Imidazopyrimidine derivatives and triazolopyrimidine derivatives

1. A compound of the formula:

wherein

R 1 represents —OR 11 , —SR 11 , —SOR 11 , —SO 2 R 11 , —NHR 11 , or —NR 12 R 13 ,

R 11 represents H, phenyl carbonyl, thienyl optionally substituted by COOR 111 (R 111 is H or C 1 -C 6 alkyl), pyrimidyl, C 2 -C 6 alkenyl, imidazolyl optionally substituted by C 1 -C 6 alkyl, triazolyl optionally substituted by C 1 -C 6 alkyl, tetrazolyl optionally substituted by C 1 -C 6 alkyl, thiadiazolyl optionally substituted by C 1 -C 6 alkyl, pyrrolidinyl optionally substituted by C 1 -C 6 alkyl, cyclohexenyl, C 1 -C 10 straight- or branched-alkyl optionally substituted by R 112 , R 113 and/or R 114 , C 3 -C 10 cyclo-alkyl optionally substituted by R 112 , R 113 and/or R 114 , phenyl optionally substituted by R 115 , R 116 , and/or R 117 , pyridyl optionally substituted by R 115 , R 116 , and/or R 117 , or 9-10-membered unsaturated condensed ring which optionally contains up to 3 hetero atoms selected from the group consisting of N, O and S and optionally substitued by R 118 ,

R 112 represents halogen, amino, —COOR 112a (R 112a represents H or C 1 -C 6 alkyl) —CO—NH—CH 3 , —CO—NH—(CH 2 ) p CN (p=0, 1, 2, 3, 4, 5, or 6), —NH—COOR 112a , pyrazinyl, tetrazolyl, dihydrothiophenyl, morpholino, piperidino, di(C 1 -C 6 alkyl)amino, indolyl, pyridinyl, thiophenyl, or phenyl optionally substituted by one to three substituents selected from the group consisting of halogen, C 1 -C 6 alkyl, hydroxy, C 1 -C 6 alkoxy, and trihalogen substituted C 1 -C 6 alkyl,

R 113 represents halogen, hydroxy, or C 1 -C 6 alkoxy-carbonyl,

R 114 represents halogen,

R 115 represents H, halogen, amino, hydroxy, nitro, cyano, C 1 -C 6 alkoxy, carboxy, C 1 -C 6 alkoxy carbonyl, C 1 -C 6 alkyl carbonyl, morpholino-C 1 -C 6 alkyl-oxy, caroboxy-C 1 -C 6 alkyl-oxy, trihalogen substituted methyl, trihalogen substituted methoxy, C 1 -C 10 straight- or branched-alkyl optionally substituted by R 115a , C 3 -C 10 cyclo-alkyl optionally substituted by R 115a , tetrazolyl, amidino, —CON(R 115b )R 115c , —SO 2 N(R 115b )R 115c , —N(R 115b )R 115c , —SO 2 R 115d , —SOR 115d , —SR 115d , or C 2 -C 6 alkenyl optionally substituted by COOR 115e

R 115a represents one or two selected from the group consisting of carboxy, morpholino, morpholino-carbonyl, amino, hydroxy, cyano, C 1 -C 6 alkoxy carbonyl, carbamoyl optionally substituted by cyano-C 1 -C 6 alkyl, methylamino-carbonyl, dimethylamino-carbonyl, —NH—SO 2 —CH 3 , tetrazolyl, dihydrooxazolyl optionally substituted by C 1 -C 6 alkyl, and 9-10 membered unsaturated condensed ring containing one N atom optionally substituted by ═O,

R 115b represents H or C 1 -C 6 alkyl,

R 115c represents H, amino, C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, amidino, morpholino-C 1 -C 6 alkyl carbonyl, carboxy-C 1 -C 6 alkyl carbonyl, or straight- or branched C 1 -C 6 alkyl optionally substituted by one or two selected from the group consisting of hydroxy, phenyl, morpholino, di(C 1 -C 6 alkyl) amino, C 1 -C 6 alkyl and hydroxy C 1 -C 6 alkyl substituted amino, C 1 -C 6 alkoxy-carbonyl, and carboxy,

or R 115b and R 115c together with the adjacent N form 5 or 6 membered saturated hetero cyclic ring optionally having one N or O atom other than the adjacent N and optionally substituted by C 1 -C 6 alkyl,

R 115d represents hydroxy, hydroxy C 1 -C 6 alkyl, C 1 -C 6 alkyl, hydroxy-carbonyl-C 1 -C 6 alkyl, or C 1 -C 6 alkoxy carbonyl C 1 -C 6 alkyl,

R 115e represents hydrogen or C 1 -C 6 alkyl,

R 116 represents H, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, halogen, or carbamoyl,

R 117 represents H, halogen, or C 1 -C 6 alkoxy,

R 118 represents one to three substituents selected from the group consisting of C 1 -C 6 alkyl, amino, C 1 -C 6 alkoxy, —COOR 118a (R 118a is H or C 1 -C 6 alkyl), and ═O,

R 12 represents C 1 -C 6 alkyl, —(CH 2 ) q —OH, —(CH 2 ) q —CN (q=0, 1, 2, 3, 4, 5, or 6), —CO—C 1 -C 6 alkyl), or —C 2 -C 6 alkenyl,

R 13 is identical to R 11 ,

or R 12 and R 13 together with the adjacent N atom form 4-6 membered saturated heterocyclic ring which may or may not contain 1 heteroatom other than the adjacent N atom selected from the group consisting of O, N, and S

the 4-6 membered heterocyclic ring optionally form spiro with dioxacyclopentane, or

is optionally fused with benzene, and/or

is optionally substituted by one or two substituents selected from the group consisting of C 1 -C 6 alkyl carbonyl, C 1 -C 6 alkyl, hydroxy, hydroxy C 1 -C 6 alkyl, carboxyl, C 1 -C 6 alkoxy carbonyl, carbamoyl, phenyl, halogen substituted phenyl, C 1 -C 6 alkoxy substituted phenyl, C 1 -C 6 alkyl substituted phenyl, nitro phenyl, hydroxy phenyl, C 1 -C 6 alkyl carbonyl phenyl, C 1 -C 6 alkoxy carbonyl phenyl, pyridyl optionally substituted by CF 3 , pyrimidyl, C 3-7 cycloalkyl, dioxolanyl, piperidino, halogen substituted phenyl carbonyl, furyl carbonyl, cyano, dimethylamino, benzyl, oxo residue, piperonyl methyl, halogen substituted diphenyl methyl, and trifluorocarbonyl amino,

Y is CH or N;

R 2 is H, C 1 -C 6 alkyl, carbamoyl, or —COOR 21 ,

wherein R 21 is H or C 1 -C 6 alkyl;

R 3 is thienyl, pyridyl optionally substituted by halogen or C 1 -C 6 alkoxy, naphthyl optionally substituted by C 1 -C 6 alkoxy, dioxane fused phenyl, dioxacyclopentane fused phenyl, or phenyl optionally substituted by one to three substituents selected from the group consisting of halogen, C 1 -C 6 alkyl, nitro, amino, hydroxy, C 1 -C 6 alkylthio, —OR 31 , —OR 32 , —NR 33 R 34 , and —SO 2 R 35 ,

wherein R 31 and R 32 are identical or different and represent C 1 -C 6 alkyl carbonyl, C 1 -C 6 alkoxy carbonyl, C 2 -C 6 alkenyl, di(C 1 -C 6 alkyl) amino carbonyl, C 1 -C 6 alkyl amino carbonyl, —SO 2 -R 311 , straight- or branched-C 1 -C 6 alkyl optionally substituted by R 312 , or cyclo-C 3 -C 7 alkyl optionally substituted by R 312 ,

R 311 represents C 1 -C 6 alkyl, amino, di(C 1 -C 6 alkyl) amino C 1 -C 6 alkyl amino, C 1 -C 6 alkoxy carbonyl C 1 -C 6 alkyl amino, or 5-6 membered saturated hetero ring containing up to 2 heteroatoms of N, S, and/or O and optionally substituted by C 1 -C 6 alkyl or carboxy,

R 312 represents C 1 -C 6 alkoxy, halogen, phenyl optionally substituted by C 1 -C 6 alkoxy, di(C 1 -C 6 alkyl) amino, C 1 -C 6 alkyl and hydroxy C 1 -C 6 alkyl substituted amino, or 5-6 membered saturated hetero cyclic ring containing up to 2 heteroatoms of N, S, and/or O and optionally substituted by one or three substituents selected from the group consisting of C 1 -C 6 alkyl, carbamoyl, and di(C 1 -C 6 alkyl)amino,

R 33 represents H or C 1 -C 6 alkyl,

R 34 represents carboxy C 1 -C 6 alkyl carbonyl, C 1 -C 6 alkyl carbonyl, or C 1 -C 6 alkyl optionally substituted by R 341 ,

wherein R 341 represents dimethylamino, C 1 -C 6 alkoxyl, morpholino, phenyl, C 1 -C 6 alkyl substituted piperazino, oxopyrrolidino, or imidazolyl,

or —N R 33 R 34 forms 5-6-membered saturated hetero cyclic ring optionally containing one more hetero atom selected from the group consisting of N, S, and O and optionally substituted by C 1 -C 6 alkyl,

R 35 represents amino, di(C 1 -C 6 alkyl)amino C 1 -C 6 alkyl amino, piperazino optionally substituted by hydroxy C 1 -C 6 alkyl or C 1 -C 6 alkyl, C 1 -C 6 alkoxy carbonyl C 1 -C 6 alkyl amino, morpholino, piperidino optionally substituted by carboxy or C 1 -C 6 alkyl, or hydroxy C 1 -C 6 alkyl amino,

or its tautomeric or stereoisomeric form, or its physiologically acceptable salt.

2. The compound as claimed in claim 1 , wherein R 1 represents —OR 11 , —SR 11 , —NHR 11 , or —NR 12 R 13

R 11 represents H, phenyl carbonyl, thienyl optionally substituted by COOR 111 (R 111 is H or C 1 -C 6 alkyl), pyrimidyl, C 2 -C 6 alkenyl, imidazolyl optionally substituted by C 1 -C 6 alkyl, triazolyl optionally substituted by C 1 -C 6 alkyl, tetrazolyl optionally substituted by C 1 -C 6 alkyl, thiadiazolyl optionally substituted by C 1 -C 6 alkyl, pyrrolidinyl optionally substituted by C 1 -C 6 alkyl, cyclohexenyl, C 1 -C 10 straight- or branched-alkyl optionally substituted by R 112 , R 113 and/or R 114 , C 3 -C 10 cyclo-alkyl optionally substituted by R 112 , R 113 and/or R 114 , phenyl optionally substituted by R 115 , R 116 , and/or R 117 , pyridyl optionally substituted by R 115 , R 116 , and/or R 117 , or 9-10-membered unsaturated condensed ring which optionally contains up to 3 hetero atoms selected from the group consisting of N and S and optionally substituted by R 118 ,

R 112 represents halogen, amino, —COOR 112a (R 112a represents H or C 1 -C 6 alkyl), —CO—NH—CH 3 , —CO—NH—(CH 2 ) p CN, —NH—COOR 112a , pyrazinyl, tetrazolyl, dihydrothiophenyl, morpholino, piperidino, di(C 1 -C 6 alkyl)amino, indolyl, pyridinyl, thiophenyl, or phenyl optionally substituted by one substituent selected from the group consisiting of halogen, hydroxy, C 1 -C 6 alkoxy, and trihalogen substituted methyl,

R 113 represents halogen, hydroxy, or C 1 -C 6 alkoxy-carbonyl,

R 114 represents halogen,

R 115 represents H, halogen, amino, hydroxy, nitro, cyano, carboxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 alkyl carbonyl, morpholino-C 1 -C 6 alkyl-oxy, carboxy-C 1 -C 6 alkyl-oxy, trihalogen substituted methyl, trihalogen substituted methoxy, C 1 -C 10 straight- or branched-alkyl optionally substituted by R 115a , C 3 -C 10 cyclo-alkyl optionally substituted by R 115a , tetrazolyl, amidino, —CON(R 115b )R 115c , —SO 2 N(R 115b )R 115c , —N(R 115b )R 115c , —SO 2 R 115d , —SOR 115d , —SR 115d , or C 2 -C 6 alkenyl optionally substituted by COOR 115e ,

R 115a represents one or two selected from the group consisting of carboxy, morpholino, morpholino-carbonyl, amino, hydroxy, cyano, C 1 -C 6 alkoxy carbonyl, carbamoyl optionally substituted by cyano-C 1 -C 6 alkyl, methylamino-carbonyl, dimethylamino-carbonyl, —NH—SO 2 —CH 3 , tetrazolyl, dihydrooxazolyl optionally substituted by C 1 -C 6 alkyl, and 9-10 membered unsaturated condensed ring containing one N atom optionally substituted by ═O,

R 115b represents H or C 1 -C 6 alkyl,

R 115c represents H, amino, C 1 -C 6 alkyl amino, di(C 1 -C 6 alkyl)amino, amidino, morpholino-C 1 -C 6 alkyl carbonyl, carboxy-C 1 -C 6 alkyl carbonyl, or straight- or branched C 1 -C 6 alkyl optionally substituted by one or two selected from the group consisting of hydroxy, phenyl, morpholino, di(C 1 -C 6 alkyl) amino, C 1 -C 6 alkyl and hydroxy C 1 -C 6 alkyl substituted amino, C 1 -C 6 alkoxy-carbonyl, and carboxy,

or R 115b and R 115c together with the adjacent N form 5 or 6 membered saturated hetero ring optionally having one N or O atoms other than the adjacent N and optionally substituted by C 1 -C 6 alkyl,

R 115d represents hydroxy, hydroxy C 1 -C 6 alkyl, C 1 -C 6 alkyl, hydroxy-carbonyl-C 1 -C 6 alkyl, or C 1 -C 6 alkoxy carbonyl C 1 -C 6 alkyl,

R 115e represents hydrogen or C 1 -C 6 alkyl,

R 116 represents H, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, halogen, or carbamoyl,

R 117 represents H, halogen, or C 1 -C 6 alkoxy,

R 118 represents one to three substituents selected from the group consisting of C 1 -C 6 alkyl, amino, C 1 -C 6 alkoxy, COOR 118a (H or C 1 -C 6 alkyl), and ═O

R 12 represents C 1 -C 6 alkyl, —(CH 2 ) q —OH, —(CH 2 ) q —CN (q=0, 1, 2, 3, 4, 5, or 6), —CO—C 1 -C 6 alkyl), or —C 2 -C 6 alkenyl (—CH 2 —CH═CH 2 ),

R 13 is identical to R 11 ,

or R 12 and R 13 together with the adjacent N atom form 4-6 membered saturated heterocyclic ring which may or may not contain 1 heteroatom other than the adjacent N atom selected from the group consisting of O, N, and S,

the 4-6 membered heterocyclic ring optionally form spiro with dioxacyclopentane, or

is optionally fused with benzene, and/or

is optionally substituted by one or two substituents selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 alkyl carbonyl, hydroxy, hydroxy C 1 -C 6 alkyl, carboxyl, C 1 -C 6 alkoxy carbonyl, carbamoyl, phenyl, halogen substituted phenyl, C 1 -C 6 alkoxy substituted phenyl, C 1 -C 6 alkyl substituted phenyl, nitro phenyl, hydroxy phenyl, C 1 -C 6 alkyl carbonyl phenyl, C 1 -C 6 alkoxy carbonyl phenyl, pyridyl optionally substituted by CF 3 , pyrimidyl, C 3-7 cycloalkyl, dioxolanyl, piperidino, halogen substituted phenyl carbonyl, furyl carbonyl, cyano, dimethylamino, benzyl, oxo residue, piperonyl methyl, halogen substituted diphenyl methyl, and trifluorocarbonyl amino,

Y is CH or N;

R 2 is H C 1 -C 6 alkyl, or carbamoyl;

R 3 is thienyl, pyridyl optionally substituted by halogen or C 1 -C 6 alkoxy, dioxane fused phenyl, dioxacyclopentane fused phenyl, or phenyl optionally substituted by one to three substituents selected from the group consisting of halogen, C 1 -C 6 alkyl, nitro, amino, hydroxy, C 1 -C 6 alkylthio, —OR 31 , —OR 32 , —NR 33 R 34 , and —SO 2 R 35 ,

wherein R 31 and R 32 are identical or different and represent nitro, C 1 -C 6 alkyl carbonyl, C 1 -C 6 alkoxy carbonyl, C 2 -C 6 alkenyl, di(C 1 -C 6 alkyl) amino carbonyl, C 1 -C 6 alkyl amino carbonyl, —SO 2 —R 311 , straight- or branched-C 1 -C 6 alkyl optionally substituted by R 312 , or cyclo-C 3 -C 7 alkyl optionally substituted by R 312 ,

R 311 represents C 1 -C 6 alkyl, amino, di(C 1 -C 6 alkyl) amino C 1 -C 6 alkyl amino, C 1 -C 6 alkoxy carbonyl C 1 -C 6 alkyl amino, 5-6 membered saturated hetero ring containing up to 2 heteroatoms of N, S, and/or O and optionally substituted by C 1 -C 6 alkyl or carboxy,

R 312 represents one selected from the group consisting of C 1 -C 6 alkoxy, halogen, phenyl optionally substituted by C 1 -C 6 alkoxy, di(C 1 -C 6 alkyl) amino, C 1 -C 6 alkyl and hydroxy C 1 -C 6 alkyl substituted amino, or 5-6 membered saturated hetero cyclic ring containing up to 2 heteroatoms of N, S, and/or O and optionally substituted by C 1 -C 6 alkyl, carbamoyl, or di(C 1 -C 6 alkyl)amino,

R 33 represents H or C 1 -C 6 alkyl,

R 34 represents carboxy C 1 -C 6 alkyl carbonyl, C 1 -C 6 alkyl carbonyl, or C 1 -C 6 alkyl optionally substituted by R 341 ,

wherein R 341 represents dimethylamino, C 1 -C 6 alkoxyl, morpholino, phenyl, C 1 -C 6 alkyl substituted piperazino, oxopyrrolidino, or imidazolyl, or —N R 33 R 34 form morpholino optionally substituted by C 1 -C 6 alkyl, thiazinano optionally substituted by C 1 -C 6 alkyl, piperidino optionally substituted by C 1 -C 6 alkyl, or pyrrolidino optionally substituted by C 1 -C 6 alkyl,

R 35 represents amino, di(C 1 -C 6 alkyl)amino C 1 -C 6 alkyl amino, hydroxy C 1 -C 6 alkyl amino, C 1 -C 6 alkoxy carbonyl C 1 -C 6 alkyl amino, morpholino, piperazino optionally substituted by hydroxy C 1 -C 6 alkyl or C 1 -C 6 alkyl, or piperidino optionally substituted by carboxy,

or its tautomeric or stereoisomeric form, or its physiologically acceptable salt.

3. The compound as claimed in claim 1 , wherein R 1 represents —OR 11 , —SR 11 , or —NHR 11

R 11 represents phenyl optionally substituted by R 115 , R 116 , and/or R 117 , pyridyl optionally substituted by R 115 , R 116 , and/or R 117 , or 9-10-membered unsaturated condensed ring which optionally contains up to 3 N atoms and optionally substitued by R 118

R 115 represents H, halogen, amino, hydroxy, nitro, cyano, carboxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 alkyl carbonyl, morpholino-C 1 -C 6 alkyl-oxy, carboxy-C 1 -C 6 alkyl-oxy, trihalogen substituted methyl, trihalogen substituted methoxy, C 1 -C 10 straight- or branched-alkyl optionally substituted by R 115a , C 3 -C 10 cyclo-alkyl optionally substituted by R 115a , tetrazolyl, amidino, —CON(R 115b )R 115c , —SO 2 N(R 115b )R 115c , —N(R 115b )R 115c , —SO 2 R 115d , —SOR 115d , —SR 115d , or C 2 -C 6 alkenyl optionally substituted by COOR 115e ,

R 115a represents one or two selected from the group consisting of morpholino, morpholino-carbonyl, amino, hydroxy, cyano, C 1 -C 6 alkoxy carbonyl, carbamoyl, methylamino-carbonyl, dimethylamino-carbonyl, —NH—SO 2 —CH 3 , dihydrooxazolyl optionally substituted by C 1 -C 6 alkyl, and 9-10 membered unsaturated condensed ring containing one N atom optionally substituted by ═O,

R 115b represents H or C 1 -C 6 alkyl,

R 115c represents H, amino, amidino, morpholino-C 1 -C 6 alkyl carbonyl, carboxy-C 1 -C 6 alkyl carbonyl, or straight- or branched C 1 -C 6 alkyl optionally substituted by one or two selected from the group consisting of hydroxy, phenyl, morpholino, di(C 1 -C 6 alkyl) amino, C 1 -C 6 alkyl and hydroxy C 1 -C 6 alkyl substituted amino, C 1 -C 6 alkoxy-carbonyl, and carboxy,

or R 115b and R 115c together with the adjacent N form 5 or 6 membered saturated hetero cyclic ring optionally having one N or O atoms other than the adjacent N and optionally substituted by C 1 -C 6 alkyl,

R 115d represents C 1 -C 6 alkyl, hydroxy, hydroxy C 1 -C 6 alkyl, hydroxy-carbonyl-C 1 -C 6 alkyl, or C 1 -C 6 alkoxy carbonyl C 1 -C 6 alkyl,

R 115e represents hydrogen or C 1 -C 6 alkyl

R 116 represents H, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, halogen, or carbamoyl,

R 117 represents H, halogen, or C 1 -C 6 alkoxy

R 118 represents C 1 -C 6 alkyl, amino, C 1 -C 6 alkoxy, COOR 118a (R 118a is H or C 1 -C 6 alkyl), or ═O (mono or di),

Y is CH or N;

R 2 is H;

R 3 is phenyl optionally substituted by two substituents selected from the group consisting of —OR 31 , —OR 32 , and —NR 33 R 34 ,

wherein R 31 and R 32 are identical or different and represent straight- or branched-C 1 -C 6 alkyl optionally substituted by R 312 , cyclo-C 3 -C 7 alkyl optionally substituted by R 312 ,

R 312 represents one selected from the group consisting of C 1 -C 6 alkoxy, halogen, phenyl optionally substituted by C 1 -C 6 alkoxy, di(C 1 -C 6 alkyl) amino, C 1 -C 6 alkyl and hydroxy C 1 -C 6 alkyl substituted amino, or 5-6 membered saturated hetero cyclic ring containing up to 2 heteroatoms of N, S, and/or O and optionally substituted by C 1 -C 6 alkyl, carbamoyl, or di(C 1 -C 6 alkyl)amino,

R 33 represents H, or C 1 -C 6 alkyl,

R 34 represents C 1 -C 6 alkyl optionally substituted by C 1 -C 6 alkoxyl,

or —N R 33 R 34 forms morpholino optionally substituted by C 1 -C 6 alkyl,

or its tautomeric or stereoisomeric form, or its physiologically acceptable salt.

4. The compound as claimed in claim 1 selected from the group consisting of the following compounds:

[7-(3,4-Dimethoxy-phenyl)-imidazo[1,2-c]pyrimidin-5-yl]-(1H-indazol-6-yl)-amine;

2-[7-(3,4-Dimethoxy-phenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]-benzamide;

2-[7-(3,4-Dimethoxy-phenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]-5-methoxy-benzamide;

2-[7-(3,4-Dimethoxy-phenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]-benzenesulfonamide;

[7-(3,4-Dimethoxy-phenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-yl]-(1H-indazol-6-yl)-amide;

4-Amino-2-[7-(3,4-dimethoxy-phenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]-benzamide;

(7-(3-methoxy-4-[(2-methoxy-ethyl)-methyl-amino]-phenyl)-imidazo[1,2-c]pyrimidin-5-yl)-(4-methoxy-phenyl)-amine;

[7-(3-Methoxy-4-morpholin-4-yl-phenyl)-imidazo[1,2-c]pyrimidin-5-yl]-p-tolyl-amine;

(2-Methanesulfonyl-phenyl)-(7-(3-methoxy-4-[(2-methoxy-ethyl)-methyl-amino]-phenyl)-imidazo[1,2-c]pyrimidin-5-yl)-amine;

2-[7-(3-Methoxy-4-morpholin-4-yl-phenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]-nicotinamide;

2-[7-(3-Methoxy-4-morpholin-4-yl-phenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]-benzamide;

2-Methanesulfonyl-phenyl)-[7-(3-methoxy-4-morpholin-4-yl-phenyl)-imidazo[1,2-c]pyrimidin-5-yl]-amine;

4-[7-(3-Methoxy-4-morpholin-4-yl-phenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]-phenol;

[7-(3-Methoxy-4-morpholin-4-yl-phenyl)-imidazo[1,2-c]pyrimidin-5-yl]-(4-methoxy-phenyl)-amine; and

2-[7-(3,4-Dimethoxy-phenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]-nicotinamide

or its tautomeric or stereoisomeric form, or its physiologically acceptable salt.

5. A medical composition comprising the compound as claimed in claim 1 or its tautomeric or stereoisomeric form or its physiologically acceptable salt together with one or more pharmaceutically acceptable excipients.

6. A method of treating asthma, which comprises administering to a patient an effective amount of a compound as claimed in claim 1 or its tautomeric or stereoisomeric form or its physiologically acceptable salt.

7. A process for the preparation of the compounds according to claims 1 , comprising that a compound of the formula (II)

in which

Y is CH or N;

R 2 is H, C 1 -C 6 alkyl, carbamoyl, or —COOR 21

wherein R 21 is H or C 1 -C 6 alkyl;

R 3 is thienyl, pyridyl optionally substituted by halogen or C 1 -C 6 alkoxy, naphthyl optionally substituted by C 1 -C 6 alkoxy, dioxane fused phenyl, dioxacyclopentane fused phenyl, or phenyl optionally substituted by one to three substituents selected from the group consisting of halogen, C 1 -C 6 alkyl, nitro, amino, hydroxy, C 1 -C 6 alkylthio, —OR 31 , —OR 32 , —NR 33 R 34 , and —SO 2 R 35 ,

wherein R 31 and R 32 are identical or different and represent C 1 -C 6 alkyl carbonyl, C 1 -C 6 alkoxy carbonyl, C 2 -C 6 alkenyl, di (C 1 -C 6 alkyl) amino carbonyl, C 1 -C 6 alkyl amino carbonyl, —SO 2 —R 311 , straight- or branched-C 1 -C 6 alkyl optionally substituted by R 312 , or cyclo-C 3 -C 7 alkyl optionally substituted by R 312 ,

R 311 represents C 1 -C 6 alkyl, amino, di(C 1 -C 6 alkyl) amino C 1 -C 6 alkyl amino, C 1 -C 6 alkoxy carbonyl C 1 -C 6 alkyl amino, 5-6 membered saturated hetero cyclic ring containing up to 2 heteroatoms of N, S, and/or O and optionally substituted by C 1 -C 6 alkyl or carboxy,

R 312 represents C 1 -C 6 alkoxy, halogen, phenyl optionally substituted by C 1 -C 6 alkoxy, di(C 1 -C 6 alkyl) amino, C 1 -C 6 alkyl and hydroxy C 1 -C 6 alkyl substituted amino, or 5-6 membered saturated hetero cyclic ring containing up to 2 heteroatoms of N, S, and/or O and optionally substituted by one or three substituents selected from the group consisting of C 1 -C 6 alkyl, carbamoyl, and di(C 1 -C 6 alkyl)amino,

R 33 represents H or C 1 -C 6 alkyl,

R 34 represents carboxy C 1 -C 6 alkyl carbonyl, C 1 -C 6 alkyl carbonyl, C 1 -C 6 alkyl optionally substituted by R 341 ,

wherein R 341 represents dimethylamino, C 1 -C 6 alkoxyl, morpholino, phenyl, C 1 -C 6 alkyl substituted piperazino, oxopyrrolidino, or imidazolyl,

or —N R 33 R 34 forms 5-6-membered saturated hetero cyclic ring optionally containing one more hetero atom selected from the group consisting of N, S, and O and optionally substituted by C 1 -C 6 alkyl,

R 35 represents amino, di(C 1 -C 6 alkyl)amino C 1 -C 6 alkyl amino, piperazino optionally substituted by hydroxy C 1 -C 6 alkyl or C 1 -C 6 alkyl, C 1 -C 6 alkoxy carbonyl C 1 -C 6 alkyl amino, morpholino, piperidino optionally substituted by carboxy or C 1 -C 6 alkyl, or hydroxy C 1 -C 6 alkyl amino; and

L represent a leaving group

is reacted with a compound of the formula (III)

HR 1   (III)

in which

R 1 represents —OR 11 , —SR 11 , —SOR 11 , —SO 2 R 11 , —NHR 11 , or —NR 12 R 13 ,

R 11 represents H, phenyl carbonyl, thienyl optionally substituted by COOR 111 (R 111 is H or C 1 -C 6 alkyl), pyrimidyl, C 2 -C 6 alkenyl, imidazolyl optionally substituted by C 1 -C 6 alkyl, triazolyl optionally substituted by C 1 -C 6 alkyl, tetrazolyl optionally substituted by C 1 -C 6 alkyl, thiadiazolyl optionally substituted by C 1 -C 6 alkyl, pyrrolidinyl optionally substituted by C 1 -C 6 alkyl, cyclohexenyl, C 1 -C 10 straight- or branched- or cyclo-alkyl optionally substituted by R 112 , R 113 and/or R 114 , phenyl optionally substituted by R 115 , R 116 , and/or R 117 , pyridyl optionally substituted by R 115 , R 116 , and/or R 117 , or 9-10-membered unsaturated condensed ring which optionally contains up to 3 hetero atoms selected from the group consisting of N, O and S and optionally substitued by R 118

R 112 represents halogen, amino, —COOR 112a (R 112a represents H or C 1 -C 6 alkyl) —CO—NH—CH 3 , —CO—NH—(CH 2 ) p CN (p=0, 1, 2, 3, 4, 5, or 6), —NH—COOR 112a , pyrazinyl, tetrazolyl, dihydrothiophenyl, morpholino, piperidino, di(C 1 -C 6 alkyl)amino, indolyl, pyridinyl, thiophenyl, or phenyl optionally substituted by one to three substituents selected from the group consisting of halogen, C 1 -C 6 alkyl, hydroxy, C 1 -C 6 alkoxy, and trihalogen substituted C 1 -C 6 alkyl,

R 113 represents halogen, hydroxy, or C 1 -C 6 alkoxy-carbonyl,

R 114 represents halogen,

R 115 represents H, halogen, amino, hydroxy, nitro, cyano, C 1 -C 6 alkoxy, carboxy, C 1 -C 6 alkoxy carbonyl, C 1 -C 6 alkyl carbonyl, morpholino-C 1 -C 6 alkyl-oxy, caroboxy-C 1 -C 6 alkyl-oxy, trihalogen substituted methyl, trihalogen substituted methoxy, C 1 -C 10 straight- or branched-alkyl optionally substituted by R 115a , C 3 -C 10 cyclo-alkyl optionally substituted by R 115a , tetrazolyl, amidino, —CON(R 115b )R 115c , —SO 2 N(R 115b )R 115c , —N(R 115b )R 115c , —SO 2 R 115d , —SOR 115d , —SR 115d , or C 2 -C 6 alkenyl optionally substituted by COOR 115e

R 115a represents one or two selected from the group consisting of carboxy, morpholino, morpholino-carbonyl, amino, hydroxy, cyano, C 1 -C 6 alkoxy carbonyl, carbamoyl optionally substituted by cyano-C 1 -C 6 alkyl, methylamino-carbonyl, dimethylamino-carbonyl, —NH—SO 2 —CH 3 , tetrazolyl, dihydrooxazolyl optionally substituted by C 1 -C 6 alkyl, and 9-10 membered unsaturated condensed ring containing one N atom optionally substituted by ═O,

R 115b represents H or C 1 -C 6 alkyl,

R 115c represents H, amino, C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, amidino, morpholino-C 1 -C 6 alkyl carbonyl, carboxy-C 1 -C 6 alkyl carbonyl, or straight- or branched C 1 -C 6 alkyl optionally substituted by one or two selected from the group consisting of hydroxy, phenyl, morpholino, di(C 1 -C 6 alkyl) amino, C 1 -C 6 alkyl and hydroxy C 1 -C 6 alkyl substituted amino, C 1 -C 6 alkoxy-carbonyl, and carboxy,

or R 115b and R 115c together with the adjacent N form 5 or 6 membered saturated hetero cyclic ring optionally having one N or O atoms other than the adjacent N and optionally substituted by C 1 -C 6 alkyl,

R 115d represents hydroxy, hydroxy C 1 -C 6 alkyl, C 1 -C 6 alkyl, hydroxy-carbonyl-C 1 -C 6 alkyl, or C 1 -C 6 alkoxy carbonyl C 1 -C 6 alkyl,

R 115e represents hydrogen or C 1 -C 6 alkyl,

R 116 represents H, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, halogen, or carbamoyl,

R 117 represents H, halogen, or C 1 -C 6 alkoxy,

R 118 represents one to three substituents selected from the group consisting of C 1 -C 6 alkyl, amino, C 1 -C 6 alkoxy, —COOR 118a (R 118a is H or C 1 -C 6 alkyl), and ═O,

R 12 represents C 1 -C 6 alkyl, —(CH 2 ) q —OH, —(CH 2 ) q —CN (q=0, 1, 2, 3, 4, 5, or 6), —CO—C 1 -C 6 alkyl, or —C 2 -C 6 alkenyl,

R 13 is identical to R 11 ,

or R 12 and R 13 together with the adjacent N atom form 4-6 membered saturated heterocyclic ring which may or may not contain 1 heteroatom other than the adjacent N atom selected from the group consisting of O, N, and S,

the 4-6 membered heterocyclic ring optionally forms spiro with dioxacyclopentane, or

is optionally fused with benzene, and/or

is optionally substituted by one or two substituents selected from the group consisting of C 1 -C 6 alkyl carbonyl, C 1 -C 6 alkyl, hydroxy, hydroxy C 1 -C 6 alkyl, carboxyl, C 1 -C 6 alkoxy carbonyl, carbamoyl, phenyl, halogen substituted phenyl, C 1 -C 6 alkoxy substituted phenyl, C 1 -C 6 alkyl substituted phenyl, nitro phenyl, hydroxy phenyl, C 1 -C 6 alkyl carbonyl phenyl, C 1 -C 6 alkoxy carbonyl phenyl, pyridyl optionally substituted by CF 3 , pyrimidyl, C 3-7 cycloalkyl, dioxolanyl, piperidino, halogen substituted phenyl carbonyl, furyl carbonyl, cyano, dimethylamino, benzyl, oxo residue, piperonyl methyl, halogen substituted diphenyl methyl, and trifluorocarbonyl amino,

in inert solvent, if appropriate in the presence of a base and/or in the presence of auxiliary.