Ciba-geigy Corporation

Karl Schaffner

Riccardo Scartazzini

Beat Muller

Claus D Weis

Hansuli Wehrli

Alex Meisels

Jean Claude Roger

6-Amino-penam compounds, having an antimicrobial action, of the formula ##STR1## in which R.sub.1 is an azaoligocycloalkyl radical which is bonded via the ring nitrogen atom and contains at least one endo-bridge atom and a total of 7 to 12 ring atoms and can contain a double bond and/or, if desired, as a further ring hetero-atom, an oxygen atom, or a nitrogen atom which can link the radical X.sub.1, where X.sub.1 is hydrogen or lower alkyl, and/or, if desired, free, esterified or etherified hydroxyl which is bonded to a ring carbon atom, and in which R.sub.2 is free carboxyl or carboxyl esterified by a physiologically detachable group, and salts of such compounds, processes for their preparation, pharmaceutical preparations which contain these compounds, including mixtures of these compounds with other antimicrobial, especially antibacterial and/or antiviral, active ingredients and/or additional substances or substance mixtures which alleviate the symptoms in the case of infections, the use of the novel compounds of the formula I and their salts, and of the novel substance mixtures, for combating micro-organisms and the preparation of corresponding medicaments by non-chemical means.

6-Azaoligocycloalkylmethyleneaminopenam compounds

When 3-(2-hydroxyiminoacetylamino)-2-oxo-azetidine compounds are treated with reactive derivatives of carbonic acid half-esters in aqueous media in the presence of bases a fragmentation takes place which, in addition to 3-amino-2-oxo-azetidines, also yields nitriles which, compared with the 2-hydroxyiminoacetyl group, have one less carbon atom. The resulting products are intermediates for the preparation of nocardicin-like antibiotics. The deacylation procedure of this specification offers advantages over the multi-stage deacylation procedure known hitherto, inasmuch as higher yields of 3-amino-2-oxoazetidine compounds are obtained and the acyl group can be obtained in the form of a nitrile which is shorter by one carbon atom.

Fragmentation procedure for preparing 3-amino-azetidinones

Compounds of the class of spiro[norbornane-2,3'-piperidines], spiro[bicyclo[2.2.2]octane-2,3'-piperidines], and corresponding spiro-pyrrolidine derivatives which are unsubstituted at the ring nitrogen atom or substituted by neutral or basic radicals, and the pharmaceutically acceptable acid addition salts of these new compounds possess valuable pharmacological properties and are active ingredients for pharmaceutical compositions. In particular, these new compounds have an antiviral activity. Specific embodiments are (1RS,2RS,4SR)-spiro[norbornane-2,3'-piperidine]-hydrochloride and 1'-[2-(2-azaspiro[5.5]undec-2-yl)-ethyl]-spiro[bicyclo[2.2.2]octane-2,3'-p iperidine]-dihydrochloride.

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Oberwil, Switzerland

Karl Schaffner