A convenient synthetic method of a 5,7-diarylcyclopenteno-[1,2-b]pyridine-6-carboxylate: A key intermediate for potent endothelin receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 10, Issue 11, 2002, Pages 3437-3444

  Niiyama, Kenji ^a   Yoshizumi, Takashi ^a   Takahashi, Hirobumi ^a   Naya, Akira ^a   Ohtake, Norikazu ^a   Fukami, Takehiro ^a   Mase, Toshiaki ^a   Hayama, Takashi ^a   Ishikawa, Kiyofumi ^a  

^a BANYU PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 BENZYLOXY 4 METHOXYBENZOYL) 3 (1 IMIDAZOLYL)CARBONYLPYRIDINE; 2 (2 BENZYLOXY 4 METHOXYBENZOYL) 3 PYRIDINECARBOXYLIC ACID; 6 TERT BUTOXYCARBONYL 7 (2 HYDROXY 4 METHOXYPHENYL) 5 (3,4 METHYLENEDIOXYPHENYL)CYCLOPENTENO[1,2 B]PYRIDINE; 7 (2 BENZYLOXY 4 METHOXYPHENYL) 6 TERT BUTOXYCARBONYL 5 (3,4 METHYLENEDIOXYPHENYL) 5 HYDROXYCYCLOPENTA 1,3 DIENO[2,1 B]PYRIDINE; 7 (2 BENZYLOXY 4 METHOXYPHENYL) 6 TERT BUTOXYCARBONYL 5 OXOCYCLOPENTA 1,3 DIENO[2,1 B]PYRIDINE; ACID; ACID ANHYDRIDE; ALLYL ALCOHOL; CARBOXYLIC ACID DERIVATIVE; ENDOTHELIN RECEPTOR ANTAGONIST; ESTER DERIVATIVE; IMIDAZOLE DERIVATIVE; PYRIDINE DERIVATIVE; REAGENT; SILICA GEL; UNCLASSIFIED DRUG; ZINC; ZINC DERIVATIVE;

ACIDITY; ARTICLE; CHROMATOGRAPHY; DEHYDRATION; METHODOLOGY; PURIFICATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

CARBOXYLIC ACIDS; CATALYSIS; INDICATORS AND REAGENTS; KETO ACIDS; PYRIDINES; RECEPTORS, ENDOTHELIN; SOLVENTS; STEREOISOMERISM; ZINC;

EID: 0036836945     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00261-4     Document Type: Article

References (11)

1. Yanagisawa M., Kurihara H., Kimura S., Tomobe Y., Kobayashi M., Mitsui Y., Yazaki Y., Goto K., Masaki T. Nature. 332:1988;411.
2. Ishikawa K., Fukami T., Nagase T., Fujita K., Hayama T., Niiyama K., Mase T., Ihara M., Yano M. J. Med. Chem. 35:1992;2139.
3. Elliot J.D., Lago M.A., Cousins R.D., Gao A., Leber J.D., Erhard K.F., Nambi P., Elshourbagy N.A., Kumar C., Lee J.A., Bean J.W., DeBrosse C.W., Eggleston D.S., Brooks D.P., Feuerstein G., Ruffolo R.R. Jr., Weinstock J., Gleason J.G., Peishoff C.E., Ohlstein E. J. Med. Chem. 37:1994;1553.
4. Niiyama, K.; Hayama, T.; Nagase, T.; Fukami, T.; Nishikibe, M.; Ihara, M.; Hisaka, A.; Mase, T.; Ishikawa, K.; Yano, M. Abstracts of Papers, 216th National Meeting of the American Chemical Society, Boston, Aug 23-27, 1998; MEDI 56.
5. Niiyama K.; Mase T.; Takahashi H.; Naya A.; Katsuki K.; Nagase T.; Ito S.; Hayama T.; Hisaka A.; Ozaki S.; Ihara M.; Yano M.; Fukuroda T.; Noguchi K.; Nishikibe M.; Ishikawa K.; Bioorg. Med. Chem., 2002, 10, 2461.
6. Potts K.T. Bhattacharjee D. Walsh E.B. J. Org. Chem. 1986 51 2011.
7. (a) Potts K.T., Bhattacharjee D., Walsh E.B. J. Org. Chem. 51:1986;2011 (b) Canonne P., Belley M. Can. J. Chem. 65:1987;1885.
8. In order to identify each structure of the product 7 and 8, they were converted to the corresponding methyl ester 9 and 10 and separated by column chromatography on silica gel to determine the ratio of the isomers via the reaction.
9. Cousins, R. D.; Elliott, J. D.; Lago, M. A.; Leber, J. D.; Peishoff, C. E. PCT Patent. WO 9308799, 1993; Chem. Abstr. 1992, 120, 106563.
10. Brooks D.W., Lu L.D.-L., Masamune S. Angew. Chem., Int. Ed. Engl. 18:1979;72.
11. Elphimoff-Felkin M.I., Sarda P. Tetrahedron Lett. 13:1972;725.