OA12453A - Pyridazinone aldose reductase inhibitors. - Google Patents

Pyridazinone aldose reductase inhibitors. Download PDF

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OA12453A
OA12453A OA1200300222A OA1200300222A OA12453A OA 12453 A OA12453 A OA 12453A OA 1200300222 A OA1200300222 A OA 1200300222A OA 1200300222 A OA1200300222 A OA 1200300222A OA 12453 A OA12453 A OA 12453A
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sulfonyl
pyridazin
benzofuran
chloro
compound
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OA1200300222A
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Banavara Lakshman Mylari
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Pfizer Prod Inc
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
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    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
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    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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Claims (14)

1 / ' ’ Ο 1 245 3 -78- CLAIMS
1. A compound of Formula I
a prodrug thereof or a pharmaceutically acceptable sait of said compound or saidprodrug, wherein: A is S, SO or SO2; R1 and R2 are each independently hydrogen or methyl; 10 R3 is Het1, -CHR4Het1 or NReR7; R4 is hydrogen or (CrC3)alkyl; R6 is (Ci-Ce)alkyl, aryl or Het2; R7 is Het3; Het1 is pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, 15 quinazolyl, quinoxalyl, phthalazinyl, cinnolinyl, naphthyridinyl, pteridinyl, pyrazinopyrazinyl, pyrazinopyridazinyl, pyrimidopyridazinyl, pyrimidopyrimidyl,pyridopyrimidyl, pyridopyrazinyl, pyridopyridazinyl, pyrrolyl, furanyl, thienyl,imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, triazolyl,oxadiazolyl, thiadiazolyl, tetrazolyl, indoiyl, benzofuranyl, benzothienyl, 20 benzimidazolyl, benzoxazolyl, benzothiazolyl, ïndazolyl, benzisoxazolyl,benzisothiazolyl, pyrrolopyridyl, furopyridyl, thienopyridyl, imidazolopyridyl,oxazolopyridyl, thiazolopyridyl, pyrazolopyridyl, isoxazolopyridyl, isothiazolopyridyl,pyrrolopyrimidyl, furopyrimidyl, thienopyrimidyl, imidazolopyrimidyl,oxazolopyrimidyl, thiazolopyrimidyl, pyrazolopyrimidyl, isoxazolopyrimidyl, 25 isothiazolopyrimîdyl, pyrrolopyrazinyl, furopyrazinyl, thienopyrazinyl, imidazolopyrazinyl, oxazolopyrazinyl, thiazolopyrazinyl, pyrazolopyrazinyl,isoxazolopyrazinyl, isothiazolopyrazinyl, pyrrolopyridazinyl, furopyridazinyl,thienopyridazinyl, imidazolopyridazinyl, oxazotopyridazinyl, thiazolopyridazinyl,pyrazolopyridazinyl, isoxazolopyridazinyl or isothiazolopyridazinyl; Het1 is optionaliy 30 substituted with up to a total of four substituents each independently selected from 01 245 3 halo, formyl, (CrCeJalkoxycarbonyl, (CrC6)alkylenyloxycarbonyl, (CrC4)alkoxy-(CrC4)alkyl, C(OH)R12R13, (CrC4)alkylcarbonylamido, (C3-C7)cycloalkylcarbonylamido,phenylcarbonylamido, benzyl, phenyl, naphthyl, imidazolyl, pyridyl, triazolyl,benzimidazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl,thienyl, benzothiazolyl, pyrrolyl, pyrazolyl, quinolyl, isoquinolyl, benzoxazolyl,pyridazinyl, pyridyloxy, pyrîdylsulfonyl, furanyl, phenoxy, thiophenoxy, (CrC4)alkylsulfenyl, (C1-C4)alkylsulfonyl, (C3-C7)cycloalkyl, (C1-C6)alkyl optionallysubstituted with up to three fiuoro, or (CrC4)alkoxy optionally substituted with up tofive fiuoro; said benzyl, phenyl, naphthyl, imidazolyl, pyridyl, triazolyl,benzimidazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl,thienyl, benzothiazolyl, pyrrolyl, pyrazolyl, quinolyl, isoquinolyl, benzoxazolyl,pyridazinyl, pyridyloxy, pyrîdylsulfonyl, furanyl, phenoxy, thiophenoxy, in thedéfinition of substituents for Het1 are optionally substituted with up to threesubstituents independently selected from hydroxy, halo, bydroxy-(Ci-C4)alkyl, (CrC4)alkoxy-(CrC4)alkyl, (CrC^alkylsulfenyl, (CrC6)alkylsulfinyl, (Ct-C6)alkylsulfonyl,(CrC6)alkyl optionally substituted with up to five fiuoro, and (CrC4)alkoxy optionallysubstituted with up to five fiuoro; said imidazolyl, oxazolyl, isoxazolyl, thiazolyl andpyrazolyl in the définition of substituents for Het1 are optionally substituted with upto two substituents independently selected from hydroxy, halo, CrC4)alkyl,hydroxy-(CrC4)alkyl, (Ci-C4)alkoxy-{CrC4)alkyl, CrC4)alkyl-phenyl optionallysubstituted in the phenyl portion with one Cl, Br, OMe, Me or SO2-phenyl whereinsaid SOz-phenyl is optionally substituted in the phenyl portion with one Cl, Br, OMe,Me, (Ci-C4)alkyl optionally substituted with up to five fiuoro, or (Ci-C4)alkœtyoptionally substituted with up to three fiuoro; R12 and R13 are each independently hydrogen or (CrC4)alkyl; Het2 and Het3 are each independently imidazolyl, pyridyl, triazolyl, benzimidazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl,thienyl, benzothiazolyl, pyrrolyl, pyrazolyl, quinolyl, isoquinolyl, benzoxazolyl,pyridazinyl, pyridyloxy, pyrîdylsulfonyl, furanyl, phenoxy, thiophenoxy; Het2 andHet3 are each independently optionally substituted with up to a total of foursubstituents each independently selected from halo, formyl, (Ci-Ce)alkoxycarbonyl,(C1-C6)alkylenyloxycarbonyl, (C1-C4)alkoxy-(C1-C4)alkyl, C(OH)R18R1S, (C-rC4)alkylcarbonylamido, (C3-C7)cycloaikylcarbonylamido, phenylcarbonylamido,phenyl, naphthyl, imidazolyl, pyridyl, triazolyl, benzimidazolyl, oxazolyl, isoxazolyl, 012453 -80- thiazolyl, oxadiazofyl, thiadiazolyl, tetrazolyl, thienyl, benzothiazolyl, pyrrolyl,pyrazolyl, quinolyl, isoquinolyt, benzoxazolyl, pyridazinyl, pyridyloxy, pyridylsulfonyl,furanyl, phenoxy, thiophenoxy, (Cr^Jalkylsulfenyl, (CrC4)alkylsulfonyl, (C3-C7)cycloalkyl, (CrC4)alkyl optionally substituted with up to three fluoro or (CrC4)alkoxy optionally substituted with up to five fluoro; said phenyl, naphthyl,imidazolyl, pyridyl, triazolyl, benzimidazolyl, oxazolyl, isoxazolyl, thiazolyl,oxadiazolyl, thiadiazolyl, tetrazolyl, thienyl, benzothiazolyl, pyrrolyl, pyrazolyl,quinolyl, isoquinolyl, benzoxazolyl, pyridazinyl, pyridyloxy, pyridylsulfonyl, furanyl,phenoxy, thiophenoxy, in the définition of substituents for Het2 and Het3 areoptionally substituted with up to three substituents independently selected fromhydroxy, halo, hydroxy-(CrC4)alkyl, (CrC4)alkoxy-(Ci-C4)alkyl, (CrC4)alkyloptionally substituted with up to five fluoro and (C,-C4)alkoxy optionally substitutedwith up to five fluoro; said imidazolyl, oxazolyl, isoxazolyl, thiazolyl and pyrazolyl inthe définition of substituents for Het2 and Het3 are optionally substituted with up totwo substituents independently selected from hydroxy, halo, hydroxy-(CrC4)alkyl,(CrC4)alkoxy-(CrC4)alkyl, (CrC^alkyl optionally substituted with up to five fluoroand (CrC4)alkoxy optionally substituted with up to three fluoro; and R18 and R19 are each independently hydrogen or (CrC4)alkyl; provided that when R3 is NR6R7, then A is SO2.
2. A compound of claim 1, a prodrug thereof or a pharmaceuticallyacceptable sait of said compound or said prodrug, wherein A is SO2; R1 and R2 areeach hydrogen; R3 is Het1 optionally substituted with up to a total of foursubstituents.
3. A compound of claim 2, a prodrug thereof or a pharmaceuticallyacceptable sait of said compound or said prodrug, wherein Het1 is 5H-furo-[3,2c]pyridin-4-one-2-yl, furano[2,3b]pyridin-2-yl, thieno[2,3b]pyridin-2-yl, indol-2-yl,indol-3-yl, benzofuran-2-yl, benzothien-2-yl, imidazo[1,2a]pyridin-3-yl, pyrrol-1-yl,imidazol-1-yl, indazol-1-yl, tetrahydroquinol-1-yl or tetrahydroindol-1-ÿl, whereinsaid Het1 is optionally independently substituted with up to a total of twosubstituents each independently selected from fluoro, chloro, bromo, (CrC6)alkyl,(CrC6)alkoxy, trifluoromethyl, hydroxy, benzyl or phenyl; said benzyl and phenylare each optionally independently substituted with up to three halo, (CrC6)alkyl,(Ci-C6)alkoxy, (CrC6)aikyJsulfonyl, (C,-C6)alkylsulfinyl, (C,-Ce)alkylsulfenyl,trifluoromethyl or hydroxy. '1 ' 012453 -81-
4. A compound of claim 3, a prodrug thereof or a pharmaceuticallyacceptable sait of said compound or said prodrug, wherein Het1 is indol-2-yl,benzofuran-2-yl, benzothlophen-2-yl, furano[2,3b]pyridin-2-yl, thieno[2,3b]pyridin-2-yl or imidazo[1,2a]pyridin-4-yl, wherein said Het1 is optionally independentlysubstituted with up to a total of two substituents each independently selected fromfluoro, chloro, bromo, (CrC6)alkyl, (CrC6)alkoxy, trifluoromethyl or phenyl; saidphenyl beîng optionally substituted with up to two substituents independentlyselected from fluoro, chloro and (CrC6)alkyl.
5. A compound of claim 4, a prodrug thereof or a pharmaceuticallyacceptable sait of said compound or said prodrug, wherein Het1 is benzofuran-2-yloptionally substituted with up to two substituents each independently selected frommethyl, methoxy, chloro, fluoro, ethyl, 4-fluorophenyi, trifluoromethyl, isopropyl,phenyl and hydroxy.
6. A compound of claim 5, a prodrug thereof or a pharmaceuticallyacceptable sait of said compound or said prodrug, wherein Het1 is 5-chloro-benzofuran-2-yl, 5,7-dichloro-benzofuran-2-yl, benzofuran-2-yl, 5-chloro-3-methyl-benzofuran-2-yl, 5-fluoro-3-methyl-benzofuran-2-yl, 3-methyl-5-trifluoromethyl-benzofuran-2-yl, 5-chloro-3-phenyl-benzofuran-2-y), 3-phenyl-benzofuran-2-yI, 3-(4-fluoro-phenyl)-benzofuran-2-yl, 5-chloro-benzofuran-2-yl and 3-ethyl-5-methyl-benzofuran-2-yl or 3-methyl-benzofuran-2-yl.
7. A compound of claim 5, a prodrug thereof or a pharmaceuticallyacceptable sait of said compound or said prodrug, wherein Het1 is 3-methylbenzofuran-2-yl, optionally substituted with up to one additional substituenteach independently selected from methyl, methoxy, chloro, fluoro, ethyl, 4-fluorophenyl, trifluoromethyl, isopropyl, phenyl and hydroxy.
8. A compound of claim 7, a prodrug thereof or a pharmaceuticallyacceptable sait of said compound or said prodrug, wherein said additionalsubstituent is 5-chloro.
9. A compound of claim 5, a prodrug thereof or a pharmaceuticallyacceptable sait of said compound or said prodrug, selected from 6-(5-chloro-3-methyl-benzofuran-2-su!fonyl)-2H-pyridazin-3-one, 6-(5-fluoro-3-methyl-benzofuran-2-sulfonyl)-2H-pyridazin-3-one and 6-(5-trifluoromethyl-3-methyl-benzofuran-2-sulfonyl)-2H-pyridazin-3-one. ο Ί 24 5 3 -82-
10. A compound selected from 6-(indole-2-sulfonyl)-2H-pyridazin-3-one;6~(5-chloro-3-methyl-benzofuran-2-sulfonyl)-2H-pyrîdazin-3-one; 6-(5-chloro-3-metbyl-benzofuran-2-sulfonyl)-2H-pyridazin-3-one; 6-(benzofuran-2~sulfonyl)-2H-pyridazin-3-one; 6-(5-methoxy-benzofuran-2-sulfonyl)-2H-pyridazin-3-one; 6-(3,5- 5 dÎmethyl-benzofuran-2-sulfonyl)-2H-pyridazin-3-one; 6-(5,7-dichloro-benzofuran-2-sulfonyl)-2H-pyridazin-3-one; 6-(5-chloro-benzofuran-2-sulfonyl)-2H-pyridazin-3-one;6-(3-methyl-benzofuran-2-sulfonyl)-2H-pyridazin-3-one; 6-(5-trifluoromethyl-3-methylbenzofuran-2-suIfonyl)-2H-pyridazin-3-one; 6-(5-chloro-3-isopropyl-benzofuran-2-sulfonyl)-2H-pyridazin-3-one; 6-(5-fluoro-3-methyl-benzofuran-2-sulfonyl)-2H- 10 pyrtdazin-3-one; 6-(6-chloro-3-methyl-benzofuran-2-sulfonyl)-2H-pyridazin-3-oné; 6-(3-hydroxy-benzofuran-2-sulfonyl)-2H-pyridazin-3-one; 6-(5-chloro-3-hydroxy-benzofuran-2-sulfonyl)-2H-pyridazin-3-one; 6-(5-chIoro-3-methyl-benzothiophene-2-sulfonyl)-2H-pyridazin-3-one; 6-(5-methyI-benzothiophene-2-sulfonyl)-2H-pyridazin-3one; 6-benzothiophene-2-sulfonyl)-2H-pyridazin-3-one; 6-(3-phenyI-benzofuran-2- 15 sulfonyl)-2H-pyridazin-3-one; 6-(3-[4-fluorophenyl]-benzofuran-2-rnethylsulfonyl)-2H-pyridazin-3-one; 6-(thieno[2,3 bjpyridine -2-sulfonyl)-2H-pyridazin-3-one; 2-(6-oxo-1,6-dihydro-pyridazine-3-sulfonyI)-5H-furo[3.2-c]pyridin-4-one; 6-(5-chloro-3-ethyl-benzofuran-2-sulfonyl)-2H-pyridazin-3-one; 6-(imidazo[1,2a]pyridine-3-sulfonyl)-2H-pyridazin-3-one; 6-(6-chloro-indole-2-sulfonyl)-2H-pyridazin-3-one; 6-(5-methoxy- 20 indole-2-sulfonyl)-2H-pyridazin-3-one; 6-(5-chloro-indole-2-sulfonyl)-2H-pyridazin-3-one; 6-(6-fluoro-indole-2-sulfonyl)-2H-pyridazin-3-one; 6-(5,6-methylenedioxy-indole-2-sulfonyl)-2H-pyridazin-3-one; 6-(7-chloro-indole-2-sulfonyl)-2H-pyridazin-3-one; 6-(5-chloro-3-phenyl-2-sulfonyl)-2H-pyridazin-3-one; 6-(3-chloro-indole-2-sulfonyl)-2H-pyridazin-3-one; 6-(N-benzylindole-5-sulfonyl)-2H-pyridazin-3-one; 6-(5-chloro-3- 25 methyl-benzofuran-2-methylsulfonyl)-2H-pyridazin-3-one; 6-(indole-3-sulfonyl)-2H-pyridazin-3-one;6-(N-methylindole-2-suIfonyl)-2H-pyridazin-3-one; 6-(pyrrole-1-sulfonyI)2H-pyridazin-3-one; 6-(imidazole-1 -sulfonyl)2H-pyridazin-3-one; 6-(indole-1 -sulfonyl)2H-pyridazin-3-one; 6-(3-chloro-indole-1 -sulfonyl)2H-pyridazin-3-one; 6-(3-chloro-indazole-1 -sulfonyl)2H-pyridazin-3-one; 6-(3-methyl-indole-1 -sulfonyl)-2H- 30 pyridazin-3-one; 6-(tetrahydroquinoline-1-sulfonyI)-2K-pyridazin-3-one; 6-(3-(4- fluorophenyl]-benzofuran-2-siilfonyl)-2H-pyridazin-3-one; 6-(imidazo[1,2a]pyridine-4-sulfonyl)-2H-pyridazin-3-one and 6-(2,3-tetrahÿdro-indole-1-sulfonyl)2H-pyridazin-3- one. 012453 -SS-
11. A pharmaceutical composition comprising a compound of daim 1, aprodrug thereof or a pharmaceutically acceptable sait of said compound or saidprodrug, and a pharmaceutically acceptable vehicte, carrier or diluent.
12. Use of a compound of daim 1, s a prodrug thereof or a pharmaceutically5 acceptable sait thereof in the manufacture of a médicament for treating cardiac tissue ischemia in a mammal.
13. Use of a compound of claim 1, a prodrug thereof or a pharmaceuticallyacceptable sait of said compound or said prodrug în the manufacture of a médicament for î θ treating one or more diabetic complications in a mammal suffering therefrom. 14. 3-Meihoxy-6-(5-chioro-3-methyl-benzofuran-2-suifenyl)-pyridazine, 3-methoxy-6-(5-chloro-3-methyl-benzofuran-2-suîfonyl}-pyridazine or 3-methoxy-6-(5-chloro-3-methyl-benzofuran-2-sulfinyl)-pyridazîne.
15. The sodium sait of 6-(5-chloro-3-methyl-benzofuran-2-sulfonyI)-2H-15 pyridazin-3-one.
OA1200300222A 2001-03-30 2002-01-31 Pyridazinone aldose reductase inhibitors. OA12453A (en)

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Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1094757C (zh) 1996-07-24 2002-11-27 沃尼尔·朗伯公司 用于治疗疼痛的异丁基γ－氨基丁酸及其衍生物
ES2240657T3 (es) * 2001-02-28 2005-10-16 Pfizer Products Inc. Compuestos de sulfonilpiridazinona utiles como inhibidores de aldosa reductasa.
EE200300470A (et) * 2001-03-30 2004-02-16 Pfizer Products Inc. Aldoosreduktaasi püridasinooninhibiitorid
AU761191B2 (en) * 2001-05-24 2003-05-29 Pfizer Products Inc. Therapies for tissue damage resulting from ischemia
IL162594A0 (en) * 2002-01-09 2005-11-20 Pfizer Prod Inc Process and intermediates for pyridazinone antidiabetic agents
US7419981B2 (en) * 2002-08-15 2008-09-02 Pfizer Inc. Synergistic combinations of an alpha-2-delta ligand and a cGMP phosphodieterse 5 inhibitor
US20040092522A1 (en) * 2002-08-15 2004-05-13 Field Mark John Synergistic combinations
US6872833B2 (en) * 2003-04-14 2005-03-29 Hoffmann-La Roche Inc. Adenosine receptor ligands
US8017634B2 (en) 2003-12-29 2011-09-13 President And Fellows Of Harvard College Compositions for treating obesity and insulin resistance disorders
US7262318B2 (en) * 2004-03-10 2007-08-28 Pfizer, Inc. Substituted heteroaryl- and phenylsulfamoyl compounds
AR049384A1 (es) 2004-05-24 2006-07-26 Glaxo Group Ltd Derivados de purina
DE602005025755D1 (de) 2004-06-04 2011-02-17 Teva Pharma Irbesartan enthaltende pharmazeutische zusammensetzung
US20050288340A1 (en) * 2004-06-29 2005-12-29 Pfizer Inc Substituted heteroaryl- and phenylsulfamoyl compounds
WO2006028565A2 (fr) * 2004-06-30 2006-03-16 Whitehead Institute For Biomedical Research Procedes pour analyse de site haut rendement au niveau du genome
GB0514809D0 (en) 2005-07-19 2005-08-24 Glaxo Group Ltd Compounds
US7741317B2 (en) 2005-10-21 2010-06-22 Bristol-Myers Squibb Company LXR modulators
US7888376B2 (en) 2005-11-23 2011-02-15 Bristol-Myers Squibb Company Heterocyclic CETP inhibitors
KR20080114688A (ko) * 2006-01-13 2008-12-31 와이어쓰 5-히드록시트립타민 수용체에 대한 리간드로서의 술포닐 치환된 1ｈ-인돌
PT2248812E (pt) 2006-06-27 2014-03-12 Takeda Pharmaceutical Compostos cíclicos fundidos como moduladores do receptor gpr40
ATE547394T1 (de) 2006-12-01 2012-03-15 Bristol Myers Squibb Co N-((3-benzyl)-2,2-(bis-phenyl)-propan-1- aminderivate als cetp-hemmer für die behandlung von atherosklerose und herz-kreislauf- erkrankungen
US8173645B2 (en) * 2007-03-21 2012-05-08 Takeda San Diego, Inc. Glucokinase activators
JP2010043063A (ja) 2008-05-09 2010-02-25 Agency For Science Technology & Research 川崎病の診断及び治療
JP5815552B2 (ja) 2009-12-08 2015-11-17 ケース ウェスタン リザーブ ユニバーシティＣａｓｅ Ｗｅｓｔｅｒｎｒｅｓｅｒｖｅ Ｕｎｉｖｅｒｓｉｔｙ 眼疾患を治療する化合物および方法
US8916563B2 (en) 2010-07-16 2014-12-23 The Trustees Of Columbia University In The City Of New York Aldose reductase inhibitors and uses thereof
CA2848877A1 (fr) * 2011-09-15 2013-03-21 Taipei Medical University Utilisation d'indolyl et d'hydroxamates d'indolinyl pour le traitement d'une defaillance cardiaque ou d'une lesion neuronale
US9339542B2 (en) * 2013-04-16 2016-05-17 John L Couvaras Hypertension reducing composition
SG11201507496UA (en) 2013-04-17 2015-11-27 Pfizer N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases
CN103739547B (zh) * 2014-01-03 2015-09-02 沈阳药科大学 2-[6-甲氧基-3-(2,3-二氯苯基)甲基-4-氧代-1,4-二氢-1(4h)-喹啉基]乙酸的合成方法
WO2016055901A1 (fr) 2014-10-08 2016-04-14 Pfizer Inc. Composés d'amide substitué
EP3283074A4 (fr) * 2015-04-14 2018-12-05 Case Western Reserve University Compositions et procédés de modulation de l'activité de la déshydrogénase à chaîne courte
WO2017168174A1 (fr) 2016-04-02 2017-10-05 N4 Pharma Uk Limited Nouvelles formes pharmaceutiques du sildénafil
EP4316603A3 (fr) 2016-06-21 2024-04-17 The Trustees of Columbia University in the City of New York Composés de 4-oxo-3,4-dihydrothiéno[3,4-d!pyridazine utilisés comme inhibiteurs de l'aldose réductase et leurs procédés d'utilisation
WO2018002673A1 (fr) 2016-07-01 2018-01-04 N4 Pharma Uk Limited Nouvelles formulations d'antagonistes du récepteur de l'angiotensine ii
WO2018058109A1 (fr) * 2016-09-26 2018-03-29 Nusirt Sciences, Inc. Compositions et méthodes pour le traitement de troubles métaboliques
JP2020502070A (ja) 2016-11-30 2020-01-23 ケース ウエスタン リザーブ ユニバーシティ １５−ｐｇｄｈ阻害剤とコルチコステロイドおよび／またはｔｎｆ阻害剤との組み合わせならびにその使用
JP2020514323A (ja) 2017-02-06 2020-05-21 ケース ウエスタン リザーブ ユニバーシティ 短鎖デヒドロゲナーゼ活性を調節する組成物と方法
EP4417260A2 (fr) 2017-07-28 2024-08-21 Applied Therapeutics, Inc. Compositions et procédés pour traiter la galactosémie
SG11202107614PA (en) 2019-01-18 2021-08-30 Astrazeneca Ab Pcsk9 inhibitors and methods of use thereof
AU2020268368A1 (en) 2019-05-07 2022-01-06 Ucl Business Ltd Treatment and detection of inherited neuropathies and associated disorders
MX2021014441A (es) 2019-05-31 2022-01-06 Ikena Oncology Inc Inhibidores del dominio asociado mejorador de la transcripcion (tead) y usos de los mismos.
CA3142351A1 (fr) 2019-05-31 2020-12-03 Ikena Oncology, Inc. Inhibiteurs de tead et leurs utilisations
WO2022120353A1 (fr) * 2020-12-02 2022-06-09 Ikena Oncology, Inc. Inhibiteurs de tead et leurs utilisations

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE47592B1 (en) 1977-12-29 1984-05-02 Ici Ltd Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture
US4939140A (en) 1985-11-07 1990-07-03 Pfizer Inc. Heterocyclic oxophthalazinyl acetic acids
US4996204A (en) 1989-05-11 1991-02-26 Pfizer Inc. Pyrido[2,3-d]pyridazinones as aldose reductase inhibitors
FR2647676A1 (fr) 1989-06-05 1990-12-07 Union Pharma Scient Appl Nouveaux derives de pyridazinone, leurs procedes de preparation, medicaments les contenant, utiles notamment comme inhibiteurs de l'aldose reductase
EP0516860A4 (en) * 1990-11-30 1993-12-01 Tsumura & Co. Chromone derivative and aldose reductase inhibitor containing the same as active ingredient
AU658887B2 (en) 1991-03-28 1995-05-04 Pfizer Inc. Pyridazinone acetic acids as aldose reductase inhibitors
US5834466A (en) 1994-12-22 1998-11-10 The Regents Of The University Of California Method for protecting of heart by limiting metabolic and ionic abnormalities developed during ischemia, following ischemia or resulting from ischemia
TWI238064B (en) 1995-06-20 2005-08-21 Takeda Chemical Industries Ltd A pharmaceutical composition for prophylaxis and treatment of diabetes
SK3902000A3 (en) * 1997-09-24 2000-12-11 Orion Corp Bisethers of 1-oxa, aza and thianaphthalen-2-ones as phospholamban inhibitors
FR2822827B1 (fr) * 2001-03-28 2003-05-16 Sanofi Synthelabo Nouveaux derives de n-(arylsulfonyl) beta-aminoacides comportant un groupe aminomethyle substitue, leur procede de preparation et les compositions pharmaceutiques en contenant
EE200300470A (et) * 2001-03-30 2004-02-16 Pfizer Products Inc. Aldoosreduktaasi püridasinooninhibiitorid
HUP0303920A3 (en) * 2001-04-30 2004-07-28 Pfizer Prod Inc Pharmaceutical compositions containing combinations of aldose reductase inhibitor pyridazinons and cyclooxygenase 2 inhibitors
IL162594A0 (en) * 2002-01-09 2005-11-20 Pfizer Prod Inc Process and intermediates for pyridazinone antidiabetic agents

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