DK2262500T3 - Thienopyridonderivater som amp-aktiverede proteinkinase-(ampk)-aktivatorer - Google Patents

Thienopyridonderivater som amp-aktiverede proteinkinase-(ampk)-aktivatorer Download PDF

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DK2262500T3
DK2262500T3 DK09731265.6T DK09731265T DK2262500T3 DK 2262500 T3 DK2262500 T3 DK 2262500T3 DK 09731265 T DK09731265 T DK 09731265T DK 2262500 T3 DK2262500 T3 DK 2262500T3
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hydroxy
pyridin
chloro
phenyl
thieno
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DK09731265.6T
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English (en)
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Daniel Cravo
Franck Lepifre
Sophie Hallakou-Bozec
Christine Charon
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Merck Patent Gmbh
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    • C—CHEMISTRY; METALLURGY
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system

Claims (10)

1. Forbindelse med formlen (I)
(I) hvor: R1 betegner Hal, R2, R3 hver, uafhængigt af hinanden, betegner Ar eller Het, Ar betegner phenyl, naphthyl, der hver er usubstitueret eller mono-, di-, tri-, tetra- eller pentasubstitueret med A, Hal, OA, OH, CHO, COA, NH2, NHA, NA2, NO2, COOA, COOH, CONH2, CONHA, CONA2, SO2A, CN, C(=NH)NH2, C(=NH)NHOH og/eller Het, Het betegner en mono- eller bicyklisk aromatisk heterocyklus med 1 til 4 N-, O- og/eller S-atomer, der kan være mono-, di- eller trisubstitueret med Hal, A, OA, OH, CHO, COA, COOH, COOA, CN, NO2, NH2, NHA, NA2, CONH2, CONHA og/eller CONA2, A betegner uforgrenet eller forgrenet alkyl med 1-10 C-atomer, hvor 1-7 H-atomer kan erstattes af OH, F, Cl og/eller Br, eller betegner cycloalkyl med 3-7 C-atomer, Hal betegner F, Cl, Br eller I, og farmaceutisk anvendelige salte, solvater og stereoisomerer deraf, herunder blandinger deraf i alle forhold.
2. En forbindelse ifølge krav 1 hvor R2 betegner phenyl, naphthyl der hver er usubstitueret eller mono-, di-, tri-, tetra- eller pentasubstitueret med A, Hal, OA, OH, COOA, COOH, CONH2, CONHA, CONA2 og/eller SO2A eller betegner Het, og farmaceutisk anvendelige salte og stereoisomerer deraf, herunder blandinger deraf i alle forhold.
3. En forbindelse ifølge et eller flere af krav 1-3 hvor R3 betegner phenyl, naphthyl, der hver er usubstitueret eller mono-, di-, tri-, tetra- eller pentasubstitueret med A, Hal, OA, OH, NH2, NHA, NA2, COOA, COOH, CONH2, CONHA, CONA2, SO2A, CN, C(=NH)NH2 og/eller C(=NH)NHOH eller betegner Het, og farmaceutisk anvendelige salte og stereoisomerer deraf, herunder blandinger deraf i alle forhold.
4. En forbindelse ifølge et eller flere af krav 1-3 hvor Het betegner pyridyl, pyrimidinyl, furanyl, isoxazolyl, imidazolyl, pyrazolyl, oxazolyl, pyrrolyl, thiazolyl, isothiazolyl, thienyl, triazolyl, tetrazolyl, indolyl, benzimidazolyl eller indazolyl, og farmaceutisk anvendelige salte og stereoisomerer deraf, herunder blandinger deraf i alle forhold.
5. En forbindelse ifølge et eller flere af krav 1-4 hvor A betegner uforgrenet eller forgrenet alkyl med 1-10 C-atomer, hvor 1-7 H-atomer kan erstattes af OH, F, Cl og/eller Br, og farmaceutisk anvendelige salte og stereoisomerer deraf, herunder blandinger deraf i alle forhold.
6. En forbindelse ifølge et eller flere af krav 1-5 hvor R1 betegner Hal, R2 betegner phenyl, naphthyl, der hver er usubstitueret eller mono-, di-, tri-, tetra- eller pentasubstitueret med A, Hal, OA, OH, COOA, COOH, CONH2, CONHA, CONA2 og/eller SO2A eller betegner Het, R3 betegner phenyl, naphthyl, der hver er usubstitueret eller mono-, di-, tri-, tetra- eller pentasubstitueret med A, Hal, OA, OH, NH2, NHA, NA2, COOA, COOH, CONH2, CONHA, CONA2, SO2A, CN, C(=NH)NH2 og/eller C(=NH)NHOH eller betegner Het, Het betegner en mono- eller bicyklisk aromatisk heterocyklus med 1 til 4 N-, O- og/eller S-atomer, A betegner uforgrenet eller forgrenet alkyl med 1-10 C-atomer, hvor 1-7 H-atomer kan erstattes med OH, F, Cl og/eller Br, Hal betegner F, Cl, Br eller I, og farmaceutisk anvendelige salte og stereoisomerer deraf, herunder blandinger deraf i alle forhold.
7. Forbindelser ifølge krav 1, valgt fra gruppen 2-chlor-4-hydroxy-5-(2-methoxyphenyl)-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(2-hydroxyphenyl)-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(2-benzyloxyphenyl)-3-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-5-(4-methoxyphenyl)-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(4-hydroxyphenyl)-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(4-(aminohydroxyiminomethyl)phenyl)-3-phenyl-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-5-(4-methylsulfonylphenyl)-3-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 4-(2-chlor-4-hydroxy-3-phenyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-5- yl)benzoesyre, 2-chlor-4-hydroxy-5-(4-trifluormethylphenyl)-3-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 4-(2-chlor-4-hydroxy-5-phenyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-3- yl)benzamid, N-methyl-4-(2-chlor-4-hydroxy-5-phenyl-6-oxo-6,7-dihydro-thieno[2,3- b]pyridin-3-yl)benzamid, 2-chlor-4-hydroxy-5-(3-methoxyphenyl)-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(3-hydrophenyl)-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(3-cyanophenyl)-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(3-(aminohydroxyiminomethyl)phenyl)-3-phenyl-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2- chlor-4-hydroxy-5-(3-methylsulfonylphenyl)-3-phenyl-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 3- (2-chlor-4-hydroxy-5-phenyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-3-yl)benzoesyre, 2-chlor-4-hydroxy-5-(3-trifluormethylphenyl)-3-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-5-(3-aminoiminomethylphenyl)-3-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on-hydrochlorid, N-methyl-3-(2-chlor-4-hydroxy-5-phenyl-6-oxo-6,7-dihydro-thieno[2,3- b]pyridin-3-yl)benzamid, 2-chlor-3-(4-fluorphenyl)-4-hydroxy-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(4-methoxyphenyl)-5-phenyl-6,7-dihydrc>-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(4-hydroxyphenyl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(naphth-2-yl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(l-hyd roxy-naphth-2-yl)-5-phenyl-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(4-methylphenyl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(4-n-butylphenyl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(4-tert-butylphenyl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(4-hydroxyphenyl)-5-(4-fluorphenyl)-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2- chlor-4-hydroxy-3-(4-fluorphenyl)-5-(3-cyanophenyl)-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 3- (2-chlor-4-hydroxy-3-(4-fluorphenyl)-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-5-yl)benzoesyre, 2-chlor-4-hydroxy-3-(4-methoxyphenyl)-5-(3-cyanophenyl)-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(3-methoxyphenyl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(3-ethoxyphenyl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-3-(3-flurophenyl)-4-hydroxy-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(3-methylphenyl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on 2- chlor-4-hydroxy-3-(3-hydroxymethylphenyl)-5-phenyl-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 3- (2-chlor-4-hydroxy-5-phenyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-3-yl)benzoesyre, 2-chlor-4-hydroxy-3-(2-methoxyphenyl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-hydroxyphenyl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-benzyloxyphenyl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(2-fluorphenyl)-4-hydroxy-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-3-(2-chlorphenyl)-4-hydroxy-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-methylphenyl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-3-(2-fluor-4-hydroxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(2-fluor-4-methoxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2- chlor-3-(2,4-difluorphenyl)-4-hydroxy-5-phenyl-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 3- (2-benzyloxy-4-fluorphenyl)-2-chlor-4-hydroxy-5-phenyl-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-hydroxy-4-fluorphenyl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(3-fluor-4-methoxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(3-fluor-4-hydroxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2- chlor-3-(5-fluor-2-hydroxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 3- (2-benzyloxy-5-fluorphenyl)-2-chlor-4-hydroxy-5-phenyl-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3-(2,6-diflurophenyl)-4-hydroxy-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-methoxy-4-methylphenyl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-hydroxy-4-methylphenyl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(3-methoxy-4-methylphenyl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(3-hydroxy-4-methylphenyl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-hydroxy-4-methylphenyl)-5-(3-cyanophenyl)-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3-(3,4-difluorphenyl)-4-hydroxy-5-phenyl-6,7-dihydrc>-thieno[2,3- b]pyridin-6-on, 4-(2-chlor-4-hydroxy-5-phenyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-3- yl)benzoesyre, 2-chlor-3-(furan-2-yl)-4-hydroxy-5-phenyl-6,7-dihydrc>-thieno[2,3- b)pyridin-6-on, 2-chlor-4-hydroxy-5-phenyl-3-(pyridin-3-yl)-6,7-dihydrc>-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-phenyl-3-(pyridin-4-yl)-6,7-dihydrc>-thieno[2,3- b]pyridin-6-on, 2-bromo-3,5-diphenyl-4-hydroxy- 6,7-dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3,5-diphenyl-4-hydroxy- 6,7-dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-5-(2-methylphenyl)-3-phenyl-6,7-dihydrc>-thieno[2,3- b]pyridin-6-on, 2-chlor-5-(2-fluorphenyl)-4-hydroxy-3-phenyl-6,7-dihydrc>-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-phenyl-5-(pyridin-3-yl)-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(6-methoxypyridin-3-yl)-3-phenyl-6,7-dihydrc>- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-phenyl-5-(thiophen-2-yl)-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-phenyl-5-(thiophen-3-yl)-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(3-methyloxazol-5-yl)-3-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-5-(4-trifluormethylphenyl)-4-hydroxy-3-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-5-(4-fluorphenyl)-4-hydroxy-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-5-(4-chlorphenyl)-4-hydroxy-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(4-methylphenyl)-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-5-(3-fluorphenyl)-4-hydroxy-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(3-methylphenyl)-3-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-5-(3,4-dimethoxyphenyl)-3-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(4-chlorphenyl)-4-hydroxy-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(napht-l-yl)-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-3-(4-ethylphenyl)-4-hydroxy-5-phenyl-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-[4-(l-methylethyl)phenyl]-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-5-phenyl-3-(4-propylphenyl)-6,7-dihydro-thieno[2,3- b]pyridin-6-on, 2-chlor-4-hydroxy-3-(l-hydroxy-5-chlornapht-2-yl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-5-(4-fluorphenyl)-4-hydroxy-3-(l-hydroxynapht-2-yl)-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(l-hydroxynapht-2-yl)-5-(4-methylphenyl)-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3-(4-fluor-2-methoxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(5-fluor-2-methoxyphenyl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2- chlor-4-hydroxy-3-(3,4-dimethoxyphenyl)-5-phenyl-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 3- [2-chlor-4-hydroxy-3-(2-hydroxy-4-methylphenyl)-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-5-yl]-benzoesyre, 2-chlor-3-(4,5-difluor-2-hydroxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-hydroxy-4-methylphenyl)-5-(4-methylphenyl)-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-hydroxy-4-methylphenyl)-5-(pyridin-3-yl)-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(3,4-dimethylphenyl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(3-fluor-4-methyl-2-methoxyphenyl)-4-hydroxy-5-phenyl-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-methoxy-3,4-dimethylphenyl)-5-phenyl-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-hydroxy-3,4-dimethylphenyl)-5-phenyl-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3-(4-fluorphenyl)-5-(4-fluorphenyl)-4-hydroxy-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(3-fluor-2-hydroxy-4-methylphenyl)-5-(4-fluorphenyl)-4- hydroxy-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-hydroxy-4,5-dimethylphenylphenyl)-5-phenyl-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3-(3,4-difluor-2-hydroxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(4-ethyl-2-hydroxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(3-fluor-2-hydroxy-4-methylphenyl)-4-hydroxy-5-phenyl-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-fluor-3-(3-fluor-2-hydroxy-4-methylphenyl)-5-(4-fluorphenyl)-4- hydroxy-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3-(4-fluor-2-hydroxyphenyl)-4-hydroxy-5-(4-methoxyphenyl)-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3-(4-fluor-2-hydroxyphenyl)-5-(4-fluorphenyl)-4-hydroxy-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3-(4-fluor-2-hydroxyphenyl)-4-hydroxy-5-(4-methylphenyl)-6,7- dihydro-thieno[2,3-b]pyridin-6-on, og farmaceutisk anvendelige salte og stereoisomerer deraf, herunder blandinger deraf i alle forhold. I. Forbindelser ifølge krav 1 valgt fra gruppen 2-chlor-4-hydroxy-3-(3-hydroxy-4-methylphenyl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(3-hydroxy-4-methylphenyl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(3-methoxy-4-methylphenyl)-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(5-fluor-2-hydroxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(4-fluorphenyl)-5-(3-cyanophenyl)-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(l-hyd roxy-naphth-2-yl)-5-phenyl-6,7-dihydro-thieno[2,3-b]pyridin-6-on, N-methyl-3-(2-chlor-4-hydroxy-5-phenyl-6-oxo-6,7-dihydro-thieno[2,3- b]pyridin-3-yl)benzamid, 2-chlor-3-(4,5-difluor-2-hydroxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-hydroxy-3,4-dimethylphenyl)-5-phenyl-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3-(3-fluor-2-hydroxy-4-methylphenyl)-5-(4-fluorphenyl)-4- hydroxy-6,7-dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-4-hydroxy-3-(2-hydroxy-4,5-dimethylphenylphenyl)-5-phenyl-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3-(3,4-difluor-2-hydroxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(4-ethyl-2-hydroxyphenyl)-4-hydroxy-5-phenyl-6,7-dihydro- thieno[2,3-b]pyridin-6-on, 2-chlor-3-(3-fluor-2-hydroxy-4-methylphenyl)-4-hydroxy-5-phenyl-6,7- dihydro-thieno[2,3-b]pyridin-6-on, 2-chlor-3-(4-fluor-2-hydroxyphenyl)-4-hydroxy-5-(4-methoxyphenyl)-6,7- dihydro-thieno[2,3-b]pyridin-6-on, og farmaceutisk anvendelige salte og stereoisomerer deraf, herunder blandinger deraf i alle forhold.
9. Fremgangsmåde til fremstillingen af forbindelser med formlen (I) ifølge kravene 1-8 og farmaceutisk anvendelige salte og stereoisomerer deraf, kendetegnet ved at en forbindelse med formlen (II)
(II) hvor R1, R2, R3 har betydningen indikeret i krav 1, og ALK betegner C1-C6 a I kyl cykliseres under basiske betingelser, og/eller en base eller syre med formlen I omdannes til et af dens salte.
10. Medikamenter omfattende mindst en forbindelse med formel (I) ifølge krav 1, og/eller farmaceutisk anvendelige salte og stereoisomerer deraf, herunder blandinger deraf i alle forhold, og eventuelt excipienser og/eller adjuvanser.
11. Anvendelse af forbindelser ifølge krav 1-8, og farmaceutisk anvendelige salte og stereoisomerer deraf, herunder blandinger deraf i alle forhold, til fremstillingen af et medikament til behandlingen af metabolisk syndrom, diabetes, fedme, cancer, inflammation, kardiovaskulære sygdomme.
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