US2010280002A1PendingUtilityA1
Aminopyridine-derivatives as inductible no-synthase inhibitors
Est. expiryOct 1, 2023(expired)· nominal 20-yr term from priority
Inventors:Thomas Fuchss
A61P 43/00A61P 9/10A61P 3/10A61P 25/00A61P 25/16A61P 25/06A61P 29/00A61P 25/04A61P 25/28A61P 31/00A61P 13/12A61P 21/04A61P 17/04A61P 17/00A61P 11/06C07D 471/04A61P 11/00A61P 1/00A61P 17/06A61P 11/16A61P 19/02A61P 19/06
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Claims
Abstract
The compounds of Formula (I) in which R1, R2, R3 and R4 have the meanings as given in the description are novel effective iNOS inhibitors.
Claims
exact text as granted — not AI-modified1 .- 15 . (canceled)
16 . A method for treating an acute inflammatory disease in a patient comprising administering to said patient a therapeutically effective amount of a compound of formula I
in which
R1 is hydrogen or 1-4C-alkyl,
R2 is hydrogen, halogen, hydroxyl, nitro, amino, 1-7C-alkyl, trifluoromethyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkoxy, completely or predominantly fluorine-substituted 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkoxycarbonyl, mono- or di-1-4C-alkylaminocarbonyl, mono- or di-1-4C-alkylaminosulfonyl, 1-4C-alkylcarbonylamino, 1-4C-alkylsulfonylamino, phenyl, R21- and/or R211-substituted phenyl, phenyl-1-4C-alkyl, phenyl-1-4C-alkyl wherein the phenyl moiety is substituted by R22, phenyl-1-4C-alkoxy, pyridyl, pyridyl substituted by R23, pyridyl-1-4C-alkyl, or pyridyl-1-4C-alkyl wherein the pyridyl moiety is substituted by R24, in which
R21 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, aminosulfonyl, mono- or di-1-4C-alkylaminosulfonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, phenylsulfonylamino, phenyl-1-4C-alkoxy, or —S(O) 2 -Het, in which
Het is bonded to the adjacent sulfonyl group via a ring nitrogen atom, and is a 3- to 7-membered fully saturated heterocyclic ring comprising one nitrogen atom, to which the sulfonyl group is attached, and optionally one further heteroatom selected from the group consisting of N(R210), oxygen and sulfur, in which
R210 is 1-4C-alkyl,
R211 is halogen or 1-4C-alkoxy,
R22 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R23 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R24 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy,
R4 is 1-4C-alkyl, or 1-4C-alkoxy,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
17 . The method according to claim 16 ,
in which
R1 is hydrogen or 1-2C-alkyl,
R2 is hydrogen, halogen, phenyl, or R21- and/or R211-substituted phenyl, in which
R21 is 1-4C-alkyl, cyano, halogen, mono- or di-1-4C-alkylamino, trifluoromethyl, mono- or di-1-4C-alkylaminosulfonyl, hydroxyl, phenyl-1-4C-alkoxy, or —S(O) 2 -Het, in which
Het is azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, or 4N—(R210)-piperazin-1-yl, in which
R210 is 1-4C-alkyl,
R211 is halogen,
R3 is hydrogen,
R4 is methyl, or methoxy,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
18 . The method according to claim 16 ,
in which
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, iodine, bromine, phenyl, or R21- and/or R211-substituted phenyl, in which
R21 is methyl, cyano, chlorine, fluorine, dimethylamino, trifluoromethyl, dimethylaminosulfonyl, hydroxyl, benzyloxy, or —S(O) 2 -Het, in which
Het is azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, or 4N-methyl-piperazin-1-yl, in which
R211 is chlorine,
R3 is hydrogen,
R4 is methyl, or methoxy,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
19 . The method according to claim 16 ,
in which
R1 is hydrogen or methyl,
R2 is bonded in the 6-position of the 3H-imidazo[4,5-b]pyridine ring, and is hydrogen, iodine, bromine, phenyl, 3-hydroxyl-phenyl, 4-(R21)-phenyl, or 3,5-di-chloro-phenyl, in which
R21 is methyl, cyano, chlorine, fluorine, dimethylamino, trifluoromethyl, dimethylaminosulfonyl, benzyloxy, or —S(O) 2 -Het, in which
Het is azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, or 4N-methyl-piperazin-1-yl, in which
R3 is hydrogen,
R4 is methyl, or methoxy,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
20 . The method according to claim 16 ,
in which
R1 is hydrogen or 1-4C-alkyl,
R2 is hydrogen, halogen, hydroxyl, nitro, amino, 1-7C-alkyl, trifluoromethyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkoxy, completely or predominantly fluorine-substituted 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkoxycarbonyl, mono- or di-1-4C-alkylaminocarbonyl, mono- or di-1-4C-alkylaminosulfonyl, 1-4C-alkylcarbonylamino, 1-4C-alkylsulfonylamino, phenyl, R21- and/or R211-substituted phenyl, phenyl-1-4C-alkyl, phenyl-1-4C-alkyl wherein the phenyl moiety is substituted by R22, phenyl-1-4C-alkoxy, pyridyl, pyridyl substituted by R23, pyridyl-1-4C-alkyl, pyridyl-1-4C-alkyl wherein the pyridyl moiety is substituted by R24, in which
R21 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, aminosulfonyl, mono- or di-1-4C-alkylaminosulfonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, phenylsulfonylamino or phenyl-1-4C-alkoxy,
R211 is halogen or 1-4C-alkoxy,
R22 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R23 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R24 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy,
R4 is 1-4C-alkyl,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
21 . The method according to claim 16 ,
in which
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, iodine, bromine, phenyl, or R21-substituted phenyl, in which
R21 is methyl, cyano, chlorine, fluorine, dimethylamino or trifluoromethyl,
R3 is hydrogen,
R4 is methyl,
or a salt, N-oxide or a salt of an N-oxide thereof.
22 . The method according to claim 16 ,
in which
R1 is hydrogen or methyl,
R2 is R21-substituted phenyl, in which
R21 is aminosulphonyl, mono- or di-1-4C-alkylaminosulfonyl, or —S(O) 2 -Het, in which
Het is azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, or 4N-(1-4C-alkyl)-piperazin-1-yl,
R3 is hydrogen,
R4 is methyl, or methoxy,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
23 . The method according to claim 16 , wherein the compound of formula I is of the formula Ia
in which
R1 is hydrogen,
R4 is methyl or methoxy, and
A is 6-(4-dimethylaminosulphonyl-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl, 6-(4-diethylaminosulphonyl-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl, 6-(4-methylaminosulphonyl-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl, 6-(4-aminosulphonyl-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl, 6-(4-ethylaminosulphonyl-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl, 6-[4-(azetidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl, 6-[4-(pyrrolidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl, 6-[4-(piperidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl, or 6-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
24 . The method according to claim 16 ,
in which
R1 is hydrogen,
R2 is bonded to the 6-position of the 3H-imidazo[4,5-b]pyridine ring,
R3 is hydrogen, and
R4 is methyl;
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
25 . The method according to claim 16 , wherein the compound is selected from the group consisting of:
a. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-3H-imidazo[4,5-b]pyridine, b. (R,S)-2-[3-(2-Amino-4-methylpyridin-6-yl)prop-2-yl]-3H-imidazo[4,5-b]pyridine, c. (R,S)-2-[4-(2-Amino-4-methylpyridin-6-yl)but-2-yl]-3H-imidazo[4,5-b]pyridine, d. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-bromo-3H-imidazo[4,5-b]pyridine, e. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-phenyl-3H-imidazo[4,5-b]pyridine, f. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-cyano-phenyl)-3H-imidazo[4,5-b]pyridine, g. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-p-tolyl-3H-imidazo[4,5-b]pyridine, h. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-fluoro-phenyl)-3H-imidazo[4,5-b]pyridine, i. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-dimethylamino-phenyl)-3H-imidazo[4,5-b]pyridine, j. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-chloro-phenyl)-3H-imidazo[4,5-b]pyridine, k. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-iodo-phenyl)-3H-imidazo[4,5-b]pyridine, l. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-trifluoromethyl-phenyl)-3H-imidazo[4,5-b]pyridine, m. 6-{2-[6-(3-Benzyloxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine, n. 6-{2-[6-(3,5-Dichloro-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine, o. 6-{2-[6-(4-Benzyloxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine, p. 3-{2-[2-(6-Amino-4-methyl-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-phenol, q. 6-(2-{6-[4-(Azetidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-4-methyl-pyridin-2-ylamine, r. 4-Methyl-6-(2-{6-[4-(pyrrolidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-pyridin-2-ylamine, s. 4-Methyl-6-(2-{6-[4-(piperidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-pyridin-2-ylamine, t. 4-{2-[2-(6-Amino-4-methyl-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N,N-dimethyl-benzenesulfonamide, u. 4-Methyl-6-(2-{6-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-pyridin-2-ylamine, v. 2-[2-(2-Amino-4-methoxypyridin-6-yl)ethyl]-3H-imidazo[4,5-b]pyridine
and the pharmaceutically acceptable salts, N-oxides and salts of the N-oxides thereof.
26 . A method for treating a chronic inflammatory disease of peripheral organs and the central nervous system (CNS) in a patient comprising administering to said patient a therapeutically effective amount of a compound of formula I
in which
R1 is hydrogen or 1-4C-alkyl,
R2 is hydrogen, halogen, hydroxyl, nitro, amino, 1-7C-alkyl, trifluoromethyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkoxy, completely or predominantly fluorine-substituted 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkoxycarbonyl, mono- or di-1-4C-alkylaminocarbonyl, mono- or di-1-4C-alkylaminosulfonyl, 1-4C-alkylcarbonylamino, 1-4C-alkylsulfonylamino, phenyl, R21- and/or R211-substituted phenyl, phenyl-1-4C-alkyl, phenyl-1-4C-alkyl wherein the phenyl moiety is substituted by R22, phenyl-1-4C-alkoxy, pyridyl, pyridyl substituted by R23, pyridyl-1-4C-alkyl, or pyridyl-1-4C-alkyl wherein the pyridyl moiety is substituted by R24, in which
R21 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, aminosulfonyl, mono- or di-1-4C-alkylaminosulfonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, phenylsulfonylamino, phenyl-1-4C-alkoxy, or —S(O) 2 -Het, in which
Het is bonded to the adjacent sulfonyl group via a ring nitrogen atom, and is a 3- to 7-membered fully saturated heterocyclic ring comprising one nitrogen atom, to which the sulfonyl group is attached, and optionally one further heteroatom selected from the group consisting of N(R210), oxygen and sulfur, in which
R210 is 1-4C-alkyl,
R211 is halogen or 1-4C-alkoxy,
R22 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R23 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R24 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy,
R4 is 1-4C-alkyl, or 1-4C-alkoxy,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
27 . The method according to claim 26 ,
in which
R1 is hydrogen or 1-2C-alkyl,
R2 is hydrogen, halogen, phenyl, or R21- and/or R211-substituted phenyl, in which
R21 is 1-4C-alkyl, cyano, halogen, mono- or di-1-4C-alkylamino, trifluoromethyl, mono- or di-1-4C-alkylaminosulfonyl, hydroxyl, phenyl-1-4C-alkoxy, or —S(O) 2 -Het, in which
Het is azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, or 4N—(R210)-piperazin-1-yl, in which
R210 is 1-4C-alkyl,
R211 is halogen,
R3 is hydrogen,
R4 is methyl, or methoxy,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
28 . The method according to claim 26 ,
in which
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, iodine, bromine, phenyl, or R21- and/or R211-substituted phenyl, in which
R21 is methyl, cyano, chlorine, fluorine, dimethylamino, trifluoromethyl, dimethylaminosulfonyl, hydroxyl, benzyloxy, or —S(O) 2 -Het, in which
Het is azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, or 4N-methyl-piperazin-1-yl, in which
R211 is chlorine,
R3 is hydrogen,
R4 is methyl, or methoxy,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
29 . The method according to claim 26 ,
in which
R1 is hydrogen or methyl,
R2 is bonded in the 6-position of the 3H-imidazo[4,5-b]pyridine ring, and is hydrogen, iodine, bromine, phenyl, 3-hydroxyl-phenyl, 4-(R21)-phenyl, or 3,5-di-chloro-phenyl, in which
R21 is methyl, cyano, chlorine, fluorine, dimethylamino, trifluoromethyl, dimethylaminosulfonyl, benzyloxy, or —S(O) 2 -Het, in which
Het is azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, or 4N-methyl-piperazin-1-yl, in which
R3 is hydrogen,
R4 is methyl, or methoxy,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
30 . The method according to claim 26 ,
in which
R1 is hydrogen or 1-4C-alkyl,
R2 is hydrogen, halogen, hydroxyl, nitro, amino, 1-7C-alkyl, trifluoromethyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkoxy, completely or predominantly fluorine-substituted 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkoxycarbonyl, mono- or di-1-4C-alkylaminocarbonyl, mono- or di-1-4C-alkylaminosulfonyl, 1-4C-alkylcarbonylamino, 1-4C-alkylsulfonylamino, phenyl, R21- and/or R211-substituted phenyl, phenyl-1-4C-alkyl, phenyl-1-4C-alkyl wherein the phenyl moiety is substituted by R22, phenyl-1-4C-alkoxy, pyridyl, pyridyl substituted by R23, pyridyl-1-4C-alkyl, pyridyl-1-4C-alkyl wherein the pyridyl moiety is substituted by R24, in which
R21 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, aminosulfonyl, mono- or di-1-4C-alkylaminosulfonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, phenylsulfonylamino or phenyl-1-4C-alkoxy,
R211 is halogen or 1-4C-alkoxy,
R22 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R23 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R24 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy,
R4 is 1-4C-alkyl,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
31 . The method according to claim 26 ,
in which
R1 is hydrogen, methyl or ethyl,
R2 is hydrogen, iodine, bromine, phenyl, or R21-substituted phenyl, in which
R21 is methyl, cyano, chlorine, fluorine, dimethylamino or trifluoromethyl,
R3 is hydrogen,
R4 is methyl,
or a salt, N-oxide or a salt of an N-oxide thereof.
32 . The method according to claim 26 ,
in which
R1 is hydrogen or methyl,
R2 is R21-substituted phenyl, in which
R21 is aminosulphonyl, mono- or di-1-4C-alkylaminosulfonyl, or —S(O) 2 -Het, in which
Het is azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, or 4N-(1-4C-alkyl)-piperazin-1-yl,
R3 is hydrogen,
R4 is methyl, or methoxy,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
33 . The method according to claim 26 , wherein the compound of formula I is of the formula Ia
in which
R1 is hydrogen,
R4 is methyl or methoxy, and
A is 6-(4-dimethylaminosulphonyl-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl, 6-(4-diethylaminosulphonyl-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl, 6-(4-methylaminosulphonyl-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl, 6-(4-aminosulphonyl-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl, 6-(4-ethylaminosulphonyl-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl, 6-[4-(azetidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl, 6-[4-(pyrrolidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl, 6-[4-(piperidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl, or 6-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
34 . The method according to claim 26 ,
in which
R1 is hydrogen,
R2 is bonded to the 6-position of the 3H-imidazo[4,5-b]pyridine ring,
R3 is hydrogen, and
R4 is methyl;
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof.
35 . The method according to claim 26 , wherein the compound is selected from the group consisting of:
a. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-3H-imidazo[4,5-b]pyridine, b. (R,S)-2-[3-(2-Amino-4-methylpyridin-6-yl)prop-2-yl]-3H-imidazo[4,5-b]pyridine, c. (R,S)-2-[4-(2-Amino-4-methylpyridin-6-yl)but-2-yl]-3H-imidazo[4,5-b]pyridine, d. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-bromo-3H-imidazo[4,5-b]pyridine, e. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-phenyl-3H-imidazo[4,5-b]pyridine, f. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-cyano-phenyl)-3H-imidazo[4,5-b]pyridine, g. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-p-tolyl-3H-imidazo[4,5-b]pyridine, h. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-fluoro-phenyl)-3H-imidazo[4,5-b]pyridine, i. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-dimethylamino-phenyl)-3H-imidazo[4,5-b]pyridine, j. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-chloro-phenyl)-3H-imidazo[4,5-b]pyridine, k. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-iodo-phenyl)-3H-imidazo[4,5-b]pyridine, l. 2-[2-(2-Amino-4-methylpyridin-6-yl)ethyl]-6-(4-trifluoromethyl-phenyl)-3H-imidazo[4,5-b]pyridine, m. 6-{2-[6-(3-Benzyloxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine, n. 6-{2-[6-(3,5-Dichloro-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine, o. 6-{2-[6-(4-Benzyloxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine, p. 3-{2-[2-(6-Amino-4-methyl-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-phenol, q. 6-(2-{6-[4-(Azetidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-4-methyl-pyridin-2-ylamine, r. 4-Methyl-6-(2-{6-[4-(pyrrolidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-pyridin-2-ylamine, s. 4-Methyl-6-(2-{6-[4-(piperidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-pyridin-2-ylamine, t. 4-{2-[2-(6-Amino-4-methyl-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N,N-dimethyl-benzenesulfonamide, u. 4-Methyl-6-(2-{6-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-pyridin-2-ylamine, v. 2-[2-(2-Amino-4-methoxypyridin-6-yl)ethyl]-3H-imidazo[4,5-b]pyridine
and the pharmaceutically acceptable salts, N-oxides and salts of the N-oxides thereof.
36 . A method for treating a disease or disorder in a patient comprising administering to said patient a therapeutically effective amount of a compound of formula I
in which
R1 is hydrogen or 1-4C-alkyl,
R2 is hydrogen, halogen, hydroxyl, nitro, amino, 1-7C-alkyl, trifluoromethyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkoxy, completely or predominantly fluorine-substituted 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkoxycarbonyl, mono- or di-1-4C-alkylaminocarbonyl, mono- or di-1-4C-alkylaminosulfonyl, 1-4C-alkylcarbonylamino, 1-4C-alkylsulfonylamino, phenyl, R21- and/or R211-substituted phenyl, phenyl-1-4C-alkyl, phenyl-1-4C-alkyl wherein the phenyl moiety is substituted by R22, phenyl-1-4C-alkoxy, pyridyl, pyridyl substituted by R23, pyridyl-1-4C-alkyl, or pyridyl-1-4C-alkyl wherein the pyridyl moiety is substituted by R24, in which
R21 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, aminosulfonyl, mono- or di-1-4C-alkylaminosulfonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, phenylsulfonylamino, phenyl-1-4C-alkoxy, or —S(O) 2 -Het, in which
Het is bonded to the adjacent sulfonyl group via a ring nitrogen atom, and is a 3- to 7-membered fully saturated heterocyclic ring comprising one nitrogen atom, to which the sulfonyl group is attached, and optionally one further heteroatom selected from the group consisting of N(R210), oxygen and sulfur, in which
R210 is 1-4C-alkyl,
R211 is halogen or 1-4C-alkoxy,
R22 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R23 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R24 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
R3 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy,
R4 is 1-4C-alkyl, or 1-4C-alkoxy,
or a pharmaceutically acceptable salt, N-oxide or salt of an N-oxide thereof, wherein the disease or disorder is selected from the group consisting of COPD, asthma, rheumatoid arthritis, osteoarthritis, neuropathic pain, Crohn's disease and ulcerative colitis.Join the waitlist — get patent alerts
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