Triazolo and tetrazolo pyrimidine derivatives as HNE inhibitors for treating COPD

A compound of formula (I)

• in which
• A represents C—H,
• Y represents N,
• Z represents C—R9 in which
• R9 represents hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkoxycarbonyl, (C3-C6)-cycloalkyl, phenyl or 5- or 6-membered heteroaryl,
• where (C1-C6)-alkyl may be substituted by hydroxyl, (C1-C4)-alkoxy, (C3-C6)-cycloalkyl or phenyl and up to three times by fluorine
• and where
• the cycloalkyl groups mentioned may be substituted up to two times by identical or different substituents from the group consisting of (C1-C4)-alkyl and up to two times by fluorine
• and
• the phenyl and heteroaryl groups mentioned may be substituted up to two times by identical or different substituents from the group consisting of fluorine, chlorine, cyano, (C1-C4)-alkyl, difluoromethyl, trifluoromethyl, (C1-C4)-alkoxy, difluoromethoxy and trifluoromethoxy,
• or
• R9 represents a group of the formula —SO2—NR10R11 or —NR12R13 in which
• R10 and R11 are identical or different and independently of one another represent hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, phenyl or 5- or 6-membered heteroaryl,
• R12 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, phenyl or (C1-C6)-alkylsulfonyl,
• where (C1-C6)-alkyl may be substituted by cyano, hydroxyl, (C1-C4)-alkoxy, hydroxycarbonyl, (C1-C4)-alkoxycarbonyl, aminocarbonyl, mono-(C1-C4)-alkylaminocarbonyl, di-(C1-C4)-alkylaminocarbonyl, (C3-C6)-cycloalkyl or phenyl and up to three times by fluorine
• and where
• the cycloalkyl groups mentioned may be substituted up to two times by identical or different substituents from the group consisting of (C1-C4)-alkyl and up to two times by fluorine
• and
• the phenyl groups mentioned may be substituted up to two times by identical or different substituents from the group consisting of fluorine, chlorine, cyano, (C1-C4)-alkyl, difluoromethyl, trifluoromethyl, (C1-C4)-alkoxy, difluoromethoxy and trifluoromethoxy,
• R13 represents hydrogen, (C1-C6)-alkyl or a group of the formula —C(═O)—R14, —C(═O)—O—R15 or —C(═O)—NR16R17 in which
• R14 represents hydrogen, (C1-C8)-alkyl, (C3-C6)-cycloalkyl, 4- to 6-membered heterocyclyl, phenyl or 5- or 6-membered heteroaryl,
• where (C1-C8)-alkyl may be substituted by hydroxyl, (C1-C4)-alkoxy, benzyloxy, phenoxy, (C1-C4)-acyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C4)-acylamino, (C1-C4)-alkoxycarbonylamino, (C3-C6)-cycloalkyl or phenyl and up to three times by fluorine and up to two CH2 groups in (C1-C8)-alkyl may be exchanged for an oxygen atom provided this results in a stable compound
• and where
• the cycloalkyl and heterocyclyl groups mentioned may be substituted up to two times by identical or different substituents from the group consisting of (C1-C4)-alkyl and up to two times by fluorine
• and
• the phenyl and heteroaryl groups mentioned may be substituted up to two times by identical or different substituents from the group consisting of fluorine, chlorine, cyano, (C1-C4)-alkyl, difluoromethyl, trifluoromethyl, (C1-C4)-alkoxy, difluoromethoxy, trifluoromethoxy and hydroxycarbonyl,
• R15 represents (C1-C6)-alkyl which may be substituted by (C3-C6)-cycloalkyl or phenyl,
• R16 and R17 are identical or different and independently of one another represent hydrogen or (C1-C6)-alkyl which may be substituted by hydroxyl or (C1-C4)-alkoxy,
• or
• R12 and R13 together with the nitrogen atom to which they are attached form a 5- or 6-membered heterocycle which may contain a further ring heteroatom from the group consisting of N, O and S and which may be substituted up to two times by identical or different substituents from the group consisting of (C1-C4)-alkyl, hydroxyl, (C1-C4)-alkoxy and oxo and may be fused to a phenyl ring,
• or in which
• R7 and R9, if both are present, are attached to one another and together with the carbon atoms to which they are attached form a fused phenyl, pyridyl or pyrimidyl ring which may in each case be substituted up to two times by identical or different substituents from the group consisting of fluorine, chlorine, cyano, (C1-C4)-alkyl, difluoromethyl, trifluoromethyl, (C1-C4)-alkoxy, difluoromethoxy and trifluoromethoxy,
• R1 represents hydrogen
• or —S(O)n—R20 in which
• R20 represents (C1-C6)-alkyl
• and
• n represents the number 2,
• R2 represents cyano or a group of the formula —C(═O)—R21, —C(═O)—O—R21 or —C(═O)—NH—R21 in which
• R21 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-alkenyl or (C3-C6)-cycloalkyl,
• where (C1-C6)-alkyl and (C3-C6)-cycloalkyl for their part may be substituted up to two times by identical or different substituents from the group consisting of hydroxyl, (C1-C4)-alkoxy, hydroxycarbonyl, (C1-C4)-alkoxycarbonyl, amino, mono- and di-(C1-C4)-alkylamino and in (C1-C6)-alkyl and (C3-C6)-cycloalkyl in each case one CH2 group may be replaced by an oxygen atom provided this results in a chemically stable compound,
• R3 represents methyl or ethyl
• or
• R2 and R3 are attached to one another and together form a fused group of the formula
• in which
• * denotes the point of attachment to the 5-position, marked in formula (I), of the dihydropyrimidine ring
• and
• ** denotes the point of attachment to the 6-position, marked in formula (I), of the dihydropyrimidine ring
• and
• R22 represents hydrogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl,
• where (C1-C6)-alkyl may be substituted by hydroxyl, (C1-C4)-alkoxy, aminocarbonyl, aminocarbonylamino, (C1-C4)-acylamino or (C3-C6)-cycloalkyl,
• R4 represents nitro or trifluoromethyl
• and
• R5 represents hydrogen, fluorine or chlorine,
• or a salt thereof.