Substituted azaquinazolines having an antiviral action
View Patent ↗This invention relates to substituted azaquinazolines, to a process for their preparation, to pharmaceutical compositions containing them, and to their use for the treatment and/or prophylaxis of diseases, especially for use as antiviral agents, in particular against cytomegaloviruses.
1. A compound of the formula
in which
Ar is aryl, in which aryl may be substituted by 1 to 3 substituents, where the substituents are selected independently of one another from the group consisting of alkyl, alkoxy, formyl, hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, trifluoromethyl, halogen, cyano, hydroxy, amino, alkylamino, aminocarbonyl and nitro,
in which alkyl may be substituted by 1 to 3 substituents, where the substituents are selected independently of one another from the group consisting of halogen, amino, alkylamino, hydroxy and aryl,
or two of the substituents on the aryl form together with the carbon atoms to which they are bonded a 1,3-dioxolane, a cyclopentane ring or a cyclohexane ring, and the optionally present third substituent is selected independently thereof from the group consisting of alkyl, alkoxy, formyl, hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, trifluoromethyl, halogen, cyano, hydroxy, amino, alkylamino, aminocarbonyl and nitro,
Q 1 , Q 2 , Q 3 and Q 4 are CH or N,
where exactly one of Q 1 , Q 2 , Q 3 and Q 4 are N and the others are simultaneously CH,
R 1 is hydrogen, amino, alkyl, alkoxy, alkylamino, alkylthio, cyano, halogen, nitro or trifluoromethyl,
R 2 is hydrogen, alkyl, alkoxy, alkylthio, cyano, halogen, nitro or trifluoromethyl,
R 3 is amino, alkyl, alkoxy, alkylamino, alkylthio, cyano, halogen, nitro, trifluoromethyl, alkylsulphonyl or alkylaminosulphonyl,
or
one of the radicals R 1 , R 2 and R 3 is hydrogen, alkyl, alkoxy, cyano, halogen, nitro or trifluoromethyl, and the other two form together with the carbon atoms to which they are bonded a 1,3-dioxolane, a cyclopentane ring or a cyclohexane ring,
R 4 is hydrogen or alkyl,
R 5 is hydrogen or alkyl,
or
the radicals R 4 and R 5 in the piperazine ring are bonded to exactly opposite carbon atoms and form a methylene bridge optionally substituted by 1 to 2 methyl groups,
R 6 is hydrogen, alkyl, alkoxy, alkylthio, formyl, hydroxycarbonyl, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, trifluoromethyl, halogen, cyano, hydroxy or nitro,
and
R 7 is hydrogen, alkyl, alkoxy, alkylthio, formyl, hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, trifluoromethyl, halogen, cyano, hydroxy or nitro,
or a salt-thereof.
2. The compound according to claim 1 , characterized in that
Ar is phenyl, in which phenyl may be substituted by 1 to 3 substituents, where the substituents are selected independently of one another from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, hydroxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, trifluoromethyl, fluorine, chlorine, bromine, cyano, hydroxy, amino, C 1 -C 6 -alkylamino and nitro,
or two of the substituents on the phenyl form together with the carbon atoms to which they are bonded a 1,3-dioxolane, and the optionally present third substituent is selected independently thereof from the group consisting of alkyl, alkoxy, formyl, hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, trifluoromethyl, halogen, cyano, hydroxy, amino, alkylamino, aminocarbonyl and nitro,
Q 1 , Q 2 and Q 3 are CH or N,
where always exactly one of Q 1 , Q 2 and Q 3 is N and the others are simultaneously CH,
Q 4 is CH,
R 1 is hydrogen, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -alkylthio, fluorine or chlorine,
R 2 is hydrogen, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -alkylthio, fluorine or chlorine,
R 3 is C 1 -C 4 -alkyl, cyano, fluorine, chlorine, nitro, trifluoromethyl or C 1 -C 3 -alkylsulphonyl,
or
one of the radicals R 1 , R 2 and R 3 is hydrogen, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, cyano, halogen, nitro or trifluoromethyl, and the other two form together with the carbon atoms to which they are bonded a cyclopentane ring or a cyclohexane ring,
R 4 is hydrogen or methyl,
R 5 is hydrogen,
R 6 is hydrogen, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, hydroxycarbonyl, aminocarbonyl, trifluoromethyl, fluorine, chlorine, cyano, hydroxy or nitro,
and
R 7 is hydrogen, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, fluorine, chlorine, cyano or hydroxy.
3. The compound according to claim 1 or 2 , characterized in that
Ar is phenyl, in which phenyl may be substituted by 1 to 2 substituents, where the substituents are selected independently of one another from the group consisting of methyl, methoxy, fluorine and chlorine,
Q 1 , Q 2 and Q 3 are CH or N,
where always exactly one of Q 1 , Q 2 and Q 3 is N, and the others are simultaneously CH,
Q 4 is CH,
R 1 is hydrogen, methyl or methoxy, methylthio, fluorine or chlorine,
R 2 is hydrogen,
R 3 is methyl, isopropyl, tert-butyl, cyano, fluorine chlorine, nitro or trifluoromethyl,
R 4 is hydrogen,
R 5 is hydrogen,
R 6 is hydrogen, aminocarbonyl, fluorine, chlorine, cyano or hydroxy,
and
R 7 is hydrogen.
4. The compound according to claim 1 or 2 , characterized in that
Ar is phenyl, in which phenyl may be substituted by 1 to 2 substituents, where the substituents are selected independently of one another from the group consisting of methyl, methoxy, fluorine and chlorine,
Q 1 , Q 2 and Q 3 are CH or N,
where always exactly one of Q 1 , Q 2 and Q 3 is N, and the others are simultaneously CH,
Q 4 is CH,
R 1 is hydrogen, methyl or methoxy,
R 2 is hydrogen,
R 3 is methyl, tert-butyl, chlorine or trifluoromethyl,
R 4 is hydrogen,
R 5 is hydrogen,
R 6 is hydrogen
and
R 7 is hydrogen.
5. A pharmaceutical composition comprising a compound according to any of claims 1 to 4 in combination with an inert, non-toxic, pharmaceutically suitable excipient.