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US 7,022,691 B2Granted
Inhibitors of serine and metallo-β-lactamases
AssigneesJohn D. Buynak, Hansong Chen
InventorsJohn D. Buynak, Hansong Chen
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Abstract
Compounds of formula (I): wherein R1, R2, R3, R4 and n have any of the values defined in the specification, and their pharmaceutically acceptable salts, are useful for inhibiting simultaneously serine and metallo-β-lactamase enzymes, for enhancing the activity of β-lactam antibiotics, and for treating β-lactam resistant bacterial infections in a mammal. The invention also provides pharmaceutical compositions, processes for preparing compounds of formula I, and novel intermediates useful for the synthesis of compounds of formula I.
Claims4
A compound of formula (I):
- wherein
- R1 and R2 are H
- R3 is hydrogen, carboxy, (C1–C10)alkyl, (C2–C10)alkenyl, (C2–C10)alkynyl, (C1–C10)alkanoyl, (C3–C8)cycloalkyl, aryl, heteroaryl, alkyl arylakyl, alkoxycarbonyl, oxazolinyl, isoazolidinyl, morpholinyl, heteroarylcarbonyl, alkanoyloxy, or alkoxy;
- or —CH2Ra wherein Ra is halo, cyano, cyanato, —ORb, —NRcRd, azido, —SRe, O—CO—Rf, aryl, heteroaryl, (C3–C8)cycloalkyl, oxazolinyl, isoazolidinyl, morpholinyl, heteroarylcarbonyl, alkanoyloxy, or alkoxy;
- R4 is hydrogen, (C1–C10)alkyl, (C3–C8)cycloalkyl, (C2–C10)alkenyl, (C2–C10)alkynyl, alkoxycarbonyl, aryl, heteroaryl, arylalkyl, oxazolinyl, isoazolidinyl, morpholinyl, heteroarylcarbonyl, or alkoxy;
- n is 0, 1, or 2;
- Rb is hydrogen, (C1–C10)alkyl, (C3–C8)cycloalkyl, (C2–C10)alkenyl, (C2–C10)alkynyl, —C(═O)N(Rf)2, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, or (C1–C10)alkanoyl, wherein each Rf is independently hydrogen, (C1–C10)alkyl, aryl, benzyl, phenethyl, or heteroaryl;
- each Rc or Rd is independently hydrogen, (C1–C10)alkyl, (C3–C8)cycloalkyl, (C2–C10)alkenyl, (C2–C10)alkynyl, (C1–C10)alkanoyl, —C(═O)N(Rf)2, aryl, benzyl, phenethyl, heteroaryl, oxazolidinyl, isoxazolidinyl, or morpholinyl, wherein each Rf is independently hydrogen, (C1–C10)alkyl, aryl, benzyl, phenethyl, or heteroaryl;
- or Rc and Rd together with the nitrogen to which they are attached are triazolyl, imidazolyl, oxazolidinyl, isoxazolidinyl, pyrrolyl, morpholino, piperidino, pyrrolidino, pyrazolyl, indolyl, or tetrazolyl;
- and
- Re is hydrogen, (C1–C10)alkyl, (C3–C8)cycloalkyl, (C2–C10)alkenyl, (C2–C10)alkynyl, cyano, aryl, benzyl, phenethyl, heteroaryl, oxazolidinyl, isoxazolidinyl, or morpholinyl;
- wherein any (C1–C10)alkyl, (C3–C8)cycloalkyl, (C2–C10)alkenyl, (C2–C10)alkynyl, (C1–C10)alkanoyl, aryl, benzyl, phenethyl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, oxazolidinyl, isoxazolidinyl, or morpholinyl of R1–R4, Ra–Re, or Rf–Rg, may optionally be substituted with 1, 2, or 3 Z;
- and each Z is independently halo, nitro, cyano, hydroxy, (C1–C10)alkyl, (C3–C8)cycloalkyl, (C1–C10)alkoxy, (C1–C10)alkanoyl, (C2–C10)alkanoyloxy, trifluoromethyl, aryl, aryloxy, or heteroaryl;
- or a pharmaceutically acceptable salt thereof.
11 more elements
Dependencies are inferred from the claim text.