Heterocyclic compounds with working memory enhancing activity
The present disclosure relates to a chemical compound having the general formula wherein R 1 and R 2 are, equal or independently, aryl, heteroaryl; wherein R TA is a 2-1,3-, or 4-1,3- or 5-1,3-thiazole ring and its use in for improving the short term memory and/or the working memory.
1. Chemical compound having the general formula (I):
wherein R 1 and R 2 are, equal or independently, aryl or substituted aryl;
R TA is a 2-1,3-, or 4-1,3- or 5-1,3-thiazole ring with the general Formula (IIa):
R 3 is present on the ring according to Formula (IIa), 1 or 2 times, equal or independently,
wherein R 3 is selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocycloalkyl, halo, and alkoxy.
2. Compound according to claim 1 , wherein
R TA is a 4-thiazole group, 2-thiazole, and 2-methyl-4-thiazole.
3. Compound according to claim 1 , wherein
alkyl is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl and tert-butyl, or wherein hydroxyalkyl is hydroxymethyl.
4. Compound according to claim 1 , wherein
R 3 is hydrogen or alkyl or oxyalkyl.
5. Compound according to claim 1 , wherein
it is selected from the group consisting of
2-(diphenylmethanesulfinylmethyl)-1,3-thiazole,
4-(diphenylmethanesulfinylmethyl)-1,3-thiazole,
2-(diphenylmethanesulfinylmethyl)-4-methyl-1,3-thiazole, and
4-(diphenylmethanesulfinylmethyl)-2-methyl-1,3-thiazole.
6. Compound according to claim 5 , wherein
it is 4-(diphenylmethanesulfinylmethyl)-2-methyl-1,3-thiazole.
7. Compound according to claim 1 , wherein
R 1 and R 2 are, equal or independently, aryl or substituted aryl,
wherein R 3 is present on R TA according to Formula (IIa) 2 times and selected from the group consisting of R 4 , R 5 , R 6 and R 7 ,
wherein R TA is a 4-1,3-thiazole ring with the general Formula (Ma)
wherein R 4 is selected from the group consisting of oxirane, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl and
wherein R 5 is selected from the group consisting of hydrogen, methyl, n-propyl, iso-propyl,
or
wherein R TA is a 5-1,3-thiazole ring with the general Formula (IIIb)
wherein R 6 is selected from the group consisting of hydrogen, methyl, n-propyl, iso-propyl, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, and
wherein R 7 is selected from the group consisting of hydrogen, methyl, n-propyl, iso-propyl, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
8. Compound according to claim 4 , wherein
R 3 is methyl or oxymethyl.
9. Compound according to claim 1 ,
wherein R 1 and R 2 are, equal or independently, aryl or substituted aryl,
wherein R TA is a 4-1,3-thiazole ring with the general Formula (Ma)
wherein R 4 is selected from the group consisting of oxirane, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl and
wherein R 5 is selected from the group consisting of hydrogen, methyl, n-propyl, iso-propyl, fluoro, chloro, bromo and iodo,
or
wherein R TA is a 5-1,3-thiazole ring with the general Formula (Mb)
wherein R 6 is selected from the group consisting of hydrogen, methyl, n-propyl, iso-propyl, fluoro, chloro, bromo, iodo, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, and
wherein R 7 is selected from the group consisting of hydrogen, methyl, n-propyl, iso-propyl, fluoro, chloro, bromo, iodo, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
10. Compound according to claim 9 , wherein
both of R 1 and R 2 are phenyl.
11. Compound according to claim 9 , wherein
R 4 is cyclopropyl and wherein R 5 is hydrogen.
12. Compound according to claim 9 , wherein
both R 6 and R 7 are hydrogen.
13. Compound according to claim 9 , wherein
it is selected from the group consisting of
5-(diphenylmethanesulfinylmethyl)-1,3-thiazole,
5-(diphenylmethanesulfinylmethyl)-2-chloro-1,3-thiazole,
5-(diphenylmethanesulfinylmethyl)-2-methyl-1,3-thiazole,
5-(diphenylmethanesulfinylmethyl)-4-methyl-1,3-thiazole,
5-(diphenylmethanesulfinylmethyl)-4-chloro-1,3-thiazole,
5-(diphenylmethanesulfinylmethyl)-2-methyl-4-methyl-1,3-thiazole,
5-(diphenylmethanesulfinylmethyl)-2-methyl-4-chloro-1,3-thiazole,
5-(diphenylmethanesulfinylmethyl)-2-chloro-4-methyl-1,3-thiazole,
5-(diphenylmethanesulfinylmethyl)-2-cyclopropyl-1,3-thiazole,
4-(diphenylmethanesulfinylmethyl)-2-oxirane-1,3-thiazole,
4-(diphenylmethanesulfinylmethyl)-2-cyclopropyl-5-methyl-1,3-thiazole,
4-(diphenylmethanesulfinylmethyl)-2-cyclopropyl-5-chloro-1,3-thiazole, and
4-(diphenylmethanesulfinylmethyl)-2-cyclopropyl-1,3-thiazole.
14. Compound according to claim 9 , wherein
it is 4-(diphenylmethanesulfinylmethyl)-2-cyclopropyl-1,3-thiazole or 5-(diphenylmethanesulfinylmethyl)-1,3-thiazole.