Substituted aminoindanes and analogs thereof, and the pharmaceutical use thereof

A compound of the formula I

• in which
• A is a 6 to 10 membered aryl radical or a 5 to 10 membered heteroaryl radical, where the aryl and heteroaryl radical may be mono- or bicyclic, and the heteroaryl radical may comprise one or more heteroatoms selected from the group of nitrogen, oxygen and sulfur;
• where one or more hydrogen atoms in said mono- or bicyclic aryl or heteroaryl radicals may be replaced by substituents R1 which are selected independently of one another from the group of F, Cl, Br, I, (C1-C10-alkyl-, (C2-C10)-alkenyl-, (C2-C10)-alkynyl-, (C3-C14)-cycloalkyl-, (C4-C20)-cycloalkylalkyl-, (C4-C20)-cycloalkylalkyloxy-, (C1-C10)-alkoxy-, (C1-C10)-alkylthio-, (C6-C14)-aryl-, (C2-C13)-heteroaryl, —CN, —NR13R14, —C(O)R12, —SF5, —S(O)nR12, —C(O)OR12, —C(O)NR13R14 and —S(O)nNR13R14;
• where two adjacent radicals R1 may also form a saturated or partly unsaturated (C5-C10)-cycloalkyl radical or a saturated or partly unsaturated (C2-C9)-cycloheteroalkyl radicals, where the cycloheteroalkyl radical may comprise 1, 2 or 3 nitrogen, 1 or 2 oxygen, 1 or 2 sulfur, 1 or 2 nitrogen and 1 oxygen or 1 sulfur atom;
• where said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkyloxy, cycloheteroalkyl, alkoxy, and alkylthio radicals may be substituted independently of one another one or more times by F, OH or (C1-C10)-alkoxy;
• B is a mono- or fused bicyclic radical selected from the group
• of 6 to 10 membered aryl radicals,
• of 5 to 10 membered heteroaryl radicals,
• of 3 to 10 membered cycloalkyl radicals,
• of 9 to 14 membered cycloalkylaryl radicals,
• of 8 to 14 membered cycloalkylheteroaryl radicals,
• of 3 to 10 membered cycloheteroalkyl radicals,
• of 9 to 14 membered cycloheteroalkylaryl radicals and
• of 8 to 14 membered cycloheteroalkylheteroaryl radicals,
• where the cycloalkyl or cycloheteroalkyl units may be saturated or partly unsaturated, and
• where the heterocyclic groups may comprise one or more heteroatoms selected from the group of nitrogen, oxygen and sulfur;
• where one or more hydrogen atoms in the radicals B may be replaced by substituents R5 which are selected independently of one another from the group of (C1-C10)-alkyl radicals, of (C2-C10)-alkenyl radicals, of (C2-C10)-alkynyl radicals, of (C1-C10)-alkoxy radicals, of (C1-C10)-alkylthio radicals, of (C3-C14)-cycloalkyl radicals, of (C4-C20)-cycloalkylalkyl radicals, of (C4-C20)-cycloalkylalkyloxy, of (C2-C19)-cycloheteroalkyl radicals, of (C3-C19)-cycloheteroalkylalkyl radicals, of (C3-C11)-cycloalkyloxy radicals, of (C2-C11)-cycloheteroalkyloxy radicals, of (C6-C10)-aryl radicals, of (C1-C9)-heteroaryl radicals, of (C9-C14)-cycloalkylaryl radicals, of (C5-C13)-cycloalkylheteroaryl radicals, (C7-C13)-cycloheteroalkylaryl radicals and (C4-C12)-cycloheteroalkylheteroaryl radicals, where
• the cycloalkyl and cycloheteroalkyl units may be saturated or partly unsaturated,
• and where one or more hydrogen atoms in said radicals R5 may be replaced by further radicals which are selected independently of one another from the group of R11 radicals,
• it is further possible for R5 to be one or more radicals which are selected independently of one another from the group of OH, (═O), NH2, F, Cl, Br, I, CN, NO2, —NR17R18, —NR16COR17, —NR16COOR17, —NR16CONR17R18, —NR16-S(O)2—R17, —NR16-S(O)2—NR17R18, —COOR16, —COR16;
• —CO(NR17R18), S(O)nR16 and —S(O)2NR17R18, where
• R16, R17 and R18 independently of one another for a radical selected from the group of H, (C2-C19)-cycloheteroalkyl, (C3-C14)-cycloalkyl, (C6-C10)-aryl and (C1-C10)-alkyl radicals,
• all of which may be substituted independently of one another by OH, (═O), F, Cl, Br, I, CN, NO2, —NR13R14, —NR13COR12, —NR13COOR12, —NR12CONR13R14, —NR13-S(O)2—R12, —NR12-S(O)2—R13R14, —COOR12, —COR12;
• —CO(NR13R14), —S(O)nR12, —S(O)2NR13R14, (C3-C14)-cycloalkyl, (C4-C20)-cycloalkylalkyl, (C2-C19)-cycloheteroalkyl, (C3-C19)-cycloheteroalkylalkyl, (C6-C10)-aryl or (C1-C9)-heteroaryl,
• and where R17 and R18 can form together with the nitrogen to which they are bonded a 4-7 membered, saturated, unsaturated or partly unsaturated heterocycle having 1 to 13 carbon atoms which may additionally comprise one or more heteroatoms from the list —O—, —S(O)n—, ═N— and —NR15-,
• where the heterocycle formed may be substituted independently of one another one or more times by F, OH, (═O), NH2, NH(C1-C4)alkyl, N((C1-C4)alkyl)2, CN or (C1-C10)-alkoxy, (C1-C10)-alkyl, (C2-C10)-alkenyl, (C2-C10)-alkynyl, (C3-C14)-cycloalkyl, (C4-C20)-cycloalkylalkyl, (C2-C20)-cycloheteroalkyl, (C3-C19)-cycloheteroalkylalkyl, each of which may in turn carry independently of one another one or more radicals F, OH, (═O), NH2, NH(C1-C4)alkyl, N((C1-C4)alkyl)2, CN or (C1-C10)-alkoxy;
• L is a covalent bond;
• X is a group —O—;
• R2 is absent or is one or more substituents which may be selected independently of one another from the group of F, (C1-C10)-alkyl and (C1-C10)-alkoxy radical, where the alkyl and alkoxy radicals may be substituted independently of one another one or more times by F;
• R3 and R4 are independently of one another a hydrogen radical or a radical which is selected from the group of (C1-C10)-alkyl radicals, of (C2-C10)-alkenyl radicals, of (C2-C10)-alkynyl radicals, of (C3-C14)-cycloalkyl radicals, of (C4-C20)-cycloalkylalkyl radicals, of (C2-C19)-cycloheteroalkyl radicals, of (C3-C19)-cycloheteroalkylalkyl radicals, of (C6-C10)-aryl radicals, of (C7-C20)-arylalkyl radicals, of (C1-C9)-heteroaryl radicals and of (C2-C19)-heteroarylalkyl radicals, where
• the radicals R3 and R4 may be substituted independently of one another one or more times by a radical from the group of OH, NH2, (═O), F, Cl, Br, I, CN, NO2, —NR13R14, —NR13COR12, —NR13COOR12, —NR12CONR13R14, —NR13-S(O)2—R12, —NR13-S(O)2—NR13R14, —COOR12, —COR12;
• —CO(NR13R14) and S(O)nR12, —S(O)2R13R14, or
• R3 and R4 form together with the nitrogen to which they are bonded a 4-10 membered, saturated, unsaturated or partly unsaturated heterocycle which may additionally comprise one or more heteroatoms from the list —O—, —S(O)n—, ═N— and —NR8-, where
• the heterocyclic radicals may be substituted independently of one another one or more times by radicals selected from the group of R7 and R9, and where
• the heterocyclic radicals formed by R3 and R4 may be bridged by a bond, by a saturated or unsaturated (C1-C10)-alkyl or (C1-C9)-heteroalkyl chain or by —NR15-, —O— or —S—, and where the alkyl and heteroalkyl chains may also form a spirocyclic ring system with the ring system formed by R3 and R4, where the alkyl and heteroalkyl bridges may be substituted independently of one another one or more times by radicals selected from the group of R7 and R9,
• and where
• R8 in the group —NR8- may form with the ring which R3 and R4 may form a further saturated, unsaturated or partly unsaturated heterocycle which may be substituted independently of one another one or more times by radicals selected from the group of R7 and R9, and may additionally comprise one or more heteroatoms from the list —O—, —S(O)n—, —N═ and —NR19-;
• R7 are a (C1-C10)-alkyl radical or (C1-C14)-cycloalkyl radical, where the alkyl radical may be substituted independently of one another one or more times by R9;
• R8 is an H, a (C1-C10)-alkyl radical or (C1-C14)-cycloalkyl radical, COR12, —CO(NR13R14), S(O)nR12 or —S(O)2NR13R14, where the alkyl radical may be substituted independently of one another one or more times by R10;
• R9 is a radical selected from the group of OH, (═O), F, Cl, Br, I, CN, NO2, —NR13R14, —NR13COR12, —NR13COOR12, —NR12CONR13R14, —NR13-S(O)2—R12, —NR13-S(O)2—NR13R14, —COOR12, —COR12, —CO(NR13R14), S(O)nR12, —S(O)2NR13R14, (C3-C14)-cycloalkyl, (C4-C20)-cycloalkylalkyl, (C1-C10)-alkoxy, (C2-C19)-cycloheteroalkyl, (C3-C19)-cycloheteroalkylalkyl, (C6-C10)-aryl radicals and (C1-C9)-heteroaryl radicals;
• R10 is a radical selected from the group of F, OH, CN, (C1-C10)-alkoxy, (C1-C10)-alkylthio, NO2, —NR13R14, —NR13COR12, —NR13COOR12, —NR13CONR13R14, —NR13-S(O)2—R12, —NR12-S(O)2—NR13R14, —COOR12, —COR12, —CO(NR13R14), S(O)nR12 and —S(O)2NR13R14;
• R11 is a radical selected from the group of (C1-C10)-alkyl, (C2-C10)-alkenyl, (C2-C10)-alkynyl, (C1-C10)-alkoxy, (C1-C20)-alkylthio, (C3-C14)-cycloalkyl, (C4-C10)-cycloalkylalkyl, (C2-C13)-cycloheteroalkyl, (C4-C19)-cycloheteroalkylalkyl, (C3-C14)-cycloalkyloxya and (C2-C13)-cycloheteroalkyloxy,
• all of which may be substituted independently of one another one or more times by R10;
• (═O), Cl, Br, I and R10;
• R12, R13 and R14 may independently of one another be H, (C1-C10)-alkyl, (C2-C10)-alkenyl, (C2-C10)-alkynyl, (C3-C14)-cycloalkyl, (C4-C10)-cycloalkylalkyl, (C2-C13)-cycloheteroalkyl, (C3-C19)-cycloheteroalkylalkyl, (C6-C10)-aryl, each of which may be substituted independently of one another one or more times by F, OH, (═O), NH2, NH(C1-C4)alkyl, N((C1-C4)alkyl)2, CN or (C1-C10)-alkoxy;
• or
• R13 and R14 may form together with the nitrogen to which they are bonded a 4-7 membered, saturated, unsaturated or partly unsaturated heterocycle having 1 to 13 carbon atoms, which may additionally comprise one or more heteroatoms from the list —O—, —S(O)n—, ═N— and —NR15-, where
• the formed heterocycle may be substituted independently of one another one or more times by F, OH, (═O), NH2, NH(C1-C4)alkyl, N((C1-C4)alkyl)2, CN or (C1-C10)-alkoxy, (C1-C10)-alkyl, (C2-C10)-alkenyl, (C2-C10)-alkynyl, (C3-C14)-cycloalkyl, (C4-C20)-cycloalkylalkyl, (C2-C20)-cycloheteroalkyl or (C3-C19)-cycloheteroalkylalkyl, each of which may in turn carry independently of one another one or more radicals F, OH, (═O), NH2, NH(C1-C4)alkyl, N((C1-C4)alkyl)2, CN or (C1-C10)-alkoxy;
• R15 is a radical selected from the group of H, (C1-C10)-alkyl, (C2-C10)-alkenyl, (C2-C10)-alkynyl, (C3-C14)-cycloalkyl, (C4-C20)-cycloalkylalkyl, (C2-C13)-cycloheteroalkyl and (C3-C19)-cycloheteroalkylalkyl, each of which may be substituted independently of one another one or more times by F, OH, CN or (C1-C10)-alkoxy;
• R19 is an H, a (C1-C10)-alkyl radical or (C1-C14)-cycloalkyl radical, COR12, —CO(NR13R14), S(O)nR12 or —S(O)2NR13R14, where the alkyl radical may be substituted independently of one another one or more times by R10;
• and in which
• n is 0, 1 or 2;
• p is 1 or 2 and
• q is 0,
• and the pharmaceutically acceptable salts thereof,
• and in which
• i) in the case where A is phenyl, B is phenyl or benzodioxolanyl and R3 and R4 are H, (C1-C10)-alkyl, (C3-C14)-cycloalkyl or (C7-C20)-arylalkyl or R3 and R4 together are an unsubstituted pyrrolidinyl, morpholinyl, piperidinyl, piperazinyl radical or 4-methylpiperazinyl radical, at least one R5 radical which is not a (C1-C10)-alkyl, (C1-C10)-alkoxy, OH, CF3, F, Cl, Br or I radical must be present,
• ii) in the case where A is phenyl and R3 and R4 are a (C1-C10)-alkyl, (C3-C14)-cycloalkyl or a (C4-C20)-cycloalkylalkyl radical, at least one R5 radical which is not an F, Cl, Br, I, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3, OCF3, CN, NO2, NH2, —NH((C1-C10)-alkyl), —N((C1-C10)-alkyl)2, unsubstituted or substituted benzoyl or an unsubstituted or substituted phenyl-(CH2)r—Y—(CH2)s-radical, with Y being a bond or an oxygen and r and s being 0 to 4, where r+s is not greater than 4, must be present and
• iii) in the case where A is a phenyl radical, p is not 1.