Synthetic receptor analogues

Details Synthetic receptor analogues Synthetic receptor analogues

C - Chemistry, Metallurgy

07

H

167/125, 150/16,

C07H 15/00 (2006.01) A61K 31/70 (2006.01) C07H 15/04 (2006.01) C07H 15/14 (2006.01) C07H 23/00 (2006.01) G01N 33/569 (2006.01)

Patent

CA 1332234

ABSTRACT Compounds of the general formula I Image I wherein R1 is C1-24 alkyl; C2-24 alkenyl; C2-24 alkynyl; tri(C1-4 al- kyl)silylethyl; aryl optionally substituted with hydroxy, amino, C1-4 alkyl, C1-4 alkoxy, nitro, halogen, or phenoxy; mono- or di-halogen-C1-4alkyl; phenyl-C1-4alkyl; a group of the formula II or IIa R3-(CH2)n-S(O)m-CH2CH2- II R3-(CH2)n-S(O)m-CH2)2CH-CH2- IIa wherein R3 is H, carboxy, carboxy-C1-4 alkyl, hydroxy, amino, or a carrier, n is an integer from 1 to 24, and m is 0 or 2; a group of the formula III or IIIa Phe-S(O)m-CH2CH2- III (Phe-S(O)m-CH2)2CH-CH2- IIIa wherein m is as defined above, and each Phe is a phenyl group optionally monosubstituted with hydroxy, amino, C1-4 alkyl, C1-4 alkoxy, nitro, halogen, or phenoxy a group of the formula IV R4CH2CH(CH2R5)CH2- IV wherein R4 and R5 independently are halogen; a group Q-(CH2)n- where Q is a carrier, and n is as defined above; and R2 is a mono- or disaccharide moiety connected via a glycosidic bond; C1-18 alkyl; C2-18 alkenyl; C2-18 alkynyl; C1-18 alkyloxy- methyl; C1-18 alkanoyl; .alpha.-hydroxy-C1-18 alkanoyl; naphthyl-, heterocyclyl- or phenyl-C1-8 alkoxy where the naphthyl, hetero- cyclyl or phenyl group may be substituted with hydroxy, amino, C1-4 alkyl, C1-4 alkoxy, nitro, halogen, or phenoxy; tri(C1-4- alkyl)silylethyl; tri(C1-4-alkyl)silyl; tri(C1-4-alkyl)silylet- hoxymethyl; halogen; .omega.-hydroxy-C1-4alkyl; tetrahydropyranyl; benzyloxymethyl; C3-8 cycloalkyl; a monoterpenyl moiety; benzoyl optionally monosubstituted with hydroxy, amino, C1-4 alkyl, C1-4 alkoxy, nitro, halogen, or phenoxy; the acyl residue of a na- turally occurring amino acid; or a group of the formula V R6-C(O)-N(R7)-CH(R8)-CH2- V wherein R6 is C1-4 alkyl; or phenyl optionally monosubsti- tuted with hydroxy, amino, C1-4 alkyl, C1-4 alkoxy, nitro, halogen, or phenoxy, R7 is H or C1-4 alkyl, and R8 is H, C1-4 alkyl, or hydroxy-C1-4 alkyl, Z is -O-, -S-, -SO2-, or -CH2-, X is -O-, -S-, -SO2-, -CH2-, or -NR3-, wherein R3 is H or is one of the meanings for R2 above, R3 and R1 optionally being connec- ted to form a ring, and Y is -O- or -NR3- where R3 is H or is one of the meanings for R2 above, R3 and R2 optionally being connected to form a ring, as well as diagnostic devices or kits comprising at least one of such compounds in substantially immobilized form, and pharmaceu- tical compositions comprising at least one of the compounds in combination with a pharmaceutically acceptable inert carrier. Compounds of the general formula I have enhanced receptor binding properties to bacteria and are useful in inhibiting the binding of bacteria to mammalian cell surfaces.

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