Patent ID: 6770759
Filing Date: 2004-08-03
Classification: A61P,C07D

Abstract:
A process for preparing a compound of formula (I): whereinR1 and R2 are each independently hydrogen, (C1-C10)alkyl, (C3-C8)cycloalkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, â€”COORa, â€”CONRbRc, cyano, â€”C(&boxH;O)Rd, â€”ORe, aryl, heteroaryl, oxazolidinyl, isoxazolidinyl, morpholinyl, â€”S(O)mRf, â€”NRgRh, azido, or halo; R3 is (C3-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkanoyl, (C3-C8)cycloalkyl, aryl, heteroaryl, aryl(C1-C10)alkyl, heteroaryl(C1-C10)alkyl, or â€”CH2Ri, wherein Ri is halo, cyano, cyanato, â€”ORj, â€”NRkRl, azido, â€”SRm, or (C3-C8)cycloalkyl; R4 is hydrogen; 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; Rj is hydrogen, (C1-C10)alkyl, (C3-C8)cycloalkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, â€”C(&boxH;O)N(Rp)2, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, or (C1-C10)alkanoyl, wherein each Rp is independently hydrogen, (C1-C10)alkyl, aryl, benzyl, phenethyl, or heteroaryl; each Rk or Rl is independently hydrogen, (C1-C10)alkyl, (C3-C8)cycloalkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkanoyl, â€”C(&boxH;O)N(R2)2, aryl, benzyl, phenethyl, heteroaryl oxazolidinyl, isoxazolidinyl, or morpholinyl, wherein each Rq is independently hydrogen, (C1-C10)alkyl, aryl, benzyl, phenethyl, or heteroaryl; or Rk and Rl together with the nitrogen to which they are attached are triazolyl, imidazolyl, oxazolidinyl, isoxazolidinyl, pyrrolyl, morpholino, piperidino, pyrrolidino, pyrazolyl, indolyl, or tetrazolyl; and Rm 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-Rm, or Rp-Rq, 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 â€”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; comprising: deprotecting a corresponding ester of the formula (I) where R4 is (C1-C10)alkyl, (C3-C8)cycloalkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, aryl, or heteroaryl, to form the compound of formula (I) wherein R4 is hydrogen.