Patent ID: 6355664
Filing Date: 2002-03-12
Classification: C07D,C07F

Abstract:
A compound of the formula I wherein:Y is an oxygen atom; Z is an oxygen atom; X is a divalent group of the formula >CHR1 or >NR1, wherein R1 is: (A) a hydrogen atom, (B) branched or unbranched alkyl of 1 to 6 carbon atoms or cycloalkyl of 3 to 6 carbon atoms, which alkyl or cycloakyl group is unsubstituted or monosubstituted with: (i) oxo, (ii) aryl selected from the class consisting of phenyl, thiophenyl, pyridyl, pyrimidinyl, furyl, pyrrolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, imidazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyridazinyl, pyrazinyl and triazinyl, â€ƒwherein one or more hydrogen atoms of said aryl group are or are not independently replaced with: â€ƒ(a) alkyl of 1 to 3 carbon atoms, â€ƒ(b) â€”COOH, â€ƒ(c) â€”SO2OH, â€ƒ(d) â€”PO(OH)2, â€ƒ(e) a group of the formula â€”COOR7, wherein R7 is straight or branched alkyl of 1 to 5 carbon atoms or cycloalkyl of 3 to 5 carbon atoms, â€ƒ(f) a group of the formula â€”NH2, â€ƒ(g) a group of the formula â€”CONH2, â€ƒ(h) a group of the formula â€”OR12a, wherein R12a is a hydrogen atom or a methyl, â€ƒ(i) an amidino group of the formula â€ƒwherein R13, R14 and R15 are each hydrogen atoms, (iii) a group of the formula â€”COOR16, wherein R16 is straight or branched alkyl of 1 to 7 carbon atoms or cycloalkyl of 3 to 6 carbon atoms, (iv) a group of the formula OR19, wherein R19 is a hydrogen atom, or an alkyl or acyl group of 1 to 7 carbon atoms, or (v) a quaternary group of the formula â€ƒwherein R24, R25 and R26 are each methyl and Qâˆ’ is a chlorine, bromine or iodine counterion, (C) a group of the formula â€”COOH connected via a branched or unbranched alkyl group of 2 to 5 carbon atoms, (D) a group of the formula â€”PO(OH)2 connected via a branched or unbranched alkyl group of 2 to 6 carbon atoms, (E) a group of the formula â€”SO2OH connected via a branched or unbranched alkyl group of 2 to 6 carbon atoms, (F) an amidino group of the formula â€ƒwherein r is 2, 3, 4, 5 or 6, and â€ƒR27, R28 and R29 are each hydrogen atoms, (G) an guanidino group of the formula â€ƒwherein s is 2, 3, 4, 5 or 6, â€ƒR30, R31, R32 and R33 are each hydrogen atoms, or (H) piperidyl, wherein the nitrogen atom of said group is unsubtituted or substituted with: (i) alkyl of 1 to 3 carbon atoms, (ii) a group of the formula â€”COO(C1-6alkyl), (iii) a group of the formula â€”COOH connected via an alkyl group of 1 to 4 carbon atoms, (iv) a group of the formula â€”PO(OH)2 connected via an alkyl group of 1 to 6 carbon atoms, or (v) a group of the formula â€”SO2OH connected via an alkyl group of 1 to 6 carbon atoms; R2 is: (A) a hydrogen atom, or (B) methyl; R3 is a group of the formula â€”CH2R41, wherein R41 is â€ƒaryl selected from the class consisting of phenyl, thiophenyl, pyridyl, pyrimidinyl, furyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, and pyrazinyl, â€ƒwherein one or more of the hydrogen atoms of said aryl group are necessarily and independently replaced with: (A) R62, which is aryl selected from the class consisting of phenyl, thiophenyl, pyridyl, pyrimidinyl, furyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, and pyrazinyl, â€ƒwherein one or more of the hydrogen atoms of said aryl group are or are not independently replaced with: (i) methyl, (ii) â€”COOH, (iii) a group of the formula â€”COOR63, wherein R63 is methyl, (iv) a group of the formula â€”OR68, wherein R68 is a hydrogen atom or methyl, or (v) halogen, (B) methyl, which is unsubstituted or mono- or polysubstituted with fluorine atoms or which is unsubstituted or monosubstituted with R62, (C) branched or unbranched alkyl of 2 to 6 carbon atoms or cycloalkyl of 3 to 6 carbon atoms, which alkyl or cycloakyl group is unsubstituted or mono- or polysubstituted with halogen or oxo, (D) a group of the formula â€”COOR73, wherein R73 is methyl, (E) a group of the formula â€”CONR76R77, wherein R76 and R77 are each methyl, and wherein one of R76 and R77 is methyl and the other is the group R62, (F) a group of the formula â€”COR78, wherein R78 is a hydrogen atom, methyl or R62, (G) a group of the formula â€”OR79, wherein R79 is a hydrogen atom, methyl or R62, (H) cyano, (I) nitro, or (J) halogen; R4 is Cl or trifluoromethyl; R5 is a hydrogen atom; and, R6 is Cl, or trifluoromethyl; or a pharmaceutically acceptable salt thereof.