Patent DE-19510019-A1 (DE)
Title: New imidazo-quinazoline derivs.
Inventor: HIMMELSBACH FRANK DIPL CHEM DR
IPC: C07D471/14
Filed: 1995-03-20
Abstract: Imidazo-quinazoline derivs. of formula (I), their tautomers, stereoisomers and salts are new. Ra = H or Me; Rb = 2-naphthyl, 1,2,3,4-tetrahydro-6- naphthyl or 5-indanyl; or is Ph substd. with gps. R1-R3. Rc = H, OH, SH, Cl, NH2, COOH, 1-6C alkyl (opt. substd. with 1-3 halogen, 1-3 OH or one NH2, NO2, COOH, CN, aminocarbonyl, 1-4C alkyl-aminocarbonyl, di(1-4C)alkylaminocarbonyl, 1-4C alkoxycarbonyl, 1-4C alkylcarbonyloxy, formyl-amino, 1-4C alkylcarbonylamino, 1-4C alkoxycarbonylamino, benzoylamino, 1-4C alkoxy, 4-7C cycloalkoxy, 1-4C alkylamino, di(1-4C)alkylamino, 3-7C cycloalkylamino, 2-hydroxyethylamino, bis(2-hydroxy-ethyl)amino, (2,3-dihydroxypropyl)amino, tris(hydroxymethyl)methylamino, benzylamino, dibenzylamino, (2-(N,N-dimethylamino)ethyl)amino, (2-(N-acetylamino)-ethylamino, morpholino, 1-pyrrolidinyl, 1-piperidinyl, 3-hydroxy-1-piperidinyl, 4-hydroxy 1-piperidinyl, 4-oxo-1-piperidinyl, thiomorpholino, S-oxido-thiomorpholino, S,S-dioxido-thiomorpholino, 1-piperazinyl, 4-(1-4C)alkyl-1-piperazinyl, 4-formyl-1- piperazinyl, 4-(1-4C)alkylcarbonyl-1-piperazinyl, 4-(1-4C)alkylsulphonyl-1- piperazinyl, 4-(1-4C)alkoxycarbonyl-1- piperazinyl, tetrahydrofuranyl-methylamino, 3-tetrahydrofuranylamino, 3-tetrahydro- pyranyl-amino or 4-tetrahydropyranylamino, provided that on one C of the alkyl there at most 1 OH gp.); or Rc = 1-4C alkoxy, 4-7C cycloalkoxy, aminocarbonyl, 1-4C alkylaminocarbonyl, di(1-4C)alkylaminocarbonyl, 1-4C alkylcarbonylamino, 1-4C alkoxycarbonylamino, benzoylamino, 1-4C alkylamino, di(1-4C)alkylamino, 3-7C cycloalkylamino, 2-hydroxyethylamino, bis(2-hydroxyethyl)-amino, (2,3-dihydroxypropyl)amino, tris(hydroxymethyl)methylamino, morpholino, 1-pyrrolidinyl, 1-piperidinyl, 3-hydroxy-1-piperidinyl, 4-hydroxy-1-piperidinyl, 4-oxo-1-piperidinyl thiomorpholino, S-oxido-thiomorpholino, S,S-dioxido-thiomorpholino, 1-piperazinyl, 4-(1-4C)alkyl-1-piperazinyl, 4-formyl-1-piperazinyl, 4-(1-4C)alkylcarbonyl-1- piperazinyl, 4-(1-4C)alkylsulphonyl-1- piperazinyl, 4-(1-4C)alkoxycarbonyl-1- piperazinyl, tetrahydrofuranyl-methylamino, 3-tetrahydrofuranyl-amino, 3-tetrahydro- pyranylamino, 4-tetrahydropyranyl- amino, tetrahydrofuranyl, tetrahydropyranyl, 1-4C alkylthio, 3-7C cycloalkyl (opt. substd. with 1-3 Me and/or one amino, 1-4C alkylamino, di(1-4C)alkylamino, COOH, aminocarbonyl. 1-4C alkylamino-carbonyl, di(1-4C)alkylaminocarbonyl or 1-4C alkoxycarbonyl), 4-7C cycloalkyl (opt. substd. with 1-3 Me and one OH or 1-4C alkoxy), aryl, 3-7C cycloalkyl-(1-4C)alkyl, 1-4C alkyl substd. with aryl; Rd = 1-6C alkyl (opt. substd. with 1-3 halogen, 1-3 OH or one NH2, NO2 1-4C alkoxy, 4-7C cycloalkoxy, 1-4C alkylamino, di-(1-4C)alkylamino, carboxy, aminocarbonyl, 1-4C alkylaminocarbonyl, di(1-4C)alkyl- aminocarbonyl, 1-4C alkoxycarbonyl, formylamino, 1-4C alkylcarbonylamino, 1-4C alkoxycarbonylamino or 1-4C alkylsulphonyl amino provided that the heteroatoms in the alkyl part are sepd. from the imidazo moiety by at least 2C and there is at most 1 OH attached to one C of the alkyl gp.), 3-7C cycloalkyl (opt. substd. with 1-2 1-4C alkyl gps. and one NH2, NO2, 1-4C alkylamino, di(1-4C)alkylamino, carboxy, aminocarbonyl, 1-4C alkylaminocarbonyl, di(1-4C)alkylamino- carbonyl, formylamino, 1-4C alkoxycarbonyl, 1-4C alkylcarbonylamino, 1-4C alkoxy-carbonylamino or 1-4C alkylsulphonylamino, provided that the heteroatom on the alkyl part is sepd. from the N of the imidazo moiety by at least 2C), 4-7C cycloalkyl (opt. substd. with 1-2 1-4C alkyl gp., and one OH or 1-4C alkoxy gp., provided that the O on the cycloalkyl is sepd. from the N of the imidazo moiety by at least 2C), 3-6C alkenyl (provided the vinyl moiety is not attached to the N of the imidazo moiety), 3-6C alkynyl (provided the ethynyl moiety is not attached to the N of the imidazo moiety), 1-4C alkyl substd. with aryl or 3-6C cycloalkyl; Re+Rf = a bond; or (Rd or Re) + Rc = a linear 3-5C alkylene bridge which is opt. substd. with 1-2 1-4C alkyl and in which one CH2 gp. is opt. replaced with O, S, SO, SO2, NH, N-(1-4C)alkylimino, N-benzylimino, N-formylimino, N-benzyloxycarbonylimino, 1-4C alkylcarbonylimino, 1-4C alkoxycarbonylimino or 1-4C alkylsulphonylimino, provided that the heteroatom in the alkylene bridge is sepd. from the N of the imidazo moiety by at least 2C; and (the other of Rd and Re) + Rf = a bond; R1=H, F, Cl, Br, I, 1-4C alkyl, 1-4C alkoxy, 3-6C cycloalkyl, 5-6C cycloalkoxy, CF3, CF3O, CN, COOH, methoxycarbonyl, ethoxycarbonyl, OH, vinyl, ethynyl or NO2; R2=H, F, Cl, Br, Me, MeO or CF3; R3=H, NH2, 1-4C alkylamino, di(1-4C) alkylamino, acetylamino or Me; In the definitions above the aryl moiety is Ph which is opt. mono-substd. with R4 or mono-, di- or tri-substd. with R5 or mono-substd. with R4 as well as mono- or di-substd. with R5; R4=CN, COOH, aminocarbonyl, 1-4C alkylaminocarbonyl, di(1-4C)alkylaminocarbonyl, 1-4C alkoxycarbonyl, 1-4C alkylcarbonyl, 1-4C alkylsulphenyl, 1-4C alkylsulphinyl, 1-4C alkylsulphonyl, 1-4C alkylsulphonyloxy, CF3, CF3O, NO2, NH2, 1-4C alkylamino, di(1-4C)alkylamino, 1-4C alkylcarbonylamino, phenyl(1-4C) alkylcarbonylamino, phenylcarbonylamino, 1-4C alkylsulphonylamino, phenyl-(1-4C)alkylsulphonylamino, phenylsulphonylamino, N-(1-4C)alkyl(1-4C) alkylcarbonylamino, N-(1-4C)alkylphenyl(1-4C) alkylcarbonylamino, N-(1-4C)alkylphenyl-carbonylamino, N-(1-4C)alkyl(1-4C)alkyl- sulphonylamino, N-(1-4C)alkylphenyl (1-4C)- alkylsulphonylamino,  N-(1-4C)alkylphenylsulphonylamino, aminosulphonyl or mono- or di(1-4C)alkylaminosulphonyl; R5=1-4C alkyl, OH, 1-4C alkoxy, F, Cl, Br, I; or 2 R5 gps., provided they are on neighbouring C atoms can form a 3-6C alkylene gp., 1,3-butadien-1,4-diylene or methylene dioxy.