Isoxazolinone antibacterial agents

Details Isoxazolinone antibacterial agents Isoxazolinone antibacterial agents

2001-02-13

2002-07-16

McKane, Joseph K. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

C544S058200, C544S060000, C544S137000, C544S229000, C546S209000, C548S243000, C548S255000, C514S063000, C514S236800, C514S252010

Reexamination Certificate

active

06420349

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention is directed toward new isoxazolinones, methods for their use, and processes for their production. The present invention provides for a compound represented by the general formula
or a pharmaceutically acceptable salt thereof wherein:
R
1
is
a) H,
b) C
1-8
alkyl optionally substituted with one or more F, Cl, OH, C
1-8
alkoxy, or C
1-8
acyloxy,
c) C
3-6
cycloalkyl, or
d) C
1-8
alkoxy;
L is oxygen or sulfur;
A is
c) a 5-membered heteroaromatic moiety having one to three hetero atoms selected from the group consisting of S, N, and O, wherein the 5-membered heteroaromatic moiety is bonded via a carbon atom and can additionally have a fused-on benzene or naphthyl ring, and wherein the heteroaromatic moiety is optionally substituted with one to three R
8
,
d) a 6-membered heteroaromatic moiety having at least one nitrogen atom, wherein the heteroaromatic moiety is bonded via a carbon atom, wherein the 6-membered heteroaromatic moiety can additionally have a fused-on benzene or naphthyl ring, wherein the heteroaromatic moiety is optionally substituted with one to three R
9
,
e) a &bgr;-carbolin-3-yl, or indolizinyl bonded via the 6-membered ring, optionally substituted with one to three R
9
,
wherein R
2
and R
3
are each independently
a) H,
b) F,
c) Cl,
d) Br,
e) C
1-6
alkyl,
f) NO
2
,
g) I,
h) C
1-6
alkoxy,
i) OH
j) amino,
k) cyano, or
l) R
2
and R
3
taken together are —O(CH
2
)
h
—O;
wherein R
4
is
a) H,
b) C
1-2
alkyl,
c) F, or
d) OH;
R
5
is
a) H,
b) CF
3
,
c) C
1-3
alkyl optionally substituted with one or more halo,
d) phenyl optionally substituted with one or more halo,
e) R
5
and R
6
taken together are a 5-, 6-, or 7-membered ring of the formula,
 in which D is S, O or NR
86
in which R
86
is H or C
1-6
alkyl or
g) R
5
and R
6
taken together are —(CH
2
)
k
—, when R
7
is an electron-withdrawing group;
R
6
and R
7
at each occurrence are the same or different and are
a) an electron-withdrawing group,
b) H,
c) CF
3
,
d) C
1-3
alkyl optionally substituted with one halo,
e) phenyl, provided at least one of R
6
and R
7
is an electron-withdrawing group, or
f) R
6
and R
7
taken together are a 5-, 6-, or 7-membered ring of the formula,
U is
a) CH
2
,
b) O,
c) S or,
d) NR
16
;
R
16
is
a) H or
b) C
1-5
alkyl;
wherein R
8
is
a) carboxyl,
b) halo,
c) —CN,
d) mercapto,
e) formyl,
f CF
3
,
g) NO
2
,
h) C
1-6
alkoxy,
i) C
1-6
alkoxycarbonyl,
j) C
1-6
alkythio,
k) C
1-6
acyl,
l) —NR
17
R
18
,
 in which R
87
is H or C
1-6
alkyl,
n) C
1-6
alkyl optionally substituted with OH, sulfamoyl, C
1-5
alkoxy, C
1-5
acyl, or —NR
17
R
18
,
o) C
2-8
alkyl optionally substituted with one or two R
19
,
p) phenyl optionally substituted with one or two R
19
,
q) a 5- or 6-membered saturated or unsaturated heterocyclic moiety having one to three atoms selected from the group consisting of S, N, and O, optionally substituted with one or two R
19
, or
R
17
and R
18
at each occurrence are the same or different and are
a) H,
b) C
1-4
alkyl,
c) C
5-6
cycloalkyl, or
d) R
17
and R
18
taken together with the nitrogen atom is a 5- or 6-membered saturated or unsaturated heterocyclic moiety which optionally has a further hetero atom selected from the group consisting of S, N, O, and can in turn be optionally substituted with, including on the further nitrogen atom, C
1-3
alkyl, formyl, a 5- or 6-membered heteroaromatic moiety containing 1-3 O, N or S,
 in which R
88
and R
89
are each independently hydrogen or C
1-6
alkyl, SO
2
R
90
in which R
90
is H or C
1-6
alkyl, or C
1-3
acyl optionally substituted with 1 or more F, Cl or OH;
R
19
is
a) carboxyl,
b) halo,
c) —CN,
d) mercapto,
e) formyl,
f) CF
3
,
g) NO
2
,
h) C
1-6
alkoxy,
i) C
1-6
alkoxycarbonyl,
i) C
1-6
alkythio,
k) C
1-6
acyl,
l) C
1-6
alkyl optionally substituted with OH, C
1-5
alkoxy, C
1-5
acyl, or —NR
17
R
18
,
m) phenyl,
n) —C(═O)NR
20
R
21
,
o) —N R
17
R
18
,
p) —N(R
20
)(—SO
2
R
22
),
q) —SO
2
—NR
20
R
21
, or
r) —S(═O)
i
R
22
;
R
20
and R
21
at each occurrence are the same or different and are
a) H,
b) C
1-6
alkyl, or
c) phenyl;
R
22
is
a) C
1-4
alkyl, or
b) phenyl optionally substituted with C
1-4
alkyl;
wherein R
9
is
a) carboxyl,
b) halo,
c) —CN,
d) mercapto,
e) formyl,
f) CF
3
,
g) NO
2
,
h) C
1-6
alkoxy,
i) C
1-6
alkoxycarbonyl,
j) C
1-6
alkythio,
k) C
1-6
acyl,
l) —NR
23
R
24
,
m) C
1-6
alkyl optionally substituted with OH, C
1-5
alkoxy, C
1-5
acyl, or —NR
23
R
24
,
n) C
2-8
alkenylphenyl optionally substituted with one or two R
25
,
o) phenyl optionally substituted with one or two R
25
,
p) a 5- or 6-membered saturated or unsaturated heterocyclic moiety having one to three atoms selected from the group consisting of S, N, and O, optionally substituted with one or two R
25
, or
R
23
and R
24
at each occurrence are the same or different and are
a) H,
b) formyl,
c) C
1-4
alkyl,
d) C
1-4
acyl,
e) phenyl,
f) C
3-6
cycloalkyl, or
g) R
23
and R
24
taken together with the nitrogen atom is a 5- or 6-membered saturated heterocyclic moiety which optionally has a further hetero atom selected from the group consisting of S, N, O, and can in turn be optionally substituted with, including on the further nitrogen atom, phenyl, pyrimidyl, C
1-3
alkyl, or C
1-3
acyl;
R
25
is
a) carboxyl,
b) halo,
c) —CN,
d) mercapto,
e) formyl,
f) CF
3
,
g) NO
2
,
h) C
1-6
alkoxy,
i) C
1-6
alkoxycarbonyl,
j) C
1-6
alkythio,
k) C
1-6
acyl,
l) phenyl,
m) C
1-6
alkyl optionally substituted with OH, azido, C
1-5
alkoxy, C
1-5
acyl, —NR
32
R
33
, —SR
34
, —O—SO
2
R
35
, or
n) —C(═O)NR
26
R
27
,
o) —NR
23
R
24
,
p) —N(R
26
)(—SO
2
R
22
),
q) —SO
2
—NR
26
R
27
, or
r) —S(═O)
i
R
22
,
s) —CH═N—R
28
, or
t) —CH(OH)—SO
3
R
31
;
R
22
is the same as defined above;
R
26
and R
27
at each occurrence are the same or different and are
a) H,
b) C
1-6
alkyl,
c) phenyl, or
d) tolyl;
R
28
is
a) OH,
b) benzyloxy,
c) —NH—C(═O)—NH
2
,
d) —NH—C(═S)—NH
2
, or
e) —NH—C(═NH)—NR
29
R
30
;
R
29
and R
30
at each occurrence are the same or different and are
a) H,or
b) C
1-4
alkyl optionally substituted with phenyl or pyridyl;
R
31
is
a) H, or
b) a sodium ion;
R
32
and R
33
at each occurrence are the same or different and are
a) H,
b) formyl,
c) C
1-4
alkyl,
d) C
1-4
acyl,
e) phenyl,
f) C
3-6
cycloalkyl,
g) R
32
and R
33
taken together are a 5- or 6-membered saturated heterocyclic moiety having one to three atoms selected from the group consisting of S, N, O, optionally substituted with, including on the nitrogen atom, phenyl, pyrimidyl, C
1-3
alkyl, or C
1-3
acyl,
h) —P(O)(OR
37
)(OR
38
), or
i) —SO
2
—R
39
;
R
34
is
R
35
is C
1-3
alkyl;
R
36
is
a) C
1-6
alkoxycarbonyl, or
b) carboxyl;
R
37
and R
38
at each occurrence are the same or different and are
a) H,or
b) C
1-3
alkyl;
R
39
is
a) methyl,
b) phenyl, or
c) tolyl;
wherein K is
a) O,
b) S, or
c) NR
40
in which R
40
is hydrogen, formyl, C
1-4
alkyl, C
1-4
acyl, phenyl, C
3-6
cycloalkyl, —P(O)(OR
37
)(OR
38
) or —SO
2
—R
39
in which R
37
, R
38
and R
39
are as defined above;
R
10
, R
11
, R
12
, R
13
, R
14
and R
15
at each occurrence are the same or different and are
a) H,
b) formyl,
c) carboxyl,
d) C
1-6
alkoxycarbonyl,
e) C
1-8
alkyl,
f) C
2-8
alkenyl,
wherein the substitutents (e) and (f) can be optionally substituted with OH, halo, C
1-6
alkoxyl, C
1-6
acyl, C
1-6
alkylthio or C
1-6
alkoxycarbonyl, or phenyl optionally substituted with halo,
g) an aromatic moiety having 6 to 10 carbon atoms optionally substituted with carboxyl, halo, —CN, formyl, CF
3
, NO
2
, C
1-6
alkyl, C
1-6
alkoxy, C
1-6
acyl, C
1-6
alkylthio, or C
1-6
alkoxycarbonyl;
h) —NR
42
R
43
,
i) OR
44
,
j) —S(═O)
i
—R
45
,
k) —SO
2
—N(R
46
)(R
47
), or
l) a radical of the following formulas:
R
19
is the same as defined above;
T is
a) O,
b) S, or
c) SO
2
;
R
42
and R
43
at each occurrence are the same or different and are
a) H,
b) C
3-6
cycloalkyl,
c) phenyl,
d) C
1-6
acyl,
e) C
1-8
alkyl optionally subst

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