US2017088549A1PendingUtilityA1
Antibacterial agents
Est. expiryJun 12, 2027(~0.9 yrs left)· nominal 20-yr term from priority
Inventors:Heinz Ernst MoserQing LuPhillip A. PattenDan WangRamesh KasarStephen W. KaldorBrian D. Patterson
C07D 471/04C07D 207/48C07D 309/08C07D 207/08C07D 231/12C07D 207/12C07D 239/70C07D 277/40C07D 333/36C07D 413/04C07D 277/46C07D 211/34C07D 333/06C07D 217/22C07D 333/24C07D 239/88C07D 261/20C07D 239/90C07D 241/52C07D 217/24C07C 2601/14C07D 233/36C07D 207/10C07D 261/08C07D 309/12C07D 277/30C07D 241/12C07D 271/107C07D 309/04C07D 207/16C07D 295/155C07D 239/26C07D 249/08C07D 231/14C07D 333/34C07D 213/36C07C 2601/04C07D 275/02C07D 209/46C07D 213/56C07D 263/58C07D 295/26C07D 205/04C07D 211/94C07D 295/092C07D 211/56C07D 295/15C07D 213/38C07D 207/06C07D 207/46A61P 43/00C07D 207/337C07C 2601/02C07D 295/135C07D 295/096C07D 277/82C07D 211/26C07C 2601/08C07D 213/74C07C 311/08C07D 335/02C07D 231/56C07D 267/10A61P 31/04C07D 213/61C07D 263/34C07D 207/34C07D 285/12C07D 211/38C07D 241/08C07D 233/64C07D 233/26C07D 207/32C07D 211/08C07D 263/32C07D 307/14C07D 239/42C07D 207/09C07D 211/46C07C 259/06C07C 2101/14C07C 2101/04C07C 2101/02C07C 2101/08
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Claims
Abstract
Antibacterial compounds of formula (I) are provided: as well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound having the following formula (I):
or a stereoisomer, pharmaceutically acceptable salt, ester, or prodrug thereof,
wherein:
E is selected from the group consisting of:
(1) H,
(2) substituted or unsubstituted C 1 -C 6 -alkyl,
(3) substituted or unsubstituted C 2 -C 6 -alkenyl,
(4) substituted or unsubstituted C 2 -C 6 -alkynyl,
(5) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(6) substituted or unsubstituted aryl,
(7) substituted or unsubstituted heterocyclyl, and
(8) substituted or unsubstituted heteroaryl;
L is absent or selected from the group consisting of:
(1) substituted or unsubstituted C 1 -C 6 -alkyl,
(2) —(NR 3L ) 0-1 —(CH 2 ) 0-4 —NR 3L —(CH 2 ) 0-4 —,
(3) —(NR 3L ) 0-1 —C(R 1L ,R 2L )—NR 3L —C(R 1L ,R 2L )—,
(4) —C(R 1L ,R 2L )—O—C(R 1L ,R 2L )—,
(5) —(CH 2 ) 0-4 —NR 3L —C(R 1L ,R 2L )—CONH—(CH 2 ) 0-4 —,
(6) —CO—C(R 1L ,R 2L )—NHCO—,
(7) —CONR 3L —,
(8) —NR 3L CO—,
(9) —NR 3L —,
(10) —SO 2 NR 3L —,
(11) —NR 3L —C(═O)—NR 3L —,
(12) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(13) substituted or unsubstituted aryl,
(14) substituted or unsubstituted heterocyclyl, and
(15) substituted or unsubstituted heteroaryl,
wherein:
each R 1L , R 2L , and R 3L is independently selected from the group consisting of:
(a) H,
(b) substituted or unsubstituted C 1 -C 6 -alkyl,
(c) C 1 -C 6 -alkyl substituted with aryl,
(d) C 1 -C 6 -alkyl substituted with heterocyclyl, and
(e) C 1 -C 6 -alkyl substituted with heteroaryl,
or R 1L and R 3L , together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S;
D is absent or selected from the group consisting of:
(1) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(2) substituted or unsubstituted aryl,
(3) substituted or unsubstituted heterocyclyl, and
(4) substituted or unsubstituted heteroaryl;
G is selected from the group consisting of:
(1) —NR 1G C(═O)—,
(2) —C(═O)NR 1G —,
(3) —(CH 2 ) 0-4 NHCH 2 C(═O)NR 1G —,
(4) —CR 2G ═CR 2G —,
(5) —S(═O)—,
(6) —SO 2 —,
(7) —C(R 3G ) 2 —S(═O)—,
(8) —S(═O)—C(R 3G ) 2 —,
(9) —C(R 3G ) 2 —SO 2 —,
(10) —SO 2 —C(R 3G ) 2 —,
(11) —CR 3G ═CR 3G —CR 3G ═CR 3G —,
(12) —C(R 3G ) 2 —,
(13) —CR 3G ═CR 3G —C≡C—,
(14) —C≡C—CR 3G ═CR 3G —,
(15) —C(═O)—C≡C—,
(16) —C≡C—C(═O)—,
(17) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(18) substituted or unsubstituted aryl,
(19) substituted or unsubstituted heterocyclyl, and
(20) substituted or unsubstituted heteroaryl,
wherein:
R 1G is substituted or unsubstituted C 1 -C 6 -alkyl;
each R 2G is independently selected from the group consisting of H, a halogen atom, and substituted or unsubstituted C 1 -C 6 -alkyl, and at least one R 2G is not H; and
R 3G is selected from the group consisting of H, a halogen atom, and substituted or unsubstituted C 1 -C 6 -alkyl;
Y is absent or selected from the group consisting of:
(1) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(2) substituted or unsubstituted aryl,
(3) substituted or unsubstituted heterocyclyl, and
(4) substituted or unsubstituted heteroaryl;
X is selected from the group consisting of:
(1) —(C═O)NR 4 —,
(2) —C 1 -C 6 -alkyl-(C═O)NR 4 —,
(3) —C 2 -C 6 -alkenyl-(C═O)NR 4 —,
(4) —C 2 -C 6 -alkynyl-(C═O)NR 4 —,
(5) —CH 2 NR 4 —,
(6) —SO 2 NR 4 —,
(7) —S(═O)NR 4 —,
(8) —NR 4 C(═O)—, and
(9) —NR 4 —,
or X and A, together with the atoms to which they are attached can form a heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S,
or when Y is a bicyclic substituted or unsubstituted heterocyclyl or heteroaryl, then X is absent;
R 3 is H or substituted or unsubstituted C 1 -C 6 -alkyl, or R 3 and A, together with the atom to which they are attached can form a substituted or unsubstituted 3-10 membered cycloalkyl or a heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring are selected from N, O and S;
R 4 is (1) H or substituted or unsubstituted C 1 -C 6 -alkyl, or (2) R 4 and A, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S, or (3) R 4 and Y, together with the atoms to which they are attached, form a bicyclic substituted or unsubstituted heterocyclyl or heteroaryl;
n is an integer from 0-6;
A is selected from the group consisting of:
(1) H,
(2) —(CH 2 ) 0-4 C(R 1a ,R 2a )(CH 2 ) 0-4 OR 3a ,
(3) —(CH 2 ) 0-4 C(R 1a ,R 2a )N(R 4a ,R 5a ),
(4) —(CH 2 ) 0-4 C(R 1a ,R 2a )N(R 4a )COR 3a ,
(5) —(CH 2 ) 0-4 C(R 1a ,R 2a )NHCON(R 4a ,R 5a ),
(6) —(CH 2 ) 0-4 C(R 1a ,R 2a )NHC(═NH)N(R 4a ,R 5a ),
(7) —CH(R 1a ,R 2a ),
(8) —C≡CH,
(9) —(CH 2 ) 0-4 C(R 1a ,R 2a )CN,
(10) —(CH 2 ) 0-4 C(R 1a ,R 2a )CO 2 R 3a ,
(11) —(CH 2 ) 0-4 C(R 1a ,R 2a )CON(R 4a ,R 5a ),
(12) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(13) substituted or unsubstituted aryl,
(14) substituted or unsubstituted heterocyclyl, and
(15) substituted or unsubstituted heteroaryl,
wherein:
each R 1a , R 2a , R 3a , R 4a , and R 5a is independently selected from the group consisting of:
(a) H,
(b) a halogen atom,
(c) substituted or unsubstituted C 1 -C 6 -alkyl,
(d) substituted or unsubstituted aryl,
(e) substituted or unsubstituted heterocyclyl, and
(f) substituted or unsubstituted heteroaryl,
or R 4a and R 5a together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S;
Q is absent or selected from the group consisting of:
(1) —C(═O)N(R 1 ,R 2 ),
(2) —NHC(═O)N(R 1 ,R 2 ),
(3) —N(OH)C(═O)N(R 1 ,R 2 ),
(4) —CH(OH)C(═O)N(R 1 ,R 2 ),
(5) —CH[N(R 2q , R 3q )]C(═O)N(R 1 ,R 2 ),
(6) —CHR 1q C(═O)N(R 1 , R 2 ),
(7) —CO 2 H,
(8) —C(═O)NHSO 2 R 4q ,
(9) —SO 2 NH 2 ,
(10) —N(OH)C(═O)R 1q ,
(11) —N(OH)SO 2 R 4q ,
(12) —NHSO 2 R 4q ,
(13) —SH,
(14) —CH(SH)(CH 2 ) 0-1 C(═O)N(R 1 ,R 2 ),
(15) —CH(SH)(CH 2 ) 0-1 CO 2 H,
(16) —CH(OH)(CH 2 ) 0-1 CO 2 H,
(17) —CH(SH)CH 2 CO 2 R 1q ,
(18) —CH(OH)(CH 2 )SO 2 NH 2 ,
(19) —CH(CH 2 SH)NHCOR 1q ,
(20) —CH(CH 2 SH)NHSO 2 R 4q ,
(21) —CH(CH 2 SR 5q )CO 2 H,
(22) —CH(CH 2 SH)NHSO 2 NH 2 ,
(23) —CH(CH 2 OH)CO 2 H,
(24) —CH(CH 2 OH)NHSO 2 NH 2 ,
(25) —C(═O)CH 2 CO 2 H,
(26) —C(═O)(CH 2 ) 0-1 CONH 2 ,
(27) —OSO 2 NHR 5q ,
(28) —SO 2 NHNH 2 ,
(29) —P(═O)(═O) 2 ,
and
(33) —N(OH)C(═O)CR 1 R 2 ,
wherein:
R 1 is selected from the group consisting of:
(1) —H,
(2) —OH,
(3) —OC 1 -C 6 -alkyl,
(4) —N(R 2q , R 3q ), and
(5) substituted or unsubstituted C 1 -C 6 -alkyl;
R 2 is selected from the group consisting of:
(1) H,
(2) substituted or unsubstituted C 1 -C 6 -alkyl,
(3) substituted or unsubstituted C 2 -C 6 -alkenyl,
(4) substituted or unsubstituted C 2 -C 6 -alkenyl,
(5) substituted or unsubstituted aryl,
(6) substituted or unsubstituted heterocyclyl, and
(7) substituted or unsubstituted heteroaryl,
or R 1 and R 2 , together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring are selected from N, O and S; and
each R 1q , R 2q , R 3q , R 4q , and R 5q is independently selected from the group consisting of H and C 1 -C 6 alkyl.
2 . A compound of claim 1 wherein G is selected from the group consisting of:
(1) —C≡C—,
(2) —C≡C—C≡C—,
(3) —CR 3G ═CR 3G —C≡C—, and
(4) —C≡C—CR 3G ═CR 3G —.
3 . A compound of claim 2 wherein G is selected from the group consisting of:
(1) —C≡C—,
(2) —C≡C—C≡C—,
(3) —CH═CH—C≡C—, and
(4) —C≡C—CH═CH—.
4 . A compound of claim 3 wherein G is —C≡C—.
5 . A compound of claim 3 wherein G is —C≡C—C≡C—.
6 . A compound of claim 3 wherein G is —CH═CH—C≡C—.
7 . A compound of claim 6 wherein G has the following structure:
8 . A compound of claim 3 wherein G is —C≡C—CH═CH—.
9 . A compound of claim 8 wherein G has the following structure:
10 . A compound of any one of claims 1 - 9 wherein X is —(C═O)NR 4 —.
11 . A compound of claim 10 wherein X is —(C═O)NH—.
12 . A compound of any one of claims 1 - 11 wherein Q is —(C═O)N(R 1 ,R 2 ).
13 . A compound of claim 12 wherein Q is —(C═O)NHOH.
14 . A compound of any one of claims 1 - 13 wherein n is 0.
15 . A compound of any one of claims 1 - 14 wherein R 3 is H.
16 . A compound of any one of claims 1 - 15 wherein Y is substituted or unsubstituted aryl.
17 . A compound of claim 16 wherein Y is substituted or unsubstituted phenyl.
18 . A compound of claim 17 wherein Y is unsubstituted phenyl.
19 . A compound of any one of claims 1 - 18 wherein A is selected from the group consisting of:
(1) —(CH 2 ) 0-4 C(R 1a ,R 2a )(CH 2 ) 0-4 OR 3a ,
(2) —(CH 2 ) 0-4 C(R 1a ,R 2a )N(R 4a ,R 5a ), and
(3) —CH(R 1a ,R 2a ).
20 . A compound of claim 19 wherein A is selected from the group consisting of —CH(CH 3 ) 2 , —CH 2 OH, —CH 2 NH 2 , —CHCH 3 OH, —CHCH 3 NH 2 and —C(CH 3 ) 2 OH.
21 . A compound of claim 19 wherein A is —C(CH 3 ) 2 NH 2 .
22 . A compound of any one of claims 1 - 18 wherein A is selected from the group consisting of:
(1) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(2) substituted or unsubstituted aryl,
(3) substituted or unsubstituted heterocyclyl, and
(4) substituted or unsubstituted heteroaryl.
23 . A compound of claim 22 wherein A is selected from the group consisting of
24 . A compound of any one of claims 1 - 23 wherein R 3 is H and
has the following structure:
25 . A compound of claim 24 wherein A is —CHCH 3 OH or —CHCH 3 NH 2
and has one of the following structures:
26 . A compound of any one of claims 1 - 25 wherein D is present.
27 . A compound of claim 26 wherein D is substituted or unsubstituted heteroaryl.
28 . A compound of claim 27 wherein heteroaryl is selected from the group consisting of:
29 . A compound of claim 26 wherein D is substituted or unsubstituted aryl.
30 . A compound of claim 29 wherein D is substituted or unsubstituted phenyl.
31 . A compound of claim 30 wherein D is unsubstituted phenyl.
32 . A compound of any one of claims 1 - 25 wherein D is absent.
33 . A compound of any one of claims 1 - 32 wherein L is present.
34 . A compound of claim 33 wherein L is substituted or unsubstituted alkyl
35 . A compound of claim 34 wherein wherein L is —CH 3 —.
36 . A compound of claim 33 wherein L is —CH 2 —NH—.
37 . A compound of any one of claims 1 - 32 wherein L is absent.
38 . A compound having the following formula (I):
or a stereoisomer, pharmaceutically acceptable salt, ester, or prodrug thereof,
wherein:
E is selected from the group consisting of:
(1) H,
(2) substituted or unsubstituted C 1 -C 6 -alkyl,
(3) substituted or unsubstituted C 2 -C 6 -alkenyl,
(4) substituted or unsubstituted C 2 -C 6 -alkynyl,
(5) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(6) substituted or unsubstituted aryl,
(7) substituted or unsubstituted heterocyclyl, and
(8) substituted or unsubstituted heteroaryl;
L is absent or selected from the group consisting of:
(1) substituted or unsubstituted C 1 -C 6 -alkyl,
(2) —(NR 3L ) 0-1 —(CH 2 ) 0-4 —NR 3L —(CH 2 ) 0-4 —,
(3) —(NR 3L ) 0-1 —C(R 1L ,R 2L )—NR 3L C(R 1L ,R 2L )—,
(4) —C(R 1L ,R 2L )—O—C(R 1L ,R 2L )—,
(5) —(CH 2 ) 0-4 —NR 3L —C(R 1L , R 2L )—CONH—(CH 2 ) 0-4 —,
(6) —CO—C(R 1L ,R 2L )—NHCO—,
(7) —CONR 3L —,
(8) —NR 3L CO—,
(9) —NR 3L —,
(10) —SO 2 NR 3L —,
(11) —NR 3L —C(═O)—NR 3L —,
(12) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(13) substituted or unsubstituted aryl,
(14) substituted or unsubstituted heterocyclyl, and
(15) substituted or unsubstituted heteroaryl,
wherein:
each R 1L , R 2L , and R 3L is independently selected from the group consisting of:
(a) H,
(b) substituted or unsubstituted C 1 -C 6 -alkyl,
(c) C 1 -C 6 -alkyl substituted with aryl,
(d) C 1 -C 6 -alkyl substituted with heterocyclyl, and
(e) C 1 -C 6 -alkyl substituted with heteroaryl,
or R 1L and R 3L , together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S;
D is absent or selected from the group consisting of:
(1) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(2) substituted or unsubstituted aryl,
(3) substituted or unsubstituted heterocyclyl, and
(4) substituted or unsubstituted heteroaryl;
G is selected from the group consisting of:
(1) —(CH 2 ) 0-4 —O—(CH 2 ) 0-4 —,
(2) —(CH 2 ) 0-4 —S—(CH 2 ) 0-4 —,
(3) —(CH 2 ) 0-4 —NR 1G —(CH 2 ) 0-4 —,
(4) —C(═O)—,
(5) —NR 1G C(═O)—,
(6) —C(═O)NR 1G —,
(7) —(CH 2 ) 0-4 NHCH 2 C(═O)NR 1G —,
(8) —C≡C—,
(9) —C≡C—C≡C—,
(10) —CR 2G ═CR 2G —,
(11) —S(═O)—,
(12) —SO 2 —,
(13) —C(R 3G ) 2 —S(═O)—,
(14) —S(═O)—C(R 3G ) 2 —,
(15) —C(R 3G ) 2 —SO 2 —,
(16) —SO 2 —C(R 3G ) 2 —,
(17) —CR 3G ═CR 3G —CR 3G ═CR 3G —,
(18) —C(R 3G ) 2 —,
(19) —CR 3G ═CR 3G —C≡C—,
(20) —C≡C—CR 3G ═CR 3G —,
(21) —C(═O)—C≡C—,
(22) —C≡C—C(═O)—,
(23) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(24) substituted or unsubstituted aryl,
(25) substituted or unsubstituted heterocyclyl, and
(26) substituted or unsubstituted heteroaryl,
wherein:
R 1G is substituted or unsubstituted C 1 -C 6 -alkyl;
each R 2G and R 3G is independently selected from the group consisting of H, a halogen atom, and substituted or unsubstituted C 1 -C 6 -alkyl;
Y is absent or selected from the group consisting of:
(1) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(2) substituted or unsubstituted aryl,
(3) substituted or unsubstituted heterocyclyl, and
(4) substituted or unsubstituted heteroaryl;
X is selected from the group consisting of:
(1) —(C═O)NR 4 —,
(2) —C 1 -C 6 -alkyl-(C═O)NR 4 —,
(3) —C 2 -C 6 -alkenyl-(C═O)NR 4 —,
(4) —C 2 -C 6 -alkynyl-(C═O)NR 4 —,
(5) —CH 2 NR 4 —,
(6) —SO 2 NR 4 —,
(7) —S(═O)NR 4 —,
(8) —NR 4 C(═O)—, and
(9) —NR 4 —,
or X and A, together with the atoms to which they are attached can form a heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S,
or when Y is a bicyclic substituted or unsubstituted heterocyclyl or heteroaryl, then X is absent;
R 3 is H or substituted or unsubstituted C 1 -C 6 -alkyl, or R 3 and A, together with the atom to which they are attached can form a substituted or unsubstituted 3-10 membered cycloalkyl or a heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring are selected from N, O and S;
R 4 is (1) H or substituted or unsubstituted C 1 -C 6 -alkyl, or (2) R 4 and A, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S, or (3) R 4 and Y, together with the atoms to which they are attached, form a bicyclic substituted or unsubstituted heterocyclyl or heteroaryl;
n is an integer from 0-6;
A is selected from the group consisting of:
(1) —C(R 1a ,R 2a )OR 3a ,
(2) —C(R 1a ,R 2a )N(R 4a ,R 5a ),
(3) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(4) substituted or unsubstituted aryl,
(5) substituted or unsubstituted heterocyclyl, and
(6) substituted or unsubstituted heteroaryl,
wherein:
each R 1a and R 2a is independently selected from the group consisting of substituted or unsubstituted C 1 -C 6 -alkyl;
each R 1a , R 4a , and R 5a is independently selected from the group consisting of:
(a) H,
(b) a halogen atom,
(c) substituted or unsubstituted C 1 -C 6 -alkyl,
(d) substituted or unsubstituted aryl,
(e) substituted or unsubstituted heterocyclyl, and
(f) substituted or unsubstituted heteroaryl,
or R 4a and R 5a together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S; and
when A is —C(R 1a ,R 2a )OR 3a , the compound is not 2-{[(4′-ethyl-1,1′-biphenyl-4-yl)carbonyl]amino}-3-hydroxy-3-methylbutanoic acid, 4′-ethyl-N-{2-hydroxy-1-[(hydroxyamino) carbonyl]-2-methylpropyl}-1,1′-biphenyl-4-carboxamide or N-{2-hydroxy-1-[(hydroxyamino)carbonyl]-2-methylpropyl}-4-(phenylethynyl)benzamide;
Q is absent or selected from the group consisting of:
(1) —C(═O)N(R 1 ,R 2 ),
(2) —NHC(═O)N(R 1 ,R 2 ),
(3) —N(OH)C(═O)N(R 1 ,R 2 ),
(4) —CH(OH)C(═O)N(R 1 ,R 2 ),
(5) —CH[N(R 2q , R 3q )]C(═O)N(R 1 ,R 2 ),
(6) —CHR 1q C(═O)N(R 1 , R 2 ),
(7) —CO 2 H,
(8) —C(═O)NHSO 2 R 4q ,
(9) —SO 2 NH 2 ,
(10) —N(OH)C(═O)R 1g ,
(11) —N(OH)SO 2 R 4q ,
(12) —NHSO 2 R 4q ,
(13) —SH,
(14) —CH(SH)(CH 2 ) 0-4 C(═O)N(R 1 ,R 2 ),
(15) —CH(SH)(CH 2 ) 0-1 CO 2 H,
(16) —CH(OH)(CH 2 ) 0-1 CO 2 H,
(17) —CH(SH)CH 2 CO 2 R 1q ,
(18) —CH(OH)(CH 2 )SO 2 NH 2 ,
(19) —CH(CH 2 SH)NHCOR 1q ,
(20) —CH(CH 2 SH)NHSO 2 R 4q ,
(21) —CH(CH 2 SR 5q )CO 2 H,
(22) —CH(CH 2 SH)NHSO 2 NH 2 ,
(23) —CH(CH 2 OH)CO 2 H,
(24) —CH(CH 2 OH)NHSO 2 NH 2 ,
(25) —C(═O)CH 2 CO 2 H,
(26) —C(═O)(CH 2 ) 0-1 CONH 2 ,
(27) —OSO 2 NHR 5q ,
(28) —SO 2 NHNH 2 ,
(29) —P(═O)(OH) 2 ,
and
(33) —N(OH)C(═O)CR 1 R 2 ,
wherein:
R 1 is selected from the group consisting of:
(1) —H,
(2) —OH,
(3) —OC 1 -C 6 -alkyl,
(4) —N(R 2q , R 3q ), and
(5) substituted or unsubstituted C 1 -C 6 -alkyl;
R 2 is selected from the group consisting of:
(1) H,
(2) substituted or unsubstituted C 1 -C 6 -alkyl,
(3) substituted or unsubstituted C 2 -C 6 -alkenyl,
(4) substituted or unsubstituted C 2 -C 6 -alkenyl,
(5) substituted or unsubstituted aryl,
(6) substituted or unsubstituted heterocyclyl, and
(7) substituted or unsubstituted heteroaryl,
or R 1 and R 2 , together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring are selected from N, O and S; and
each R 1q , R 2q , R 3q , R 4q , and R 5q is independently selected from the group consisting of H and C 1 -C 6 alkyl.
39 . A compound of claim 38 wherein A is —C(R 1a ,R 2a )N(R 4a ,R 5a ).
40 . A compound of claim 39 wherein A is —C(CH 3 ) 2 NH 2 .
41 . A compound of claim 38 wherein A is —C(R 1a ,R 2a )OR 3a .
42 . A compound of claim 38 wherein A is selected from the group consisting of:
(1) substituted or unsubstituted C 3 -C 10 -cycloalkyl,
(2) substituted or unsubstituted aryl,
(3) substituted or unsubstituted heterocyclyl, and
(4) substituted or unsubstituted heteroaryl.
43 . A compound of claim 42 wherein A is selected from the group consisting of
44 . A compound of any one of claims 38 - 43 wherein R 3 is H and
has the following structure:
45 . A compound of any one of claims 38 - 44 wherein G is selected from the group consisting of:
(1) —C≡C—,
(2) —C≡C—C≡C—,
(3) —CR 3G ═CR 3G —C≡C—, and
(4) —C≡C—CR 3G ═CR 3G —.
46 . A compound of claim 45 wherein G is selected from the group consisting of:
(1) —C≡C—,
(2) —C≡C—C≡C—,
(3) —CH═CH—C≡C—, and
(4) —C≡C—CH═CH—.
47 . A compound of claim 46 wherein G is —C≡C—.
48 . A compound of claim 46 wherein G is —C≡C—C≡C—C≡C—.
49 . A compound of claim 46 wherein G is —CH═CH—C≡C—.
50 . A compound of claim 49 wherein G has the following structure:
51 . A compound of claim 46 wherein G is —C≡C—CH═CH—.
52 . A compound of claim 51 wherein G has the following structure:
53 . A compound of any one of claims 38 - 52 wherein X is —(C═O)NR 4 —.
54 . A compound of claim 53 wherein X is —(C═O)NH—.
55 . A compound of any one of claims 38 - 54 wherein Q is —(C═O)N(R 1 ,R 2 ).
56 . A compound of claim 55 wherein Q is —(C═O)NHOH.
57 . A compound of any one of claims 38 - 56 wherein n is 0.
58 . A compound of any one of claims 38 - 57 wherein R 3 is H.
59 . A compound of any one of claims 38 - 58 wherein Y is substituted or unsubstituted aryl.
60 . A compound of claim 59 wherein Y is substituted or unsubstituted phenyl.
61 . A compound of claim 60 wherein Y is unsubstituted phenyl.
62 . A compound of any one of claims 38 - 61 wherein D is present.
63 . A compound of claim 62 wherein D is substituted or unsubstituted heteroaryl.
64 . A compound of claim 63 wherein heteroaryl is selected from the group consisting of:
65 . A compound of claim 62 wherein D is substituted or unsubstituted aryl.
66 . A compound of claim 65 wherein D is substituted or unsubstituted phenyl.
67 . A compound of claim 66 wherein D is unsubstituted phenyl.
68 . A compound of any one of claims 38 - 61 wherein D is absent.
69 . A compound of any one of claims 38 - 68 wherein L is present.
70 . A compound of claim 69 wherein L is substituted or unsubstituted alkyl
71 . A compound of claim 70 wherein wherein L is —CH 3 —.
72 . A compound of claim 69 wherein L is —CH 2 —NH—.
73 . A compound of any one of claims 38 - 68 wherein L is absent.
74 . A pharmaceutical composition comprising a compound of any one of claims 1 - 73 and a pharmaceutically acceptable carrier or diluent.
75 . A method for treating a subject with a gram-negative bacterial infection comprising administering to the subject in need thereof an antibacterially effective amount of a compound of any one of claims 1 - 73 or a pharmaceutical composition of claim 74 .
76 . A method for treating a subject with a gram-negative bacterial infection comprising co-administering to the subject in need thereof an antibacterially effective amount of a compound of any one of claims 1 - 73 or a pharmaceutical composition of claim 74 and a second antibacterial agent.Cited by (0)
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