Heterocyclic urea compounds
The present invention provides a compound of the following formula, racemates, enantiomers and salts thereof. Also provided is the use of these compounds as antibacterials, compositions comprising them and processes for their manufacture.
1. A compound of Formula (I), a racemate, an enantiomer or a salt thereof:
wherein
X is selected from C(═X 1 ), S(═O) and SO 2 ;
X 1 is selected from O, S and NR 4 ;
R 1 is optionally substituted and selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl, CR 5 (R 6 ) 2 , NR 4 SO 2 R 5 , OR 6 , SR 6 , NH 2 , NR 5 R 6 and NR a R b where R a and R b join with the N to which they are attached to form an optionally substituted 5-10 membered heterocyclic ring;
R 2 is optionally substituted and selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;
R 3 is an optionally substituted C 1-6 alkyl;
R 4 is H or an optionally substituted C 1-6 alkyl;
R 5 is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;
Each R 6 is H or is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;
t is an integer selected from 0, 1, 2 and 3 wherein each (CH 2 ) t when present may be independently optionally substituted;
Z 1 , Z 2 and Z 3 are each independently selected from CR 7 and N where R 7 is selected from H, halo or an optional substituent and further where at least one of Z 1 , Z 2 or Z 3 is N; and
each cycloalkyl, cycloalkenyl, aryl, heterocyclyl and heteroaryl ring may be a monocyclic or fused bicyclic ring system.
2. A compound according to claim 1 wherein X is C(═X 1 ), X 1 is selected from O, S and NR 4 and R 1 is selected from NH 2 , NR 5 R 6 and NR a R b .
3. A compound of claim 1 of Formula (Ia), a racemate, an enantiomer or a salt thereof:
wherein
X 1 is selected from O, S or NR 4 ;
R 1 is selected from NH 2 , NR 5 R 6 and NR a R b where R a and R b join with the N to which they are attached to form an optionally substituted 5-10 membered heterocyclic ring;
R 2 is optionally substituted and selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;
R 3 is an optionally substituted C 1-6 alkyl;
R 4 is H or an optionally substituted C 1-6 alkyl;
R 5 is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;
R 6 is H or is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;
t is an integer selected from 0, 1, 2 and 3 and wherein each (CH 2 ) t when present may be independently optionally substituted; and
Z 1 , Z 2 and Z 3 are each independently selected from CR 7 and N where each R 7 is independently selected from H, halo or an optional substituent and further where at least one of Z 1 , Z 2 or Z 3 is N.
4. A compound of claim 1 wherein X 1 is O.
5. A compound of claim 1 wherein one of Z 1 , Z 2 or Z 3 is N and the two remaining are each CR 7 where each R 7 is independently selected from selected from H, halo or an optional substituent.
6. A compound of claim 1 wherein two of Z 1 , Z 2 or Z 3 are N and the one remaining is CR 7 where R 7 is independently selected from selected from H, halo or an optional substituent.
7. A compound of claim 1 wherein R 1 is NR a R b and R a and R b join with the N to which they are attached to form an optionally substituted 5- or 6-membered heterocyclic ring.
8. A compound accordingly to claim 1 wherein R 1 is NR 5 R 6 .
9. A compound of claim 1 of Formula (Ib), a racemate, an enantiomer or a salt thereof:
wherein
R 2 is optionally substituted and selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;
R 5 is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl;
R 6 is H or is optionally substituted and selected from C 1-6 alkyl, C 1-6 alkoxyl, C 2-6 alkenyl, C 2-6 alkynyl, (CH 2 ) t C 3-10 cycloalkyl, (CH 2 ) t C 3-10 cycloalkenyl, (CH 2 ) t C 6-10 aryl, (CH 2 ) t 3-10-membered heterocyclyl and (CH 2 ) t 5-10-membered heteroaryl; and
t is an integer selected from 0, 1, 2 and 3 wherein each (CH 2 ) t when present may be independently optionally substituted.
10. A compound of claim 1 wherein R 2 is selected from an optionally substituted cyclohexyl, an optionally substituted (CH 2 ) t phenyl, an optionally substituted 5-6-membered heterocyclyl and an optionally substituted (CH 2 ) t 5-6-membered heteroaryl ring where t is 0 or 1.
11. A compound of claim 1 wherein R 5 is selected from an optionally substituted C 1-3 alkyl, an optionally substituted C 3-6 cycloalkyl, an optionally substituted (CH 2 ) t phenyl, an optionally substituted 5-6-membered heterocyclyl, an optionally substituted (CH 2 ) t 5-6-membered heteroaryl ring and an optionally substituted 9-10-membered heteroaryl ring where t is an integer 0, 1 or 2.
12. A compound of claim 1 wherein R 2 and R 5 are each independently selected from an optionally substituted (CH 2 ) t phenyl, an optionally substituted (CH 2 ) t 5-6-membered heterocyclyl, an optionally substituted (CH 2 ) t 5-6-membered heteroaryl ring and an optionally substituted (CH 2 ) t 9-10-membered heteroaryl ring where t is an integer 0, 1 or 2 and R 6 is H.
13. A compound of claim 1 selected from the group consisting of:
6-(3-ethylureido)-N-m-tolyl-4-(m-tolylamino)nicotinamide;
6-(3-ethylureido)-N-(thiazol-2-yl)-4-(m-tolylamino)nicotinamide;
4-(cyclohexylamino)-6-(3-ethylureido)-N-m-tolylnicotinamide;
N-(3-chlorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
2-(3-ethylureido)-N-phenyl-4-(phenylamino)pyrimidine-5-carboxamide;
2-(3-ethylureido)-4-(phenylamino)-N-(pyridin-3-yl)pyrimidine-5-carboxamide;
N-(3-chlorophenyl)-2-(3-ethylureido)-4-(phenylamino)pyrimidine-5-carboxamide;
N-ethyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
N-(2-chlorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(1-methyl-1H-pyrazol-5-yl)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(2-(trifluoromethyl)phenyl) nicotinamide;
ethyl (2E)-3-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}prop-2-enoate;
6-(3-ethylureido)-N-phenyl-4-(pyridin-3-ylamino)nicotinamide;
6-(3-ethylureido)-4-(4-methoxyphenylamino)-N-(pyridin-3-yl)nicotinamide;
ethyl 4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)benzoate;
4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)benzoic acid;
6-(3-ethylureido)-N-phenyl-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-m-tolylnicotinamide;
6-(3-ethylureido)-N-(pyridin-3-yl)-4-(pyridin-3-ylamino)nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-3-yl)nicotinamide;
methyl 4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)picolinate;
ethyl 6-(3-ethylureido)-4-(pyridin-3-ylmethylamino)nicotinate;
6-(3-ethylureido)-N-(6-morpholinopyridin-3-yl)-4-(phenylamino)nicotinamide;
N-(6-acetamidopyridin-3-yl)-6-(3-ethylureido)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-N-phenyl-4-(pyridin-3-ylmethylamino)nicotinamide;
6-(3-ethylureido)-N-(pyridin-3-yl)-4-(pyridin-3-ylmethylamino) nicotinamide;
N-(6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-3-ylmethyl)nicotinamide;
2-(3-ethylureido)-N-phenyl-4-(pyridin-3-ylamino)pyrimidine-5-carboxamide;
6-(3-ethylureido)-N,N-dimethyl-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(2-methoxyphenyl)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(3-methoxyphenyl)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(4-methoxyphenyl)-4-(phenylamino)nicotinamide;
N-(4-chlorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
2-(3-ethylureido)-N-(pyridin-3-yl)-4-(pyridin-3-ylamino)pyrimidine-5-carboxamide;
6-(3-ethylureido)-N-isopropyl-4-(phenylamino)nicotinamide;
N-cyclopentyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
N-cyclopropyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-methyl-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(2-methoxyethyl)-4-(phenylamino)nicotinamide;
1-ethyl-3-(5-(morpholine-4-carbonyl)-4-(phenylamino)pyridin-2-yl)urea;
6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-4-yl)nicotinamide;
6-(3-ethylureido)-N-phenethyl-4-(phenylamino)nicotinamide;
N-benzyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
N-cyclohexyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-p-tolylnicotinamide
6-(3-ethylureido)-4-(phenylamino)-N-(4-(trifluoromethyl)phenyl) nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(3-(trifluoromethyl)phenyl) nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-2-yl)nicotinamide;
N-(3,5-dimethylisoxazol-4-yl)-6-(3-ethylureido)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-4-ylmethyl)nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(pyridin-2-ylmethyl)nicotinamide;
1-ethyl-3-(5-(4-methylpiperazine-1-carbonyl)-4-(phenylamino)pyridin-2-yl)urea;
1-(5-(4-acetylpiperazine-1-carbonyl)-4-(phenylamino)pyridin-2-yl)-3-ethylurea;
6-(3-ethylureido)-N-(4-fluorophenyl)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(3-fluorophenyl)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(2-fluorophenyl)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-o-tolylnicotinamide;
6-(3-ethylureido)-N-(1-methyl-1H-pyrazol-3-yl)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(pyrimidin-5-yl)nicotinamide;
6-(3-ethylureido)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(thiazol-2-yl)nicotinamide;
6-(3-ethylureido)-N-(6-methoxypyridin-3-yl)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(pyridazin-4-yl)nicotinamide;
6-(3-ethylureido)-N-(1-methyl-1H-pyrazol-4-yl)-4-(phenylamino) nicotinamide;
N-(3,5-difluorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
methyl 4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)benzoate;
4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)benzoic acid;
N-(3,4-difluorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
ethyl 2-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)acetate;
2-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)acetic acid;
N-(benzo[d]thiazol-2-yl)-6-(3-ethylureido)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-N-(4-methylthiazol-2-yl)-4-(phenylamino) nicotinamide;
N-(3,5-dimethylphenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(6-(trifluoromethyl)pyridin-3-yl) nicotinamide;
6-(3-ethylureido)-N-(imidazo[1,2-a]pyridin-6-yl)-4-(phenylamino) nicotinamide;
methyl 3-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)propanoate;
3-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)propanoic acid;
6-(3-ethylureido)-N-(5-methoxypyridin-3-yl)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-N-(2-methyl-4-oxo-4H-chromen-7-yl)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(6-methylpyridin-3-yl)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-N-(6-(4-fluorophenoxyl)pyridin-3-yl)-4-(phenylamino)nicotinamide
6-(3-ethylureido)-N-methoxy-N-methyl-4-(phenylamino)nicotinamide;
5-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)nicotinic acid;
6-(3-ethylureido)-N-(5-fluoropyridin-3-yl)-4-(phenylamino) nicotinamide;
methyl 4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)-1-methyl-1H-pyrrole-2-carboxylate;
3-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)benzoic acid;
6-(3-ethylureido)-N-(3-methyl-3H-imidazo[4,5-b]pyridin-6-yl)-4-(phenylamino)nicotinamide;
methyl 5-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)nicotinate;
6-(3-ethylureido)-N-(2-methylpyridin-4-yl)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-N-(5-methylpyridin-3-yl)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-4-(phenylamino)-N-(quinolin-3-yl)nicotinamide;
6-(3-ethylureido)-N-(3-fluoro-5-methylphenyl)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-N-(1-methyl-1H-indol-4-yl)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-N-(6-(isopropylamino)pyridin-3-yl)-4-(phenylamino) nicotinamide;
methyl 4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)benzoate;
methyl 3-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)benzoate;
N-(6-(dimethylamino)pyridin-3-yl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(6-(4-hydroxypiperidin-1-yl)pyridin-3-yl)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(6-methoxyquinolin-3-yl)-4-(phenylamino) nicotinamide;
methyl 2-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)benzo[d]thiazole-6-carboxylate;
4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)-1-methyl-1H-pyrrole-2-carboxylic acid;
N-(6-cyanopyridin-3-yl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
4-(2-chlorophenylamino)-6-(3-ethylureido)-N-(pyridin-3-yl) nicotinamide;
4-(4-chlorophenylamino)-6-(3-ethylureido)-N-(pyridin-3-yl) nicotinamide;
4-(3-chlorophenylamino)-6-(3-ethylureido)-N-(pyridin-3-yl) nicotinamide;
6-(3-ethylureido)-4-(1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)-N-(pyridin-3-yl)nicotinamide;
6-(3-ethylureido)-4-(2-methoxyphenylamino)-N-(pyridin-3-yl)nicotinamide;
ethyl 2-(4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)phenyl)acetate;
6-(3-ethylureido)-4-(3-methoxyphenylamino)-N-(pyridin-3-yl)nicotinamide;
1-(5-benzoyl-4-(phenylamino)pyridin-2-yl)-3-ethylurea;
6-(3-ethylureido)-4-(1-methyl-1H-pyrazol-4-ylamino)-N-(pyridin-3-yl)nicotinamide;
2-(4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)phenyl)acetic acid;
4-(3,5-dimethylisoxazol-4-ylamino)-6-(3-ethylureido)-N-(pyridin-3-yl)nicotinamide;
6-(3-ethylureido)-4-(1-methyl-1H-pyrazol-3-ylamino)-N-(pyridin-3-yl)nicotinamide;
6-(3-ethylureido)-N-(4-(3-hydroxypropyl)phenyl)-4-(phenylamino) nicotinamide;
N-(4-(3-amino-3-oxopropyl)phenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
N-(4-(3-(dimethylamino)-3-oxopropyl)phenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(4-(3-(methylamino)-3-oxopropyl)phenyl)-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-methyl-N-phenyl-4-(phenylamino)nicotinamide;
6-(3-ethylureido)-N-(4-(3-oxobutyl)phenyl)-4-(phenylamino) nicotinamide;
6-(3-ethylureido)-N-(4-(3-(methoxy(methyl)amino)-3-oxopropyl)phenyl)-4-(phenylamino)nicotinamide;
4-(4-(dimethylcarbamoyl)phenylamino)-6-(3-ethylureido)-N-(pyridin-3-yl)nicotinamide;
4-(4-carbamoylphenylamino)-6-(3-ethylureido)-N-(pyridin-3-yl)nicotinamide;
6-(3-ethylureido)-4-(4-(methylcarbamoyl)phenylamino)-N-(pyridin-3-yl)nicotinamide;
1-ethyl-3-(5-(2-phenylacetyl)-4-(phenylamino)pyridin-2-yl)urea;
6-(3-ethylureido)-4-(4-(hydroxymethyl)phenylamino)-N-(pyridin-3-yl)nicotinamide;
methyl 3-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)-2,2-dimethylpropanoate;
3-(4-(6-(3-ethylureido)-4-(phenylamino)nicotinamido)phenyl)-2,2-dimethylpropanoic acid;
ethyl 3-(4-(2-(3-ethylureido)-5-(pyridin-3-ylcarbamoyl)pyridin-4-ylamino)phenyl)propanoate;
N-(4-azidophenyl)-4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridine-3-carboxamide;
ethyl 1-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-1H-1,2,3-triazole-4-carboxylate;
6-[(ethylcarbamoyl)amino]-N-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-4-(phenylamino)pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-N-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-4-(phenylamino)pyridine-3-carboxamide;
ethyl 1-{5-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}-4-methylpiperidine-4-carboxylate;
(2E)-3-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}prop-2-enoic acid;
3-[4-({2-[(ethylcarbamoyl)amino]-5-(pyridin-3-ylcarbamoyl)pyridin-4-yl}amino)phenyl]propanoic acid;
6-[(ethylcarbamoyl)amino]-4-[(4-fluorophenyl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-4-[(4-methylphenyl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-Nyridin-3-yl)-4-{[3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-Nyridin-3-yl)-4-{[4-(trifluoromethyl)phenyl]amino}pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-4-[(3-fluorophenyl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-4-[(2-fluorophenyl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-4-[(6-methoxypyridin-3-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;
ethyl {4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenoxy}acetate;
methyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
methyl 3-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
3-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenoxy}acetic acid;
N-(6-chloropyridin-3-yl)-6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-N-[2-(3-hydroxyazetidin-1-yl)pyrimidin-5-yl]-4-(pyridin-3-ylamino)pyridine-3-carboxamide;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
methyl 1-[({5-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}amino)methyl]cyclobutanecarboxylate;
1-[({5-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}amino)methyl]cyclobutanecarboxylic acid;
methyl 1-[({5-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]pyridin-2-yl}amino)methyl]cyclobutanecarboxylate;
6-[(ethylcarbamoyl)amino]-4-[(5-methylpyridin-3-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;
1-[({5-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]pyridin-2-yl}amino)methyl]cyclobutanecarboxylic acid;
methyl 3-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoate;
3-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
4-(3,5-difluoroanilino)-6-(ethylcarbamoylamino)-N-[4-[2-(1H-tetrazol-5-yl)ethyl]phenyl]pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-4-[(2-methylpyridin-4-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-4-[(2-methoxypyridin-4-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;
ethyl 1-({5-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}amino)cyclobutanecarboxylate;
1-({5-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}amino)cyclobutanecarboxylic acid;
3-{5-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]pyridin-2-yl}propanoic acid;
6-[(ethylcarbamoyl)amino]-4-[(6-methylpyridin-3-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;
1-[({5-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]pyrimidin-2-yl}amino)methyl]cyclobutanecarboxylic acid;
(1R,2R)-2-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}cyclopropanecarboxylic acid;
methyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoate;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino)pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
4-{[6-(acetylamino)pyridin-3-yl]amino}-6-[(ethylcarbamoyl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-Nyridin-3-yl)-4-(pyrimidin-5-ylamino)pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-4-[(5-methoxypyridin-3-yl)amino]-Nyridin-3-yl)pyridine-3-carboxamide;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(4-fluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
3-[4-[[6-(ethylcarbamoylamino)-4-[4-(trifluoromethyl)anilino]pyridine-3-carbonyl]amino]phenyl]propanoic acid;
3-{4-[({4-[(3-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-methoxyphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
methyl 3-{5-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]pyridin-2-yl}propanoate;
ethyl (1R,2R)-2-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}cyclopropanecarboxylate;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(2-fluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
3-{4-[({4-[(2-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(4-fluoro-3-methoxyphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-[4-(3-hydroxy-3-methylbut-1-yn-1-yl)phenyl]pyridine-3-carboxamide;
3-{4-[({6-[(methylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(2-methoxypyridin-4-yl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
3-{4-[({4-[(4-cyanophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
3-[4-[[6-(ethylcarbamoylamino)-4-(3,4,5-trifluoroanilino)pyridine-3-carbonyl]amino]phenyl]propanoic acid;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluoro-4-methoxyphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-[4-(pyridin-2-ylethynyl)phenyl]pyridine-3-carboxamide;
(1R,2R)-2-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}cyclopropanecarboxylic acid;
(1R,2R)-2-{4-[({6-[(ethylcarbamoyl)amino]-4-(pyridin-3-ylamino) pyridin-3-yl}carbonyl)amino]phenyl}cyclopropanecarboxylic acid;
N-{4-[4-(aminomethyl)-1H-1,2,3-triazol-1-yl]phenyl}-4-[(4-chloro phenyl)amino]-6-[(ethylcarbamoyl)amino]pyridine-3-carboxamide;
tert-butyl 1-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}-L-prolinate;
3-(4-{[(6-[(ethylcarbamoyl)amino]-4-{[4-(methoxycarbonyl)phenyl]amino}pyridin-3-yl)carbonyl]amino}phenyl)-2,2-dimethylpropanoic acid;
methyl 1-{4-[({4-[(4-chlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-1H-pyrrole-2-carboxylate;
1-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}-1H-pyrrole-2-carboxylic acid;
3-{4-[({4-[(3-cyanophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
6-[(ethylcarbamoyl)amino]-4-[(4-fluorophenyl)amino]-N-[4-(pyrrolidin-1-ylmethyl)phenyl]pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-4-[(4-fluorophenyl)amino]-N-[4-(morpholin-4-ylmethyl)phenyl]pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-4-[(4-fluorophenyl)amino]-N-{4-[(4-methylpiperazin-1-yl)methyl]phenyl}pyridine-3-carboxamide;
4-[(4-cyanophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-[4-(pyrrolidin-1-ylmethyl)phenyl]pyridine-3-carboxamide;
4-[(4-cyanophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-[4-(morpholin-4-ylmethyl)phenyl]pyridine-3-carboxamide;
4-[(4-cyanophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-{4-[(4-methylpiperazin-1-yl)methyl]phenyl}pyridine-3-carboxamide;
diethyl {4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]benzyl}phosphonate;
{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]benzyl}phosphonic acid;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(4-methoxyphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
4-(3,5-difluoroanilino)-6-(ethylcarbamoylamino)-N-[4-(1H-tetrazol-5-ylmethyl)phenyl]pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-N-{4-[(methylsulfamoyl)methyl]phenyl}-4-(phenylamino)pyridine-3-carboxamide;
5-[(ethylcarbamoyl)amino]-3-(phenylamino)-N-(pyridin-3-yl)pyrazine-2-carboxamide;
6-[(ethylcarbamoyl)amino]-N-phenyl-4-(phenylamino)pyridazine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-N-[4-(methylcarbamoyl)phenyl]-4-(phenylamino)pyridine-3-carboxamide;
N-{4-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}-6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridine-3-carboxamide;
ethyl 3-{4-[({4-[(3,4-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
ethyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
ethyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluoro-4-methyl phenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
ethyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(4-fluoro-3-methylphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
ethyl 3-{4-[({4-[(4-chloro-2-fluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
3-{4-[({4-[(3,4-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(3-fluoro-4-methylphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(4-fluoro-3-methylphenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
3-{4-[({4-[(4-chloro-2-fluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
ethyl 3-{4-[({4-[(3,5-dichlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
ethyl 3-{4-[({4-[(3-chloro-4-fluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
ethyl 3-{4-[({4-[(2,4-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
3-{4-[({4-[(3,5-dichlorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
3-{4-[({4-[(3-chloro-4-fluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
3-{4-[({4-[(2,4-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
6-[(ethylcarbamoyl)amino]-4-(phenylamino)-N-(4-sulfamoylphenyl) pyridine-3-carboxamide;
6-[(ethylcarbamoyl)amino]-N-{4-[(methylsulfonyl)amino]phenyl}-4-(phenylamino)pyridine-3-carboxamide;
{3-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]-1H-pyrazol-1-yl}acetic acid;
ethyl 3-{4-[({4-[(3,5-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
3-{4-[({4-[(3,5-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(5-fluoropyridin-3-yl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoic acid;
3-(4-{[(6-[(ethylcarbamoyl)amino]-4-{[3-(pentafluorothio)phenyl]amino}pyridin-3-yl)carbonyl]amino}phenyl)propanoic acid;
2-{4-[({4-[(3,5-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}cyclopropanecarboxylic acid;
3-{4-[({4-[(3,5-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}-2,2-dimethylpropanoic acid;
3-(4-{[(6-[(ethylcarbamoyl)amino]-4-{[3-(trifluoromethyl)phenyl]amino}pyridin-3-yl)carbonyl]amino}phenyl)propanoic acid;
3-(4-{[(6-[(ethylcarbamoyl)amino]-4-{[3-(trifluoromethoxy)phenyl]amino}pyridin-3-yl)carbonyl]amino}phenyl)propanoic acid;
3-(4-{[(6-[(ethylcarbamoyl)amino]-4-{[4-(trifluoromethoxy)phenyl]amino}pyridin-3-yl)carbonyl]amino}phenyl)propanoic acid;
5-[(ethylcarbamoyl)amino]-3-(phenylamino)-N-(pyridin-3-yl)pyridine-2-carboxamide;
4-[(3,5-difluorophenyl)amino]-6-[(ethylcarbamoyl)amino]-N-[4-(morpholin-4-ylmethyl)phenyl]pyridine-3-carboxamide;
4-[(3,5-difluorophenyl)amino]-N-(4-{[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl}phenyl)-6-[(ethylcarbamoyl)amino]pyridine-3-carboxamide;
ethyl 3-{4-[({6-[(ethylcarbamoyl)amino]-4-[(2,3,4-trifluorophenyl)amino]pyridin-3-yl}carbonyl)amino]phenyl}propanoate;
ethyl 2-[[4-anilino-6-(ethylcarbamoylamino)pyridine-3-carbonyl]amino]thiazole-4-carboxylate;
4-(4-chloroanilino)-6-(ethylcarbamoylamino)-N-(2-methylpyrimidin-5-yl)pyridine-3-carboxamide;
ethyl 3-[[4-anilino-6-(ethylcarbamoylamino)pyridine-3-carbonyl]amino]benzoate;
1-[[4-[[4-(3,5-difluoroanilino)-6-(ethylcarbamoylamino)pyridine-3-carbonyl]amino]phenyl]methyl]pyrrolidine-2-carboxylic acid; and
1-[[4-[[4-(3,5-difluoroanilino)-6-(ethylcarbamoylamino)pyridine-3-carbonyl]amino]phenyl]methyl]piperidine-2-carboxylic acid;
a racemate, an enantiomer or a salt thereof.
14. An antibacterial agent comprising a compound according to claim 1 , a racemate, an enantiomer or a pharmaceutically acceptable salt thereof.
15. A pharmaceutical composition comprising a compound according claim 1 , a racemate, an enantiomer or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient or carrier.
16. A method for the treatment of a bacterial infection comprising administration of a compound according to claim 1 , a racemate, an enantiomer or a pharmaceutically acceptable salt thereof, to a subject suffering from said infection.
17. A method of treating bacterial contamination of a substrate comprising applying to the site of such contamination an amount of a compound according to claim 1 , a racemate, an enantiomer or pharmaceutically acceptable salt thereof sufficient to inhibit bacterial growth.
18. A process for the manufacture of a compound according to claim 1 via an intermediate of formula (II):
wherein R′ is a halo or NH 2 group and R 1 , R 2 , Z 1 , Z 2 , Z 3 and X are as defined in claim 1 ; or
via an intermediate of formula (III):
wherein R″ is H or C 1-6 alkyl and R 2 , R 3 , Z 1 , Z 2 and Z 3 are as defined in claim 1 ; or
via an intermediate of formula (IV):
wherein X, R 1 , R 3 , Z 1 , Z 2 and Z 3 are as defined in claim 1 .