Novel glycine transporter type-2 reuptake inhibitors. Part 2: β- and γ-amino acid derivatives

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 16, 2004, Pages 4493-4509

  Wolin, Ronald L ^a   Santillán Jr , Alejandro ^a   Barclay, Tristin ^a   Tang, Liu ^a   Venkatesan, Hariharan ^a   Wilson, Sandy ^a   Lee, Doo Hyun ^a   Lovenberg, Timothy W ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (3 BIPHENYL 4 YLUREIDO) 3 PHENYL N (2 PYRROLIDIN 1 YLETHYL)PROPIONAMIDE; 3 (3 BIPHENYL 4 YLUREIDO) 4 METHYLPENTANOIC ACID (2 PYRROLIDIN 1 YLETHYL)PROPIONAMIDE; 3 (3 BIPHENYL 4 YLUREIDO) 4 PHENYL N (2 PYRROLIDIN 1 YLETHYL)BUTYRAMIDE; 3 (3 BIPHENYL 4 YLUREIDO) 5 METHYLHEXANOIC ACID (2 PYRROLIDIN 1 YLETHYL)AMIDE; 3 (3 BIPHENYL 4 YLUREIDO) N (2 DIMETHYLAMINOETHYL) 3 PHENYLPROPIONAMIDE; 3 (3 BIPHENYL 4 YLUREIDO) N (2 DIMETHYLAMINOETHYL) 4 PHENYLBUTYRAMIDE; 3 (3 BIPHENYL 4 YLUREIDO) N (2 ISOPROPYLAMINOETHYL) 3 PHENYLPROPIONAMIDE; 3 (N' BIPHENYL 4 YL N'' CYANOGUANIDINO) 3 PHENYL N (2 PYRROLIDIN 1 YLETHYL)PROPIONAMIDE; 3 (N'' BIPHENYL 4 YL N'' CYANOGUANIDINO) 4 PHENYL N (2 PYRROLIDIN 1 YLETHYL)BUTYRAMIDE; 3 [3 (4 PHENOXYPHENYL)UREIDO] 4 PHENYL N (2 PYRROLIDIN 1 YLETHYL)BUTYRAMIDE; 3 [N' [4 (4 FLUOROPHENOXY)PHENYL N'' CYANOGUANIDINO] 3 PHENYL N (2 PYRROLIDIN 1 YLETHYL)PROPIONAMIDE; 3 [N' CYANO N'' (4 PHENOXYPHENYL)GUANIDINO] 3 PHENYL N (2 PYRROLIDIN 1 YLETHYL)PROPIONAMIDE; 3 [N'' [4 (4 CHLOROPHENOXY)PHENYL] N'' CYANOGUANIDINO] 3 PHENYL N (2 PYRROLIDIN 1 YLETHYL)PROPIONAMIDE; 3 [N'' METHYL N'' (4,4 TOLYLOXYPHENYL)GUANIDINO] 3 PHENYL N (2 PYRROLIDIN 1 YLETHYL)PROPIONAMIDE; 4 (3 BIPHENYL 4 YLUREIDO) 5 PHENYLPENT 2 ENOIC ACID (2 AMINOETHYL)AMIDE; 4 (3 BIPHENYL 4 YLUREIDO) 5 PHENYLPENT 2 ENOIC ACID (3 AMINOPROPYL)AMIDE; 4 [3 (4 PHENOXYPHENYL)UREIDO] 5 PHENYLPENT 2 ENOIC ACID (2 METHYLAMINOETHYL)AMIDE; 4 [3 (PHENOXYPHENYL 4 YLUREIDO)] 5 PHENYLPENT 2 ENOIC ACID (3 AMINOPROPYL)AMIDE; 4 [3 (PHENOXYPHENYL)UREIDO] 5 PHENYLPENT 2 ENOIC ACID (2 AMINOETHYL)AMIDE; 4 METHYL 3 [3 (4 PHENOXYPHENYL)UREIDO]PENTANOIC ACID (2 PYRROLIDIN 1 YLETHYL)AMIDE; 5 METHYL 3 [3 (4 PHENOXYPHENYL)UREIDO]HEXANOIC ACID (2 PYRROLIDIN 1 YLETHYL)AMIDE; AMINO ACID DERIVATIVE; AMINO ACID TRANSPORTER; BETA AMINO ACID; GAMMA AMINO ACID; GLYCINE; N (2 AMINOETHYL) 3 (3 BIPHENYL 4 YLUREIDO) 3 PHENYLPROPIONAMIDE; N (2 DIMETHYLAMINOETHYL) 3 [3 (4 PHENOXYPHENYL)UREIDO] 4 PHENYLBUTYRAMIDE; PROTEIN INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; AMINO ACID; DICYANDIAMIDO; GLYCINE TRANSPORTER; GUANIDINE DERIVATIVE; NEUROTRANSMITTER UPTAKE INHIBITOR;

AMINO ACID TRANSPORT; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; LIPOPHILICITY; ANIMAL; CELL STRAIN COS1; CERCOPITHECUS; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; GENETICS; METABOLISM; SYNTHESIS; TRANSPORT AT THE CELLULAR LEVEL;

AMINO ACID TRANSPORT SYSTEMS, NEUTRAL; AMINO ACIDS; ANIMALS; BIOLOGICAL TRANSPORT; CERCOPITHECUS AETHIOPS; COS CELLS; GLYCINE; GLYCINE PLASMA MEMBRANE TRANSPORT PROTEINS; GUANIDINES; NEUROTRANSMITTER UPTAKE INHIBITORS;

EID: 3242777772     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.05.043     Document Type: Article

References (24)

1. Krnjevic K. Physiol. Rev. 54:1974;418
2. Zafra F., Aragón C., Olivares L., Danbolt N.C., Giménez C., Storm-Mathisen J. J. Neurosci. 15:1995;3952
3. Luque J.M., Nelson N., Richards J.G. Neuroscience. 64:1995;525
4. Jursky F., Nelson N. J. Neurochem. 64:1995;1026
5. Friauf E., Aragón C., Lohrke S., Westenfelder B., Zafra F. J. Comp. Neurol. 412:1999;17
6. Aragón Carmen, López-Corcuera Beatriz Eur. J. Pharm. 479:2003;249
7. Simpson R.K., Gondo M., Robertson C.S., Goodman J.C. Neurochem. Res. 21:1996;1221
8. Huang W., Simpson R.K. Neurol. Res. 22:2000;160
9. Caulfield W.L., Collie I.T., Dickins R.S., Epemolu O., McGuire R., Hill D.R., McVey G., Morphy J.R., Rankovic Z., Sundaram H. J. Med. Chem. 44:2001;2679
10. Gomeza J., Ohno K., Betz H. Curr. Opin. Drug Discovery Dev. 6:2003;675
11. Examples of other GlyT-2 medicinal chemistry programs: Ho K.K., Appell K.C., Baldwin J.J., Bohnstedt A.C., Dong G., Guo T., Horlick R., Islam K.R., Kultgen S.G., Masterson C.M., McDonald E., McMillan K., Morphy J.R., Rankovic Z., Sundaram H., Webb M. Bioorg. Med. Chem. Lett. 14:2004;545
12. Isaac M., Abdelmalik S., Da Silva K., Arora J., MacLean N., Hung B., McCallum K. Bioorg. Med. Chem. Lett. 11:2001;1371
13. Caufield W.L., Collie I.T., Dickins R.S., Epemolu O., McGuire R., Hill D.R., McVey G., Morphy R., Rankovic Z., Sundaram H. J. Med. Chem. 44:2001;2679
14. Wolin, R. L.;Venkatesan, H.; Tang, L.; Santillán, A., Jr.; Barclay, T.; Wilson, S.; Lee, D. H.; Lovenberg, T. W. Part 1 of 2 for this series, Bioorg. Med. Chem. 2004, 12, see doi:10.1016/j.bmc.2004.05.042
15. The commercial availability of starting materials dictated, which route (A or B) was employed
16. Atwal K.S., Grover G.J., Ahmed S.Z., Sleph P.G., Dzwonczyk S., Baird A.J., Normandin D.E. J. Med. Chem. 38:1995;3236
17. Atwal K.S., Ahmed S.Z., O'Reilly B.C. Tetrahedron Lett. 30:1989;7313
18. Boden P.R., Eden J.M., Higginbottom M., Hill D.R., Horwell D.C., Hunter J.C., Martin K., Pritchard M.C., Richardson R.S., Roberts E. Eur. J. Med. Chem. 28:1993;47
19. The amines used were: N,N-dimethylethylenediamine, N,N- diethylethylenediamine, N-isopropylethylenediamine and 1-(2-aminoethyl) pyrrolidine
20. Basha A., Lipton M., Weinreb S.M. Tetrahedron Lett. 1977;4171
21. Still W.C., Gennari C. Tettrahedron Lett. 24:1983;4405
22. Ando K., Oishi T., Hirama M., Ohno H., Ibuka T. J. Org. Chem. 65:2000;4745
23. Masereel B., Wouters J., Pochet L., Lambert D. J. Med. Chem. 41:1998;3239
24. Lovenberg T.W., Roland B.L., Wilson S.J., Xiaoxia J., Pyati J., Huvar A., Jackson M.R., Erlander M.G. Mol. Pharm. 55:1999;1101