Synthesis and Purification of 6-Ethoxy-4-oxo-1,4-dihydro-[1,5] naphthyridine-3-carboxylic Acid Benzylamide

Organic Process Research and Development

Volumn 7, Issue 6, 2003, Pages 873-878

  Beaudin, Justin ^a   Meltz, Clifford N ^a   Meltz, Morgan ^a   Phillips, James E ^a   Ragan, John A ^a   Brown Ripin, David H ^a   Singer, Robert A ^a   Tucker, John L ^a   Wei, Lulin ^a   Bourassa, Dennis E ^a   Bowles, Paul ^a   Castaldi, Michael J ^a   Clay, Ronald ^a   Couturier, Michel A ^a   Karrick, Gregory ^a   Makowski, Teresa W ^a   McDermott, Ruth E ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID A RECEPTOR STIMULATING AGENT; 6 ETHOXY 4 OXO 1,4 DIHYDRO[1,5]NAPHTHYRIDINE 3 CARBOXYLIC ACID BENZYLAMIDE; QUINOLONE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG ISOLATION; DRUG PURITY; DRUG SOLUBILITY; DRUG SYNTHESIS; HIGH TEMPERATURE PROCEDURES;

EID: 0346104834     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0341061     Document Type: Article

References (14)

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5. Hiroshi, T.; Toshio, A. Japanese Patent 59093080A2, 1984.
6. Couturier, M.; Tucker, J. L.; Andresen, B. M.; Dubé, P.; Breneck, S. J.; Negri, J. T. Tetrahedron Lett. 2001, 42, 2285.
7. Gassman, P. G.; Schenk, W. N. J. Org. Chem. 1977, 42, 918-920.
8. All materials going into the final drug substance crystallization are filtered in solution or neat through a 1 micron filter prior to crystallization per an internal operating procedure.
9. The isolated yield of the potassium salt was 77% in a campaign where the solid salt was dried.
10. Toluene-denatured ethanol.
11. 2 and analyzing by HPLC.
12. All transfer equipment must be preheated to ensure that the potassium salt remains in solution during the sparkle step.
13. This filtration took under 1 h including the wash, which was necessary to reduce ash levels.
14. den Hertog, J. Recl. Trav. Chim. Pays-Bas 1953, 72, 125-131.