3-aryl-5,6-disubstituted pyridazines
View Patent ↗The present invention provides compounds of Formula (I) or (II) salt form or prodrug thereof, wherein variables are defined herein, that are modulators of metalloproteases such as matrix metalloproteases (MMPs) and ADAMs. The compounds or compositions described herein can be used to treat diseases associated with metalloprotease activity including, for example, arthritis, cancer, cardiovascular disorders, skin disorders, inflammation or allergic conditions.
1. A compound selected from:
Cpd
#
Structure
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Cpd
#
Name
1
N-(cyclopropylmethyl)-4-mesityl-N-propylphthalazin-1-amine
2
4-mesityl-N,N-dipropylphthalazin-1-amine
3
4-(4-methoxyphenyl)-N,N-dipropylphthalazin-1-amine
4
4-(4-chlorophenyl)-N-(cyclopropylmethyl)-N-propylphthalazin-
1-amine
5
N-(cyclopropylmethyl)-4-(2-methylphenyl)-N-propylphthalazin-
1-amine
6
4-(5-chloro-2-methoxyphenyl)-N-(cyclopropylmethyl)-N-propyl-
phthalazin-1-amine
7
N-(cyclopropylmethyl)-4-(1-naphthyl)-N-propylphthalazin-1-amine
8
N-methyl-4-(2-methylphenyl)-N-(1-phenylethyl)phthalazin-1-amine
9
4-(5-chloro-2-methoxyphenyl)-N-methyl-N-(1-phenylethyl)-
phthalazin-1-amine
10
4-(2-fluorophenyl)-N-methyl-N-(1-phenylethyl)phthalazin-1-amine
11
4-(2-methylphenyl)-N,N-dipropylphthalazin-1-amine
12
4-(5-chloro-2-methoxyphenyl)-N,N-dipropylphthalazin-1-amine
13
N-butyl-4-(5-chloro-2-methoxyphenyl)-N-ethylphthalazin-1-amine
14
N-methyl-4-(1-naphthyl)-N-(1-phenylethyl)phthalazin-1-amine
15
4-(2-chlorophenyl)-N-methyl-N-(1-phenylethyl)phthalazin-1-amine
16
N-methyl-N-(1-phenylethyl)-4-[2-(trifluoromethyl)-
phenyl]phthalazin-1-amine
17
4-(1-naphthyl)-N,N-dipropylphthalazin-1-amine
18
4-(2-chlorophenyl)-N,N-dipropylphthalazin-1-amine
19
N-butyl-N-ethyl-4-(1-naphthyl)phthalazin-1-amine
20
N-benzyl-4-(2-chlorophenyl)-N-ethylphthalazin-1-amine
21
N-benzyl-N-ethyl-4-[2-(trifluoromethyl)phenyl]phthalazin-
1-amine
22
4-mesityl-N-methyl-N-[(1S)-1-phenylethyl]phthalazin-
1-amine
23
4-mesityl-N-methyl-N-(1-phenylbutyl)phthalazin-1-amine
24
4-mesityl-N-methyl-N-(2-methyl-1-phenylpropyl)phthalazin-
1-amine
25
N-(2,3-dihydro-1H-inden-1-yl)-4-mesityl-N-methylphthalazin-
1-amine
26
N-benzyl-N-ethyl-4-mesitylphthalazin-1-amine
27
N-benzyl-N-isobutyl-4-mesitylphthalazin-1-amine
28
4-mesityl-N-(2-phenylethyl)-N-propylphthalazin-1-amine
29
4-(2,4-dimethoxyphenyl)-N-methyl-N-(1-phenylethyl)phthalazin-
1-amine
30
4-(2,4-dimethoxyphenyl)-N-methyl-N-(1-phenylbutyl)phthalazin-
1-amine
31
4-(2,4-dimethoxyphenyl)-N-methyl-N-(2-methyl-1-phenylpropyl)-
phthalazin-1-amine
32
N-(2,3-dihydro-1H-inden-1-yl)-4-(2,4-dimethoxyphenyl)-N-
methylphthalazin-1-amine
33
4-(2,4-dimethoxyphenyl)-N-(2-phenylethyl)-N-propylphthalazin-
1-amine
34
3-methyl-4-(4-{methyl[(1S)-1-phenylethyl]amino}phthalazin-
1-yl)phenol
35
3-methyl-4-{4-[methyl(1-phenylbutyl)amino]phthalazin-
1-yl}phenol
36
3-methyl-4-{4-[methyl(2-methyl-1-phenylpropyl)amino]phthalazin-
1-yl}phenol
37
4-{4-[2,3-dihydro-1H-inden-1-yl(methyl)amino]phthalazin-1-
yl}-3-methylphenol
38
4-{4-[benzyl(ethyl)amino]phthalazin-1-yl}-3-methylphenol
39
4-{4-[(cyclopropylmethyl)(propyl)amino]phthalazin-1-yl}-
3-methylphenol
40
3-methyl-4-{4-[(2-phenylethyl)(propyl)amino]phthalazin-
1-yl}phenol
41
4-{4-[cyclohexyl(ethyl)amino]phthalazin-1-yl}-3-methylphenol
42
4-mesityl-N-methyl-N-(1-phenylethyl)phthalazin-1-amine
43
4-mesityl-N-methyl-N-[(1R)-1-phenylethyl]phthalazin-1-amine
44
4-mesityl-N-methyl-N-(1-phenylpropyl)phthalazin-1-amine
45
N-cyclohexyl-4-mesityl-N-methylphthalazin-1-amine
46
4-mesityl-N-methyl-N-(1,2,3,4-tetrahydronaphthalen-
1-yl)phthalazin-1-amine
47
4-mesityl-N-methyl-N-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-
5-yl)phthalazin-1-amine
48
3-methyl-4-{4-[methyl(1-phenylethyl)amino]phthalazin-1-
yl}phenol
49
3-methyl-4-(4-{methyl[(1R)-1-phenylethyl]amino}-
phthalazin-1-yl)phenol
50
3-methyl-4-{4-[methyl(1-phenylpropyl)amino]phthalazin-
1-yl}phenol
51
4-{4-[cyclohexyl(methyl)amino]phthalazin-1-yl}-3-methylphenol
52
3-methyl-4-{4-[methyl(1,2,3,4-tetrahydronaphthalen-1-
yl)amino]phthalazin-1-yl}phenol
53
3-methyl-4-{4-[methyl(6,7,8,9-tetrahydro-5H-benzo[7]annulen-
5-yl)amino]phthalazin-1-yl}phenol
54
4-mesityl-N-(2-methylbenzyl)phthalazin-1-amine
55
4-mesityl-N-[(1R)-1-(4-methoxyphenyl)ethyl]phthalazin-1-amine
56
4-mesityl-N-[(1S)-1-(4-methoxyphenyl)ethyl]phthalazin-1-amine
57
N-benzyl-4-mesityl-N-methylphthalazin-1-amine
58
4-mesityl-N-methyl-N-(2-methylbenzyl)phthalazin-1-amine
59
N-(2-chlorobenzyl)-4-mesityl-N-methylphthalazin-1-amine
60
4-mesityl-N-(2-methoxybenzyl)-N-methylphthalazin-1-amine
61
4-mesityl-N-(3-methoxybenzyl)-N-methylphthalazin-1-amine
62
4-mesityl-N-(4-methoxybenzyl)-N-methylphthalazin-1-amine
63
N-(3,4-dihydro-2H-chromen-4-yl)-4-mesityl-N-
methylphthalazin-1-amine
64
N,N-bis(1,3-benzodioxol-5-ylmethyl)-4-mesitylphthalazin-
1-amine
65
4-(2-methoxy-4,6-dimethylphenyl)-N,N-dipropylphthalazin-
1-amine
66
N-(3,4-dihydro-2H-chromen-4-yl)-4-(2-methoxy-4,6-
dimethylphenyl)phthalazin-1-amine
67
4-(2,6-dimethylphenyl)-N-methyl-N-(1,2,3,4-tetrahydro-
naphthalen-1-yl)phthalazin-1-amine
68
N-(3,4-dihydro-2H-chromen-4-yl)-4-(2,6-dimethylphenyl)-
N-methylphthalazin-1-amine
69
N-(cyclopropylmethyl)-4-(2,6-dimethylphenyl)-N-
propylphthalazin-1-amine
70
4-(2,6-dimethylphenyl)-N-methyl-N-[(1S)-1-phenylethyl]-
phthalazin-1-amine
71
4-[4-(dipropylamino)phthalazin-1-yl]-3,5-dimethylphenol
72
4-(2,6-dimethylphenyl)-N-methyl-N-[1-(2-methylphenyl)-
ethyl]phthalazin-1-amine
73
N-[1-(1,3-benzodioxol-5-yl)ethyl]-4-(2,6-dimethylphenyl)-
N-methylphthalazin-1-amine
74
4-(2,6-dimethylphenyl)-N-[(1R)-1-(3-methoxyphenyl)ethyl]-
N-methylphthalazin-1-amine
75
N-benzyl-4-(2,6-dimethylphenyl)-N-isopropylphthalazin-1-amine
76
N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(2,6-
dimethylphenyl)-N-methylphthalazin-1-amine
77
N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(2,6-
dimethylphenyl)-N-propylphthalazin-1-amine
78
4-(2,6-dimethylphenyl)-N-(3-ethoxybenzyl)-N-
methylphthalazin-1-amine
79
4-(2,6-dimethylphenyl)-N-(3-ethoxybenzyl)-N-
propylphthalazin-1-amine
80
rel-N-[(4aR,8aS)-decahydronaphthalen-1-yl]-4-(2,6-
dimethylphenyl)-N-methylphthalazin-1-amine
81
N-(1-cyclohexylethyl)-4-(2,6-dimethylphenyl)-N-
methylphthalazin-1-amine
82
4-(2,6-dimethylphenyl)-N-(3-methoxybenzyl)-N-
methylphthalazin-1-amine
83
4-(2,6-dimethylphenyl)-N-methyl-N-[3-(trifluoromethyl)-
benzyl]phthalazin-1-amine
84
4-(2,6-dimethylphenyl)-N-methyl-N-[4-(trifluoromethyl)-
benzyl]phthalazin-1-amine
85
4-(2,6-dimethylphenyl)-N-methyl-N-[2-(trifluoromethyl)-
benzyl]phthalazin-1-amine
86
N-(cyclopropylmethyl)-4-(2,6-diethylphenyl)-N-
propylphthalazin-1-amine
87
1-(5-chloro-2-methoxyphenyl)-4-(1-propyl-3,4-dihydroisoquinolin-
2(1H)-yl)phthalazine
88
1-(2-fluorophenyl)-4-(1-propyl-3,4-dihydroisoquinolin-
2(1H)-yl)phthalazine
89
1-(2-methylphenyl)-4-[2-(2-phenylethyl)piperidin-1-yl]phthalazine
90
N-methyl-N-(1-phenylethyl)-4-quinolin-8-ylphthalazin-1-amine
91
1-(2-chlorophenyl)-4-(1-propyl-3,4-dihydroisoquinolin-
2(1H)-yl)phthalazine
92
1-(1-propyl-3,4-dihydroisoquinolin-2(1H)-yl)-4-quinolin-
8-ylphthalazine
93
1-(1-propyl-3,4-dihydroisoquinolin-2(1H)-yl)-4-[2-(trifluoro-
methyl)phenyl]phthalazine
94
N-butyl-N-ethyl-4-quinolin-8-ylphthalazin-1-amine
95
1-azepan-1-yl-4-(4-chlorophenyl)phthalazine
96
1-(1-ethyl-3,4-dihydroisoquinolin- 2(1H)-yl)-4-mesitylphthalazine
97
1-(2,4-dimethoxyphenyl)-4-(1-ethyl-3,4-dihydroisoquinolin-
2(1H)-yl)phthalazine
98
4-[4-(1-ethyl-3,4-dihydroisoquinolin-2(1H)-yl)phthalazin-
1-yl]-3-methylphenol
99
1-(3,4-dihydroisoquinolin-2(1H)-yl)-4-mesitylphthalazine
100
1-mesityl-4-(1-methyl-3,4-dihydroisoquinolin-
2(1H)-yl)phthalazine
101
1-mesityl-4-(1-propyl-3,4-dihydroisoquinolin-
2(1H)-yl)phthalazine
102
1-(1-cyclopropyl-3,4-dihydroisoquinolin-2(1H)-yl)-
4-mesitylphthalazine
103
1-(2-ethylpiperidin-1-yl)-4-mesitylphthalazine
104
1-(6,7-dimethoxy-1-methyl-3,4-dihydroisoquinolin-
2(1H)-yl)-4-mesitylphthalazine
105
4-[4-(3,4-dihydroisoquinolin-2(1H)-yl)phthalazin-
1-yl]-3-methylphenol
106
3-methyl-4-[4-(1-methyl-3,4-dihydroisoquinolin-2(1H)-
yl)phthalazin-1-yl]phenol
107
3-methyl-4-[4-(1-propyl-3,4-dihydroisoquinolin-2(1H)-
yl)phthalazin-1-yl]phenol
108
4-[4-(1-cyclopropyl-3,4-dihydroisoquinolin-2(1H)-yl)phthalazin-
1-yl]-3-methylphenol
109
4-[4-(2-ethylpiperidin-1-yl)phthalazin-1-yl]-3-methylphenol
110
1-(cyclohexylmethoxy)-4-mesitylphthalazine
111
1-(cyclohexyloxy)-4-mesitylphthalazine
112
1-(1-ethylpropoxy)-4-mesitylphthalazine
113
1-mesityl-4-(1-phenylpropoxy)phthalazine
114
1-mesityl-4-(4-phenylpiperazin-1-yl)phthalazine
115
1-[(2R)-4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-
4-mesitylphthalazine
116
1-(1-cyclobutyl-7-methoxy-3,4-dihydroisoquinolin-
2(1H)-yl)-4-(2,6-dimethylphenyl)phthalazine
117
N-(cyclopropylmethyl)-4-(1H-indol-4-yl)-N-propyl-
phthalazin-1-amine
118
4-(1H-indazol-4-yl)-N,N-dipropylphthalazin-1-amine
119
1-butoxy-4-(2,6-dimethylphenyl)phthalazine
120
1-(2,6-dimethylphenyl)-4-(1,2,3,4-tetrahydronaphthalen-
1-yloxy)phthalazine
121
1-(3,4-dihydroisoquinolin-2(1H)-yl)-4-(2,6-dimethyl-
phenyl)phthalazine
122
4-{4-[(cyclopropylmethyl)(propyl)amino]phthalazin-1-yl}-1H-
indole-3-carbonitrile
123
1-(2,6-dimethylphenyl)-4-(3-phenylpyrrolidin-1-yl)phthalazine
124
1-mesityl-4-(pyrrolidin-2-ylmethoxy)phthalazine
125
1-(2,6-dimethylmorpholin-4-yl)-4-mesitylphthalazine
126
1-(2,6-dimethylphenyl)-4-(1-methyl-3,4-dihydroisoquinolin-
2(1H)-yl)phthalazine
127
1-(1-cyclopropyl-3,4-dihydroisoquinolin-2(1H)-yl)-4-(2,6-
dimethylphenyl)phthalazine
128
1-[4-(2-chloro-4-fluorophenoxy)piperidin-1-yl]-4-(2,6-
dimethylphenyl)phthalazine
129
1-(1-cyclopropyl-3,4-dihydroisoquinolin-2(1H)-yl)-4-(2,5-
difluorophenyl)phthalazine
130
ethyl 4-chloro-3-[4-(1-cyclopropyl-3,4-dihydroisoquinolin-
2(1H)-yl)phthalazin-1-yl]benzoate
or a pharmaceutically acceptable salt thereof.