Derivatives of 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines, proc

Details Derivatives of 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines, proc Derivatives of 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines, proc

1997-02-06

1998-12-01

Berch, Mark L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

540354, 540360, 540361, A61K 31395, C07D20508

Patent

active

058439390

ABSTRACT:
3-Bromo- and 3,3-dibromo-4-oxo-1-azetidines of the formula I ##STR1## wherein R.sub.1 is hydrogen or bromo,
R.sub.2 is hydrogen or bromo,
R.sub.3 is hydrogen, ##STR2## wherein R.sub.4 is hydrogen, methyl, benzyl or some other protective group,
R.sub.5 is hydrogen, alkyl, alkylaryl, a heterocyclic ring,
Y is a halo atom,
X is a halo atom, alkoxy group, nitroxy group are provided along with processes for the preparation thereof and the use thereof. The 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines can be prepared by reacting 2-sulfinic acid derivatives, with various halogenating agents, and after treating the reaction mixture, 2-halo derivatives of 3-bromo- and 2,2-dibromo-4-oxo-azetidines are isolated and are subjected to a reaction with silver tetrafluoroborate and alcohols to give the corresponding 2-alkoxy derivatives of 3-bromo- and 3,3-dibromo-4-oxo azetidines, or 2-halo derivatives of 3-bromo- and 3-3-dibromo-4-oxo azetidines are subjected to a reaction with silver nitrate in 2-propanol to give, after treating the reaction mixture, 2-nitroxy derivatives of 3-bromo and 3,3-dibromo-4-oxo-1-azetidines. Some newly prepared compounds are deprotected and derivatives having a free carboxy group are obtained. The prepared compounds are components in pharmaceutical compositions effective in antibacterial or antirumour therapy.

REFERENCES:
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patent: 4427586 (1984-01-01), Numata
patent: 4595539 (1986-06-01), Hamanaka
Martel, Can J Chem 61, 1899 1983.
Sanoza, Zetraheehan 44, 7007 (1988).
Lattrella, Chem, Abs 74, 12982n (1974).

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