Sequential synthesis of a new analogue of amlodipine bearing a short amino polyethyleneglycol chain

Tetrahedron

Volumn 63, Issue 48, 2007, Pages 12081-12086

  Legeay, Jean Christophe ^a   Vanden Eynde, Jean Jacques ^b   Bazureau, Jean Pierre ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b UNIVERSITY OF MONS   (Belgium)

Author keywords

1,4 Dihydropyridine; Analogue of amlodipine; Knoevenagel reaction; Staudinger reduction

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; 3 ETHYL 5 METHYL 2 [[2 [2 (2 AMINOETHOXY)ETHOXY]ETHOXY]METHYL] 4 (2 CHLOROPHENYL) 6 METHYL 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLATE; AMINO ACID DERIVATIVE; AMLODIPINE; DICARBOXYLIC ACID DERIVATIVE; MACROGOL; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; KNOEVENAGEL CONDENSATION; PRIORITY JOURNAL; STAUDINGER REACTION;

EID: 35348891028     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.08.111     Document Type: Article

References (35)

1. Janis R.A., Silver P.J., and Triggle D.J. Adv. Drug Res. 16 (1987) 309-314
2. Bossert F., and Vater W. Med. Res. Rev. 9 (1989) 291-324
3. Janis R.A., and Triggle D.J. J. Med. Chem. 26 (1983) 775-785
4. Loev B., Goodman M.M., Snader K.M., Tedeschi R., and Macko E. J. Med. Chem. 17 (1974) 956-965
5. Aouam K., and Berdeaux A. Thérapie 58 (2003) 333-339
6. Alker D., Campbell S.F., Cross P.E., Burgess R.A., Carter A.J., and Gardiner D.G. J. Med. Chem. 32 (1989) 2381-2388
7. Alker D., Burges R.A., Campbell S.F., Carter A.J., Cross P.E., Gordiner D.G., Humphrey M.J., and Stopher D.A. J. Chem. Soc., Perkin Trans. 2 (1992) 1137-1140
8. Arrowsmith J.E., Campbell S.F., Cross P.E., Burges R.A., and Gardiner D.G. J. Med. Chem. 32 (1989) 562-568
9. Arrowsmith J.E., Campbell S.F., Cross P.E., Stubbs J.K., Burges R.A., Gardiner D.G., and Blackburn R.A. J. Med. Chem. 26 (1986) 1696-1702
10. Liang J.C., Yeh J.L., Wang C.S., Liou S.F., Tsai C.H., and Chen I.J. Bioorg. Med. Chem. 10 (2002) 719-730
11. Caron G., Ermondi G., Damiano A., Navaroli L., Tsinman O.K., Ruell J.A., and Avdeef A. Bioorg. Med. Chem. 12 (2004) 6107-6118
12. Taniwa T., Miyataka M., Kimura A., Taniguchi M., Hirano Y., Hayashi T., and Ishikawa K. Circ. J. 69 (2005) 1308-1314
13. In: Zhu J., and Bienaymé H. (Eds). Multicomponent Reaction (2005), Wiley-VCH, Weinheim, Germany
14. Legeay J.C., Vanden Eynde J.J., and Bazureau J.P. Tetrahedron 61 (2005) 12386-12397
15. Campbell, S. F. U.S. Patent 4,572,909, 1986;
16. Alker, D.; Campbell, S. F.; Cross, P. E. U.S. Patent 4,892,881, 1990.
17. The 1,4-DHP nucleus was built by Diels-Alder reaction, see:. Kim S.C., Choi K.M., and Cheong C.S. Bull. Korean Chem. Soc. 23 (2002) 143-144
18. Dolle F., Valette H., Hinnen F., Demphel S., Bramoulle Y., Peglion J.L., and Crouzel C. J. Labelled Compd. Radiopharm. 44 (2001) 481-499
19. Dolle F., Hinnen F., Valette H., Fuseau C., Duval R., Peglion J.L., and Crouzel C. Bioorg. Med. Chem. 5 (1997) 749-764
20. Salgado A., Boeykens M., Gauthier C., Declercq J.P., and De Kimpe N. Tetrahedron 58 (2002) 2763-2775
21. Li J., Zacharek S., Chen X., Wang J., Zhang W., Janczuk A., and Wang P.G. Bioorg. Med. Chem. 7 (1999) 1549-1558
22. Hooper N., Beeching L.J., Dyke J.M., Morris A., Ogden J.S., Dias A.A., Costa M.L., Barros M.T., Cabral M.H., and Moutinho A.M.C. J. Phys. Chem. A 106 (2002) 9968-9975
23. Aslan, T.; Adiyaman, M.; Yurdakul, A.; Sahpaz, F.; Ozarslan, E.; Guner, D.; Ridvanoglu, N. Patent WO 2004/058711 A1, 2004.
24. Peters, T.; Benneker, F.; Slanina, P.; Bartl, J. Patent WO 02/053535 A2, 2002;
25. Peters, T.; Benneker, F.; Slanina, P.; Bartl, J. U.S. Patent 2002/0143046 A1, 2002.
26. Chun J., He L., Byun H.S., and Bittman R. J. Org. Chem. 65 (2000) 7634-7640
27. Maiti S.N., Singh M.P., and Micetich R.G. Tetrahedron Lett. 27 (1986) 1423-1424
28. Cheng H., Cao X., Xian M., Fang L., Cai T.G., Jia J.J., Tunac J.B., Sun D., and Wang P.G. J. Med. Chem. 48 (2005) 645-652
29. Staudinger H., and Meyer M.P. Helv. Chim. Acta 2 (1919) 635-646
30. For applications of Staudinger reaction in chemical biology, see the review:. Köhn M., and Breinbauer R. Angew. Chem., Int. Ed. 43 (2004) 3106-3116
31. Fresnada P.M., and Molina P. Synlett (2004) 1-17
32. Fukuta Y., Mita T., Fukuda N., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 128 (2006) 6312-6313
33. Oh C.H., Lee S.C., and Cho J.H. Eur. J. Med. Chem. 38 (2003) 841-850
34. The overall yield by Pfizer Company is 8.8%, see Ref. 7 and by Kim's group (via Diels-Alder reaction) is 8%, see Ref. 12.
35. H-3=8.05 ppm) for the E-isomer, see also Ref. 19a for comparison.