Abstract
A straightforward synthesis of methyl 3,4-dihydro-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide from saccharin sodium salt was achieved
in five steps. Methyl 3,4-dihydro-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide found application as a precursor for
the synthesis of a new class of quaternary ammonium derivatives that are potential
antiosteoarthritis agents.
Key words
oxicams - quaternary ammonium - heterocycles - esters - enols
References
<A NAME="RT08405SS-1A">1a</A>
Lombardino JG.
Wiseman EH.
McLamore WM.
J. Med. Chem.
1971,
14:
1171
<A NAME="RT08405SS-1B">1b</A>
Lombardino JG. inventors; U.S. Pat. 3,591,584.
; Chem Abstr. 1970, 73, 120647
<A NAME="RT08405SS-1C">1c</A>
Lombardino JG.
Wiseman EH.
J. Med. Chem.
1972,
15:
848
<A NAME="RT08405SS-1D">1d</A>
Zinnes H.
Lindo NA.
Sircar JC.
Schwartz ML.
Shavel J.
J. Med. Chem.
1973,
16:
44
<A NAME="RT08405SS-1E">1e</A>
Lombardino JG.
Wiseman EH.
Med. Res. Rev.
1982,
2:
127
<A NAME="RT08405SS-2A">2a</A>
Nicolas C.
Verny M.
Giraud I.
Ollier M.
Rapp M.
Maurizis JC.
Madelmont JC.
J. Med. Chem.
1999,
42:
5235
<A NAME="RT08405SS-2B">2b</A>
Madelmont JC,
Giraud I,
Vidal A,
Mounetou E,
Rapp M,
Maurizis JC,
Renard P,
Caignard DH, and
Bizot-Espiard JG. inventors; International Patent PCT/FR01/04135.
<A NAME="RT08405SS-3">3</A>
Maurizis JC.
Ollier M.
Nicolas C.
Madelmont JC.
Guarrigue H.
Veyre A.
Biochem. Pharmacol.
1992,
44:
1927
<A NAME="RT08405SS-4">4</A>
Vidal, A.; Renard, P.; Madelmont, J. C.; Mounetou, E. J. Med. Chem. submitted.
<A NAME="RT08405SS-5">5</A>
Wells GJ.
Tao M.
Josef KA.
Bihovsky R.
J. Med. Chem.
2001,
44:
3488
<A NAME="RT08405SS-6">6</A>
Fernández-Tomé MP.
Madroñero R.
del Rio J.
Vega S.
J. Med. Chem.
1972,
15:
887
<A NAME="RT08405SS-7">7</A>
Weeks PD.
Vinick FJ.
Breitenbach R.
Jung S.
J. Org. Chem.
1983,
48:
3601
<A NAME="RT08405SS-8">8</A>
Zinner H.
Zelck U.
Rembarz G.
J. Prakt. Chem.
1959,
8:
150
<A NAME="RT08405SS-9">9</A>
Takata Y.
Yakagaku
1951,
71:
1474
<A NAME="RT08405SS-10">10</A>
Casadei MA.
Gessner A.
Inesi A.
Jugelt W.
Liebezeit H.
Micheletti Moracci F.
Bull. Soc. Chim. Fr.
1989,
650
<A NAME="RT08405SS-11">11</A>
Lombardino JG.
Wiseman EH.
Chiaini J.
J. Med. Chem.
1973,
16:
493