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1. WO2013004617 - PYRAZOLOPYRIDINES USEFUL IN THE TREATMENT OF DISORDERS OF THE CENTRAL NERVOUS SYSTEM

Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters

[ EN ]

A compound according to formula [I]


[I]

wherein A4 is C-R4 or N, A5 is C-R5 or N and A6 is C-R6 or N, provided that at least one of A4, A5 or A6 is N and no more than two of A4, A5 and A6 is N;

R1 is phenyl or heteroaryl; wherein said phenyl or heteroaryl is optionally substituted with one or more substituents R1 1 , wherein each R1 1 is individually selected from Ci-6alkyl, halogen, hydroxy, haloCi-6alkyl, Ci-6alkoxy, haloCi-6alkoxy, cyano, Ci-6alkylsulfonyl, -S(0)2NH2 and -NR12R13, wherein R12 and R13 independently represent hydrogen or Ci-6alkyl;

R2 is selected from H, Ci-6alkyl, C2-6alkenyl, C2-6alkynyl, Ci-6alkoxy, halogen and cyano; R3, R4, R5, R6 and R7 are selected independently of each other from H, Ci-6alkyl, C2-

6alkenyl, C2-6alkynyl, Ci-6alkoxy, halogen, cyano, and -NR9R10, wherein R9 and R10 independently represent hydrogen, Ci-6alkyl, C2-6alkenyl, C2-6alkynyl, haloCi-6alkyl or phenyl; R8 is selected from H, Ci-6alkyl, C2-6alkenyl, C2-6alkynyl, Ci-6alkoxy, halogen, cyano and phenyl;

and pharmaceutically acceptable salts thereof.

2. The compound according to claim 1 , wherein each R1 1 is individually selected from methyl, trifluoromethyl, fluorine, hydroxy, methoxy, difluoromethoxy, trifluoromethoxy, cyano, methylsulfonyl, -S(0)2NH2 and -N(CH3)2;

R2 is selected from H, methyl and methoxy;

R3, R4, R5, R6 and R7 are selected independently of each other from H, methyl, methoxy, cyano and N(CH3)2;

R8 is selected from H, methyl and phenyl.

3. The compound according to any of claims 1 -2, wherein only one of A4, A5 or A6 is N.

4. The compound according to any of claims 1 -2, wherein two of A4, A5 or A6 are N

5. The compound according to any of claims 1 -4, wherein R1 represents a phenyl optionally substituted with one or more R1 1 .

6. The compound according to any of claims 1 -4, wherein R1 represents a 6-membered heteroaryl optionally substituted with one or more R1 1 .

7. The compound according to any of claims 1 -4, wherein R1 represents a 5-membered heteroaryl optionally substituted with one or more R1 1.

8. The compound according to any of claims 1 -7, wherein R1 is optionally substituted with one R1 1 .

9. The compound according to claim 8, wherein said R1 1 is selected from methyl, trifluoromethyl, fluorine, hydroxy, methoxy, difluoromethoxy, trifluoromethoxy, cyano, methyl-sulfonyl, -S(0)2NH2 and -N(CH3)2.

10. The compound according to any of claims 1 -9, wherein R2, R3, R4, R5, R6 and R7 are selected independently of each other from H, methyl and methoxy.

1 1 . The compound according to any of claims 1 -10, wherein R8 is selected from H, methyl and phenyl.

12. A compound according to claim 1 selected from

1 : 1-(4-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2,4-dimethyl-pyridin-3-yl)-amide;

2 : 3, 6-Di methyl- 1 -phenyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

3: 3,6-Dimethyl-1 -phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (3,5-dimethyl-pyridin-4-yl)-amide;

4: 1-(2-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2,4-dimethyl-pyridin-3-yl)-amide;

5 : 1 -(4-Methoxy-phenyl)-3, 6-dimethyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2-methyl-pyridin-3-yl)-amide;

6 : 3, 6-Di methyl- 1 -p-tolyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

7: 1-(4-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2-methoxy-4-methyl-pyridin-3-yl)-amide;

8: 1-(4-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (4-methyl-pyridin-3-yl)-amide;

9: 1-(3-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2,4-dimethyl-pyridin-3-yl)-amide;

10: 3, 6-Dimethyl- 1-( 6-methyl-pyridin-3-yl)- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

11 : 1-(4-Methoxy-phenyl)-6-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2,4-dimethyl-pyridin-3-yl)-amide;

12: 1-(4-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (4,6-dimethyl-pyrimidin-5-yl)-amide;

13: 1-(4-Fluoro-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2,4-dimethyl-pyridin-3-yl)-amide;

14: 1-(4-Cyano-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2,4-dimethyl-pyridin-3-yl)-amide;

15: 1-(4-Methoxy-phenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2,4-dimethyl-pyridin-3-yl)-amide;

16: 1-( 6-Methoxy-pyridin-3-yl)-3, 6-dimethyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

17: 3, 6-Dimethyl- 1 -(4-trifluoromethoxy-phenyl)- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

18: 1-(4-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2,4,6-trimethyl-pyridin-3-yl)-amide;

19: 7 -(4-Difluoromethoxy-phenyl)-3, 6-dimethyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

20: 1-(4-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (4-methyl-pyrimidin-5-yl)-amide;

21 : 3,6-Dimethyl-1-(4-sulfamoyl-phenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2,4-dimethyl-pyridin-3-yl)-amide;

22 : 3, 6-Dimethyl- 1 -(4-trifluoromethyl-phenyl)- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

23: 7 -(4-Dimethylamino-phenyl)-3, 6-dimethyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

24: 3-Methoxy- 1 -(4-methoxy-phenyl)-6-methyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

25 : 3, 6-Dimethyl- 1 -thiophen-3-yl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

26: 3,6-Dimethyl-1-pyrimidin-5-yl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2,4-dimethyl-pyridin-3-yl)-amide;

27: 3, 6-Dimethyl- 1 -phenyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2-methoxy-4-methyl-pyridin-3-yl)-amide;;

28: 3, 6-Dimethyl- 1 -phenyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid (4-methoxy-2-methyl-pyridin-3-yl)-amide;

29: 3, 6-Dimethyl- 1 -phenyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid (4-methoxy-6-methyl-pyridin-3-yl)-amide;

30: 1-(4-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (4-dimethylamino-pyridin-3-yl)-amide;

31 : 3, 6-Dimethyl- 1 -phenyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2-methyl-pyridin-3-yl)-amide;

32 : 3, 6-Dimethyl- 1 -phenyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid (4-methyl-pyridin-3-yl)-amide;

33: 1-(4-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (4,6-dimethyl-pyridin-3-yl)-amide;

34: 1-(4-Methanesulfonyl-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

35 : 7 -(4-Methoxy-phenyl)-3-methyl-6-phenyl- 1 H-pyrazolo[3, 4-b]pyridine-4-carboxylic acid ( 2, 4-dimethyl-pyridin-3-yl)-amide;

36: 1-(4-Methoxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (4-cyano-pyridin-3-yl)-amide;

37: 1-(4-Hydroxy-phenyl)-3,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (2,4-dimethyl-pyridin-3-yl)-amide;

and pharmaceutically acceptable salts of any of these compounds.

13. A compound according to any of claims 1 -12 for use as a medicament.

14. A compound according to any of claims 1 -12, for use in the treatment of a disease or disorder selected from Psychosis; Schizophrenia; cognitive disorders; cognitive impairment associated with schizophrenia; Attention Deficit Hyperactivity Disorder (ADHD); autism spectrum disorders, Alzheimer's disease (AD); mild cognitive impairment (MCI); age associated

memory impairment (AAMI); senile dementia; AIDS dementia; Pick's disease; dementia associated with Lewy bodies; dementia associated with Down's syndrome; Huntington's Disease; Parkinson's disease (PD); obsessive-compulsive disorder (OCD); traumatic brain injury; epilepsy; post-traumatic stress; Wernicke-Korsakoff syndrome (WKS); post-traumatic amnesia; cognitive deficits associated with depression; diabetes, weight control, inflammatory disorders, reduced angiogenesis; amyotrophic lateral sclerosis and pain.

15. A pharmaceutical composition comprising a compound according to any of claims 1 -12, and one or more pharmaceutically acceptable carrier or excipient.