US2005113451A1PendingUtilityA1
2-amino-2-alkyl-5 heptenoic and heptynoic acid derivatives useful as nitric oxide synthase inhibitors
Est. expirySep 15, 2020(expired)· nominal 20-yr term from priority
Inventors:Donald W. Hansen, Jr.Ronald Keith WebberBarnett S. PitzeleJames A. SikorskiMark A. MassaTimothy J. HagenMargaret L. GrapperhausLijuan WangArija A. BergmanisSteven W. KramerE. Ann Hallinan
A61P 37/00A61P 43/00A61P 9/10A61P 35/00A61P 3/10A61P 9/00A61P 27/06A61P 25/04A61P 25/06A61P 25/28A61P 29/00A61P 27/02A61P 1/16A61P 1/04A61P 11/06A61P 1/02A61P 21/04A61P 17/02A61P 17/06A61P 19/08A61P 19/02A61P 19/00A61P 11/00C07C 271/22C07B 2200/09C07D 413/06C07B 2200/07C07C 229/30C07D 271/07C07C 257/14C07C 259/14C07F 7/1804
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Claims
Abstract
The present invention relates to 2-amino-2-alkyl-5 heptenoic and heptynoic acid derivatives and their use in therapy, in particular their use as nitric oxide synthase inhibitors.
Claims
exact text as granted — not AI-modified1 . A compound of Formula I:
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and
R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
2 . The compound of claim 1 wherein the compound is the Z isomer.
3 . The compound of claim 2 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy.
4 . The compound of claim 3 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by fluorine or alkoxy.
5 . The compound of claim 3 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy.
6 . The compound of claim 3 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl optionally substituted by fluorine.
7 . The compound of claim 3 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
8 . The compound of claim 3 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
9 . The compound of claim 8 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and halo; and R 3 is C 1 -C 3 alkyl.
10 . The compound of claim 9 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is C 1 -C 3 alkyl.
11 . The compound of claim 10 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is methyl.
12 . The compound of claim 11 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methyl.
13 . The compound of claim 11 wherein:
R 1 is hydrogen; R 2 is fluorine; and R 3 is methyl.
14 . The compound of claim 3 wherein:
R 1 is halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
15 . The compound of claim 14 wherein:
R 1 is halo; R 2 is halo; and R 3 is C 1 -C 3 alkyl.
16 . The compound of claim 15 wherein:
R 1 is fluorine; R 2 is fluorine; and R 3 is methyl.
17 . The compound of claim 14 wherein:
R 1 is fluorine; R 2 is selected from the group consisting of hydrogen and C 1 -C 3 alkyl; and R 3 is methyl.
18 . The compound of claim 17 wherein:
R 1 is fluorine; R 2 is hydrogen; and R 3 is methyl.
19 . The compound of claim 3 wherein:
R 1 is methyl; R 2 is hydrogen; and R 3 is methyl.
20 . The compound of claim 3 wherein:
R 1 is hydrogen; R 2 is methyl; and R 3 is methyl.
21 . The compound of claim 3 wherein:
R 1 is methyl; R 2 is methyl; and R 3 is methyl.
22 . The compound of claim 2 wherein:
R 1 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; and R 3 is methyl optionally substituted by one or more alkoxy or halo.
23 . The compound of claim 22 wherein:
R 1 is selected from the group consisting of hydrogen and fluorine; R 2 is C 1 -C 3 alkyl substituted by one or more halo; and R 3 is methyl.
24 . The compound of claim 23 wherein:
R 1 is hydrogen; R 2 is CH 2 F; and R 3 is methyl.
25 . The compound of claim 22 wherein:
R 1 is CH 2 F; R 2 is hydrogen; and R 3 is methyl.
26 . The compound of claim 22 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is CH 2 F.
27 . The compound of claim 22 wherein:
R 1 is hydrogen; R 2 is methoxymethyl; and R 3 is methyl.
28 . The compound of claim 22 wherein:
R 1 is methoxymethyl; R 2 is hydrogen; and R 3 is methyl.
29 . The compound of claim 22 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methoxymethyl.
30 . The compound of claim 1 wherein the compound is the E isomer.
31 . The compound of claim 30 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by one or more halo or alkoxy.
32 . The compound of claim 31 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy.
33 . The compound of claim 31 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl optionally substituted by fluorine.
34 . The compound of claim 31 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by fluorine or alkoxy.
35 . The compound of claim 31 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
36 . The compound of claim 31 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
37 . The compound of claim 36 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and halo; and R 3 is C 1 -C 3 alkyl.
38 . The compound of claim 37 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is C 1 -C 3 alkyl.
39 . The compound of claim 38 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is methyl.
40 . The compound of claim 39 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methyl.
41 . The compound of claim 39 wherein:
R 1 is hydrogen; R 2 is fluorine; and R 3 is methyl.
42 . The compound of claim 31 wherein:
R 1 is halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
43 . The compound of claim 42 wherein:
R 1 is halo; R 2 is halo; and R 3 is C 1 -C 3 alkyl.
44 . The compound of claim 39 wherein:
R 1 is fluorine; R 2 is fluorine; and R 3 is methyl.
45 . The compound of claim 42 wherein:
R 1 is fluorine; R 2 is selected from the group consisting of hydrogen and C 1 -C 3 alkyl; and R 3 is methyl.
46 . The compound of claim 45 wherein:
R 1 is fluorine; R 2 is hydrogen; and R 3 is methyl.
47 . The compound of claim 31 wherein:
R 1 is methyl; R 2 is hydrogen; and R 3 is methyl.
48 . The compound of claim 31 wherein:
R 1 is hydrogen; R 2 is methyl; and R 3 is methyl.
49 . The compound of claim 31 wherein:
R 1 is methyl; R 2 is methyl; and R 3 is methyl.
50 . The compound of claim 30 wherein:
R 1 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; and R 3 is methyl optionally substituted by alkoxy or one or more halo.
51 . The compound of claim 50 wherein:
R 1 is selected from the group consisting of hydrogen and fluorine; R 2 is C 1 -C 3 alkyl substituted by one or more halo; and R 3 is methyl.
52 . The compound of claim 51 wherein:
R 1 is hydrogen; R 2 is CH 2 F; and R 3 is methyl.
53 . The compound of claim 50 wherein:
R 1 is CH 2 F; R 2 is hydrogen; and R 3 is methyl.
54 . The compound of claim 50 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is CH 2 F.
55 . The compound of claim 50 wherein:
R 1 is hydrogen; R 2 is methoxymethyl; and R 3 is methyl.
56 . The compound of claim 50 wherein:
R 1 is methoxymethyl; R 2 is hydrogen; and R 3 is methyl.
57 . The compound of claim 50 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methoxymethyl.
58 . A compound of Formula II
or a pharmaceutically acceptable salt thereof, wherein:
R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
59 . The compound of claim 58 wherein:
R 3 is C 1 -C 5 alkyl substituted by one or more halo.
60 . The compound of claim 59 wherein:
R 3 is C 1 -C 5 alkyl substituted by one or more fluorine.
61 . The compound of claim 59 wherein:
R 3 is methyl substituted by one or more halo.
62 . The compound of claim 61 wherein:
R 3 is methyl substituted by one or more fluorine.
63 . The compound of claim 61 wherein:
R 3 is CH 2 F.
64 . The compound recited in claim 59 wherein:
R 3 is C 1 -C 5 alkyl substituted by alkoxy.
65 . The compound of claim 64 wherein:
R 3 is methoxy methyl.
66 . The compound of claim 59 wherein:
R 3 is C 1 -C 5 alkyl.
67 . The compound of claim 65 wherein:
R 3 is methyl.
68 . A compound of Formula III
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and
R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
69 . The compound of claim 68 wherein the compound is the Z isomer.
70 . The compound of claim 69 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by one or more halo or alkoxy.
71 . The compound of claim 69 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy
72 . The compound of claim 69 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl optionally substituted by fluorine.
73 . The compound of claim 70 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by fluorine or alkoxy.
74 . The compound of claim 70 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
75 . The compound of claim 70 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
76 . The compound of claim 75 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and halo; and R 3 is C 1 -C 3 alkyl.
77 . The compound of claim 76 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is C 1 -C 3 alkyl.
78 . The compound of claim 77 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is methyl.
79 . The compound of claim 78 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methyl.
80 . The compound of claim 78 wherein:
R 1 is hydrogen; R 2 is fluorine; and R 3 is methyl.
81 . The compound of claim 70 wherein:
R 1 is halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
82 . The compound of claim 81 wherein:
R 1 is halo; R 2 is halo; and R 3 is C 1 -C 3 alkyl.
83 . The compound of claim 82 wherein:
R 1 is fluorine; R 2 is fluorine; and R 3 is methyl.
84 . The compound of claim 81 wherein:
R 1 is fluorine; R 2 is selected from the group consisting of hydrogen and C 1 -C 3 alkyl; and R 3 is methyl.
85 . The compound of claim 84 wherein:
R 1 is fluorine; R 2 is hydrogen; and R 3 is methyl.
86 . The compound of claim 70 wherein:
R 1 is methyl; R 2 is hydrogen; and R 3 is methyl.
87 . The compound of claim 70 wherein:
R 1 is hydrogen; R 2 is methyl; and R 3 is methyl.
88 . The compound of claim 70 wherein:
R 1 is methyl; R 2 is methyl; and R 3 is methyl.
89 . The compound of claim 69 wherein:
R 1 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; and R 3 is methyl optionally substituted by one or more alkoxy or halo.
90 . The compound of claim 89 wherein:
R 1 is selected from the group consisting of hydrogen and fluorine; R 2 is C 1 -C 3 alkyl substituted by one or more halo; and R 3 is methyl.
91 . The compound of claim 90 wherein:
R 1 is hydrogen; R 2 is CH 2 F; and R 3 is methyl.
92 . The compound of claim 89 wherein:
R 1 is CH 2 F; R 2 is hydrogen; and R 3 is methyl.
93 . The compound of claim 89 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is CH 2 F.
94 . The compound of claim 89 wherein:
R 1 is hydrogen; R 2 is methoxymethyl; and R 3 is methyl.
95 . The compound of claim 89 wherein:
R 1 is methoxymethyl; R 2 is hydrogen; and R 3 is methyl.
96 . The compound of claim 89 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methoxymethyl.
97 . The compound of claim 68 wherein the compound is the E isomer.
98 . The compound of claim 97 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by one or more halo or alkoxy.
99 . The compound of claim 98 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy
100 . The compound of claim 98 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl optionally substituted by fluorine.
101 . The compound of claim 98 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by one or more fluorine or alkoxy.
102 . The compound of claim 98 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
103 . The compound of claim 98 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
104 . The compound of claim 103 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and halo; and R 3 is C 1 -C 3 alkyl.
105 . The compound of claim 104 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is C 1 -C 3 alkyl.
106 . The compound of claim 105 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is methyl.
107 . The compound of claim 106 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methyl.
108 . The compound of claim 106 wherein:
R 1 is hydrogen; R 2 is fluorine; and R 3 is methyl.
109 . The compound of claim 98 wherein:
R 1 is halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
110 . The compound of claim 109 wherein:
R 1 is halo; R 2 is halo; and R 3 is C 1 -C 3 alkyl.
111 . The compound of claim 110 wherein:
R 1 is fluorine; R 2 is fluorine; and R 3 is methyl.
112 . The compound of claim 109 wherein:
R 1 is fluorine; R 2 is selected from the group consisting of hydrogen and C 1 -C 3 alkyl; and R 3 is methyl.
113 . The compound of claim 112 wherein:
R 1 is fluorine; R 2 is hydrogen; and R 3 is methyl.
114 . The compound of claim 98 wherein:
R 1 is methyl; R 2 is hydrogen; and R 3 is methyl.
115 . The compound of claim 98 wherein:
R 1 is hydrogen; R 2 is methyl; and R 3 is methyl.
116 . The compound of claim 98 wherein:
R 1 is methyl; R 2 is methyl; and R 3 is methyl.
117 . The compound of claim 97 wherein:
R 1 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; and R 3 is methyl optionally substituted by one or more alkoxy or halo.
118 . The compound of claim 117 wherein:
R 1 is selected from the group consisting of hydrogen and fluorine; R 2 is C 1 -C 3 alkyl substituted by one or more halo; and R 3 is methyl.
119 . The compound of claim 118 wherein:
R 1 is hydrogen; R 2 is CH 2 F; and R 3 is methyl.
120 . The compound of claim 117 wherein:
R 1 is CH 2 F; R 2 is hydrogen; and R 3 is methyl.
121 . The compound of claim 117 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is CH 2 F.
122 . The compound of claim 117 wherein:
R 1 is hydrogen; R 2 is methoxymethyl; and R 3 is methyl.
123 . The compound of claim 117 wherein:
R 1 is methoxymethyl; R 2 is hydrogen; and R 3 is methyl.
124 . The compound of claim 117 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methoxymethyl.
125 . A compound of Formula IV
or a pharmaceutically acceptable salt thereof, wherein:
R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
126 . The compound of claim 125 wherein:
R 3 is C 1 -C 5 alkyl substituted by one or more halo.
127 . The compound of claim 126 wherein:
R 3 is C 1 -C 5 alkyl substituted by one or more fluorine.
128 . The compound of claim 126 wherein:
R 3 is methyl substituted by one or more halo.
129 . The compound of claim 128 wherein:
R 3 is methyl substituted by one or more fluorine.
130 . The compound of claim 128 wherein:
R 3 is CH 2 F.
131 . The compound recited in claim 126 wherein:
R 3 is C 1 -C 5 alkyl substituted by alkoxy.
132 . The compound of claim 131 wherein:
R 3 is methoxy methyl.
133 . The compound of claim 126 wherein:
R 3 is C 1 -C 5 alkyl.
134 . The compound of claim 132 wherein:
R 3 is methyl.
135 . A compound of Formula V
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and
R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
136 . The compound of claim 135 wherein the compound is the Z isomer.
137 . The compound of claim 136 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy.
138 . The compound of claim 137 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy
139 . The compound of claim 137 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl optionally substituted by fluorine.
140 . The compound of claim 136 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by fluorine or alkoxy.
141 . The compound of claim 137 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
142 . The compound of claim 137 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
143 . The compound of claim 142 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and halo; and R 3 is C 1 -C 3 alkyl.
144 . The compound of claim 143 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is C 1 -C 3 alkyl.
145 . The compound of claim 144 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is methyl.
146 . The compound of claim 145 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methyl.
147 . The compound of claim 145 wherein:
R 1 is hydrogen; R 2 is fluorine; and R 3 is methyl.
148 . The compound of claim 137 wherein:
R 1 is halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
149 . The compound of claim 148 wherein:
R 1 is halo; R 2 is halo; and R 3 is C 1 -C 3 alkyl.
150 . The compound of claim 149 wherein:
R 1 is fluorine; R 2 is fluorine; and R 3 is methyl.
151 . The compound of claim 148 wherein:
R 1 is fluorine; R 2 is selected from the group consisting of hydrogen and C 1 -C 3 alkyl; and R 3 is methyl.
152 . The compound of claim 151 wherein:
R 1 is fluorine; R 2 is hydrogen; and R 3 is methyl.
153 . The compound of claim 137 wherein:
R 1 is methyl; R 2 is hydrogen; and R 3 is methyl.
154 . The compound of claim 137 wherein:
R 1 is hydrogen; R 2 is methyl; and R 3 is methyl.
155 . The compound of claim 137 wherein:
R 1 is methyl; R 2 is methyl; and R 3 is methyl.
156 . The compound of claim 136 wherein:
R 1 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; and R 3 is C 1 -C 5 alkyl optionally substituted by alkoxy or one or more halo.
157 . The compound of claim 156 wherein:
R 1 is selected from the group consisting of hydrogen and fluorine; R 2 is C 1 -C 3 alkyl substituted by one or more halo; and R 3 is methyl.
158 . The compound of claim 157 wherein:
R 1 is hydrogen; R 2 is CH 2 F; and R 3 is methyl.
159 . The compound of claim 156 wherein:
R 1 is CH 2 F; R 2 is hydrogen; and R 3 is methyl.
160 . The compound of claim 159 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is CH 2 F.
161 . The compound of claim 159 wherein:
R 1 is hydrogen; R 2 is methoxymethyl; and R 3 is methyl.
162 . The compound of claim 156 wherein:
R 1 is methoxymethyl; R 2 is hydrogen; and R 3 is methyl.
163 . The compound of claim 156 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methoxymethyl.
164 . The compound of claim 135 wherein the compound is the E isomer.
165 . The compound of claim 164 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by one or more halo or alkoxy.
166 . The compound of claim 165 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy
167 . The compound of claim 165 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl optionally substituted by fluorine.
168 . The compound of claim 165 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by fluorine or alkoxy.
169 . The compound of claim 165 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 3 alkyl; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
170 . The compound of claim 165 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
171 . The compound of claim 170 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and halo; and R 3 is C 1 -C 3 alkyl.
172 . The compound of claim 171 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is C 1 -C 3 alkyl.
173 . The compound of claim 172 wherein:
R 1 is hydrogen; R 2 is selected from the group consisting of hydrogen and fluorine; and R 3 is methyl.
174 . The compound of claim 172 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methyl.
175 . The compound of claim 173 wherein:
R 1 is hydrogen; R 2 is fluorine; and R 3 is methyl.
176 . The compound of claim 165 wherein:
R 1 is halo; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 3 alkyl; and R 3 is C 1 -C 3 alkyl.
177 . The compound of claim 176 wherein:
R 1 is halo; R 2 is halo; and R 3 is C 1 -C 3 alkyl.
178 . The compound of claim 177 wherein:
R 1 is fluorine; R 2 is fluorine; and R 3 is methyl.
179 . The compound of claim 176 wherein:
R 1 is fluorine; R 2 is selected from the group consisting of hydrogen and C 1 -C 3 alkyl; and R 3 is methyl.
180 . The compound of claim 179 wherein:
R 1 is fluorine; R 2 is hydrogen; and R 3 is methyl.
181 . The compound of claim 165 wherein:
R 1 is methyl; R 2 is hydrogen; and R 3 is methyl.
182 . The compound of claim 165 wherein:
R 1 is hydrogen; R 2 is methyl; and R 3 is methyl.
183 . The compound of claim 165 wherein:
R 1 is methyl; R 2 is methyl; and R 3 is methyl.
184 . The compound of claim 164 wherein:
R 1 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; R 2 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy or one or more fluorine; and R 3 is methyl optionally substituted by one or more alkoxy or halo.
185 . The compound of claim 184 wherein:
R 1 is selected from the group consisting of hydrogen and fluorine; R 2 is C 1 -C 3 alkyl substituted by one or more halo; and R 3 is methyl.
186 . The compound of claim 185 wherein:
R 1 is hydrogen; R 2 is CH 2 F; and R 3 is methyl.
187 . The compound of claim 185 wherein:
R 1 is CH 2 F; R 2 is hydrogen; and R 3 is methyl.
188 . The compound of claim 184 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is CH 2 F.
189 . The compound of claim 184 wherein:
R 1 is hydrogen; R 2 is methoxymethyl; and R 3 is methyl.
190 . The compound of claim 184 wherein:
R 1 is methoxymethyl; R 2 is hydrogen; and R 3 is methyl.
191 . The compound of claim 184 wherein:
R 1 is hydrogen; R 2 is hydrogen; and R 3 is methoxymethyl.
192 . A compound of Formula VI
or a pharmaceutically acceptable salt thereof, wherein:
R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
193 . The compound of claim 192 wherein:
R 3 is C 1 -C 5 alkyl substituted by one or more halo.
194 . The compound of claim 193 wherein:
R 3 is C 1 -C 5 alkyl substituted by one or more fluorine.
195 . The compound of claim 193 wherein:
R 3 is methyl substituted by one or more halo.
196 . The compound of claim 195 wherein:
R 3 is methyl substituted by one or more fluorine.
197 . The compound of claim 195 wherein:
R 3 is CH 2 F.
198 . The compound recited in claim 193 wherein:
R 3 is C 1 -C 5 alkyl substituted by alkoxy.
199 . The compound of claim 198 wherein:
R 3 is methoxy methyl.
200 . The compound of claim 193 wherein:
R 3 is C 1 -C 5 alkyl.
201 . The compound of claim 199 wherein:
R 3 is methyl.
202 . A novel intermediate compound selected from:
203 . A compound selected from the group consisting of:
(2S,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S,5Z)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S,5E)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptynoic acid; (2S,5E)-2-amino-2-ethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-2-methoxymethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-2-fluoromethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-2,5-dimethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-5-fluoromethyl-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-2,6-dimethyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-6-fluoromethyl-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-ethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-methoxymethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-fluoromethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2,5-dimethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-5-fluoromethyl-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2,6-dimethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-6-fluoromethyl-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptynoic acid; (2S,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S,5Z)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S,5E)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptynoic acid, dihydrochloride; (2S,5E)-2-amino-2-ethyl-6-fluoro-7-[(-1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-2-methoxymethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-2-fluoromethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-2,5-dimethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-5-fluoromethyl-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-2,6-dimethyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-6-fluoromethyl-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-ethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-methoxymethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-fluoromethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2,5-dimethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-5-fluoromethyl-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2,6-dimethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-6-fluoromethyl-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; and (2S)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptynoic acid, dihydrochloride.
204 . A novel intermediate compound selected from:
4-[(2E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-fluoro-2-pentenyl]-3-methyl-1,2,4-oxadiazol-5(4H)-one; 4-[(2E)-2-fluoro-5-hydroxy-2-pentenyl]-3-methyl-1,2,4-oxadiazol-5(4H)-one; 4-[(2E)-2-fluoro-5-iodo-2-pentenyl]-3-methyl-1,2,4-oxadiazol-5(4H)-one; (3S,6R)-3-[(3E)-4-fluoro-5-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-3-pentenyl]-3,6-dihydro-3-methyl-6-(1-methylethyl)-5-phenyl-2H-1,4-oxazin-2-one; N-[(2E)-5-[(3S,6R)-3,6-dihydro-3-methyl-6-(1-methylethyl)-2-oxo-5-phenyl-2H-1,4-oxazin-3-yl]-2-fluoro-2-pentenyl]ethanimidamide; (5E)-2-amino-6-fluoro-2-methyl-7-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-5-heptenoic acid, methyl ester; (2S,5E)-2-amino-6-fluoro-2-methyl-7-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-5-heptenoic acid, methyl ester; (2S,5E)-2-amino-6-fluoro-7-[[(1E)-1-(hydroxyimino)ethyl]amino]-2-methyl-5-heptenoic acid; (2S,5E)-2-amino-6-fluoro-7-[(1-iminoethyl)amino]-2-methyl-5-heptenoic acid, methyl ester; (2R,5E)-2-amino-6-fluoro-2-methyl-7-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-5-heptenoic acid, methyl ester; (2R,5E)-2-amino-6-fluoro-7-[(1-iminoethyl)amino]-2-methyl-5-heptenoic acid, ethyl ester; (5E)-2-amino-6-fluoro-7-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-5-heptenoic acid, methyl ester; (5E)-2-[[(1Z)-(4-chlorophenyl)methylidene]amino]-6-fluoro-7-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-5-heptenoic acid, methyl ester; (5E)-2-amino-6-fluoro-2-methyl-7-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-5-heptenoic acid, methyl ester; (5E)-2-amino-6-fluoro-7-[(1-iminoethyl)amino]-2-methyl-5-heptenoic acid, methyl ester; Methyl (5E)-7-[(tert-butoxycarbonyl)amino]-2-{[(1Z)-(2,4-dichlorophenyl)methylidene]amino}-5-fluoro-2-methylhept-5-enoate; (5E)-2,7-diamino-5-fluoro-2-methyl-5-heptenoic acid, methyl ester, dihydrochloride; (5E)-2-amino-5-fluoro-7-[(1-iminoethyl)amino]-2-methyl-5-heptenoic acid, methyl ester, monohydrochloride; (5Z)-2-[[(1E)-(2,4-dichlorophenyl)methylidene]amino]-7-[[(1,1-dimethylethoxy)carbonyl]amino]-5-fluoro-2-methyl-5-heptenoic acid, methyl ester; (5Z)-2,7-diamino-5-fluoro-2-methyl-5-heptenoic acid, methyl ester, dihydrochloride; (5Z)-2-amino-5-fluoro-7-[(1-iminoethyl)amino]-2-methyl-5-heptenoic acid, methyl ester, dihydrochloride; 4-[(2Z)-5-hydroxy-2-pentenyl]-3-methyl-1,2,4-oxadiazol-5(4H)-one; (3Z)-5-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-3-pentenyl ester, acetic acid, trifluoro-; 4-[(2Z)-5-[(2R,4S)-3-benzoyl-2-(1,1-dimethylethyl)-4-methyl-5-oxo-4-oxazolidinyl]-2-pentenyl]-3-methyl-1,2,4-oxadiazol-5(4H)-one; 3-Methyl-4-[5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl]-4H-[1,2,4]oxadiazol-5-one; 4-(5-Hydroxy-pent-2-enyl)-3-methyl-4H-[1,2,4]oxadiazol-5-one; Methanesulfonic acid 5-(3-methyl-5-oxo-[1,2,4]oxadiazol-4-yl)-pent-3-enyl ester; 4-(5-Iodo-pent-2-enyl)-3-methyl-4H-[1,2,4]oxadiazol-5-one; Rac-2-Amino-2-methyl-7-(3-methyl-5-oxo-[1,2,4]oxadiazol-4-yl)-hept-5-enoic acid methyl ester; Rac-2-Amino-2-methyl-7-(3-methyl-5-oxo-[1,2,4]oxadiazol-4-yl)-hept-5-enoic acid; (2S,5Z)-2-Amino-2-methyl-7-(3-methyl-5-oxo-[1,2,4]oxadiazol-4-yl)-hept-5-enoic acid methyl ester; (2S,5Z)-7-Acetimidoylamino-2-amino-2-methyl-hept-5-enoic acid methyl ester, dihydrochloride hydrate; (2S,5Z)-2-amino-7-[[(1E)-1-(hydroxyimino)ethyl]amino]-2-methyl-5-heptenoic acid; 4-[(2E)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pentenyl]-3-methyl-1,2,4-oxadiazol-5(4H)-one; 4-[(2E)-5-hydroxy-2-pentenyl]-3-methyl-2,4-oxadiazol-5(4H)-one; (5E)-2-[[(1E)-(3,4-dichlorophenyl)methylidene]amino]-2-methyl-7-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-5-heptenoic acid, methyl ester; (5E)-2-amino-2-methyl-7-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-5-heptenoic acid, methyl ester; and Methyl (5E)-2-amino-7-(ethanimidoylamino)-2-methylhept-5-enoate.
205 . A pharmaceutical composition comprising at least one compound selected from the group consisting of:
(2S,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S,5Z)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S,5E)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2R/S)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptynoic acid; (2S,5E)-2-amino-2-ethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-2-methoxymethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-2-fluoromethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-2,5-dimethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-5-fluoromethyl-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-2,6-dimethyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-6-fluoromethyl-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-ethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-methoxymethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2-fluoromethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2,5-dimethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-5-fluoromethyl-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5Z)-2-amino-2,6-dimethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S,5E)-2-amino-6-fluoromethyl-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid; (2S)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptynoic acid; (2S,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S,5E)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S,5Z)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S,5Z)-2-amino-2-methyl-5,6-difluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R,5Z)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S,5E)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2R/S)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptynoic acid, dihydrochloride; (2S,5E)-2-amino-2-ethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-2-methoxymethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-2-fluoromethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-2,5-dimethyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-5-fluoromethyl-2-methyl-6-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-2,6-dimethyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-6-fluoromethyl-2-methyl-5-fluoro-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-ethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-methoxymethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2-fluoromethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2,5-dimethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-5-fluoromethyl-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5Z)-2-amino-2,6-dimethyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; (2S,5E)-2-amino-6-fluoromethyl-2-methyl-7-[(1-iminoethyl)amino]-5-heptenoic acid, dihydrochloride; and (2S)-2-amino-2-methyl-7-[(1-iminoethyl)amino]-5-heptynoic acid, dihydrochloride.
206 . A compound of Formula VII:
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 4 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and
R 5 is selected from the group consisting of halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
207 . The compound of claim 206 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is selected from the group consisting of halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy.
208 . The compound of claim 206 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen and halo; and R 5 is selected from the group consisting of halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy.
209 . The compound of claim 207 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
210 . The compound of claim 209 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; ‘R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by one or more halo
211 . The compound of claim 208 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 5 is halo.
212 . The compound of claim 211 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 5 is fluorine.
213 . The compound of claim 210 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is C 1 -C 5 alkyl substituted by halo.
214 . The compound of claim 213 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is CH 2 F.
215 . The compound of claim 214 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is hydrogen; and R 5 is CH 2 F.
216 . The compound of claim 208 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is halo; and R 5 is halo.
217 . The compound of claim 208 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is hydrogen; and R 5 is halo.
218 . The compound of claim 217 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is fluorine, and R 5 is fluorine.
219 . The compound of claim 210 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is hydrogen; and R 5 is methyl.
220 . A compound of Formula VIII:
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 4 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and
R 5 is selected from the group consisting of halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
221 . The compound of claim 220 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo, R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is selected from the group consisting of halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy.
222 . The compound of claim 220 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen and halo; and R 5 is selected from the group consisting of halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy.
223 . The compound of claim 221 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
224 . The compound of claim 223 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by one or more halo
225 . The compound of claim 222 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 5 is halo.
226 . The compound of claim 225 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;. R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 5 is fluorine.
227 . The compound of claim 224 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is C 1 -C 5 alkyl substituted by halo.
228 . The compound of claim 227 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is CH 2 F.
229 . The compound of claim 228 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is hydrogen; and R 5 is CH 2 F.
230 . The compound of claim 222 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by a halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is halo; and R 5 is halo.
231 . The compound of claim 221 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is hydrogen; and R 5 is halo.
232 . The compound of claim 231 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is fluorine; and R 5 is fluorine.
233 . The compound of claim 224 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is hydrogen; and R 5 is methyl.
234 . A compound of Formula IX:
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 2 is selected from the group consisting of hydrogen halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo;
R 4 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and
R 5 is selected from the group consisting of halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
235 . The compound of claim 234 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is selected from the group consisting of halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy.
236 . The compound of claim 234 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen and halo; and R 5 is selected from the group consisting of halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy.
237 . The compound of claim 235 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo.
238 . The compound of claim 237 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by one or more halo
239 . The compound of claim 234 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 5 is halo.
240 . The compound of claim 239 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; and R 5 is fluorine.
241 . The compound of claim 238 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is C 1 -C 5 alkyl substituted by halo.
242 . The compound of claim 241 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is selected from the group consisting of hydrogen, halo and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy; and R 5 is CH 2 F.
243 . The compound of claim 242 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is hydrogen; and R 5 is CH 2 F.
244 . The compound of claim 236 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is halo; and R 5 is halo.
245 . The compound of claim 234 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is hydrogen; and R 5 is halo.
246 . The compound of claim 245 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is fluorine; and R 5 is fluorine.
247 . The compound of claim 238 wherein:
R 1 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 2 is selected from the group consisting of hydrogen, halo, and C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 3 is C 1 -C 5 alkyl, said C 1 -C 5 alkyl optionally substituted by halo or alkoxy, said alkoxy optionally substituted by one or more halo; R 4 is hydrogen; and R 5 is methyl.Cited by (0)
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