IP Library Granted Patent US 9,511,073
Granted Patent B2
US 9,511,073 · App. 14/112,735 · Granted Dec 6, 2016

Aromatic amides and uses thereof

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Quick Facts
Patent No.
US 9,511,073
App. No.
14/112,735
Granted
Dec 6, 2016
Kind
B2
Abstract

The present invention provides compounds of Formula (I): and salts, racemates, isomers, diastereoisomers, enantiomers, hydrates, solvates, N-oxides, pharmaceutically acceptable derivatives or prodrugs thereof. Also provided the use of these compounds as antibacterials, compositions comprising them and processes for their manufacture.

Claims (408)

1. A compound of Formula (I):

or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide, or prodrug thereof wherein

W is a substituted C 6-10 -membered monocyclic or fused bicyclic aryl group or an optionally substituted 5-6-membered monocyclic heteroaryl or a 9-membered fused bicyclic heteroaryl group;

R 1 and R 2 are each independently selected from halo or H;

R 3 is selected from the group consisting of C t alkyl-R 4 , C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6 aryl, and 5-6 membered heterocyclyl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl may be optionally substituted with one or more R 4 or R 5 groups;

t is an integer selected from 0, 1, 2 and 3;

R 3′ is H;

R 4 is selected from the group consisting of C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl, C 1-6 alkylheterocyclyl, OR 6 , (C═O)R 6 , O(C═O)R 6 , C(═O)OR 6 , N(R 6 ) 2 , NR 6 C(═O)R 5 , C(═O)N(R 6 ) 2 , NR 6 C(═O)OR 5 , OC(═O)N(R 6 ) 2 , C(═O)NH—NHC(═O)R 5 , NHC(═O)NHC 1-6 alkyl, NHS(O) x R 5 , S(O) x R 5 , OS(O) x R 5 , OP(═O)(OR 6 ) 2 and P(═O)(OR 6 ) 2 wherein each C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocycly may be further optionally substituted with one or more substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—HNC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl;

each R 5 is selected from C 1 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

each R 6 is independently selected from H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl; and

wherein each R 5 and R 6 independently may be optionally substituted with one or more substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—NHC(═O)R 7 , S(O) x R 7 , OS(O)R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl; and

x is 0 or an integer from 1 to 2.

2. A compound according to claim 1 wherein W is an optionally substituted 5-6-membered monocyclic heteroaryl or a 9-membered fused bicyclic heteroaryl group.

3. A compound of Formula (Ia):

or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide, or prodrug thereof wherein

X and Y are each independently a heteroatom selected from O, N and S or a carbon atom having an optional substituent;

Z is a heteroatom selected from O, N and S or is C—B;

A is selected from H, halo, optionally substituted C 6-10 aryl, optionally substituted 4-10 membered heterocyclyl or A together with B and the carbon atoms to which they are respectively attached join to form an optionally substituted 6-membered fused ring system;

B is selected from H, halo, optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl or B together with A and the carbon atoms to which they are respectively attached join to form an optionally substituted 6-membered fused ring system;

R 1 and R 2 are each independently selected from halo or H;

R 3 is selected from the group consisting of C t alkyl-R 4 , C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6 aryl, and 5-6 membered heterocyclyl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl may be optionally substituted with one or more R 4 or R 5 groups;

t is an integer selected from 0, 1, 2 or 3;

R 4 is selected from the group consisting of C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl, C 1-6 alkylheterocyclyl, OR 6 , (C═O)R 6 , O(C═O)R 6 , C(═O)OR 6 , N(R 6 ) 2 , NR 6 C(═O)R 5 , C(═O)N(R 6 ) 2 , NR 6 C(═O)OR 5 , OC(═O)N(R 6 ) 2 , C(═O)NH—NHC(═O)R 5 , NHC(═O)NHC 1-6 alkyl, NHS(O) x R 5 , S(O) x R 5 , OS(O) x R 5 , OP(═O)(OR 6 ) 2 and P(═O)(OR 6 ) 2 wherein each C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl, and C 1-6 alkylheterocyclyl may be further optionally substituted with one or more substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—HNC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H and C 1-3 alkyl;

each R 5 is optionally substituted and is selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

each R 6 is independently selected from H or is optionally substituted C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

wherein each R 5 and R 6 independently may be further optionally substituted with one or more optional substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—NHC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H and C 1-3 alkyl;

and

x is 0 or an integer from 1 to 2.

4. A compound according to claim 3 wherein A is an optionally substituted C 6 aryl or an optionally substituted 5-6 membered heteroaryl containing one, two, three or four heteroatoms independently selected from O, N and S.

5. A compound according to claim 1 wherein R 3 is selected from C t alkyl-R 4 , and C 2-6 alkenyl where each alkyl and alkenyl group may be optionally substituted with one or more R 4 groups and t is an integer selected from 1, 2 and 3.

6. A compound according to claim 1 wherein R 3 is C t alkyl-R 4 and t is 1, 2 or 3.

7. A compound according to claim 1 wherein R 4 is selected from OR 6 , (C═O)R 6 , O(C═O)R 6 , C(═O)OR 6 , N(R 6 ) 2 , NR 6 C(═O)R 5 , C(═O)N(R 6 ) 2 , NR 6 C(═O)OR 5 , OC(═O)N(R 6 ) 2 , C(═O)NH—NHC(═O)R 5 , NHC(═O)NHC 1-6 alkyl, NHS(O) x R 5 , S(O) x R 5 , OS(O) x R 5 , OP(═O)(OR 6 ) 2 and P(═O)(OR 6 ) 2 where R 5 and R 6 are as defined in claim 1 .

8. A compound according to claim 1 in the form of a racemate, a single enantiomer or mixtures thereof.

9. A compound of general Formula (II):

or a salt, diastereoisomer, hydrate, solvate, N-oxide, or prodrug thereof wherein

X and Y are each independently a heteroatom selected from O, N and S or a carbon atom having an optional substituent;

Z is a heteroatom selected from O, N and S or is C—B;

A is selected from H, halo, optionally substituted C 6-10 aryl, optionally substituted 4-10 membered heterocyclyl or A together with B and the carbon atoms to which they are respectively attached join to form an optionally substituted 6-membered fused ring system;

B is selected from H, halo, optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl or B together with A and the carbon atoms to which they are respectively attached join to form an optionally substituted 6-membered fused ring system;

R 1 and R 2 are each independently selected from halo or H;

R 3 is selected from the group consisting of C t alkyl-R 4 , C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6 aryl, and 5-6 membered heterocyclyl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl may be optionally substituted with one or more R 4 or R 5 groups;

t is an integer selected from 0, 1, 2 or 3;

R 4 is selected from the group consisting of C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl, C 1-6 alkylheterocyclyl, OR 6 , (C═O)R 6 , O(C═O)R 6 , C(═O)OR 6 , N(R 6 ) 2 , NR 6 C(═O)R 5 , C(═O)N(R 6 ) 2 , NR 6 C(═O)OR 5 , OC(═O)N(R 6 ) 2 , C(═O)NH—NHC(═O)R 5 , NHC(═O)NHC 1-6 alkyl, NHS(O) x R 5 , S(O) x R 5 , OS(O) x R 5 , OP(═O)(OR 6 ) 2 and P(═O)(OR 6 ) 2 wherein each C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocycly may be further optionally substituted with one or more substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—HNC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl;

each R 5 is optionally substituted and is selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

each R 6 is independently selected from H or is optionally substituted C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

wherein each R 5 and R 6 independently may be further optionally substituted with one or more optional substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—NHC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H and C 1-3 alkyl; and

x is 0 or an integer from 1 to 2.

10. A compound selected from the group consisting of:

ethyl 2-(3-carbamoyl-2,4-difluorophenoxy)-2-(4-(4-chlorophenyl)oxazol-2-yl)acetate;

3-(1-(4-(4-chlorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

ethyl 2-(3-carbamoyl-2,4-difluorophenoxy)-2-(4-(4-chlorophenyl)thiazol-2-yl)acetate;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(4-(4-chlorophenyl)oxazol-2-yl)acetic acid;

3-(1-(4-(4-chlorophenyl)thiazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(dimethylamino)-2-oxoethoxy)-2,6-difluorobenzamide;

3-(1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(methylamino)-2-oxoethoxy)-2,6-difluorobenzamide;

2-(5-bromo-4-(4-chlorophenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(S)-3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-chlorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(2-amino-1-(4-(4-chlorophenyl)thiazol-2-yl)-2-oxoethoxy)-2,6-difluorobenzamide;

3-(1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(4-methylpiperazin-1-yl)-2-oxoethoxy)-2,6-difluorobenzamide;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(5-chloro-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethyl acetate;

3-(1-(5-chloro-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(5-chloro-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethyl methanesulfonate;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(5-chloro-4-(4-chlorophenyl)oxazol-2-yl)ethyl acetate;

3-(1-(5-chloro-4-(4-chlorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(5-chloro-4-(4-chlorophenyl)oxazol-2-yl)ethyl methanesulfonate;

3-(1-(5-chloro-4-(4-chlorophenyl)oxazol-2-yl)-2-(methylamino)-2-oxoethoxy)-2,6-difluorobenzamide;

3-(1-(5-chloro-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(methylamino)-2-oxoethoxy)-2,6-difluorobenzamide;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(5-chloro-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethyl carbamate;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(5-chloro-4-(4-chlorophenyl)oxazol-2-yl)acetic acid;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(5-chloro-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethyl ethyl succinate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl 2-(dimethylamino)acetate;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(5-chloro-4-(4-chlorophenyl)oxazol-2-yl)ethyl 2-((tert-butoxycarbonyl)(methyl)amino)acetate;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(5-chloro-4-(4-chlorophenyl)oxazol-2-yl)ethyl 2-(methylamino)acetate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl 2-(1,3-dioxoisoindolin-2-yl)acetate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl 2-((tert-butoxycarbonyl)(methyl)amino)acetate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl 2-(methylamino)acetate;

2-(5-allyl-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl 3-(1,3-dioxoisoindolin-2-yl)propanoate;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(5-propyl-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethyl acetate;

3-(1-(5-allyl-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2,6-difluoro-3-(2-hydroxy-1-(5-propyl-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)benzamide;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl 2-(1H-pyrrol-1-yl)acetate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl 4-(1,3-dioxoisoindolin-2-yl)butanoate;

allyl (2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl) succinate;

diallyl (2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl) phosphate;

3-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-(3-carbamoyl-2,4-difluorophenoxy)propyl acetate;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-hydroxypropoxy)-2,6-difluorobenzamide;

4-(2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)-4-oxobutanoic acid;

allyl (2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl) hydrogen phosphate;

2-(5-bromo-4-(4-cyanophenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

3-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-(3-carbamoyl-2,4-difluorophenoxy)propanoic acid;

2-(5-bromo-4-(5-(trifluoromethyl)pyridin-2-yl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

3-(1-(5-bromo-4-(5-(trifluoromethyl)pyridin-2-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-cyanophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl dihydrogen phosphate;

2-(5-bromo-4-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

3-(1-(5-bromo-4-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

ethyl 2-(2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)acetate;

3-(1-(5-bromo-4-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2-(2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)acetic acid;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-(methylamino)-3-oxopropoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-(dimethylamino)-3-oxopropoxy)-2,6-difluorobenzamide;

4-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-4-(3-carbamoyl-2,4-difluorophenoxy)butyl acetate;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-4-hydroxybutoxy)-2,6-difluorobenzamide;

4-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-4-(3-carbamoyl-2,4-difluorophenoxy)butanoic acid;

3-(4-(2-acetylhydrazinyl)-1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-4-oxobutoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-4-(methylamino)-4-oxobutoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-4-(dimethylamino)-4-oxobutoxy)-2,6-difluorobenzamide;

3-(3-amino-1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)propoxy)-2,6-difluorobenzamide;

3-(3-amino-1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-oxopropoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)propoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-(dimethylamino)propoxy)-2,6-difluorobenzamide;

3-((5-bromo-4-(4-chlorophenyl)oxazol-2-yl)(pyridin-3-yl)methoxy)-2,6-difluorobenzamide;

3-(3-(2-acetylhydrazinyl)-1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-oxopropoxy)-2,6-difluorobenzamide;

3-(4-amino-1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-4-oxobutoxy)-2,6-difluorobenzamide;

3-((1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)allyl)oxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-methoxyethoxy)-2,6-difluorobenzamide;

3-((1-(5-bromo-4-(4-chlorophenyl)oxazol-2-yl)but-3-en-1-yl)oxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)-2,6-difluorobenzamide;

3-((1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)but-3-en-1-yl)oxy)-2,6-difluorobenzamide;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl dimethylcarbamate;

2-(5-bromo-4-(3-methoxyphenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3,4-dihydroxybutoxy)-2,6-difluorobenzamide;

(R,S)-3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3,4-dihydroxybutoxy)-2,6-difluorobenzamide;

(S,R)-3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3,4-dihydroxybutoxy)-2,6-difluorobenzamide;

(S,S)-3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3,4-dihydroxybutoxy)-2,6-difluorobenzamide;

(R,R)-3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3,4-dihydroxybutoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-hydroxyphenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2-(5-bromo-4-(4-methoxyphenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

3-(1-(5-bromo-4-(4-methoxyphenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl methylcarbamate;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(1H-imidazol-1-yl)ethoxy)-2,6-difluorobenzamide;

2-(5-bromo-4-(4-(trifluoromethoxy)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

3-(1-(5-bromo-4-(4-(trifluoromethoxy)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(3-methoxyphenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(3-hydroxyphenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

diethyl 2-(2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl)malonate;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(5-methyl-1,3,4-oxadiazol-2-yl)ethoxy)-2,6-difluorobenzamide;

2-(5-bromo-4-(1-(3-carbamoyl-2,4-difluorophenoxy)propyl)oxazol-2-yl)ethyl acetate;

3-((1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)pent-4-en-1-yl)oxy)-2,6-difluorobenzamide;

ethyl 2-(3-carbamoyl-2,4-difluorophenoxy)-2-(2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)acetate;

2,6-difluoro-3-(2-hydroxy-1-(2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)ethoxy)benzamide;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)acetic acid;

3-((1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-4,5-dihydroxypentyl)oxy)-2,6-difluorobenzamide;

ethyl 2-(3-carbamoyl-2,4-difluorophenoxy)-2-(2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)acetate;

2-(5-bromo-2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

3-(1-(5-bromo-2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2-(3-carbamoyl-2,4-difluorophenoxy)-2-(2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)acetic acid;

2-(2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl)propane-1,3-diyl diacetate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (2-(dimethylamino)ethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl piperazine-1-carboxylate;

2,6-difluoro-3-(2-hydroxy-1-(2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)ethoxy)benzamide;

2-(5-bromo-2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

3-(1-(5-bromo-2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-4-hydroxy-3-(hydroxymethyl)butoxy)-2,6-difluorobenzamide;

ethyl 2-(((2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)carbonyl)amino)acetate;

methyl 3-(((2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)carbonyl)amino)propanoate;

2-(((2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)carbonyl)amino)acetic acid;

3-(((2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)carbonyl)amino)propanoic acid;

2-(5-bromo-4-(4-(methylsulfonyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl acetate;

3-(1-(5-bromo-4-(4-(methylsulfonyl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(4-bromo-5-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(2-hydroxyethoxy)ethoxy)-2,6-difluorobenzamide;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl tert-butyl ethane-1,2-diyldicarbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (2-aminoethyl)carbamate;

tert-butyl (2-(((2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)carbonyl)amino)ethyl)(methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (2-(methylamino)ethyl)carbamate;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(2-methoxyethoxy)ethoxy)-2,6-difluorobenzamide;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2-fluorophenoxy)ethyl acetate;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2-fluorobenzamide;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl morpholine-4-carboxylate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (2-(pyrrolidin-1-yl)ethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (2-(1H-imidazol-4-yl)ethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (2-hydroxyethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (2-methoxyethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (pyridin-2-ylmethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (pyridin-3-ylmethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (pyridin-4-ylmethyl)carbamate;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(2-morpholinoethoxy)ethoxy)-2,6-difluorobenzamide;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl 3-(methylsulfonyl)-2-oxoimidazolidine-1-carboxylate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl pyridin-3-ylcarbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (2-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((5-methyl-1,3,4-oxadiazol-2-yl)methyl)carbamate;

2-((((2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)carbonyl)amino)methyl)pyridine 1-oxide;

3-((((2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)carbonyl)amino)methyl)pyridine 1-oxide;

4-((((2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)carbonyl)amino)methyl)pyridine 1-oxide;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl pyridin-4-ylcarbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl 1H-tetrazol-5-ylcarbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl 4-methylpiperazine-1-carboxylate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((3-methyl-1,2,4-oxadiazol-5-yl)methyl)carbamate;

ethyl 2-(3-carbamoyl-2,4-difluorophenoxy)-2-(4-(tetrahydro-2H-pyran-4-yl)oxazol-2-yl)acetate;

(R)-4-(2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)-4-oxobutanoic acid;

2,6-difluoro-3-(2-hydroxy-1-(4-(tetrahydro-2H-pyran-4-yl)oxazol-2-yl)ethoxy)benzamide;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl methyl(pyridin-3-ylmethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl methyl(pyridin-4-ylmethyl)carbamate;

3-(1-(5-bromo-4-(tetrahydro-2H-pyran-4-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2,6-difluoro-3-((3-methyl-1,2,4-oxadiazol-5-yl)(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)methoxy)benzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2,3-dihydroxypropoxy)-2,6-difluorobenzamide;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (2-(2-methyl-1H-imidazol-1-yl)ethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl methyl(pyridin-2-ylmethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl methyl(pyrazin-2-ylmethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1-methyl-1H-pyrazol-3-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1-methyl-1H-pyrazol-5-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1-methyl-1H-imidazol-5-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((2-methoxypyridin-3-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl methyl(pyrimidin-4-ylmethyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1-methyl-1H-pyrazol-4-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((6-methylpyridin-2-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((2-methylpyridin-4-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1-methyl-1H-imidazol-2-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1-methyl-1H-pyrrol-2-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1-methyl-1H-imidazol-4-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1,3-dimethyl-1H-pyrazol-4-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1,5-dimethyl-1H-pyrazol-4-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((4-(2-methoxyethyl)-4H-1,2,4-triazol-3-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1-(2-methoxyethyl)-1H-imidazol-5-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((6-methoxypyridin-3-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((2-methoxypyridin-4-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1-methyl-1H-benzo[d]imidazol-2-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1,5-dimethyl-1H-pyrrol-2-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1,3-dimethyl-1H-pyrazol-5-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((1,5-dimethyl-1H-pyrazol-3-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((6-methylpyridin-3-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((2-methylpyridin-3-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl ((3-methylpyridin-4-yl)methyl)carbamate;

2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl (2-(2-oxopyridin-1(2H)-yl)ethyl)carbamate;

2,6-difluoro-3-((5-methyl-1,3,4-oxadiazol-2-yl)(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)methoxy)benzamide;

3-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-3-(3-carbamoyl-2,4-difluorophenoxy)propane-1,2-diyl diacetate;

2,6-difluoro-3-(2-hydroxy-1-(4-(6-(methylamino)pyridin-3-yl)oxazol-2-yl)ethoxy)benzamide;

3-(1-(5-bromo-4-propyloxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(4-(4-chloro-3-fluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2,6-difluoro-3-(1-(4-(2-fluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)benzamide;

3-(1-(5-bromo-4-(6-(methylamino)pyridin-3-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-chloro-3-fluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(4-(2,4-difluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(4-(4-chloro-2-methoxyphenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2,6-difluoro-3-(1-(4-(2-fluoro-4-methoxyphenyl)oxazol-2-yl)-2-hydroxyethoxy)benzamide;

3-(1-(5-bromo-4-(2-fluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(6-methoxypyridin-3-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(6-methylpyridin-3-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(5-bromo-4-chloro-2-methoxyphenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(2,4-difluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(S)-3-(1-(5-bromo-4-(2,4-difluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-3-(1-(5-bromo-4-(2,4-difluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(2-fluoro-4-methoxyphenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-chloro-2-fluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(5-cyanothiophen-2-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(5-bromothiophen-2-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(5-methoxypyridin-2-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-chloro-2-methylphenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4,5-dimethylthiazol-2-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(6-chloropyridin-3-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(2-methoxyethoxy)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(thiophen-2-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(5-methylthiophen-2-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(2,4-dimethylthiazol-5-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

methyl 4-(5-bromo-2-(1-(3-carbamoyl-2,4-difluorophenoxy)-2-hydroxyethyl)oxazol-4-yl)benzoate;

(R)-3-(1-(5-bromo-4-(thiazol-5-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(3,4-difluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-3-(1-(5-bromo-4-(6-cyanopyridin-3-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-3-(1-(5-bromo-4-(5-chlorothiophen-2-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

4-(5-bromo-2-(1-(3-carbamoyl-2,4-difluorophenoxy)-2-hydroxyethyl)oxazol-4-yl)benzoic acid;

4-(5-bromo-2-(1-(3-carbamoyl-2,4-difluorophenoxy)-2-hydroxyethyl)oxazol-4-yl)-N,N-dimethylbenzamide;

(R)-3-(1-(5-bromo-4-(2,3-dihydrobenzofuran-5-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-3-(1-(4-(benzofuran-5-yl)-5-bromooxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-3-(1-(5-bromo-4-(4-(morpholine-4-carbonyl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(3-bromo-4-(pyrrolidin-1-yl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-3-(1-(5-bromo-4-(2-methoxypyrimidin-5-yl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

3-(1-(2-(4-chlorophenyl)thiazol-4-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2,6-difluoro-3-(2-hydroxy-1-(4-(4-methoxyphenyl)thiazol-2-yl)ethoxy)benzamide;

2,6-difluoro-3-(2-hydroxy-1-(4-(5-methoxypyridin-2-yl)thiazol-2-yl)ethoxy)benzamide;

2,6-difluoro-3-(2-hydroxy-1-(4-(5-methoxypyrazin-2-yl)thiazol-2-yl)ethoxy)benzamide;

2,6-difluoro-3-(2-hydroxy-1-(4-(4-methoxyphenethyl)thiazol-2-yl)ethoxy)benzamide;

4-(2-(5-bromo-4-(2,4-difluorophenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)-4-oxobutanoic acid;

2,6-difluoro-3-(2-hydroxy-1-(4-(6-methylpyridin-3-yl)thiazol-2-yl)ethoxy)benzamide;

(R)-3-(1-(5-bromo-4-(2,4-difluorophenyl)oxazol-2-yl)-2-(2-hydroxyethoxy)ethoxy)-2,6-difluorobenzamide;

(R)-3-(1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2-(1-(3-carbamoyl-2,4-difluorophenoxy)-2-hydroxyethyl)-4-(4-chlorophenyl)thiazole 3-oxide;

3-(1-(5-cyclopropyl-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

2-fluoro-3-(2-hydroxy-1-(5-(methylthio)-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)-6-(methylthio)benzamide;

2,6-difluoro-3-(2-hydroxy-1-(5-(methylthio)-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)benzamide;

(R)-2,6-difluoro-3-(2-hydroxy-1-(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)benzamide;

(R)-3-(1-(5-bromo-4-(4-(difluoromethoxy)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-3-(1-(4-(4-(difluoromethoxy)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-3-(1-(5-bromo-4-ethyloxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

benzyl (2-(3-carbamoyl-2,4-difluorophenoxy)-2-(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethyl)carbamate;

3-(1-(5-butyl-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-2,6-difluoro-3-(1-(4-(4-fluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)benzamide;

(R)-3-(1-(5-bromo-4-(4-fluorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

benzyl (2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl)carbamate;

3-(2-amino-1-(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)-2,6-difluorobenzamide;

3-(2-acetamido-1-(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)-2,6-difluorobenzamide;

3-(2-acetamido-1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)-2,6-difluorobenzamide;

2,6-difluoro-3-(2-(methylsulfonamido)-1-(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)benzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(methylsulfonamido)ethoxy)-2,6-difluorobenzamide;

3-(2-(3-ethylureido)-1-(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)-2,6-difluorobenzamide;

methyl (2-(3-carbamoyl-2,4-difluorophenoxy)-2-(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethyl)carbamate;

methyl (2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl)carbamate;

3-(2-benzamido-1-(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)-2,6-difluorobenzamide;

3-(2-amino-1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-ethylureido)ethoxy)-2,6-difluorobenzamide;

3-(2-benzamido-1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethoxy)-2,6-difluorobenzamide;

N-(2-(3-carbamoyl-2,4-difluorophenoxy)-2-(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethyl)nicotinamide;

N-(2-(3-carbamoyl-2,4-difluorophenoxy)-2-(4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)ethyl)picolinamide;

N-(2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl)nicotinamide;

N-(2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl)picolinamide;

3-((1R,2R)-1-(5-bromo-4-(4-(difluoromethoxy)phenyl)oxazol-2-yl)-2-hydroxypropoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(2-(pyridin-3-yl)acetamido)ethoxy)-2,6-difluorobenzamide;

3-((1R,2S)-1-(5-bromo-4-(4-(difluoromethoxy)phenyl)oxazol-2-yl)-2-hydroxypropoxy)-2,6-difluorobenzamide;

3-(1-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(2-(2-methoxyethoxy)acetamido)ethoxy)-2,6-difluorobenzamide;

4-((2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl)amino)-4-oxobutanoic acid;

(R)-3-(1-(5-ethyl-4-(4-methoxyphenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-2,6-difluoro-3-(2-hydroxy-1-(5-(methoxymethyl)-4-(4-methoxyphenyl)oxazol-2-yl)ethoxy)benzamide;

2,6-difluoro-3-(2-hydroxy-1-(2-(4-methoxyphenyl)-5-vinyloxazol-4-yl)ethoxy)benzamide;

3-(1-(5-ethyl-2-(4-methoxyphenyl)oxazol-4-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide;

(R)-2,6-difluoro-3-(2-hydroxy-1-(3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl)ethoxy)benzamide; and

4-((2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethyl)carbamoyl)benzoic acid;

or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide, or prodrug thereof.

11. A method of treating a bacterial infection in a subject comprising administering an effective amount of a compound of Formula (I):

or a pharmaceutically acceptable salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide or prodrug thereof wherein:

W is a substituted C 6-10 -membered monocyclic or fused bicyclic aryl group or an optionally substituted 5-6-membered monocyclic heteroaryl or a 9-membered fused bicyclic heteroaryl group;

R 1 and R 2 are each independently selected from halo or H;

R 3 is selected from the group consisting of C t alkyl-R 4 , C 2-6 alkynyl, C 3-7 cycloalkyl, C 6 aryl, and 5-6 membered heterocyclyl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl may be optionally substituted with one or more R 4 or R 5 groups;

t is an integer selected from 0, 1, 2 and 3;

R 3′ is H;

R 4 is selected from the group consisting of C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl, C 1-6 alkylheterocyclyl, OR 6 , (C═O)R 6 , O(C═O)R 6 , C(═O)OR 6 , N(R 6 ) 2 , NR 6 C(═O)R 5 , C(═O)N(R 6 ) 2 , NR 6 C(═O)OR 5 , OC(═O)N(R 6 ) 2 , C(═O)NH—NHC(═O)R 5 , NHC(═O)NHC 1-6 alkyl, NHS(O) x R 5 , S(O) x R 5 , OS(O) x R 5 , OP(═O)(OR 6 ) 2 and P(═O)(OR 6 ) 2 wherein each C 2-6 alkenyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocycly may be further optionally substituted with one or more substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—HNC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR and P(═O)(OR 2 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl;

each R 5 is optionally substituted and is selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

each R 6 is independently selected from H, or optionally substituted C 1-6 alkyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

wherein each R 5 and R 6 independently may be further optionally substituted with one or more optional substituents independently selected from the group consisting of C 1-3 alkyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 2 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 2 ) 2 , C(═O)NH—NHC(═O)R 7 , S(O) x R 7 , OS(O) x R 2 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl; and

x is 0 or an integer from 1 to 2

to the subject.

12. A method according to claim 11 wherein the compound is administered in combination with another antibacterial agent.

13. A method according to claim 11 wherein the administration is intravenous administration, oral administration or a combination thereof.

14. A compound as defined in claim 1 or a pharmaceutically acceptable salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide-or prodrug thereof for treating a bacterial infection.

15. A composition comprising a compound as defined in claim 1 or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide or prodrug thereof.

16. The composition according to claim 15 which is a pharmaceutical composition adapted for intravenous administration or oral administration.

17. A method of disinfecting a living or non-living substrate which is the subject of a bacterial infestation, the method comprising applying a compound as defined in claim 1 or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, or N-oxide thereof to the substrate.

18. A process for preparing a compound as defined in claim 1 or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide, or prodrug thereof comprising the step of coupling a compound of Formula (III) with a compound of general formula LG-C(R 3 )(R 3 ′)—W:

wherein W, R 1 , R 2 , R 3 and are R 3 ′ are defined according to claim 1 and LG is a leaving group.

19. A process according to claim 18 wherein the compound of general formula LG-C(R 3 )(R 3 ′)—W is of Formula (IV)

wherein

X and Y are each independently a heteroatom selected from O, N and S or a carbon atom having an optional substituent;

Z is a heteroatom selected from O, N and S or is C—B;

A is selected from H, halo, optionally substituted C 6-10 aryl, optionally substituted 4-10 membered heterocyclyl or A together with B and the carbon atoms to which they are respectively attached join to form an optionally substituted 6-membered fused ring system;

B is selected from H, halo, optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl or B together with A and the carbon atoms to which they are respectively attached join to form an optionally substituted 6-membered fused ring system;

R 1 and R 2 are each independently selected from halo or H;

R 3 is selected from the group consisting of C t alkyl-R 4 , C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6 aryl, and 5-6 membered heterocyclyl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl may be optionally substituted with one or more R 4 or R 5 groups;

t is an integer selected from 0, 1, 2 or 3;

R 4 is selected from the group consisting of C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl, C 1-6 alkylheterocyclyl, OR 6 , (C═O)R 6 , O(C═O)R 6 , C(═O)OR 6 , N(R 6 ) 2 , NR 6 C(═O)R 5 , C(═O)N(R 6 ) 2 , NR 6 C(═O)OR 5 , OC(═O)N(R 6 ) 2 , C(═O)NH—NHC(═O)R 5 , NHC(═O)NHC 1-6 alkyl, NHS(O) x R 5 , S(O) x R 5 , OS(O) x R 5 , OP(═O)(OR 6 ) 2 , and P(═O)(OR 6 ) 2 wherein each C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocycly may be further optionally substituted with one or more substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—HNC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl;

each R 5 is selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

each R 6 is independently selected from H C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl; and

wherein each R 5 and R 6 independently may be optionally substituted with one or more substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—NHC(═O)R 5 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H and C 1-3 alkyl;

x is 0 or an integer from 1 to 2; and

LG is a leaving group.

20. A compound of Formula (I):

or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide, or prodrug thereof wherein

W is a 9-10 membered fused bicyclic heteroaryl group;

R 1 and R 2 are each independently halo;

R 3 is selected from the group consisting of C t alkyl-R 4 , C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6 aryl, and 5-6 membered heterocyclyl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl may be optionally substituted with one or more R 4 or R 5 groups;

t is an integer selected from 0, 1, 2 and 3;

R 3′ is H;

R 4 is selected from the group consisting of C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl, C 1-6 alkylheterocyclyl, OR 6 , (C═O)R 6 , O(C═O)R 6 , C(═O)OR 6 , N(R 6 ) 2 , NR 6 C(═O)R 5 , C(═O)N(R 6 ) 2 , NR 6 C(═O)OR 5 , OC(═O)N(R 6 ) 2 , C(═O)NH—NHC(═O)R 5 , NHC(═O)NHC 1-6 alkyl, NHS(O) x R 5 , S(O) x R 5 , OS(O) x R 5 , OP(═O)(OR 6 ) 2 and P(═O)(OR 6 ) 2 wherein each C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocycly may be further optionally substituted with one or more substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—HNC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl;

each R 5 is optionally substituted and is selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

each R 6 is independently selected from H or optionally substituted C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

wherein each R 5 and R 6 independently may be further optionally substituted with one or more optional substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—NHC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl; and

x is 0 or an integer from 1 to 2.

21. A compound selected from the group consisting of:

or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide, or prodrug thereof.

22. A composition comprising a compound as defined in claim 21 or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide or prodrug thereof.

23. A method of treating a bacterial infection in a subject comprising administering an effective amount of a compound as defined in claim 21 or a pharmaceutically acceptable salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide or prodrug thereof to the subject.

24. The compound of claim 1 wherein each R 5 is selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl; each R 6 is independently selected from H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl and each R 5 and R 6 independently may be optionally substituted with one or more substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—NHC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl.

25. A composition comprising a compound as defined in claim 3 or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide or prodrug thereof.

26. A method of treating a bacterial infection in a subject comprising administering an effective amount of a compound as defined in claim 3 or a pharmaceutically acceptable salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide or prodrug thereof to the subject.

27. A composition comprising a compound as defined in claim 10 or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide or prodrug thereof.

28. A method of treating a bacterial infection in a subject comprising administering an effective amount of a compound as defined in claim 10 or a pharmaceutically acceptable salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide or prodrug thereof to the subject.

29. A process for preparing a compound of Formula (I):

or a salt, racemate, diastereoisomer, enantiomer, hydrate, solvate, N-oxide, or prodrug thereof comprising the step of coupling a compound of Formula (III) with a compound of general formula LG-C(R 3 )(R 3 ′)—W:

wherein

W is a substituted C 6-10 -membered monocyclic or fused bicyclic aryl group or an optionally substituted 5-6-membered monocyclic heteroaryl or a 9-membered fused bicyclic heteroaryl group;

R 1 and R 2 are each independently selected from halo or H;

R 3 is selected from the group consisting of C t alkyl-R 4 , C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6 aryl, and 5-6 membered heterocyclyl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl may be optionally substituted with one or more R 4 or R 5 groups;

t is an integer selected from 0, 1, 2 and 3;

R 3′ is H;

R 4 is selected from the group consisting of C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl, C 1-6 alkylheterocyclyl, OR 6 , (C═O)R 6 , O(C═O)R 6 , C(═O)OR 6 , N(R 6 ) 2 , NR 6 C(═O)R 5 , C(═O)N(R 6 ) 2 , NR 6 C(═O)OR 5 , OC(═O)N(R 6 ) 2 , C(═O)NH—NHC(═O)R 5 , NHC(═O)NHC 1-6 alkyl, NHS(O) x R 5 , S(O) x R 5 , OS(O) x R 5 , OP(═O)(OR 6 ) 2 and P(═O)(OR 6 ) 2 wherein each C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocycly may be further optionally substituted with one or more substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—HNC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl;

each R 5 is optionally substituted and is selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

each R 6 is independently selected from H or optionally substituted C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

wherein each R 5 and R 6 independently may be further optionally substituted with one or more optional substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—NHC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl;

x is 0 or an integer from 1 to 2;

and LG is a leaving group.

30. A process according to claim 29 wherein the compound of general formula LG-C(R 3 )(R 3 ′)—W is of Formula (IV)

wherein

X and Y are each independently a heteroatom selected from O, N and S or a carbon atom having an optional substituent;

Z is a heteroatom selected from O, N and S or is C—B;

A is selected from H, halo, optionally substituted C 6-10 aryl, optionally substituted 4-10 membered heterocyclyl or A together with B and the carbon atoms to which they are respectively attached join to form an optionally substituted 6-membered fused ring system;

B is selected from H, halo, optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl or B together with A and the carbon atoms to which they are respectively attached join to form an optionally substituted 6-membered fused ring system;

R 1 and R 2 are each independently selected from halo or H;

R 3 is selected from the group consisting of C t alkyl-R 4 , C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 6 aryl, and 5-6 membered heterocyclyl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl may be optionally substituted with one or more R 4 or R 5 groups;

t is an integer selected from 0, 1, 2 or 3;

R 4 is selected from the group consisting of C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl, C 1-6 alkylheterocyclyl, OR 6 , (C═O)R 6 , O(C═O)R 6 , C(═O)OR 6 , N(R 6 ) 2 , NR 6 C(═O)R 5 , C(═O)N(R 6 ) 2 , NR 6 C (═O)OR 5 , OC(═O)N(R 6 ) 2 , C(═O)NH—NHC(═O)R 5 , NHC(═O)NHC 1-6 alkyl, NHS(O) x R 5 , S(O) x R 5 , OS(O) x R 5 , OP(═O)(OR 6 ) 2 , and P(═O)(OR 6 ) 2 wherein each C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocycly may be further optionally substituted with one or more substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—HNC(═O)R 7 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H, C 1-3 alkyl and C 2-3 alkenyl;

each R 5 is optionally substituted and is selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

each R 6 is independently selected from H or is optionally substituted C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, C 1-6 alkylaryl, 4-10 membered heterocyclyl and C 1-6 alkylheterocyclyl;

wherein each R 5 and R 6 independently may be further optionally substituted with one or more optional substituents independently selected from the group consisting of C 1-3 alkyl, C 2-3 alkenyl, C 1-3 alkoxyl, OR 7 , oxo, (C═O)R 7 , O(C═O)R 7 , C(═O)OR 7 , N(R 7 ) 2 , NR 7 C(═O)R 7 , C(═O)N(R 7 ) 2 , NR 7 C(═O)OR 7 , OC(═O)N(R 7 ) 2 , C(═O)NH—NHC(═O)R 5 , S(O) x R 7 , OS(O) x R 7 , OP(═O)(OR 7 ) 2 and P(═O)(OR 7 ) 2 wherein each R 7 is independently selected from H and C 1-3 alkyl;

x is 0 or an integer from 1 to 2; and

LG is a leaving group.

Assignments (6)
SECURITY INTEREST Recorded May 4, 2026
From: LEXICON PHARMACEUTICALS, INC.; LEXICON PHARMACEUTICALS (NEW JERSEY), INC.; LION ACQUISITION CORPORATION
To: HERCULES CAPITAL, INC., AS AGENT
Reel/Frame 075498/0899 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 21, 2014
From: BIOTA SCIENTIFIC MANAGEMENT PTY LTD.; BIOTA EUROPE LIMITED
To: TAXIS PHARMACEUTICALS, INC.
Reel/Frame 033584/0798 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 13, 2014
From: HAYDEN, DAVID JOHN; STOKES, NEIL ROBERT; COLLINS, IAN
To: BIOTA SCIENTIFIC MANAGEMENT PTY LTD
Reel/Frame 033094/0944 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 13, 2014
From: PALMER, JAMES T.; MITCHELL, JEFFREY PETER; OFFERMANN, DANIEL; PITT, GARY ROBERT WILLIAM
To: BIOTA SCIENTIFIC MANAGEMENT PTY LTD
Reel/Frame 033095/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 13, 2014
From: DAVIES, DAVID
To: BIOTA SCIENTIFIC MANAGEMENT PTY LTD
Reel/Frame 033095/0024 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 13, 2014
From: CZAPLEWSKI, LLOYD GEORGE
To: BIOTA SCIENTIFIC MANAGEMENT PTY LTD
Reel/Frame 033095/0038 →