Back to results
US 2003/0166668 A1Published application
Substituted heteroarylalkanoic acids
AssigneeThe Institutes for Pharmaceutical Discovery, Inc. A Corporation of the State of Delaware
InventorsMichael C. Van Zandt, Leo Geraci
Life of this patent
Estimating the term…
Abstract
Disclosed are substituted heteroarylalkanoic acids acids of the following formula D-A-C(O)R′, where D, A, and R′ are defined herein. These compounds are useful in the treatment of chronic complications arising from diabetes mellitus. Also disclosed are pharmaceutical compositions containing the compounds and methods of treatment employing the compounds, as well as methods for their synthesis.
Claims78
A compound of the formula
- D-A-C(O)R′
- or a pharmaceutically acceptable salt thereof wherein
- D is a heteroaryl group selected from the group consisting of
- 145 146 147
- where
- Y is -Z-Ar where
- Z is a bond, O, S, C(O)NH, or C1-C6 alkylene optionally substituted with C1-C2 alkyl;
- and
- Ar represents
- an aryl or aryl(C1-C6)alkyl group, where the aryl portion is optionally substituted with up to 5 groups independently selected from
- (1) halogen, (C1-C6)alkyl, hydroxy, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 wherein each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy;
- and
- (2) phenyl, pyridyl, furyl, and thienyl, each of which is optionally substituted with one, two, or three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR17, SR17, S(O)R17, S(O)2R17 and N(R17)2 wherein each R17 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy;
- a heteroaryl or heteroaryl(C1-C6)alkyl group, where the heteroaryl portion is optionally substituted by one, two or three groups independently selected from
- (1) halogen, (C1-C6)alkyl, hydroxy, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6) alkanoyl, (C1-C6) alkylthio, (C1-C6)haloalkylthio, OR27, SR27, S(O)R27, S(O)2R27 and N(R27)2 wherein each R27 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy;
- and
- (2) phenyl, pyridyl, furyl, and thienyl, each of which is optionally substituted with one, two, or three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR37, SR37, S (O)R37, S(O)2R37 and N(R37)2 wherein each R37 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy;
- R3 is hydrogen, halogen, hydroxy, (C1-C6)alkyl, (C1-C6)haloalkyl, amino, (C1-C6)alkylamino, di(C1-C6)alkylamino, aryl, —SR15 or —OR1s, where R15 is (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl where each aryl is optionally mono-, di-, or trisubstituted with halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O) R7, S(O)2R7 and N (R7)2,
- R4 is hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkanoyl, or benzoyl where the phenyl portion is optionally mono-, di-, or trisubstituted with halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N (R7)2;
- R5 is hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, or aryl where aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2;
- R6 is hydrogen, (C1-C6)alkyl, oxo, (C3-C7)cycloalkyl, (C3-C7)cycloalkyl (C1-C6)alkyl or aryl (C1-C6)alkyl where the aryl portion is optionally mono-, di-, or trisubstituted with halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2;
- A is a C1-C4 alkylene group optionally substituted with C1-C2 alkyl or mono- or disubstituted with halogen;
- and
- R′ is hydroxy, benzyloxy, di(C1-C6)alkylaminoethyloxy, acetoxymethyl, pivaloyloxymethyl, phthalidoyl, ethoxycarbonyloxyethyl, 5-methyl-2-oxo-1,3-dioxol-4-yl methyl, or (C1-C6)alkoxy optionally substituted by N-morpholino or di(C1-C6)alkylamino.
21 more elements
A method for reducing serum uric acid levels, which method comprises administering to a mammal in need of such treatment an effective amount of a compound of formula I.
A method for treating or preventing gout, which method comprises administering to a mammal an effective amount of a compound of formula I.
A pharmaceutical composition which comprises a compound of Formula I and an ACE inhibitor, together with a pharmaceutically acceptable carrier and/or diluent.
A compound of the formula:
- 160
- wherein
- RA1 represents cyano or —N(Re)2 where each Re is independently C1-C6 alkyl;
- and
- each R3 is independently hydrogen, halogen, hydroxy, (C1-C6)alkyl, (C1-C6)haloalkyl, amino, (C1-C6)alkylamino, di(C1-C6)alkylamino, aryl, aryl alkyl, —SR15 or —OR15, where R15 is (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl where each aryl is optionally mono-, di-, or trisubstituted with halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6) alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 or N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy.
2 more elements
A compound of the formula:
- 161
- wherein
- Re is independently C1-C6 alkyl;
- and
- each R3 is independently hydrogen, halogen, hydroxy, (C1-C6)alkyl, (C1-C6)haloalkyl, amino, (C1-C6)alkylamino, di(C1-C6)alkylamino, aryl, aryl alkyl, —SR15 or —OR15, where R15 is (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl where each aryl is optionally mono-, di-, or trisubstituted with halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 or N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy.
2 more elements
A compound of the formula:
- 162
- wherein
- Hal is a halogen;
- Re is C1-C6 alkyl;
- and
- each R3 is independently hydrogen, halogen, hydroxy, (C1-C6)alkyl, (C1-C6)haloalkyl, amino, (C1-C6)alkylamino, di(C1-C6)alkylamino, aryl, aryl alkyl, —SR15 or —OR15, where R15 is (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl where each aryl is optionally mono-, di-, or trisubstituted with halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 or N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy.
3 more elements
A compound of the formula:
- 163
- wherein
- Re is C1-C6 alkyl;
- and
- each R3 is independently hydrogen, halogen, hydroxy, (C1-C6)alkyl, (C1-C6)haloalkyl, amino, (C1-C6)alkylamino, di(C1-C6)alkylamino, aryl, aryl alkyl, —SR15 or —OR15, where R15 is (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl where each aryl is optionally mono-, di-, or trisubstituted with halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 or N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy.
2 more elements
A compound of the formula:
- 164
- A is a C1-C4 alkylene group optionally substituted with C1-C2 alkyl or mono- or disubstituted with halogen;
- Re is C1-C6 alkyl;
- and
- each R3 is independently hydrogen, halogen, hydroxy, (C1-C6)alkyl, (C1-C6)haloalkyl, amino, (C1-C6)alkylamino, di(C1-C6)alkylamino, aryl, aryl alkyl, —SR15 or —OR15, where R15 is (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl where each aryl is optionally mono-, di-, or trisubstituted with halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 or N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy.
2 more elements
A compound of the formula:
- 165
- R5a, R5b, and R5c are the same or different and represent hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy;
- RC2 and RC2′ are the same and represent C1-C6 alkoxy, hydroxy, halogen, or cyano.
A compound according to claim [previous], wherein RC2 and RC2′ are chloro.
A compound of the formula:
- 166
- wherein
- R5a, R5b, and R5c are the same or different and represent hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy;
- and
- Ar represents
- an aryl or aryl(C1-C6)alkyl group, where the aryl portion is optionally substituted with up to 5 groups independently selected from
- (1) halogen, (C1-C6)alkyl, hydroxy, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 wherein each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy;
- and
- (2) phenyl, pyridyl, furyl, and thienyl, each of which is optionally substituted with one, two, or three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR17, SR17, S(O)R17, S(O)2R17 and N(R17)2 wherein each R17 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy;
- a heteroaryl or heteroaryl(C1-C6)alkyl group, where the heteroaryl portion is optionally substituted by one, two or three groups independently selected from
- (1) halogen, (C1-C6)alkyl, hydroxy, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR27, SR27, S(O)R27, S(O)2R27 and N(R27)2 wherein each R27 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy;
- and
- (2) phenyl, pyridyl, furyl, and thienyl, each of which is optionally substituted with one, two, or three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR37, SR37, S(O)R37, S(O)2R37 and N(R37)2 wherein each R37 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy.
10 more elements
A compound of the formula:
- 167
- wherein
- R5a, R5b, and R5c are the same or different and represent hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy;
- and
- each Re is independently C1-C6 alkyl.
2 more elements
A compound of the formula:
- 168
- wherein
- R5a, R5b, and R5c are the same or different and represent hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy;
- and
- each Re is independently C1-C6 alkyl.
2 more elements
A compound of the formula:
- 169
- wherein
- R5a and R5b are the same or different and represent hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C()haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy;
- and
- each Re is independently C1-C6 alkyl.
2 more elements
A compound of the formula:
- 170
- wherein
- R5a and R5b are the same or different and represent hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy;
- and
- each Re is independently C1-C6 alkyl.
2 more elements
A compound of the formula:
- 171
- wherein
- RF1 is halogen or R5;
- RF2 is halogen;
- RF3 is hydroxy, C1-C6 alkoxy, hydroxy, halogen, or cyano;
- and
- R5, R5b and R5c are independently hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6) haloalkyl, (C2-C6) haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy.
4 more elements
A compound according to claim previous, where RF1 and RF2 are both chloro.
A compound of the formula:
- 172
- wherein
- RF3 is cyano or 2-benzothiazolyl;
- and
- R5, R5b and R5a are independently hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy.
2 more elements
A compound of the formula:
- 173
- where
- RF3 is vinyl, formyl, or cyano;
- Re is C1-C6 alkyl;
- and
- R5, R5b and R5c are independently hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy.
3 more elements
A compound of the formula:
- 174
- where Re represents C1-C6 alkyl;
- and
- Re is C1-C6 alkyl;
- and
- R5, R5b and R5c are independently hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy.
3 more elements
A compound of the formula:
- 175
- A is a C1-C4 alkylene group optionally substituted with C1-C2 alkyl or mono- or disubstituted with halogen;
- Re is C1-C6 alkyl;
- and
- R5, R5b and R5c are independently hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy.
2 more elements
A compound of the formula:
- 176
- Z is a bond, O, S, C(O)NH, or C1-C6 alkylene optionally substituted with C1-C2 alkyl;
- and
- Ar represents
- an aryl or aryl(C1-C6)alkyl group, where the aryl portion is optionally substituted with up to 5 groups independently selected from
- (1) halogen, (C1-C6)alkyl, hydroxy, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 wherein each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy;
- and
- (2) phenyl, pyridyl, furyl, and thienyl, each of which is optionally substituted with one, two, or three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR17, SR17, S(O)R17, S(O)2R17 and N(R17)2 wherein each R17 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy;
- a heteroaryl or heteroaryl(C1-C6)alkyl group, where the heteroaryl portion is optionally substituted by one, two or three groups independently selected from
- (1) halogen, (C1-C6)alkyl, hydroxy, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR27, SR27, S(O)R27, S(O)2R27 and N(R27)2 wherein each R27 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy;
- and
- (2) phenyl, pyridyl, furyl, and thienyl, each of which is optionally substituted with one, two, or three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR37, SR37, S(O)R37, S(O)2R37 and N(R37)2 wherein each R37 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy;
- A is a C1-C4 alkylene group optionally substituted with C1-C2 alkyl or mono- or disubstituted with halogen;
- Re is C1-C6 alkyl;
- and
- R5, R5b and R5c are independently hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, aryl alkyl, or aryl where each aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (Cl-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 where each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 haloalkoxy.
13 more elements
Dependencies are inferred from the claim text.