C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 499/88 (2006.01) C07D 463/00 (2006.01) C07D 477/00 (2006.01) C07D 477/02 (2006.01) C07D 505/00 (2006.01) C07D 519/00 (2006.01) C07D 498/053 (1990.01)
Patent
CA 2120493
2120493 9307154 PCTABS00021 The present invention provides methods of making compounds of the structure [Q - L1] - L - [L2 - B], wherein Q is a quinolone moiety; B is a beta-lactam moiety; L, L1, and L2 together comprise a carbamate-containing linking moiety, comprising the steps of: 1) reacting a lactam compound of the formula B-L4-H with phosgene to form an intermediate compound of the formula B-L4-C(=O)-Cl, where L4 is oxygen; and 2) coupling said intermediate compound with a quinolone compound of the formula Q-l3-R44, wherein L3 is nitrogen; R44 is hydrogen, Si(R45)3, or Sn(R45)3; and R45 is lower alkyl. Preferably, the process additionally comprises steps prior to the reacting and coupling steps where esters of the lactam and quinolone compounds are made. Also preferably, the coupling step comprises adding a solution containing the quinolone compound to a solution containing the intermediate compound. The process steps are also preferably performed at a temperature of from about -80 ·C to about 0 ·C. Preferred antimicrobial compounds made by these processes are those where the beta-lactam moiety is a penem.
Demuth Thomas P. Jr.
White Ronald E.
Kirby Eades Gale Baker
Procter & Gamble Pharmaceuticals Inc.
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