US 2011/0218202 A1Published application

Soluble guanylate cyclase activators

AssigneeMerck Sharp & Dohme Corp.

InventorsLinda L. Brockunier, Jian Guo, Emma R. Parmee, Subharekha Raghavan, Keith Rosauer, Darby Schmidt, John E. Stelmach

Life of this patent

Estimating the term…

Abstract

Compounds of Formula I 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 the Formula I, to their use for the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical preparations which comprise compounds of the Formula I.

Claims18

Dependent claims

A compound having structural Formula I, or a pharmaceutically acceptable salt thereof:

wherein:
is an 8- or 9-membered heteroaryl;
Ra and Rb are independently selected at each occurrence from the group consisting of —H and —C1-C6 alkyl;
Rc is independently selected at each occurrence from the group consisting of —C1-C6 alkyl, —CF3, and aryl;
R1 is independently selected at each occurrence from the group consisting of —H, halo, aryl, heteroaryl, —C1-C6 alkyl, —C3-10 cycloalkyl, —OR, —NO2, —CN, —CO2Ra, —NRaRb, —S(O)pRc, thioxo, azido, —C(═O)Ra, —OC(O)nRa, —OC(═O)ORa, —OC(═O)NRaRb, —SO2NRaNRb, —NRa(C═O)nRb, —NRaSO2Rb, —NRaC(═O)ORb, —NRaC(O)NRaRb, —NRaSO2NRaRb, —C2-10alkenyl, and —C2-10alkynyl, said aryl, heteroaryl, alkyl, cycloalkyl, alkenyl and alkynyl optionally being substituted with one to three substituents selected from halo, —C1-C6 alkyl, —OR, oxo, aryl, heteroaryl, —C3-10 cycloalkyl, —NO2, —CN, —CO2Ra, NRaRb, —S(O)pRe, thioxo, azido, —C(═O)Ra, O(C═O)nRa, —OC(═O)ORa, —OC(═O)NRa, —OC(═O)NRaRb, —SO2NRaNRb, —NRa(C═O)nRb, —NRaSO2Rb, —NRaC(═O)ORb, —NRaC(═O)NRaRb, —NRaSO2NRaRb and —CF3;
R2 is selected from the group consisting of —C1-C6 alkyl, —(CRa2)rOR, —(CRa2)rS(O)pRc, —(CRa2)r—CF3, —(CRa2)r—C3-10cycloalkyl, —(CRa2)raryl, —(CRa2)rheteroaryl, —(CRa2)r—C2-10alkenyl, —(CRa2)r—C2-10alkynyl, and —(CRa2)rC(O)Oalkyl, said alkyl, cycloalkyl, aryl, hetetoaryl, alkenyl and alkynyl being optionally substituted with one to three substituents selected from halo, —C1-C6 alkyl, —CF3, —CN and —OR;
R is independently selected at each occurrence from the group consisting of —H, —C1-C6 alkyl, —CF3, and aryl;
R3 and R4 are independently selected from the group consisting of —H and —C1-C6 alkyl;
when R3 and R4 are C1-C6 alkyl they may optionally be joined to form a cycloalkyl;
m is 0, 1, 2, or 3;
p is 0, 1 or 2;
r is 0, 1, 2, 3, 4, 5, or 6;
and
z is 0 or 1.

11 more elements

A compound selected from the group consisting of

Example
IUPAC NAME
1
4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
2
4-amino-5,5-dimethyl-2-[3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-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]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
4
4-amino-5,5-dimethyl-2-[3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
5
4-amino-2-(5-fluoro-3-hexyl-1H-indazol-1-yl)-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2
d]pyrimidin-6-one
6
4-amino-2-[5-bromo-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
7
4-amino-5,5-dimethyl-2-[5-pyridin-4-yl-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,7
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
8
4-amino-5,5-dimethyl-2-[3-(4,4,4-trifluorobutyl)-1H-thieno[3,4-c]pyrazol-1-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
9
4-amino-5,5-dimethyl-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
10
4-amino-5,5-dimethyl-2-[3-(2,3,6-trifluorobenzyl)-4,6-dihydro-1H-thieno[3,4-c]pyraz
1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
11
4-amino-2-[3-(2-cyclopentylethyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
12
4-amino-2-[3-(2-fluorobenzyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
13
4-amino-2-[5-chloro-3-(2-fluorobenzyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydro-6
pyrrolo[2,3-d]pyrimidin-6-one
14
4-amino-2-[5-fluoro-3-(2-fluorobenzyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydro-6
pyrrolo[2,3-d]pyrimidin-6-one
15
4-amino-2-[5-chloro-3-(2,3-difluorobenzyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydr
6H-pyrrolo[2,3-d]pyrimidin-6-one
16
4-amino-2-[3-(2,3-difluorobenzyl)-5-fluoro-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydr
6H-pyrrolo[2,3-d]pyrimidin-6-one
17
4-amino-2-[3-(2,3-difluorobenzyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
18
4-amino-2-[3-(2-fluorobenzyl)-5-phenyl-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydro-6
pyrrolo[2,3-d]pyrimidin-6-one
19
4-amino-2-[5-fluoro-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
20
4-amino-5,5-dimethyl-2-[5-pyridin-3-yl-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,7
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
21
4-amino-5,5-dimethyl-2-[5-(1-methyl-1H-pyrazol-4-yl)-3-(2,3,6-trifluorobenzyl)-1H-
indazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
22
4-amino-2-[5-(3,5-dimethyl-1H-pyrazol-4-yl)-3(2,3,6-trifluorobenzyl)-1H-indazol-1-
yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
23
4-amino-2-[5-(3-furyl)-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
24
4-amino-5,5-dimethyl-2-[5-(4-methyl-3-thienyl)-3-(2,3,6-trifluorobenzyl)-1H-indazol-
yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
25
4-amino-2-[5-cyclopropyl-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
26
4-amino-5,5-dimethyl-2-[5-pyridin-4-yl-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl] -5,7
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
27
4-amino-5,5-dimethyl-2-[5-phenyl-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
28
4-amino-2-[5-chloro-3-(pyrimidin-5-ylmethyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
29
4-amino-5,5-dimethyl-2-[5-(3-thienyl)-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
30
4-amino-2-[5-(5-fluoropyridin-3-yl)-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,5-
dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
31
4-amino-2-[5-(6-fluoropyridin-3-yl)-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,5-
dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
32
4-amino-5,5-dimethyl-2-{3-(2,3,6-trifluorobenzyl)-5-[5-(trifluoromethyl)pyridin-3-yl]-
1H-indazol-1-yl}-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
33
4-amino-2-[3-(6-bromo-2,3-difluorobenzyl)-5-chloro-1H-indazol-1-yl]-5,5-dimethyl-5
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
34
4-amino-2-[3-(2-cyclopentylethyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
35
4-amino-2-(5-fluoro-3-pentyl-1H-indazol-1-yl)-5,5-dimethyl-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
36
4-amino-2-[5-fluoro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
37
4-amino-2-[3-(2-cyclopentylethyl)-5-fluoro-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydr
6H-pyrrolo[2,3-d]pyrimidin-6-one
38
4-amino-2-[3-(2-cyclopentylethyl)-5-fluoro-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydr
6H-pyrrolo[2,3-d]pyrimidin-6-one
39
4-amino-2-[5-fluoro-3-(4,4,4-trifluorobutyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihyd
6H-pyrrolo[2,3-d]pyrimidin-6-one
40
4-amino-2-(5-chloro-3-pentyl-1H-indazol-1-yl)-5,5-dimethyl-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
41
4-amino-2-(3-butyl-5-chloro-1H-indazol-1-yl)-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2
d]pyrimidin-6-one
42
4-amino-2-[5-chloro-3-(4,4,4-trifluorobutyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihyd
6H-pyrrolo[2,3-d]pyrimidin-6-one
43
4-amino-2-(5-chloro-3-pent-4-en-1-yl-1H-indazol-1-yl)-5,5-dimethyl-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
44
4-amino-2-(3-but-3-en-1-yl-5-chloro-1H-indazol-1-yl)-5,5-dimethyl-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
45
4-amino-2-(5-chloro-3-propyl-1H-indazol-1-yl)-5,5-dimethyl-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
46
ethyl 3-[1-(4-amino-5,5-dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-2-yl)
5-chloro-1H-indazol-3-yl]propanoate
47
4-amino-2-[5-chloro-3-(3,3-dimethylbutyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7-dihydro
6H-pyrrolo[2,3-d]pyrimidin-6-one
48
4-amino-2-[3-(2,3-difluorobenzyl)-1H-thieno[3,4-c]pyrazol-1-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
49
4-amino-2-[6-chloro-3-(2,3-difluorobenzyl)-1H-thieno[3,4-c]pyrazol-1-yl]-5,5-dimeth
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
50
4-amino-2-[5-chloro-3-(2,3-difluorobenzyl)-1H-thieno[2,3-c]pyrazol-1-yl]-5,5-dimeth
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
51
4-amino-2-[3-(2,3-difluorobenzyl)-1H-thieno[3,2-c]pyrazol-1-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
52
4-amino-2-[5-chloro-3-(2,3,6-trifluorobenzyl)-1H-thieno[2,3-c]pyrazol-1-yl]-5,5-
dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
53
4-amino-5,5-dimethyl-2-[3-(2,3,6-trifluorobenzyl)-1H-thieno[3,2-c]pyrazol-1-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
54
4-amino-5,5-dimethyl-2-[5-methyl-3-(2,3,6-trifluorobenzyl)pyrazolo[4,3-c]pyrazol-
1(5H)-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
55
4-amino-5,5-dimethyl-2-[3-(2,3,6-trifluorobenzyl)-1H-thieno[2,3-c]pyrazol-1-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
56
4-amino-5,5-dimethyl-2-[6-methyl-3-(2,3,6-trifluorobenzyl)pyrazolo[3,4-c]pyrazol-
1(6H)-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
57
4-amino-5,5-dimethyl-2-[3-(2,3,6-trifluorobenzyl)-1H-pyrazolo[4,3-c]pyridin-1-yl]-5,
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
58
4-amino-5,5-dimethyl-2-[7-(2,3,6-trifluorobenzyl)imidazo[1,5-b]pyridazin-5-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
59
4-amino-2-[6-chloro-3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,5-dimethy
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
60
4-amino-2-[6-fluoro-3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,5-dimethy
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
61
4-amino-5,5-dimethyl-2-[5-(2,3,6-trifluorobenzyl)imidazo[5,1-b][1,3]thiazol-7-yl]-5,7
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
62
4-amino-5,5-dimethyl-2-[1-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-3-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
63
4-amino-2-[3-(2,3-difluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,5-dimethyl-5,7-dihyd
6H-pyrrolo[2,3-d]pyrimidin-6-one
64
4-amino-2-[7-(2,3-difluorobenzyl)imidazo[1,5-b]pyridazin-5-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
65
4-amino-2-[3-(2,3-difluorobenzyl)-6-fluoroimidazo[1,5-a]pyridin-1-yl]-5,5-dimethyl-
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
66
4-amino-2-[7-(2-fluorobenzyl)imidazo[1,5-b]pyridazin-5-yl]-5,5-dimethyl-5,7-dihydro
6H-pyrrolo[2,3-d]pyrimidin-6-one
67
4-amino-2-[3-(2-fluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,5-dimethyl-5,7-dihydro-6
pyrrolo[2,3-d]pyrimidin-6-one
68
4-amino-2-[6-fluoro-3-(2-fluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
69
4-amino-2-[6-chloro-3-(2-fluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
70
4-amino-2-[7-(2,3-difluorobenzyl)-2-methylimidazo[1,5-b]pyridazin-5-yl]-5,5-dimeth
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
71
4-amino-2-[6-chloro-3-(2,3-difluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,5-dimethyl-
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
72
4-amino-2-(3-benzylimidazo[1,5-a]pyridin-1-yl)-5,5-dimethyl-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
73
4-amino-5,5-dimethyl-2-[3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
74
4-amino-5,5-dimethyl-2[6-phenyl-3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl
5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
75
4-amino-2-[6-(2-fluorophenyl)-3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,
dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
76
4-amino-2-[6-(3-fluorophenyl)-3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,
dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
77
4-amino-2-[6-(4-fluorophenyl)-3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,
dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
78
4-amino-2-[6-(3-chlorophenyl)-3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,
dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
79
4-amino-5,5-dimethyl-2-[6-(3-thienyl)-3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-
yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
80
4-amino-2-[6-cyclopropyl-3-(2,3,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,5-
dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
81
4-amino-5,5-dimethyl-2-[7-(3,3,3-trifluoropropyl)imidazo[1,5-b]pyridazin-5-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
82
4-amino-5,5-dimethyl-2-[3-(2,4,6-trifluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
83
4-amino-2-[3-(2-chloro-6-fluoro-3-methylbenzyl)imidazo[1,5-a]pyridin-1-yl]-5,5-
dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
84
4-amino-2-[3-(2-cyclopentylethyl)imidazo[1,5-a]pyridin-1-yl]-5,5-dimethyl-5,7-dihyd
6H-pyrrolo[2,3-d]pyrimidin-6-one
85
4-amino-5,5-dimethyl-2-[7-(4,4,4-trifluorobutyl)imidazo[1,5-b]pyridazin-5-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
86
4-amino-5,5-dimethyl-2-[3-(4,4,4-trifluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
87
4-amino-5,5-dimethyl-2-{3-[2-(2-thienyl)ethyl]imidazo[1,5-a]pyridin-1-yl}-5,7-dihyd
6H-pyrrolo[2,3-d]pyrimidin-6-one
88
4-amino-2-[3-(2-cyclopropylethyl)imidazo[1,5-a]pyridin-1-yl]-5,5-dimethyl-5,7-dihyd
6H-pyrrolo[2,3-d]pyrimidin-6-one
89
4-amino-5,5-dimethyl-2-(3-pentylimidazo[1,5-a]pyridin-1-yl)-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
90
4-amino-5,5-dimethyl-2-(7-pentylimidazo[1,5-b]pyridazin-5-yl)-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
91
4-amino-5,5-dimethyl-2-[3-(3-methylbutyl)imidazo[1,5-a]pyridin-1-yl]-5,7-dihydro-6
pyrrolo[2,3-d]pyrimidin-6-one
92
4-amino-5,5-dimethyl-2-[3-methyl-5-(2,3,6-trifluorobenzyl)imidazo[5,1-b][1,3]thiazol
7-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
93
4-amino-5,5-dimethyl-2-[2-methyl-5-(2,3,6-trifluorobenzyl)imidazo[5,1-b][1,3]thiazol
7-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
94
4-amino-2-[5-(2-fluorobenzyl)imidazo[5,1-b][1,3]thiazol-7-yl]-5,5-dimethyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
95
4-amino-5,5-dimethyl-2-[1-(3,3,3-trifluoropropyl)-1H-indazol-3-yl]-5,7-dihydro-6H-
pyrrolo[2,3-d]pyrimidin-6-one
96
4-amino-2-[5-chloro-3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,5-dimethyl-5,8-
dihydropyrido[2,3-d]pyrimidin-7(6H)-one
97
4-amino-5,5-dimethyl-2-[3-(2,3,6-trifluorobenzyl)-1H-indazol-1-yl]-5,8-
dihydropyrido[2,3-d]pyrimidin-7(6H)-one
98
4-amino-5,5-dimethyl-2-[3-(2,3,6-trifluorobenzyl)-1H-thieno[3,4-c]pyrazol-1-yl]-5,8-
dihydropyrido[2,3-d]pyrimidin-7(6H)-one
99
4-amino-5,5-dimethyl-2-[3-(2,3,6-trifluorobenzyl)-4,6-dihydro-1H-thieno[3,4-c]pyraz
1-yl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one
100
4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5-ethyl-5-methyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
101
4-amino-2-[5-chloro-3-(3,3,3-trifluoropropyl)-1H-indazol-1-yl]-5-methyl-5-propyl-5,7
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
102
4-amino-2-[5-chloro-3-(3,3-dimethylbutyl)-1H-indazol-1-yl]-5-ethyl-5-methyl-5,7-
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
103
4-amino-5-ethyl-2-[3-(2-fluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-5-methyl-5,7-dihyd
6H-pyrrolo[2,3-d]pyrimidin-6-one
104
4-amino-5,5-dimethyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5,7-dihydro-
6H-pyrrolo[2,3-d]pyrimidin-6-one
105
4-amino-2-[5-fluoro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
106
4-amino-2-[5-chloro-3-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5,5-dimethyl-5,7
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
107
4-amino-5,5-dimethyl-2-[3-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[4,3-b]pyridin-1-
yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
108
4-amino-5,5-dimethyl-2-[3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5,
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]-5,5-
dimethyl-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]-5,5-
dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
111
4-amino-2-[6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-indazol-3-yl]-5,5-dimethyl-5,7
dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
indicates data missing or illegible when filed
and the pharmaceutically acceptable salts thereof.

334 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/127,334Filed 16 Nov 2009
Priority: 25 Nov 2008
Published: 8 Sep 2011
Term ends: Not estimatedThe source records don’t support an estimate.

Classification16 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
A61P 7/02
Drugs for disorders of the blood or the extracellular fluid: antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors

Family

Application61/200,221Us provisional application · filed 25 Nov 2008
US 8,741,910 B2Related patent
US 2011/0218202 A1This patent

From the US filing history. Foreign family members aren’t listed.

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Citations

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Abstract

A compound having structural Formula I, or a pharmaceutically acceptable salt thereof:

wherein:
is an 8- or 9-membered heteroaryl;
Ra and Rb are independently selected at each occurrence from the group consisting of —H and —C1-C6 alkyl;
Rc is independently selected at each occurrence from the group consisting of —C1-C6 alkyl, —CF3, and aryl;
R1 is independently selected at each occurrence from the group consisting of —H, halo, aryl, heteroaryl, —C1-C6 alkyl, —C3-10 cycloalkyl, —OR, —NO2, —CN, —CO2Ra, —NRaRb, —S(O)pRc, thioxo, azido, —C(═O)Ra, —OC(O)nRa, —OC(═O)ORa, —OC(═O)NRaRb, —SO2NRaNRb, —NRa(C═O)nRb, —NRaSO2Rb, —NRaC(═O)ORb, —NRaC(O)NRaRb, —NRaSO2NRaRb, —C2-10alkenyl, and —C2-10alkynyl, said aryl, heteroaryl, alkyl, cycloalkyl, alkenyl and alkynyl optionally being substituted with one to three substituents selected from halo, —C1-C6 alkyl, —OR, oxo, aryl, heteroaryl, —C3-10 cycloalkyl, —NO2, —CN, —CO2Ra, NRaRb, —S(O)pRe, thioxo, azido, —C(═O)Ra, O(C═O)nRa, —OC(═O)ORa, —OC(═O)NRa, —OC(═O)NRaRb, —SO2NRaNRb, —NRa(C═O)nRb, —NRaSO2Rb, —NRaC(═O)ORb, —NRaC(═O)NRaRb, —NRaSO2NRaRb and —CF3;
R2 is selected from the group consisting of —C1-C6 alkyl, —(CRa2)rOR, —(CRa2)rS(O)pRc, —(CRa2)r—CF3, —(CRa2)r—C3-10cycloalkyl, —(CRa2)raryl, —(CRa2)rheteroaryl, —(CRa2)r—C2-10alkenyl, —(CRa2)r—C2-10alkynyl, and —(CRa2)rC(O)Oalkyl, said alkyl, cycloalkyl, aryl, hetetoaryl, alkenyl and alkynyl being optionally substituted with one to three substituents selected from halo, —C1-C6 alkyl, —CF3, —CN and —OR;
R is independently selected at each occurrence from the group consisting of —H, —C1-C6 alkyl, —CF3, and aryl;
R3 and R4 are independently selected from the group consisting of —H and —C1-C6 alkyl;
when R3 and R4 are C1-C6 alkyl they may optionally be joined to form a cycloalkyl;
m is 0, 1, 2, or 3;
p is 0, 1 or 2;
r is 0, 1, 2, 3, 4, 5, or 6;
and
z is 0 or 1.

11 more elements

Facts

Application

13/127,334Filed 16 Nov 2009

Priority

25 Nov 2008

Published

8 Sep 2011

Term ends

Not estimatedThe source records don’t support an estimate.

Classification16 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
A61P 7/02
Drugs for disorders of the blood or the extracellular fluid: antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors