Thiazolyl-dihydro-quinazoline compounds and processes for preparing same

A process of preparing a compound of the formula (I),

• wherein
• A denotes CH or N,
• n denotes 1, 2, 3 or 4,
• R1 denotes hydrogen or a group, optionally substituted, consisting of C1-4-alkyl, OR1.1 and NR1.1.1R1.1.2;
• R1.1, R1.2 which may be identical or different, denote H or C1-4-alkyl;
• or
• NR1.1R1.2 denotes a 5- to 6-membered heterocycle, optionally containing a further N atom;
• R2 which may be identical or different, denote hydrogen or
• a group selected from among F, Cl, Br, I, CN, CF3, CF2H, CFH2 and NH2;
• or
• a group, optionally substituted, selected from among —O—C1-4-alkyl, C1-4-alkyl and C2-6-alkenyl;
• R4 denotes hydrogen, OH, NH2, or
• a group, optionally substituted, selected from among C1-6-alkyl, C2-6-alkenyl, C3-6-cycloalkyl, —N(C1-4-alkyl)2 and —NH(C1-4-alkyl);
• R3 denotes a group selected from among:
• wherein
• X denotes a group, optionally substituted, selected from among C1-6-alkylene, C2-6-alkenylene, C1-6-alkynylene, C3-7-cycloalkylene, C6-7-cycloalkenylene and —C1-4-alkylene-C3-7-cycloalkylene;
• Y denotes a bond or X;
• R5, R6, R7 which may be identical or different, denote hydrogen or a group, optionally substituted, selected from among C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-6-haloalkyl, C3-8-cycloalkyl, C3-8-cycloalkenyl, C3-7-cycloalkyl-C1-4-alkyl, aryl, heteroaryl, spiro, heterocycloalkyl, aryl-C1-6-alkyl, heteroaryl-C1-6-alkyl and heterocycloalkyl-C1-6-alkyl, or
• NR6R7 form a five-, six- or seven-membered ring consisting of carbon atoms and optionally a nitrogen, oxygen or sulphur atom as further heteroatoms or a ring selected from among:
• R5.1 which may be identical or different, denote hydrogen or a group selected from among C1-6-alkyl, C3-8-cycloalkyl, —CO—C1-3-alkyl and CONH2;
• or
• R5 and R6 together form a saturated or unsaturated alkylene bridge which is optionally substituted and may optionally contain a further nitrogen, oxygen or sulphur atom;
• or R3 is
• x, y which may be identical or different denote 0, 1, 2, 3, 4 or 5;
• W denotes O, NR9 or CR9R10;
• R8 denotes H, OR8.1, NR8.1R8.2 or optionally substituted C1-6-alkyl;
• R8.1, R8.2 which may be identical or different, denote hydrogen, COR8.1.1, CONR8.1.1R8.1.2, SO2NR8.1.1R8.1.2 or SO2R8.1.1
• or a group, optionally substituted, selected from among C1-6-alkyl, C3-6-alkenyl, C3-6-alkynyl, C3-8-cycloalkyl and C3-7-cycloalkyl-C1-4-alkyl, or
• NR8.1R8.2 together form a five-, six- or seven-membered ring which may optionally contain a further heteroatom;
• R8.1.1, R8.1.2 which may be identical or different, denote hydrogen or a group, optionally substituted, selected from among C1-6-alkyl, C3-8-cycloalkyl and C3-7-cycloalkyl-C1-4-alkyl, or
• NR8.1.1R8.1.2 together form a five- or six-membered ring, which may optionally contain a further heteroatom;
• R9, R10 which may be identical or different, denote a group, optionally substituted by OMe, CN, F, Cl or Br, selected from among C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-8-cycloalkyl, C3-8-cycloalkenyl, C3-7-cycloalkyl-C1-4-alkyl, aryl, heteroaryl, spiro, heterocycloalkyl, (aryl-C1-6-alkyl-) and heteroaryl-C6-10-alkyl (heteroaryl-C1-6-alkyl);
• or
• R9, R10, which may be identical or different, denote hydrogen, COR9.1, CONR9.1R9.2, SO2R9.1 or SO2NR9.1R9.2;
• R9.1, R9.2 which may be identical or different, denote hydrogen or an optionally substituted group selected from among C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-6-haloalkyl, C3-8-cycloalkyl, C3-7-cycloalkyl-C1-4-alkyl, aryl, heteroaryl, spiro, heterocycloalkyl, aryl-C1-6-alkyl- and heteroaryl-C1-6-alkyl-;
• or
• NR9.1R9.2 together form a five- or six-membered ring, which may optionally contain a further heteroatom,
• comprising
• (a) reacting a compound of formula (II)
• wherein R1 has the meaning specified,
• with a compound of formula
• wherein R4 has the specified meaning and Ag denotes a leaving group, and
• (b) reacting the compound of general formula (III)
• resulting from step (a),
• wherein R1 and R4 have the meanings specified,
• with a compound of general formula
• wherein R2 and n have the meanings specified and B denotes a leaving group, and
• (c) reacting a compound of general formula (IV)
• resulting from step (b),
• wherein R1, R2, R4 and n have the meanings specified and B denotes a leaving group,
• with a compound of general formula
• wherein R3 has the specified meaning.