Further substituted triazolo quinoxaline derivatives
The present invention relates to compounds according to general formula (I) which act as modulators of the glucocorticoid receptor and can be used in the treatment and/or prophylaxis of disorders which are at least partially mediated by the glucocorticoid receptor.
1. A compound according to general formula (I),
wherein
R 1 represents H; C 1-10 -alkyl; C 3-10 -cycloalkyl; 3 to 7 membered heterocycloalkyl; aryl; or 5 or 6-membered heteroaryl;
wherein C 3-10 -cycloalkyl, 3 to 7 membered heterocycloalkyl, aryl and 5 or 6-membered heteroaryl can optionally be bridged via C 1-6 -alkylene;
R 2 represents H; F; Cl; Br; I; CN; C 1-10 -alkyl; C 3-10 -cycloalkyl; O—C 1-10 -alkyl; N(H)(C 1-10 -alkyl), N(C 1-10 -alkyl) 2 ; C(O)—C 1-10 -alkyl; C(O)—O—C 1-10 -alkyl; C(O)—NH 2 ; C(O)—N(H)(C 1-10 -alkyl); C(O)—N(C 1-10 -alkyl) 2 ; O—C 3-10 -cycloalkyl; N(H)(C 3-10 -cycloalkyl), N(C 1-10 -alkyl)(C 3-10 -cycloalkyl); C(O)—C 3-10 -cycloalkyl; C(O)—O—C 3-10 -cycloalkyl; C(O)—N(H)(C 3-10 -cycloalkyl) or C(O)—N(C 1-10 -alkyl)(C 3-10 -cycloalkyl);
wherein C 3-10 -cycloalkyl can optionally be bridged via C 1-6 -alkylene;
R 3 represents H; F; Cl; Br; I; CN; C 1-10 -alkyl; C 3-10 -cycloalkyl; O—C 1-10 -alkyl; N(H)(C 1-10 -alkyl); N(C 1-10 -alkyl) 2 ; C(O)—C 1-10 -alkyl; C(O)—O—C 1-10 -alkyl; C(O)—NH 2 ; C(O)—N(H)(C 1-10 -alkyl); C(O)—N(C 1-10 -alkyl) 2 ; O—C 3-10 -cycloalkyl; N(H)(C 3-10 -cycloalkyl), N(C 1-10 -alkyl)(C 3-10 -cycloalkyl); C(O)—C 3-10 -cycloalkyl; C(O)—O—C 3-10 -cycloalkyl; C(O)—N(H)(C 3-10 -cycloalkyl) or C(O)—N(C 1-10 -alkyl)(C 3-10 -cycloalkyl);
wherein C 3-10 -cycloalkyl can optionally be bridged via C 1-6 -alkylene;
R 4 represents F or Cl;
R 5 and R 6 represent independently from one another H or unsubstituted C 1-4 -alkyl;
X represents N or NR′;
Z represents N, NR′ or CR 9 ;
with the proviso that
when X represents NR′, Z represents N or CR 9 ;
when X represents N, Z represents NR′;
R 7 represents H or L-R 8 ; wherein
L represents a bond; S(O); S(O) 2 ; C 1-6 -alkylene; C(O); C 1-6 -alkylene-C(O); C(O)—O; C 1-6 -alkylene-C(O)—O; C 1-6 -alkylene-N(H)—C(O); C 1-6 -alkylene-N(C 1-10 -alkyl)-C(O); C 1-6 -alkylene-N(H)—C(O)—O; C 1-6 -alkylene-N(C 1-10 -alkyl)-C(O)—O; O; NH or N(C 1-10 -alkyl);
R 8 represents C 1-10 -alkyl; C 3-10 -cycloalkyl or 3 to 7 membered heterocycloalkyl; wherein C 3-10 -cycloalkyl and 3 to 7 membered heterocycloalkyl can optionally be bridged via C 1-6 -alkylene;
R 9 and R 10 represent independently from one another H; F; Cl; Br; I; CN; C 1-10 -alkyl; C 3-10 -cycloalkyl; 3 to 7 membered heterocycloalkyl; S(O)—(C 1-10 -alkyl); S(O)—(C 3-10 -cycloalkyl); S(O)-(3 to 7-membered heterocycloalkyl); S(O) 2 —(C 1-10 -alkyl); S(O) 2 —(C 3-10 -cycloalkyl); S(O) 2 -(3 to 7-membered heterocycloalkyl); P(O)—(C 1-10 -alkyl) 2 ; P(O)(C 1-10 -alkyl)(C 3-10 -cycloalkyl); P(O)(C 1-10 -alkyl)(3 to 7-membered heterocycloalkyl); P(O)—(O—C 1-10 -alkyl) 2 ; P(O)(O—C 1-10 -alkyl)(O—C 3-10 -cycloalkyl); P(O)(O—C 1-10 -alkyl)(O-(3 to 7-membered heterocycloalkyl)); O—C 1-10 -alkyl; S—C 1-10 -alkyl; N(H)(C 1-10 -alkyl), N(C 1-10 -alkyl) 2 ; C(O)—C 1-10 -alkyl; C(O)—O—C 1-10 -alkyl; C(O)—NH 2 ; C(O)—N(H)(C 1-10 -alkyl); C(O)—N(C 1-10 -alkyl) 2 ; O—C 3-10 -cycloalkyl; N(H)(C 3-10 -cycloalkyl), N(C 1-10 -alkyl)(C 3-10 -cycloalkyl); C(O)—C 3-10 -cycloalkyl; C(O)—O—C 3-10 -cycloalkyl; C(O)—N(H)(C 3-10 -cycloalkyl); C(O)—N(C 1-10 -alkyl)(C 3-10 -cycloalkyl); O-3 to 7-membered heterocycloalkyl; N(H)(3 to 7-membered heterocycloalkyl), N(C 1-10 -alkyl)(3 to 7-membered heterocycloalkyl); C(O)-3 to 7-membered heterocycloalkyl; C(O)—O-(3 to 7-membered heterocycloalkyl); C(O)—N(H)(3 to 7-membered heterocycloalkyl) or C(O)—N(C 1-10 -alkyl)(3 to 7-membered heterocycloalkyl); wherein C 3-10 -cycloalkyl and 3 to 7 membered heterocycloalkyl can optionally be bridged via C 1-6 -alkylene;
R 11 represents F; Cl; Br; I; CN; C 1-10 -alkyl; O—C 1-10 -alkyl; NO 2 ; OH, NH 2 ; C 3-10 -cycloalkyl; 3 to 7-membered heterocycloalkyl; S(O)—(C 1-10 -alkyl); S(O)—(C 3-10 -cycloalkyl); S(O)-(3 to 7-membered heterocycloalkyl); S(O) 2 —(C 1-10 -alkyl); S(O) 2 —(C 3-10 -cycloalkyl); S(O) 2 -(3 to 7-membered heterocycloalkyl); P(O)—(C 1-10 -alkyl) 2 ; P(O)(C 1-10 -alkyl)(C 3-10 -cycloalkyl); P(O)(C 1-10 -alkyl)(3 to 7-membered heterocycloalkyl); P(O)—(O—C 1-10 -alkyl) 2 ; P(O)(O—C 1-10 -alkyl)(O—C 3-10 -cycloalkyl); P(O)(O—C 1-10 -alkyl)(O-(3 to 7-membered heterocycloalkyl)); N(H)(C 1-10 -alkyl), N(C 1-10 -alkyl) 2 ; C(O)—C 1-10 -alkyl; C(O)—O—C 1-10 -alkyl; C(O)—NH 2 ; C(O)—N(H)(C 1-10 -alkyl); C(O)—N(C 1-10 -alkyl) 2 ; O—C 3-10 -cycloalkyl; N(H)(C 3-10 -cycloalkyl), N(C 1-10 -alkyl)(C 3-10 -cycloalkyl); C(O)—C 3-10 -cycloalkyl; C(O)—O—C 3-10 -cycloalkyl; C(O)—N(H)(C 3-10 -cycloalkyl); C(O)—N(C 1-10 -alkyl)(C 3-10 -cycloalkyl); O-3 to 7-membered heterocycloalkyl; N(H)(3 to 7-membered heterocycloalkyl), N(C 1-10 -alkyl)(3 to 7-membered heterocycloalkyl); C(O)-3 to 7-membered heterocycloalkyl; C(O)—O-(3 to 7-membered heterocycloalkyl); C(O)—N(H)(3 to 7-membered heterocycloalkyl) or C(O)—N(C 1-10 -alkyl)(3 to 7-membered heterocycloalkyl); wherein C 3-10 -cycloalkyl and 3 to 7 membered heterocycloalkyl can optionally be bridged via C 1-6 -alkylene;
n represents 0, 1, 2 or 3;
wherein C 1-10 -alkyl, C 1-4 -alkyl and C 1-6 -alkylene in each case independently from one another is linear or branched, saturated or unsaturated;
wherein C 1-10 -alkyl, C 1-6 -alkylene, C 3-10 -cycloalkyl and 3 to 7 membered heterocycloalkyl in each case independently from one another are unsubstituted or mono- or polysubstituted with one or more substituents selected from F; Cl; Br; I; CN; C 1-6 -alkyl; CF 3 ; CF 2 H; CFH 2 ; CF 2 Cl; CFCl 2 ; C(O)—C 1-6 -alkyl; C(O)—OH; C(O)—OC 1-6 -alkyl; C(O)—NH 2 ; C(O)—N(H)(C 1-6 -alkyl); C(O)—N(C 1-6 -alkyl) 2 ; OH; ═O; OCF 3 ; OCF 2 H; OCFH 2 ; OCF 2 Cl; OCFCl 2 ; O—C 1-6 -alkyl; O—C(O)—C 1-6 -alkyl; O—C(O)—O—C 1-6 -alkyl; O—(CO)—N(H)(C 1-6 -alkyl); O—C(O)—N(C 1-6 -alkyl) 2 ; O—S(O) 2 —NH 2 ; O—S(O) 2 —N(H)(C 1-6 -alkyl); O—S(O) 2 —N(C 1-6 -alkyl) 2 ; NH 2 ; N(H)(C 1-6 -alkyl); N(C 1-6 -alkyl) 2 ; N(H)—C(O)—C 1-6 -alkyl; N(H)—C(O)—O—C 1-6 -alkyl; N(H)—C(O)—NH 2 ; N(H)—C(O)—N(H)(C 1-6 -alkyl); N(H)—C(O)—N(C 1-6 -alkyl) 2 ; N(C 1-6 -alkyl)-C(O)—C 1-6 -alkyl; N(C 1-6 -alkyl)-C(O)—O—C 1-6 -alkyl; N(C 1-6 -alkyl)-C(O)—NH 2 ; N(C 1-6 -alkyl)-C(O)—N(H)(C 1-6 -alkyl); N(C 1-6 -alkyl)-C(O)—N(C 1-6 -alkyl) 2 ; N(H)—S(O) 2 OH; N(H)—S(O) 2 —C 1-6 -alkyl; N(H)—S(O) 2 —O—C 1-6 -alkyl; N(H)—S(O) 2 —NH 2 ; N(H)—S(O) 2 —N(H)(C 1-6 -alkyl); N(H)—S(O) 2 N(C 1-6 -alkyl) 2 ; N(C 1-6 -alkyl)-S(O) 2-0 H; N(C 1-6 -alkyl)-S(O) 2 —C 1-6 -alkyl; N(C 1-6 -alkyl)-S(O) 2 —O—C 1-6 -alkyl; N(C 1-6 -alkyl)-S(O) 2 —NH 2 ; N(C 1-6 -alkyl)-S(O) 2 —N(H)(C 1-6 -alkyl); N(C 1-6 -alkyl)-S(O) 2 —N(C 1-6 -alkyl) 2 ; SCF 3 ; SCF 2 H; SCFH 2 ; S—C 1-6 -alkyl; S(O)—C 1-6 -alkyl; S(O) 2 —C 1-6 -alkyl; S(O) 2 —OH; S(O) 2 —O—C 1-6 -alkyl; S(O) 2 —NH 2 ; S(O) 2 —N(H)(C 1-6 -alkyl); S(O) 2 —N(C 1-6 -alkyl) 2 ; C 3-6 -cycloalkyl; 3 to 6-membered heterocycloalkyl; phenyl; 5 or 6-membered heteroaryl; O—C 3-6 -cycloalkyl; O-(3 to 6-membered heterocycloalkyl); O-phenyl; O-(5 or 6-membered heteroaryl); C(O)—C 3-6 -cycloalkyl; C(O)-(3 to 6-membered heterocycloalkyl); C(O)-phenyl; C(O)-(5 or 6-membered heteroaryl); S(O) 2 —(C 3-6 -cycloalkyl); S(O) 2 -(3 to 6-membered heterocycloalkyl); S(O) 2 -phenyl or S(O) 2 -(5 or 6-membered heteroaryl);
wherein aryl and 5 or 6-membered heteroaryl in each case independently from one another are unsubstituted or mono- or polysubstituted with one or more substituents selected from F; Cl; Br; I; CN; C 1-6 -alkyl; CF 3 ; CF 2 H; CFH 2 ; CF 2 Cl; CFCl 2 ; C 1-4 -alkylene-CF 3 ; C 1-4 -alkylene-CF 2 H; C 1-4 -alkylene-CFH 2 ; C(O)—C 1-6 -alkyl; C(O)—OH; C(O)—OC 1-6 -alkyl; C(O)—N(H)(OH); C(O)—NH 2 ; C(O)—N(H)(C 1-6 -alkyl); C(O)—N(C 1-6 -alkyl) 2 ; OH; OCF 3 ; OCF 2 H; OCFH 2 ; OCF 2 Cl; OCFCl 2 ; O—C 1-6 -alkyl; O—C 3-6 -cycloalkyl; O-(3 to 6-membered heterocycloalkyl); NH 2 ; N(H)(C 1-6 -alkyl); N(C 1-6 -alkyl) 2 ; N(H)—C(O)—C 1-6 -alkyl; N(C 1-6 -alkyl)-C(O)—C 1-6 -alkyl; N(H)—C(O)—NH 2 ; N(H)—C(O)—N(H)(C 1-6 -alkyl); N(H)—C(O)—N(C 1-6 -alkyl) 2 ; N(C 1-6 -alkyl)-C(O)—N(H)(C 1-6 -alkyl); N(C 1-6 -alkyl)-C(O)—N(C 1-6 -alkyl) 2 ; N(H)—S(O) 2 —C 1-6 -alkyl; SCF 3 ; S—C 1-6 -alkyl; S(O)—C 1-6 -alkyl; S(O) 2 —C 1-6 -alkyl; S(O) 2 —NH 2 ; S(O) 2 —N(H)(C 1-6 -alkyl); S(O) 2 —N(C 1-6 -alkyl) 2 ; C 3-6 -cycloalkyl; C 1-4 -alkylene-C 3-6 -cycloalkyl; 3 to 6-membered heterocycloalkyl; C 1-4 -alkylene-(3 to 6-membered heterocycloalkyl); phenyl or 5 or 6-membered heteroaryl;
in the form of the free compound or a physiologically acceptable salt thereof.
2. The compound according to claim 1 , wherein R 5 and R 6 both represent CH 3 .
3. The compound according to claim 1 , which is according to general formula (II) or (III):
4. The compound according to claim 1 , wherein X represents NR 7 and Z represents N or CR 9 .
5. The compound according to claim 1 , wherein
R 1 represents H; C 1-6 -alkyl; C 3-6 -cycloalkyl; 3 to 6-membered heterocycloalkyl; phenyl; or 5 or 6-membered heteroaryl;
wherein C 3-6 -cycloalkyl, 3 to 6-membered heterocycloalkyl, phenyl and 5 or 6-membered heteroaryl can optionally be bridged via C 1-4 -alkylene.
6. The compound according to claim 1 , wherein
R 2 represents H; F; Cl; Br; CN; C 1-6 -alkyl; C 3-6 -cycloalkyl; O—C 1-6 -alkyl; C(O)—NH 2 ; C(O)—N(H)(C 1-6 -alkyl); C(O)—N(C 1-6 -alkyl) 2 ; C(O)—N(H)(C 3-6 -cycloalkyl) or C(O)—N(C 1-6 -alkyl)(C 3-6 -cycloalkyl);
wherein C 3-6 -cycloalkyl can optionally be bridged via C 1-4 -alkylene; and/or
R 3 represents H; F; Cl; Br; CN; C 1-6 -alkyl; C 3-6 -cycloalkyl; O—C 1-6 -alkyl; C(O)—NH 2 ; C(O)—N(H)(C 1-6 -alkyl); C(O)—N(C 1-6 -alkyl) 2 ; C(O)—N(H)(C 3-6 -cycloalkyl) or C(O)—N(C 1-6 -alkyl)(C 3-6 -cycloalkyl);
wherein C 3-6 -cycloalkyl can optionally be bridged via C 1-4 -alkylene.
7. The compound according to claim 1 , wherein R 7 represents H.
8. The compound according to claim 1 , wherein R 7 represents L-R 8 ;
wherein
L represents a bond; S(O); S(O) 2 ; C 1-4 -alkylene; C(O); C 1-4 -alkylene-C(O); C(O)—O; C 1-4 -alkylene-C(O)—O; C 1-4 -alkylene-N(H)—C(O) or C 1-4 -alkylene-N(H)—C(O)—O; and
R 8 represents C 1-6 -alkyl; C 3-6 -cycloalkyl or 3 to 6-membered heterocycloalkyl; wherein C 3-6 -cycloalkyl and 3 to 6-membered heterocycloalkyl can optionally be bridged via C 1-4 -alkylene.
9. The compound according to claim 1 , wherein
R 9 represents H; F; CN; methyl; ethyl; n-propyl; 2-propyl; CF 3 ; CH 2 CF 3 ; CHF 2 ; CH 2 CHF 2 ; CH 2 F; CH 2 CH 2 F; S(O)—CH 3 ; S(O)—CH 2 CH 3 ; S(O)—CH 2 CH 2 CH 3 ; S(O)—CH(CH 3 ) 2 ; S(O) 2 —CH 3 ; S(O) 2 —CH 2 CH 3 ; S(O) 2 —CH 2 CH 2 CH 3 or S(O) 2 —CH(CH 3 ) 2 .
10. The compound according to claim 1 , wherein
R 10 represents H; F; Cl; Br; CN; C 1-6 -alkyl; C 3-6 -cycloalkyl; 3 to 6-membered heterocycloalkyl; P(O)—(C 1-6 -alkyl) 2 ; P(O)(C 1-6 -alkyl)(C 3-6 -cycloalkyl); P(O)(C 1-6 -alkyl)(3 to 6-membered heterocycloalkyl) P(O)—(O—C 1-6 -alkyl) 2 ; P(O)(O—C 1-6 -alkyl)(O—C 3-6 -cycloalkyl); or P(O)(O—C 1-6 -alkyl)(O-(3 to 6-membered heterocycloalkyl)).
11. The compound according to claim 1 , wherein
R 11 represents F; Cl; Br; I; CN; C 1-6 -alkyl or O—C 1-6 -alkyl;
and/or
n represents 0, 1 or 2.
12. The compound according to claim 1 , wherein the compound is selected from the group consisting of:
38
8-(3-Cyclopropyl-5-fluoro-1H-indol-7-yl)-6-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
48
9-Ethyl-6-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,
4]triazolo[4,3-a]quinoxaline
49
9-Ethyl-6-fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
53
9-Ethyl-6-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4-trimethyl-5H-[1,
2,4]triazolo[4,3-a]quinoxaline
54
6-Fluoro-8-[6-fluoro-1-(2-methoxy-ethyl)-1H-indol-4-yl]-9-methoxy-1,4,4-trimethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
55
2-[6-Fluoro-4-(6-fluoro-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-
8-yl)-1H-indol-1-yl]-EtOH
56
6-Fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-
[1,2,4]triazolo[4,3-a]quinoxaline
57
6-Fluoro-9-methoxy-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
58
8-[1-(2,2-Difluoro-ethyl)-6-fluoro-1H-indol-4-yl]-6-fluoro-9-methoxy-1,4,4-trimethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
59
1-Cyclopropyl-6-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-9-methoxy-4,4-dimethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
60
1-Cyclopropyl-6-fluoro-9-methoxy-4,4-dimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
61
2-[4-(1-Cyclopropyl-6-fluoro-9-methoxy-4,4-dimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-
8-yl)-6-fluoro-1H-indol-1-yl]-EtOH
62
1-Cyclopropyl-6-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-9-methoxy-4,4-dimethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
63
1-Cyclopropyl-6-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-4,4,9-trimethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
64
1-Cyclopropyl-6-fluoro-4,4,9-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
65
2-[4-(1-Cyclopropyl-6-fluoro-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-
6-fluoro-1H-indol-1-yl]-EtOH
66
1-Cyclopropyl-6-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-4,4,9-trimethyl-5H-[1,2,
4]triazolo[4,3-a]quinoxaline
300
6-Fluoro-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
301
2-[4-(6-Fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-
1-yl]-EtOH
304
6-Fluoro-1,4,4,9-tetramethyl-8-(1-methyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline
305
8-(1-Cyclopropyl-1H-indol-4-yl)-6-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline
308
1-Ethyl-6-fluoro-4,4,9-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
316
1-Ethyl-6-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
322
1-Ethyl-6-fluoro-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
323
1-Ethyl-6-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-4,4,9-trimethyl-5H-[1,2,
4]triazolo[4,3-a]quinoxaline
326
8-[1-(2,2-Difluoro-ethyl)-1H-indol-4-yl]-6-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
340
6-Fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,
4]triazolo[4,3-a]quinoxaline
349
6-Fluoro-8-[1-(fluoro-methylsulfonyl)-1H-indol-4-yl]-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
350
8-[1-(Ethylsulfonyl)-1H-indol-4-yl]-6-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
352
6-Fluoro-1,4,4,9-tetramethyl-8-(3-methyl-1H-indazol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline
355
1-Ethyl-6-fluoro-4,4,9-trimethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline
366
6-Fluoro-8-[1-(isopropylsulfonyl)-1H-indol-4-yl]-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
374
1-Ethyl-6-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-4,4,9-trimethyl-5H-[1,
2,4]triazolo[4,3-a]quinoxaline
375
[2-[4-(6-Fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-
1-yl]-ethyl]-dimethyl-amine
378
6-Fluoro-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
389
1-Ethyl-6-fluoro-4,4,9-trimethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
391
8-[1-(Cyclopropylsulfonyl)-1H-indol-4-yl]-6-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
446
8-[1-(Ethylsulfonyl)-6-fluoro-1H-indol-4-yl]-6,7-difluoro-1,4,4,9-tetramethyl-5H-[1,2,
4]triazolo[4,3-a]quinoxaline
447
6,7-Difluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,
4]triazolo[4,3-a]quinoxaline
448
6,7-Difluoro-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
449
2-[4-(6,7-Difluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-6-fluoro-
1H-indol-1-yl]-EtOH
450
8-(1-Cyclopropyl-1H-indol-4-yl)-6-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline-
9-carbonitrile
451
6,7-Difluoro-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
452
6,7-Difluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4,9-tetramethyl-5H-
[1,2,4]triazolo[4,3-a]quinoxaline
453
[6-Fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxalin-9-yl]-MeOH
454
6-Chloro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
455
9-(Difluoro-methyl)-6-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
456
6-Chloro-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
457
6-Chloro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
458
6-Chloro-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
459
9-(Difluoro-methyl)-6-fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-
[1,2,4]triazolo[4,3-a]quinoxaline
460
9-(Difluoro-methyl)-8-[1-(ethylsulfonyl)-6-fluoro-1H-indol-4-yl]-6-fluoro-1,4,4-trimethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
461
9-(Difluoro-methyl)-8-[1-(ethylsulfonyl)-1H-indol-4-yl]-6-fluoro-1,4,4-trimethyl-5H-[1,
2,4]triazolo[4,3-a]quinoxaline
462
9-(Difluoro-methyl)-6-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-
[1,2,4]triazolo[4,3-a]quinoxaline
463
2-[4-(6-Chloro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-6-fluoro-
1H-indol-1-yl]-EtOH
464
2-[4-(9-Ethyl-6-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-6-fluoro-
1H-indol-1-yl]-EtOH
465
6-Fluoro-8-(6-fluoro-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline
466
9-(Difluoro-methyl)-6-fluoro-1,4,4-trimethyl-8-(3-methyl-1H-indazol-7-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
467
9-Cyclopropyl-6-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4-trimethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
468
6-Fluoro-8-(1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline
469
6-Fluoro-8-(1H-indol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline
470
6-Fluoro-8-(6-fluoro-1H-indol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-
a]quinoxaline
471
9-Cyclopropyl-6-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
472
9-Cyclopropyl-6-fluoro-1,4,4-trimethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
473
6-Fluoro-9-methoxy-1,4,4-trimethyl-8-[6-(trifluoromethyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
474
9-Cyclopropyl-6-fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
475
6-Fluoro-1,4,4,9-tetramethyl-8-(6-methyl-1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
476
6-Fluoro-9-methoxy-1,4,4-trimethyl-8-(6-methyl-1-methylsulfonyl-1H-indol-4-yl)-5H-
[1,2,4]triazolo[4,3-a]quinoxaline
477
4-(6-Fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indole-6-
carbonitrile
478
8-(3-Cyclopropyl-5-fluoro-1H-indol-7-yl)-6-fluoro-9-methoxy-1,4,4-trimethyl-5H-[1,
2,4]triazolo[4,3-a]quinoxaline
479
[8-[1-(Ethylsulfonyl)-6-fluoro-1H-indol-4-yl]-6-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxalin-9-yl]-methyl-amine
480
2-[6-Fluoro-4-(6-fluoro-1,4,4-trimethyl-9-methylamino-5H-[1,2,4]triazolo[4,3-a]quinoxalin-
8-yl)-1H-indol-1-yl]-EtOH
481
[8-(1-Cyclopropyl-1H-indol-4-yl)-6-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-
9-yl]-methyl-amine
482
6-Chloro-9-methoxy-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
483
6-Chloro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-
[1,2,4]triazolo[4,3-a]quinoxaline
484
6-Fluoro-1,4,4,9-tetramethyl-8-(1-methyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline
485
6-Fluoro-9-methoxy-1,4,4-trimethyl-8-(1-methyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
486
[6-Fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxalin-9-yl]-methyl-amine
487
[6-Fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-
a]quinoxalin-9-yl]-methyl-amine
488
6-Chloro-8-(6-fluoro-1H-indol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
489
6-Fluoro-8-(7-fluoro-1H-indazol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
490
6-Fluoro-8-(7-fluoro-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline
491
8-[1-(Cyclopropyl-methylsulfonyl)-1H-indol-4-yl]-6-fluoro-1,4,4,9-tetramethyl-5H-[1,
2,4]triazolo[4,3-a]quinoxaline
492
6-Fluoro-9-methoxy-1,4,4-trimethyl-8-[1-methylsulfonyl-6-(trifluoromethyl)-1H-indol-
4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline
493
6-Chloro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-
[1,2,4]triazolo[4,3-a]quinoxaline
494
6-Fluoro-8-(7-fluoro-1H-indol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-
a]quinoxaline
495
6-Fluoro-8-(6-fluoro-1H-indazol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
496
6-Fluoro-8-(6-fluoro-1H-indazol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline
497
8-[1-(Cyclopropyl-methylsulfonyl)-6-fluoro-1H-indol-4-yl]-6-fluoro-1,4,4,9-tetramethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
498
6,7-Difluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-9-methoxy-1,4,4-trimethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
499
6,7-Difluoro-9-methoxy-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,
4]triazolo[4,3-a]quinoxaline
500
6,7-Difluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-9-(trifluoromethyl)-5H-
[1,2,4]triazolo[4,3-a]quinoxaline
501
6,7-Difluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-9-methoxy-1,4,4-trimethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
502
6-Chloro-7-fluoro-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
503
6-Chloro-7-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-
[1,2,4]triazolo[4,3-a]quinoxaline
504
6-Fluoro-8-(1H-indazol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline
505
8-[1-(Cyclopropylsulfonyl)-1H-indol-4-yl]-6-fluoro-9-methoxy-1,4,4-trimethyl-5H-[1,
2,4]triazolo[4,3-a]quinoxaline
506
8-(6-Chloro-1H-indol-4-yl)-6-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline
507
6-Fluoro-1,4,4,9-tetramethyl-8-[6-(trifluoromethyl)-1H-indazol-4-yl]-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
508
6-Chloro-7-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
509
6-Chloro-7-fluoro-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,
4]triazolo[4,3-a]quinoxaline
510
6-Chloro-7-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4,9-tetramethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
511
8-(1-Cyclopropyl-1H-indol-4-yl)-6-fluoro-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
512
6,7-Difluoro-8-(1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline
513
6,7-Difluoro-1,4,4,9-tetramethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline
514
6,7-Difluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
515
6-Fluoro-8-(5-fluoro-1H-indol-7-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-
a]quinoxaline
516
6,7-Difluoro-8-(6-fluoro-1H-indol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
517
6-Fluoro-8-(7-fluoro-1H-indazol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline
518
6,7-Difluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
519
6,7-Difluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
520
4-(6,7-Difluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indole-
7-carbonitrile
521
6,7-Difluoro-8-(6-fluoro-1-methyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
522
6,7-Difluoro-8-(6-methoxy-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,
2,4]triazolo[4,3-a]quinoxaline
523
6-Fluoro-8-(6-methoxy-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,
4]triazolo[4,3-a]quinoxaline
524
6-Fluoro-9-methoxy-8-(6-methoxy-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-
[1,2,4]triazolo[4,3-a]quinoxaline
525
7-Chloro-6-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4,9-tetramethyl-
5H-[1,2,4]triazolo[4,3-a]quinoxaline
526
7-Chloro-6-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,
3-a]quinoxaline
527
7-Chloro-6-fluoro-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,
4]triazolo[4,3-a]quinoxaline
in the form of the free compound or a physiologically acceptable salt thereof.
13. A pharmaceutical dosage form comprising a compound according to claim 1 .
14. A method for treating pain and/or inflammation, comprising administering a therapeutically effective amount of a compound according to claim 1 to a patient in need thereof.
15. The method according to claim 14 , wherein the pain is inflammatory pain.