Benzenesulfonanilide compounds suitable for treating disorders that respond to modulation of the serotonin 5-HT
View Patent ↗The present invention relates to novel benzenesulfonanilide compounds of the formulae I and I′ and physiologically tolerated acid addition salts and the N-oxides thereof. The compounds possess valuable therapeutic properties and are particularly suitable, for treating diseases that respond to modulation of the serotonin 5-HT 6 receptor. wherein n is 1 or 2; R 1 is hydrogen or methyl and is positioned vicinal to the radical R 1 ; R 2 is hydrogen or methyl; R 3 is C 1 -C 3 alkyl; R 4 is hydrogen, C 1 -C 4 alkyl, cyclopropyl, C 3 -C 4 cycloalkylmethyl or fluorinated C 1 -C 4 alkyl; R 5 is hydrogen, fluorine, chlorine, C 1 -C 4 alkyl, fluorinated C 1 -C 4 alkyl, C 1 -C 4 alkoxy or fluorinated C 1 -C 4 alkoxy; and R 6 is hydrogen, fluorine or chlorine.
1. A benzenesulfonanilide compound of formulae I and I′
wherein
n is 1 or 2;
R′ is hydrogen or methyl;
R 2 is hydrogen or methyl;
R 3 is C 1 -C 3 alkyl;
R 4 is hydrogen, C 1 -C 4 alkyl, cyclopropyl, C 3 -C 4 cycloalkylmethyl or fluorinated C 1 -C 4 alkyl;
R 5 is hydrogen, fluorine, C 1 -C 4 alkyl, fluorinated C 1 -C 4 alkyl, C 1 -C 4 alkoxy or fluorinated C 1 -C 4 alkoxy; and
R 6 is hydrogen, fluorine or chlorine;
wherein R 2 is positioned vicinal to the radical R 1 ;
and physiologically tolerated acid addition salts and the N-oxides thereof.
2. The compound of claim 1 , wherein R 1 is hydrogen.
3. The compound of claim 1 , wherein R 2 is hydrogen.
4. The compound of claim 1 , wherein R 2 is methyl.
5. The compound of claim 4 , wherein the carbon atom that carries R 2 has S-configuration.
6. The compound of claim 4 , wherein the carbon atom that carries R 2 has R-configuration.
7. The compound of claim 1 , wherein R 3 is methyl.
8. The compound of claim 1 , wherein R 4 is hydrogen or C 1 -C 3 alkyl.
9. The compound of claim 1 , wherein R 5 is hydrogen.
10. The compound of claim 1 , wherein R 5 is methyl, methoxy or difluoromethoxy.
11. The compound of claim 1 , wherein R 6 is hydrogen.
12. The compound of claim 1 , wherein R 2 , R 5 and R 6 are hydrogen, R 3 is methyl and R 4 is hydrogen or C 1 -C 3 alkyl.
13. The compound of claim 1 , wherein the OCHF 2 -radical in formula I is located on the benzene ring in the ortho-position with respect to the sulfonyl group.
14. The compound of claim 1 , wherein the OCHF 2 -radical in formula I is located on the benzene ring in the meta-position with respect to the sulfonyl group.
15. The compound of claim 1 , wherein the OCHF 2 -radical in formula I is located on the benzene ring in the para-position with respect to the sulfonyl group.
16. A pharmaceutical composition comprising at least one compound of claim 1 , together with at least one physiologically acceptable carrier or auxiliary substance.
17. A method for treating a disorder selected from the group consisting of obesity, depression, cognitive dysfunction associated with Alzheimer's disease, and cognitive dysfunction associated with schizophrenia, the method comprising administering to a subject in need thereof a compound of formula (I) or (I′),
wherein
n is 1 or 2;
R 1 is hydrogen or methyl;
R 2 is hydrogen or methyl;
R 3 is C 1 -C 3 alkyl;
R 4 is hydrogen, C 1 -C 4 alkyl, cyclopropyl, C 3 -C 4 cycloalkylmethyl or fluorinated C 1 -C 4 alkyl;
R 5 is hydrogen, fluorine, C 1 -C 4 alkyl, fluorinated C 1 -C 4 alkyl, C 1 -C 4 alkoxy or fluorinated C 1 -C 4 alkoxy; and
R 6 is hydrogen, fluorine or chlorine;
wherein R 2 is positioned vicinal to the radical R 1 ;
and physiologically tolerated acid addition salts and the N-oxides thereof.