An acid-catalyzed O,N-acyl migration and application to the synthesis of N-(4-isopropyl-2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6- carbonyl) guanidine methanesulfonate (KB-R9032), a novel Na/H exchange inhibitor

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 1, 1999, Pages 22-27

  Yamamoto, Takeshi ^a   Hori, Manabu ^a   Watanabe, Ikuo ^a   Tsutsui, Hisayoshi ^a   Ikeda, Shoji ^a   Ohtaka, Hiroshi ^a  

^a KANEBO LTD   (Japan)

Author keywords

KB R9032; Na H exchange inhibitor; O,N acyl migration; Practical synthesis; Rearrangement

Indexed keywords

1 (3,4 DIHYDRO 4 ISOPROPYL 2,2 DIMETHYL 3 OXO 2H 1,4 BENZOXAZINE 6 CARBONYL)GUANIDINE; MESYLIC ACID DERIVATIVE; PROTON; SODIUM ION; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; ISCHEMIA; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON SODIUM EXCHANGE; REPERFUSION INJURY;

EID: 0032995562     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.22     Document Type: Article

References (6)

1. a) Harada K., Sugimoto H., Shimamoto A., Watano T., Nishimura N., Jpn. J. Pharmacol., 73, Suppl. I, 232P (1997);
2. b) Yamamoto T., Hori M., Watanabe I., Tsutsui H., Harada K., Ikeda S., Maruo J., Morita T., Ohtaka H., Chem. Pharm. Bull., 46, 1716-1723 (1998).
3. Yamamoto T., Hori M., Watanabe I., Tsutsui H., Ikeda S., Ohtaka H., Chem. Pharm. Bull., 46, 1317-1320 (1998).
4. Weisburger E. K., Weisburger J. H., J. Org. Chem., 19, 964-972 (1954).
5. Welsh L. H., J. Am. Chem. Soc., 69, 128-135 (1947).
6. Sakurai T., Nagaoka T., Kamiya J., Inoue H., Bull. Chem. Soc. Jpn., 69, 775-778 (1996).