Soluble guanylate cyclase activators
View Patent ↗A compound of Formula (I): or a pharmaceutically acceptable salt thereof, are capable of modulating the body's production of cyclic guanosine monophosphate (“cGMP”) and are generally suitable for the therapy and prophylaxis of diseases which are associated with a disturbed cGMP balance. The invention furthermore relates to processes for preparing compounds of Formula I, or a pharmaceutically acceptable salt thereof, for their use in the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical preparations which comprise compounds of Formula (I) or a pharmaceutically acceptable salt thereof.
1. A compound having structural Formula I, or a pharmaceutically acceptable salt thereof:
or a pharmaceutically acceptable salt thereof, wherein
is a heteroaryl selected from
where * indicates attachment to the pyrimidinyl ring and ** indicates attachment to the —CH 2 —R 2 of structural Formula I;
Each X 1 , X 2 , X 3 and X 4 is independently N or CH, provided that no more than two of X 1 , X 2 , X 3 and X 4 is N;
Each R x and R y are independently H, C 3-10 cycloalkyl, or —C 1 -C 6 alkyl;
Each R 1 is independently —H, halo, OR, —C 1 -C 6 alkyl, aryl, heterocyclyl, heteroaryl, —C 3-10 cycloalkyl, —CN, —NR a C(O)R b , or —C(O)NR a R b , said aryl, heteroaryl, and cycloalkyl optionally being substituted with one to three substituents selected from halo, —C 1 -C 6 alkyl, —OR, —CN, and —CF 3 ;
R 2 is —(CR d 2 ) t C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —(CR d 2 ) t OR, —(CR d 2 ) t SR, —(CR d 2 ) t CF 3 , —(CR d 2 ) t C 3-10 cycloalkyl, —(CR d 2 ) t -aryl, —(CR d 2 ) t -heterocyclyl or —(CR d 2 ) t heteroaryl, said alkyl, cycloalkyl, aryl, heterocyclyl and heteroaryl being optionally substituted with one to three substituents selected from halo, —C 1 -C 6 alkyl, —CF 3 , —CN or —OR;
R 3 is (CR d 2 ) t -aryl, —(CR d 2 ) t -heteroaryl, —(CR d 2 ) t -heterocyclyl, —(CR d 2 ) t —C 3-10 cycloalkyl, —(CR d 2 ) t CN, —(CR d 2 ) t —C(O)NR a R b , —(CR d 2 ) t NR a C(O)R b , —(CR d 2 ) t —C(S)NR a R b , —(CR d 2 ) t —C(O)OR a , —(CR d 2 ) t —NR a C(O)OR a , —(CR d 2 ) t —NR a R b , or —OR a , said, aryl, heteroaryl or heterocyclyl are optionally substituted with from one to three substituents selected from R 5 ;
R 4 is —C 1 -C 6 alkyl, C 3-10 cycloalkyl, halo or CF 3 ;
Each R 5 is independently halo, OR, CN, —(CR d 2 ) t CF 3 , S(O) p R d , —(CR d 2 ) t C 3-10 cycloalkyl, or —C 1 -C 6 alkyl, said alkyl and cycloalkyl being optionally substituted with one to three substituents selected from halo or OR;
Each R 6 is independently halo, —C 1 -C 6 alkyl, OR, CN, CF 3 , aryl or heteroaryl, where said alkyl, aryl or heteroaryl are optionally substituted with halo, C 1 -C 6 alkyl or CF 3 ;
Each R is independently —H, —C 1 -C 6 alkyl, —CF 3 , or aryl;
Each R a and R b are independently —H, —C 1 -C 6 alkyl, aryl, heteroaryl, heterocyclyl, or —(CH 2 ) 0-3 —C 3-10 cycloalkyl, wherein said alkyl, heteroaryl, heterocyclyl, and cycloalkyl are optionally substituted with one to three substituents selected from R 6 ;
optionally, when R a and R b are —C 1 -C 6 alkyl and are attached to the same nitrogen atom, R a and R b may be cyclized to form a C 3 -C 6 cycloalkyl ring;
Each R d is independently —C 1 -C 6 alkyl, —CF 3 , or aryl;
Each R d is independently H, halo, —CF 3 or —C 1 -C 6 alkyl;
m is an integer selected from 1, 2, or 3;
p is an integer independently selected from 0, 1 or 2; and
t is an integer independently selected from 0, 1, 2, 3, or 4.
2. The compound according to claim 1 , wherein
is a heteroaryl selected from
where * indicates attachment to the pyrimidinyl ring and ** indicates attachment to the —CH 2 —R 2 of structural Formula I;
X 1 , X 2 , X 3 and X 4 are independently selected from N or CH, provided that no more than one of X 1 , X 2 , X 3 and X 4 is N;
or a pharmaceutically acceptable salt thereof.
3. The compound according to claim 1 , wherein R 3 is aryl, heteroaryl, heterocyclyl, CN, —C(O)NR a R b , —NR a C(O)R b , —C(O)OR a , or —OR a , said aryl, heteroaryl or heterocyclyl are optionally substituted with from one to three substituents selected from halo, OR, CN, S(O) p R c , or —C 1 -C 6 alkyl, said alkyl being optionally substituted with one to three substituents selected from halo or OR;
or a pharmaceutically acceptable salt thereof.
4. The compound according to claim 1 having structural Formula III:
or a pharmaceutically acceptable salt thereof,
wherein
X 4 is CH or N;
Each R is independently —H, —C 1 -C 6 alkyl, —CF 3 , or aryl;
Each R a is independently —H or —C 1 -C 6 alkyl;
Each R b is independently —H, —C 1 -C 6 alkyl, —C 3-10 cycloalkyl or heteroaryl, wherein said alkyl, cycloalkyl and heteroaryl are optionally substituted with one to three substituents selected R 6 ;
Each R d is independently —C 1 -C 6 alkyl, —CF 3 , or aryl;
Each R d is independently H, halo, —CF 3 or —C 1 -C 6 alkyl;
Each R 1 is independently —H, OR, CN, halo or —C 1 -C 6 alkyl;
R 2 is —(CR d 2 ) t C 1 -C 6 alkyl, —(CR d 2 ) t CF 3 , —(CR d 2 ) t —C 3-10 cycloalkyl, or —(CR d 2 ) t aryl, said alkyl, cycloalkyl and aryl being optionally substituted with one to three substituents selected from halo, —C 1 -C 6 alkyl and —CF 3 ;
R 3 is aryl, heteroaryl, heterocyclyl, CN, —C(O)NR a R b , —NR a C(O)R b , —C(O)OR a , or —OR a , said aryl, heteroaryl or heterocyclyl are optionally substituted with from one to three substituent selected R 5 ;
R 4 is —CH 3 or C 3-10 cycloalkyl;
Each R 5 is independently halo, OR, CN, S(O) p R d , or —C 1 -C 6 alkyl, said alkyl being optionally substituted with one to three substituents selected from halo or OR;
Each R 6 is independently halo, —C 1 -C 6 alkyl, OR, CN, CF 3 , aryl or heteroaryl, where said alkyl, aryl or heteroaryl are optionally substituted with halo, C 1 -C 6 alkyl or CF 3 ;
m is an integer selected from 1, 2, or 3;
p is an integer independently selected from 0, 1 or 2; and
t is an integer independently selected from 0, 1, 2, 3, or 4.
5. The compound according to claim 1 , which is
1
4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5-methyl-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
2
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
3
4-amino-2-[5-chloro-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5-methyl-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
4
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
5
4-amino-2-[3-(2-fluorobenzyl)-1H-indazol-1-yl]-5-methyl-5-phenyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
6
4-amino-2-[5-chloro-3-(2-fluorobenzyl)-1H-indazol-1-yl]-5-methyl-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
7
4-amino-2-[5-chloro-3-(2-fluorobenzyl)-1H-indazol-1-yl]-5-methyl-5-
(pyridin-3-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
8
4-amino-2-[5-chloro-3-(2-fluorobenzyl)-1H-indazol-1-yl]-5-methyl-5-
(pyridin-4-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
9
4-amino-2-[5-chloro-3-(2,3-difluorobenzyl)-1H-indazol-1-yl]-5-methyl-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
10
4-amino-2-[5-chloro-3-(2,3-difluorobenzyl)-1H-indazol-1-yl]-5-methyl-5-
(pyridin-3-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
11
4-amino-2-[5-chloro-3-(2,3-difluorobenzyl)-1H-indazol-1-yl]-5-methyl-5-
(pyridin-4-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
12
4-amino-5-methyl-5-phenyl-2-[3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
13
4-amino-2-[5-chloro-3-(2-phenylethyl)-1H-indazol-1-yl]-5-methyl-5-phenyl-
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
14
4-amino-5-methyl-5-phenyl-2-[3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
15
4-amino-2-[5-fluoro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5-methyl-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
16
4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5-(4-
fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
17
4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5-methyl-5-
(pyridin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
18
4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5-methyl-5-
(pyridin-3-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
19
4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5-methyl-5-
(pyridin-4-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
20
4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5-methyl-5-
(pyrazin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
21
4-amino-2-[5-chloro-3-(3,3,3-trifluoro-2-methylpropyl)-1H-indazol-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
22
4-amino-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
23
4-amino-5-(2-fluorophenyl)-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-1H-
indazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
24
4-amino-5-(3-fluorophenyl)-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-1H-
indazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
25
4-amino-5-(4-fluorophenyl)-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-1H-
indazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
26
4-amino-2-[5-fluoro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
27
4-amino-2-[5-fluoro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-(2-
fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
28
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-(2-
fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
29
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-(3-
fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
30
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-(4-
fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
31
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-(3,5-
difluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
32
4-amino-5-(4-chlorophenyl)-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-1H-
indazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
33
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-(4-
chlorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
34
4-amino-5-(4-bromophenyl)-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-
indazol-1-yl]-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
35
4-{4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl}benzonitrile,
36
4-amino-5-(4-hydroxyphenyl)-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-
1H-indazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
37
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-[4-(methylsulfonyl)phenyl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
38
4-amino-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
(pyridin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
39
4-amino-2-[5-fluoro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-(pyridin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
40
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-(pyridin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
41
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-(5-
fluoropyridin-2-yl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
42
4-amino-5-(5-chloropyridin-2-yl)-5-methyl-2-[3-(3,3,4,4,4-
pentafluorobutyl)-1H-indazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
43
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-(5-
chloropyridin-2-yl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
44
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-(pyrazin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
45
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
46
4-amino-2-[5-fluoro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
47
4-amino-2-[5-chloro-3-(4,4,5,5,5-pentafluoropentyl)-1H-indazol-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
48
4-amino-2-[5-chloro-3-(3,3,4,4,5,5,5-heptafluoropentyl)-1H-indazol-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
49
methyl 4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5-
methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxylate,
50
ethyl 4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5-
methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxylate,
51
methyl 4-amino-2-[5-fluoro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-
5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxylate,
52
methyl 4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-
5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxylate,
53
4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-thieno[2,3-c]pyrazol-1-yl]-
5-methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
54
4-amino-5-methyl-5-phenyl-2-[3-(2,3,6-trifluorobenzyl)-1H-thieno[3,4-
c]pyrazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
55
4-amino-2-[3-(2,3-difluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
56
4-amino-5-methyl-5-phenyl-2-[3-(3,3,3-trifluoropropyl)-1H-pyrazolo[4,3-
b]pyridin-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
57
4-amino-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[4,3-b]pyridin-
1-yl]-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
58
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
59
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
60
4-amino-5-methyl-5-phenyl-2-[1-(2,2,2-trifluoroethyl)-1H-indazol-3-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
61
4-amino-2-[1-(2-methoxyethyl)-1H-indazol-3-yl]-5-methyl-5-phenyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
62
4-amino-2-[1-(ethoxymethyl)-1H-indazol-3-yl]-5-methyl-5-phenyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
63
4-amino-5-methyl-2-[1-(2,2,3,3,3-pentafluoropropyl)-1H-indazol-3-yl]-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
64
4-amino-2-{1-[(2,2-difluorocyclopropyl)methyl]-1H-indazol-3-yl}-5-methyl-
5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
65
4-amino-5-methyl-5-phenyl-2-[1-(3,3,3-trifluoropropyl)-1H-indazol-3-yl]-
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
66
4-amino-2-[6-chloro-1-(3,3,3-trifluoropropyl)-1H-indazol-3-yl]-5-methyl-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
67
4-amino-2-[6-chloro-1-(3,3,3-trifluoropropyl)-1H-indazol-3-yl]-5-methyl-5-
(3-methyl-1,2,4-oxadiazol-5-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-
one,
68
methyl 4-amino-2-[6-chloro-1-(3,3,3-trifluoropropyl)-1H-indazol-3-yl]-5-
methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxylate,
69
4-amino-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
70
4-amino-2-[6-fluoro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
71
4-amino-2-[6-bromo-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
72
4-amino-5-(2-fluorophenyl)-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-
indazol-3-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
73
4-amino-2-[6-fluoro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-(2-
fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
74
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-(2-
fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
75
4-amino-5-(4-chlorophenyl)-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-
indazol-3-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
76
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-(4-
chlorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
77
4-amino-5-(4-bromophenyl)-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-
indazol-3-yl]-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
78
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-[4-(methylsulfonyl)phenyl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
79
4-amino-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
(pyridin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
80
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-(pyridin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
81
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-(pyrimidin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
82
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-(5-methyl-1,3-oxazol-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
83
4-amino-2-[6-fluoro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
84
4-amino-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-
3-yl]-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
85
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-(5-methyl-1,3,4-thiadiazol-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
86
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
87
4-amino-5-methyl-6-oxo-2-[3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-
6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
88
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
89
4-amino-2-[5-fluoro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-N,5-
dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
90
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-N,5-
dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
91
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-N-
ethyl-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
92
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-N-[(1-methyl-1H-pyrazol-3-yl)methyl]-6-oxo-6,7-dihydro-5H-
pyrrolo[2,3-d]pyrimidine-5-carboxamide,
93
4-amino-5-methyl-5-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2-
[3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
94
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-
methyl-5-(1,3,4-thiadiazol-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-
one,
95
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-N,5-
dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
96
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-5,7-dihydro-
6H-pyrrolo[2,3-d]pyrimidin-6-one,
97
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-(5-methyl-1,3,4-thiadiazol-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
98
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
99
4-amino-5-methyl-5-phenyl-2-[3-(2,3,6-trifluorobenzyl)-4,6-dihydro-1H-
thieno[3,4-c]pyrazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
100
4-amino-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-4,5,6,7-tetrahydro-1H-
indazol-3-yl]-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
101
4-amino-5-(2-fluorophenyl)-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-
4,5,6,7-tetrahydro-1H-indazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
102
4-amino-5-(3-fluorophenyl)-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-
4,5,6,7-tetrahydro-1H-indazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
103
4-amino-5-(4-fluorophenyl)-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-
4,5,6,7-tetrahydro-1H-indazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
104
4-amino-5-methyl-5-phenyl-2-[1-(3,3,3-trifluoropropyl)-4,5,6,7-tetrahydro-
1H-indazol-3-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
105
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-
1-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
106
4-amino-2-[6-fluoro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
107
4-amino-5-methyl-2-[7-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-b]pyridazin-
5-yl]-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
108
4-amino-5-methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-2-[3-(3,3,4,4,4-
pentafluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
109
4-amino-2-[6-fluoro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
110
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
111
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-methyl-5-(5-methyl-1,3-oxazol-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
112
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-methyl-5-(2-methyl-1,3-oxazol-4-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
113
4-amino-2-[3-(2-fluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5-methyl-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
114
4-amino-2-[3-(2-fluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5-methyl-5-
(pyridin-4-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
115
4-amino-2-[6-chloro-3-(2-fluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
116
4-amino-2-[3-(2,3-difluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5-methyl-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
117
4-amino-2-[3-(2,3-difluorobenzyl)-6-fluoroimidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
118
4-amino-2-[3-(2,3-difluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5-(4-
fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
119
4-amino-2-[3-(2,3-difluorobenzyl)-6-fluoroimidazo[1,5-a]pyridin-1-yl]-5-
(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
120
4-amino-2-[3-(2,3-difluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5-methyl-5-
(pyrazin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
121
4-amino-2-[3-(2,3-difluorobenzyl)-6-fluoroimidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-(pyrazin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
122
4-amino-5-methyl-5-phenyl-2-[3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-
1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
123
4-amino-2-[6-fluoro-3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
124
4-amino-2-[6-chloro-3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
125
4-amino-2-[6-fluoro-3-(3,3,3-trifluoropropyl)imidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
126
4-amino-2-[6-chloro-3-(3,3,3-trifluoropropyl)imidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
127
4-amino-5-methyl-5-phenyl-2-[3-(4,4,4-trifluorobutyl)imidazo[1,5-a]pyridin-
1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
128
4-amino-2-[6-fluoro-3-(4,4,4-trifluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
129
4-amino-2-[6-chloro-3-(4,4,4-trifluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
130
4-amino-2-[6-chloro-3-(4,4,4-trifluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-
(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
131
4-amino-2-[6-chloro-3-(4,4,4-trifluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-(pyridin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
132
4-amino-2-[6-chloro-3-(4,4,4-trifluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-
(5-fluoropyridin-2-yl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-
one,
133
4-amino-2-[6-chloro-3-(4,4,4-trifluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-(pyrazin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
134
4-amino-5-methyl-2-[3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-
1-yl]-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
135
4-amino-2-[6-fluoro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-
1-yl]-5-methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
136
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-
1-yl]-5-methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
137
4-amino-5-(2-fluorophenyl)-5-methyl-2-[3-(3,3,4,4,4-
pentafluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
138
4-amino-5-(3-fluorophenyl)-5-methyl-2-[3-(3,3,4,4,4-
pentafluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
139
4-amino-5-(4-fluorophenyl)-5-methyl-2-[3-(3,3,4,4,4-
pentafluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
140
4-amino-5-(3,5-difluorophenyl)-5-methyl-2-[3-(3,3,4,4,4-
pentafluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
141
4-amino-5-(5-chloropyridin-2-yl)-5-methyl-2-[3-(3,3,4,4,4-
pentafluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
142
4-amino-2-[6-fluoro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-
1-yl]-5-(2-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
143
4-amino-2-[6-fluoro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-
1-yl]-5-(3-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
144
4-amino-5-(3,5-difluorophenyl)-2-[6-fluoro-3-(3,3,4,4,4-
pentafluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-methyl-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
145
4-amino-2-[6-fluoro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-methyl-5-(pyridin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
146
4-amino-2-[6-fluoro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
147
ethyl 4-amino-2-[6-fluoro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-
1-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxylate,
148
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-(2-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
149
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-(3-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
150
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-
1-yl]-5-(3,5-difluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
151
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-(4-chlorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
152
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-methyl-5-(pyridin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
153
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-(5-fluoropyridin-2-yl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-
6-one,
154
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-methyl-5-(pyrazin-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-
one,
155
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
156
4-amino-2-[3-(2,3-difluorobenzyl)imidazo[1,5-a]pyrazin-1-yl]-5-methyl-5-
phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
157
ethyl 4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxylate,
158
ethyl 4-amino-5-methyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxylate,
159
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide
160
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-N-
cyclopropyl-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
161
4-amino-5-methyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
162
4-amino-5-cyclopropyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
163
4-amino-5-cyclopropyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carbonitrile,
164
4-amino-N-cyclopropyl-5-methyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-
1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
165
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-6-oxo-N-phenyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
166
ethyl (4-amino-2-(6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl)-
5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl)carbamate,
167
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-(4,5-
dimethyl-1,3-thiazol-2-yl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
168
4-amino-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-5-(1,3,4-thiadiazol-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
169
4-amino-5-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-2-[1-(3,3,4,4,4-
pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
170
4-amino-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-5-pyrimidin-2-yl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-
one,
171
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-[5-oxo-4-(propan-2-yl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
172
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-[4-(propan-2-yl)-5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
173
4-amino-5-(1-ethyl-1H-1,2,3-triazol-4-yl)-5-methyl-2-[1-(3,3,4,4,4-
pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
174
4-amino-5-[(cyclopropylmethyl)amino]-5-methyl-2-[1-(3,3,4,4,4-
pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
175
{4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-6-oxo-6,7-dihydro-5h-pyrrolo[2,3-d]pyrimidin-5-yl}acetonitrile,
176
4-amino-2-(6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl)-N-cyclopropyl-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
177
4-amino-2-(6-cyano-1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl)-N-cyclopropyl-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
178
4-amino-N-cyclopropyl-2-(6-methoxy-1-(3,3,4,4,4-pentafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl)-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
179
4-amino-N-cyclopropyl-5-methyl-2-(6-methyl-1-(3,3,4,4,4-pentafluorobutyl)-
1H-pyrazolo[3,4-b]pyridin-3-yl)-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
180
4-amino-5-[1-(cyclopropylmethyl)-1H-1,2,3-triazol-4-YL]-5-methyl-2-[1-
(3,3,3-trifluoropropyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
181
4-amino-N-cyclopropyl-5-methyl-6-oxo-2-[1-(3,3,3-trifluoropropyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
182
4-amino-5-methyl-6-oxo-N-(pyridin-3-yl)-2-[1-(3,3,3-trifluoropropyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
183
4-amino-2-[6-chloro-1-(3,3,3-trifluoropropyl)-1H-pyrazolo[3,4-b]pyridin-3-
yl]-N-cyclopropyl-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
184
4-amino-N-cyclopropyll-5-methyl-2-[6-methyl-1-(3,3,3-trifluoropropyl)-
1H-pyrazolo[3,4-b]pyridin-3-yl]-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
185
4-amino-N-cyclopropyl-2-[6-methoxy-1-(3,3,3-trifluoropropyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
186
5-methyl-4-(methylamino)-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
187
N-cyclopropyl-5-methyl-4-(methylamino)-6-oxo-2-[1-(3,3,4,4,4-
pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-
pyrrolo[2,3-d]pyrimidine-5-carboxamide,
188
2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-methyl-4-
(methylamino)-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
189
5-methyl-4-(methylamino)-5-(5-methyl-1,3,4-oxadiazol-2-yl)-2-[1-
(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-
6H-pyrrolo[2,3-d]pyrimidin-6-one,
190
4-amino-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-3-
yl]-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
191
4-amino-5-methyl-2-[8-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyrimidin-
6-yl]-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
192
4-amino-2-[6-fluoro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
193
4-amino-5-methyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-
6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
194
4-amino-N-cyclopropyl-5-methyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-
1H-indazol-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
195
4-amino-N-cyclopropyl-2-[6-fluoro-1-(3,3,4,4,4-pentafluorobutyl)-1H-
indazol-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
196
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-N-
cyclobutyl-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
197
4-amino-5-methyl-N-(1-methylethyl)-6-oxo-2-[1-(3,3,4,4,4-
pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-
pyrrolo[2,3-d]pyrimidine-5-carboxamide,
198
4-amino-2-[6-chloro-1-(3,3,3-trifluoropropyl)-1H-indazol-3-yl]-5-methyl-5-
(5-methyl-1,3,4-oxadiazol-2-yl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-
one,
199
4-amino-5-methyl-5-[4-(1-methylethyl)-5-oxo-4,5-dihydro-1,3,4-oxadiazol-
2-yl]-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
200
4-amino-N-cyclopropyl-5-methyl-6-oxo-2-{1-[2-(trifluoromethoxy)ethyl]-
1H-pyrazolo[3,4-b]pyridin-3-yl}-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-
5-carboxamide,
201
4,5-diamino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
202
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
[(cyclopropylmethyl)amino]-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
203
4-amino-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
204
4-amino-5-methyl-5-(1,3,4-oxadiazol-2-yl)-2-[1-(3,3,4,4,4-pentafluorobutyl)-
1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-
one,
205
4-amino-5-methyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-6,7-dihydro-5H-pyrrrolo[2,3-d]pyrimidine-5-carbothiomide,
206
4-amino-5-(4,5-dimethyl-1,3-thiazol-2-yl)-5-methyl-2-[1-(3,3,4,4,4-
pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
207
4-amino-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-5-[3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
208
2-{4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-yl}-N-
cyclopropylacetamide,
209
4-amino-5-methyl-6-oxo-N-pyridin-2-yl-2-{1-[2-(trifluoromethoxy)ethyl]-
1H-pyrazolo[3,4-b]pyridin-3-yl}-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-
5-carboxamide,
210
4-amino-5-methyl-N-(1-methyl-1H-pyrazol-3-yl)-6-oxo-2-{1-[2-
(trifluoromethoxy)ethyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}-6,7-dihydro-5H-
pyrrolo[2,3-d]pyrimidine-5-carboxamide,
211
4-amino-5-(5-ethyl-1,3,4-oxadiazol-2-yl)-5-methyl-2-[1-(3,3,4,4,4-
pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
212
4-amino-5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-5-methyl-2-[1-
(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-
6H-pyrrolo[2,3-d]pyrimidin-6-one,
213
4-amino-5-methyl-5-[5-(1-methylethyl)-1,3,4-oxadiazol-2-yl]-2-[1-
(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-
6H-pyrrolo[2,3-d]pyrimidin-6-one,
214
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
215
4-amino-5-methyl-N-(1-methyl-1H-pyrazol-4-yl)-6-oxo-2-{1-[2-
(trifluoromethoxy)ethyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}-6,7-dihydro-5H-
pyrrolo[2,3-d]pyrimidine-5-carboxamide,
216
4-amino-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-5-[5-(2,2,2-trifluoroethyl)-1,3,4-oxadiazol-2-yl]-5,7-dihydro-
6H-pyrrolo[2,3-d]pyrimidin-6-one,
217
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-N-(1-methyl-1H-pyrazol-4-yl)-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
218
4-amino-5-methyl-N-(1-methyl-1H-pyrazol-3-yl)-6-oxo-2-[1-(3,3,4,4,4-
pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-
pyrrolo[2,3-d]pyrimidine-5-carboxamide,
219
4-amino-5-ethynyl-5-methyl-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
220
4-amino-2-[6-methoxy-1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
221
4-amino-2-[6-cyano-1-(3,3,3-trifluoropropyl)-1H-pyrazolo[3,4-b]pyridin-3-
yl]-N-cyclopropyl-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-
5-carboxamide,
222
4-amino-N-cyclopropyl-5-methyl-6-oxo-2-[1-(4,4,4-trifluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
223
4-amino-N-cyclopropyl-2-[6-cyclopropyl-1-(3,3,4,4,4-pentafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
224
4-amino-N-cyclopropyl-2-[6-cyclopropyl-1-(3,3,3-trifluoropropyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
225
4-amino-5-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-5-methyl-2-[1-(4,4,4-
trifluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
226
4-amino-5-methyl-6-oxo-N-pyridin-2-yl-2-[1-(4,4,4-trifluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
227
4-amino-5-methyl-6-oxo-N-pyridin-3-yl-2-[1-(4,4,4-trifluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
228
4-amino-5-methyl-6-oxo-2-[1-(4,4,4-trifluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
229
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5-
methyl-5-(1-methyl-1H-pyrazol-4-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
230
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-5-methyl-N-oxetan-3-yl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
231
4-amino-5-methyl-N-oxetan-3-yl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-
1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
232
4-amino-5-methyl-5-pyridin-2-yl-2-[1-(3,3,3-trifluoropropyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
233
4-amino-5-methyl-6-oxo-N-pyridin-3-yl-2-{1-[2-(trifluoromethoxy)ethyl]-
1H-pyrazolo[3,4-b]pyridin-3-yl}-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-
5-carboxamide,
234
4-amino-5-methyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-N-pyridin-3-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
235
4-amino-5-methyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-N-(tetrahydrofuran-3-yl)-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
236
4-amino-5-methyl-5-(1,3,4-thiadiazol-2-yl)-2-[1-(4,4,4-trifluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one,
237
4-amino-N-cyclopropyl-5-methyl-6-oxo-2-[1-(3,3,4,4-tetrafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
238
4-amino-N-cyclopropyl-2-[1-(3,3-difluoropropyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
239
4-amino-5-methyl-2-[6-methyl-1-(3,3,4,4,4-pentafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6-oxo-N-(tetrahydro-2H-pyran-4-yl)-6,7-
dihdro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
240
4-amino-N-cyclopropyl-2-[1-(3,3-difluorobutyl)-1H-pyrazolo[3,4-b]pyridin-
3-yl]-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
241
4-amino-5-ethyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
242
4-amino-N,5-dicyclopropyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
243
4-amino-5-cyclopentyl-N-cyclopropyl-6-oxo-2-[-(3,3,4,4,4-
pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-
pyrrolo[2,3-d]pyrimidine-5-carboxamide,
244
4-amino-5-(1-methylethyl)-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
245
4-amino-N,5-dicyclopropyl-6-oxo-2-[1-(3,3,3-trifluoropropyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
246
4-amino-N,5-dicyclopropyl-6-oxo-2-[1-(4,4,4-trifluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
247
4-amino-5-cyclopropyl-6-oxo-2-[1-(4,4,4-trifluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
248
4-amino-2-[6-fluoro-3-(4,4,4-trifluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-[3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
249
4-amino-2-[6-chloro-3-(4,4,4-trifluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-
methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
250
4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-H-cyclopropyl-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
251
4-amino-H-cyclopropyl-5-methyl-6-oxo-2-[7-(3,3,4,4,4-
pentafluorobutyl)imidazo[1,5-b]pyridazin-5-yl]-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
252
4-amino-H-cyclopropyl-2-[6-fluoro-3-(3,3,4,4,4-
pentafluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-methyl-6-oxo-6,7-dihydro-
5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
253
4-amino-2-[6-fluoro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-
yl]-5-methyl-6-oxo-H-pyridin-3-yl-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
254
4-amino-5-methyl-6-oxo-2-[7-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-
b]pyridazin-5-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
255
4-amino-5-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-5-methyl-2-[7-(3,3,4,4,4-
pentafluorobutyl)imidazo[1,5-b]pyridazin-5-yl]-5,7-dihydro-6H-pyrrolo[2,3-
d]pyrimidin-6-one,
256
4-amino-H-cyclopropyl-5-methyl-6-oxo-2-[7-(3,3,3-
trifluoropropyl)imidazo[1,5-b]pyridazin-5-yl]-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
257
2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-N-cyclopropyl-
5-methyl-4-(methylamino)-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-
5-carboxamide,
258
2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-N,5-dimethyl-4-
(methylamino)-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
259
N,5-dimethyl-4-(methylamino)-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-
pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
260
N-cyclopropyl-5-methyl-4-(methylamino)-6-oxo-2-[7-(3,3,4,4,4-
pentafluorobutyl)imidazo[1,5-b]pyridazin-5-yl]-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
261
5-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-5-methyl-4-(methylamino)-2-[1-
(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,7-dihydro-
6H-pyrrolo[2,3-d]pyrimidin-6-one,
262
N,5-dicyclopropyl-4-(methylamino)-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-
1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
263
N-cyclopropyl-5-methyl-4-(methylamino)-6-oxo-2-[1-(3,3,3-trifluoropropyl)-
1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
264
N-cyclopropyl-5-methyl-4-(methylamino)-6-oxo-2-[1-(4,4,4-trifluorobutyl)-
1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
265
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-N,N,5-
trimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
266
4-amino-N-cyclopropyl-5-methyl-6-oxo-2-[3-(3,3,4,4,4-pentafluorobutyl)-
1H-pyrazolo[4,3-b]pyridin-1-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-
carboxamide,
267
4-amino-2-[5-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-N-cyclopropyl-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
268
4-amino-2-[5-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-N-cyclopropyl-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-
d]pyrimidine-5-carboxamide,
269
4-amino-2-[5-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-
b]pyridin-3-yl]-5-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one,
270
4-amino-5-methyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-
a]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide,
or a pharmaceutically acceptable salt thereof.
6. A pharmaceutical composition comprised of the compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
7. The pharmaceutical composition of claim 6 comprising one or more pharmaceutically active agents in addition to the compound of claim 1 , or a pharmaceutically acceptable salt thereof.
8. The pharmaceutical composition of claim 7 wherein the one or more additional active agents is selected from an angiotensin converting enzyme inhibitor, an angiotensin II receptor antagonist, a neutral endopeptidase inhibitor, an aldosterone antagonist, a renin inhibitor, an endothelin receptors antagonist, an aldosterone synthase inhibitor, a phosphodiesterase-5 inhibitor, a vasodilator, a calcium channel blocker, a potassium channel activator, a diuretic, a sympatholitic, a beta-adrenergic blocking drug, an alpha adrenergic blocking drug, a central alpha adrenergic agonist, a peripheral vasodilator, a lipid lowering agent or a metabolic altering agent.
9. The compound of claim 1 or a pharmaceutically acceptable salt thereof that is
10. The compound of claim 9 that is
11. A pharmaceutical composition comprised of the compound of claim 9 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
12. The compound of claim 1 or a pharmaceutically acceptable salt thereof that is
13. The compound of claim 12 that is
14. A pharmaceutical composition comprised of the compound of claim 12 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
15. The compound of claim 1 or a pharmaceutically acceptable salt thereof that is
16. The compound of claim 15 that is
17. A pharmaceutical composition comprised of the compound of claim 15 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.