Alkyl substituted indoloquinoxalines
Novel substituted indoloquinoxalines of formula wherein R 1 is hydrogen or represents one or more similar or different substituents in the positions 7 to 10 selected from the group halogen, lower alkyl/alkoxy, hydroxy, trifluoromethyl, trichloromethyl, trifluoromethoxy, R 2 represents similar or different C 1 -C 4 alkyl substituents, X is CO or CH 2 , Y is OH, NH 2 , NH—(CH 2 ) n —R 3 wherein R 3 represents lower alkyl, OH, NH 2 , NHR 4 or NR 5 R 6 wherein R 4 , R 5 and R 6 independently are lower alkyl or cyclo-alkyl and n is an integer of from 2 to 4, with the provision that when X is CH 2 , Y is OH or NH—(CH 2 ) n —OH, and pharmacologically acceptable salts thereof are described. The compounds are useful as drugs for preventing and/or treating autoimmune diseases.
1. A compound of formula (I)
wherein
R 1 is hydrogen or represents one or more similar or different substituents in the positions 7 to 10 selected from the group halogen, lower alkyl/alkoxy, hydroxy, trifluoromethyl, trichloromethyl, trifluoromethoxy,
R 2 represents similar or different C 1 -C 4 alkyl substituents,
X is CO or CH 2 ,
Y is OH, NH 2 , NH—(CH 2 ) n —R 3 wherein R 3 represents lower alkyl, OH, NH 2 , NHR 4 or NR 5 R 6 wherein R 4 , R 5 and R 6 independently are lower alkyl or cyclo-alkyl and n is an integer of from 2 to 4,
with the provision that when X is CH 2 , Y is OH or NH—(CH 2 ) n —OH,
or a pharmacologically acceptable salt thereof.
2. The compound according to claim 1 wherein X is CO and Y is OH or NH 2 and R 1 is a halogen atom.
3. The compound according to claim 1 wherein R 1 is a chloro or fluoro atom.
4. The compound according to claim 1 wherein X is CO and Y is NH—CH 2 —CH 2 —R 3 wherein R 3 is NH 2 or N(CH 3 ) 2 .
5. The compound according to claim 1 wherein R 2 is methyl in positions 2 and 3.
6. A pharmaceutical composition which contains a compound of formula (I) according to claim 1 together with optional solvents, carriers and adjuvants.
7. The compound according to claim 2 wherein R 1 is a chloro or fluoro atom.
8. Previously Presented according to claim 4 wherein R 2 is methyl in positions 2 and 3.
9. The compound according to claim 7 wherein R 2 is methyl in positions 2 and 3.
10. A pharmaceutical composition comprising a compound in accordance with claim 9 together with at least one pharmaceutically acceptable solvent, carrier or adjuvant.
11. A compound selected from the group consisting of:
2,3-Dimethylindolo[2,3-b]quinoxaline-6-yl-acetamide;
9-Chloro-2,3-dimethyl-indolo[2,3-b]quinoxaline-6-yl-acetamide;
2,3-Dimethyl-9-fluoro-indolo[2,3-b]quinoxaline-6-yl-acetamide;
2,3-Dimethyl-6-(N,N-dimethylaminoethylamino-2-oxoethyl)-6H-indolo[2,3-b]quinoxaline;
9-Chloro-2,3-dimethyl-6-(N,N-dimethylaminoethylamino-2-oxoethyl)-6H-indolo-[2,3-b]quinoxaline;
9-Chloro-2,3-dimethyl-6-(aminoethylamino-2-oxoethyl)-6H-indolo[2,3-b]quinoxaline;
2,3-Dimethyl-6-(aminoethylamino-2-oxoethyl)-9-fluoro-6H-indolo[2,3-b]quinoxaline;
2,3-Dimethyl-9-chloro-indolo[2,3-b]quinoxaline-6-yl acetic acid; and
2,3-dimethyl-9-fluoro-indolo[2,3-b]quinoxaline-6-yl-acetic acid, or a pharmaceutically acceptable salt thereof.
12. A pharmaceutical composition comprising a compound according to claim 11 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.
13. The compound 9-Chloro-2,3-dimethyl-6-(N,N-dimethylaminoethylamino-2-oxoethyl)-6H-indolo-[2,3-b]quinoxaline or a pharmaceutically acceptable salt thereof, according to claim 11 .
14. A pharmaceutical composition comprising 9-Chloro-2,3-dimethyl-6-(N,N-dimethylaminoethylamino-2-oxoethyl)-6H-indolo-[2,3-b]quinoxaline or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient, according to claim 11 .