US 12,110,293 B2Granted

Substituted triazolo quinoxaline derivatives

AssigneeGrüNenthal GmbH

InventorsFlorian Jakob, Jo Alen, Simon Lucas, Tobias Craan, Ingo Konetzki, Achim Kless, Stefan Schunk, Paul Ratcliffe, Sebastian Wachten, Simon Cruwys

Life of this patent

Estimating the term…

Abstract

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.

Claims18

Dependent claims

A compound according to general formula (I),

wherein
R1 represents H;
C1-10-alkyl;
C3-10-cycloalkyl;
3 to 7 membered heterocycloalkyl;
aryl;
or 5 or 6-membered heteroaryl;
wherein C3-10-cycloalkyl, 3 to 7 membered heterocycloalkyl, aryl and 5 or 6-membered heteroaryl can optionally be bridged via C1-6-alkylene;
R2 represents H;
F;
Cl;
Br;
I;
CN;
C1-10-alkyl;
C3-10-cycloalkyl;
O—C1-10-alkyl;
N(H)(C1-10-alkyl), N(C1-10-alkyl)2;
C(O)—C1-10-alkyl;
C(O)—O—C1-10-alkyl;
C(O)—NH2;
C(O)—N(H)(C1-10-alkyl);
C(O)—N(C1-10-alkyl)2;
O—C3-10-cycloalkyl;
N(H)(C3-10-cycloalkyl), N(C1-10-alkyl)(C3-10-cycloalkyl);
C(O)—C3-10-cycloalkyl;
C(O)—O—C3-10-cycloalkyl;
C(O)—N(H)(C3-10-cycloalkyl) or C(O)—N(C1-10-alkyl)(C3-10-cycloalkyl);
wherein C3-10-cycloalkyl can optionally be bridged via C1-6-alkylene;
R3 represents H;
F;
Cl;
Br;
I;
CN;
C1-10-alkyl;
C3-10-cycloalkyl;
O—C1-10-alkyl;
N(H)(C1-10-alkyl);
N(C1-10-alkyl)2;
C(O)—C1-10-alkyl;
C(O)—O—C1-10-alkyl;
C(O)—NH2;
C(O)—N(H)(C1-10-alkyl);
C(O)—N(C1-10-alkyl)2;
O—C3-10-cycloalkyl;
N(H)(C3-10-cycloalkyl), N(C1-10-alkyl)(C3-10-cycloalkyl);
C(O)—C3-10-cycloalkyl;
C(O)—O—C3-10-cycloalkyl;
C(O)—N(H)(C3-10-cycloalkyl) or C(O)—N(C1-10-alkyl)(C3-10-cycloalkyl);
wherein C3-10-cycloalkyl can optionally be bridged via C1-6-alkylene;
R5 and R6 represent independently from one another H or unsubstituted C1-4-alkyl;
X represents N or NR7;
Z represents N, NR7 or CR9;
with the proviso that
when X represents NR7, Z represents N or CR9;
when X represents N, Z represents NR7;
R7 represents H or L-R8;
wherein
L represents bond;
S(O);
S(O)2;
C1-6-alkylene;
C(O);
C1-6-alkylene-C(O);
C(O)—O;
C1-6-alkylene-C(O)—O;
C1-6-alkylene-N(H)—C(O);
C1-6-alkylene-N(C1-10-alkyl)-C(O);
C1-6-alkylene-N(H)—C(O)—O;
C1-6-alkylene-N(C1-10-alkyl)-C(O)—O;
O;
NH or N(C1-10-alkyl);
R8 represents C1-10-alkyl;
C3-10-cycloalkyl or 3 to 7 membered heterocycloalkyl;
wherein C3-10-cycloalkyl and 3 to 7 membered heterocycloalkyl can optionally be bridged via C1-6-alkylene;
R9 and R10 represent independently from one another H;
F;
Cl;
Br;
I;
CN;
C1-10-alkyl;
C3-10-cycloalkyl;
3 to 7 membered heterocycloalkyl;
S(O)-(C1-10-alkyl);
S(O)-(C3-10-cycloalkyl);
S(O)-(3 to 7-membered heterocycloalkyl);
S(O)2—(C1-10-alkyl);
S(O)2—(C3-10-cycloalkyl);
S(O)2-(3 to 7-membered heterocycloalkyl);
P(O)-(C1-10-alkyl)2;
P(O)(C1-10-alkyl)(C3-10-cycloalkyl);
P(O)(C1-10-alkyl)(3 to 7-membered heterocycloalkyl);
P(O)—(O—C1-10-alkyl)2;
P(O)(O—C1-10-alkyl)(O—C3-10-cycloalkyl);
P(O)(O—C1-10-alkyl)(O-(3 to 7-membered heterocycloalkyl));
O—C1-10-alkyl;
S—C1-10-alkyl;
N(H)(C1-10-alkyl), N(C1-10-alkyl)2;
C(O)—C1-10-alkyl;
C(O)—O—C1-10-alkyl;
C(O)—NH2;
C(O)—N(H)(C1-10-alkyl);
C(O)—N(C1-10-alkyl)2;
O—C3-10-cycloalkyl;
N(H)(C3-10-cycloalkyl), N(C1-10-alkyl)(C3-10-cycloalkyl);
C(O)—C3-10-cycloalkyl;
C(O)—O—C3-10-cycloalkyl;
C(O)—N(H)(C3-10-cycloalkyl);
C(O)—N(C1-10-alkyl)(C3-10-cycloalkyl);
O-3 to 7-membered heterocycloalkyl;
N(H)(3 to 7-membered heterocycloalkyl), N(C1-10-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(C1-10-alkyl)(3 to 7-membered heterocycloalkyl);
wherein C3-10-cycloalkyl and 3 to 7 membered heterocycloalkyl can optionally be bridged via C1-6-alkylene;
R11 represents F;
Cl;
Br;
I;
CN;
C1-10-alkyl;
O—C1-10-alkyl;
NO2;
OH, NH2;
C3-10-cycloalkyl;
3 to 7-membered heterocycloalkyl;
S(O)-(C1-10-alkyl);
S(O)-(C3-10-cycloalkyl);
S(O)-(3 to 7-membered heterocycloalkyl);
S(O)2—(C1-10-alkyl);
S(O)2—(C3-10-cycloalkyl);
S(O)2-(3 to 7-membered heterocycloalkyl);
P(O)-(C1-10-alkyl)2;
P(O)(C1-10-alkyl)(C3-10-cycloalkyl);
P(O)(C1-10-alkyl)(3 to 7-membered heterocycloalkyl);
P(O)—(O—C1-10-alkyl)2;
P(O)(O—C1-10-alkyl)(O—C3-10-cycloalkyl);
P(O)(O—C1-10-alkyl)(O-(3 to 7-membered heterocycloalkyl));
O—C1-10-alkyl;
N(H)(C1-10-alkyl), N(C1-10-alkyl)2;
C(O)—C1-10-alkyl;
C(O)—O—C1-10-alkyl;
C(O)—NH2;
C(O)—N(H)(C1-10-alkyl);
C(O)—N(C1-10-alkyl)2;
O—C3-10-cycloalkyl;
N(H)(C3-10-cycloalkyl), N(C1-10-alkyl)(C3-10-cycloalkyl);
C(O)—C3-10-cycloalkyl;
C(O)—O—C3-10-cycloalkyl;
C(O)—N(H)(C3-10-cycloalkyl);
C(O)—N(C1-10-alkyl)(C3-10-cycloalkyl);
O-3 to 7-membered heterocycloalkyl;
N(H)(3 to 7-membered heterocycloalkyl), N(C1-10-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(C1-10-alkyl)(3 to 7-membered heterocycloalkyl);
wherein C3-10-cycloalkyl and 3 to 7 membered heterocycloalkyl can optionally be bridged via C1-6-alkylene;
n represents 0, 1, 2 or 3;
wherein C1-10-alkyl, C1-4-alkyl and C1-6-alkylene in each case independently from one another is linear or branched, saturated or unsaturated;
wherein C1-10-alkyl, C1-4-alkyl, C1-6-alkylene, C3-10-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;
C1-6-alkyl;
CF3;
CF2H;
CFH2;
CF2Cl;
CFCl2;
C(O)—C1-6-alkyl;
C(O)—OH;
C(O)—OC1-6-alkyl;
C(O)—NH2;
C(O)—N(H)(C1-6-alkyl);
C(O)—N(C1-6-alkyl)2;
OH;
═O;
OCF3;
OCF2H;
OCFH2;
OCF2Cl;
OCFCl2;
O—C1-6-alkyl;
O—C(O)—C1-6-alkyl;
O—C(O)—O—C1-6-alkyl;
O—(CO)—N(H)(C1-6-alkyl);
O—C(O)—N(C1-6-alkyl)2;
O—S(O)2—NH2;
O—S(O)2—N(H)(C1-6-alkyl);
O—S(O)2—N(C1-6-alkyl)2;
NH2;
N(H)(C1-6-alkyl);
N(C1-6-alkyl)2;
N(H)—C(O)—C1-6-alkyl;
N(H)—C(O)—O—C1-6-alkyl;
N(H)—C(O)—NH2;
N(H)—C(O)—N(H)(C1-6-alkyl);
N(H)—C(O)—N(C1-6-alkyl)2;
N(C1-6-alkyl)-C(O)—C1-6-alkyl;
N(C1-6-alkyl)-C(O)—O—C1-6-alkyl;
N(C1-6-alkyl)-C(O)—NH2;
N(C1-6-alkyl)-C(O)—N(H)(C1-6-alkyl);
N(C1-6-alkyl)-C(O)—N(C1-6-alkyl)2;
N(H)—S(O)2OH;
N(H)—S(O)2—C1-6-alkyl;
N(H)—S(O)2—O—C1-6-alkyl;
N(H)—S(O)2—NH2;
N(H)—S(O)2—N(H)(C1-6-alkyl);
N(H)—S(O)2N(C1-6-alkyl)2;
N(C1-6-alkyl)-S(O)2—OH;
N(C1-6-alkyl)-S(O)2—C1-6-alkyl;
N(C1-6-alkyl)-S(O)2—O—C1-6-alkyl;
N(C1-6-alkyl)-S(O)2—NH2;
N(C1-6-alkyl)-S(O)2—N(H)(C1-6-alkyl);
N(C1-6-alkyl)-S(O)2—N(C1-6-alkyl)2;
SCF3;
SCF2H;
SCFH2;
S—C1-6-alkyl;
S(O)—C1-6-alkyl;
S(O)2—C1-6-alkyl;
S(O)2—OH;
S(O)2—O—C1-6-alkyl;
S(O)2—NH2;
S(O)2—N(H)(C1-6-alkyl);
S(O)2—N(C1-6-alkyl)2;
C3-6-cycloalkyl;
3 to 6-membered heterocycloalkyl;
phenyl;
5 or 6-membered heteroaryl;
O—C3-6-cycloalkyl;
O-(3 to 6-membered heterocycloalkyl);
O-phenyl;
O-(5 or 6-membered heteroaryl);
C(O)—C3-6-cycloalkyl;
C(O)-(3 to 6-membered heterocycloalkyl);
C(O)-phenyl;
C(O)-(5 or 6-membered heteroaryl);
S(O)2—(C3-6-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;
C1-6-alkyl;
CF3;
CF2H;
CFH2;
CF2Cl;
CFCl2;
C1-4-alkylene-CF3;
C1-4-alkylene-CF2H;
C1-4-alkylene-CFH2;
C(O)—C1-6-alkyl;
C(O)—OH;
C(O)—OC1-6-alkyl;
C(O)—N(H)(OH);
C(O)—NH2;
C(O)—N(H)(C1-6-alkyl);
C(O)—N(C1-6-alkyl)2;
OH;
OCF3;
OCF2H;
OCFH2;
OCF2Cl;
OCFCl2;
O—C1-6-alkyl;
O—C3-6-cycloalkyl;
O-(3 to 6-membered heterocycloalkyl);
NH2;
N(H)(C1-6-alkyl);
N(C1-6-alkyl)2;
N(H)—C(O)—C1-6-alkyl;
N(C1-6-alkyl)-C(O)—C1-6-alkyl;
N(H)—C(O)—NH2;
N(H)—C(O)—N(H)(C1-6-alkyl);
N(H)—C(O)—N(C1-6-alkyl)2;
N(C1-6-alkyl)-C(O)—N(H)(C1-6-alkyl);
N(C1-6-alkyl)-C(O)—N(C1-6-alkyl)2;
N(H)—S(O)2—C1-6-alkyl;
SCF3;
S—C1-6-alkyl;
S(O)—C1-6-alkyl;
S(O)2—C1-6-alkyl;
S(O)2—NH2;
S(O)2—N(H)(C1-6-alkyl);
S(O)2—N(C1-6-alkyl)2;
C3-6-cycloalkyl;
C1-4-alkylene-C3-6-cycloalkyl;
3 to 6-membered heterocycloalkyl;
C1-4-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.

295 more elements

A compound selected from the group consisting of:

1 7,9-Difluoro-8-(6-fluoro-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
2 8-(1-Cyclopropyl-6-fluoro-1H-indol-4-yl)-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
3 7,9-Difluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
4 1-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-6-fluoro-1H-indol-1-yl]-ethanone;
5 7,9-Difluoro-8-(6-fluoro-2-methyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
6 4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-6-fluoro-1H-indole-2-carbonitrile;
9 7,9-Difluoro-8-(1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
10 7,9-Difluoro-1,4,4-trimethyl-8-[3-(trifluoromethyl)-1H-indol-7-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
11 1-Ethyl-7,9-difluoro-8-(1H-indol-7-yl)-4,4-dimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
12 7-(1-Ethyl-7,9-difluoro-4,4-dimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indole-3-carbonitrile;
13 1-Ethyl-7,9-difluoro-4,4-dimethyl-8-(3-prop-1-ynyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
14 1-Ethyl-7,9-difluoro-8-(5-fluoro-1H-indol-7-yl)-4,4-dimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
15 7-(1-Ethyl-7,9-difluoro-4,4-dimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-5-fluoro-1H-indole-3-carbonitrile;
16 1-Ethyl-7,9-difluoro-8-(5-fluoro-3-prop-1-ynyl-1H-indol-7-yl)-4,4-dimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
17 7-(1-Ethyl-7,9-difluoro-4,4-dimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-5-methyl-1H-indole-3-carbonitrile;
18 8-[1-(Ethylsulfonyl)-6-fluoro-1H-indol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
19 8-[1-(Cyclopropylsulfonyl)-6-fluoro-1H-indol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
20 1-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-ethanone;
21 7,9-Difluoro-8-[6-fluoro-1-(2,2,2-trifluoro-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
22 7,9-Difluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
23 7-Fluoro-8-[5-fluoro-3-(2,2,2-trifluoro-ethyl)-1H-indol-7-yl]-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
24 7-Fluoro-1,4,4,9-tetramethyl-8-[3-(2,2,2-trifluoro-ethyl)-1H-indol-7-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
25 7-Fluoro-8-(1H-indol-7-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
26 7-Fluoro-8-(1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
27 8-(1-Cyclopropyl-1H-indol-4-yl)-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
28 7-Fluoro-1,4,4,9-tetramethyl-8-(3-prop-1-ynyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
29 7-Fluoro-1,4,4-trimethyl-8-(3-methyl-1H-indol-7-yl)-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
30 9-Chloro-7-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
31 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;
32 7-Fluoro-8-(5-fluoro-1H-indol-7-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
33 8-(3-Cyclopropyl-5-fluoro-1H-indol-7-yl)-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
34 1-Ethyl-7-fluoro-8-(6-fluoro-1H-indol-4-yl)-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
35 8-[1-(Cyclopropyl-methyl)-6-fluoro-1H-indol-4-yl]-1-ethyl-7-fluoro-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
36 1-Ethyl-7-fluoro-8-[6-fluoro-1-(2-methoxy-ethyl)-1H-indol-4-yl]-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
37 7-Fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
39 4-[7-(7-Fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-3-yl]-2-methyl-but-3-yn-2-ol;
40 [3-[7-(7-Fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-3-y1]-1,1-dimethyl-prop-2-ynyl]-amine;
41 9-Chloro-8-(3-cyclobutyl-1H-indol-7-yl)-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
42 7-Fluoro-1,4,4,9-tetramethyl-8-(3-tetrahydro-furan-3-yl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
43 8-(3-Ethyl-5-fluoro-1H-indol-7-yl)-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
44 2-[4-(9-Ethyl-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-6-fluoro-1H-indol-1-yl]-ethanol;
45 2-[4-(9-Ethyl-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-6-fluoro-1H-indazol-1-yl]-ethanol;
46 9-Ethyl-7-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
47 9-Ethyl-7-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
50 9-Ethyl-7-fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
51 9-Ethyl-7-fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
52 9-Ethyl-7-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
67 1-Benzyl-7,9-difluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-4,4-dimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
68 1-Benzyl-7,9-difluoro-4,4-dimethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
69 1-But-2-ynyl-7,9-difluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-4,4-dimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
70 1-But-2-ynyl-7,9-difluoro-4,4-dimethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
71 7,9-Difluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-4,4-dimethyl-1-(pyridin-4-yl-methyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
72 7,9-Difluoro-4,4-dimethyl-8-(3-methyl-1H-indol-7-yl)-1-(pyridin-4-yl-methyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
73 7,9-Difluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-4,4-dimethyl-1-(pyridin-3-yl-methyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
74 7,9-Difluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-4,4-dimethyl-1-(pyridin-2-yl-methyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
75 7,9-Difluoro-4,4-dimethyl-8-(3-methyl-1H-indol-7-yl)-1-(pyridin-2-yl-methyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
76 7-Fluoro-8-(5-fluoro-3-prop-1-ynyl-1H-indol-7-yl)-1-(methoxymethyl)-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
77 [7-Fluoro-8-(5-fluoro-3-prop-1-ynyl-1H-indol-7-yl)-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl]-MeOH;
78 1-[7-Fluoro-8-(5-fluoro-3-prop-1-ynyl-1H-indol-7-yl)-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl]-ethanol;
79 7-Fluoro-8-(5-fluoro-3-prop-1-ynyl-1H-indol-7-yl)-1-(2-methoxy-ethyl)-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
80 1-(Cyclopropyl-methyl)-7,9-difluoro-8-(1H-indol-7-yl)-4,4-dimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
81 1-Cyclopropyl-7,9-difluoro-8-(1H-indol-7-yl)-4,4-dimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
82 8-(3-Cyclopropyl-1H-indol-7-yl)-1,4,4,9-tetramethyl-7-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
83 8-(6-Fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-7-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
84 1,4,4,9-Tetramethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-7-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
85 9-Chloro-8-(3-cyclopropyl-1H-indol-7-yl)-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
86 7-Fluoro-8-(1H-indol-7-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
87 8-(3-Cyclopropyl-5-fluoro-1H-indol-7-yl)-7-fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
88 8-(1-Cyclopropyl-6-fluoro-1H-indol-4-yl)-7-fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
89 7-[7-Fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-1H-indole-3-carbonitrile;
200 7,9-Difluoro-8-[1-(isopropylsulfonyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
201 8-[1-(Cyclopentylsulfonyl)-1H-indol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
202 8-[1-(Cyclopropyl-methyl)-1H-indol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
203 7,9-Difluoro-1,4,4-trimethyl-8-[1-(tetrahydro-pyran-4-ylsulfonyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
204 7,9-Difluoro-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
205 8-[1-(Cyclopropylsulfonyl)-1H-indol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
207 7,9-Difluoro-1,4,4-trimethyl-8-[6-(trifluoromethyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
208 7,9-Difluoro-8-(6-fluoro-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
210 8-[1-(Cyclopropyl-methylsulfonyl)-1H-indol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
212 2-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-N,N-dimethyl-acetamide;
213 1-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-2-methoxy-ethanone;
214 7,9-Difluoro-8-(5-fluoro-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
219 3-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-propionic acid methyl ester;
221 7,9-Difluoro-1,4,4-trimethyl-8-(1-methyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
222 7,9-Difluoro-1,4,4-trimethyl-8-(2-methyl-2H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
223 1-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-2-dimethylamino-ethanone;
224 7,9-Difluoro-8-(5-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
225 7,9-Difluoro-1,4,4-trimethyl-8-[2-(trifluoromethyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
228 N-[2-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-ethyl]-carbamic acid tert-butyl ester;
229 N-[2-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-ethyl]-2,2-difluoro-propionamide;
230 2-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-ethyl-amine;
232 7,9-Difluoro-8-(1H-indazol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
233 7,9-Difluoro-8-[1-(2-methoxy-ethyl)-1H-indazol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
234 8-[1-(Cyclopropylsulfonyl)-1H-indazol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
235 8-[1-(Cyclopropyl-methyl)-1H-indazol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
236 8-(1-Ethyl-1H-indazol-4-yl)-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
237 8-(2-Ethyl-2H-indazol-4-yl)-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
238 4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indazole-1-carboxylic acid tert-butyl ester;
239 8-[1-(Cyclopropyl-methylsulfonyl)-1H-indazol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
240 1-Ethyl-7-fluoro-4,4,9-trimethyl-8-(1-methyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
241 1-Ethyl-7-fluoro-4,4,9-trimethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
242 8-(1-Cyclopropyl-1H-indazol-4-yl)-1-ethyl-7-fluoro-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
243 8-(1-Cyclopropyl-1H-indazol-4-yl)-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
244 1-Ethyl-7-fluoro-8-(5-fluoro-1H-indol-4-yl)-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
247 1-Ethyl-7-fluoro-4,4,9-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
248 7-Fluoro-9-methoxy-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
249 7-Fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
250 7-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;
251 9-Fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-7-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
252 7-(Difluoro-methoxy)-9-fluoro-1,4,4-trimethyl-8-[2-(trifluoromethyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
253 8-[1-(2,2-Difluoro-ethyl)-1H-indol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
254 7-Chloro-9-fluoro-1,4,4-trimethyl-8-[2-(trifluoromethyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
255 9-Fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-7-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
256 9-Fluoro-8-(1H-indol-4-yl)-7-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
257 9-Fluoro-7-methoxy-1,4,4-trimethyl-8-[2-(trifluoromethyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
258 2-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indazol-1-yl]-ethanol;
259 7-(Difluoro-methoxy)-9-fluoro-8-[1-(2-methoxy-ethyl)-2-(trifluoromethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
260 4-(7-Fluoro-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indole-1-carboxylic acid tert-butyl ester;
263 9-Fluoro-7-methoxy-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
264 7-Fluoro-9-methoxy-1,4,4-trimethyl-8-(1-methyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
266 9-Fluoro-7-methoxy-1,4,4-trimethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
267 7-(Difluoro-methoxy)-9-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
268 7-(Difluoro-methoxy)-9-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
269 9-Fluoro-7-methoxy-1,4,4-trimethyl-8-(1-methyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
270 7-Fluoro-9-methoxy-1,4,4-trimethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
271 7,9-Difluoro-1,4,4-trimethyl-8-[1-methylsulfonyl-2-(trifluoromethyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
272 7-Chloro-9-fluoro-1,4,4-trimethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
273 7-(Difluoro-methoxy)-9-fluoro-1,4,4-trimethyl-8-(1-methyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
275 7-(Difluoro-methoxy)-9-fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
276 7,9-Difluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
277 7-Chloro-9-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
278 7-Fluoro-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
279 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;
280 7-Chloro-9-fluoro-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
281 7-Fluoro-9-methoxy-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
282 7-(Difluoro-methoxy)-9-fluoro-1,4,4-trimethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
283 9-Fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
284 7-Chloro-9-fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
285 7-Chloro-9-fluoro-1,4,4-trimethyl-8-(1-methyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
286 7-Fluoro-8-(1H-indol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
287 7-(Difluoro-methoxy)-9-fluoro-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
288 9-Fluoro-7-methoxy-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
289 7,9-Difluoro-8-[1-(2-methoxy-ethyl)-2-(trifluoromethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
290 7-Chloro-9-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
292 9-(Difluoro-methyl)-7-fluoro-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
293 7-Chloro-9-fluoro-8-(1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
294 9-(Difluoro-methyl)-7-fluoro-1,4,4-trimethyl-8-(1-methyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
295 7-(Difluoro-methyl)-9-fluoro-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
296 7-(Difluoro-methyl)-9-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
297 7-(Difluoro-methoxy)-9-fluoro-8-(1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
298 7-(Difluoro-methyl)-9-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
299 1-Ethyl-7-fluoro-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
302 9-(Difluoro-methyl)-7-fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
306 7-(Difluoro-methyl)-9-fluoro-1,4,4-trimethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
309 1,4,4,7,9-Pentamethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
310 7-Methoxy-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
312 8-[1-Cyclopropyl-2-(trifluoromethyl)-1H-indol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
313 7-Chloro-8-[1-(2,2-difluoro-ethyl)-1H-indol-4-yl]-9-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
314 8-[1-(2,2-Difluoro-ethyl)-1H-indol-4-yl]-9-fluoro-7-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
315 9-(Difluoro-methyl)-7-fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
317 7-Chloro-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
318 7-(Difluoro-methoxy)-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
319 9-(Difluoro-methyl)-7-fluoro-8-(1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
320 9-(Difluoro-methyl)-7-fluoro-1,4,4-trimethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
321 9-Fluoro-1,4,4,7-tetramethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
324 8-[1-(2,2-Difluoro-ethyl)-1H-indol-4-yl]-1,4,4,7,9-pentamethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
325 7-(Difluoro-methyl)-9-fluoro-1,4,4-trimethyl-8-(1-methyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
327 7-Chloro-8-[1-(2,2-difluoro-ethyl)-1H-indol-4-yl]-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
328 8-(6-Fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,7,9-pentamethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
329 8-(6-Fluoro-1-methylsulfonyl-1H-indol-4-yl)-7-methoxy-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
330 8-[1-(2,2-Difluoro-ethyl)-1H-indol-4-yl]-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
331 8-[1-(2-Methoxy-ethyl)-1H-indol-4-yl]-1,4,4,7,9-pentamethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
332 9-Fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,7-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
333 7-Chloro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
334 7-Methoxy-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
335 7-(Difluoro-methoxy)-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
336 7-(Difluoro-methoxy)-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
337 9-Fluoro-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4,7-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
338 7-Chloro-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
339 7-Fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
341 8-(5-Fluoro-3-methyl-1H-indol-7-yl)-1,4,4,7,9-pentamethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
342 7-Fluoro-9-methoxy-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
343 7-(Difluoro-methyl)-9-fluoro-8-(1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
344 7-Methoxy-8-[1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
345 8-(5-Fluoro-3-methyl-1H-indol-7-yl)-7-methoxy-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
346 9-(Difluoro-methyl)-7-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
347 7-Chloro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
348 1-Ethyl-7-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-4,4,9-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
351 7-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;
353 9-Fluoro-8-[6-fluoro-1-(2-methoxy-ethyl)-1H-indol-4-yl]-7-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
354 7,9-Difluoro-1,4,4-trimethyl-8-(3-methyl-1H-indazol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
356 1,4,4,7,9-Pentamethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
357 7-Methoxy-1,4,4-trimethyl-8-(3-methyl-1H-indol-7-yl)-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
358 7-Chloro-1,4,4,9-tetramethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
359 9-Fluoro-1,4,4,7-tetramethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
360 7-(Difluoro-methoxy)-1,4,4,9-tetramethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
361 7-Fluoro-1,4,4,9-tetramethyl-8-(3-methyl-1H-indazol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
362 8-[1-(Ethylsulfonyl)-6-fluoro-1H-indol-4-yl]-7-fluoro-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
363 7-Chloro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
364 9-Fluoro-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4,7-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
365 7-(Difluoro-methoxy)-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
367 9-(Difluoro-methyl)-7-fluoro-1,4,4-trimethyl-8-(3-methyl-1H-indazol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
368 7-Chloro-1,4,4,9-tetramethyl-8-(3-methyl-1H-indazol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
369 8-[1-(Ethylsulfonyl)-6-fluoro-1H-indol-4-yl]-7-methoxy-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
370 8-[1-(Ethylsulfonyl)-6-fluoro-1H-indol-4-yl]-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
371 8-[1-(Ethylsulfonyl)-1H-indol-4-yl]-7-methoxy-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
372 8-[1-(Ethylsulfonyl)-1H-indol-4-yl]-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
373 8-(6-Fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4,7,9-pentamethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
376 8-(6-Fluoro-1-methylsulfonyl-1H-indazol-4-yl)-7-methoxy-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
377 7-Fluoro-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
379 2-[6-Fluoro-4-(9-fluoro-7-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-ethanol;
380 2-[6-Fluoro-4-(7-fluoro-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-ethanol;
381 7-Fluoro-9-methoxy-1,4,4-trimethyl-8-(3-methyl-1H-indazol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
382 9-(Difluoro-methyl)-7-fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
383 [2-[4-(7,9-Difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-ethyl]-dimethyl-amine;
384 8-[1-(2,2-Difluoro-ethyl)-1H-indol-4-yl]-7-(difluoro-methoxy)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
385 2-[4-[7-(Difluoro-methyl)-9-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-6-fluoro-1H-indol-1-yl]-ethanol;
386 7-Chloro-1,4,4,9-tetramethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
387 7-Methoxy-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
388 1,4,4,7,9-Pentamethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
390 9-(Difluoro-methyl)-7-fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
392 8-[1-(2,2-Difluoro-ethyl)-1H-indol-4-yl]-9-fluoro-1,4,4,7-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
393 8-[1-(2,2-Difluoro-ethyl)-1H-indol-4-yl]-7-(difluoro-methoxy)-9-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
394 7-(Difluoro-methoxy)-9-fluoro-8-[6-fluoro-1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
395 2-[4-[7-(Difluoro-methoxy)-9-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-6-fluoro-1H-indol-1-yl]-ethanol;
396 7-(Difluoro-methyl)-9-fluoro-8-[6-fluoro-1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
397 8-[1-(2,2-Difluoro-ethyl)-1H-indol-4-yl]-7-fluoro-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
398 8-[1-(2,2-Difluoro-ethyl)-1H-indol-4-yl]-9-(difluoro-methyl)-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
399 7-Fluoro-8-(1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
400 9-(Difluoro-methyl)-7-fluoro-8-[1-(isopropylsulfonyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
401 8-[1-(Cyclopropylsulfonyl)-1H-indol-4-yl]-9-(difluoro-methyl)-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
402 9-(Difluoro-methyl)-7-fluoro-8-[6-fluoro-1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
403 8-(6-Fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-7-(trifluoromethyloxy)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
404 7-Chloro-9-fluoro-8-[6-fluoro-1-(2-methoxy-ethyl)-1H-indol-4-yl]-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
405 1,4,4,9-Tetramethyl-8-(3-methyl-1H-indol-7-yl)-7-(trifluoromethyloxy)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
406 8-(5-Fluoro-3-methyl-1H-indol-7-yl)-1,4,4,9-tetramethyl-7-(trifluoromethyloxy)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
407 8-(5-Fluoro-3-methyl-1H-indol-7-yl)-7-methoxy-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
445 7,9-Difluoro-8-(1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
446 7-Fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
447 2-[6-Fluoro-4-[7-fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-1H-indol-1-yl]-ethanol;
448 8-[1-(Ethylsulfonyl)-6-fluoro-1H-indazol-4-yl]-7-fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
449 2-[6-Fluoro-4-[7-fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-1H-indazol-1-yl]-ethanol;
450 1,4,4,9-Tetramethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
451 2-[6-Fluoro-4-(1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indol-1-yl]-ethanol;
452 8-(5-Fluoro-3-methyl-1H-indol-7-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
453 8-(6-Fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
454 7-Fluoro-8-(6-fluoro-1-methylsulfonyl-1H-indazol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
455 8-[1-(Ethylsulfonyl)-1H-indol-4-yl]-7-fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
456 2-[4-[7-Fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-1H-indol-1-yl]-ethanol;
457 1,4,4,9-Tetramethyl-8-(1-methylsulfonyl-1H-indazol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
458 8-(5-Fluoro-3-methyl-1H-indol-7-yl)-1,4,4,9-tetramethyl-7-(trifluoromethyloxy)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
459 8-(5-Fluoro-3-methyl-1H-indol-7-yl)-7-methoxy-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
460 8-[1-(2-Methoxy-ethyl)-1H-indol-4-yl]-1,4,4,9-tetramethyl-7-(trifluoromethyloxy)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
461 9-(Difluoro-methyl)-8-[1-(ethylsulfonyl)-1H-indol-4-yl]-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
462 9-Cyclopropyl-7-fluoro-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
463 9-Cyclopropyl-7-fluoro-1,4,4-trimethyl-8-(3-methyl-1H-indol-7-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
464 7-Fluoro-8-(6-fluoro-1H-indol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
465 1,4,4,9-Tetramethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-7-(trifluoromethyloxy)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
466 9-(Difluoro-methyl)-7-fluoro-8-(6-fluoro-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
467 7-Fluoro-8-(1H-indol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
468 7-Fluoro-8-(6-fluoro-1H-indol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
469 8-[1-(2,2-Difluoro-ethyl)-6-fluoro-1H-indazol-4-yl]-1,4,4,9-tetramethyl-7-(trifluoromethyloxy)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
470 7-Fluoro-1,4,4,9-tetramethyl-8-[6-(trifluoromethyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
471 2-[6-Fluoro-4-[1,4,4,9-tetramethyl-7-(trifluoromethyloxy)-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-1H-indol-1-yl]-ethanol;
472 8-[1-(2,2-Difluoro-ethyl)-6-fluoro-1H-indazol-4-yl]-9-(difluoro-methyl)-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
473 7-Fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-8-[6-(trifluoromethyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
474 7-Fluoro-9-methoxy-1,4,4-trimethyl-8-[6-(trifluoromethyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
475 7-Chloro-1,4,4,9-tetramethyl-8-[6-(trifluoromethyl)-1H-indol-4-yl]-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
476 7-Fluoro-1,4,4-trimethyl-8-(6-methyl-1-methylsulfonyl-1H-indol-4-yl)-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
477 7-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;
478 9-(Difluoro-methyl)-7-fluoro-1,4,4-trimethyl-8-(6-methyl-1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
479 4-[7-Fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-1H-indole-6-carbonitrile;
480 8-[6-Fluoro-1-(2-methoxy-ethyl)-1H-indazol-4-yl]-1,4,4,9-tetramethyl-7-(trifluoromethyloxy)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
481 9-(Difluoro-methyl)-7-fluoro-1,4,4-trimethyl-8-(1-methyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
482 8-(3-Cyclopropyl-5-fluoro-1H-indol-7-yl)-7-methoxy-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
483 8-(3-Cyclopropyl-5-fluoro-1H-indol-7-yl)-7-fluoro-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
484 7-Fluoro-8-(7-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
485 7-Chloro-8-(3-cyclopropyl-5-fluoro-1H-indol-7-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
486 7-Fluoro-1,4,4,9-tetramethyl-8-(1-methyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
487 7-Fluoro-9-methoxy-1,4,4-trimethyl-8-(1-methyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
488 7-Chloro-1,4,4,9-tetramethyl-8-(1-methyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
489 8-[1-(2,2-Difluoro-ethyl)-6-fluoro-1H-indazol-4-yl]-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
490 7-Fluoro-8-(1H-indazol-4-yl)-9-methoxy-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
491 7-Chloro-1,4,4,9-tetramethyl-8-(6-methyl-1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
492 7,9-Difluoro-1,4,4-trimethyl-8-(6-methyl-1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
493 7-Fluoro-1,4,4,9-tetramethyl-8-(6-methyl-1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
494 4-(7-Fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indole-6-carbonitrile;
495 8-[1-(Cyclopropyl-methylsulfonyl)-1H-indol-4-yl]-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
496 9-(Difluoro-methyl)-7-fluoro-8-(7-fluoro-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
497 7,9-Difluoro-8-(7-fluoro-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
498 1,4,4-Trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
499 8-(6-Fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
500 8-[1-(2,2-Difluoro-ethyl)-1H-indol-4-yl]-7-methoxy-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
501 7,9-Difluoro-8-(7-fluoro-1H-indazol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
502 8-[1-(Cyclopropyl-methylsulfonyl)-1H-indol-4-yl]-9-(difluoro-methyl)-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
503 1,4,4-Trimethyl-8-(3-methyl-1H-indol-7-yl)-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
504 7-Fluoro-8-(7-fluoro-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
505 7-Fluoro-8-(7-fluoro-1H-indol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
506 7-Chloro-8-(7-fluoro-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
507 8-(5-Fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
508 7-Chloro-8-[1-(2,2-difluoro-ethyl)-6-fluoro-1H-indazol-4-yl]-9-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
509 7-Methoxy-1,4,4-trimethyl-8-(1-methyl-1H-indol-4-yl)-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
510 7-Fluoro-8-(1H-indazol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
511 8-(6-Chloro-1H-indol-4-yl)-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
512 9-(Difluoro-methyl)-7-fluoro-1,4,4-trimethyl-8-(7-methyl-1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
513 8-(6-Chloro-1H-indol-4-yl)-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
514 8-(1-Cyclopropyl-1H-indol-4-yl)-9-(difluoro-methyl)-7-fluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
515 9-(Difluoro-methyl)-7-fluoro-8-(5-fluoro-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
516 7-Fluoro-8-(5-fluoro-1H-indol-7-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
517 8-(6-Fluoro-1-methyl-1H-indol-4-yl)-7-methoxy-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
518 7-Fluoro-8-(6-fluoro-1-methyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
519 7-Chloro-8-(6-fluoro-1-methyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
520 9-Fluoro-8-(6-fluoro-1-methyl-1H-indol-4-yl)-1,4,4,7-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
521 9-(Difluoro-methyl)-7-fluoro-8-(6-fluoro-1-methyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
522 8-(6-Fluoro-1-methyl-1H-indol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
523 8-(1-Cyclopropyl-1H-indol-4-yl)-7-methoxy-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
524 7-Fluoro-8-(7-fluoro-1H-indazol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
525 8-(7-Chloro-1-methylsulfonyl-1H-indol-4-yl)-7-fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
526 9-(Difluoro-methyl)-8-(6-fluoro-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
527 9-(Difluoro-methyl)-8-(5-fluoro-3-methyl-1H-indol-7-yl)-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
528 9-(Difluoro-methyl)-1,4,4-trimethyl-8-(1-methylsulfonyl-1H-indol-4-yl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
529 8-(7-Chloro-1H-indol-4-yl)-7,9-difluoro-1,4,4-trimethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
530 8-(7-Chloro-1H-indol-4-yl)-7-fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
531 4-[7-Fluoro-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]-1H-indole-7-carbonitrile;
532 7-Fluoro-8-(6-fluoro-1-methyl-1H-indol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
533 7-Chloro-8-(1-cyclopropyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
534 4-(7-Fluoro-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)-1H-indole-7-carbonitrile;
535 7-Fluoro-8-(7-fluoro-1H-indazol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
536 7-Fluoro-8-(6-methoxy-1-methylsulfonyl-1H-indol-4-yl)-1,4,4-trimethyl-9-(trifluoromethyl)-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
and
537 7-Fluoro-8-(6-methoxy-1-methylsulfonyl-1H-indol-4-yl)-1,4,4,9-tetramethyl-5H-[1,2,4]triazolo[4,3-a]quinoxaline;
in the form of the free compound or a physiologically acceptable salt thereof.

329 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/152,930Filed 20 Jan 2021 · continuation
Priority: EP 1818461320 Jul 2018
Published: US 2021/0139488 A113 May 2021
Granted: 8 Oct 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 29/00
Non-central analgesic, antipyretic or antiinflammatory agents
C07D
Heterocyclic compounds
A61P
Therapeutic uses of medicines

Family

PCT/EP2019/069611Parent of this continuation · filed 22 Jul 2019
US 2021/0139488 A1Pre-grant publication · published 13 May 2021
US 12,110,293 B2This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

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Abstract

A compound according to general formula (I),

wherein
R1 represents H;
C1-10-alkyl;
C3-10-cycloalkyl;
3 to 7 membered heterocycloalkyl;
aryl;
or 5 or 6-membered heteroaryl;
wherein C3-10-cycloalkyl, 3 to 7 membered heterocycloalkyl, aryl and 5 or 6-membered heteroaryl can optionally be bridged via C1-6-alkylene;
R2 represents H;
F;
Cl;
Br;
I;
CN;
C1-10-alkyl;
C3-10-cycloalkyl;
O—C1-10-alkyl;
N(H)(C1-10-alkyl), N(C1-10-alkyl)2;
C(O)—C1-10-alkyl;
C(O)—O—C1-10-alkyl;
C(O)—NH2;
C(O)—N(H)(C1-10-alkyl);
C(O)—N(C1-10-alkyl)2;
O—C3-10-cycloalkyl;
N(H)(C3-10-cycloalkyl), N(C1-10-alkyl)(C3-10-cycloalkyl);
C(O)—C3-10-cycloalkyl;
C(O)—O—C3-10-cycloalkyl;
C(O)—N(H)(C3-10-cycloalkyl) or C(O)—N(C1-10-alkyl)(C3-10-cycloalkyl);
wherein C3-10-cycloalkyl can optionally be bridged via C1-6-alkylene;
R3 represents H;
F;
Cl;
Br;
I;
CN;
C1-10-alkyl;
C3-10-cycloalkyl;
O—C1-10-alkyl;
N(H)(C1-10-alkyl);
N(C1-10-alkyl)2;
C(O)—C1-10-alkyl;
C(O)—O—C1-10-alkyl;
C(O)—NH2;
C(O)—N(H)(C1-10-alkyl);
C(O)—N(C1-10-alkyl)2;
O—C3-10-cycloalkyl;
N(H)(C3-10-cycloalkyl), N(C1-10-alkyl)(C3-10-cycloalkyl);
C(O)—C3-10-cycloalkyl;
C(O)—O—C3-10-cycloalkyl;
C(O)—N(H)(C3-10-cycloalkyl) or C(O)—N(C1-10-alkyl)(C3-10-cycloalkyl);
wherein C3-10-cycloalkyl can optionally be bridged via C1-6-alkylene;
R5 and R6 represent independently from one another H or unsubstituted C1-4-alkyl;
X represents N or NR7;
Z represents N, NR7 or CR9;
with the proviso that
when X represents NR7, Z represents N or CR9;
when X represents N, Z represents NR7;
R7 represents H or L-R8;
wherein
L represents bond;
S(O);
S(O)2;
C1-6-alkylene;
C(O);
C1-6-alkylene-C(O);
C(O)—O;
C1-6-alkylene-C(O)—O;
C1-6-alkylene-N(H)—C(O);
C1-6-alkylene-N(C1-10-alkyl)-C(O);
C1-6-alkylene-N(H)—C(O)—O;
C1-6-alkylene-N(C1-10-alkyl)-C(O)—O;
O;
NH or N(C1-10-alkyl);
R8 represents C1-10-alkyl;
C3-10-cycloalkyl or 3 to 7 membered heterocycloalkyl;
wherein C3-10-cycloalkyl and 3 to 7 membered heterocycloalkyl can optionally be bridged via C1-6-alkylene;
R9 and R10 represent independently from one another H;
F;
Cl;
Br;
I;
CN;
C1-10-alkyl;
C3-10-cycloalkyl;
3 to 7 membered heterocycloalkyl;
S(O)-(C1-10-alkyl);
S(O)-(C3-10-cycloalkyl);
S(O)-(3 to 7-membered heterocycloalkyl);
S(O)2—(C1-10-alkyl);
S(O)2—(C3-10-cycloalkyl);
S(O)2-(3 to 7-membered heterocycloalkyl);
P(O)-(C1-10-alkyl)2;
P(O)(C1-10-alkyl)(C3-10-cycloalkyl);
P(O)(C1-10-alkyl)(3 to 7-membered heterocycloalkyl);
P(O)—(O—C1-10-alkyl)2;
P(O)(O—C1-10-alkyl)(O—C3-10-cycloalkyl);
P(O)(O—C1-10-alkyl)(O-(3 to 7-membered heterocycloalkyl));
O—C1-10-alkyl;
S—C1-10-alkyl;
N(H)(C1-10-alkyl), N(C1-10-alkyl)2;
C(O)—C1-10-alkyl;
C(O)—O—C1-10-alkyl;
C(O)—NH2;
C(O)—N(H)(C1-10-alkyl);
C(O)—N(C1-10-alkyl)2;
O—C3-10-cycloalkyl;
N(H)(C3-10-cycloalkyl), N(C1-10-alkyl)(C3-10-cycloalkyl);
C(O)—C3-10-cycloalkyl;
C(O)—O—C3-10-cycloalkyl;
C(O)—N(H)(C3-10-cycloalkyl);
C(O)—N(C1-10-alkyl)(C3-10-cycloalkyl);
O-3 to 7-membered heterocycloalkyl;
N(H)(3 to 7-membered heterocycloalkyl), N(C1-10-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(C1-10-alkyl)(3 to 7-membered heterocycloalkyl);
wherein C3-10-cycloalkyl and 3 to 7 membered heterocycloalkyl can optionally be bridged via C1-6-alkylene;
R11 represents F;
Cl;
Br;
I;
CN;
C1-10-alkyl;
O—C1-10-alkyl;
NO2;
OH, NH2;
C3-10-cycloalkyl;
3 to 7-membered heterocycloalkyl;
S(O)-(C1-10-alkyl);
S(O)-(C3-10-cycloalkyl);
S(O)-(3 to 7-membered heterocycloalkyl);
S(O)2—(C1-10-alkyl);
S(O)2—(C3-10-cycloalkyl);
S(O)2-(3 to 7-membered heterocycloalkyl);
P(O)-(C1-10-alkyl)2;
P(O)(C1-10-alkyl)(C3-10-cycloalkyl);
P(O)(C1-10-alkyl)(3 to 7-membered heterocycloalkyl);
P(O)—(O—C1-10-alkyl)2;
P(O)(O—C1-10-alkyl)(O—C3-10-cycloalkyl);
P(O)(O—C1-10-alkyl)(O-(3 to 7-membered heterocycloalkyl));
O—C1-10-alkyl;
N(H)(C1-10-alkyl), N(C1-10-alkyl)2;
C(O)—C1-10-alkyl;
C(O)—O—C1-10-alkyl;
C(O)—NH2;
C(O)—N(H)(C1-10-alkyl);
C(O)—N(C1-10-alkyl)2;
O—C3-10-cycloalkyl;
N(H)(C3-10-cycloalkyl), N(C1-10-alkyl)(C3-10-cycloalkyl);
C(O)—C3-10-cycloalkyl;
C(O)—O—C3-10-cycloalkyl;
C(O)—N(H)(C3-10-cycloalkyl);
C(O)—N(C1-10-alkyl)(C3-10-cycloalkyl);
O-3 to 7-membered heterocycloalkyl;
N(H)(3 to 7-membered heterocycloalkyl), N(C1-10-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(C1-10-alkyl)(3 to 7-membered heterocycloalkyl);
wherein C3-10-cycloalkyl and 3 to 7 membered heterocycloalkyl can optionally be bridged via C1-6-alkylene;
n represents 0, 1, 2 or 3;
wherein C1-10-alkyl, C1-4-alkyl and C1-6-alkylene in each case independently from one another is linear or branched, saturated or unsaturated;
wherein C1-10-alkyl, C1-4-alkyl, C1-6-alkylene, C3-10-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;
C1-6-alkyl;
CF3;
CF2H;
CFH2;
CF2Cl;
CFCl2;
C(O)—C1-6-alkyl;
C(O)—OH;
C(O)—OC1-6-alkyl;
C(O)—NH2;
C(O)—N(H)(C1-6-alkyl);
C(O)—N(C1-6-alkyl)2;
OH;
═O;
OCF3;
OCF2H;
OCFH2;
OCF2Cl;
OCFCl2;
O—C1-6-alkyl;
O—C(O)—C1-6-alkyl;
O—C(O)—O—C1-6-alkyl;
O—(CO)—N(H)(C1-6-alkyl);
O—C(O)—N(C1-6-alkyl)2;
O—S(O)2—NH2;
O—S(O)2—N(H)(C1-6-alkyl);
O—S(O)2—N(C1-6-alkyl)2;
NH2;
N(H)(C1-6-alkyl);
N(C1-6-alkyl)2;
N(H)—C(O)—C1-6-alkyl;
N(H)—C(O)—O—C1-6-alkyl;
N(H)—C(O)—NH2;
N(H)—C(O)—N(H)(C1-6-alkyl);
N(H)—C(O)—N(C1-6-alkyl)2;
N(C1-6-alkyl)-C(O)—C1-6-alkyl;
N(C1-6-alkyl)-C(O)—O—C1-6-alkyl;
N(C1-6-alkyl)-C(O)—NH2;
N(C1-6-alkyl)-C(O)—N(H)(C1-6-alkyl);
N(C1-6-alkyl)-C(O)—N(C1-6-alkyl)2;
N(H)—S(O)2OH;
N(H)—S(O)2—C1-6-alkyl;
N(H)—S(O)2—O—C1-6-alkyl;
N(H)—S(O)2—NH2;
N(H)—S(O)2—N(H)(C1-6-alkyl);
N(H)—S(O)2N(C1-6-alkyl)2;
N(C1-6-alkyl)-S(O)2—OH;
N(C1-6-alkyl)-S(O)2—C1-6-alkyl;
N(C1-6-alkyl)-S(O)2—O—C1-6-alkyl;
N(C1-6-alkyl)-S(O)2—NH2;
N(C1-6-alkyl)-S(O)2—N(H)(C1-6-alkyl);
N(C1-6-alkyl)-S(O)2—N(C1-6-alkyl)2;
SCF3;
SCF2H;
SCFH2;
S—C1-6-alkyl;
S(O)—C1-6-alkyl;
S(O)2—C1-6-alkyl;
S(O)2—OH;
S(O)2—O—C1-6-alkyl;
S(O)2—NH2;
S(O)2—N(H)(C1-6-alkyl);
S(O)2—N(C1-6-alkyl)2;
C3-6-cycloalkyl;
3 to 6-membered heterocycloalkyl;
phenyl;
5 or 6-membered heteroaryl;
O—C3-6-cycloalkyl;
O-(3 to 6-membered heterocycloalkyl);
O-phenyl;
O-(5 or 6-membered heteroaryl);
C(O)—C3-6-cycloalkyl;
C(O)-(3 to 6-membered heterocycloalkyl);
C(O)-phenyl;
C(O)-(5 or 6-membered heteroaryl);
S(O)2—(C3-6-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;
C1-6-alkyl;
CF3;
CF2H;
CFH2;
CF2Cl;
CFCl2;
C1-4-alkylene-CF3;
C1-4-alkylene-CF2H;
C1-4-alkylene-CFH2;
C(O)—C1-6-alkyl;
C(O)—OH;
C(O)—OC1-6-alkyl;
C(O)—N(H)(OH);
C(O)—NH2;
C(O)—N(H)(C1-6-alkyl);
C(O)—N(C1-6-alkyl)2;
OH;
OCF3;
OCF2H;
OCFH2;
OCF2Cl;
OCFCl2;
O—C1-6-alkyl;
O—C3-6-cycloalkyl;
O-(3 to 6-membered heterocycloalkyl);
NH2;
N(H)(C1-6-alkyl);
N(C1-6-alkyl)2;
N(H)—C(O)—C1-6-alkyl;
N(C1-6-alkyl)-C(O)—C1-6-alkyl;
N(H)—C(O)—NH2;
N(H)—C(O)—N(H)(C1-6-alkyl);
N(H)—C(O)—N(C1-6-alkyl)2;
N(C1-6-alkyl)-C(O)—N(H)(C1-6-alkyl);
N(C1-6-alkyl)-C(O)—N(C1-6-alkyl)2;
N(H)—S(O)2—C1-6-alkyl;
SCF3;
S—C1-6-alkyl;
S(O)—C1-6-alkyl;
S(O)2—C1-6-alkyl;
S(O)2—NH2;
S(O)2—N(H)(C1-6-alkyl);
S(O)2—N(C1-6-alkyl)2;
C3-6-cycloalkyl;
C1-4-alkylene-C3-6-cycloalkyl;
3 to 6-membered heterocycloalkyl;
C1-4-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.

295 more elements

Facts

Application

17/152,930Filed 20 Jan 2021 · continuation

Priority

EP 1818461320 Jul 2018

Published

US 2021/0139488 A113 May 2021

Granted

8 Oct 2024

Term ends

Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 29/00
Non-central analgesic, antipyretic or antiinflammatory agents
C07D
Heterocyclic compounds
A61P
Therapeutic uses of medicines