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US 8,889,163 B2Granted
Facially amphiphilic polymers as anti-infective agents
AssigneeThe Trustees of the University of Pennsylvania
InventorsWilliam F. DeGrado, Gregory N. Tew, Michael L. Klein
Life of this patent
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Abstract
Facially amphiphilic polyphenylene and heteroarylene polymers and articles made therform having biocidal surfaces are disclosed. The polymers can inhibit the growth of microorganisms in contact with the surface or in areas adjacent to said biocidal surface. There is also disclosed a methods to attach facially amphiphilic polmers to a solid support. Utility as a contact disinfectant is disclosed.
Claims27
A polymer or oligomer of formula I
- wherein:
- A and B are o- or m-phenylene wherein one of A or B is substituted with a polar (P) group and a nonpolar (NP) group and the other of A or B is substituted with neither a polar (P) group nor a nonpolar (NP) group;
- s is C≡C—;
- R1 is (i) halo and R2 is hydrogen;
- or (ii)C-s-B-s- and R2 is C;
- or, (iii)C-s- and R2 is -A-s-C wherein C is pyridine or phenyl said pyridine or phenyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halo, nitro, cyano, C1-C6alkoxy, C1-C6alkoxycarbonyl, and benzyloxycarbonyl;
- NP is a nonpolar group independently selected from R4 or —U—(CH2)p—R4 wherein R4 is selected from the group consisting of hydrogen, C1-C10 alkyl, C3-C18 branched alkyl, C3-C8cycloalkyl, monocyclic or polycyclic phenyl optionally substituted with one or more C1-C4 alkyl or halo groups, and monocyclic or polycyclic heteroaryl optionally substituted with one or more C1-C4 alkyl or halo groups, and U and p are as defined below;
- P is a polar group selected from the group consisting of III, hydroxyethoxymethyl, methoxyethoxymethyl and polyoxyethylene
- —U—(CH2)p—V (III)
- wherein:
- U is absent or selected from the group consisting of O, S, S(═O), S(═O)2, NH, —C(═O)O—, —C(═O)NH—, —C(═O)S—, —C(═S)NH—, —S(═O)2NH—, and C(═NO—) wherein groups with two chemically nonequivalent termini can adopt both possible orientations;
- V is selected from the group consisting of amino, hydroxyl, C1-C6alkylamino, C1-C6dialkylamino, NH(CH2)pNH2, N(CH2CH2NH2)2, amidine, guanidine, semicarbazone, basic heterocycle, and phenyl optionally substituted with an amino, C1-C6alkylamino, C1-C6dialkylamino and lower acylamino optionally substituted with one or more amino, lower alkylamino or lower dialkylamino;
- and the alkylene chain is optionally substituted with an amino or hydroxyl group or unsaturated;
- p is independently 0 to 8;
- and,
- m is 2 to about 500.
13 more elements
A polymer or oligomer of formula XIX
- wherein
- NP is methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, or sec-pentyl;
- P is a polar group U—(CH2)p—V wherein U is O or S, p is 0 to 8 and V is selected from the group consisting of amino, lower alkyl amino, lower dialkylamino, guanidine, pyridine, piperazine, and 4-alkylpiperazine;
- p is 0 to 8;
- and,
- m is 2 to about 30.
3 more elements
Dependencies are inferred from the claim text.