Enantiomers of 3-heteroaryl-8H-8-azabicyclo(3.2.1)oct-2-ene and their use as monoamine neurotransmitter re-uptake inhibitors
This invention relates to novel enantiomers useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.
1. An enantiopure chemical compound or a pharmaceutically acceptable salt thereof, wherein said compound is 3-(2-benzothienyl)-8H-8-azabicyclo[3.2.1]oct-2-ene.
2. An enantiopure chemical compound of
3-(7-fluoro-benzo[b]thiophen-2-yl)-8-aza-bicyclo[3.2.1]oct-2-ene;
3-(7-chloro-benzo[b]thiophen-2-yl)-8-aza-bicyclo[3.2.1]oct-2-ene;
3-(2-benzothienyl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;
3-(7-fluoro-benzo[b]thiophen-2-yl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene;
or a pharmaceutically acceptable salt thereof.
3. The chemical compound of claim 1 , being enantiopure (+)-3-(2-benzothienyl)-8H-8-azabicyclo[3.2.1]oct-2-ene;
or a pharmaceutically acceptable salt thereof.
4. The chemical compound of claim 1 , being enantiopure (−)-3-(2-benzothienyl)-8H-8-azabicyclo[3.2.1]oct-2-ene;
or a pharmaceutically acceptable salt thereof.
5. The chemical compound of claim 2 , being
enantiopure (+)-3-(7-fluoro-benzo[b]thiophen-2-yl)-8-aza-bicyclo[3.2.1]oct-2-ene;
enantiopure (−)-3-(7-fluoro-benzo[b]thiophen-2-yl)-8-aza-bicyclo[3.2.1]oct-2-ene;
enantiopure (−)-3-(7-chloro-benzo[b]thiophen-2-yl)-8-aza-bicyclo[3.2.1]oct-2-ene;
enantiopure (+)-3-(2-benzothienyl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;
enantiopure (+)-3-(2-benzothienyl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;
enantiopure (+)-3-(7-fluoro-benzo[b]thiophen-2-yl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene;
enantiopure (−)-3-(7-fluoro-benzo[b]thiophen-2-yl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene;
or a pharmaceutically acceptable salt thereof.
6. A pharmaceutical composition, comprising a therapeutically effective amount of a compound of claim 2 , or a pharmaceutically acceptable salt thereof, together with at least one pharmaceutically acceptable carrier, excipient or diluent.
7. A method for treatment of a disease or a disorder or a condition of a living animal body, including a human, which disorder, disease, or condition is depression or pain, which method comprises the step of administering to the living animal body in need thereof a therapeutically effective amount of a compound according to claim 2 , or a pharmaceutically acceptable salt thereof.
8. The chemical compound of claim 2 or the pharmaceutically acceptable salt thereof, wherein the enantiopure compound is in enantiomeric excess of at least 99.0% over the opposite enantiomer.
9. A pharmaceutical composition, comprising a therapeutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof, together with at least one pharmaceutically acceptable carrier, excipient or diluent.
10. A method for treatment of a disease or a disorder or a condition of a living animal body, including a human, which disorder, disease, or condition is depression or pain, which method comprises the step of administering to the living animal body in need thereof a therapeutically effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.
11. The chemical compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein the enantiopure compound is in enantiomeric excess of at least 99.0% over the opposite enantiomer.