Claims
- 1. A compound of the formula (I):
- 2. The compound of claim 1, wherein R1 is hydrogen.
- 3. The compound of claim 1, wherein R4 is selected from chlorine, O—R5, and S—R5.
- 4. The compound of claim 3, wherein R5 is selected from aryl-C1-6-alkyl, aryloxy-C2-6-alkyl, heteroaryl-C1-6-alkyl, heteroaryloxy-C2-6-alkyl, C3-6-cycloalkyl, C3-6-cycloalkyl-C1-4-alkyl, C1-6-alkyl, 2-tetrahydrofurfuryl, and wherein any aryl or heteroaryl residue, alone or as part of another group, may be unsubstituted or substituted with one or more of C1-4-alkyl, C1-4-alkoxy, cyano, halogen, or aryloxy-C1-4-alkyl.
- 5. The compound of claim 4, wherein R5 is selected from benzyl, 2-chlorobenzyl, 3-cyanobenzyl, 2-cyclohexylethyl, cyclopentyl, 2-cyclopentylethyl, 2,3-difluorobenzyl, 2,6-difluorobenzyl, 2-(2,6-difluorophenoxy)ethyl, 2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl, ethyl, 5-fluoro-2-methoxybenzyl, furan-2-ylmethyl, methyl, α-methylbenzyl, 3-methylbenzyl, 2-(naphthalene-2-yloxy)ethyl, 2-phenoxyethyl, 2-phenoxymethylbenzyl, n-propyl, 3-(pyridin-3-yl)-n-propyl, 2-(8-quinolinyloxy)ethyl, tetrahydrofuran-2-ylmethyl, or 3-thienylmethyl.
- 6. The compound of claim 1, wherein the carbon atom, to which R2 is attached, has the (S)-configuration when R2 is methyl and R1 and R3 both are hydrogen.
- 7. The compound of claim 1, wherein the carbon atom, to which R3 is attached, has the (R)-configuration when R3 is methyl and R1 and R2 both are hydrogen
- 8. The compound of claim 1, wherein the compound is
1-(6-Chloro-5-trifluoromethyl-pyridin-2-yl)-3-(S)-methyl-piperazine; 1-(6-Chloro-5-trifluoromethyl-pyridin-2-yl)-3-(R)-methylpiperazine; 1-(6-Chloro-5-trifluoromethyl-pyridin-2-yl)-2-(R)-methyl-piperazine; 1-(6-Chloro-5-trifluoromethyl-pyridin-2-yl)-2-(S)-methyl-piperazine, hydrochloride; 1-[6-(2-Phenoxy-ethoxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 1-[6-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethoxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 1-[6-(Thiophen-3-ylmethoxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 3-(6-Piperazin-1-yl-3-trifluoromethyl-pyridin-2-yloxymethyl)-benzonitrile, acetate; 1-[6-(3-Methyl-benzylsulfanyl)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 1-[6-(2-Chloro-benzylsulfanyl)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 1-[6-(2,3-Difluoro-benzyloxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 1-(6-Ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-piperazine, acetate; 1-(6-Propoxy-5-trifluoromethyl-pyridin-2-yl)-piperazine, acetate; 1-(6-Cyclopentyloxy-5-trifluoromethyl-pyridin-2-yl)-piperazine, acetate; 1-[6-(1-Phenyl-ethoxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 8-[2-(6-Piperazin-1-yl-3-trifluoromethyl-pyridin-2-yloxy)-ethoxy]-quinoline, acetate; 1-[6-(2,6-Difluoro-benzyloxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 1-[6-(3-{Pyridin-3-yl}propoxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 1-(6-Benzyloxy-5-trifluoromethyl-pyridin-2-yl)-piperazine, acetate; 1-[6-(Furan-2-ylmethoxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 1-{6-[2-(2,6-Difluoro-phenoxy)-ethoxy]-5-trifluoromethyl-pyridin-2-yl}-piperazine, acetate; 1-[6-(2-Chloro-benzylsulfanyl)-5-trifluoromethyl-pyridin-2-yl]-2-(R)-methyl-piperazine, acetate; 1-(6-Ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-3-(S)-methyl-piperazine, acetate; 1-(6-Ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-3-(R)-methyl-piperazine, acetate; 1-(6-Ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-2-(R)-methyl-piperazine, acetate; 1-(6-Benzyloxy-5-trifluoromethyl-pyridin-2-yl)-3-(S)-methyl-piperazine, acetate; 1-(6-Benzyloxy-5-trifluoromethyl-pyridin-2-yl)-3-(R)-methyl-piperazine, acetate; 1-(6-Benzyloxy-5-trifluoromethyl-pyridin-2-yl)-2-(R)-methyl-piperazine, acetate; 1-(6-Benzyloxy-5-trifluoromethyl-pyridin-2-yl)-2-(S)-methyl-piperazine, acetate; 1-(6-Methoxy-5-trifluoromethyl-pyridin-2-yl)-piperazine, acetate; 1-[6-(5-Fluoro-2-methoxy-benzyloxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 1-{6-[2-(Naphthalen-2-yloxy)-ethoxy]-5-trifluoromethyl-pyridin-2-yl}-piperazine, acetate; 1-[6-(2-Chloro-benzylsulfanyl)-5-trifluoromethyl-pyridin-2-yl]-3-(S)-methyl-piperazine, acetate; 1-[6-(2-Chloro-benzylsulfanyl)-5-trifluoromethyl-pyridin-2-yl]-2-(S)-methyl-piperazine, acetate; 1-[6-(2-Phenoxymethyl-benzyloxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 1-[6-Tetrahydro-furan-2-ylmethoxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; 1-[6-(2-Cyclopentyl-ethoxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate; or 1-[6-(2-Cyclohexyl-ethoxy)-5-trifluoromethyl-pyridin-2-yl]-piperazine, acetate.
- 9. A pharmaceutical composition comprising a compound of formula (I) of claim 1 and a pharmaceutically acceptable carrier.
- 10. A method for the prophylaxis or treatment of a serotonin-related disorder or condition in a subject in need of such prophylaxis or treatment, the method comprising administering to the subject an effective amount of a compound of formula (I) of claim 1.
- 11. The method of claim 10, wherein the serotonin-related disorder or condition is a 5-HT2c receptor-related disorder or condition.
- 12. The method of claim 11, wherein the 5-HT2c receptor-related disorder or condition is selected from memory disorders, Alzheimer's disease; schizophrenia; mood disorders; anxiety disorders; pain; substance abuse; sexual dysfunction; epilepsy; glaucoma; urinary incontinence; menopausal and post-menopausal hot flushes; type II diabetes; eating disorders, binge eating disorders, anorexia nervosa, bulimia, or weight gain associated with antipsychotic drug administration.
- 13. The method of claim 11, wherein the the 5-HT2c receptor-related disorder or condition is obesity.
- 14. A method for modulating 5-HT2c receptor activity in a subject in need of such modulating, the method comprising administering to the subject an effective amount of a compound of formula (I) of claim 1.
- 15. The method of claim 10, wherein the subject is a human.
- 16. The method of claim 10, wherein the subject is an animal.
- 17. The method of claim 14, wherein the subject is an animal.
- 18. The method of claim 14, wherein the subject is a human.
- 19. A method for preparing a pharmaceutical composition, the method comprising combining a compound of formula (I) of claim 1 with a pharmaceutically acceptable carrier.
- 20. A method of making a compound of formula (I) of claim 1, by reacting a compound of the following formula (II):
Priority Claims (1)
Number |
Date |
Country |
Kind |
0201544-4 |
May 2002 |
SE |
|
RELATED APPLICATIONS
[0001] This application claims priority to Swedish application number 0201544-4, filed on May 17, 2002, and U.S. provisional application 60/410,038, filed on Sep. 12, 2002, the contents of which are incorporated herein by reference.
Provisional Applications (1)
|
Number |
Date |
Country |
|
60410038 |
Sep 2002 |
US |