IP Library Granted Patent US 8,017,628
Granted Patent B2
US 8,017,628 · App. 12/172,485 · Granted Sep 13, 2011

Pharmaceutically active sulfonyl hydrazide derivatives

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Quick Facts
Patent No.
US 8,017,628
App. No.
12/172,485
Granted
Sep 13, 2011
Kind
B2
Abstract

Sulfonyl hydrazide compounds according to formula I geometrical isomers thereof, optically active enantiomers thereof, diastereomers thereof, racemates thereof, and/or pharmaceutically acceptable salts thereof are useful in method for treating a neuronal disorder, an autoimmune disease, a cardiovascular disease, or cancer in a patient in need of such treatment.

Claims (128)

1. A method of treating a neuronal disorder, an autoimmune disease, or a cardiovascular disease in a patient in need of such treatment, the method comprising administering a therapeutically effective amount of 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 un-saturated ring;

n is an integer from 0 to 5;

G is an unsubstituted or substituted 4-8 membered heterocycle containing at least one heteroatom, or G is a substituted or unsubstituted C 1 -C 6 -alkyl group.

2. A method of treating a neuronal disorder, an autoimmune disease, or a cardiovascular disease in a patient in need of such treatment the method comprising administering a therapeutically effective amount of 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 un-saturated 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, like trihalomethyl, unsubstituted or substituted C 1 -C 6 -alkoxy, unsubstituted or substituted C 2 -C 6 -alkenyl, unsubstituted or substituted C 2 -C 6 -alky-nyl, amino, aminoacyl, aminocarbonyl, unsubstituted or substituted C 1 -C 6 -alkoxy-carbonyl, aryl, carboxyl, cyano, halogen, hydroxy, nitro, sulfoxy, sulfonyl, C 1 -C 6 -thioalkoxy.

3. The method of 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, in particular tri-halomethyl, 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.

4. The method of claim 1 , wherein Ar 1 is a substituted or unsubstituted phenyl, X′ and X 2 are 0, 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 -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 5t (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 .

5. The method of claim 1 , wherein 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 .

6. The method of claim 5 , wherein L is a substituted or unsubstituted pyridyl group.

7. The method of claim 1 , wherein the hydrazide compound is a 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]car-bonyl)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-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-yflmethyl]-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.

8. The method of claim 1 , wherein the sulfonamide compound 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.

9. The method of claim 1 , wherein a neuronal disease is treated.

10. The method of claim 9 , wherein the neuronal disease is epilepsy, Alzheimer's disease, Huntington's disease, Parkinson's disease, retinal disease, spinal cord injury or head trauma.

11. The method of claim 1 , wherein an autoimmune disease is treated.

12. The method of claim 11 , wherein the autoimmune disease is multiple sclerosis, inflammatory bowel disease, rheumatoid arthritis, asthma, septic shock, or transplant rejection.

13. The method of claim 1 , wherein a cardiovascular disease is treated.

14. The method of claim 13 , wherein the cardiovascular disease is stroke, arterosclerosis, myocardial infarction, or myocardial reperfusion injury.

Assignments (1)
CHANGE OF NAME Recorded Dec 3, 2009
From: LABORATOIRES SERONO SA
To: MERCK SERONO SA
Reel/Frame 023599/0944 →