Imidazopyridine derivatives useful as inos inhibitors

Abstract

The compounds of formula (I) in which R1, R11 and A have the meanings as given in the description are novel effective iNOS inhibitors.

1 - 15 . (canceled) 
     
     
         16 . A method of treating an acute inflammatory disease in a patient comprising administering to said patient a compound of formula I 
       
         
           
           
               
               
           
         
         in which 
         A is 1-4C-alkylene or 3-7C-cycloalkylene, 
         R1 is phenyl, R2— and/or R3-substituted phenyl, Har1, or R4— and/or R5-substituted Har1, 
         R11 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy, in which 
         R2 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, 1-4C-alkylsulfonylamino, phenylsulfonylamino, phenyl-1-4C-alkoxy, or —SO 2 —N(R21)R22, in which 
         R21 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, phenyl-1-4C-alkyl, Har2-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl, pyridyl, or R211- and/or R212-substituted phenyl, in which 
         Har2 is pyridyl, thienyl, furyl or tetrahydrofuryl, 
         R211 is 1-4C-alkyl, halogen, 1-4C-alkoxy, or mono- or di-1-4C-alkylamino, 
         R212 is 1-4C-alkyl or halogen, 
         R22 is hydrogen, 1-4C-alkyl, hydroxy-2-4C-alkyl or 1-4C-alkoxy-2-4C-alkyl, 
         or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which 
         Het1 is a fully saturated or partially unsaturated mono- or fused bicyclic ring or ring system made up of
 a first constituent being a 3- to 7-membered monocyclic fully saturated non-aromatic heterocyclic ring B,
 which heterocyclic ring B comprises one to three heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, 
 and which heterocyclic ring B is optionally substituted by one or two oxo groups, and, optionally, fused to said first constituent, 
 
 
         a second constituent being a benzene ring, 
         and which ring Het1 is optionally substituted by R23 on a ring carbon atom, 
         and/or which ring Het1 is optionally substituted by R24 on a further ring carbon atom, 
         and/or which ring Het1 is optionally substituted by an ethylenedioxy group on a ring carbon atom, 
         and/or which ring Het1 is optionally substituted by R25 on a ring nitrogen atom, 
         in which 
         R23 is 1-4C-alkyl, 1-4C-alkoxy or phenylcarbonyl, 
         R24 is 1-4C-alkyl or 1-4C-alkoxy, 
         R25 is 1-4C-alkyl, phenyl-1-4C-alkyl, 1-4C-alkylcarbonyl, 1-4C-alkoxy-2-4C-alkyl, mono- or di-1-4C-alkylamino-2-4C-alkyl, phenyl, pyrimidyl, pyridyl, formyl, 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl, or R251- and/or R252-substituted phenyl, in which 
         R251 is halogen, cyano or 1-4C-alkyl, 
         R252 is halogen or 1-4C-alkyl, 
         R3 is hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, 1-4C-alkoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy, 
         Har1 is bonded to the parent molecular group via a ring carbon atom, and is a monocyclic or fused bicyclic 5- to 10-membered unsaturated or partially saturated heteroaryl radical comprising one to three heteroatoms, each of which is selected from the group consisting of nitrogen, oxygen and sulfur, 
         R4 is 1-4C-alkyl, halogen, cyano, trifluoromethyl, phenyl, mono- or di-1-4C-alkylamino, formyl, 1-4C-alkylcarbonyl, carboxyl or 1-4C-alkoxy, 
         R5 is 1-4C-alkyl or halogen, 
       
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof, wherein the acute inflammatory disease is selected from the group consisting of acute lung injury, acute respiratory distress syndrome (ARDS), uveitis, glaucoma and conjunctivitis. 
     
     
         17 . The method according to  claim 16   in which   A is 1-4C-alkylene or 3-7C-cycloalkylene,   R1 is phenyl, R2— and/or R3-substituted phenyl, Har1, or R4— and/or R5-substituted Har1,   R11 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy,   in which   R2 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, 1-4C-alkylsulfonylamino, phenylsulfonylamino, phenyl-1-4C-alkoxy, or —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, phenyl-1-4C-alkyl, Har2-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl, pyridyl, or R211- and/or R212-substituted phenyl, in which   Har2 is pyridyl, thienyl or furyl,   R211 is 1-4C-alkyl, halogen, 1-4C-alkoxy, or mono- or di-1-4C-alkylamino,   R212 is 1-4C-alkyl or halogen,   R22 is hydrogen, 1-4C-alkyl, hydroxy-2-4C-alkyl or 1-4C-alkoxy-2-4C-alkyl,   or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is a fully saturated or partially unsaturated mono- or fused bicyclic ring or ring system made up of
 a first constituent being a 3- to 7-membered monocyclic fully saturated non-aromatic heterocyclic ring B,
 which heterocyclic ring B comprises one to three heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, 
 and which heterocyclic ring B is optionally substituted by one or two oxo groups, 
 
 and, optionally, fused to said first constituent, 
   a second constituent being a benzene ring,   and which ring Het1 is optionally substituted by R23 on a ring carbon atom,   and/or which ring Het1 is optionally substituted by R24 on a further ring carbon atom,   and/or which ring Het1 is optionally substituted by an ethylenedioxy group on a ring carbon atom,   and/or which ring Het1 is optionally substituted by R25 on a ring nitrogen atom,   in which   R23 is 1-4C-alkyl, 1-4C-alkoxy or phenylcarbonyl,   R24 is 1-4C-alkyl or 1-4C-alkoxy,   R25 is 1-4C-alkyl, phenyl-1-4C-alkyl, 1-4C-alkylcarbonyl, 1-4C-alkoxy-2-4C-alkyl, mono- or di-1-4C-alkylamino-2-4C-alkyl, phenyl, pyrimidyl, pyridyl, formyl, 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl, or R251- and/or R252-substituted phenyl, in which   R251 is halogen, cyano or 1-4C-alkyl,   R252 is halogen or 1-4C-alkyl,   R3 is hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, 1-4C-alkoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy, Har1 is bonded to the parent molecular group via a ring carbon atom, and is a monocyclic or fused bicyclic 5- to 10-membered unsaturated or partially saturated heteroaryl radical comprising one to three heteroatoms, each of which is selected from the group consisting of nitrogen, oxygen and sulfur,   R4 is 1-4C-alkyl, halogen, cyano, trifluoromethyl, phenyl, mono- or di-1-4C-alkylamino, formyl, 1-4C-alkylcarbonyl, carboxyl or 1-4C-alkoxy,   R5 is 1-4C-alkyl or halogen,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         18 . The method according to  claim 16   in which   A is ethylene or cyclopropylene,   R1 is bonded to the 6-position of the imidazopyridine scaffold, and is phenyl, R2- and/or R3-substituted phenyl, or Hart   R11 is hydrogen,   in which   R2 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, 1-4C-alkylsulfonylamino, phenylsulfonylamino, phenyl-1-4C-alkoxy, or —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, phenyl-1-4C-alkyl, Har2-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl, pyridyl, or R211- and/or R212-substituted phenyl, in which   Har2 is pyridyl, thienyl or furyl,   R211 is 1-4C-alkyl, halogen, 1-4C-alkoxy, or mono- or di-1-4C-alkylamino,   R212 is 1-4C-alkyl or halogen,   R22 is hydrogen, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl or 1-4C-alkyl,   or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is piperidinyl, pyrrolidinyl, azetidinyl, morpholinyl, thiomorpholinyl, S-oxo-thiomorpholinyl or S,S-dioxo-thiomorpholinyl, indolinyl, isoindolinyl, 1,2,3,4-tetrahydroquinolinyl, 1,2,3,4-tetrahydroisoquinolinyl, piperazinyl, homopiperazinyl, 4N—(R25)-piperazinyl, 4N—(R25)-homopiperazinyl, 2-oxopyrrolidinyl, 2-oxoimidazolidinyl, 2-oxopiperidinyl, 2,5-dioxopyrrolidinyl, 2,5-dioxoimidazolidinyl, 2,6-dioxopiperidinyl, 2-oxopiperazinyl, 2,6-dioxopiperazinyl, 5-oxo-1,4-diazepanyl, 3-(R25)-imidazolidin-2-one-yl, 3-(R25)-imidazolidin-2,5-dione-yl, 4-(R25)-piperazine-2-one-yl, 4-(R25)-piperazine-2,6-dione-yl or 4-(R25)-1,4-diazepan-5-one-yl, in which   R25 is 1-4C-alkyl, phenyl-1-4C-alkyl, 1-4C-alkylcarbonyl, 1-4C-alkoxy-2-4C-alkyl, mono- or di-1-4C-alkylamino-2-4C-alkyl, phenyl, pyrimidyl, pyridyl, formyl, 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl, or R251- and/or R252-substituted phenyl, in which   R251 is halogen, cyano or 1-4C-alkyl,   R252 is halogen or 1-4C-alkyl,   R3 is hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, 1-4C-alkoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy,   Har1 is bonded to the parent molecular group via a ring carbon atom, and is pyridyl, thienyl, furanyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzothiazolyl, quinolyl or isoquinolyl,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         19 . The method according to  claim 16   in which   A is ethylene,   R1 is bonded to the 6-position of the imidazopyridine scaffold, and is phenyl, or R2— and/or R3-substituted phenyl,   R11 is hydrogen,   in which   R2 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, 1-4C-alkylsulfonylamino, phenylsulfonylamino, or phenyl-1-4C-alkoxy,   R3 is hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, 1-4C-alkoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         20 . The method according to  claim 16   in which   A is ethylene,   R1 is bonded to the 6-position of the imidazopyridine scaffold, and is R2- and/or R3-substituted phenyl or Har1,   R11 is hydrogen,   in which   R2 is —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, phenyl-1-4C-alkyl, Har2-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl, pyridyl, or R211- and/or R212-substituted phenyl, in which   Har2 is pyridyl, thienyl or furyl,   R211 is 1-4C-alkyl, halogen, 1-4C-alkoxy, or mono- or di-1-4C-alkylamino,   R212 is 1-4C-alkyl or halogen,   R22 is hydrogen, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl or 1-4C-alkyl,   or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is piperidinyl, pyrrolidinyl, azetidinyl, morpholinyl, thiomorpholinyl, S-oxo-thiomorpholinyl or S,S-dioxo-thiomorpholinyl, indolinyl, isoindolinyl, 1,2,3,4-tetrahydroquinolinyl, 1,2,3,4-tetrahydroisoquinolinyl, piperazinyl, homopiperazinyl, 4N—(R25)-piperazinyl, 4N—(R25)-homopiperazinyl, 2-oxopyrrolidinyl, 2-oxoimidazolidinyl, 2-oxopiperidinyl, 2,5-dioxopyrrolidinyl, 2,5-dioxoimidazolidinyl, 2,6-dioxopiperidinyl, 2-oxopiperazinyl, 2,6-dioxopiperazinyl, 5-oxo-1,4-diazepanyl, 3-(R25)-imidazolidin-2-one-yl, 3-(R25)-imidazolidin-2,5-dione-yl, 4-(R25)-piperazine-2-one-yl, 4-(R25)-piperazine-2,6-dione-yl or 4-(R25)-1,4-diazepan-5-one-yl, in which   R25 is 1-4C-alkyl, phenyl-1-4C-alkyl, 1-4C-alkylcarbonyl, 1-4C-alkoxy-2-4C-alkyl, mono- or di-1-4C-alkylamino-2-4C-alkyl, phenyl, pyrimidyl, pyridyl, formyl, 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl, or R251- and/or R252-substituted phenyl, in which R251 is halogen, cyano or 1-4C-alkyl,   R252 is halogen or 1-4C-alkyl,   R3 is hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, 1-4C-alkoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy,   Har1 is bonded to the parent molecular group via a ring carbon atom, and is pyridyl, thienyl, furanyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzothiazolyl, quinolyl or isoquinolyl,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         21 . The method according to  claim 16   in which   A is 1-4C-alkylene,   R1 is phenyl, R2-substituted phenyl or Hart   R11 is hydrogen,   in which   R2 is cyano, 1-4C-alkoxy or —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, Har2-1-4C-alkyl, phenyl or R211- and/or R212-substituted phenyl, in which   Har2 is furyl or tetrahydrofuranyl,   R211 is 1-4C-alkyl or halogen,   R212 is 1-4C-alkyl or halogen,   R22 is hydrogen or 1-4C-alkyl,   or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is a 3- to 7-membered monocyclic fully saturated non-aromatic heterocyclic ring B, which heterocyclic ring B comprises one to three heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur,   and which ring Het1 is optionally substituted by R23 on a ring carbon atom,   and/or which ring Het1 is optionally substituted by R25 on a ring nitrogen atom,   in which   R23 is 1-4C-alkyl,   R25 is 1-4C-alkyl,   Har1 is bonded to the parent molecular group via a ring carbon atom, and is a monocyclic or fused bicyclic 5- to 10-membered unsaturated heteroaryl radical comprising one to three heteroatoms, each of which is selected from the group consisting of nitrogen, oxygen and sulfur,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         22 . The method according to  claim 16   in which   A is ethylene,   R1 is phenyl, R2-substituted phenyl or Hart   R11 is hydrogen,   in which   R2 is cyano, 1-4C-alkoxy or —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, Har2-1-4C-alkyl or R211- and/or R212-substituted phenyl, in which   Har2 is tetrahydrofuranyl,   R211 is 1-4C-alkyl or halogen,   R212 is 1-4C-alkyl,   R22 is hydrogen or 1-4C-alkyl,   or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is a 4- to 6-membered monocyclic fully saturated non-aromatic heterocyclic ring B, which heterocyclic ring B comprises one to three nitrogen atoms,   and which ring Het1 is optionally substituted by R25 on a ring nitrogen atom,   in which   R25 is 1-4C-alkyl,   Har1 is bonded to the parent molecular group via a ring carbon atom, and is a fused bicyclic 9-membered unsaturated heteroaryl radical comprising one oxygen atom,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         23 . The method according to  claim 16   in which   A is ethylene,   R1 is phenyl, R2-substituted phenyl or Hart   R11 is hydrogen,   in which   R2 is cyano, 1-4C-alkoxy or —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, Har2-1-4C-alkyl or R211- and/or R212-substituted phenyl, in which   Har2 is tetrahydrofuranyl,   R211 is 1-4C-alkyl or halogen,   R212 is 1-4C-alkyl,   R22 is hydrogen or 1-4C-alkyl,   or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is an azetidinyl or piperazinyl ring, which ring Het1 is optionally substituted by R25 on a ring nitrogen atom, in which   R25 is 1-4C-alkyl,   Har1 is bonded to the parent molecular group via a ring carbon atom, and is a benzofuranyl ring,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         24 . The method according to  claim 16 , wherein the compound is selected from the group consisting of 7-[2-(6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 7-[2-(6-{4-cyano-phen-1-yl}-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 7-{2-[6-(4-methoxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 7-[2-(6-benzofuran-2-yl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 4-{2-[2-(7-amino-3,4,5,6-tetrahydro-2H-azepin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N,N-dimethyl-benzenesulfonamide, 7-(2-{6-[4-(azetidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 7-(2-{6-[4-(4-ethyl-piperazine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 4-{2-[2-(7-amino-3,4,5,6-tetrahydro-2H-azepin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N-(2-fluoro-4-methyl-phenyl)-benzenesulfonamide, 4-{2-[2-(7-amino-3,4,5,6-tetrahydro-2H-azepin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N-o-tolyl-benzenesulfonamide and 4-{2-[2-(7-amino-3,4,5,6-tetrahydro-2H-azepin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N-methyl-N-(tetrahydro-furan-2-ylmethyl)-benzenesulfonamide. 
     
     
         25 . A method of treating a chronic inflammatory disease of a peripheral organ or central nervous system in a patient comprising administering to said patient a compound of formula I 
       
         
           
           
               
               
           
         
         in which 
         A is 1-4C-alkylene or 3-7C-cycloalkylene, 
         R1 is phenyl, R2- and/or R3-substituted phenyl, Har1, or R4- and/or R5-substituted Har1, 
         R11 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy, 
         in which 
         R2 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, 1-4C-alkylsulfonylamino, phenylsulfonylamino, phenyl-1-4C-alkoxy, or —SO 2 —N(R21)R22, in which 
         R21 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, phenyl-1-4C-alkyl, Har2-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl, pyridyl, or R211- and/or R212-substituted phenyl, in which 
         Har2 is pyridyl, thienyl, furyl or tetrahydrofuryl, 
         R211 is 1-4C-alkyl, halogen, 1-4C-alkoxy, or mono- or di-1-4C-alkylamino, 
         R212 is 1-4C-alkyl or halogen, 
         R22 is hydrogen, 1-4C-alkyl, hydroxy-2-4C-alkyl or 1-4C-alkoxy-2-4C-alkyl, 
         or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which 
         Het1 is a fully saturated or partially unsaturated mono- or fused bicyclic ring or ring system made up of
 a first constituent being a 3- to 7-membered monocyclic fully saturated non-aromatic heterocyclic ring B,
 which heterocyclic ring B comprises one to three heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, 
 and which heterocyclic ring B is optionally substituted by one or two oxo groups, 
 
 and, optionally, fused to said first constituent, 
 
         a second constituent being a benzene ring, 
         and which ring Het1 is optionally substituted by R23 on a ring carbon atom, 
         and/or which ring Het1 is optionally substituted by R24 on a further ring carbon atom, 
         and/or which ring Het1 is optionally substituted by an ethylenedioxy group on a ring carbon atom, 
         and/or which ring Het1 is optionally substituted by R25 on a ring nitrogen atom, 
         in which 
         R23 is 1-4C-alkyl, 1-4C-alkoxy or phenylcarbonyl, 
         R24 is 1-4C-alkyl or 1-4C-alkoxy, 
         R25 is 1-4C-alkyl, phenyl-1-4C-alkyl, 1-4C-alkylcarbonyl, 1-4C-alkoxy-2-4C-alkyl, mono- or di-1-4C-alkylamino-2-4C-alkyl, phenyl, pyrimidyl, pyridyl, formyl, 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl, or R251- and/or R252-substituted phenyl, in which 
         R251 is halogen, cyano or 1-4C-alkyl, 
         R252 is halogen or 1-4C-alkyl, 
         R3 is hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, 1-4C-alkoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy, 
         Har1 is bonded to the parent molecular group via a ring carbon atom, and is a monocyclic or fused bicyclic 5- to 10-membered unsaturated or partially saturated heteroaryl radical comprising one to three heteroatoms, each of which is selected from the group consisting of nitrogen, oxygen and sulfur, 
         R4 is 1-4C-alkyl, halogen, cyano, trifluoromethyl, phenyl, mono- or di-1-4C-alkylamino, formyl, 1-4C-alkylcarbonyl, carboxyl or 1-4C-alkoxy, 
         R5 is 1-4C-alkyl or halogen, 
       
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof, wherein the chronic inflammatory disease of a peripheral organ or central nervous system is selected from the group consisting of COPD, asthma, allergic rhinitis, rheumatoid arthritis, osteoarthritis, neuropathic pain, psoriasis, dermatitis, Crohn's disease and ulcerative colitis. 
     
     
         26 . The method according to  claim 25   in which   A is 1-4C-alkylene or 3-7C-cycloalkylene,   R1 is phenyl, R2- and/or R3-substituted phenyl, Har1, or R4- and/or R5-substituted Har1,   R11 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy,   in which   R2 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, 1-4C-alkylsulfonylamino, phenylsulfonylamino, phenyl-1-4C-alkoxy, or —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, phenyl-1-4C-alkyl, Har2-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl, pyridyl, or R211- and/or R212-substituted phenyl, in which   Har2 is pyridyl, thienyl or furyl,   R211 is 1-4C-alkyl, halogen, 1-4C-alkoxy, or mono- or di-1-4C-alkylamino,   R212 is 1-4C-alkyl or halogen,   R22 is hydrogen, 1-4C-alkyl, hydroxy-2-4C-alkyl or 1-4C-alkoxy-2-4C-alkyl,   or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is a fully saturated or partially unsaturated mono- or fused bicyclic ring or ring system made up of
 a first constituent being a 3- to 7-membered monocyclic fully saturated non-aromatic heterocyclic ring B,
 which heterocyclic ring B comprises one to three heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, 
 and which heterocyclic ring B is optionally substituted by one or two oxo groups, 
 
 and, optionally, fused to said first constituent, 
   a second constituent being a benzene ring,   and which ring Het1 is optionally substituted by R23 on a ring carbon atom,   and/or which ring Het1 is optionally substituted by R24 on a further ring carbon atom,   and/or which ring Het1 is optionally substituted by an ethylenedioxy group on a ring carbon atom,   and/or which ring Het1 is optionally substituted by R25 on a ring nitrogen atom,   in which   R23 is 1-4C-alkyl, 1-4C-alkoxy or phenylcarbonyl,   R24 is 1-4C-alkyl or 1-4C-alkoxy,   R25 is 1-4C-alkyl, phenyl-1-4C-alkyl, 1-4C-alkylcarbonyl, 1-4C-alkoxy-2-4C-alkyl, mono- or di-1-4C-alkylamino-2-4C-alkyl, phenyl, pyrimidyl, pyridyl, formyl, 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl, or R251- and/or R252-substituted phenyl, in which   R251 is halogen, cyano or 1-4C-alkyl,   R252 is halogen or 1-4C-alkyl,   R3 is hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, 1-4C-alkoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy,   Har1 is bonded to the parent molecular group via a ring carbon atom, and is a monocyclic or fused bicyclic 5- to 10-membered unsaturated or partially saturated heteroaryl radical comprising one to three heteroatoms, each of which is selected from the group consisting of nitrogen, oxygen and sulfur,   R4 is 1-4C-alkyl, halogen, cyano, trifluoromethyl, phenyl, mono- or di-1-4C-alkylamino, formyl, 1-4C-alkylcarbonyl, carboxyl or 1-4C-alkoxy,   R5 is 1-4C-alkyl or halogen,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         27 . The method according to  claim 25   in which   A is ethylene or cyclopropylene,   R1 is bonded to the 6-position of the imidazopyridine scaffold, and is phenyl, R2- and/or R3-substituted phenyl, or Hart   R11 is hydrogen,   in which   R2 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, 1-4C-alkylsulfonylamino, phenylsulfonylamino, phenyl-1-4C-alkoxy, or —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, phenyl-1-4C-alkyl, Har2-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl, pyridyl, or R211- and/or R212-substituted phenyl, in which   Har2 is pyridyl, thienyl or furyl,   R211 is 1-4C-alkyl, halogen, 1-4C-alkoxy, or mono- or di-1-4C-alkylamino,   R212 is 1-4C-alkyl or halogen,   R22 is hydrogen, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl or 1-4C-alkyl,   or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is piperidinyl, pyrrolidinyl, azetidinyl, morpholinyl, thiomorpholinyl, S-oxo-thiomorpholinyl or S,S-dioxo-thiomorpholinyl, indolinyl, isoindolinyl, 1,2,3,4-tetrahydroquinolinyl, 1,2,3,4-tetrahydroisoquinolinyl, piperazinyl, homopiperazinyl, 4N—(R25)-piperazinyl, 4N—(R25)-homopiperazinyl, 2-oxopyrrolidinyl, 2-oxoimidazolidinyl, 2-oxopiperidinyl, 2,5-dioxopyrrolidinyl, 2,5-dioxoimidazolidinyl, 2,6-dioxopiperidinyl, 2-oxopiperazinyl, 2,6-dioxopiperazinyl, 5-oxo-1,4-diazepanyl, 3-(R25)-imidazolidin-2-one-yl, 3-(R25)-imidazolidin-2,5-dione-yl, 4-(R25)-piperazine-2-one-yl, 4-(R25)-piperazine-2,6-dione-yl or 4-(R25)-1,4-diazepan-5-one-yl, in which   R25 is 1-4C-alkyl, phenyl-1-4C-alkyl, 1-4C-alkylcarbonyl, 1-4C-alkoxy-2-4C-alkyl, mono- or di-1-4C-alkylamino-2-4C-alkyl, phenyl, pyrimidyl, pyridyl, formyl, 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl, or R251- and/or R252-substituted phenyl, in which   R251 is halogen, cyano or 1-4C-alkyl,   R252 is halogen or 1-4C-alkyl,   R3 is hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, 1-4C-alkoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy,   Har1 is bonded to the parent molecular group via a ring carbon atom, and is pyridyl, thienyl, furanyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzothiazolyl, quinolyl or isoquinolyl,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         28 . The method according to  claim 25   in which   A is ethylene,   R1 is bonded to the 6-position of the imidazopyridine scaffold, and is phenyl, or R2- and/or R3-substituted phenyl,   R11 is hydrogen,   in which   R2 is cyano, halogen, carboxyl, 1-4C-alkyl, 1-4C-alkoxy, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkoxycarbonyl, amino, mono- or di-1-4C-alkylamino, trifluoromethyl, hydroxyl, 1-4C-alkylsulfonylamino, phenylsulfonylamino, or phenyl-1-4C-alkoxy,   R3 is hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, 1-4C-alkoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         29 . The method according to  claim 25   in which   A is ethylene,   R1 is bonded to the 6-position of the imidazopyridine scaffold, and is R2- and/or R3-substituted phenyl or Har1,   R11 is hydrogen,   in which   R2 is —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, phenyl-1-4C-alkyl, Har2-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl, phenyl, pyridyl, or R211- and/or R212-substituted phenyl, in which   Har2 is pyridyl, thienyl or furyl,   R211 is 1-4C-alkyl, halogen, 1-4C-alkoxy, or mono- or di-1-4C-alkylamino,   R212 is 1-4C-alkyl or halogen,   R22 is hydrogen, hydroxy-2-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl or 1-4C-alkyl,   or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is piperidinyl, pyrrolidinyl, azetidinyl, morpholinyl, thiomorpholinyl, S-oxo-thiomorpholinyl or S,S-dioxo-thiomorpholinyl, indolinyl, isoindolinyl, 1,2,3,4-tetrahydroquinolinyl, 1,2,3,4-tetrahydroisoquinolinyl, piperazinyl, homopiperazinyl, 4N—(R25)-piperazinyl, 4N—(R25)-homopiperazinyl, 2-oxopyrrolidinyl, 2-oxoimidazolidinyl, 2-oxopiperidinyl, 2,5-dioxopyrrolidinyl, 2,5-dioxoimidazolidinyl, 2,6-dioxopiperidinyl, 2-oxopiperazinyl, 2,6-dioxopiperazinyl, 5-oxo-1,4-diazepanyl, 3-(R25)-imidazolidin-2-one-yl, 3-(R25)-imidazolidin-2,5-dione-yl, 4-(R25)-piperazine-2-one-yl, 4-(R25)-piperazine-2,6-dione-yl or 4-(R25)-1,4-diazepan-5-one-yl, in which   R25 is 1-4C-alkyl, phenyl-1-4C-alkyl, 1-4C-alkylcarbonyl, 1-4C-alkoxy-2-4C-alkyl, mono- or di-1-4C-alkylamino-2-4C-alkyl, phenyl, pyrimidyl, pyridyl, formyl, 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl, or R251- and/or R252-substituted phenyl, in which   R251 is halogen, cyano or 1-4C-alkyl,   R252 is halogen or 1-4C-alkyl,   R3 is hydrogen, 1-4C-alkyl, halogen, trifluoromethyl, 1-4C-alkoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy,   Har1 is bonded to the parent molecular group via a ring carbon atom, and is pyridyl, thienyl, furanyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzothiazolyl, quinolyl or isoquinolyl,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         30 . The method according to  claim 25   in which   A is 1-4C-alkylene,   R1 is phenyl, R2-substituted phenyl or Hart   R11 is hydrogen,   in which   R2 is cyano, 1-4C-alkoxy or —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, Har2-1-4C-alkyl, phenyl or R211- and/or R212-substituted phenyl,   in which   Har2 is furyl or tetrahydrofuranyl,   R211 is 1-4C-alkyl or halogen,   R212 is 1-4C-alkyl or halogen,   R22 is hydrogen or 1-4C-alkyl,   or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is a 3- to 7-membered monocyclic fully saturated non-aromatic heterocyclic ring B, which heterocyclic ring B comprises one to three heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur,   and which ring Het1 is optionally substituted by R23 on a ring carbon atom,   and/or which ring Het1 is optionally substituted by R25 on a ring nitrogen atom,   in which   R23 is 1-4C-alkyl,   R25 is 1-4C-alkyl,   Har1 is bonded to the parent molecular group via a ring carbon atom, and is a monocyclic or fused bicyclic 5- to 10-membered unsaturated heteroaryl radical comprising one to three heteroatoms, each of which is selected from the group consisting of nitrogen, oxygen and sulfur,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         31 . The method according to  claim 25   in which   A is ethylene,   R1 is phenyl, R2-substituted phenyl or Hart   R11 is hydrogen,   in which   R2 is cyano, 1-4C-alkoxy or —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, Har2-1-4C-alkyl or R211- and/or R212-substituted phenyl, in which   Har2 is tetrahydrofuranyl,   R211 is 1-4C-alkyl or halogen,   R212 is 1-4C-alkyl,   R22 is hydrogen or 1-4C-alkyl, or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is a 4- to 6-membered monocyclic fully saturated non-aromatic heterocyclic ring B, which heterocyclic ring B comprises one to three nitrogen atoms,   
       and which ring Het1 is optionally substituted by R25 on a ring nitrogen atom,
 in which 
 R25 is 1-4C-alkyl, 
 Har1 is bonded to the parent molecular group via a ring carbon atom, and is a fused bicyclic 9-membered unsaturated heteroaryl radical comprising one oxygen atom, 
 
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         32 . The method according to  claim 25   in which   A is ethylene,   R1 is phenyl, R2-substituted phenyl or Hart   R11 is hydrogen,   in which   R2 is cyano, 1-4C-alkoxy or —SO 2 —N(R21)R22, in which   R21 is hydrogen, 1-4C-alkyl, Har2-1-4C-alkyl or R211- and/or R212-substituted phenyl, in which   Har2 is tetrahydrofuranyl,   R211 is 1-4C-alkyl or halogen,   R212 is 1-4C-alkyl,   R22 is hydrogen or 1-4C-alkyl,   or R21 and R22 together and with inclusion of the nitrogen atom, to which they are bonded, form a heterocyclic ring Het1, in which   Het1 is an azetidinyl or piperazinyl ring, which ring Het1 is optionally substituted by R25 on a ring nitrogen atom, in which   R25 is 1-4C-alkyl,   Har1 is bonded to the parent molecular group via a ring carbon atom, and is a benzofuranyl ring,   
       or a pharmaceutically acceptable enantiomer, salt, or salt of an enantiomer thereof. 
     
     
         33 . The method according to  claim 25 , wherein the compound is selected from the group consisting of 7-[2-(6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 7-[2-(6-{4-cyano-phen-1-yl}-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 7-{2-[6-(4-methoxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 7-[2-(6-benzofuran-2-yl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 4-{2-[2-(7-amino-3,4,5,6-tetrahydro-2H-azepin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N,N-dimethyl-benzenesulfonamide, 7-(2-{6-[4-(azetidine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 7-(2-{6-[4-(4-ethyl-piperazine-1-sulfonyl)-phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}-ethyl)-4,5,6,7-tetrahydro-3H-azepin-2-ylamine, 4-{2-[2-(7-amino-3,4,5,6-tetrahydro-2H-azepin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N-(2-fluoro-4-methyl-phenyl)-benzenesulfonamide, 4-{2-[2-(7-amino-3,4,5,6-tetrahydro-2H-azepin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N-o-tolyl-benzenesulfonamide and 4-{2-[2-(7-amino-3,4,5,6-tetrahydro-2H-azepin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-N-methyl-N-(tetrahydro-furan-2-ylmethyl)-benzenesulfonamide.