Patent ID: 8188282
Filing Date: 2012-05-29
Classification: C07D

Abstract:
1. A process for preparing a compound of formula I or a stereoisomeric form of the compound of formula I, or a mixture of these forms in any ratio, or a physiologically tolerated salt of a compound of formula I, wherein A1, A2, A3, A4 are each carbon to form together with the two carbon atoms in formula I a stable aromatic ring; Q is —(C 1 -C 6 )-alkylene, wherein the alkylene is unsubstituted or mono-, di- or trisubstituted independently of one another by R14; —(C 3 -C 8 )-cycloalkyl, wherein the cycloalkyl is unsubstituted or mono-, di- or trisubstituted independently of one another by R14; —(C 6 -C 14 )-aryl, wherein the aryl is unsubstituted or mono-, di-, tri- or four times substituted independently of one another by R13; or —(C 4 -C 14 )-heteroaryl, wherein the heteroaryl is unsubstituted or mono-, di-, tri- or four times substituted independently of one another by R13; J is —(C 1 -C 6 )-alkylene, wherein the alkylene is unsubstituted or mono-, di- or trisubstituted independently of one another by R14; —(C 3 -C 8 )-cycloalkyl, wherein the cycloalkyl is unsubstituted or mono-, di- or trisubstituted independently of one another by R14; —(C 6 -C 14 )-aryl, wherein the aryl is unsubstituted or mono-, di-, tri- or four times substituted independently of one another by R13; or —(C 4 -C 14 )-heteroaryl, wherein the heteroaryl is unsubstituted or mono-, di-, tri- or four times substituted independently of one another by R13; R0, R1, R2, R3, R4 and R5 are independent of one another identical or different and are a) hydrogen atom, b) —(C c) halogen, d) phenyloxy-, wherein the phenyloxy is unsubstituted or substituted one to three times by R13, e) —(C f) —N(R10)-(C g) —(C h) —(C i) —(C j) a 3- to 7-membered cyclic residue, containing up to 1, 2, 3 or 4 heteroatoms chosen from nitrogen, sulfur or oxygen, wherein said cyclic residue is unsubstituted or mono-, di-, tri- or four times substituted independently of one another by R13, k) —O—CF l) —O—(C m) —NO n) —CN, o) —OH, p) —C(O)—R10, q) —C(O)—O—R11, r) —C(O)—N(R11)-R12, s) —N(R11)-R12, t) —N(R10)-SO v) —S—R10, w) —SO x) —SO y) at least one of R1, R2, R3 or R4 are absent in case one or more of A1, A2, A3 or A4 is a nitrogen atom, or R1 and R2, R2 and R3 or R3 and R4 form together with the atoms which they are attached to a 5- or 8-membered ring, containing 0, 1, 2, 3 or 4 heteroatoms chosen from nitrogen, sulfur or oxygen, wherein said ring is unsubstituted or substituted one, two, three or four times by R14, R10 is hydrogen atom, —(C 1 -C 3 )-fluoroalkyl or —(C 1 -C 6 )-alkyl, R11 and R12 are independently of one another identical or different and are a) hydrogen atom, b) —(C c) —(C d) —(C R13 is halogen, —NO 2 , —CN, ═O, —OH, —(C 1 -C 8 )-alkyl, —(C 1 -C 8 )-alkoxy, —CF 3 , phenyloxy-, —C(O)—O—R17, —C(O)—N—(R17)-R18, —N(R17)-R18, —C(O)—R10, —N(R10)-SO 2 —R10, —S—R10, —SO n —R10, wherein n is 1 or 2, —SO 2 —N(R17)-R18, —(C 6 -C 14 )-aryl, wherein the aryl is unsubstituted or mono-, di- or trisubstituted independently of one another by R14, —(C 4 -C 14 )-heteroaryl, wherein the heteroaryl is unsubstituted or mono-, di- or trisubstituted independently of one another by R14, —(C 3 -C 8 )-cycloalkyl, wherein the cycloalkyl is unsubstituted or mono-, di- or trisubstituted independently of one another by R14, or a 3- to 7-membered cyclic residue, containing up to 1, 2, 3 or 4 heteroatoms chosen from nitrogen, sulfur or oxygen, wherein said cyclic residue is unsubstituted or mono-, di- or trisubstituted independently of one another by R14, R14 is halogen, —OH, ═O, —CN, —CF 3 , —(C 1 -C 8 )-alkyl, —(C 1 -C 4 )-alkoxy, —NO 2 , —C(O)—OH, —NH 2 , —C(O)—O—(C 1 -C 4 )-alkyl, —(C 1 -C 8 )-alkylsulfonyl, —C(O)—NH—(C 1 -C 8 )-alkyl, —C(O)—N [(C 1 -C 8 )-alkyl] 2 , —C(O)—NH 2 , —S—R10, —N(R10)-C(O)—NH—(C 1 -C 8 )-alkyl, or —N(R10)-C(O)—N[(C 1 -C 8 )-alkyl] 2 , R17 and R18 are independently of one another identical or different and are a) hydrogen atom, b) —(C c) —(C d) —(C said process comprising reacting a compound of formula II wherein R1, R2, R3, R4, A1, A2, A3 and A4 are as defined in formula I and X is Cl, Br, I, triflate or nonaflate, with a compound of formula III wherein Q, J, R0 and R5 are as defined in formula I, in the presence of a palladium catalyst, a base, a ligand and an aprotic solvent to give a compound of formula IV and converting the compound of formula IV into a compound of formula I in the presence of a reducing reagent and a second solvent, and optionally converting the compound of formula I to a physiologically tolerated salt thereof.