IP Library Granted Patent US 8,816,085
Granted Patent B2
US 8,816,085 · App. 13/390,942 · Granted Aug 26, 2014

Methylpyrrolopyridinecarboxamides

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Quick Facts
Patent No.
US 8,816,085
App. No.
13/390,942
Granted
Aug 26, 2014
Kind
B2
Abstract

The compounds of Formula (I), wherein R1, R21, R22, R23, R24, Y and R3 have the meanings as given in the description, the salts thereof, the stereoisomers of the compounds and the salts thereof are effective inhibitors of the type 5 phosphodiesterase.

Claims (86)

1. A compound of formula (I)

wherein

R1 is —CH 2 -3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,

R11 is 1-4C-alkoxy or hydroxy,

R21 is hydrogen,

R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy, —C(±)-1-4C-alkyl or 1-4C-fluoroalkyl,

or R21 and R22 combine to form a group —O—CH 2 —O—,

R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,

or R22 and R23 combine to form a group —O—CH 2 —O—,

R24 is hydrogen,

Y is —(CH 2 ) n —,

n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4 and/or R5, or a 3-6C-cycloalkyl group substituted by R6,

R4 is —C(O)—H, —C(±)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, —C(±)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or —C(O)—O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,

R41 is 1-4C-alkoxy or hydroxy,

R42 is 1-4C-alkoxy or hydroxy,

R43 is 1-4C-alkoxy or hydroxy,

R5 is 1-4C-alkoxy, hydroxy or halogen,

R6 is —NH—C(O)—R7, —C(O)—NR8R9 or NH 2 ,

R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,

R71 is 1-4C-alkoxy or hydroxy,

R72 is 1-4C-alkoxy or hydroxy,

R73 is 1-4C-alkoxy or hydroxy,

R8 is hydrogen,

R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally substituted by R92,

R91 is 1-4C-alkoxy or hydroxy,

R92 is 1-4C-alkoxy or hydroxy,

or a salt thereof, a stereoisomer of the compound or a salt of the stereoisomer.

2. The compound according to claim 1 , wherein

R1 is —CH 2 -3-4C-cycloalkyl or 2-4C-alkyl,

R21 is hydrogen,

R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-fluoroalkoxy, —C(O)-1-4C-alkyl or 1-4C-fluoroalkyl,

or R21 and R22 combine to form a group —O—CH 2 —O—,

R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,

R24 is hydrogen,

Y is —(CH 2 ) n —,

n is 0,

R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4 and/or R5, or a 3-6C-cycloalkyl group substituted by R6,

R4 is —C(O)—H, —C(±)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, or —C(O)—O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,

R41 is 1-4C-alkoxy or hydroxy,

R43 is 1-4C-alkoxy or hydroxy,

R6 is —NH—C(O)—R7 or NH 2 ,

R5 is 1-4C-alkoxy, hydroxy or fluoro,

R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, or 1-4C-alkoxy, which is optionally substituted by R73,

R71 is 1-4C-alkoxy or hydroxy,

R73 is 1-4C-alkoxy or hydroxy,

or a salt thereof, a stereoisomer of the compound or a salt of the stereoisomer.

3. The compound according to claim 1 , wherein

R1 is —CH 2 -3-4C-cycloalkyl,

R21 is hydrogen,

R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-fluoroalkoxy, —C(±)-1-4C-alkyl or 1-4C-fluoroalkyl,

or R21 and R22 combine to form a group —O—CH 2 —O—,

R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,

R24 is hydrogen,

Y is —(CH 2 ) n —,

n is 0,

R3 is a 5- to 6-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4 and/or R5, or a 3-6C-cycloalkyl group substituted by R6,

R4 is —C(±)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, or —C(O)—O-1-4C-alkyl,

R41 is 1-4C-alkoxy or hydroxy,

R5 is hydroxy,

R6 is —NH—C(O)—R7 or NH 2 ,

R7 is 1-4C-alkyl, which is optionally substituted by R71, or 1-4C-alkoxy,

R71 is 1-4C-alkoxy or hydroxy,

or a salt thereof, a stereoisomer of the compound or a salt of the stereoisomer.

4. The compound according to claim 1 , wherein

R1 is —CH 2 -3-4C-cycloalkyl,

R21 is hydrogen,

R22 is hydrogen, halogen, 1-4C-alkyl or 1-2C-alkoxy,

or R21 and R22 combine to form a group —O—CH 2 —O—,

R23 is hydrogen, halogen or 1-2C-alkoxy,

R24 is hydrogen,

Y is —(CH 2 ) n —,

n is 0,

R3 is a 5- to 6-membered saturated heterocyclic ring containing one nitrogen atom, said heterocyclic ring being substituted by R4 at said nitrogen atom and said heterocyclic ring being optionally substituted by R5, or a cyclohexyl group substituted by R6,

R4 is —C(±)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, or —C(O)—O-1-4C-alkyl,

R41 is 1-4C-alkoxy or hydroxy,

R5 is hydroxy,

R6 is —NH—C(O)—R7,

R7 is 1-4C-alkyl, which is optionally substituted by R71, or 1-4C-alkoxy,

R71 is 1-4C-alkoxy or hydroxy,

or a salt thereof, a stereoisomer of the compound or a salt of the stereoisomer.

5. A compound according to claim 1 selected from the group consisting of

tert-Butyl 4-[({7-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]piperidine-1-carboxylate; tert-Butyl {trans-4-[({7-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({7-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl 4-{[(7-[2-(cyclopropylmethoxy)-4-fluorophenyl]-2-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[3,2-b]pyridin-3-yl)carbonyl]amino}piperidine-1-carboxylate; tert-Butyl {trans-4-[({7-[2-(cyclopropylmethoxy)-4-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({7-[2-(cyclopropylmethoxy)-4-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl 4-[({7-[2-(cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]piperidine-1-carboxylate; tert-Butyl {trans-4-[({7-[2-(cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({7-[2-(cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl (3R*,4R*)-4-[({7-[2-(cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]-3-hydroxypiperidine-1-carboxylate; tert-Butyl 4-[({7-[2-(cyclopropylmethoxy)-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]piperidine-1-carboxylate; tert-Butyl {trans-4-[({7-[2-(cyclopropylmethoxy)-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({7-[2-(cyclopropylmethoxy)-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl 4-[({7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]piperidine-1-carboxylate; tert-Butyl {trans-4-[({7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl-(3R*,4R*)-3-[({7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]-4-hydroxypyrrolidine-1-carboxylate; tert-Butyl 4-[({7-[2-(cyclopropylmethoxy)-5-methylphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]piperidine-1-carboxylate; tert-Butyl {trans-4-[({7-[2-(cyclopropylmethoxy)-5-methylphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({7-[2-(cyclopropylmethoxy)-5-methylphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl 4-[({7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]piperidine-1-carboxylate; tert-Butyl {trans-4-[({7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl (3R*,4R*)-3-[({7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]-4-hydroxypyrrolidine-1-carboxylate; tert-Butyl (3R*,4R*)-4-[({7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]-3-hydroxypiperidine-1-carboxylate; tert-Butyl 4-[({7-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]piperidine-1-carboxylate; tert-Butyl {trans-4-[({7-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({7-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; N-(1-Acetylpiperidin-4-yl)-7-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-2-methyl-N-(1-propionylpiperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-N-[1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; Ethyl 4-[({7-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]piperidine-1-carboxylate; N-(trans-4-Acetamidocyclohexyl)-7-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-(cis-4-acetamidocyclohexyl)-7-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-2-methyl-N-[cis-4-(propionylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; Ethyl {cis-4-[({7-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl}carbonyl)amino]cyclohexyl}carbamate; N-(1-Acetylpiperidin-4-yl)-7-[2-(cyclopropylmethoxy)-4-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-2-methyl-N-(1-propanoylpiperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-N-[1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[trans-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-4-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-2-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[cis-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-4-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-N-[cis-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-(1-Acetylpiperidin-4-yl)-7-[2-(cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-N-(1-propanoylpiperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-[1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[trans-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[cis-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-N-[cis-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[(3R*,4R*)-1-Acetyl-3-hydroxypiperidin-4-yl]-7-[2-(cyclopropylmethoxy)-5-fluorophenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-[(3R*,4R*)-3-hydroxy-1-propanoylpiperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-[(3R*,4R*)-3-hydroxy-1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-(1-Acetylpiperidin-4-yl)-7-[2-(cyclopropylmethoxy)-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-2-methyl-N-(1-propanoylpiperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-N-[1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[trans-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-2-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[cis-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-2-methyl-N-[cis-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-(1-Acetylpiperidin-4-yl)-7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-N-(1-propanoylpiperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-N-[1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[trans-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[cis-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-N-[cis-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[(3R*,4R*)-1-Acetyl-4-hydroxypyrrolidin-3-yl]-7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-[(3R*,4R*)-4-hydroxy-1-propanoylpyrrolidin-3-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-[(3R*,4R*)-4-hydroxy-1-(methoxyacetyl)pyrrolidin-3-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-(1-Acetylpiperidin-4-yl)-7-[2-(cyclopropylmethoxy)-5-methylphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methylphenyl]-2-methyl-N-(1-propanoylpiperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methylphenyl]-N-[1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[trans-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-5-methylphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methylphenyl]-2-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methylphenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[cis-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-5-methylphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methylphenyl]-2-methyl-N-[cis-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methylphenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-(1-Acetylpiperidin-4-yl)-7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-N-(1-propanoylpiperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-[1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[trans-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[cis-4-(Acetylamino)cyclohexyl]-7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-N-[cis-4-(propanoylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[(3R*,4R*)-1-Acetyl-4-hydroxypyrrolidin-3-yl]-7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-[(3R*,4R*)-4-hydroxy-1-propanoylpyrrolidin-3-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-[(3R*,4R*)-4-hydroxy-1-(methoxyacetyl)pyrrolidin-3-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-[(3R*,4R*)-1-Acetyl-3-hydroxypiperidin-4-yl]-7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-[(3R*,4R*)-3-hydroxy-1-propanoylpiperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-[(3R*,4R*)-3-hydroxy-1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-(1-Acetylpiperidin-4-yl)-7-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-2-methyl-N-(1-propionylpiperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-[1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-(trans-4-Acetamidocyclohexyl)-7-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-2-methyl-N-[trans-4-(propionylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; N-(cis-4-Acetamidocyclohexyl)-7-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-2-methyl-N-[cis-4-(propionylamino)cyclohexyl]-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 4-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-N-(1-glycoloylpiperidin-4-yl)-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 7-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-N-{1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-N-[1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-N-[cis-4-(glycoloylamino)cyclohexyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-N-(cis-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-N-[1-(methoxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-N-{1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-N-{trans-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-N-(trans-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-N-{cis-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-N-(cis-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-[1-(hydroxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-{1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-{trans-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-(trans-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-{cis-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-(cis-4-{[abs.(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-[rel.(3R,4R)-3-hydroxy-1-(hydroxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-{(3R,4R)-3-hydroxy-1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(cyclopropylmethoxy)-5-fluorophenyl]-N-{(3S,4S)-3-hydroxy-1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-N-[1-(hydroxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-N-{1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-N-{trans-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-N-(trans-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-N-{cis-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-methoxyphenyl]-N-(cis-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-[1-(hydroxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-{1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-{trans-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-(trans-4-{[abs.(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-{cis-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-(cis-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-[(3R*,4R*)-4-hydroxy-1-(hydroxyacetyl)pyrrolidin-3-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-{(3R*,4R*)-4-hydroxy-1-[(2S)-2-hydroxypropanoyl]pyrrolidin-3-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-N-{(3S*,4S*)-4-hydroxy-1-[(2S)-2-hydroxypropanoyl]pyrrolidin-3-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methylphenyl]-N-[1-(hydroxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(cyclopropylmethoxy)-5-methylphenyl]-N-{1-[abs.(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methylphenyl]-N-{trans-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methylphenyl]-N-(trans-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methylphenyl]-N-{cis-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-methylphenyl]-N-(cis-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-[1-(hydroxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-{1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-{trans-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-(trans-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-{cis-4-[(hydroxyacetyl)amino]cyclohexyl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-(cis-4-{[abs.(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-[(3R*,4R*)-4-hydroxy-1-(hydroxyacetyl)pyrrolidin-3-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-{(3R,4R)-4-hydroxy-1-[(2S)-2-hydroxypropanoyl]pyrrolidin-3-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-{(3S,4S)-4-hydroxy-1-[(2S)-2-hydroxypropanoyl]pyrrolidin-3-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-[(3R*,4R*)-3-hydroxy-1-(hydroxyacetyl)piperidin-4-yl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-{(3R,4R)-3-hydroxy-1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-{(3S,4S)-3-hydroxy-1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-(1-glycoloylpiperidin-4-yl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-{1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl}-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-[trans-4-(glycoloylamino)cyclohexyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-(trans-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-[cis-4-(glycoloylamino)cyclohexyl]-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide; 7-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-(cis-4-{[(2S)-2-methoxypropanoyl]amino}cyclohexyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;

and the salts, stereoisomers and salts of the stereoisomers thereof.

6. A pharmaceutical composition comprising at least one of the compounds, pharmaceutically acceptable salts thereof, stereoisomers of the compounds or the pharmaceutically acceptable salts thereof according to claim 1 , together with at least one pharmaceutically acceptable auxiliary.

7. The pharmaceutical composition according to claim 6 further comprising at least one therapeutic agent selected from the group consisting of corticosteroids, anticholinergics, beta-mimetics, lung surfactants, endothelin antagonists, prostacyclins, calcium channel blockers, beta-blockers, type 4 phosphodiesterase inhibitors, guanyl-cyclase activators/stimulators, pirfenidone, antidepressants and antibiotics.

Assignments (5)
CHANGE OF NAME Recorded Jul 29, 2015
From: NYCOMED GERMANY HOLDING GMBH
To: TAKEDA GMBH
Reel/Frame 036205/0192 →
MERGER Recorded Jul 28, 2015
From: TAKEDA GMBH
To: NYCOMED ASSET MANAGEMENT GMBH
Reel/Frame 036193/0178 →
MERGER Recorded Jul 28, 2015
From: NYCOMED ASSET MANAGEMENT GMBH
To: NYCOMED GERMANY HOLDING GMBH
Reel/Frame 036201/0261 →
CHANGE OF NAME Recorded Mar 21, 2013
From: NYCOMED GMBH
To: TAKEDA GMBH
Reel/Frame 030062/0206 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2012
From: BERNSMANN, HEIKO; SUDAU, ALEXANDER; DUNKERN, TORSTEN; STADLWIESER, JOSEF; SCHMIDT, BEATE; BENEDIKTUS, EWALD; PAHL, ANDREAS; HUSSONG, RAGNA
To: NYCOMED GMBH
Reel/Frame 027758/0866 →