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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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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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    • C07D—HETEROCYCLIC COMPOUNDS
    • 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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