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DK2311825T3 - Pyrimidinaminer som angiogenesemodulatorer - Google Patents

Pyrimidinaminer som angiogenesemodulatorer Download PDF

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Publication number
DK2311825T3
DK2311825T3 DK09159138.8T DK09159138T DK2311825T3 DK 2311825 T3 DK2311825 T3 DK 2311825T3 DK 09159138 T DK09159138 T DK 09159138T DK 2311825 T3 DK2311825 T3 DK 2311825T3
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methyl
amino
indazol
pyrimidinyl
hydrogen
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Amogh Boloor
Mui Cheung
Ronda Davis
Philip Anthony Harris
Kevin Hinkle
Robert Anthony Mook Jr
Jeffery Alan Stafford
James Martin Veal
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Novartis Ag
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    • 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
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/30—Halogen atoms or nitro radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/10—Ophthalmic agents for accommodation disorders, e.g. myopia
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
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  • Ophthalmology & Optometry (AREA)
  • Heart & Thoracic Surgery (AREA)
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  • Diabetes (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Claims (22)

  1. -1- PYRIMIDIN AMINER SOM ANGIOGENE SEMODUL ATORER YTENTKRAV Forbindelse med formlen (I):
    w eller et salt eller solvat deraf: hvor: D er
    r i eller
    / Xi er hydrogen, Ci-C4-alkyl; X2 er hydrogen, Ci-C4-alkyl; X3 er hydrogen eller halogen; X4 er hydrogen, Ci-C4-alkyl, cyanoalkyl, eller -(CH2)pC=C(CH2)tH; p er 1, 2 eller 3; t er 0 eller 1; W er CH; Qi er hydrogen, halogen, Ci_2-haloalkyl, Ci-C2-alkyl, Ci-C2-alkoxy, eller Ci-C2-haloalkoxy; Q2 er A1 eller A2; Q3 er A1, når Q2 er A2, og Q3 er A2, når Q2 er A1; hvor Q2 er A2 og Q3 er A1, hvor A1 er hydrogen, halogen, eller Ci-C3-haloalkyl og A2 er gruppen :fineret af -(Z)m-(Z1)-(Z2), hvor Z er CH2 og m er 0, 1,2 eller 3, eller Z er NR2 og m er 0 eller 1, eller Z er -2- CH2NR2 og m er O eller 1; Z1 er S(0)2, S(O) eller C(O); og Z2 er Ci-C4-alkyl eller NR3R4 og hvor R2, R3 og R4 hver uafhængigt er udvalgt fra H eller Cj-C4-alkyl; eller Q2 er A1 og Q3 er A2, hvor A1 er hydrogen, halogen, eller Ci-C3-alkyl og A2 er gruppen defineret af -(ZJm-iZ'HZ2), hvor Z er CH2 og m er 0, 1,2 eller 3, eller Z er NR2 og m er 0 eller 1, eller Z er CH2NR2 og m er 0 eller 1; Z1 er S(0)2, S(O), eller C(O); og Z2 er Ci-C4-alkyl eller NR3R4, og hvor R2, R3, og R4 hver uafhængigt er udvalgt fra H eller Ci-C4-alkyl.
  2. 2. Forbindelse ifølge krav 1, hvor D er
  3. 3. Forbindelse ifølge krav 2, hvor D er
  4. 4. Forbindelse ifølge krav 2, hvor D er
  5. 5. Forbindelse ifølge kravene 1-4, hvor X| er methyl eller ethyl.
  6. 6. Forbindelse ifølge krav 5, hvor X3 er methyl.
  7. 7. Forbindelse ifølge kravene 1-6, hvor X2 er hydrogen eller methyl.
  8. 8. Forbindelse ifølge krav 7, hvor X2 er methyl.
  9. 9. Forbindelse ifølge kravene 1-8, hvor X3 er hydrogen.
  10. 10. Forbindelse ifølge kravene 1-9, hvor X4 er hydrogen, methyl, ethyl, isopropyl, cyanmethyl eller ch2c=ch.
  11. 11. Forbindelse ifølge krav 10, hvor X4 er methyl.
  12. 12. Forbindelse ifølge krav 1, hvor D er:
    og Xj er methyl, X2 er methyl, X3 er hydrogen og X4 er methyl. -3-
  13. 13. Forbindelse ifølge krav 1-12, hvor Qj er H, Cl, methyl eller methoxy.
  14. 14. Forbindelse ifølge krav 1-13, hvor Q2 er A1, og Q3 er A2, hvor A1 er H, methyl eller chlor og A2 er gruppen defineret af -(Z)m - (Z*)-(Z2), hvor Z er CII2, og m er 0, 1, 2 eller 3; Z1 er S(0)2 og Z2 er Ci^-alkyl eller NR3R4 hvor R3 og R4 hver er udvalgt fra H eller CM-alkyl.
  15. 15. Forbindelse ifølge krav 1, hvor D er:
    og Xi er methyl; X2 er methyl; X3 er hydrogen; og X4 er methyl; W er C-H; Qi er hydrogen, chlorin, methyl eller methoxy; Q2 er A1 og Q3 er A2, hvor A1 er hydrogen, methyl, eller chlorin og A2 er gruppen defineret af -(Z)m-(Z1)-(Z2), hvor Z er CIF og m er 0, 1,2 eller 3, eller Z er NR2, og m er 0 eller 1, eller Z er CH2NR2 og m er 0 eller 1; Z1 er S(0)2, S(O), eller C(O); og Z2 er CrC4-alkyl eller NR3R4, og hvor R2, R3 og R4 hver uafhængigt er udvalgt fra hydrogen eller Ci-C4-alkyl.
  16. 16. Forbindelse ifølge krav 1 udvalgt fra gruppen bestående af: 1 3 -({4-[methyl(3 -methyl-1 H-indazol-6-yl)amino]-2-pyrimidinyl} amino)benzensulfonamid; N2-[5-(ethylsulfonyl)-2-methoxyphenyl]-N4-methyl-N4-(3-methyl-lH-indazol-6-yl)-2,4-pyrimidindiamin; N4-methyl-N4-(3-methyl-lH-indazol-6-yl)-N2-{3-[(methylsulfonyl)methyl]phenyl}-2,4- pyrimidindiamin; N-isopropyl-3 -({4-[methyl(3 -methyl-1 II-indazol-6-yl)amino]-2-pyrimidinyl} amino)benzensulfonamid; N4-ethyl-N2-[5 - (ethylsulfonyl) -2-methoxyphenyl] -N4-(3 -methyl-1 Fl-indazol-6-yl)-2,4-pyrimidindiamin; N-[3 -({4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl}amino)phenyl]methansulfonamid; N2-{3-[(isopropylsulfonyl)methyl]phenyl}-N4-methyl-N4-(3-methyl-lH-indazol-6-yl)-2,4- pyrimidindiamin; N2-{4-[(isopropylsulfonyl)methyl]phenyl}-N4-methyl-N4-(3-methyl-lH-indazol-6-yl)-2,4- pyrimidindiamin; N2-[5-(isobutylsulfonyl)-2-methoxyphenyl]-N4-(3-methyl-lH-indazol-6-yl)-2,4-pyrimidindiamin; N-[3 -({4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)phenyl] acetamid; N-[3 -({4-[ethyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)phenyl] acetamid; 4-methoxy-3 -((4-[(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)benzensulfonamid; N2-[5-(isopropylsulfonyl)-2-methoxyphenyl]-N4-methyl-N4-(3-methyl-lH-indazol-6-yl)-2,4- pyrimidindiamin; -4- N2-[5-(ethylsulfonyl)-2-methoxyphenyl]-N4-isopropyl-N4-(3-methyl-lH-indazol-6-yl)-2,4- pyrimidindiamin; N4-(lH-indazol-6-yl)-N4-methyl-N2-{3-[(methylsulfonyl)methyl]phenyl}-2,4-pyrimidindiamin; N4-(l,3-dimethyl-lH-indazol-6-yl)-N4-methyl-N2-{3-[(methylsulfonyl)methyl]phenyl}-2,4- pyrimidindiamin; N4-(2,3-dimethyl-2H-indazol-6-yl)-N4-methyl-N2-{3-[(methylsulfonyl)methyl]phenyl}-2,4- pyrimidindiamin; N4-(2,3-dimethyl-2H-indazol-6-yl)-N2-[5-(ethylsulfonyl)-2-methoxyphenyl]-N4-methyl-2,4- pyrimidindiamin; l-[4-methoxy-3-( {4-[(3-methyl-lH-mdazol-6-yl)amino]-2-pyrimidinyl} amino)phenyl]-1 -propanon; 4-methoxy-N-methyl-3-({4-[(3-methyl-lH-indazol-6-yl)amino]-2-pyrinridinyl} amino)benzensulfonamid; [(3-methyl-lH-indazol-6-yl)(2-{4-[(methylsulfonyl)methyl]anilino}-4-pyrimidinyl)amino] acetonitril; [{2-[5-(ethylsulfonyl)-2-methoxyanilino]-4-pyrimidinyl}(3-methyl-lH-indazol-6-yl)amino] acetonitril; [(3 -methyl-1 H-indazol-6-yl)(2- {3 -[(methylsulfonyl)methyl] anilino} -4-pyrimidinyl)amino] acetonitril; 4-methoxy-N-methyl-3 -({4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)benzensulfonamid; 4-( {4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)benzamid; 3-methoxy-4-( {4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)benzensulfonamid; N4-ethynyl-N4-(3-methyl-lH-indazol-6-yl)-N2-{3-[(methylsulfonyl)methyl]phenyl}-2,4- pyrimidindiamin; 3- ( {4-[( 3-methyl-1 H-indazol-6-yl)(2-propynyl)amino] -2-pyrimidinyl} amino)benzensulfonamid; 4- ( (4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)benzensulfonamid; N4-methyl-N4-(3-methyl-lH-indazol-6-yl)-N2-[3-(methylsulfonyl)phenyl]-2,4-pyrimidindiamin; 4-methoxy-3 -({4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2- pyrimidinyl} amino)benzensulfonamid; N2-[5-(ethylsulfonyl)-2-methoxyphenyl]-N4-(3-methyl-lH-indazol-6-yl)-2,4-pyrimidindiamin; 3-( {4-[methyl(3-methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)benzamid; N2-[4-(ethylsulfonyl)phenyl] -N4-methyl-N4-(3 -methyl-1 H-indazol-6-yl)-2,4-pyrimidindiamin; N-[4-( {4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino) benzyljethansulfonamid; -5- N-[3 -({4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinly} amino)benzyl] methansulfonamid; 2-chlor-5-({4-[methyl(3-methyl-lH-indazol-6-yl)amino]-2-pyrimidinyl}amino)benzensulfonamid; 2- chlor-4-( {4-ethyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)benzensulfonamid; 4-chlor-3 -({4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)benzensulfonamid; 3- methyl-4-( {4-ethyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)benzensul fonamid; 2- methyl-5-( {4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)benzensulfonamid; 4- methyl-3 -({4-[methyl(3 -methyl-1 H-indazol-6-yl)amino] -2-pyrimidinyl} amino)benzensulfonamid; N4-methyl-N4-(3-methyl-lH-indazol-6-yl)-N2-[3-(methylsulfinyl)phenyl]-2,4-pyrimidindiamin; N2-[2-fluor-5-(methylsulfonyl)phenyl]-N4-methyl-N4-(3-methyl-lH-indazol-6-yl)-2,4- pyrimidindiamin; N2-[2-mcthoxy-5-( methyl sul fonyl)phcnyl]-N4-methyl-N4-(3-mcthyl-lH-indazol-6-yl)-2,4- pyrimidindiamin; 3- ({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]pyrimidin-2-yl}amino)benzensulfonamid; 2- [4-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]pyrimidin-2-yl} amino)phenyl] ethansulfonamid; N4-(2,3-dimethyl-2H-indazol-6-yl)-N4-methyl-N2-{4-[(methylsulfonyl)methyl]phenyl}pyrimidin- 2,4-diamin; 3- ({4-[(l,2-dimethyl-lH-benzimidazol-5-yl)(mcthyl)amino]pyrimidin-2-yl} amino)benzensul fonamid; 3-({4-[(2-ethyl-3-mcthyl-2H-indazol-6-yl)(methyl)amino]pyrimidin-2- yl}amino)benzensulfonamid; eller et salt eller solvat deraf.
  17. 17. Farmaceutisk sammensætning, der omfatter en terapeutisk effektiv mængde af en forbindelse ifølge en hvilken som helst af kravene 1 til 16, eller et salt eller solvat deraf og en/et eller flere farmaceutisk acceptable bærere, fortyndingsmidler og excipienser.
  18. 18. Forbindelse ifølge en hvilken som helst af kravene 1 til 16 eller et salt eller solvat deraf til anvendelse i terapi.
  19. 19. Anvendelse af en forbindelse ifølge et hvilket som helst af kravene 1-16 eller et salt eller solvat deraf i fremstillingen af et medikament til anvendelse i behandlingen af en sygdom medieret af upassende VEGFR2 -aktivitet.
  20. 20. Anvendelse af en forbindelse ifølge en hvilken som helst af kravene 1 til 16 eller et salt eller solvat deraf, i fremstillingen af et medikament til anvendelse i behandlingen af en sygdom kendetegnet ved upassende angiogenese. -6-
  21. 21. Forbindelse ifølge en hvilken som helst af kravene 1 til 16 eller et salt eller solvat deraf til anvendelse i behandlingen af en sygdom medieret af upassende VEGFR2-aktivitet.
  22. 22. Forbindelse ifølge en hvilken som helst af kravene 1 til 16 eller et salt eller solvat deraf til anvendelse i behandlingen af en sygdom kendetegnet ved upassende angiogenese.
DK09159138.8T 2000-12-21 2001-12-19 Pyrimidinaminer som angiogenesemodulatorer DK2311825T3 (da)

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US25752600P 2000-12-21 2000-12-21
US26240301P 2001-01-16 2001-01-16
EP01994315A EP1343782B1 (en) 2000-12-21 2001-12-19 Pyrimidineamines as angiogenesis modulators

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