Chemical compounds

1. A compound of the formula II, or a salt thereof,

in which

R is C 3-6 cycloalkyl or naphthyl; or

R is

in which R1 is hydrogen, halogen, —C 1-6 alkyl, —SC 1-6 alkyl, —OC 1-6 alkyl, —NO 2 , —S(═O)—C 1-6 alkyl, —OH, —CF 3 , —CN, —CO 2 H, —OCF 3 , or —CO 2 C 1-6 alkyl;

and R2 and R3 are independently hydrogen, halogen, —C 1-6 alkyl, —SC 1-6 alkyl, —CO 1-6 alkyl, —NO 2 , —S(═O)—C 1-6 alkyl, —OH, —CF 3 , —CN, —CO 2 H, —CO 2 C 1-6 alkyl, —CONH 2 , —NH 2 , —OCH 2 (C═O)OH, —OCH 2 CH 2 OCH 3 , —SO 2 NH 2 , —CH 2 SO 2 CH 3 , —NH(C═NH)CH 3 ; or R2 and R3 can independently be a radical of the formula

R is

in which q is one or two; R4 is hydrogen, halogen, or —SO 2 NH 2 ; or

R is (CH 2 )—NR k R l in which n is 2 or 3, and R k and R l are independently —C 1-6 alkyl; or —NR k R l together form

R is

Q is

in which R5 is hydrogen, phenyl optionally substituted with up to three C 1-6 alkyl or halogen, or C 1-6 alkyl; or

Q is

in which Y is CH; and A and B together are a part of

provided that ortho position to Y is N or O.

2. A compound of formula II as described in claim 1 in which

R is C 3-6 cycloalkyl or naphthyl; or

R is

in which R1 is hydrogen, halogen, —C 1-6 alkyl, —SC 1-6 alkyl, —OC 1-6 alkyl, —NO 2 , —S(═O)—C 1-6 alkyl, —OH, —CF 3 , —CN, —CO 2 H, —OCF 3 , or —CO 2 C 1-6 alkyl;

and R2 and R3 are independently hydrogen, halogen, —C 1-6 alkyl, —SC 1-6 alkyl, —OC 1-6 alkyl, —NO 2 , —S(═O)—C 1-6 alkyl, —OH, —CF 3 , —CN, —CO 2 H, —CO 2 C 1-6 alkyl, —CONH 2 , —NH 2 , —OCH 2 (C═O)OH, —OCH 2 CH 2 OCH 3 , —SO 2 NH 2 , —CH 2 SO 2 CH 3 , —NH(C═NH)CH 3 ; or R2 and R3 can independently be a radical of the formula

R is

in which q is one or two; R4 is hydrogen, halogen, or —SO 2 NH 2 ; or

R is (CH 2 )—NR k R l in which n is 2 or 3, and R k and R l are independently —C 1-6 alkyl; or NR k R l together form

R is

Q is

in which R5 is hydrogen, phenyl optionally substituted with up to three C 1-6 alkyl or halogen, or C 1-6 alkyl; or

Q is

in which Y is CH; and A and B together are a part of

provided that ortho position to Y is N or O, or a salt thereof.

3. A compound of formula II as described in claim 2 in which R is

in which R1 is halogen, —C 1-6 alkyl, —SC 1-6 alkyl, —OC 1-6 alkyl, —NO 2 , —S(═O)—C 1-6 alkyl, —OH, —CF 3 , —CN, —CO 2 H, or —CO 2 C 1-6 alkyl;

and R2 and R3 are independently hydrogen, halogen, —C 1-6 alkyl, —SC 1-6 alkyl, —OC 1-6 alkyl, —NO 2 , —S(═O)—C 1-6 alkyl, —OH, —CF 3 , —CN, —CO 2 H, —CO 2 C 1-6 alkyl, —NH 2 , or —NH(C═NH)CH 3 ;

and

Q is

Q is

in which Y is CH; and A and B together are a part of

provided that ortho position to Y is N or O, or a salt thereof.

4. A compound of formula II as described in claim 3 in which R is

in which R1 is halogen, —C 1-6 alkyl, —SC 1-6 alkyl, —OC 1-6 alkyl, —NO 2 , —S(═O)—C 1-6 alkyl, —OH, —CF 3 , —CN, —CO 2 H, or —CO 2 C 1-6 alkyl;

and R2 and R3 are independently hydrogen, halogen, —C 1-6 alkyl, —SC 1-6 alkyl, —OC 1-6 alkyl, —NO 2 , —S(═O)—C 1-6 alkyl, —OH, —CF 3 , —CN, —CO 2 H, —CO 2 C 1-6 alkyl, —NH 2 , or —NH(C═NH)CH 3 ;

and

Q is

Q is

in which Y is CH; and A and B together are a part of

provided that ortho position to Y is N or O, or a salt thereof.

5. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 or a salt thereof and one or more of pharmaceutically acceptable carriers, diluents and excipients.

6. A compound of claim 1 selected from the group consisting of:

2-(2-Chloro-5-fluoro-phenylimino)-5-(2,3-dihydro-benzo[1-6]dioxin-6-ylmethylene)-thiazolidin-4-one;

2-(2-Chloro-phenylimino)-5-(2-oxo-2H-chromen-6-ylmethylene)-thiazolidin-4-one;

2-(2-Chloro-phenylimino)-5-(2-oxo-2H-chromen-6-ylmethylene)-thiazolidin-4-one;

2-(2-Chloro-phenylimino)-5-(2-oxo-2H-chromen-6-ylmethylene)-thiazolidin-4-one;

5-(2,3-Dihydro-benzofuran-5-ylmethylene)-2-(2,4,6-trimethyl-phenylimino)-thiazolidin-4-one;

2-Cyclohexylimino-5-(2,3-dihydro-benzo[1-6]dioxin-6-ylmethylene)-thiazolidin-4-one;

2-Cyclohexylimino-5-(2,3-dihydro-benzofuran-5-ylmethylene)-thiazolidin-4-one;

5-(2,3-Dihydro-benzofuran-5-ylmethylene)-2-o-totylimino-thiazolidin-4-one;

5-(2,3-Dihydro-benzo[1-6]dioxin-6-ylmethylene)-2-o-tolylimino-thiazolidin-4-one;

5-[2-(2-Chloro-phenylimino)-4-oxo-thiazolidin-5-ylidenemethyl]-3H-benzooxazol-2-one;

2-(2-Trifluoromethyl-phenylimino)-5-(2,3-dihydro-benzofuran-5-ylmethylene)-thiazolidin-4-one;

2-(2-Bromo-phenylimino)-5-(2,3-dihydro-benzofuran-5-ylmethylene)-thiazolidin-4-one;

2-(2,6-Dichloro-phenylimino)-5-(2,3-dihydro-benzofuran-5-ylmethylene)-thiazolidin-4-one;

5-(2,3-Dihydro-benzofuran-5-ylmethylene)-2-(2-methylsulfanyl-phenylimino)-thiazolidin-4-one;

5-(2,3-Dihydro-benzofuran-5-ylmethylene)-2-(2-fluoro-phenylimino)-thiazolidin-4-one;

2-(2-Methylsulfanyl-phenylimino)-5-(quinolin-6-ylmethylene)-thiazolidin-4-one;

2-(2-Bromo-phenylimino)-5-(quinolin-6-ylmethylene)-thiazolidin-4-one;

2-(2,3-Dimethyl-phenylimino)-5-(quinolin-6-ylmethylene)-thiazolidin-4-one;

2-(Naphthalen-1-ylimino)-5-(quinolin-6-ylmethylene)-thiazolidin-4-one;

5-(Quinolin-6-ylmethylene)-2-(2-trifluoromethyl-phenylimino)-thiazolidin-4-one;

2-(2-Chloro-5-trifluoromethyl-phenylimino)-5-(quinolin-6-ylmethylene)-thiazolidin-4-one;

2-(2,6-Dichloro-phenylimino)-5-8quinolin-6-ylmethylene)-thiazolidin-4-one;

2-(2-Bromo-phenylimino)-5-(2,3-dihydro-benzo[1-6]dioxin-6-ylmethylene)-thiazolidin-4-one;

2-(2-Chloro-phenylimino)-5-(quinoxalin-6-ylmethylene)-thiazolidin-4-one;

2-(2,6-Dichloro-phenylimino)-5-(2,3-dihydro-benzo[1-6]dioxin-6-ylmethylene)-thiazolidin-4-one;

5-(2,3-Dihydro-benzo[1-6]dioxin-6-ylmethylene)-2-(2-nitro-phenylimino)-thiazolidin-4-one;

5-(2,3-Dihydro-benzofuran-5-ylmethylene)-2-(2-nitro-phenylimino)-thiazolidin-4-one;

2-(2-Chloro-4-fluoro-5-methyl-phenylimino)-5-(2,3-dihydro-benzofuran-5-ylmethylene)-thiazolidin-4-one;

3-Chloro-4-[5-(2,3-dihydro-benzofuran-5-ylmethylene)-4-oxo-thiazolidin-2-ylideneamino]-benzoic acid methyl ester;

2-(2-Chloro-5-fluoro-phenylimino)-5-(2,3-dihydro-benzofuran-5-ylmethylene)-thiazolidin-4-one;

2-(2-Chloro-4-trifluoromethyl-phenylimino)-5-(2,3-dihydro-benzofuran-5-ylmethylene)-thiazolidin-4-one;

2-(4-Bromo-2-chloro-phenylimino)-5-(2,3-dihydro-benzofuran-5-ylmethylene)-thiazolidin-4-one;

5-(2,3-Dihydro-benzofuran-5-ylmethylene)-2-(2-methanesulfinyl-phenylimino)-thiazolidin-4-one;

3-Chloro-4-[5-(2,3-dihydro-benzofuran-5-ylmethylene)-4-oxo-thiazolidin-2-ylideneamino]-benzoic acid;

5-[2-(2-Chloro-phenylimino)-4-oxo-thiazolidin-5-ylidenemethyl]-1H-pyridin-2-one;

2-(2-Methylsulfanyl-phenylimino)-5-(quinolin-6-ylmethylene)-thiazolidin-4-one;

2-(2-Chloro-4-fluoro-5-methyl-phenylimino)-5-(quinolin-6-ylmethylene)-thiazolidin-4-one;

2-(2-Chloro-5-fluoro-phenylimino)-5-(quinolin-6-ylmethylene)-thiazolidin-4-one;

2-(2-Chloro-5-fluoro-phenylimino)-5-(2,3-dihydro-benzo[1-6]dioxin-6-ylmethylene)-thiazolidin-4-one;

2-(2-Chloro-4-trifluoromethyl-phenylimino)-5-quinolin-6-ylmethylene-thiazolidin-4-one;

5-(Benzothiazol-6-ylmethylene)-2-(2-chloro-phenylimino)-thiazolidin-4-one;

5-(Benzo[1,2,5]thiadiazol-5-ylmethylene)-2-(2-bromo-phenylimino)-thiazolidin-4-one;

5-(Benzo[1,2,5]thiadiazol-5-ylmethylene)-2-(2-chloro-5-fluoro-phenylimino)-thiazolidin-4-one;

5-(Benzothiazol-6-ylmethylene)-2-(2,6-dichloro-phenylimino)-thiazolidin-4-one;

2-(2-Chloro-phenylimino)-5-(4-hydroxy-3-nitro-benzylidene)-thiazolidin-4-one;

2-(2-Chloro-phenylimino)-5-(4-hydroxy-3-methoxy-benzylidene)-thiazolidin-4-one;

2-(2-Chloro-phenylimino)-5-(4-hydroxy-benzylidene)-thiazolidin-4-one;

2-(2-Chloro-phenylimino)-5-(4-methoxy-benzylidene)-thiazolidin-4-one;

5-(3-Chloro-4-hydroxy-benzylidene)-2-(2-chloro-phenylimino)-thiazolidin-4-one;

2-(2-Chloro-phenylimino)-5-(3-fluoro-4-methoxy-benzylidene)-thiazolidin-4-one;

2-(2,6-Dichloro-phenylimino)-5-(3-fluoro-4-hydroxy-benzylidene)-thiazolidin-4-one;

2-(2-Chloro-phenylimino)-5-(3-fluoro-4-hydroxy-benzylidene)-thiazolidin-4-one;

2-(2-Chloro-5-fluoro-phenylimino)-5-(3-fluoro-4-hydroxy-benzylidene)-thiazolidin-4-one;

5-(3-Fluoro-4-hydroxy-benzylidene)-2-o-tolylimino-thiazolidin-4-one;

2-(2-Chloro-phenylimino)-5-quinolin-6-ylmethylene-thiazolidin-4-one;

5-Quinolin-6-ylmethylene-2-(2,4,6-trimethyl-phenylimino)-thiazolidin-4-one;

5-Quinolin-6-ylmethylene-2-o-tolylimino-thiazolidin-4-one;

2-(2-Methoxy-phenylimino)-5-quinolin-6-ylmethylene-thiazolidin-4-one;

5-(213-Dihydro-benzofuran-5-ylmethylene)-2-(2-dimethylamino-ethylamino)-thiazol-4-one;

Benzoic acid N′-(4-oxo-5-quinolin-6-ylmethylene-4,5-dihydro-thiazol-2-yl)-hydrazide;

2-(2-Dimethylamino-ethylimino)-5-quinolin-6-ylmethylene-thiazolidin-4-one;

5-(2,3-Dihydro-benzofuran-5-ylmethylene)-2-(piperidin-1-ylamino)-thiazol-4-one;

2-Benzylamino-5-(2,3-dihydro-benzofuran-5-ylmethylene)-thiazol-4-one;

2-(4-tert-Butyl-thiazol-2-ylamino)-5-(2,3-dihydro-benzofuran-5-ylmethylene)-thiazol-4-one;

4-{[5-(2,3-Dihydro-benzofuran-5-ylmethylene)-4-oxo-4,5-dihydro-thiazol-2-ylamino]-methyl}-benzenesulfonamide;

5-(2,3-Dihydro-benzofuran-5-ylmethylene)-2-(3-dimethylamino-propylamino)-thiazol-4-one;

5-(23-Dihydro-benzofuran-5-ylmethylene)-2-(3-imidazol-1-yl-propylamino)-thiazol-4-one;

Phenyl-carbamic acid N′-[5-(2,3-dihydro-benzofuran-5-ylmethylene)-4-oxo-4,5-dihydro-thiazol-2-yl]-hydrazide;

Benzoic acid N′-[5-(2,3-dihydro-benzofuran-5-ylmethylene)-4-oxo-4,5-dihydro-thiazol-2-yl]-hydrazide;

5-Benzo[1,2,5]thiadiazol-5-ylmethylene-2-(2,3,4-trifluoro-phenylamino)-thiazol-4-one;

5-Benzo[1,2,5]oxadiazol-5-ylmethylene-2-(2-nitro-phenylamino)-thiazol-4-one;

2-(2,6-Dichloro-phenylamino)-5-(4-[1,2,4]triazol-1-yl-benzylidene)-thiazol-4-one;

2-(2,6-Dichloro-phenylamino)-5-(1H-pyrrolo[2,3-b]pyridin-2-ylmethylene)-thiazol-4-one;

5-Benzo[1,2,5]thiadiazol-5-ylmethylene-2-(2,6-dichloro-phenylamino)-thiazol-4-one;

5-[2-(2-Methoxy-6-methyl-phenylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-1H-pyridin-2-one;

5-Benzo[1,2,5]thiadiazol-5-ylmethylene-2-(2-nitro-phenylamino)-thiazol-4-one;

2-(2-Bromo-6-fluoro-phenylamino)-5-quinolin-6-ylmethylene-thiazol-4-one;

2-(2-Methoxy-6-methyl-phenylamino)-5-quinolin-6-ylmethylene-thiazol-4-one;

5-Quinolin-6-ylmethylene-2-(2,3,4-trifluoro-phenylamino)-thiazol-4-one;

2-(2,6-Dichloro-phenylamino)-5-(2-oxo-2H-chromen-6-ylmethylene)-thiazol-4-one;

2-(2-Bromo-phenylamino)-5-(5-pyridin-2-yl-thiophen-2-ylmethylene)-thiazol-4-one;

2-(2-Bromo-phenylamino)-5-(1-oxy-pyridin-4-ylmethylene)-thiazol-4-one;

2-(2-Bromo-phenylamino)-5-(3-p-tolyl-benzo[c]isoxazol-5-ylmethylene)-thiazol-4-one;

2-(2-Bromo-phenylamino)-5-(3,4-dihydro-2H-benzo[b][1-6]dioxepin-7-ylmethylene)-thiazol-4-one;

5-Benzo[1,2,5]oxadiazol-5-ylmethylene-2-(2-bromo-phenylamino)-thiazol-4-one;

2-(2,6-Dichloro-phenylamino)-5-(2-methoxy-pyridin-3-ylmethylene)-thiazol-4-one;

2-(2-Chloro-phenylamino)-5-(6-methoxy-pyridin-3-ylmethylene)-thiazol-4-one;

2-(2-Chloro-5-trifluoromethyl-phenylamino)-5-quinolin-6-ylmethylene-thiazol-4-one;

2-(2-Bromo-phenylamino)-5-(4-hydroxy-3-methoxy-benzylidene)-thiazol-4-one;

5-(2,3-Dihydro-benzofuran-5-ylmethylene)-2-(2-methoxy-phenylamino)-thiazol-4-one;

2-(2-Nitro-phenylamino)-5-quinolin-6-ylmethylene-thiazol-4-one

2-(2-Bromo-phenylamino)-5-(3,4-diamino-benzylidene)-thiazol-4-one;

5-[2-(2-Chloro-phenylimino)-4-oxo-thiazolidin-5-ylidenemethyl]-1-methyl-1H-pyridin-2-one;

2-(2-Chloro-5-nitro-phenylamino)-5-quinolin-6-ylmethylene-thiazol-4-one;

2-(5-Amino-2-chloro-phenylamino)-5-quinolin-6-ylmethylene-thiazol-4-one;

N-[4-Chloro-3-(4-oxo-5-quinolin-6-ylmethylene-4,5-dihydro-thiazol-2-ylamino)-phenyl]-acetamidine hydrochloride;

4-{[4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}benzamide;

3-{[4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}benzenesulfonamide;

4-{[4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}-N-2-pyridinylbenzenesulfonamide;

2-({4-[(4-methyl-1-piperazinyl)methyl]phenyl}amino)-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one;

2-({4-[(methylsulfonyl)methyl]phenyl}amino)-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one;

2-({3-[(methylsulfonyl)methyl]phenyl}amino)-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one;

2-{[4-(4-methyl-1-piperazinyl)phenyl]amino}5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one;

2-{[2-(3-chlorophenyl)ethyl]amino}-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one;

4-(2-{[4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}ethyl)benzenesulfonamide;

3-{[4-oxo-5-(6-quinolinylmethylidene)-4,5-dihydro-1,3-thiazol-2-yl]amino}benzamide;

2-[(2,6-Difluoro-phenylamino)-methylene]-5-quinolin-6-ylmethylene-thiazolidin-4-one;

2-[(2,6-Difluoro-phenylamino)-methylene]-5-quinolin-6-ylmethylene-thiazolidin-4-one;

[2,4-Dichloro-5-(4-oxo-5-quinolin-6-ylmethylene-thiazolidin-2-ylideneamino)-phenoxy]-acetic acid;

2-[2,4-Dichloro-5-(2-methoxy-ethoxy)-phenylimino]-5-quinolin-6-ylmethylene-thiazolidin-4-one;

4-Chloro-3-(4-oxo-5-quinolin-6-ylmethylene-thiazolidin-2-ylideneamino)-benzoic acid; and

[2,4-Dichloro-5-(4-oxo-5-quinolin-6-ylmethylene-thiazolidin-2-ylideneamino)-phenoxy]-acetic acid,

or a salt thereof.