Claims
- 1. A compound of Formula I: wherein:Ar1 and Ar2 are independently selected aryl groups, optionally substituted with up to five substituents independently selected from the group consisting of alkyl, alkoxy, cycloalkyl, cycloalkyloxy, alkanoyl, thioalkyl, aralkyl, aralkyloxy, aryloxyalkyl, aryloxyalkoxy, cycloalkyl-substituted alkyl, cycloalkyloxy-substituted alkyl, cycloalkyl-substituted alkoxy, cycloalkyloxy-substituted alkoxy, thioaryl, aralkylthio, thioaryl-alkyl, aralkylthioalkyl, halo, NO2, CF3, CN, OH, alkylenedioxy, SO2NRR′, NRR′, CO2R (where R and R′ are independently selected from the group consisting of H and alkyl), and a second aryl group, which may be substituted as above, wherein the aryls of the substitutions are carbocyclic; R1 is selected from the group consisting of H and alkyl; R2 is selected from the group consisting of H, alkyl and benzyl; R3 is selected from the group consisting of CO2R, CONRR′, CONH(OH), COSR, SO2NRR′, PO(OR)(OR′) and tetrazolyl, wherein R and R′ are independently selected from the group consisting of H and alkyl; and a salt, solvate or hydrate thereof.
- 2. A compound according to claim 1, wherein Ar1 is an aryl group, optionally substituted with up to three substituents independently selected from halo, NO2, CF3, CN, OH, SO2NRR′, NRR′, CO2R (where R and R′ are independently selected from the group consisting of H and alkyl), and a substituent of the formula R″—(X)n— whereinn is 0 or 1; X is CH2 or a heteroatom; R″ is H, alkyl and aryl substituted optionally with up to three substituents selected from alkyl, halo, NO2, CF3, CN, OH, SO2NRR′, NRR′ and CO2R, wherein R and R′ are independently selected from the group consisting of H and alkyl.
- 3. A compound according to claim 2, wherein Ar1 is phenyl.
- 4. A compound according to claim 2, wherein Ar1 is substituted phenyl.
- 5. A compound according to claim 4, wherein Ar1 is lower alkyl substituted phenyl.
- 6. A compound according to claim 5, wherein Ar1 is 4-(alkyl)-phenyl.
- 7. A compound according to claim 6, wherein said alkyl group is selected from methyl, ethyl, n-propyl, isopropyl and n-butyl.
- 8. A compound according to claim 1, wherein Ar1 is alkylenedioxyphenyl.
- 9. A compound according to claim 8, wherein Ar1 is methylendioxyphenyl.
- 10. A compound according to claim 9, wherein Ar1 is 3,4-methylenedioxyphenyl.
- 11. A compound according to claim 1, wherein Ar1 is a benzo-fused aromatic group.
- 12. A compound according to claim 11, wherein Ar1 is carbocyclic.
- 13. A compound according to claim 12, wherein Ar1 is naphthyl.
- 14. A compound according to claim 13, wherein Ar1 is 2-naphthyl.
- 15. A compound according to claim 1, wherein Ar2 is an aryl group optionally substituted with up to three substituents independently selected from halo, haloalkyl, alkyl, haloalkoxy, and alkoxy.
- 16. A compound according to claim 15 in which Ar2 is unsubstituted aryl.
- 17. A compound according to claim 16 in which Ar2 is phenyl.
- 18. A compound according to claim 15, wherein Ar2 is substituted phenyl.
- 19. A compound according to claim 18, wherein Ar2 is halo-substituted phenyl.
- 20. A compound according to claim 19, wherein Ar2 is phenyl substituted by chloro or fluoro.
- 21. A compound according to claim 1, wherein R1 is H.
- 22. A compound according to claim 1, wherein R2 is H.
- 23. A compound according to claim 22, wherein R3 is methyl.
- 24. A compound according to claim 1, wherein R3 is COOR.
- 25. A compound according to claim 24, wherein R3 is COOH.
- 26. A compound according to claim 1, selected from:N-(5-(4-Fluorophenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(2-Fluorophenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(2,4-Difluorophenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(3-Nitrophenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Nitrophenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(3-Phenyl-5-(2-thiomethylphenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Chlorophenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Isopropylphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine, N-(5-(3,5-Bis(trifluoromethyl)phenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(3,5-Diphenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-diphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-trifluoromethylphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-benzylphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-ethylphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-npropylphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-nbutylphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-npentylphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-phenoxyphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(1-naphthyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-methylphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(3-isopropylphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(2-naphthyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(3,4-dimethylphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(2-isopropylphenyl)-3-phenyl-2-penten4-yn-1-yl)-sarcosine N-(5-(3,4-methylenedioxyphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-trifluoromethoxyphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(5-(3,4-dimethoxyphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(3-Phenyl-5-(4-thiomethylphenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Methylphenyl)-3-phenyl-2-penten-4-yn-1-yl)-sarcosine N-(3-Phenyl-5-(4-t-butylphenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Isopropylphenyl)-3-(4-(trifluoromethyl)phenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Isopropylphenyl)-3-(4-fluorophenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Isopropylphenyl)-3-(2-fluorophenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-t-Butylphenyl)-3-(2-fluorophenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Isopropylphenyl)-3-(4-chlorophenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-t-Butylphenyl)-3-(4-chlorophenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Isopropylphenyl)-3-(2-chlorophenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-t-Butylphenyl)-3-(2-chlorophenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Isopropylphenyl)-3-(3-fluorophenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Isopropylphenyl)-3-(4-methoxyphenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(3,4-Methylenedioxyphenyl)-3-(3-fluorophenyl)-2-penten-4-yn-1-yl)-sarcosine N-(5-(4-Ethylphenyl)-3-(2-chlorophenyl)-2-penten-4-yn-1-yl)-sarcosine, and N-(5-(4-Propylphenyl)-3-(2-chlorophenyl)-2-penten-4-yn-1-yl)-sarcosine.
- 27. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1, and a pharmaceutically acceptable carrier.
- 28. A method for treating a patient having a medical condition for which a glycine transport inhibitor is indicated, comprising the step of ministering to the patient a pharmaceutical composition as defined in claim 27.
- 29. A method according to claim 28 in which the medical condition is schizophrenia.
- 30. A method according to claim 28 in which the medical condition is cognitive dysfunction.
- 31. A method according to claim 28 in which the medical condition is Alzheimer's disease.
Parent Case Info
This application claims the benifit of Provisional Application No. 60/162,986, filed Nov. 1, 1999.
Non-Patent Literature Citations (1)
Entry |
Greenhill, Chemical Abstracts, vol. 73, No. 425, 067 (1976). |
Provisional Applications (1)
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Number |
Date |
Country |
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60/162986 |
Nov 1999 |
US |