Patent
Novel compounds of Formula I and their use in therapeutic treatments.
1. A compound of Formula I:
or a pharmaceutically acceptable solvate thereof, wherein:
R 1 is H or F;
R 1′ is H;
R 2 is H, F or Cl;
R 2′ is H or F;
R 3 is F or Cl;
R 4 is methyl, trifluoromethyl, difluoromethyl or fluoromethyl;
X 1 is N and X 2 is S; or X 1 is S and X 2 is N; and
represents a single or a double bond depending on X 1 and X 2 .
2. The compound according to claim 1 , having Formula Ia:
or a pharmaceutically acceptable solvate thereof, wherein:
R 1 is H or F;
R 1′ is H;
R 2 is H, F or Cl;
R 2′ is H or F;
R 3 is F or Cl; and
R 4 is methyl, trifluoromethyl, difluoromethyl or fluoromethyl.
3. The compound according to claim 1 , having Formula Ia-1:
or a pharmaceutically acceptable solvate thereof, wherein:
R 3 is F or Cl; and
R 4 is methyl, trifluoromethyl, difluoromethyl or fluoromethyl.
4. The compound according to claim 1 , having Formula Ia-2:
or a pharmaceutically acceptable solvate thereof, wherein:
R 1 is H or F;
R 1′ is H;
R 2 is H, F or Cl;
R 2′ is H or F; and
R 3 is F or Cl.
5. The compound according to claim 1 , having Formula Ib:
or a pharmaceutically acceptable solvate thereof, wherein:
R 1 is H or F;
R 1′ is H;
R 2 is H, F or Cl;
R 2′ is H or F;
R 3 is F or Cl; and
R 4 is methyl, trifluoromethyl, difluoromethyl or fluoromethyl.
6. The compound according to claim 1 , selected from the group consisting of:
(4-fluorophenyl) (3-(3-methyl-1,2,4-thiadiazol-5-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone;
(4-chlorophenyl) (3-(3-methyl-1,2,4-thiadiazol-5-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone;
(4-chloro-3-fluorophenyl)(3-(3-methyl-1,2,4-thiadiazol-5-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone;
(3-chloro-4-fluorophenyl)(3-(3-methyl-1,2,4-thiadiazol-5-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone;
(3,4-difluorophenyl) (3-(3-methyl-1,2,4-thiadiazol-5-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone;
(3-(3-methyl-1,2,4-thiadiazol-5-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl) (3,4,5-trifluorophenyl)methanone;
(3-(3-methyl-1,2,4-thiadiazol-5-yl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl) (2,3,4-trifluorophenyl)methanone;
and a pharmaceutically acceptable solvate thereof.
7. A pharmaceutical composition or a medicament comprising a compound of Formula I
or a pharmaceutically acceptable solvate thereof, wherein:
R 1 is H or F;
R 1′ is H;
R 2 is H, F or Cl;
R 2′ is H or F;
R 3 is F or Cl;
R 4 is methyl, trifluoromethyl, difluoromethyl or fluoromethyl;
X 1 is N and X 2 is S; or X 1 is S and X 2 is N; and
represents a single or a double bond depending on X 1 and X 2 ;
and at least one pharmaceutically acceptable carrier, diluent, excipient and/or adjuvant.
8. A method for treating depression, anxiety, schizophrenia, pain, and benign prostatic hyperplasia (BPH), comprising the administration, to a patient in need thereof, of a pharmaceutically effective amount of a compound of Formula I
or a pharmaceutically acceptable solvate thereof, wherein:
R 1 is H or F;
R 1′ is H;
R 2 is H, F or Cl;
R 2′ is H or F;
R 3 is F or Cl;
R 4 is methyl, trifluoromethyl, difluoromethyl or fluoromethyl;
X 1 is N and X 2 is S; or X 1 is S and X 2 is N; and
represents a single or a double bond depending on X 1 and X 2 .
9. A method for treating hot flashes, comprising the administration, to a patient in need thereof, of a pharmaceutically effective amount of a compound of Formula I
or a pharmaceutically acceptable solvate thereof, wherein:
R 1 is H or F;
R 1′ is H;
R 2 is H, F or Cl;
R 2′ is H or F;
R 3 is F or Cl;
R 4 is methyl, trifluoromethyl, difluoromethyl or fluoromethyl;
X 1 is N and X 2 is S; or X 1 is S and X 2 is N; and
represents a single or a double bond depending on X 1 and X 2 .