Substituted 4-phenyltetrahydroisoquinolinium salts, process for their preparation, their use as a medicament, and medicament containing them

A compound of the formula I

• 17
• wherein:
• R1, R2, R3 and R4 are independently of one another H, F, Cl, Br, I, CN, NO2, OH, NH2, CaH2a+1, CqqH2qq−1, OCbH2b+1, COOR50, OCOR50, COR50 or Ox—(CH2)y-phenyl;
• wherein
• a and b are independently of one another 1, 2, 3, 4, 5, 6, 7 or 8, wherein the groups CaH2a+1 and OCbH2b+1 independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• qq is 3, 4, 5, 6, 7 or 8, wherein the group CqqH2qq−1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• R50 is H or CcH2c+1,
• c is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group CcH2c+1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• x is zero or 1;
• y is zero, 1, 2, 3 or 4, where the phenyl ring in the group Ox—(CH2)y-phenyl is unsubstituted or substituted by 1-3 independently chosen from F, Cl, Br, CN, NO2, OH, NH2 and CdH2d+1,
• d is 1, 2, 3 or 4, wherein the group CdH2d+1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• or
• R1, R2, R3 and R4 are independently of one another chosen from a heteroaryl with at least one heteroatom chosen from 1, 2, 3 or 4 N atoms, 1 oxygen atom and 1 S atom, present as a ring atom;
• or
• R1, R2, R3 and R4 are independently of one another CONR11R12 or NR11R12;
• wherein
• R11 and R12 are independently of one another H, CeH2e+1, or CrrH2rr−1,
• e is 1, 2, 3, 4, 5, 6, 7 or 8;
• rr is 3, 4, 5, 6, 7, or 8, wherein the groups CeH2e+1 and CrrH2rr−1 independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms and/or one or more CH2 groups are replaced by O or NR13;
• R13 is H or CfH2f+1;
• f is 1, 2, 3 or 4, wherein the group CfH2f+1 is unsubsitituted or substituted where one or more H atoms are replaced by F atoms;
• or
• R13 and a CH2 group of R11 or R12 together with the N atom to which they are bonded form a 5- or 6-membered ring;
• or
• R11 and R12 together with the N atom to which they are bonded form a 5-, 6- or 7-membered ring;
• or
• R11 and R12 are independently of one another COR14, CSR14 or SO2R14;
• wherein
• R14 is CgH2g+1;
• g is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group CgH2g+1 is unsubsitituted or substituted where one or more H atoms are replaced by F atoms, and/or one or more CH2 groups are replaced by O or NR13;
• or
• R1, R2, R3 and R4 are independently of one another —Oh—SOj-R15;
• wherein
• h is zero or 1;
• j is zero, 1 or 2;
• R15 is CkH2k+1, OH, OClH2l+1 or NR17R18;
• k is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group CkH2k+1 is unsubsitituted or substituted where one or more H atoms are replaced by F atoms;
• l is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group OClH2l+1 is unsubsitituted or substituted where one or more H atoms are replaced by F atoms;
• R17 and R18 are independently of one another H or CmH2m+1;
• m is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group CmH2m+1 is unsubstituted or substituted where one or more H atoms is replaced by F atoms and/or one or more CH2 groups are replaced by O, CO, CS or NR19;
• R19 is H or CnH2n+1;
• n is 1, 2, 3 or 4, wherein the group CnH2n+1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• or
• R17 and R18 together with the N atom to which they are bonded form a 5-, 6- or 7-membered ring;
• or
• R19 and a CH2 group of R17 or R18 together with the N atom to which they are bonded form a 5- or 6-membered ring;
• R5 and R6 are independently of one another CpH2p+1, CssH2ss−1, COR20 or SO2R20;
• wherein
• p is 1, 2, 3, 4, 5, 6, 7 or 8;
• ss is 3, 4, 5, 6, 7 or 8;
• R20 is CqH2q+1;
• q is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the groups CpH2p+1, CssH2ss−1 and CqH2q+1 independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms and/or one or more CH2 groups are replaced by O or NR21;
• R21 is H or CrH2r+1;
• r is 1, 2, 3 or 4;
• wherein the group CrH2r+1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• R7 is H, F, Cl, Br, I, CsH2s+1, CddH2dd−1, OH, OCtH2t+1 or OCOR22;
• wherein
• s and t are independently of one another 1, 2, 3, 4, 5, 6, 7 or 8;
• dd is 3, 4, 5, 6, 7 or 8, wherein the groups CsH2s+1, CddH2dd−1 and OCtH2t+1 independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• R22 is CuH2u+1;
• u 1, 2, 3 or 4, wherein the group CuH2u+1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• R8, R9 and R10 are independently of one another —Ov—SOw—R23;
• wherein
• v is zero or 1;
• w is zero, 1 or 2;
• R23 is CnnH2nn+1, CmmH2mm−1, OH, OCppH2pp+1 or NR25R26;
• nn and pp are independently of one another 1, 2, 3, 4, 5, 6, 7 or 8,
• mm is 3, 4, 5, 6, 7 or 8, wherein the groups CnnH2nn+1, CmmH2mm−1 and OCppH2pp+1 independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• R25 and R26 are independently of one another H, CN, CzH2z+1, or CzzH2zz−1;
• z is 1, 2, 3, 4, 5, 6, 7 or 8;
• zz is 3, 4, 5, 6, 7 or 8, wherein the group CzH2z+1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms and,
• wherein the group CzH2z+1, is unsubstituted or substituted where one or more H atoms are replaced by F atoms and/or one or more CH2 groups are replaced by O, CO, CS or NR27;
• R27 is H or CaaH2aa+1;
• aa is 1, 2, 3 or 4, wherein the group CaaH2aa+1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• or
• R27 and a CH2 group of R25 or R26 together with the N atom to which they are bonded form a 5- or 6-membered ring;
• or
• R25 and R26 together with the N atom to which they are bonded form a 5-, 6- or 7-membered ring, or
• R8, R9 and R10 are independently of one another NR32COR30, NR32CSR30 or NR32SObbR30;
• wherein
• R30 is H, CccH2cc+1, CyyH2yy−1, pyrrolidinyl or piperidinyl, wherein the pyrrolidinyl or piperidinyl is unsubstituted or substituted where a CH2 group is replaced by O or NR33;
• R32 and R33 are independently of one another H or ChH2h+1;
• bb is 2 or 3;
• cc is 1, 2, 3, 4, 5, 6, 7 or 8;
• yy is 3, 4, 5, 6, 7 or 8;
• h is 1, 2, 3, 4, 5, 6, 7 or 8,
• wherein the group ChH2h+1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms, and
• wherein the groups CccH2cc+1 and CyyH2yy−1 independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms and/or one or more CH2 groups are replaced by O or NR31;
• R31 is H, CkkH2kk+1, or COR65;
• kk is 1, 2, 3, or 4;
• wherein the group CkkH2kk+1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms,
• R65 is H, or CxxH2xx+1;
• xx is 1, 2, 3 or 4, wherein the group CxxH2xx+1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• or
• R31 together with a CH2 group of R30 and the N atom to which they are jointly bonded forms a 5-, 6- or 7-membered ring;
• or
• R30 is a 5- or 6-membered heteroaryl with at least one hetero atom chosen from 1, 2, 3 or 4 N atoms, 1 S atoms and 1 O atoms
• which is unsubstituted or substituted by up to three substituents chosen from F, Cl, Br, I, CooH2oo+1, and NR70R71;
• R70 and R71 are independently of one another H, CuuH2uu+1 or COR72;
• R72 is H, or CvvH2vv+1;
• oo, uu and vv are independently of one another 1, 2, 3, 4, 5, 6, 7 or 8, wherein the groups CooH2oo+1, CuuH2uu+1 and CvvH2vv+1 independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• or
• R8, R9 and R10 are independently of one another H, F, Cl, Br, I, NO2, CN, OH, NH2, CeeH2ee+1, CwwH2ww−1, OCffH2ff+1, NR40R41, CONR40R41, COOR42, COR42 or OCOR42;
• ee and ff are independently of one another 1, 2, 3, 4, 5, 6, 7 or 8;
• ww is 3, 4, 5, 6, 7 or 8, wherein the groups CeeH2ee+1, CwwH2ww−1 and OCffH2ff+1 independently of one another are unsubstituted or substituted where one or more H atoms are replaced by F atoms;
• R40 and R41 are independently of one another H or CttH2tt+1;
• tt is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group CttH2tt+1 is unsubstituted or substituted where one or more H atoms are replaced by F atoms and/or where one or more CH2 groups are replaced by O or NR44;
• R44 is H or CggH2gg+1;
• gg is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group CggH2gg+1 is unnsubstituted or substituted where one or more H atoms are replaced by F atoms;
• or
• R40 and R41 with the N atom to which they are bonded for a 5- or 6-membered ring;
• R42 is H or ChhH2hh+1;
• hh is 1, 2, 3, 4, 5, 6, 7 or 8, wherein the group ChhH2hh+1 is unnsubstituted or substituted where one or more H atoms are replaced by F atoms;
• Y is chosen from fluorine, chlorine, bromine, iodine, hydroxyl and all anionic forms of pharmacologically acceptable mono-, di- or tricarboxylic acids and sulfonic acids;
• or a pharmaceutically acceptable salt thereof, or a trifluoroacetic acid salt thereof, in any stereoisomeric form, or a mixture of any such compounds in any ratio.