Ortho, ortho-substituted nitrogen-containing bisaryl...

Details Ortho, ortho-substituted nitrogen-containing bisaryl... Ortho, ortho-substituted nitrogen-containing bisaryl...

2001-12-05

2004-09-21

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S344000, C514S256000, C514S352000, C514S277000, C514S336000, C514S350000, C514S155000, C514S357000, C546S257000, C546S286000, C546S289000, C546S307000, C546S315000, C546S340000, C544S224000, C544S238000, C544S242000, C544S323000, C544S336000, C544S405000

Reexamination Certificate

active

06794377

ABSTRACT:

This application claims the benefit of foreign priority under 35 U.S.C. §119 of German patent application no. 10060807.8-44, filed on Dec. 7, 2000 the contents of which are incorporated by reference herein.
The present invention relates to ortho, ortho-substituted nitrogen-containing 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, ortho-substituted nitrogen-containing bisaryl compounds of the formula I,
in which:
A1, A2, A3, A4, A5, A6, A7 and A8
independently of one another are chosen from nitrogen, CH and CR(5), at least one of these groups being nitrogen and at least 4 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 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 8 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, CH
3
, OCF
3
, NO
2
, CN, COOMe, CONH
2
, COMe, NH
2
, CH, 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, CH
3
, NO
2
, CN, COOMe, CONH
2
, COMe, NH
2
, CH, 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 CH
3
;
R(2) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or CH
3
;
R(3) is C
y
H
2y
—R(16);
where y is 0, 1, 2, 3or 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
, OCF
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
, CH, 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 COCH, 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 independently of one another 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 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 oxygen or a chain of 2 methylene groups
and their pharmaceutically acceptable salts.
In one embodiment, the compounds of formula 1 are those in which:
A1, A2, A3, A4, A5, A6, A7 and A8
independently of one another are chosen from nitrogen, CH and CR(5), at least one of these groups being nitrogen and 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) 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 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;
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 it 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

Affiliated with

Also associated with

Rating

Ortho, ortho-substituted nitrogen-containing bisaryl... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Ortho, ortho-substituted nitrogen-containing bisaryl..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Ortho, ortho-substituted nitrogen-containing bisaryl... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3260178