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Details for Patent: 5,606,078

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Details for Patent: 5,606,078

Title: 3,5-Disubstituted tetrahydrofuran-2-ones
Abstract:Compounds of formula I ##STR1## wherein R.sub.1 is free or esterified carboxy, hydroxymethyl or formyl, R.sub.2 and R.sub.4 are each independently of the other aliphatic, cycloaliphatic-aliphatic, araliphatic or heteroarylaliphatic radicals and R.sub.3 is azido, or amino that is aliphatically or araliphatically substituted and/or protected by an amino-protecting group, and the salts thereof, are valuable intermediates in the preparation of medicinal active ingredients, for example of compounds of formula II ##STR2## wherein R.sub.A is an aromatic or heteroaromatic radical, R.sub.2 and R.sub.4 are each independently of the other aliphatic, cycloaliphatic, cycloaliphaticaliphatic or araliphatic radicals, R.sub.3 is unsubstituted or N-mono- or N,N-di-lower alkylated or N-lower alkanoylated amino, and R.sub.B is an aliphatically, cycloaliphatically or heteroaromatically-aliphatically substituted amino group, and the salts thereof, which can be used, for example, as antihypertensives.
Inventor(s): G oschke; Richard (Bottmingen, CH), Herold; Peter (Arlesheim, CH), Rigollier; Pascal (Sierentz, FR), Maibaum; J urgen K. (Weil-Haltingen, DE)
Assignee: Ciba-Geigy Corporation (Tarrytown, NY)
Filing Date:Apr 04, 1995
Application Number:08/416,237
Claims:1. A compound of formula I ##STR18## wherein R.sub.1 is free or esterified carboxy, hydroxymethyl or formyl,

R.sub.2 and R.sub.4 are each independently of the other aliphatic, cycloaliphatic-aliphatic, araliphatic or heteroarylaliphatic radicals, and

R.sub.3 is azido, or amino that is aliphatically or araliphatically substituted and/or protected by an amino-protecting group,

or a salt thereof.

2. A compound according to claim 1 of formula I wherein

R.sub.1 is carboxy, lower alkoxycarbonyl, unsubstituted or lower alkyl-, lower alkoxy-, halo-and/or trifluoromethyl-substituted phenyl-lower alkoxycarbonyl, hydroxymethyl or formyl,

R.sub.2 and R.sub.4 are each independently of the other lower alkyl radicals, lower alkenyl, lower alkoxy or lower alkylthio, 3- to 7-membered cycloalkyl-lower alkyl radicals, unsubstituted or lower alkyl-, lower alkoxy-, hydroxy-, halo-, nitro- and/or amino-substituted phenyl-lower alkyl or naphthyl-lower alkyl radicals or unsubstituted or lower alkyl-, lower alkoxy-, hydroxy-, halo-, nitro- and/or amino-substituted pyridyl-lower alkyl, indolyl-lower alkyl, quinolinyl-lower alkyl, pyrimidinyl-lower alkyl, furyl-lower alkyl, benzofuranyl-lower alkyl or thienyl-lower alkyl, and

R.sub.3 is azido, lower alkylamino, di-lower alkylamino, lower alkanoylamino or N-lower alkanoyl-N-lower alkyl-amino, unsubstituted or lower alkyl-, lower alkoxy-, hydroxy-, halo-, nitro-and/or amino-substituted phenyl-lower alkylamino, N-lower alkyl-N-phenyl-lower alkyl-amino or N-lower alkanoyl-N-phenyl-lower alkyl-amino or N-lower alkoxycarbonylamino, N-lower alkyl-N-lower alkoxycarbonyl-amino, N-lower alkanoyl-N-lower alkoxycarbonyl-amino, N-lower alkoxycarbonyl-N-phenyl-lower alkylamino, N-phenyl-lower alkoxycarbonylamino, N-lower alkyl-N-phenyl-lower alkoxycarbonyl-amino, N-lower alkanoyl-N-phenyl-lower alkoxycarbonyl-amino, N-phenyl-lower alkoxycarbonyl-N-phenyl-lower alkylamino, N-tri-lower alkylsilylamino, N-lower alkyl-N-tri-lower alkylsilyl-amino, N-lower alkanoyl-N-tri-lower alkylsilyl-amino or N-tri-lower alkylsilyl-N-phenyl-lower alkylamino,

or a salt thereof.

3. A compound according to claim 1 of formula I wherein

R.sub.1 is carboxy,

R.sub.2 is C.sub.1 -C.sub.4 alkyl,

R.sub.4 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, or phenyl-C.sub.1 -C.sub.4 alkyl that is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, by C.sub.1 -C.sub.4 alkoxy, by hydroxy, by halogen having an atomic number of up to and including 35, by nitro and/or by amino, and

R.sub.3 is azido, C.sub.1 -C.sub.4 alkoxycarbonylamino or phenyl-C.sub.1 -C.sub.4 alkoxycarbonylamino,

or a salt thereof.

4. A compound according to claim 1 being 2(S)-[2(S)-Azido-2(S)-(4(S)-isopropyl-5-oxo- tetrahydrofuran-2(S)-yl)-ethyl]-3-methyl-butyric acid or a salt thereof.

5. A compound according to claim 1 being 2-{2(S)-Azido-2-[4(S)-isopropyl-5-oxo- tetrahydrofuran-2(S)-yl]-ethyl}-3(S)-methyl-butyraldehyde or a salt thereof.

6. A compound according to claim 1 being 2-{2(S)-Azido-2-[4(S)-isopropyl-5-oxo-tetrahydrofuran -2(S)-yl]-ethyl}-3(S)-methyl-butanol or a salt thereof.

7. A compound according to claim 1 being 3(S)-Isopropyl-5(S)-(1(S)-(tert- butoxycarbonyl)amino)-3(S)-isopropyl-4-hydroxy-butyl)-tetrahydrofuran-2-on e or a salt thereof.
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