Substituted heteroarylalkanoic acids
First Claim
Patent Images
1. 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
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.
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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.
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Citations
78 Claims
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1. 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 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.- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 78)
(B) a heterocyclic 5-membered ring having one nitrogen, oxygen or sulfur, two nitrogens one of which may be replaced by oxygen or sulfur, or three nitrogens one of which may be replaced by oxygen or sulfur, said heterocyclic 5-membered ring substituted by one or two fluoro, chloro, (C1-C6)alkyl or phenyl, or condensed with benzo, or substituted by one of pyridyl, furyl or thienyl, the phenyl and benzo rings being optionally substituted by one of iodo, cyano, nitro, perfluoroethyl, trifluoroacetyl, or (C1-C6)alkanoyl, one or two of fluoro, chloro, bromo, hydroxy, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, trifluoromethoxy, trifluoromethylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl or trifluoromethyl, or two fluoro or two trifluoromethyl with one hydroxy or one (C1-C6)alkoxy, or one or, preferably, two fluoro and one trifluoromethyl, or three fluoro, said pyridyl, furyl or thienyl optionally substituted in the 3-position by fluoro, chloro, bromo, (C1-C6)alkyl or (C1-C6)alkoxy;
(C) a heterocyclic 6-membered ring having one to three nitrogen atoms, or one or two nitrogen atoms and one oxygen or sulfur, said heterocyclic 6-membered ring substituted by one or two (C1-C6)alkyl or phenyl, or condensed with benzo, or substituted by one of pyridyl, furyl or thienyl, said phenyl or benzo optionally substituted by one of iodo or trifluoromethylthio, or one or two of fluoro, chloro, bromo, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, or trifluoromethyl, and said pyridyl, furyl or thienyl optionally substituted in the 3-position by fluoro, chloro, (C1-C6)alkyl or (C1-C6)alkoxy;
said benzo-condensed heterocyclic 5-membered or 6-membered rings optionally substituted in the heterocyclic 5-membered or 6-membered ring by one of fluoro, chloro, bromo, methoxy, or trifluoromethyl;
(D) oxazole or thiazole condensed with a 6-membered aromatic group containing one or two nitrogen atoms, with thiophene or with furane, each optionally substituted by one of fluoro, chloro, bromo, trifluoromethyl, methylthio or methylsulfinyl;
(E) imidazolopyridine or triazolopyridine optionally substituted by one of trifluoromethyl, trifluoromethylthio, bromo, or (C1-C6)alkoxy, or two of fluoro or chloro;
(F) thienothiophene or thienofuran optionally substituted by one of fluoro, chloro or trifluoromethyl;
(G) thienotriazole optionally substituted by one of chloro or trifluoromethyl;
(H) naphthothiazole;
naphthoxazole;
or thienoisothiazole.
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3. A compound according to claim 1, wherein Z is (C1-C6)alkylene and Ar is a substituted phenyl of Formula II or a substituted benzothiazole of Formula III
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4. A compound according to claim 3, wherein R8, R8′
- , R9, R9′
, R10, R11, R12, R13 and R14 are independently hydrogen, hydroxy, (C1-C6)alkoxy, halogen, (C1-C6)alkyl, halogen, (C1-C6)haloalkyl, cyano, nitro, or N(R7)2 wherein each R7 is independently hydrogen or C1-C6 alkyl.
- , R9, R9′
-
5. A compound according to claim 4, wherein R8, R8′
- , R9, R9′
, R10, R11, R12, R13 and R14 are independently hydrogen, fluorine, chlorine, bromine, trifluoromethyl or nitro.
- , R9, R9′
-
6. A compound according to claim 4, wherein Z is (C1-C3)alkylene and Ar is
-
7. A compound according to claim 6, wherein D is selected from:
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8. A compound according to claim 7, wherein A and Z are both methylene.
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9. A compound according to claim 8, wherein R′
- is hydroxy or C1-C6 alkoxy.
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10. A compound according to claim 9, wherein D is
-
11. A compound according to claim 9 where D is
-
12. A compound according to claim 9, wherein D is
-
13. A compound according to claim 9, where D is
-
14. A compound according to claim 13, wherein D is
-
15. A compound according to claim 6, wherein D is
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16. A compound according to claim 15, where D is
-
17. A compound according to claim 15, where D is
-
18. A compound according to claim 15, where D is
-
19. A compound according to claim 7, wherein R11, R12, R13 and R14 are independently hydrogen, hydroxy, (C1-C2)alkoxy, trifluoromethyl, (C1-C3)alkyl, fluoro, chloro, bromo, nitro, amino, mono(C1-C2)alkylamino or di(C1-C2)alkylamino.
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20. A compound according to claim 7, wherein R11, R12, R13 and R14 are independently hydrogen, hydroxy, fluoro, chloro, nitro, or amino.
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21. A compound according to claim 7, wherein three of R11, R12, R13 and R14 are fluoro and the other is hydrogen.
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22. A compound according to claim 7 where at least one of R11, R12, R13, and R14 is trifluoromethyl.
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23. A compound according to claim 14, wherein R12 is trifluoromethyl.
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24. A compound according to claim 10, wherein R11, R12, and R14 represent fluorine and R13 is hydrogen.
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25. A compound according to claim 22, wherein R11, R12, and R14 represent fluorine and R13 is hydrogen.
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26. A compound according to claim 7, wherein R′
- is hydrogen.
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27. A compound according to claims 7, wherein R′
- is C1-C6 alkoxy.
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28. A compound according to claim 1, which is
[6-Ethyl-3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid. -
29. A compound according to claim 1, which is
[6-Methyl-3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-l-yl]-acetic acid. -
30. A compound according to claim 1, which is
[3-(4,5,7-Trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid. -
31. A compound according to claim 1, which is
[2,6-Dimethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
32. A compound according to claim 1, which is
[2,6-Diethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
33. A compound according to claim 1, which is
[2,6-Diphenyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
34. A compound according to claim 1, which is
[2,6-Dipropyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
35. A compound according to claim 1, which is
[5-(4,5,7-Trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
36. A compound according to claim 1, which is
[2,4,6-Trimethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
37. A compound according to claim 1, which is
[4-Ethyl-2,6-dimethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
38. A compound according to claim 1, which is
[2-Ethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
39. A compound according to claim 1, which is
[2-Benzyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
40. A compound according to claim 1, which is
[2-Phenyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
41. A compound according to claim 1, which is
[6-Ethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
42. A compound according to claim 1, which is
[6-Phenyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
43. A compound according to claim 1, which is
[6-Benzyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
44. A compound according to claim 1, which is
[2-Phenoxy-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]-acetic acid. -
45. A compound according to claim 1, which is
[5-(4,5,7-Trifluoro-benzothiazol-2-ylmethyl)-thiophen-2-yl]-acetic acid. -
46. A compound according to claim 1, which is
[3-Methyl-4-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-2-yl]-acetic acid. -
47. A compound according to claim 1, which is
[4-(4,5,7-Trifluoro-benzothiazol-2-ylmethyl)-thiophen-2-yl]-acetic acid. -
48. A compound according to claim 1, which is
[2-(4,5,7-Trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetic acid. -
49. A compound according to claim 1, which is
[4-Methyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetic acid. -
50. A compound according to claim 1, which is
[5-(4,5,7-Trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetic acid. -
51. A compound according to claim 1, which is
[2,5-Dimethyl-4-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetic acid. -
52. A compound according to claim 1, which is
[2-(4,5,7-Trifluoro-benzothiazol-2-ylmethyl)-thiazol-4-yl]-acetic acid. -
53. A method of preventing or alleviating chronic complications arising from diabetes mellitus, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 1.
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54. A method according to claim 52 wherein the complications are selected from the group consisting of diabetic cataracts, retinopathy, nephropathy and neuropathy.
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78. A compound according to claim 1 which is
[6-methyl-3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid (m)ethyl ester; -
[3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid (m)ethyl ester;
2,6-Dimethyl-5-(4,5,7-trifluoro-benzothiazole-2-ylmethyl)-pyridin-3-yl-acetic acid hydrochloride (m)ethyl ester;
[2,6-Diethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]acetic acid methyl ester;
[2,6-Diphenyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]acetic acid (m)ethyl ester;
[2,6-Dipropyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl]acetic acid methyl ester;
5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid (m)ethyl ester;
2,4,6-trimethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid (m)ethyl ester;
2,6-dimethyl-4-ethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid (m)ethyl ester;
2-Ethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid (m)ethyl ester;
2-benzyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid (m)ethyl ester;
2-phenyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid (m)ethyl ester;
6-Phenyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid (m)ethyl ester;
6-Benzyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid methyl ester;
2-phenoxy-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl)-acetic acid methyl ester;
[2,5-dimethyl-4-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetic acid (m)ethyl ester;
[5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-2-yl]-acetic acid;
[4-(4,5,7-Trifluoro-benzothiazol-2-ylmethyl)-thiophen-2-yl]-acetic acid methyl ester;
[4-(5-trifluoromethybenzothiazol-2-ylmethyl)-thiophen-2-yl]-acetic acid (m)ethyl ester;
[2-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetic acid (m)ethyl ester;
[4-methyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetic acid methyl ester;
ora pharmaceutically acceptable salt thereof.
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55. 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.
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56. A method for treating or preventing gout, which method comprises administering to a mammal an effective amount of a compound of formula I.
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57. A pharmaceutical composition which comprises a compound of Formula I and an ACE inhibitor, together with a pharmaceutically acceptable carrier and/or diluent.
-
58. A compound of the formula:
- 59. A compound of the formula:
-
60. A compound of the formula:
-
62. A compound of the formula:
-
63. A compound of the formula:
-
64. A compound of the formula:
-
65. A compound according to claim [previous], wherein RC2 and RC2′
- are chloro.
-
66. A compound of the formula:
-
67. A compound of the formula:
-
68. A compound of the formula:
-
69. A compound of the formula:
-
70. A compound of the formula:
-
71. A compound of the formula:
-
72. A compound according to claim previous, where RF1 and RF2 are both chloro.
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73. A compound of the formula:
-
74. A compound of the formula:
-
75. A compound of the formula:
-
76. A compound of the formula:
-
77. A compound of the formula:
Specification
-
- Resources
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Current AssigneeThe Institute For Pharmaceutical Discovery, LLC
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Original AssigneeThe Institutes for Pharmaceutical Discovery, LLC
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InventorsZandt, Michael C. Van, Geraci, Leo
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current514/265.1
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CPC Class CodesA61P 19/06 Antigout agents, e.g. antih...A61P 25/00 Drugs for disorders of the ...A61P 27/02 Ophthalmic agentsA61P 27/12 for cataractsA61P 3/10 for hyperglycaemia, e.g. an...C07D 207/337 Radicals substituted by car...C07D 211/90 Carbon atoms having three b...C07D 213/26 Radicals substituted by hal...C07D 213/30 Oxygen atomsC07D 213/57 NitrilesC07D 213/61 Halogen atoms or nitro radi...C07D 213/80 in position 3C07D 309/38 one oxygen atom in position...C07D 417/06 linked by a carbon chain co...C07D 487/04 Ortho-condensed systems
