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US 7,125,986 B2Granted
Penicillanic acid derivative compounds and methods of making
AssigneeSouthern Methodist University Foundation for Research
InventorsJohn D. Buynak, Akireddy Srinivasa Rao, Venkata Ramana Doppalapudi
Life of this patent
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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 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.
Claims8
A compound of formula (I):
- wherein
- R1 and R2 are each independently hydrogen, (C1–C10)alkyl, (C3–C8)cycloalkyl, (C2–C10)alkenyl, (C2–C10)alkynyl, —COORa, —CONRbRc, cyano, —C(═O)Rd, —ORe, aryl, heteroaryl, oxazolidinyl, isoxazolidinyl, morpholinyl, —S(O)mRf, —NRgRh, azido, or halo;
- wherein R3 is acetoxymethyl, chloroacetoxymethyl, phenylacetoxymethyl, (3,4-dihydroxyphenyl)acetoxymethyl, or (1-methyl-1H-tetrazol-5-ylthio)acetoxymethyl;
- R4 is hydrogen (C1–C10)alkyl, (C3–C8)cycloalkyl, (C2–C10)alkenyl, (C2–C10)alkynyl, aryl, or heteroaryl;
- m and n are each independently 0, 1, or 2;
- each Ra–Rf is independently hydrogen, (C1–C10)alkyl, (C3–C8)cycloalkyl, (C2–C10)alkenyl, (C2–C10)alkynyl, aryl, heteroaryl, oxazolidinyl, isoxazolidinyl, or morpholinyl;
- each Rg or Rh is independently hydrogen, (C1–C10)alkyl, (C3–C8)cycloalkyl, (C2–C10)alkenyl, (C2–C10)alkynyl, (C1–C10)alkanoyl, aryl, benzyl, phenethyl, heteroaryl oxazolidinyl, isoxazolidinyl, or morpholinyl;
- or Rg and Rh together with the nitrogen to which they are attached are triazolyl, imidazolyl, oxazolidinyl, isoxazolidinyl, pyrrolyl, morpholino, piperidino, pyrrolidino, pyrazolyl, indolyl, or tetrazolyl;
- wherein any (C1–C10)alkyl, (C3–C8)cycloalkyl, (C2–C10)alkenyl, (C2–C10)alkynyl, (C1–C10)alkanoyl, benzyl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, oxazolidinyl, isoxazolidinyl, or morpholinyl of R1–R4, or Ra–Rh, 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, heteroaryl, or —SRn, wherein Rn is hydrogen, (C1–C10)alkyl, (C3–C8)cycloalkyl, aryl, benzyl, phenethyl, or heteroaryl;
- and further wherein any aryl, aryloxy, heteroaryl, benzyl, or phenethyl of Z may optionally be substituted with 1, 2, or 3 substituents selected from the group consisting of halo, nitro, cyano, hydroxy, (C1–C10)alkyl, (C3–C8)cycloalkyl, (C1–C10)alkoxy, (C1–C10)alkanoyl, (C2–C10)alkanoyloxy, benzyloxy, 4–methoxybenzyloxy, and trifluoromethyl;
- or a pharmaceutically acceptable salt thereof.
9 more elements
Dependencies are inferred from the claim text.