| 主权项 |
1. A 5-ring heteroaromatic compound of general formulaand/or corresponding enantiomeric, diastereomeric, and/or tautomeric forms thereof, and/or pharmaceutically acceptable salts thereof, and/or active substance precursor (“prodrugs”) thereof, wherein the stated radicals have the following definitions:
W: is a radical of general formula W1 or W2 wherein A: is NO2, NH2, CN, CF3, OCF3, CHF3, OCHF2, COOH, O—CH2—COOH, halogen, SH, or in each case optionally substituted O—C1-C6 alkyl, S—C1-C6 alkyl, —O—CO—C1-C6alkyl, —O—CO aryl, —O—CO hetaryl, —O—COO—C1-C6 alkyl, or in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C1-C4 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4 alkylene-hetaryl, or C1-C4 alkylene-aryl, of
in each case optionally substituted O—RA1, CO—RA1, S——RA1, SO——RA1, CO—O—RA1, NRA4—CO—O—RA1, O—CH2—COO—RA1, NRA2RA3, CONH2, SO2NH2, NRA4, —CO—RA1, SO2—RA1, NRA4—SO2—RA1, SO2—NRA2RA3, or CO—NRA2RA3; RA1: is in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C2 cycloalkyl, C1-C4 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4 alkylene-aryl, C2-C6 alkenylene-aryl, C1-C6 alkylene-hetaryl; RA2: is hydrogen, or in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4 alkylene-aryl, C1-C4 alkylene-hetaryl, C1-C6 alkylene-O—C1-C6 alkyl, CO—C1-C6 alkyl, CO-aryl, CO-hetaryl, CO—C1-C4 alkylene-aryl, CO—C1-C4 alkylene hetaryl, CO—O—C1-C6 alkyl, CO—O-aryl, CO—O—C1-C4 alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4 alkylene-hetaryl, SO2 −C1-C6 alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4 alkylene-aryl, or SO2—C1-C4 alkylene-hetaryl; RA3: is in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkylene-C3-C2 cycloalkyl, C1-C4 alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4 alkylene-aryl, C1-C4 alkylene-hetaryl, C1-C6 alkylene-O—C1-C6 alkyl, CO—C1-C6 alkyl, CO—C1-C6 alkyl, CO-aryl, CO-hetaryl, CO—C1-C4 alkylene-aryl, CO—C1-C4 alkylene-hetaryl, CO—O—C1-C6 alkyl, CO—O-aryl, CO—O—C1-C4 alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4 alkylene-hetaryl, SO2—C1-C6 alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4 alkylene-aryl, or SO2—C1-C4 alkylene-hetaryl; or the radicals RA2 and RA3 together with the nitrogen form a 3- to 7-membered saturated or aromatic heterocycle which is optionally substituted in each case, which may contain one, two, or three further heteroatoms, which may be different or the same, from the group O, N, S, wherein two radicals substituted on this heterocycle together may optionally form a 3- to 7-membered anellated, saturated, unsaturated, or aromatic carbocycle or heterocycle, wherein the heterocycle may contain up to three heteroatoms O, N, S which may be different or the same, and wherein the cyclic compound thus formed may optionally be substituted, or a further 3- to 7-membered, optionally substituted cyclic compound may be condensed thereon; RA4: is hydrogen, or in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, aryl, C1-C4 alkylene-aryl, C1-C6 alkylene-O—C1-C6 alkyl; hetaryl; B: hydrogen, or is defined as for radical A, independently of radical A, or two of the radicals A, B, or Rw1 in each case independently form, together with the attached C atoms, a 3- to 7-membered, saturated, unsaturated, or aromatic carbocycle which is optionally substituted in each case, or a 3- to 7-membered saturated, unsaturated, or aromatic heterocycle which in each case is optionally substituted and which may contain one, two, or three further heteroatoms, which may be different or the same, selected from the group comprising O, N, and S, wherein in each case two radicals substituted on this carbocycle or heterocycle together may optionally form a 3- 7-membered anellated, saturated, unsaturated, or aromatic carbocycle or heterocycle, wherein the heterocycle may contain up to three heteroatoms O, N, S which may be different or the same, and wherein the cyclic compound that is formed may optionally be substituted; Rw1: is hydrogen, OH, halogen, NO2, NH2, CN, CF3, CHF2, CH2F, OCF3, OCHF2, OCH2F,
or in each case optionally substituted C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 alkylene-O—C1-C6 alkyl, C1-C6 thioalkyl, aryl hetaryl, O—C1-C6 alkyl, O-benzyl, C1-C6 alkylamino, C1-C6 dialkylamino, pyrrolidinyl, piperidinyl, morpholinyl, CO—C1-C6 alkyl, SO2—C1-C6 alkyl, CO-aryl, SO2-aryl, CO—C1-C4 alkylene-aryl, SO2—C1-C4 alkylene-aryl, SO-aryl, CONH2, CONH—C1-C6 alkyl, SO2NH—C1-C6 alkyl, CON—(C1-C6 alkyl)2, SO2N—(C1-C6 alkyl)2, NH—SO2—C1-C6 alkyl, or NH—CO—C1-C6 alkyl;and/or optionally, preferably with the condition that when W=W1, R, or B is not an optionally substituted N-pyrrolidinyl radical in the 4-position (para position) with respect to the coupling position with Q;
D: is hydrogen or is defined as for radical A, independently of radical A; Q: is a radical of general formula Q1 having the indicesa=0-4 (i.e., an integer equal to 0, 1, 2, 3, or 4)b=0,1 (i.e., an integer equal to 0 or 1)c=0-4 (i.e., an integer equal to 0, 1, 2, 3, or 4)wherein the sum of a, b, and c is at least 1, and 2, 3, 4, and no greater than 5, and is equal to 0, 1, 2, 3, 4, or 5 for the case; X=N, Y=CR4, Z=CR6; RQ1, RQ2, RQ3, RQ4 independently stand for:
hydrogen, halogen, OH, farin each case optionally substituted C1-C6 alkyl, C1-C6 alkenyl, C1-C6 alkylene-C3-C7 cycloalkyl, C3-C7 cycloalkyl, aryl, C1-C4 alkylene-aryl, hetaryl, or C1-C4 alkylene-hetaryl, orin each case two radicals RQ1 and RQ2 or RQ3 and RQ4 independently form together with the respective C atom a 3- to 7-membered, in each case optionally substituted, saturated or unsaturated carbocycle or heterocycle, wherein the heterocycle may contain one, two, or three heteroatoms selected from the group comprising O, N, and/or S; VQ: is in each case optionally substituted —CO—, —CO—NRQ5—, —NRQ5—CO—, —O—, —S—, −SO—, —SO2—, —SO2—NRQ5—, —NRQ5—SO2—, —CS—, —CS—NRQ5—, —NRQ5—CS—, —CS—O—, —CO—O—, —O—CO—, —O—, ethynylene, —C(═CRQ6RQ7)—, —CRQ6═CRQ7—, —NRq5—CO—NRQ5*—, —O—CO—NRQ5—, or —NRQ5—; RQ5, RQ5* independently stand for:
hydrogen orin each case optionally substituted C1-C6 alkyl, C1-C6 alkylene-O—C1-C6 alkyl, C2-C6 alkyenyl, C3-C12 alkynyl, CO—C1-C6 alkyl, CO—O—C1-C6 alkyl, SO2—C1-C6 alkyl, C3-C7 cycloalkyl, aryl, C1-C4 alkylene-aryl, CO—O—C1-C4 alkylene-aryl, CO—C1-C4 alkylene-aryl, CO-aryl, SO2-aryl, hetaryl, CO-hetaryl, or SO2—C1-C4 alkylene-aryl; RQ6, RQ7 independently stand for:
Hydrogen, OH, orin each case optionally substituted C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkylene-C3-C7 cycloalkyl, C3-C7 cycloalkyl, aryl, C1-C4 alkylene-aryl, hetaryl, or C1-C4 alkylene-hetaryl; R1, R2 independently stand for:
hydrogen, OH, CN, orin each case optionally substituted C1-C6 alkyl, O—C1-C6 alkyl, C1-C6 alkylene-O—C1-C6 alkyl, C5-C6 cycloalkyl, O—C3-C7 cycloalkyl, aryl, hetaryl, C1-C4 alkylene-aryl, C1-C4 alkylene-hetaryl, O-aryl, O—C1-C4 alkylene-aryl, O-hetaryl, O—C1-C4 alkylene-hetaryl, CO—C1-C6 alkyl, CO-aryl, CO-hetaryl, CO—C1-C4 alkylene-aryl, CO—C1-C4 alkylene-hetaryl, CO—O—C1-C6 alkyl, CO—O-aryl, CO—O-hetaryl, CO—O—C1-C4 alkylene-aryl, SO2—C1-C6 alkyl, SO2-aryl, SO2-hetaryl, SO2C1-C4 alkylene-aryl, OCO—C1-C6 alkyl, OCO-aryl, OCO-hetaryl, OCO—C1-C4 alkylene-aryl, OCO—C1-C4 alkylene-hetaryl, SO2—C1-C6 alkyl, SO2-aryl, SO2-hetaryl, or SO2—C1-C4 alkylene-aryl, orR1 and R2 to with the nitrogen form a 5- to 7-membered saturated or unsaturated heterocycle optionally substituted in each case, which may contain one, two, or three. further heteroatoms, which may be inherent or the same, from the group O, N, S, wherein in each case two radicals substituted on this carbocycle or heterocycle together may optionally form a 3- to 7-membered anellated, saturated, unsaturated, or aromatic carbocycle or heterocycle which is optionally substituted in each case, wherein the heterocycle may contain up to three heteroatoms, which may be different or the same, selected from the group comprising O, N, and S, and wherein the cyclic compound that is formed may optionally be substituted; R3 is a free electron pair or hydrogen; X, Y, Z in each case have the following meanings:
X=N, Y=CR4, Z=CR6, orX=C, Y=NR6, Z=CR6, orX=N, Y=CR4, Z=NR7, orX=N, Y=N, Z=CR6, orX=N, Y=CR6, Z=N; R4, R6 in each case independently stand for a radical, selected from groups 1.), 3.), 4.) 5.), or 6.), which may be the same or different, and R5, R7 in each case in stand for a radical selected from groups 2.). 3.), 4.), or 5.), which may be the same or different; 1.) Hydrogen, NO2, NH2, CN, CF3, CHF2, OCF3, OCHF2, COOH, O—CH2—COOH, halogen, or
in each case optionally substituted C1-C10 alkyl, C2-C10 alkyenyl, C2-C10 alkynyl, C3-C7 cycloalkyl, C1-C6 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-aryl, C1-C4 alkylene-hetaryl, C1-C6 alkylene-O—C1-C6 alkyl, C1-C6 alkylene-O-aryl, COO—C1-C6 alkyl, or C1-C4 alkylene-COO—C1-C6 alkyl, or in each case optionally substituted O—RZ,Y4, S—RZ,Y4, NRZ,Y6RZ,Y7, CO—ORZ,Y5, CO—RZ,Y5, NRZ,Y7—CO—O—RZ,Y5, O—CH2—COO—RZ,Y5, NRZ,Y7—CO—RZ,Y5, SO2—RZ,Y5, SO—RZ,Y5, NRZ,Y7—SO2—RZ,Y5, SO2NH2, CONH2, SO2—NRZ,Y6RZ,Y7, or CO—NRZ,Y6RZ,Y7; 2.) A free electron pair or hydrogen, CH2—CF3, CH2—CHF2, in each case optionally substituted C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C7 cycloalkyl, C1-C6 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-aryl, C1-C4 alkylene-hetaryl, C1-C6 alkylene-O—C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkylene-O-aryl, COO—C1-C6 alkyl, or C1-C4 alkylene-COO—C1-C6 alkyl, or in each case optionally substituted CO—O—RZ,Y5, CO—RZ,Y5, SO2—RZ,Y5, SO2—RZ,Y5, SO2NH2, CONH2, SO2—NRZ,Y6RZ,Y5, or CO—NRZ,Y6RZ,Y7; 3.) Phenyl, 1-naphthyl, or 2-naphthyl, which in each case are or may be substituted with one, two, or three radicals selected from RZ,Y1, RZ,Y2 and RZ,Y3, wherein RZ,Y1, RZ,Y2, and RZ,Y3 (in each case, independently represent a substituent from the following group:
Hydrogen, NO2, NH2, OH, CN, CF CHF2, OCF3, OCHF2, COOH, O—CH2—COON, SH, halogen, orin catch case optionally substituted aryl, hetaryl heterocycloalkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C1-C4 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-heterocycloalkyl, C1-C4 alkylene-aryl, or C1-C4 alkylene-hetaryl, or in each case optionally substitutedO—RZ,Y4, S—RZ,Y4, NRZ,Y6RZ,Y7, CO—ORZ,Y5, NRZ,Y7—CO—O—RZ,Y5, O—CH2—COO—RZ,Y5, NRZ,Y7—CO—RZ,Y5, NRZ,Y7—CO—NRZ,Y5, SO2—RZ,Y5, NRZ,Y7—SO2—RZ,Y5, NRZ,Y7—SO2—NZ,Y5, SO2NH2, CONH2, SO2—NRZ,Y6RZ,Y7, or CO—NRZ,Y6RZ,Y7; orin each case two of the radicals selected from the group comprising RZ,Y1, RZ,Y2, or RZ,Y3 form, together with the ring atoms bearing these substituents, a 3- to 7-membered saturated or unsaturated carbocycle which in each case is optionally substituted, or a saturated or unsaturated 3- to 7-membered heterocycle which in each case is optionally substituted and which may contain one, two, or three further heteroatoms, which may be different or the same, selected From the group comprising O, N, and S, wherein optionally in each case two radicals substituted on this carbocycle or heterocycle together may form a 3- to 7-membered, anellated, saturated, unsaturated, or aromatic carbocycle, or heterocycle, wherein the heterocycle may contain one, two, or three, heteroatoms, which may be different: or the same, comprising O, N, and S, and wherein the cyclic compound thus; formed may optionally be substituted, and/or a further 3- to 7-membered, optionally substituted cyclic compound may be condensed thereon; RZ,Y4 is in each case optionally substituted C2-C6 alkenyl, C4-C6 alkynyl, C1-C4 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-heterocycloalkyl, heterocycloalkyl, C1-C4 alkylene-hetaryl, hetaryl, C1-C4 alkylene-aryl, aryl, or
C1-C6 alkyl, which in each case is optionally substituted with a substituent selected from the group comprising halogen, NO2, NH2, OH, CN, CF3CHF2, OCF3, OCHF2, optionally substituted NH—(C1-C6 alkyl), or optionally substituted N(C1-C6 alkyl)2; RZ,Y5 is in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C1-C4 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-heterocycloalkyl, heterocycloalkyl, or C1-C6 alkylene-O—C1-C6 alkyl, dioxymethylenephenyl, benzofuranyl, dihydrobenzofuranyl, or indanyl, or aryl or hetaryl which in each case is optionally singly, doubly, or triply substituted with substituents independently selected from the group comprising halogen, NO2, NH2, OH, CN, CF3, CHF2, OCF3, OCHF2, optionally substituted NH—(C1-C6 alkyl) or optionally substituted N(C1-C6 alkyl)2, and COOH, O—CH2—COOH, SH, or in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C1-C4 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4 alkylene-hetaryl, or C1-C4 alkylene-aryl, or in each case optionally substituted
O—RA1, CO—RA1, S—RA1, SO—RA1, CO—O—RA1, NRA4—CO—O—RA1, O—CH2—COO—RA1, NRA2RA3, CONH2, SO2NH2, NRA4—CO—RA1, SO2—RA1, NRA4—SO2—RA1, SO2—NRZ2RA3, or CO—NRA2, RA3, RZ,Y6 is hydrogen, or
in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C1-C4 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C6 alkylene-O—C1-C6 alkyl, CO—C1-C6 alkyl, C1-C4 alkylene-aryl, C1-C4 alkylene-hetaryl, CO-aryl, CO-hetaryl, CO—C1-C4 alkylene-aryl, CO—C1-C4 alkylene-hetaryl, CO—O—C1-C6 alkyl, CO—O-aryl, CO—O—C1-C4 alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4 alkylene-hetaryl, CO—O—C1-C4 alkylene-aryl, SO2—C1-C6 alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4 alkylene-aryl, or SO2—C1-C4 alkylene-hetaryl; RZ,Y7 is hydrogen or in each case optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C1-C4 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C6 alkylene-O—C1-C6 alkyl, CO—C1-C6 alkyl, CO-aryl, CO-hetaryl, CO—C1-C4 alkylene-aryl, CO—C1-C4 alkylene-hetaryl, CO—O—C1-C6 alkyl, CO—O-aryl, CO—O—C1-C4 alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4 alkylene-hetaryl, SO2—C1-C6 alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4 alkylene-aryl, or SO2—C1-C4 alkylene-hetaryl;
or the radicals RZ,Y6 and RZ,Y7 together with the nitrogen form a 3- to 7-membered saturated or aromatic heterocycle which is optionally substantiated in each case and which may contain one, two, or three further heteroatoms, which may be different or the same, selected from the group comprising O, N, and S; and in each case two radicals substituted on this heterocycle together may optionally form a 3- to 7-membered anellated, saturated, unsaturated, or aromatic carbocycle or heterocycle, wherein the heterocycle may contain one, two, of three heteroatoms, which may be different or the same selected from the group comprising O, N, and S, and the cyclic compound thus formed mayoptionally be substituted, or a further 3- to 7-membered, optionally substituted cyclic compound may be condensed thereon; 4.) A 5- or 6-membered, in each case optionally substituted, aromatic heterocycle which may contain one, two, or three heteroatoms which may be different or the same, selected from the group comprising O, N, and S, and which in each case may be substituted with RZ,Y1, RZ,Y2, and RZ,Y3, where RZ,Y1, RZ,Y2, and RZ,Y3 independently have the meanings given above under 3.); 5.) A C5-C15 bi- or tricyclic saturated hydrocarbon radical which in each case is optionally substituted; 6.) R4 and R6 together with X and Y form, optionally substituted in each case, a C6-C10-membered saturated, unsaturated, or aromatic carbocycle, preferably a benzo radical, which may be substituted in each case with one, two, or three radicals which in each case are independently selected from RZ,Y8; RZ,Y8: hydrogen, NO2, NH2, OH, CN, CF3, CHF2, OCF3, OCHF2, COOH, O—CH2—COOH, SH, halogen, or
in each case optionally substituted aryl, hetaryl, heterocycloalkyl, C1-C6 alky, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C1-C4 alkylene-C3-C7 cycloalkyl, C1-C4 alkylene-heterocycloalkyl, C1-C4 alkylene-aryl, or C1-C4 alkylene-hetaryl, or in each case optionally substituted O—RZ,Y4, S—RZ,Y4, NRZ,Y6RZ,Y7, CO—ORZ,Y5, NRZ,Y7—CO—O—RZ,Y5, O—CH2—COO—RZ,Y5, NRZ,Y7—CO—RZ,Y5, SO2—RZ,Y5, NRZ,Y7—SO2—RZ,Y5, SO2NH2, CONH2, SO2—NRZ,Y6RZ,Y7, or CO—NRZ,Y5RZ,Y7, optionally preferably with one, two, or three of the conditions selected from the group comprising conditions (i), (ii), and (iii) listed below: (i) with the condition (i) that when R4 and R6 have the meanings given for group 6.), the radicals A, B, Q, RZ1, and RZ2 are defined as follows: A is located in W1 in the 2-position as indicated and stands for NH2, OCF3, OCHF2, O—CH2—COOH, O—C1-C6 alkyl, S—C1-C6 alkyl, or O—RA1, CO—RA1, S—RA1, SO—RA1, SO2—RA1, SO2—NRA2RA3; B is located in W1 in the 6-position and stands for halogen, CN, CF3, —CHF2, OCF3, OCHF2, or in each case optionally substituted C1-C6 alkyl or C2-C6 alkenyl, O—CH2—COO—RZ1, —O—RA1, S—RA1, NRA2RA3, —NRA1—CO—RA1, or —CO—NRA2RA3; NRA4—SO2—RA1; or B together with RQ1 forms one of the radicals—(CH2)3—, —OCH2—O—, —O—(CH2)2—O—, —CH═CH—CH═CH—, —O—(CH2)2—, —(CH2)2—O—; Q is —CRQ1RQ2; RQ1, RQ2 independently stand for:
hydrogen, halogen, optionally substituted C1-C6 alkyl; ii) with the condition (ii) that when W=W1, Rw1 or B is not an optionally substituted N-pyrrolidinyl radical in the 4-position (pare position) with respect to the coupling position with Q; iii) with the condition (iii) that the sum of a, b, and c 1, 2, 3, 4 or 5 when X=N, Y=CR4, Z=CR6. |
