Ortho, meta-substituted bisaryl compounds, processes for...

Details Ortho, meta-substituted bisaryl compounds, processes for... Ortho, meta-substituted bisaryl compounds, processes for...

2001-11-29

2003-08-12

Berch, Mark L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C546S256000, C546S257000, C546S258000, C546S261000, C546S314000, C546S316000, C546S280400, C546S283400, C546S337000, C514S334000, C514S354000, C514S355000, C514S357000

Reexamination Certificate

active

06605625

ABSTRACT:

This application claims the benefit of foreign priority under 35 U.S.C. §119 of German patent application no. 10059418.2-44, filed on Nov. 30, 2000 the contents of which are incorporated by reference herein.
The present invention relates to ortho, meta-substituted bisaryl compounds. Embodiments of the invention include, processes for their preparation, their use as medicaments, and pharmaceutical preparations comprising them. The present invention relates to ortho, meta-substituted bisaryl compounds of the formula I,
in which:
A2, A3, A4, A5, A6, A7 and A8 independently of one another are chosen from nitrogen, CH and CR(5), at least four of these groups being CH;
R(1) is C(O)OR(9), SO
2
R(10), COR(11), C(O)NR(12)R(13) or C(S)NR(12)R(13);
wherein R(9), R(10), R(11)and R(12) independently of one another are chosen from C
x
H
2x
-R(14);
where x is 0, 1, 2, 3 or 4, and
x cannot be 0 if R(14) is OR(15) or SO
2
Me;
R(14) is alkyl having 1, 2, 3, 4, 5 or 6 atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9, 10 or 11 carbon atoms, CF
3
, C
2
F
5
, C
3
F
7
, CH
2
F, CHF
2
, OR(15), SO
2
Me, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl or a substituted or unsubstituted N-containing heteroaromatic having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms,
where the substituted phenyl, substituted naphthyl, substituted biphenylyl, substituted furyl, substituted thienyl and the substituted N-containing heteroaromatic are each independently substituted by 1, 2 or 3 substituents chosen from F, Cl, Br, I, CF
3
, OCF
3
, NO
2
, CN, COOMe, CONH
2
, COMe, NH
2
, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
R(15) is alkyl having 1, 2, 3, 4 or 5 carbon atoms, cycloalkyl having 3, 4, 5 or 6 carbon atoms, CF
3
, substituted phenyl or unsubstituted phenyl,
wherein the substituted phenyl is substituted by 1, 2 or 3 substituents chosen from F, Cl, Br, I, CF
3
, NO
2
, CN, COOMe, CONH
2
, COMe, NH
2
, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino; and
R(13) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or CF
3
;
R(2) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or CF
3
;
R(3) is C
y
H
2y
—R(16);
where y is 0, 1, 2, 3 or 4, and
y cannot be 0 if R(16) is OR(17) or SO
2
Me;
R(16) is alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9, 10 or 11 carbon atoms, CF
3
, C
2
F
5
, C
3
F
7
, CH
2
F, CHF
2
, OR(17), SO
2
Me, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl or a substituted or unsubstituted N-containing heteroaromatic having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms,
where the substituted phenyl, substituted naphthyl, substituted furyl, substituted thienyl and the substituted N-containing heteroaromatic are each independently substituted by 1, 2 or 3 substituents chosen from F, Cl, Br, I, CF
3
, OCF
3
, NO
2
, CN, COOMe, CONH
2
, COMe, NH
2
, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino; and
R(17) is hydrogen, alkyl having 1, 2, 3, 4 or 5 carbon atoms, cycloalkyl having 3, 4, 5 or 6 carbon atoms, CF
3
, substituted phenyl, unsubstituted phenyl, substituted 2-, 3- or 4-pyridyl, or unsubstituted 2-, 3- or 4-pyridyl,
where the substituted phenyl and substituted 2-, 3- or 4-pyridyl are each independently substituted by 1, 2 or 3 substituents chosen from F, Cl, Br, I, CF
3
, OCF
3
, NO
2
, CN, COOMe, CONH
2
, COMe, NH
2
, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino; or
R(3) is CHR(18)R(19);
where R(18) is hydrogen or C
z
H
2z
—R(16), where R(16) is defined as indicated above;
z is 0, 1, 2 or 3;
R(19) is COOH, CONH
2
, CONR(20)R(21), COOR(22) or CH
2
OH;
R(20) is hydrogen, alkyl having 1, 2, 3, 4 or 5 carbon atoms, C
v
H
2v
—CF
3
, substituted C
w
H
2w
— phenyl or unsubstituted C
w
H
2w
— phenyl,
where the phenyl ring of the substituted C
w
H
2w
— phenyl is substituted by 1, 2 or 3 substituents chosen from F, Cl, Br, I, CF
3
, NO
2
, CN, COOMe, CONH
2
, COMe, NH
2
, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
v is 0, 1, 2 or 3;
w is 0, 1, 2 or 3;
R(21) is hydrogen or alkyl having 1, 2, 3, 4 or 5 carbon atoms; and
R(22) is alkyl having 1, 2, 3, 4 or 5 carbon atoms;
R(4) is hydrogen, alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms or CF
3
; or
R(3) and R(4) together are a chain of 4 or 5 methylene groups, of which one methylene group can be replaced by —O—, —S—, —NH—, —N(methyl)— or —N(benzyl)—;
R(5) is F, Cl, Br, I, CF
3
, NO
2
, CN, COOMe, CONH
2
, COMe, NH
2
, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl or methylsulfonylamino, where in the case that more than one of the radicals A1 to A8 have the meaning CR(5), the radicals R(5) are defined independently of one another;
R(30) and R(31) independently of one another are hydrogen or alkyl having 1, 2 or 3 carbon atoms; or
R(30) and R(31) together are a chain of 2 methylene groups
and their pharmaceutically acceptable salts.
In one embodiment, the compounds of formula I are those in which:
A2, A3, A4, A5, A6, A7 and A8 independently of one another are chosen from nitrogen, CH or CR(5), at least 4 of these groups being CH;
R(1) is C(O)OR(9), SO
2
R(10), COR(11) or C(O)NR(12)R(13)
where R(9), R(10), R(11) and R(12) independently of one another are C
x
H
2x
—R(14);
where x is 0, 1, 2, 3 or 4; and
x cannot be 0 if R(14) is OR(15);
R(14) is alkyl having 1, 2, 3 or 4 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8 or 9 carbon atoms, CF
3
, OR(15), substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl or a substituted or unsubstituted N-containing heteroaromatic having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms,
where substituted phenyl, substituted naphthyl, substituted biphenylyl, substituted furyl, substituted thienyl and the substituted N-containing heteroaromatic are each independently substituted by 1, 2 or 3 substituents chosen from F, Cl, Br, I, CF
3
, OCF
3
, NO
2
, CN, COOMe, CONH
2
, COMe, NH
2
, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
R(15) is alkyl having 1, 2, 3, 4 or 5carbon atoms, cycloalkyl having 3, 4, 5 or 6 carbon atoms, CF
3
, substituted phenyl or unsubstituted phenyl,
wherein the substituted phenyl is substituted by 1, 2 or 3 substituents chosen from F, Cl, Br, I, CF
3
, NO
2
, CN, COOMe, CONH
2
, COMe, NH
2
, OH, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
R(13) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or CF
3
;
R(2) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or CF
3
;
R(3) is C
y
H
2y
—R(16);
where y is 0, 1, 2, 3 or 4, and
y cannot be 0 if R(16) is OR(17) or SO
2
Me;
R(16) is alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9, carbon atoms, CF
3
, OR(17), SO
2
Me, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl or a substituted or unsubstituted N-containing heteroaromatic having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms,
where the substituted phenyl, substituted naphthyl, substituted furyl, substituted thienyl and the substituted N-containing heteroaromatic are each independently su

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