IP Library › Granted Patent US 10,130,619

Granted Patent B2

US 10,130,619 · App. 15/536,800 · Granted Nov 20, 2018

Amido thiadiazole derivatives as NADPH oxidase inhibitors

Inventors: Peter Machin (London, GB); Andrew Sharpe (Saffron Walden, GB); Christopher James Lock (Saffron Walden, GB); Mark S. Chambers (Saffron Walden, GB); Alastair Hodges (Saffron Walden, GB); Vivienne Allen (Saffron Walden, GB); John M. Ellard (Saffron Walden, GB)

Assignee: GENKYOTEX SUISSE SA

A61K31/4439 A61K31/4545 A61K31/496 A61K31/506 A61K31/5355 C07D417/04 C07D417/14

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Quick Facts

Patent No.: US 10,130,619
App. No.: 15/536,800
Granted: Nov 20, 2018
Kind: B2

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Abstract

The present invention is related to amino thiazole derivatives of Formula (I), pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase).

Claims (182)

1. An amido thiadiazole compound according to Formula (I):

wherein X is selected from CR 1 and N; Y is selected from CH or N; A 1 is selected from —OCHR 5 —, —NR 4 —CHR 5 —, —CH 2 NR 4 — and —CH 2 —O—; R 1 is selected from H, halogen and optionally substituted C 1 -C 6 alkyl; R 2 is selected from H, halogen, optionally substituted alkoxy, optionally substituted alkoxy C 1 -C 6 alkyl, optionally substituted C 1 -C 6 alkyl, optionally substituted amino, optionally substituted C 1 -C 6 alkyl amino, optionally substituted heterocycloalkyl, optionally substituted C 1 -C 6 alkyl heterocycloalkyl, optionally substituted amino C 1 -C 6 alkyl, optionally substituted alkoxy C 1 -C 6 alkyl, —O—R 8 and —NR 9 R 10 ; R 3 is a group of formula —(CHR 6 ) n -A 2 or R 3 forms with the moiety CHR 5 from A 1 an optionally substituted ring selected from optionally substituted aryl and optionally substituted heteroaryl, or R 3 forms with the moiety NR 4 from A 1 an optionally substituted ring selected from optionally substituted aryl, optionally substituted heteroaryl; n is an integer from 0 to 4; R 4 is selected from H and optionally substituted alkyl; A 2 is an optionally substituted ring selected from optionally substituted aryl and optionally substituted heteroaryl; R 5 is selected from H, optionally substituted C 1 -C 6 alkyl, optionally substituted amino C 1 -C 6 alkyl, optionally substituted alkoxy C 1 -C 6 alkyl, optionally substituted heterocycloalkyl C 1 -C 6 alkyl, optionally substituted aminocarbonyl, optionally substituted C 2 -C 8 cycloalkyl and optionally substituted amino C 1 -C 6 alkyl; R 6 is selected from H, optionally substituted C 1 -C 6 alkyl, optionally substituted amino, optionally substituted C 1 -C 6 alkyl amino and hydroxy and wherein R 6 groups are independently selected for each repeating unit (CHR 6 ); R 7 is selected from H, halogen and optionally substituted C 1 -C 6 alkyl; R 8 is selected from H, optionally substituted C 1 -C 6 alkyl, optionally substituted amino C 1 -C 6 alkyl, optionally substituted heterocycloalkyl, optionally substituted C 2 -C 8 cycloalkyl, optionally substituted heterocycloalkyl C 1 -C 6 alkyl, optionally substituted C 2 -C 8 cycloalkyl C 1 -C 6 alkyl, optionally substituted alkoxy, optionally substituted amino C 1 -C 6 alkyl; optionally substituted aryl C 1 -C 6 alkyl and optionally substituted heteroaryl C 1 -C 6 alkyl; R 9 and R 10 are independently selected from H, optionally substituted C 1 -C 6 alkyl, optionally substituted amino C 1 -C 6 alkyl, optionally substituted heterocycloalkyl, optionally substituted C 2 -C 8 cycloalkyl, optionally substituted heterocycloalkyl C 1 -C 6 alkyl, optionally substituted C 2 -C 8 cycloalkyl C 1 -C 6 alkyl, optionally substituted alkoxy, optionally substituted alkoxy C 1 -C 6 alkyl, optionally substituted aryl C 1 -C 6 alkyl and optionally substituted heteroaryl C 1 -C 6 alkyl, optionally substituted amino C 1 -C 6 alkyl; as well as tautomers, geometrical isomers, optically active forms and pharmaceutically acceptable salts thereof.

2. The amido thiadiazole compound according to claim 1 , wherein X is N.

3. The amido thiadiazole compound according to claim 1 , wherein X is CR 1 .

4. The amido thiadiazole compound according to claim 1 , wherein Y is CH.

5. The amido thiadiazole compound according to claim 1 , wherein Y is N.

6. The amido thiadiazole compound according to claim 1 , wherein A 1 is —OCHR 5 —.

7. The amido thiadiazole compound according to claim 1 , wherein A 1 is —NR 4 —CHR 5 .

8. The amido thiadiazole compound according to claim 1 , wherein A 1 is —CH 2 NR 4 .

9. The amido thiadiazole compound according to claim 1 , wherein A 1 is —CH 2 —O—.

10. The amido thiadiazole compound according to claim 1 , wherein n is selected from 0, 1 and 2.

11. The amido thiadiazole compound according to claim 1 selected from the following group:

4-(1-phenylethoxy)-3-(piperidin-4-ylmethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-(2-hydroxyethoxy)-4-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

5-chloro-6-(2-(dimethylamino)-1-(pyridin-2-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

3-methoxy-4-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(1-(pyridin-2-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(2-(dimethylamino)-1-phenylethoxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(2-hydroxy-1-phenylethoxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(3-hydroxy-1-phenylpropoxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(1-phenyl-3-(pyrrolidin-1-yl)propoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(1-phenyl-2-(pyrrolidin-1-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(3-(dimethylamino)-1-phenylpropoxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(2-(methylamino)-1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(1-(pyridin-3-yl)ethoxy)-N-(5-(pyrimidin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

N-(5-(3-fluoropyridin-4-yl)-1,3,4-thiadiazol-2-yl)-3-methoxy-4-(1-(pyridin-3-yl)ethoxy)benzamide;

3-methoxy-N-(5-(3-methylpyridin-4-yl)-1,3,4-thiadiazol-2-yl)-4-(1-phenylethoxy)benzamide;

3-methoxy-N-(5-(2-methylpyridin-4-yl)-1,3,4-thiadiazol-2-yl)-4-(1-phenylethoxy)benzamide;

4-((1H-imidazol-4-yl)methoxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)-4-(pyrimidin-2-ylmethoxy)benzamide;

3-methoxy-4-((1-methyl-1H-imidazol-2-yl)methoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

5-methyl-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-chloro-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-((2-methoxyethyl)amino)-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(benzyloxy)-5-chloro-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(benzyloxy)-5-(4-methylpiperazin-1-yl)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-methoxy-6-((1-phenylethyl)amino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(3-(dimethylamino)-1-phenylpropoxy)-5-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(2-hydroxy-1-phenylethoxy)-5-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(2-hydroxy-2-phenylethoxy)-5-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-chloro-6-(2-hydroxy-2-methyl-1-phenylpropoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-chloro-6-(2-(dimethylamino)-1-(pyridin-2-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(2-(dimethylamino)-1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((1-(dimethylamino)-2,3-dihydro-1H-inden-2-yl)oxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6((1-(dimethylamino)-3-phenylpropan-2-yl)oxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((1-phenylpropan-2-yl)oxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(1-(pyridin-3-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((1-(pyridin-3-yl)ethyl)amino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl) nicotinamide;

6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)-5-((tetrahydro-2H-pyran-4-yl)methoxy)nicotinamide;

6-(3-morpholino-1-phenylpropoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(2-morpholino-1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

4-(isoindolin-2-ylmethyl)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

6-(benzyloxy)-5-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-methoxy-6-(1-phenyl ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl) nicotinamide;

2-methyl-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

2-methyl-6-(1-(pyridin-2-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(benzyloxy)-2-methyl-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-methoxy-6-(1-(pyridin-2-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-chloro-6-(1-(pyridin-2-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(benzyloxy)-5-((2-(dimethylamino)ethyl)amino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(benzyloxy)-5-methyl-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-((2-(dimethylamino)ethyl)amino)-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)-5-(((tetrahydro-2H-pyran-4-yl)methyl)amino)nicotinamide;

5-(((1-methylpiperidin-4-yl)methyl)amino)-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-(methylamino)-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(benzyloxy)-5-(methylamino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(3-(dimethylamino)-1-phenylpropoxy)-5-methyl-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-chloro-6-(3-(dimethylamino)-1-phenylpropoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(2-(dimethylamino)-1-phenylethoxy)-5-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-chloro-6-(2-(dimethylamino)-1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(2-(dimethylamino)-1-phenylethoxy)-5-methyl-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-((3-(dimethylamino)propyl)amino)-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-((2-hydroxyethyl)amino)-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-(((1-methyl-1H-imidazol-4-yl)methyl)amino)-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-((1-methylpiperidin-4-yl)amino)-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-((2-morpholinoethyl)amino)-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-(4-methylpiperazin-1-yl)-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-(dimethylamino)-6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-methoxy-6-((1-(pyridin-3-yl)ethyl)amino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(2-(dimethylamino)-1-(pyridin-2-yl)ethoxy)-5-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-(dimethylamino)-6-(3-(dimethylamino)-1-phenylpropoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(3-(dimethylamino)-1-phenylpropoxy)-5-(methylamino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)-4-(pyridin-4-ylmethoxy)benzamide;

3-methoxy-4-(1-(pyridin-3-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-((2,3-dihydro-1H-inden-1-yl)oxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)-4-((1,2,3,4-tetrahydronaphthalen-1-yl)oxy)benzamide;

3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)-4-(thiazol-4-ylmethoxy)benzamide;

3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)-4-(thiazol-2-ylmethoxy)benzamide;

3-(2-(dimethylamino)ethoxy)-4-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-(2-methoxyethoxy)-4-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-((1-methylpiperidin-4-yl)methoxy)-4-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-((2-methylpyridin-3-yl)methoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-((5-methylpyridin-2-yl)methoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-((5-methylisoxazol-3-yl)methoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-((4-methoxybenzyl)oxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-((2-fluorobenzyl)oxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(pyridin-2-ylmethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-((4-fluorobenzyl)oxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-((5-methyl-1,2,4-oxadiazol-3-yl)methoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide

4-((5-cyclopropylisoxazol-3-yl)methoxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-((1-methyl-1H-1,2,4-triazol-5-yl)methoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-((1-methyl-1H-imidazol-5-yl)methoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(2-(1-methyl-1H-imidazol-2-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(1-(pyridin-2-yl)ethoxy)-N-(5-(pyrimidin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

N-(5-(3-fluoropyridin-4-yl)-1,3,4-thiadiazol-2-yl)-3-methoxy-4-(1-(pyridin-2-yl)ethoxy)benzamide;

N-(5-(3-fluoropyridin-4-yl)-1,3,4-thiadiazol-2-yl)-4-(3-hydroxy-1-phenylpropoxy)-3-methoxybenzamide;

N-(5-(3-fluoropyridin-4-yl)-1,3,4-thiadiazol-2-yl)-4-(2-hydroxy-1-phenylethoxy)-3-methoxybenzamide;

4-(2-(dimethylamino)-1-phenylethoxy)-N-(5-(3-fluoropyridin-4-yl)-1,3,4-thiadiazol-2-yl)-3-methoxybenzamide;

6-(3-(dimethylamino)-1-phenylpropoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)-5-((tetrahydro-2H-pyran-4-yl)methoxy)nicotinamide;

5-chloro-6-(2-hydroxy-1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

4-(3-hydroxy-1-phenylpropoxy)-3-methoxy-N-(5-(pyrimidin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(2-hydroxy-1-phenylethoxy)-3-methoxy-N-(5-(pyrimidin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(benzyloxy)-3-methoxy-N-(5-(pyrimidin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(benzyloxy)-N-(5-(3-fluoropyridin-4-yl)-1,3,4-thiadiazol-2-yl)-3-methoxybenzamide;

4-(2-(dimethylamino)-1-phenylethoxy)-3-methoxy-N-(5-(3-methylpyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

6-(2-(dimethylamino)-1-phenylethoxy)-5-methoxy-N-(5-(pyrimidin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

4-(2-(dimethylamino)-1-phenylethoxy)-3-methoxy-N-(5-(2-methylpyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-((1-phenylpropan-2-yl)oxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(2-(dimethylamino)-1-phenylethoxy)-3-methoxy-N-(5-(pyrimidin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(benzyloxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-((methyl(pyridin-2-yl)amino)methyl)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-((1H-indo-1-yl)methyl)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(phenoxymethyl)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-((methyl(phenyl)amino)methyl)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

6-(2-hydroxy-2-methyl-1-phenylpropoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((1-phenylpropan-2-yl)oxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)-6-(thiophen-3-ylmethoxy)nicotinamide;

6-(3-(dimethylamino)-1-phenylpropoxy)-N-(5-(3-fluoropyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(1-phenylpropoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(1-(4-chlorophenyl)propoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((2,3-dihydro-1H-inden-1-yl)oxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((6,7-dihydro-5H-cyclopenta[b]pyridin-5-yl)oxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(3-(dimethylamino)-1-phenylpropoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(3-hydroxy-3-phenylpropoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(benzyloxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(methyl(1-phenylethyl)amino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((2-(dimethylamino)-2-phenylethyl)amino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((2,3-dihydro-1H-inden-2-yl)amino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((1-(pyridin-2-yl)ethyl)amino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((1-(pyridin-3-yl)propan-2-yl)amino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((1-phenylethyl)amino)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

4-((6,7-dihydro-5H-cyclopenta[b]pyridin-5-yl)oxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-((2,3-dihydrobenzofuran-3-yl)oxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(cyclopropyl(phenyl)methoxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(1-phenylethoxy)-N-(5-(pyrimidin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-((2,3-dihydro-1H-inden-2-yl)oxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(1-phenylpropoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-phenethoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-((1-methyl-1H-pyrazol-3-yl)methoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(pyridin-3-ylmethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(benzyloxy)-3-chloro-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(benzyloxy)-2-chloro-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(pyridin-3-ylmethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(benzyloxy)-2-fluoro-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(benzyloxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-phenoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

6-phenoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((1-(dimethylamino)-1-oxo-3-phenylpropan-2-yl)oxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-((4-phenylbutan-2-yl)oxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(2-phenylpropoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(3-(4-methoxyphenyl)propoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-methyl-6-(2-morpholino-1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

3-methoxy-4-(2-methoxy-1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-methoxy-4-(2-morpholino-1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

6-(3-(dimethylamino)-1-phenylpropoxy)-5-methoxy-N-(5-(pyrimidin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(2-(3,3-difluoropyrrolidin-1-yl)-1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(2-(4-methylpiperazin-1-yl)-1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

6-(1-phenyl-3-(pyrrolidin-1-yl)propoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-methoxy-6-(1-phenyl-2-(pyrrolidin-1-yl)ethoxy)-N-(5-(pyrimidin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-methoxy-6-(1-phenyl-2-(pyrrolidin-1-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-methyl-6-(1-phenyl-2-(pyrrolidin-1-yl)ethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

5-methoxy-6-(1-phenylethoxy)-N-(5-(pyrimidin-4-yl)-1,3,4-thiadiazol-2-yl)nicotinamide;

4-(2-(dimethylamino)-1-phenylethoxy)-3-fluoro-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

3-chloro-4-(2-(dimethylamino)-1-phenylethoxy)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide;

4-(1-(4-fluorophenyl)-2-hydroxyethoxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide; and

4-(2-(dimethylamino)-1-(4-fluorophenyl)ethoxy)-3-methoxy-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)benzamide.

12. A pharmaceutical composition comprising at least one amido thiadiazole compound according to claim 1 and a pharmaceutically acceptable carrier, diluent or excipient thereof.

Assignments (3)

CHANGE OF NAME Recorded Aug 3, 2017

From: GENKYOTEX SA

To: GENKYOTEX SUISSE SA

Reel/Frame 043431/0788 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 10, 2017

From: SHARPE, ANDREW; LOCK, CHRISTOPHER JAMES; CHAMBERS, MARK S.; HODGES, ALASTAIR; ALLEN, VIVIENNE; ELLARD, JOHN M.

To: GENKYOTEX SA

Reel/Frame 043138/0001 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 10, 2017

From: MACHIN, PETER

To: GENKYOTEX SA

Reel/Frame 043138/0211 →

Priority Claims (1)

EP 14198597 · Dec 17, 2014 · regional

Continuity (1)

Related Publication 20170348296A1 · Dec 7, 2017