU2001132570/04A
Authority: RU
Inventors: Стефен Л. КРУКС; Брайон А. МЕРРИЛЛ; Майкл Дж. РАЙС
Original assignee: 3М Инновейтив Пропертиз Компани
Priority date: 1999-06-10
Filing date: 2000-06-08
Publication date: 2003-12-10

Claims

1. The compound of formula (I)

where R ₁ is alkyl-NR ₃ —CY — NR ₅ —XR ₄ or —alkenyl-NR ₃ —CU — NR ₅ —X — R ₄ ;

Y is = O or = S;

X is a bond, —CO— or –SO ₂ -;

R ₄ is aryl, heteroaryl, heterocyclyl, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents selected from the group consisting of: alkyl; alkenyl; aryl; heteroaryl; heterocyclyl; substituted aryl; substituted heteroaryl; substituted heterocyclyl; O-alkyl; O- (alkyl) _0-1 aryl; O- (alkyl) _0-1- substituted aryl; O- (alkyl) _0-1- heteroaryl; O- (alkyl) _0-1- substituted heteroaryl; O- (alkyl) _0-1- heterocyclyl; O- (alkyl) _0-1 substituted heterocyclyl; COOH; CO-O-alkyl; CO-alkyl; C (O) _0-2 -alkyl; S (O) _0-2 - (alkyl) _0-1 -aryl; S (O) _0-2 - (alkyl) _0-1- substituted aryl; S (O) _0-2 - (alkyl) _0-1- heteroaryl; S (O) _0-2 - (alkyl) _0-1- substituted heteroaryl; S (O) _0-2 - (alkyl) _0-1- heterocyclyl; S (O) _0-2 - (alkyl) _0-1- substituted heterocyclyl; (alkyl) _0-1 —NR ₃ R ₃ ; (alkyl) _0-1 -NR ₃ CO-O-alkyl; (alkyl) _0-1 -NR ₃ CO-alkyl; (alkyl) _0-1 -NR ₃ CO-aryl; (alkyl) _0-1 -NR ₃ CO-substituted aryl; (alkyl) _0-1 -NR ₃ CO-heteroaryl; (alkyl) _0-1 -NR ₃ CO-substituted heteroaryl; N ₃ ; halogen; haloalkyl; haloalkoxyl; CO-haloalkoxyl; NO ₂ ; CN; HE; and SH; and in the case of alkyl, alkenyl or heterocyclyl, a keto group;

provided that, if X is a bond, then R ₄ may also be hydrogen.

R ₂ is selected from the group consisting of hydrogen; alkyl; alkenyl; aryl; substituted aryl; heteroaryl; substituted heteroaryl; alkyl-O-alkyl; alkyl-O-alkenyl; and alkyl or alkenyl substituted with one or more substituents selected from the group consisting of OH; halogen; N (R ₃ ) ₂ ; CO-N (R ₃ ) ₂ ; CO-alkyl C _1-10 ; CO-O-alkyl C _1-10 ; N ₃ ; aryl; substituted aryl; heteroaryl; substituted heteroaryl; heterocyclyl; substituted heterocyclyl; CO-aryl; CO- (substituted aryl); CO heteroaryl; and CO- (substituted heteroaryl);

each of R _{3 is} independently selected from the group consisting of hydrogen and C- ₁₀ alkyl;

R _{5 is} selected from the group consisting of hydrogen and C _1-10 alkyl; or R ₄ and R ₅ together can form a 3-7 membered heterocyclic or substituted heterocyclic ring;

n is a number from 0 to 4, and each R is independently selected from the group consisting of alkyl C _1-10 , alkoxyl C _1-10 , halogen and trifluoromethyl, or a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1, characterized in that X is a bond, and Y is = 0.

3. The compound according to claim 2, characterized in that n = 0.

4. The compound according to claim 2, characterized in that R ₃ is hydrogen.

5. The compound according to claim 2, characterized in that R ₁ is - (CH ₂ ) _2-4 NR ₃ —CO — NR ₅ —R ₄ .

6. The compound according to claim 2, characterized in that R ₄ is selected from the group consisting of hydrogen, alkyl, alkyl-O-alkyl, (alkyl) _0-1 aryl, (alkyl) _0-1 - (substituted aryl) , (alkyl) _0-1- heteroaryl; and (alkyl) _0-1 (substituted heteroaryl).

7. The compound according to claim 2, characterized in that R ₂ is selected from the group consisting of hydrogen; alkyl C _1-4 ; alkyl C _1-4 -O-alkyl C _1-4 .

8. The compound according to claim 2, characterized in that R ₄ is selected from the group consisting of aryl, heteroaryl, heterocycle, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents. selected from the group consisting of alkyl; alkenyl; aryl; heteroaryl; heterocyclyl; substituted aryl; substituted heteroaryl; substituted heterocyclyl; O-alkyl; O- (alkyl) _0-1 aryl; O- (alkyl) _0-1- substituted aryl; O- (alkyl) _0-1- heteroaryl; O- (alkyl) _0-1- substituted heteroaryl; O- (alkyl) _0-1- heterocyclyl; O- (alkyl) _0-1 substituted heterocyclyl; CO-O-alkyl; CO-alkyl; -COOH-; S (O) _0-2 -alkyl; S (O) _0-2 - (alkyl) _0-1 -aryl; S (O) _0-2 - (alkyl) _0-1 -substituted aryl; S (O) _0-2 - (alkyl) _0-1- heteroaryl; S (O) _0-2 - (alkyl) _0-1- substituted heteroaryl; S (O) _0-2 - (alkyl) _0-1- heterocyclyl; S (O) _0-2 - (alkyl) _0-1- substituted heterocyclyl; (alkyl) _0-1 —NR ₃ R ₃ ; (alkyl) _0-1 -NR ₃ CO-O-alkyl; (alkyl) _0-1 -NR ₃ CO-alkyl; (alkyl) _0-1 -NR ₃ CO-aryl; (alkyl) _0-1 -NR ₃ CO-substituted aryl; (alkyl) _0-1 -NR ₃ CO-heteroaryl; (alkyl) _0-1 -NR ₃ CO-substituted heteroaryl; N ₃ ; halogen; haloalkyl; haloalkoxyl; CO-haloalkoxyl; NO ₂ ; CN; HE; SH; and in the case of alkyl, a keto group.

9. The compound according to claim 2, characterized in that R ₄ is phenyl unsubstituted or substituted by one or more substituents selected from the group consisting of methyl, methoxy, halogen, nitrile, nitro, trifluoromethyl and trifluoromethoxyl.

10. The compound according to claim 2, characterized in that R ₄ and R ₅ together form a 3-7-membered substituted or unsubstituted heterocyclic ring.

11. The compound according to claim 2, characterized in that R ₄ and R ₅ collectively form a substituted or unsubstituted pyrrolidine or morpholine ring.

12. The compound according to claim 1, characterized in that X is a bond, and Y is = S.

13. The compound according to p. 12, characterized in that n = 0.

14. The compound according to p. 12, characterized in that R ₃ is hydrogen.

15. The compound according to p. 12, characterized in that R ₁ is - (CH ₂ ) _2-4 -NR ₃ -CO-NR ₅ -R ₄ .

16. The compound according to item 12, wherein R ₄ is selected from the group consisting of hydrogen, alkyl, alkyl-O-alkyl, (alkyl) _0-1 aryl, (alkyl) _0-1 - (substituted aryl) , (alkyl) _0-1 and (alkyl) _0-1 - (substituted heteroaryl).

17. The compound according to item 12, wherein R ₂ is selected from the group consisting of hydrogen; alkyl C _1-4 ; alkyl C ₁ -O-alkyl C _1-4 .

18. The compound according to item 12, wherein R ₄ is selected from the group consisting of aryl, heteroaryl, heterocyclyl, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents selected from the group in which includes alkyl; alkenyl; aryl; heteroaryl; heterocyclyl; substituted aryl; substituted heteroaryl; substituted heterocyclyl; O-alkyl; O- (alkyl) _0-1 aryl; O- (alkyl) _0-1- substituted aryl; O- (alkyl) _0-1- heteroaryl; O- (alkyl) _0-1- substituted heteroaryl; O- (alkyl) _0-1- heterocyclyl; O- (alkyl) _0-1 substituted heterocycle; COOH; CO-O-alkyl; CO-alkyl; S (O) _0-2 -alkyl; S (O) _0-2 - (alkyl) _0-1 -aryl; S (O) _0-2 - (alkyl) _0-1- substituted aryl; S (O) _0-2 - (alkyl) _0-1- heteroaryl; S (O) _0-2 - (alkyl) _0-1- substituted heteroaryl; S (O) _0-2 - (alkyl) _0-1- heterocyclyl; S (O) _0-2 - (alkyl) _0-1- substituted heterocyclyl; (alkyl) _0-1 —NR ₃ R ₃ ; (alkyl) _0-1 -NR ₃ CO-O-alkyl; (alkyl) _0-1 -NR ₃ CO-alkyl; (alkyl) _0-1 -NR ₃ CO-aryl; (alkyl) _0-1 -NR ₃ CO-substituted aryl; (alkyl) _0-1 -NR ₃ CO-heteroaryl; (alkyl) _0-1 -NR ₃ CO-substituted heteroaryl; N ₃ ; halogen; haloalkyl; haloalkoxyl; CO-haloalkoxyl; NO ₂ ; CN; HE; SH; and in the case of alkyl, a keto group.

19. The compound according to item 12, wherein R ₄ is phenyl unsubstituted or substituted by one or more substituents selected from the group consisting of methyl, methoxyl, halogen, nitrile, nitro, trifluoromethyl and trifluoromethoxyl.

20. The compound according to p. 12, characterized in that R ₄ and R ₅ together form a 3-7-membered substituted or unsubstituted heterocyclic ring.

21. The compound according to p. 12, characterized in that R ₄ and R ₅ together form a substituted or unsubstituted pyrrolidine or morpholine ring.

22. The compound according to claim 1, characterized in that X is a bond, and Y is hydrogen.

23. The compound according to claim 1, characterized in that X is = O, and Y is —CO—.

24. The compound according to item 23, wherein n = 0.

25. The compound according to item 23, wherein R ₃ is hydrogen.

26. The compound according to item 23, wherein R ₁ is - (CH ₂ ) _2-4 -NR ₃ -CO-NR ₃ -R ₄ .

27. The compound according to item 23, wherein R ₄ is selected from the group consisting of hydrogen, alkyl, alkyl-O-alkyl, (alkyl) _0-1 aryl, (alkyl) _0-1 - (substituted aryl) , (alkyl) _0-1 and (alkyl) _0-1 - (substituted heteroaryl).

28. The compound according to item 23, wherein R ₂ is selected from the group consisting of hydrogen; alkyl C _1-4 ; alkyl C _1-4 -O-alkyl C _1-4 .

29. The compound according to item 23, wherein R ₄ is selected from the group consisting of aryl, heteroaryl, heterocyclyl, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents selected from the group in which includes alkyl; alkenyl; aryl; heteroaryl; heterocyclyl; substituted aryl; substituted heteroaryl; substituted heterocyclyl; O-alkyl; O- (alkyl) _0-1 aryl; O- (alkyl) _0-1- substituted aryl; O- (alkyl) _0-1- heteroaryl; O- (alkyl) _0-1- substituted heteroaryl; O- (alkyl) _0-1- heterocyclyl; O- (alkyl) _0-1 substituted heterocyclyl; COOH; CO-O-alkyl; CO-alkyl; S (O) _0-2 -alkyl; S (O) _0-2 - (alkyl) _0-1 -aryl; S (O) _0-2 - (alkyl) _0-1- substituted aryl; S (O) _0-2 - (alkyl) _0-1- heteroaryl; S (O) _0-2 - (alkyl) _0-1- substituted heteroaryl; S (O) _0-2 - (alkyl) _0-1- heterocyclyl; S (O) _0-2 - (alkyl) _0-1- substituted heterocyclyl; (alkyl) _0-1 —NR ₃ R ₃ ; (alkyl) _0-1 -NR ₃ CO-O-alkyl; (alkyl) _0-1 -NR ₃ CO-alkyl; (alkyl) _0-1 -NR ₃ CO-aryl; (alkyl) _0-1 -NR ₃ CO-substituted aryl; (alkyl) _0-1 -NR ₃ CO-heteroaryl; (alkyl) _0-1 -NR ₃ CO-substituted heteroaryl; N ₃ ; halogen; haloalkyl; haloalkoxyl; CO-haloalkoxyl; NO ₂ ; CN; HE; SH; and in the case of alkyl, a keto group.

30. The compound according to item 23, wherein R ₄ is phenyl unsubstituted or substituted by one or more substituents selected from the group consisting of methyl, methoxy, halogen, nitrile, nitro, trifluoromethyl and trifluoromethoxyl.

31. The compound according to item 23, wherein R ₄ and R ₅ together form a 3-7-membered substituted or unsubstituted heterocyclic ring.

32. The compound according to item 23, wherein R ₄ and R ₅ together form a substituted or unsubstituted pyrrolidine or morpholine ring.

33. The compound according to claim 1, characterized in that Y is = 0, and X is –SO ₂ -.

34. The compound according to claim 33, wherein n = 0.

35. The compound according to p. 33, wherein R ₃ is hydrogen.

36. The compound according to p. 33, wherein R ₁ is - (CH ₂ ) _2-4 -NR ₃ -CO-NR ₅ -R ₄ .

37. The compound according to p. 33, wherein R ₄ is selected from the group consisting of hydrogen, alkyl, alkyl-O-alkyl, (alkyl) _0-1 aryl, (alkyl) _0-1 - (substituted aryl) , (alkyl) _0-1 and (alkyl) _0-1 (substituted heteroaryl).

38. The compound according to p. 33, wherein R ₂ is selected from the group consisting of hydrogen; alkyl _1-4 ; (C _1-4 alkyl) -O- (C _1-4 alkyl).

39. The compound according to p. 33, wherein R ₄ is selected from the group consisting of aryl, heteroaryl, heterocyclyl, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents selected from the group in which includes: alkyl; alkenyl; aryl; heteroaryl; heterocyclyl; substituted aryl; substituted heteroaryl; substituted heterocyclyl; O-alkyl; O- (alkyl) _0-1 aryl; O- (alkyl) _0-1- substituted aryl; O- (alkyl) _0-1- heteroaryl; O- (alkyl) _0-1- substituted heteroaryl; O- (alkyl) _0-1- heterocyclyl; O- (alkyl) _0-1 substituted heterocyclyl; COOH; CO-O-alkyl; CO-alkyl; S (O) _0-2 -alkyl; S (O) _0-2 - (alkyl) _0-1 -aryl; S (O) _0-2 - (alkyl) _0-1- substituted aryl; S (O) _0-2 - (alkyl) _0-1- heteroaryl; S (O) _0-2 - (alkyl) _0-1- substituted heteroaryl; S (O) _0-2 - (alkyl) _0-1- heterocyclyl; S (O) _0-2 - (alkyl) _0-1- substituted heterocyclyl; (alkyl) _0-1 -NR ₃ R ₃ - (alkyl) _0-1 -NR ₃ CO-O-alkyl; (alkyl) _0-1 -NR ₃ CO-alkyl; (alkyl) _0-1 -NR ₃ CO-aryl; (alkyl) _0-1 -NR ₃ CO-substituted aryl; (alkyl) _0-1 -NR ₃ CO-heteroaryl; (alkyl) _0-1 -NR ₃ CO-substituted heteroaryl; N ₃ ; halogen; haloalkyl; haloalkoxyl; CO-haloalkoxyl; NO ₂ ; CN; HE; SH; and in the case of alkyl, a keto group.

40. The compound according to p. 33, wherein R4 is phenyl unsubstituted or substituted by one or more substituents selected from the group consisting of methyl, methoxy, halogen, nitrile, nitro, trifluoromethyl and trifluoromethoxyl.

41. The compound according to claim 33, wherein R ₄ and R ₅ together form a 3-7 membered substituted or unsubstituted heterocyclic ring.

42. The compound according to p. 33, wherein R ₄ and R ₅ together form a substituted or unsubstituted pyrrolidine or morpholine ring.

43. The compound according to claim 1, characterized in that the dashed bonds in it are absent.

44. The compound according to claim 2, characterized in that the dashed bonds are absent in it.

45. The compound according to p. 12, characterized in that the dotted bonds are absent.

46. The compound according to item 23, wherein the dashed bonds are absent.

47. The compound according to claim 33, wherein the dotted bonds are absent.

48. A compound selected from the group consisting of:

N- [4- (4-amino-1H-imidazo [4,5-c] quinolin-1-yl) butyl] -N’-benzylurea;

N- [4- (4-amino-1H-imidazo [4,5-c] quinolin-1-yl) butyl] -N’-butylurea;

N- [4- (4-amino-1H-imidazo [4,5-c] quinolin-1-yl) butyl] -N ’- (2-ethylphenyl) urea;

N- [4- (4-amino-1H-imidazo [4,5-c] quinolin-1-yl) butyl] -N’-cyclohexylurea;

N ’- [4- (4-amino-1H-imidazo [4,5-c] quinolin-1-yl) butyl] -N-methyl-N-phenylurea;

N- [2- (4-amino-2-butyl-1H-imidazo [4,5-c] quinolin-1-yl) ethyl] -N’-phenylurea;

N- [2- (4-amino-2-butyl-1H-imidazo [4,5-c] quinolin-1-yl) ethyl] -N ’- (4-phenoxyphenyl) urea;

N- [2- (4-amino-2-butyl-1H-imidazo [4,5-c] quinolin-1-yl) ethyl] -N’-benzylurea;

N- [2- (4-amino-2-butyl-1H-imidazo [4,5-c] quinolin-1-yl) ethyl] -N’-propylurea;

N- {2- [4-amino-2 - (- ethoxymethyl) -1H-imidazo [4,5-c] quinolin-1-yl] ethyl} -N’-propylurea;

N- {2- [4-amino-2 - (- ethoxymethyl) -1H-imidazo [4,5-c] quinolin-1-yl] ethyl} -N’-phenylurea;

N- {2- [4-amino-2 - (- ethoxymethyl) -1H-imidazo [4,5-c] quinolin-1-yl] ethyl} -N’-cyclohexylurea;

N- {2- [4-amino-2 - (- ethoxymethyl) -6,7,8,9-tetrahydro-1H-imidazo [4,5-c] quinolin-1-yl] ethyl} -N'-cyclohexylurea ;

N- {2- [4-amino-2 - (- ethoxymethyl) -6,7,8,9-tetrahydro-1H-imidazo [4,5-c] quinolin-1-yl] ethyl} -N'-phenylurea ;

N- [4- (4-amino-2-butyl-1H-imidazo [4,5-s] quinolin-1-yl) butyl] -N’-propylurea;

N- [4- (4-amino-2-butyl-1H-imidazo [4,5-c] quinolin-1-yl) butyl] -N ’- [(1S) -1-phenylethyl] urea;

N- [4- (4-amino-2-butyl-1H-imidazo [4,5-c] quinolin-1-yl) butyl] -N ’- [(1R) -1-phenylethyl] urea;

N- [4- (4-amino-2-butyl-1H-imidazo [4,5-c] quinolin-1-yl) butyl] -N ’- (2-methoxyphenyl) urea;

N- (4-acetylphenyl) N ’- [4- (4-amino-2-butyl-1H-imidazo [4,5-c] quinolin-1-yl) butyl] urea;

N- [4- (4-amino-2-butyl-1H-imidazo [4,5-c] quinolin-1-yl) butyl] -N ’- [4- (dimethylamino) phenyl] urea;

N- [4- (4-amino-2-butyl-1H-imidazo [4,5-c] quinolin-1-yl) butyl] -N ’- (4-methoxybenzyl) urea;

N- {4- [4-amino-2- (2-methoxyethyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N’-propylurea;

N- {4- [4-amino-2- (2-methoxyethyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N ’- (3-methylphenyl) urea;

N- {4- [4-amino-2- (2-methoxyethyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N ’- (3-fluorophenyl) urea;

N ⁴ - {4- [4-amino-2- (2-methoxyethyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -4-morpholinecarboxamide;

N- {4- [4-amino-2- (4-methoxybenzyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N’-propylurea;

N- {4- [4-amino-2- (4-methoxybenzyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N’-phenylurea; and

N- {4- [4-amino-2- (4-methoxybenzyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N ’- (3-pyridyl) urea;

49. A compound selected from the group consisting of:

N- [4- (4-amino-2-butyl-6,7,8,9-tetrahydro-1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N’-benzylurea;

N- {4- [4-amino-2- (2-methoxyethyl) -6,7,8,9-tetrahydro-1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N, N Dimethylurea;

N ⁴ - {4- [4-amino-2- (2-methoxyethyl-6,7,8,9-tetrahydro-1H-imidazo [4,5-c] quinolin-1-yl] butyl} -4-morpholinecarboxamide ; and

N- {4- [4-amino-2- (2-methoxyethyl) -6,7,8,9-tetrahydro-1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N'- phenylurea;

50. A compound selected from the group consisting of:

N- {2- [4-amino-2- (ethoxymethyl) -1H-imidazo [4,5-c] quinolin-1-yl] ethyl} -N’-cyclohexylthiourea;

N- [4- (4-amino-2-butyl-6,7,8,9-tetrahydro-1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N’-cyclohexylthiourea;

N- {4- [4-amino-2- (2-methoxyethyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N ’- (3-pyridyl) urea;

N- {4- [4-amino-2- (2-methoxyethyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N '- (4- (dimethylamino) -1-naphthyl ) thiourea;

N- {4- [4-amino-2- (2-methoxyethyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N’-propylthiourea;

N- {4- [4-amino-2- (2-methoxyethyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N’-phenylthiourea;

N- {4- [4-amino-2- (2-methoxyethyl) -6,7,8,9-tetrahydro-1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N'- phenylthiourea;

N-allylN '- {4- [4-amino-2- (2-methoxyethyl) -6,7,8,9-tetrahydro-1H-imidazo [4,5-c] quinolin-1-yl] butyl} thiourea ;

N- {4- [4-amino-2- (2-methoxyethyl) -6,7,8,9-tetrahydro-1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N'- (tert-butyl) thiourea;

N- {4- [4-amino-2- (2-methoxyethyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N ’- (1-naphthyl) thiourea;

N- {4- [4-amino-2- (2-methoxyethyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} -N ’- (tert-butyl) thiourea; and

N-allylN ’- {4- [4-amino-2- (2-methoxyethyl) -1H-imidazo [4,5-c] quinolin-1-yl] butyl} thiourea.

51. A compound selected from the group consisting of:

4-amino-2-butyl-1- [4 - ({[(phenylsulfonyl) amino] carbonyl} amino) butyl] -6,7,8,9-tetrahydro-1H-imidazo [4,5-c] quinoline;

4-amino-2-butyl-1- [4 - ({[((phenylsulfonyl) amino] carbonyl} amino) butyl] -1H-imidazo [4,5-c] quinoline;

4-amino-2-butyl-1- {4 - [({[((4-fluorophenyl) sulfonyl] amino} carbonyl) amino] butyl} -1H-imidazo [4,5-c] quinoline;

4-amino-2-butyl-1- {4 - [({[((4-chlorophenyl) sulfonyl] amino} carbonyl) amino] butyl} -1H-imidazo [4,5-c] quinoline;

4-amino-2-butyl-1- {4 - [({[((4-ethylphenyl) sulfonyl] amino} carbonyl) amino] butyl} -1H-imidazo [4,5-c] quinoline;

4-amino-2- (2-methoxyethyl) -1- {4 - [({[((4-methylphenyl) sulfonyl] amino} carbonyl) amino] butyl} -1H-imidazo [4,5-quinoline;

4-amino-2- (2-methoxyethyl) -1- [4 - ({[(phenylsulfonyl) amino] carbonyl} amino) butyl] -1H-imidazo [4,5-s] quinoline;

4-amino-2- (ethoxymethyl) -1- [4 - ({[((phenylsulfonyl) amino] carbonyl} amino) ethyl] -1H-imidazo [4,5-c] quinoline;

4-amino-2-butyl-1- {4 - [({[((4-methylphenyl) sulfonyl] amino} carbonyl) amino] ethyl} -1H-imidazo [4,5-s] quinoline;

4-amino-2-butyl-1- {4 - [({[((4-chlorophenyl) sulfonyl] amino} carbonyl) amino] ethyl} -1H-imidazo [4,5-s] quinoline;

52. A pharmaceutical preparation containing a therapeutically effective amount of a compound of formula Ia:

where R ₁ is —alkyl-NR ₃ —CO — OR ₄ or —alkenyl-NR ₃ —CO — O — R ₄ ;

R ₄ is aryl, heteroaryl, heterocyclyl, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents selected from the group consisting of: alkyl; alkenyl; aryl; heteroaryl; heterocyclyl; substituted aryl; substituted heteroaryl; substituted heterocyclyl; O-alkyl; O- (alkyl) _0-1 aryl; O- (alkyl) _0-1- substituted aryl; O- (alkyl) _0-1- heteroaryl; O- (alkyl) _0-1- substituted heteroaryl; O- (alkyl) _0-1- heterocyclyl; O- (alkyl) _0-1 substituted heterocyclyl; COOH; CO-O-alkyl; CO-alkyl; S (O) _0-2 -alkyl; S (O) _0-2 - (alkyl) _0-1 -aryl; S (O) _0-2 - (alkyl) _0-1- substituted aryl; S (O) _0-2 - (alkyl) _0-1- heteroaryl; S (O) _0-2 - (alkyl) _0-1- substituted heteroaryl; S (O) _0-2 - (alkyl) _0-1- heterocyclyl; S (O) _0-2 - (alkyl) _0-1- substituted heterocyclyl; (alkyl) _0-1 —NR ₃ R ₃ ; (alkyl) _0-1 -NR ₃ -CO-O-alkyl; (alkyl) _0-1 -NR ₃ -CO-alkyl; (alkyl) _0-1 -NR ₃ -CO-aryl; (alkyl) _0-1 -NR ₃ -CO-substituted aryl; (alkyl) _0-1 -NR ₃ -CO-heteroaryl; (alkyl) _0-1 -NR ₃ -CO-substituted heteroaryl; N ₃ ; halogen; haloalkyl; haloalkoxyl; CO-haloalkoxyl; NO ₂ ; CN; HE; and SH; and in the case of alkyl, alkenyl or heterocyclyl, a keto group;

R ₂ is selected from the group consisting of: hydrogen; alkyl; alkenyl; aryl; substituted aryl, heteroaryl; substituted heteroaryl; alkyl-O-alkyl; alkyl-O-alkenyl; and alkyl or alkenyl substituted with one or more substituents selected from the group consisting of: OH; halogen; N (R ₃ ) ₂ ; CO-N (R ₃ ) ₂ ; CO-alkyl C _1-10 ; CO-O-alkyl C _1-10 ; N ₃ ; aryl; substituted aryl; heteroaryl; substituted heteroaryl; heterocyclyl; substituted heterocyclyl; CO-aryl; CO- (substituted aryl); CO heteroaryl; and CO- (substituted heteroaryl);

each of R _{3 is} independently selected from the group consisting of hydrogen and C _1-10 alkyl;

n - an integer from 0 to 4, and each R is independently selected from the group consisting of alkyl C _1-10, alkoxy, C _1-10, halogen and trifluoromethyl, or a pharmaceutically acceptable salt thereof in combination with a pharmaceutically acceptable carrier.

53. A pharmaceutical preparation comprising a therapeutically effective amount of a compound according to claim 1 in combination with a pharmaceutically acceptable carrier.

54. A pharmaceutical preparation comprising a therapeutically effective amount of a compound according to claim 2 in combination with a pharmaceutically acceptable carrier.

55. A pharmaceutical preparation comprising a therapeutically effective amount of a compound according to claim 12 in combination with a pharmaceutically acceptable carrier.

56. A pharmaceutical preparation comprising a therapeutically effective amount of a compound according to claim 23 in combination with a pharmaceutically acceptable carrier.

57. A pharmaceutical preparation comprising a therapeutically effective amount of a compound according to claim 33 in combination with a pharmaceutically acceptable carrier.

58. A method of inducing biosynthesis of cytokines in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 1.

59. A method of treating viral diseases in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 1.

60. A method of treating neoplasmic pathologies in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 1.

61. A method of inducing biosynthesis of cytokines in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 2.

62. A method of treating viral diseases in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 2.

63. A method of treating neoplasmic pathologies in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 2.

64. A method for inducing biosynthesis of cytokines in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 12.

65. A method of treating viral diseases in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 12.

66. A method of treating neoplasmic pathologies in animals, comprising

administering to the animal a therapeutically effective amount of a compound according to claim 12.

67. A method for inducing biosynthesis of cytokines in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 23.

68. A method of treating viral diseases in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 23.

69. A method of treating neoplasmic pathologies in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 23.

70. A method of inducing biosynthesis of cytokines in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 33.

71. A method of treating viral diseases in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 33.

72. A method of treating neoplasmic pathologies in animals, comprising administering to the animal a therapeutically effective amount of a compound according to claim 33.

73. A method of inducing biosynthesis of cytokines in animals, comprising administering to the animal a therapeutically effective amount of a preparation according to paragraph 52.

74. A method of treating viral diseases in animals, comprising administering to the animal a therapeutically effective amount of a preparation according to claim 52.

75. A method of treating neoplasmic pathologies in animals, comprising administering to the animal a therapeutically effective amount of a preparation according to paragraph 52.