Boronic ester and acid compounds, synthesis and uses

A method for inhibiting HIV replication in an animal in need of said inhibiting, comprising administering to said animal an effective amount of a proteasome inhibitor of formula (1b)

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• or a pharmaceutically acceptable salt thereof;
• wherein
• P10 is selected from the group consisting of R7—C(O)—, R7—SO2—, R7—NH—C(O)—, and R7—O—C(O)—, where R7 is selected from the group consisting of alkyl, cycloalkyl, aryl, and aralkyl;
• B11 is independently one of N or CH;
• X11, at each occurrence, is independently one of —C(O)—NH—, —CH2—NH—, —CH(OH)—CH2, —CH(OH)—CH(OH)—, —CH(OH)—H2—NH—, —CH═CH—, —C(O)—CH2—, —SO2—NH—, —SO2—CH2— or —CH(OH)—CH2—C(O)—NH—, provided that when B11 is N, then X11 is —C(O)—NH—;
• X12 is one of —C(O)—NH—, —CH(OH)—CH2, —CH(OH)—CH(OH)—, —C(O)—CH2—, —SO2—NH—, —SO2—CH2— or —CH(OH)—CH2—C(O)—NH—;
• R10 is hydrogen or alkyl, or R10 forms together with the adjacent R11, or when A10 is zero, forms together with the adjacent R12, a nitrogen-containing mono-, bi- or tri-cyclic, saturated or partially saturated ring system having 4-14 ring members, that can be optionally substituted by one or two of keto, hydroxy, alkyl, aryl, aralkyl, alkoxy or aryloxy;
• R11, at each occurrence, is independently one of hydrogen, alkyl, cycloalkyl, aryl, a 5-10 membered saturated, partially unsaturated or aromatic heterocycle or —CH2—R15, where the ring portion of said aryl or heterocycle can be optionally substituted;
• R12 and R13 are each independently one of hydrogen, alkyl, cycloalkyl, aryl, a 5-10 membered saturated, partially unsaturated or aromatic heterocycle or —CH2—R15, where the ring portion of said aryl or heterocycle can be optionally substituted;
• R15 is phenyl, aralkyl, cycloalkyl, or -chalcogen-alkyl, where the ring portion of said phenyl or aralkyl can be optionally substituted;
• Z11 and Z12 are independently alkyl, hydroxy, alkoxy, or aryloxy, or together Z11 and Z12 form a moiety derived from a dihydroxy compound having at least two hydroxy groups separated by at least two connecting atoms in a chain or ring, said chain or ring comprising carbon atoms and, optionally, a heteroatom or heteroatoms which can be N, S, or O;
• and
• A10 is 0, 1, or 2.