IP Library › Granted Patent US 7,432,286

Granted Patent B1

US 7,432,286 · App. 10/088,074 · Granted Oct 7, 2008

Pharmaceutically active sulfonyl hydrazide derivatives

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Quick Facts

Patent No.: US 7,432,286
App. No.: 10/088,074
Granted: Oct 7, 2008
Kind: B1

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Abstract

The present invention is related to sulfonyl hydrazide derivatives for use as pharmaceutically active compounds, as well as to pharmaceutical formulations containing such sulfonyl hydrazide derivatives. Said sulfonyl hydrazide derivatives are efficient modulators of the JNK pathway, they are in particular efficient inhibitors of JNK 2 and 3. The present invention is furthermore related to novel sulfonyl hydrazide derivatives as well as to methods of their preparation. In Formula (I) Ar 1 and Ar 2 are independently from each other an unsubstituted or substituted aryl or beteroaryl group, X 1 and X 2 are independently from each other O or S; R 1 , R 2 , R 3 are independently from each other hydrogen or a C 1 -C 6 -alkyl substituent or R 1 forms a substituted or unsubstituted 5-6-membered saturated or unsaturated ring with Ar 1 ; or R 2 and R 3 form a substituted or unsubstituted 5-6-membered saturated or unsaturated ring; n is an integer from 0 to 5; G is selected from a group comprising or consisting of an unsubstituted or substituted 4-8 membered heterocycle containing at least one heteroatom, or G is a substituted or unstibstituted C 1 -C 6 -alkyl group.

Claims (270)

1. A sulfonyl hydrazide compound according to formula I

geometrical isomers thereof, optically active enantiomers thereof, diastereomers thereof, racemates thereof, and/or pharmaceutically acceptable salts thereof, wherein

Ar 1 and Ar 2 are independently from each other an unsubstituted or substituted aryl or heteroaryl group,

X 1 and X 2 are independently from each other O or S;

R 1 , R 2 , R 3 are independently from each other hydrogen or a C 1 -C 6 -alkyl substituent or R 1 forms a substituted or unsubstituted 5-6-membered saturated or unsaturated ring with Ar 1 ;

or R 2 and R 3 form a substituted or unsubstituted 5-6-membered saturated or unsaturated ring;

n is an integer from 1 to 5;

G is an unsubstituted or substituted 4-8 membered heterocycle containing at least one heteroatom;

with the proviso that if Ar 1 is 4-chlorophenyl, Ar 2 is thienyl, X 1 and X 2 are O, R 1 , R 2 and R 3 are H, n is 1, G is not one of the following:

2. A sulfonyl hydrazide compound according to formula I

geometrical isomers thereof, optically active enantiomers thereof, diastereomers thereof, racemates thereof, and/or pharmaceutically acceptable salts thereof, wherein

Ar 1 and Ar 2 are independently from each other an unsubstituted or substituted aryl or heteroaryl group,

X 1 and X 2 are independently from each other O or S;

R 1 , R 2 , R 3 are independently from each other hydrogen or a C 1 -C 6 -alkyl substituent or R 1 forms a substituted or unsubstituted 5-6-membered saturated or unsaturated ring with Ar 1 ;

or R 2 and R 3 form a substituted or unsubstituted 5-6-membered saturated or unsaturated ring;

n is an integer from 0 to 5;

G is an unsubstituted or substituted 4-8 membered heterocycle containing at least one heteroatom.

3. A sulfonyl hydrazide compound according to formula I

geometrical isomers thereof, optically active enantiomers thereof, diastereomers thereof, racemates thereof, and/or pharmaceutically acceptable salts thereof, wherein

Ar 1 and Ar 2 are independently from each other an unsubstituted or substituted aryl or heteroaryl group,

X 1 and X 2 are independently from each other O or S;

R 1 , R 2 , R 3 are independently from each other hydrogen or a C 1 -C 6 -alkyl substituent or R 1 forms a substituted or unsubstituted 5-6-membered saturated or unsaturated ring with Ar 1 ;

or R 2 and R 3 form a substituted or unsubstituted 5-6-membered saturated or unsaturated ring;

n is an integer from 0 to 5;

G is

wherein, both X 3 and X 3 are selected independently from each other from the group consisting of N, O, S or CHL′;

Y is O, S or NR 4 , whereby R 4 is H or an unsubstituted or substituted C 1 -C 6 -alkyl, an unsubstituted or substituted aryl or heteroaryl;

n′ is an integer from 0 to 5,

L and L′ are independently H, unsubstituted or substituted C 1 -C 6 -aliphatic alkyl, unsubstituted or substituted C 2 -C 6 -alkenyl, unsubstituted or substituted C 2 -C 6 -alkynyl, unsubstituted or substituted cyclic C 4 -C 8 -alkyl, optionally containing 1-3 heteroatoms and optionally fused with aryl or heteroaryl; or L is an unsubstituted or substituted aryl or heteroaryl, aryl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkyl, —C(O)—OR 5 , —C(O)—R 5 , —C(O)—NR 5′ R 5 , —NR 5′ R 5 , —NR 5′ C(O)R 5 , —NR 5′ C(O)NR 5′ R 5 , —(SO)R 5 , —(SO 2 )R 5 , —NSO 2 R 5 , or —SO 2 NR 5′ R 5 ;

whereby, R 5 and R 5′ are substituents being independently H, unsubstituted or substituted C 1 -C 6 -alkyl, unsubstituted or substituted C 2 -C 6 -alkenyl, unsubstituted or substituted C 2 -C 6 -alkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted aryl-C 1 -C 6 -alkyl, unsubstituted or substituted heteroaryl-C 1 -C 6 -alkyl;

said aryl or heteroaryl groups being optionally substituted by unsubstituted or substituted C 1 -C 6 -alkyl, unsubstituted or substituted C 1 -C 6 -alkoxy, unsubstituted or substituted C 2 -C 6 -alkenyl, unsubstituted or substituted C 2 -C 6 -alkynyl, amino, aminoacyl, aminocarbonyl, unsubstituted or substituted C 1 -C 6 -alkoxycarbonyl, aryl, carboxyl, cyano, halogen, hydroxy, nitro, sulfoxy, sulfonyl, C 1 -C 6 -thioalkoxy.

4. A sulfonyl hydrazide compound according to claim 1 , wherein Ar 1 and/or Ar 2 are independently selected from the group consisting of phenyl, thienyl, furyl, pyridyl, pyrazolyl, pyrimidinyl, imidazolyl, naphthyl, quinolyl, optionally substituted by unsubstituted or substituted C 1 -C 6 -alkyl, unsubstituted or substituted C 1 -C 6 -alkoxy, unsubstituted or substituted C 2 -C 6 -alkenyl, unsubstituted or substituted C 2 -C 6 -alkynyl, amino, acylamino, amino-carbonyl, unsubstituted or substituted C 1 -C 6 -alkoxycarbonyl, aryl, carboxyl, cyano, halogen, hydroxy, nitro, sulfoxy, sulfonyl, C 1 -C 6 -thioalkoxy.

5. A sulfonyl hydrazide compound according to formula I

geometrical isomers thereof, optically active enantiomers thereof, diastereomers thereof, racemates thereof, and/or pharmaceutically acceptable salts thereof, wherein

Ar 1 is a substituted or unsubstituted phenyl, X 1 and X 2 are O, while R 1 , R 2 , R 3 are all hydrogen, n is 1, Ar 2 is thienyl, G is selected from

whereby L is H, unsubstituted or substituted C 1 -C 6 -aliphatic alkyl, unsubstituted or substituted C 1 -C 6 -alkenyl, unsubstituted or substituted C 1 -C 6 -alkynyl, unsubstituted or substituted cyclic C 4 -C 8 -alkyl, optionally containing 1-3 heteroatoms and optionally fused with aryl or heteroaryl; or L is an unsubstituted or substituted aryl or heteroaryl, aryl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C-alkyl, —C(O)—OR 5 , —C(O)—R 5 , —C(O)—NR 5′ R 5 , —NR 5′ R 5 , —NR 5′ C(O)R 5 , —NR 5′ C(O)NR 5′ R 5 , —(SO)R 5 , —(SO 2 )R 5 , —NSO 2 R 5 , or —SO 2 NR 5′ R 5 .

6. A sulfonyl hydrazide compound according to formula I

geometrical isomers thereof, optically active enantiomers thereof, diastereomers thereof, racemates thereof, and/or pharmaceutically acceptable salts thereof, wherein

Ar 1 and Ar 2 are independently from each other an unsubstituted or substituted aryl or heteroaryl group,

X 1 and X 2 are independently from each other O or S;

R 1 , R 2 , R 3 are independently from each other hydrogen or a C 1 -C 6 -alkyl substituent or R 1 forms a substituted or unsubstituted 5-6-membered saturated or unsaturated ring with Ar 1 ;

or R 2 and R 3 form a substituted or unsubstituted 5-6-membered saturated or unsaturated ring;

n is an integer from 0 to 5, and

G is

whereby L is H, unsubstituted or substituted C 1 -C 6 -aliphatic alkyl, unsubstituted or substituted C 2 -C 6 -alkenyl, unsubstituted or substituted C 2 -C 6 -alkynyl, unsubstituted or substituted cyclic C 4 -C 8 -alkyl, optionally containing 1-3 heteroatoms and optionally fused with aryl or heteroaryl; or L is an unsubstituted or substituted aryl or heteroaryl, aryl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkyl, —C(O)—OR 5 , —C(O)—R 5 , —C(O)—NR 5′ R 5 , —NR 5′ R 5 , —NR 5′ C(O)R 5 , —NR 5′ C(O)NR 5′ R 5 , —(SO)R 5 , —(SO 2 )R 5 , —NSO 2 R 5 , or —SO 2 NR 5′ R 5 .

7. A sulfonyl hydrazide compound according to claim 6 , wherein L is a substituted or unsubstituted pyridyl group.

8. A sulfonyl hydrazide compound selected from the following group:

4-chloro-N-[(5-{[2-({2-[4-(1,3-dithiolan-2-yl)phenyl]-1,3-thiazol-4-yl}carbonyl)-hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

4-chloro-N-{[5-({2-[(2-phenyl-1,3-thiazol-4-yl)carbonyl]hydrazino}sulfonyl)thien-2-yl]methyl}benzamide

4-chloro-N-{[5-({2-[(2-{[(4-chlorophenyl)sulfonyl]methyl}-1,3-thiazol-4-yl)carbonyl]hydrazino}sulfonyl)thien-2-yl]methyl}benzamide

4-chloro-N-{[5-({2-[(2-methyl-1,3-thiazol-4-yl)carbonyl]hydrazino}sulfonyl)thien-2-yl]methyl}benzamide

4-chloro-N-[(5-{[2-({2-[4-(1H-pyrrol-1-yl)phenyl]-1,3-thiazol-4-yl}carbonyl)-hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

4-chloro-N-[(5-{[2-({2-[(4,5-dichloro-1H-imidazol-1-yl)methyl]-1,3-thiazol-4-yl}carbonyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

4-chloro-N-[(5-{[2-({2-[5-(trifluoromethyl)pyridin-2-yl]-1,3-thiazol-4-yl}carbonyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

4-chloro-N-[(5-{[2-({2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1,3-thiazol-4-yl}carbonyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

4-chloro-N-[(5-{[2-({2-[2-chloro-4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl}carbonyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

4-chloro-N-[(5-{[2-({2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl}-carbonyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

4-chloro-N-({5-[(2-{[2-(2,3-dichlorophenyl)-1,3-thiazol-4-yl]carbonyl}-hydrazino)sulfonyl]thien-2-yl}methyl)benzamide

4-chloro-N-{[5-({2-[(2-{[(2-furylmethyl)sulfonyl]methyl}-1,3-thiazol-4-yl)carbonyl]hydrazino}sulfonyl)thien-2-yl]methyl}benzamide

4-chloro-N-[(5-{[2-({2-[(2-chlorophenoxy)methyl]-1,3-thiazol-4-yl}carbonyl)-hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

4-chloro-N-({5-[(2-{[2-(2,6-dichlorobenzyl)-1,3-thiazol-4-yl]carbonyl}hydrazino)-sulfonyl]thien-2-yl}methyl)benzamide

N-[(5-{[2-({2-[4-(1,3-dithiolan-2-yl)phenyl]-1,3-thiazol-4-yl}carbonyl)hydrazino]-sulfonyl}thien-2-yl)methyl]-3-nitrobenzamide

N-[(5-{[2-({2-[4-(1,3-dithiolan-2-yl)phenyl]-1,3-thiazol-4-yl}carbonyl)hydrazino]-sulfonyl}thien-2-yl)methyl]-3-methoxybenzamide

N-[(5-{[2-({2-[4-(1,3-dithiolan-2-yl)phenyl]-1,3-thiazol-4-yl}carbonyl)hydrazino]-sulfonyl}thien-2-yl)methyl]-4-nitrobenzamide

N′-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]thiophene-2-sulfonohydrazide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-4-nitrobenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-3-hydroxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-hydroxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-furamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-thien-2-ylacetamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-1-naphthamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-naphthamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-4-methylbenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-4-ethylbenzamide

4-tert-butyl-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-fluorobenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-3-fluorobenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-4-fluorobenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2,6-difluorobenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-3,5-difluorobenzamide

2-chloro-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

3-chloro-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-4-iodobenzamide

2,6-dichloro-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

3,5-dichloro-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

2-bromo-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

3-bromo-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

4-bromo-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-iodobenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-3-nitrobenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-nitrobenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-4-(dimethylamino)benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-3-methoxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-methoxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-4-methoxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2,6-dimethoxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-3,5-dimethoxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-(trifluoromethyl)benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-3-(trifluoromethyl)benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-4-(trifluoromethyl)benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-3,5-bis(trifluoromethyl)benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]nicotinamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]isonicotinamide

4-amino-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-4-hydroxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-3,4-dihydroxybenzamide

3,4-diamino-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]pyridine-2-carboxamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-6-hydroxypyridine-2-carboxamide

6-amino-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]nicotinamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-sulfanylnicotinamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-6-sulfanylnicotinamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2,6-dihydroxyisonicotinamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-5-nitro-1H-pyrazole-3-carboxamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-hydroxy-6-methoxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-8-hydroxyquinoline-7-carboxamide

2-amino-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}thien-2-yl)methyl]nicotinamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-4-fluoro-3-nitrobenzamide

2-amino-N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2,3,4-trihydroxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2-oxo-1,2-dihydropyridine-3-carboxamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2,4-dihydroxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-5-hydroxypyridine-2-carboxamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}thien-2-yl)methyl]-1H-imidazole-4-carboxamide

4-chloro-N-(4-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}benzyl)benzamide

4-chloro-N-(2-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}phenyl)benzamide

4-chloro-N-(3-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}phenyl)benzamide

N-(4-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}benzyl)-3-nitrobenzamide

4-chloro-N-(3-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}-butanoyl)hydrazino]sulfonyl}benzyl)benzamide

N-(3-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}benzyl)benzamide

N-(3-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}benzyl)-2-hydroxybenzamide

N-(3-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)-hydrazino]sulfonyl}benzyl)-3-nitrobenzamide.

9. A sulfonamide compound according to claim 8 , which is selected from the group consisting of

4-chloro-N-[(5-{[2-({2-[4-(1,3-dithiolan-2-yl)phenyl]-1,3-thiazol-4-yl}carbonyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

4-chloro-N-[(5-{[2-({2-[(2-chlorophenoxy)methyl]-1,3-thiazol-4-yl}carbonyl)hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)hydrazino]sulfonyl}thien-2-yl)methyl]-2-hydroxybenzamide

N-[(5-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)hydrazino]sulfonyl}thien-2-yl)methyl]-2-oxo-1,2-dihydropyridine-3-carboxamide

4-chloro-N-(4-{[2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}butanoyl)hydrazino]sulfonyl}benzyl)benzamide.

10. A pharmaceutical composition containing at least one sulfonyl hydrazide compound according to claim 1 and a pharmaceutically acceptable carrier, diluent or excipient thereof.

11. A process for the preparation of the sulfonyl hydrazide compound according to claim 1 comprising

a) preparing a sulfonyl compound V

b) and reacting it with the hydrazide compound VIII

whereby the substituents Ar 1 , Ar 2 , R 1 , R 2 , R 3 , X 1 , X 2 and G are as defined in claim 1 .

12. A sulfonyl hydrazide compound according to claim 2 , wherein G is

wherein, both X 3 and X 3′ are selected independently from each other from the group consisting of N, O, S or CHL′;

Y is O, S or NR 4 , whereby R 4 is H or an unsubstituted or substituted C 1 -C 6 -alkyl, an unsubstituted or substituted aryl or heteroaryl;

n′ is an integer from 0 to 5;

L and L′ are independently selected from the group consisting of H, unsubstituted or substituted C 1 -C 6 -aliphatic alkyl, unsubstituted or substituted C 2 -C 6 -alkenyl, unsubstituted or substituted C 2 -C 6 -alkynyl, unsubstituted or substituted cyclic C 4 -C 8 -alkyl, optionally containing 1-3 heteroatoms and optionally fused with aryl or heteroaryl; or L is an unsubstituted or substituted aryl or heteroaryl, aryl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkyl, —C(O)—OR 5 , —C(O)—R 5 , —C(O)—NR 5′ R 5 , —NR 5′ R 5 , NR 5′ C(O)R 5 , —NR 5′ C(O)NR 5′ R 5 , —(SO)R 5 , —(SO 2 )R 5 , —NSO 2 R 5 , —SO 2 NR 5′ R 5 ;

whereby, R 5 and R 5′ are substituents being independently selected from the group consisting of H, unsubstituted or substituted C 1 -C 6 -alkyl, unsubstituted or substituted C 2 -C 6 -alkenyl, unsubstituted or substituted C 2 -C 6 -alkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted aryl-C 1 -C 6 -alkyl, unsubstituted or substituted heteroaryl-C 1 -C 6 -alkyl;

13. A sulfonyl hydrazide compound according to claim 2 , wherein Ar 1 and/or Ar 2 are independently selected from the group consisting of phenyl, thienyl, furyl, pyridyl, pyrazolyl, pyrimidinyl, imidazolyl, naphthyl, quinolyl, optionally substituted by unsubstituted or substituted C 1 -C 6 -alkyl, unsubstituted or substituted C 1 -C 6 -alkoxy, unsubstituted or substituted C 2 -C 6 -alkenyl, unsubstituted or substituted C 2 -C 6 -alkynyl, amino, acylamino, amino-carbonyl, unsubstituted or substituted C 1 -C 6 -alkoxycarbonyl, aryl, carboxyl, cyano, halogen, hydroxy, nitro, sulfoxy, sulfonyl, C 1 -C 6 -thioalkoxy.

14. A sulfonyl hydrazide compound according to claim 2 , wherein Ar 1 is a substituted or unsubstituted phenyl, X 1 and X 2 are O, while R 1 , R 2 , R 3 are all hydrogen, n is 1, Ar 2 is thienyl, G is selected from

whereby L is H, unsubstituted or substituted C 1 -C 6 -aliphatic alkyl, unsubstituted or substituted C 2 -C 6 -alkenyl, unsubstituted or substituted C 2 -C 6 -alkynyl, unsubstituted or substituted cyclic C 4 - 8 -alkyl, optionally containing 1-3 heteroatoms and optionally fused with aryl or heteroaryl; or L is an unsubstituted or substituted aryl or heteroaryl, aryl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkyl, —C(O)—OR 5 , —C(O)—R 5 , —C(O)—NR 5′R 5 , —NR 5′ R 5 , —NR 5′ C(O)R 5 , —NR 5′ C(O)NR 5′ R 5 , —(SO)R 5 , —(SO 2 )R 5 : —NSO 2 R 5 , or —SO 2 NR 5′ R 5 .

15. A sulfonyl hydrazide compound according to claim 2 , wherein G is

16. A sulfonyl hydrazide compound according to claim 15 , wherein L is a substituted or unsubstituted pyridyl group.

17. A sulfonyl hydrazide compound according to claim 2 selected from the following group:

4-chloro-N-[(5-{[2-({2-[4-(1,3-dithiolan-2-yl)phenyl]-1,3-thiazol-4-yl}carbonyl)-hydrazino]sulfonyl}thien-2-yl)methyl]benzamide

4-chloro-N-{[5-({2-[(2-phenyl-1,3-thiazol-4-yl)carbonyl]hydrazino}sulfonyl)thien-2-yl]methyl}benzamide

4-chloro-N-{[5-({2-[(2-{[(4-chlorophenyl)sulfonyl]methyl}-1,3-thiazol-4-yl)-carbonyl]hydrazino}sulfonyl)thien-2-yl]methyl}benzamide