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US 2011/0257380 A1Published application
Glycomimetic replacements for hexoses and n-acetyl hexosamines
AssigneeGlycoMimetics, Inc.
InventorsBeat ERNST, Daniel SCHWIZER, Arun K. SARKAR, John L. MAGNANI
Life of this patent
Estimating the term…
Abstract
Compounds and methods are provided for obtaining oligosaccharide mimics. More specifically, compounds and methods are described wherein oligosaccharide mimics are obtained by incorporating or substituting in a cyclohexane derivative.
Claims12
-3. (canceled)
A compound comprising:
- R1═H, C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, halogenated C1-C8 alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, OH, or NHX where X═H, C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, halogenated C1-C8 alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH;
- C(═O)OX, alkanyl substituted with C(═O)OX, C(═O)NHX, alkanyl substituted with C(═O)NHX, where X═C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, halogenated C1-C8 alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH;
- NHX, where X═H, C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, halogenated C1-C8 alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH;
- R2═H, C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, halogenated C1-C8 alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, OH, or NHX where X═H, C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, halogenated C1-C8 alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH;
- —C(═O)OX where X is C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH;
- —C(═O)NH(CH2)nNH2 where n=0-30, C(═O)NHX or CX2OH, where X═C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, halogenated C1-C8 alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH;
- OX, NHX, NH(═O)X, where X═H, C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, halogenated C1-C8 alkanyl, aryl or heteroaryl either of which may be substituted with one or more of Me, OMe, halide, or OH;
- with the proviso that R1 and R2 are not both H;
- R3═—OH,
- —O—C(═O)—X, —NH2, —NH—C(═O)—NHX, or —NH—C(═O)—X where n=0-2 and X is independently selected from C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl,
- where Q is H or a physiologically acceptable cation, C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, aryl, heteroaryl, (CH2)m-aryl or (CH2)m-heteroaryl where m is 1-10, and where n=0-10, and any of the above ring compounds may be substituted with one to three independently selected of Cl, F, CF3, C1-C8 alkoxy, NO2, C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, C1-C14 aryl, or OY, C(═O)OY, NY2 or C(═O)NHY where Y is H, C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, or C1-C14 aryl;
- where R9 is aryl, heteroaryl, cyclohexane, t-butane, adamantane, or triazole, and any of R9 may be substituted with one to three independently selected of Cl, F CF3, C1-C8 alkoxy, NO2, C1-C8 alkanyl, C1-C8 alkenyl, C1-C8alkynyl or OY, C(═O)OY, NY2 or C(═O)NHY where Y is H, C1-C8 alkanyl, C1-C8 alkenyl, and C1-C8 alkynyl or C1-C14 aryl;
- and where R10 is one of
- where Q is H or a physiologically acceptable cation, C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, aryl, heteroaryl, (CH2)m-aryl or (CH2)m-heteroaryl where m is 1-10, n=1-4, Z and Y═C1-C8 alkanyl, C1-C8 alkenyl, C1-C8 alkynyl, halogenated C1-C8 alkanyl, aryl and heteroaryl substituted with Me, OMe, halide, OH;
- and
- R5═H, D-mannose, L-galactose, D-arabinose, L-fucose, polyols.
13 more elements
-17. (canceled)
Dependencies are inferred from the claim text.