Amides of acetic and propionic acids
View Patent ↗The invention relates to novel amides of acetic and propionic acids, methods for production and use thereof for the production of medicaments for the treatment and/or prophylaxis of diseases and for improving perception, concentration, learning ability and memory.
1. A compound of the formula (I)
in which
R 1 is 1-azabicyclo[2.2.2]oct-3-yl optionally substituted by (C 1 -C 6 )-alkyl,
A is methylene or ethylene,
R 2 is benzothiophenyl optionally substituted by radicals selected from the group of halogen, formyl, —CO—NR 4 R 5 , —CO—OR 6 , —NR 7 R 8 , —NR 9 —CO—R 10 , cyano, trifluoromethyl, trifluoromethoxy, nitro, optionally hydroxyl-, amino-, —NH—CO—R 11 - or cyano-substituted (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylthio, in which R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are independently of one another hydrogen, (C 1 -C 6 )-alkyl, phenyl or benzyl, and
R 3 is hydrogen or (C 1 -C 6 )-alkyl,
or a salt thereof.
2. A compound as claimed in claim 1 , where
R 1 is 1-azabicyclo[2.2.2]oct-3-yl,
and R 2 and R 3 have the meaning indicated in claim 1 ,
or a salt thereof.
3. A compound as claimed in claim 1 , where
R 1 is 1-azabicyclo[2.2.2]oct-3-yl,
A is methylene,
R 2 is benzothiophenyl where the rings are optionally substituted by 1 to 3 radicals selected from the group of hydrogen, halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylthio, and
R 3 is hydrogen,
or a salt thereof.
4. A compound as claimed in claim 1 , where
R 1 is 1-azabicyclo[2.2.2]oct-3-yl,
A is methylene,
R 2 is benzothiophenyl, where the rings are optionally substituted by 1 to 2 radicals selected from the group of hydrogen, fluorine, chlorine, bromine, nitro and
R 3 is hydrogen,
or a salt thereof.
5. A process for preparing a compound of formula (I) as claimed in claim 1 , characterized in that a compound of formula (II)
in which
R 1 and A have the meaning indicated in claim 1 , and
X is hydroxy or a suitable leaving group,
is reacted with a compound, of formula (III)
R 2 R 3 NH (III),
in which R 2 and R 3 have the meaning indicated in claim 1 ,
and the resulting compound is optionally converted with an appropriate acid or base into a salt thereof.
6. A pharmaceutical composition comprising at least one compound as claimed in claim 1 in combination with at least one pharmaceutically acceptable, essentially nontoxic carrier or excipient.
7. A method for producing a pharmaceutical composition for improving perception, concentration, learning and/or memory comprising the step of mixing at least one compound as claimed in claim 1 with at least one pharmaceutically acceptable, essentially nontoxic carrier or excipient.
8. A method for the treatment and/or prophylaxis of impairments of perception, concentration, learning and/or memory comprising administering to a subject an effective amount of at least one compound as claimed in claim 1 .
9. A method for the treatment and/or prophylaxis of impairments of perception, concentration, learning and/or memory comprising administering to a subject an effective amount of the pharmaceutical composition as claimed in claim 6 .