DK2690101T3 - 5-anilinoimidazopyridiner og fremgangsmåder til anvendelse - Google Patents

5-anilinoimidazopyridiner og fremgangsmåder til anvendelse Download PDF

Info

Publication number
DK2690101T3
DK2690101T3 DK13155995.7T DK13155995T DK2690101T3 DK 2690101 T3 DK2690101 T3 DK 2690101T3 DK 13155995 T DK13155995 T DK 13155995T DK 2690101 T3 DK2690101 T3 DK 2690101T3
Authority
DK
Denmark
Prior art keywords
alkyl
cr14r15
cr19r20
fluoro
imidazo
Prior art date
Application number
DK13155995.7T
Other languages
English (en)
Inventor
Stephen Price
Robert Heald
Wendy Lee
Mark E Zak
Joanne Frances Mary Hewitt
Original Assignee
Genentech Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Genentech Inc filed Critical Genentech Inc
Application granted granted Critical
Publication of DK2690101T3 publication Critical patent/DK2690101T3/da

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • 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
    • 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
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (12)

1. Forbindelse til anvendelse i en fremgangsmåde til behandling af kræft, som er udvalgt fra: 5-(2-fluor-4-iodophenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre (2- hydroxyethoxy)-amid; 5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre ((R)-2,3-dihydroxy-propoxy)-amid; 5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre ((S)-2-hydroxy-propoxy)-amid; 5-(4-bromo-2-fluorphenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre (2- hydroxyethoxy)-amid; 5-(4-bromo-2-fluor-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre ((S)-2-hydroxy-propoxy)-amid; 5-(4-bromo-2-fluor-phenylamino)-8-fluor-imidazo[1,5-a]pyridin-6-carboxylsyre ((S)-2-hydroxy-propoxy)-amid; 8-fluor-5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre (2-hydroxy-ethoxy)-amid; 8-fluor-5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre ((R)-2,3-dihydroxy-propoxy)-amid; 8-fluor-5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre ((S)-2-hydroxy-propoxy)-amid; 5-(2-fluor-methansulfanyl-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre (2-hydroxy-ethoxy)-amid; 5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyrazin-6-carboxylsyre (2-hydroxy-ethoxy)-amid; 5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyrazin-6-carboxylsyre ((S)-2-hydroxy-propoxy)-amid; 5- (4-cyclopropyl-2-fluor-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre (2-hydroxy-ethoxy)-amid; (R)-/V-(2,3-dihydroxypropoxy)-5-(2-fluor-4-iodophenylamino)imidazo[1,5-a]pyrazin-6-carboxamid; A/-ethoxy-5-(2-fluor-4-iodophenylamino)imidazo[1,5-a]pyrazin-6-carboxamid; A/-(cyclopropylmethoxy)-5-(2-fluor-4-iodophenylamino)imidazo[1,5-a]pyrazin- 6- carboxamid; 5-(2-fluor-4-iodophenylamino)-A/-methylimidazo[1,5-a]pyrazin-6-carboxamid; 5- (4-bromo-2-fluorphenylamino)-A/-(2-hydroxy-ethoxy)imidazo[1,5-a]pyrazin- 6- carboxamid; (S)-5-(4-bromo-2-fluorphenylamino)-A/-(2-hydroxy-propoxy)imidazo[1,5-a]pyrazin-6-carboxamid; (R)-5-(4-bromo-2-fluorphenylamino)-A/-(2,3-dihydroxy-propoxy)imidazo[1,5-a]pyrazin-6-carboxamid; og 5-(4-bromo-2-fluorphenylamino)-/V-(cyclopropyl-methoxy)imidazo[1,5-a]pyrazin-6-carboxamid; eller et farmaceutisk acceptabelt salt deraf; hvilken fremgangsmåde omfatter indgivelse af forbindelsen i kombination med gemcitabin eller et taxoid.
2. Forbindelse til anvendelse i en fremgangsmåde til behandling af kræft ifølge krav 1, hvor forbindelsen er 5-(2-fluor-4-iodophenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre (2-hydroxyethoxy)-amid eller et farmaceutisk acceptabelt salt deraf.
3. Forbindelse til anvendelse i en fremgangsmåde til behandling af kræft ifølge krav 1 eller krav 2, hvor kræften er bugspytkirtelkræft, ikke-småcellet lungekræft, kolorektal kræft, endometriekræft, æggestokkræft eller malignt melanom.
4. Forbindelse til anvendelse i en fremgangsmåde til behandling af kræft ifølge et af kravene 1 til 3, hvor forbindelsen indgives samtidigt med taxoidet eller gemcitabinet.
5. Forbindelse til anvendelse i en fremgangsmåde til behandling af kræft ifølge et af kravene 1 til 3, hvor forbindelsen indgives sekventielt med taxoidet eller gemcitabinet.
6. Forbindelse til anvendelse i en fremgangsmåde til behandling af kræft ifølge et af kravene 1 til 3, hvor forbindelsen indgives adskilt fra taxoidet eller gemcitabinet.
7. Forbindelse til anvendelse i en fremgangsmåde til behandling af kræft ifølge et af de foregående krav, hvor taxoidet er paclitaxel.
8. Forbindelse til anvendelse i en fremgangsmåde til behandling af kræft ifølge et af de foregående krav, hvor behandlingen er til oral indgivelse.
9. Forbindelse til anvendelse i en fremgangsmåde til behandling af kræft ifølge et af kravene 1 til 3, hvor forbindelsen er til indgivelse i kombination med gemcitabin til behandling af bugspytkirtelkræft.
10. Forbindelse til anvendelse i en fremgangsmåde til behandling af kræft ifølge et af kravene 1 til 3, hvor forbindelsen er til indgivelse i kombination med paclitaxel til behandling af ikke-småcellet lungekræft eller æggestokkræft.
11. Forbindelse til anvendelse i en fremgangsmåde til behandling af kræft eller en inflammatorisk lidelse kendetegnet ved mutation eller overekspression af MEK-kinase, hvor forbindelsen er udvalgt fra: 5-(2-fluor-4-iodophenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre (2- hydroxyethoxy)-amid; 5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre ((R)-2,3-dihydroxy-propoxy)-amid; 5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre ((S)-2-hydroxy-propoxy)-amid; 5-(4-bromo-2-fluorphenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre (2- hydroxyethoxy)-amid; 5-(4-bromo-2-fluor-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre ((S)-2-hydroxy-propoxy)-amid; 5-(4-bromo-2-fluor-phenylamino)-8-fluor-imidazo[1,5-a]pyridin-6-carboxylsyre ((S)-2-hydroxy-propoxy)-amid; 8-fluor-5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre (2-hydroxy-ethoxy)-amid; 8-fluor-5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre ((R)-2,3-dihydroxy-propoxy)-amid; 8-fluor-5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre ((S)-2-hydroxy-propoxy)-amid; 5-(2-fluor-methansulfanyl-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre (2-hydroxy-ethoxy)-amid; 5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyrazin-6-carboxylsyre (2-hydroxy-ethoxy)-amid; 5-(2-fluor-4-iodo-phenylamino)-imidazo[1,5-a]pyrazin-6-carboxylsyre ((S)-2-hydroxy-propoxy)-amid; 5- (4-cyclopropyl-2-fluor-phenylamino)-imidazo[1,5-a]pyridin-6-carboxylsyre (2-hydroxy-ethoxy)-amid; (R) -A/-(2,3-dihydroxypropoxy)-5-(2-fluor-4-iodophenylamino)imidazo[1,5-a]pyrazin-6-carboxamid; A/-ethoxy-5-(2-fluor-4-iodophenylamino)imidazo[1,5-a]pyrazin-6-carboxamid; A/-(cyclopropylmethoxy)-5-(2-fluor-4-iodophenylamino)imidazo[1,5-a]pyrazin- 6- carboxamid; 5-(2-fluor-4-iodophenylamino)-A/-methylimidazo[1,5-a]pyrazin-6-carboxamid; 5- (4-bromo-2-fluorphenylamino)-A/-(2-hydroxy-ethoxy)imidazo[1,5-a]pyrazin- 6- carboxamid; (S) -5-(4-bromo-2-fluorphenylamino)-A/-(2-hydroxy-propoxy)imidazo[1,5-a]pyrazin-6-carboxamid; (R)-5-(4-bromo-2-fluorphenylamino)-A/-(2,3-dihydroxy-propoxy)imidazo[1,5-a]pyrazin-6-carboxamid; og 5-(4-brom-2-fluorphenylamino)-A/-(cyclopropyl-methoxy)imidazo[1,5-a]pyrazin-6-carboxamid; eller et farmaceutisk acceptabelt salt deraf.
12. Forbindelse repræsenteret ved formel 1 og salte deraf til anvendelse i en fremgangsmåde til behandling af en inflammatorisk lidelse:
hvor: Z1 erCR1 eller N; R1 er H, CrC3 alkyl, halogen, CF3, CHF2, CN, ORA eller NRARA; R1 er H, CrC3 alkyl, halogen, CF3, CHF2, CN, ORA eller NRARA; hvor hvert RA uafhængigt er H eller CrC3 alkyl; Z2 er CR2 eller N; Z3 er CR3 eller N; forudsat at kun et af Z1, Z2 og Z3 kan være N på samme tid; R2 og R3 uafhængigt er udvalgt fra H, halogen, CN, CF3, -OCF3, -N02, -(CR14R15)nC(=Y')R11, -(CR14R15)nC(=Y')OR11, -(CR14R15)nC(=Y')NR11R12, -(CR14R15)nNR11R12, -(CR14R15)nOR11, -(CR14R15)nSR11, -(CR14R15)nNR12C(=Y')R11 -(CR14R15)nNR12C(=Y')OR11, -(CR14R15)nNR13C(=Y')NR11R12, -(CR14R15)nNR12S02R11, -(CR14R15)nOC(=Y')R11, -(CR14R15)nOC(=Y')OR11, -(CR14R15)nOC(=Y')NR11 R12, -(CR14R15)n0S(0)2(0R11), -(CR14R15)nOP(=Y')(OR11)(OR12), -(CR14R15)nOP(OR11)(OR12), -(CR14R15)nS(0)R11, -(CR14R15)nS(0)2R11, -(CR14R15)n S(0)2NR11R12, -(CR14R15)nS(0)(0R11), -(CR14R15)nS(0)2(0R11), -(CR14R15)n SC(=Y')R11, -(CR14R15)nSC(=Y')OR11, -(CR14R15)nSC(=Y')NR11R12, Ci-Ci2 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, carbocyclyl, heterocyclyl, aryl og heteroaryl; R4 er H, CrC6 alkyl eller C3-C4 carbocyclyl; YerW-C(O)- eller W; Wer
R5 er H eller CrCi2 alkyl; X1 er udvalgt fra R11 og -OR11; hvor X1, når X1 er R11, eventuelt sammen med R5 og nitrogenatomet, som de er bundet til, danner en 4-7-leddet mættet eller umættet ring med 0-2 yderligere heteroatomer, udvalgt fra O, S og N, hvor ringen eventuelt er substitueret med en eller flere grupper, udvalgt fra halogen, CN, CF3, -OCF3, -N02, oxo, -(CR19R20)nC(=Y')R16, -(CR19R20)n C(=Y')OR16, -(CR19R20)nC(=Y)NR16R17, -(CR19R20)nNR16R17, -(CR19R20)nOR16, -(CR19R20)n-SR16, -(CR19R20)nNR16C(=Y')R17, -(CR19R20)n NR16C(=Y)OR17, -(CR19R20)n NR18C(=Y')NR16R17, -(CR19R20)nNR17SO2R16, -(CR19R20)nOC(=Y')R16, -(CR19R20)nOC(=Y')OR16, -(CR19R20)nOC(=Y')NR16R17, -(CR19R20)nOS(O)2(OR16), -(CR19R20)nOP(=Y')(OR16)(OR17), -(CR19R20)nOP(OR16)(OR17), -(CR19R20)nS(O)R16, -(CR19R21)nS(0)2R16, -(CR19R20)nS(O)2NR16R17, -(CR19R20)nS(O)(OR16), -(CR19R20)n S(0)2(0R16), -(CR19R20)n SC(=Y')R16, -(CR19R20)n SC(=Y')OR16, -(CR19R20)n SC(=Y')NR16R17 og R21; hvert R11 uafhængigt er H, C1-C12 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, carbo-cyclyl, heterocyclyl, aryl eller heteroaryl; R11, R12 og R13 uafhængigt er H, CrCi2 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, carbocyclyl, heterocyclyl, aryl eller heteroaryl, eller R11 og R12 sammen med nitrogenet, som de er bundet til, danner en 3-8-leddet mættet, umættet eller aromatisk ring med 0-2 heteroatomer udvalgt fra O, S og N, hvor ringen eventuelt er substitueret med en eller flere grupper udvalgt fra halogen, CN, CF3, -OCF3, -N02, CrC6 alkyl, -OH, -SH, -0(CrC6 alkyl), -S(CrC6 alkyl), -NH2, -NH(CrC6 alkyl), -N(CrC6 alkyl)2, -S02(CrC6 alkyl), -C02H, -C02(CrC6 alkyl), -C(0)NH2, -C(0)NH(CrC6 alkyl), -C(0)N(CrC6 alkyl)2, -N(CrC6 alkyl)C(0)(CrC6 alkyl), -NHC(0)(CrC6 alkyl), -NHSO(CrC6 alkyl), -N(CrC6 alkyl)S02(CrC6 alkyl), -S02NH2, -S02NH(Cr C6 alkyl), -SOsNiCrCe alkyl)2, -0C(0)NH2, -0C(0)NH(CrC6 alkyl), -0C(0)N(CrC6 alkyl)2, -0C(0)0(CrC6 alkyl), -NHC(0)NH(CrC6 alkyl), -NHC(0)N(CrC6 alkyl)2, -N(CrC6 alkyOCiOJNHiCrCe alkyl), -ISKCrCe alkyl)C(0)N(CrC6 alkyl)2, -NHC(0)NH(CrC6 alkyl), -mC(0)N(CA-C& alkyl)2, -NHC(0)0(CrC6 alkyl) og -N(CrC6 alkyl)C(0)0(CrC6 alkyl); R14 og R15 uafhængigt er udvalgt fra H, CrCi2 alkyl, aryl, carbocyclyl, heterocyclyl og heteroaryl;
hvert X2 uafhængigt er O, S eller NR9; hvert R7 uafhængigt er udvalgt fra H, halogen, CN, CF3, -OCF3, -N02, -(CR14R15)nC(=Y')R11, -(CR14R15)nC(=Y')OR11, -(CR14R15)nC(=Y')NR11R12, -(CR14R15)nNR11R12, -(CR14R15)nOR11, -(CR14R15)nSR11, -(CR14R15)nNR12C(=Y')R11, -(CR14R15)nNR12C(=Y')OR11, -(CR14R15)nNR13C(=Y')NR11R12, -(CR14R15)nNR12S02R11, -(CR14R15)nOC(=Y')R11, -(CR14R15)nOC(=Y')OR11, -(CR14R15)nOC(=Y')NR11 R12, -(CR14R15)n0S(0)2(0R11), -(CR14R15)nOP(=Y')(OR11)(OR12), -(CR14R15)nOP(OR11)(OR12), -(CR14R15)nS(0)R11,-(CR14R15)nS(0)2R11, -(CR14R15)nS(0)2NR11R12, -(CR14R15)nS(0)(0R11), -(CR14R15)nS(0)2(0R11), -(CR14R15)n SC(=Y')R11, -(CR14R15)nSC(=Y')OR11, -(CR14R15)nSC(=Y')NR11R12, CrCi2 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, carbocyclyl, heterocyclyl, aryl og heteroaryl; hvert R8 uafhængigt er udvalgt fra CrCi2 alkyl, aryl, carbocyclyl, heterocyclyl og heteroaryl; R9 er udvalgt fra H, -(CR14R15)nC(=Y')R11, -(CR14R15)nC(=Y')OR11, -(CR14R15)nC(=Y')NR11R12, -(CR14R15)qNR11R12, -(CR14R15)qOR11, -(CR14R15)qSR11, -(CR14R15)qNR12C(=Y')R11,-(CR14R15)qNR12C(=Y)OR11, -(CR14R15)qNR13C(=Y')NR11R12, -(CR14R15)qNR12S02R11, -(CR14R15)qOC(=Y')R11, -(CR14R15)qOC(=Y')OR11, -(CR14R15)qOC(=Y')NR11 R12, (CR14R15)q0S(0)2(0R11), -(CR14R15)qOP(- Y')(OR11)(OR12), -(CR14R15)qOP(OR11)(OR12), -(CR14R15)nS(0)R11, -(CR14R15)nS(0)2R11, -(CR14R15)n S(0)2NR11R12, CrC12 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, carbocyclyl, heterocyclyl, aryl og heteroaryl; R10 er H, CrC6 alkyl eller C3-C4 carbocyclyl;
R6 er H, halogen, CrC6 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, carbocyclyl, heteroaryl, heterocyclyl, -OCF3, -N02, -Si(CrC6 alkyl), -(CR19R20)nNR16R17, -(CR19R20)nOR16, eller -(CR19R20)n-SR16; R6 er H, halogen, CrC6 alkyl, carbocyclyl, CF3, -OCF3, -N02, -Si(CrC6 alkyl), -(CR19R20)nNR16R17, -(CR19R20)nOR16, -(CR19R20)n-SR16, C2-C8 alkenyl, C2-C8 alkynyl, heterocyclyl, aryl eller heteroaryl; p er 0,1,2 eller 3; n er 0,1,2 eller 3; q er 2 eller 3; hvor hvert alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl og heteroaryl af R1, R2, R3, R4, R5, R6, R6', R7, R8, R9, R10, R11, R11', R12, R13, R14, R15 og Ra uafhængigt eventuelt er substitueret med en eller flere grupper uafhængigt udvalgt fra halogen, CN, CF3, -OCF3, -NO2, oxo, -Si(CrC6 alkyl), -(CR19R20)nC(=Y')R16, -(CR19R20)n C(=Y')OR16, -(CR19R20)nC(=Y')NR16R17, -(CR19R20)nNR16R17, -(CR19R20)nOR16, -(CR19R20)nSR16, -(CR19R20)nNR16C(=Y')R17, -(CR19R20)nNR16C(=Y')OR17, -(CR19R20)nNR18C(=Y')NR16R17, -(CR19R20)nNR17SO2R16, -(CR19R20)nOC(=Y')R16, -(CR19R20)nOC(=Y')OR16, -(CR19R20)nOC(=Y')NR16R17, (CR19R20)nOS(O)2(OR16), -(CR19R20)nOP(=Y')(OR16)(OR17),-(CR19R20)nOP(OR16)(OR17), -(CR19R20)nS(O)R16,-(CR19R20)nS(O)2R16, -(CR19R20)nS(O)2NR16R17, -(CR19R20)nS(O)(OR16), -(CR19R20)n S(0)2(0R16), -(CR19R20)nSC(=Y')R16, -(CR19R20)nSC(=Y')OR16, -(CR19R20)n SC(=Y')NR16R17 og R21; hvert R16, R17 og R18 uafhængigt er H, CrCi2 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, carbocyclyl, heterocyclyl, aryl eller heteroaryl, hvor alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl eller heteroaryl eventuelt er substitueret med en eller flere grupper udvalgt fra halogen, CN, -OCF3, CF3, -N02, CrC6 alkyl, -OH, -SH, -0(CrC6 alkyl), -S(CrC6 alkyl), -NH2, -NH(CrC6 alkyl), -N(CrC6 alkyl)2, -S02(CrC6 alkyl), -C02H, -C02(CrC6 alkyl), -C(0)NH2, -C(0)NH(C-|-C6 alkyl), -C(0)N(CrC6 alkyl)2, -N(CrC6 alkyl)C(0)(CrC6 alkyl), -NHC(0)(CrC6 alkyl), -NHS02(CrC6 alkyl), -N(CrC6 alkyl)S02(CrC6 alkyl), -S02NH2, -S02NH(C-|-C6 alkyl), -S02N(CrC6 alkyl)2, -0C(0)NHz, -0C(0)NH(CrC6 alkyl), -0C(0)N(CrC6 alkyl)2, -0C(0)0(CrC6 alkyl), -NHC(0)NH(Ci-C6 alkyl), -NHC(0)N(CrC6 alkyl)2, -N(CrC6 al-kyl)C(0)NH(CrC6 alkyl), -N(CrC6 alkyl)C(0)N(CrC6 alkyl)2, -NHC(0)NH(Cr C6 alkyl), -NHC(0)N(CrC6 alkyl)2, -NHC(0)0(CrC6 alkyl) og -N(CrC6 al-kyl)C(0)0(CrC6 alkyl); eller R16 og R17 sammen med nitrogenet, som de er bundet til, danner en 3-8-leddet mættet, umættet eller aromatisk ring med 0-2 heteroatomer udvalgt fra O, S og N, hvor ringen eventuelt er substitueret med en eller flere grupper udvalgt fra halogen, CN, -OCF3, CF3, -N02, CrC6 alkyl, -OH, -SH, -0(CrC6 alkyl), -S(CrC6 alkyl), -NH2, -NH(CrC6 alkyl), -N(CrC6 alkyl)2, -S02(CrC6 alkyl), -C02H, -C02(CrC6 alkyl), -C(0)NH2, -C(0)NH(CrC6 alkyl), -C(0)N(CrC6 alkyl)2, -N(CrC6 alkyl)C(0)(CrC6 alkyl), -NHC(0)(CrC6 alkyl), -NHS02(Ci-C6 alkyl), -N(CrC6 alkyl)S02(CrC6 alkyl), -S02NH2, -S02NH(Cr C6 alkyl), -S02N(CrC6 alkyl)2, -0C(0)NH2, -0C(0)NH(CrC6 alkyl), -0C(0)N(Ci-C6 alkyl)2, -0C(0)0(Ci-C6 alkyl), -NHC(0)NH(Ci-C6 alkyl), -NHC(0)N(CrC6 alkyl)2, -N(CrC6 alkyl)C(0)NH(CrC6 alkyl), N(CrC6 al-kyl)C(0)N(CrC6 alkyl)2, -NHC(0)NH(CrC6 alkyl), -NHC(0)N(CrC6 alkyl)2, -NHC(0)0(CrC6 alkyl) og -N(CrC6 alkyl)C(0)0(CrC6 alkyl); R19 og R20 uafhængigt er udvalgt fra H, CrCi2 alkyl, -(CH2)n-aryl, -(CH2)n-carbocyclyl, -(CH2)n-heterocyclyl og -(CH2)n-heteroaryl; R21 er CrCi2 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, carbocyclyl, heterocyclyl, aryl eller heteroaryl, hvor hvert medlem af R21 eventuelt er substitueret med en eller flere grupper udvalgt fra halogen, oxo, CN, -OCF3, CF3, -N02, CrC6 alkyl, -OH, -SH, -0(CrC6 alkyl), -S(CrC6 alkyl), -NH2, -NH(CrC6 alkyl), -N(C-|-C6 alkyl)2, -S02(CrC6 alkyl), -C02H, -C02(CrC6 alkyl), -C(0)NH2, -C(0)NH(CrC6 alkyl), -C(0)N(CrC6 alkyl)2, -N(CrC6 alkyl)C(0)(CrC6 alkyl), -NHC(0)(C-|-C6 alkyl), -NHS02(CrC6 alkyl), -N(CrC6 alkyl)S02(CrC6 alkyl), -S02NH2, -S02NH(CrC6 alkyl), -S02N(CrC6 alkyl)2, -0C(0)NH2, -0C(0)NH(CrC6 alkyl), -0C(0)N(CrC6 alkyl)2, -0C(0)0(CrC6 alkyl), -NHC(0)NH(C-|-C6 alkyl), -NHC(0)N(CrC6 alkyl)2, -N(CrC6 alkyl)C(0)NH(CrC6 alkyl), -N(CrC6 alkyl)C(0)N(CrC6 alkyl)2, -NHC(0)NH(CrC6 alkyl), -NHC(0)N(CrC6 alkyl)2, -NHC(0)0(CrC6 alkyl) og -N(CrC6 alkyl)C(0)0(CrC6 alkyl); hvert Y' uafhængigt er O, NR22 eller S; og R22 er H eller CrCi2 alkyl.
DK13155995.7T 2007-12-19 2008-12-18 5-anilinoimidazopyridiner og fremgangsmåder til anvendelse DK2690101T3 (da)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US1512907P 2007-12-19 2007-12-19
US5401408P 2008-05-16 2008-05-16
EP08869100.1A EP2222675B1 (en) 2007-12-19 2008-12-18 5-anilinoimidazopyridines and methods of use

Publications (1)

Publication Number Publication Date
DK2690101T3 true DK2690101T3 (da) 2015-09-28

Family

ID=40350172

Family Applications (2)

Application Number Title Priority Date Filing Date
DK13155995.7T DK2690101T3 (da) 2007-12-19 2008-12-18 5-anilinoimidazopyridiner og fremgangsmåder til anvendelse
DK08869100.1T DK2222675T3 (da) 2007-12-19 2008-12-18 5-anilinoimidazopyridiner og fremgangsmåder til deres anvendelse

Family Applications After (1)

Application Number Title Priority Date Filing Date
DK08869100.1T DK2222675T3 (da) 2007-12-19 2008-12-18 5-anilinoimidazopyridiner og fremgangsmåder til deres anvendelse

Country Status (28)

Country Link
US (4) US7923456B2 (da)
EP (2) EP2690101B1 (da)
JP (1) JP5421925B2 (da)
KR (1) KR101195329B1 (da)
CN (1) CN101945870B (da)
AR (1) AR069803A1 (da)
AU (1) AU2008343065B2 (da)
BR (1) BRPI0819529A2 (da)
CA (1) CA2706571C (da)
CL (1) CL2008003810A1 (da)
CY (2) CY1114663T1 (da)
DK (2) DK2690101T3 (da)
ES (2) ES2437141T3 (da)
HK (2) HK1147254A1 (da)
HR (1) HRP20151002T1 (da)
HU (1) HUE025192T2 (da)
IL (1) IL205977A (da)
MX (1) MX2010006800A (da)
MY (1) MY158829A (da)
NZ (1) NZ586802A (da)
PE (2) PE20131210A1 (da)
PL (2) PL2222675T3 (da)
PT (2) PT2690101E (da)
RU (1) RU2441004C1 (da)
SI (2) SI2222675T1 (da)
TW (1) TWI441820B (da)
WO (1) WO2009085983A1 (da)
ZA (1) ZA201003625B (da)

Families Citing this family (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8242140B2 (en) 2007-08-03 2012-08-14 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
JP5623289B2 (ja) 2007-12-19 2014-11-12 ベーリンガーインゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング ウイルスポリメラーゼインヒビター
US8329705B2 (en) 2009-12-30 2012-12-11 Arqule, Inc. Substituted triazolo-pyrazine compounds
WO2011082271A2 (en) 2009-12-30 2011-07-07 Arqule, Inc. Substituted triazolo-pyrimidine compounds
CN102020651B (zh) 2010-11-02 2012-07-18 北京赛林泰医药技术有限公司 6-芳基氨基吡啶酮甲酰胺mek抑制剂
TW201840336A (zh) 2011-08-01 2018-11-16 美商建南德克公司 利用pd-1軸結合拮抗劑及mek抑制劑治療癌症之方法
WO2013082511A1 (en) 2011-12-02 2013-06-06 Genentech, Inc. Methods for overcoming tumor resistance to vegf antagonists
NZ702244A (en) 2012-06-08 2017-06-30 Hoffmann La Roche Mutant selectivity and combinations of a phosphoinositide 3 kinase inhibitor compound and chemotherapeutic agents for the treatment of cancer
CN105246508A (zh) 2013-03-14 2016-01-13 基因泰克公司 Mek抑制剂化合物与her3/egfr抑制剂化合物的组合及使用方法
US9532987B2 (en) 2013-09-05 2017-01-03 Genentech, Inc. Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases
GB201321729D0 (en) * 2013-12-09 2014-01-22 Ucb Pharma Sa Therapeutic agents
EP3094736A4 (en) 2014-01-14 2017-10-25 Dana-Farber Cancer Institute, Inc. Compositions and methods for identification, assessment, prevention, and treatment of melanoma using pd-l1 isoforms
JOP20200094A1 (ar) 2014-01-24 2017-06-16 Dana Farber Cancer Inst Inc جزيئات جسم مضاد لـ pd-1 واستخداماتها
JOP20200096A1 (ar) 2014-01-31 2017-06-16 Children’S Medical Center Corp جزيئات جسم مضاد لـ tim-3 واستخداماتها
EP3116909B1 (en) 2014-03-14 2019-11-13 Novartis Ag Antibody molecules to lag-3 and uses thereof
CN106573060A (zh) 2014-07-15 2017-04-19 豪夫迈·罗氏有限公司 使用pd‑1轴结合拮抗剂和mek抑制剂治疗癌症的组合物
CN108358939A (zh) * 2014-07-29 2018-08-03 上海科州药物研发有限公司 作为蛋白激酶抑制剂的杂环化合物及其制备方法和用途
EP3925622A1 (en) 2014-09-13 2021-12-22 Novartis AG Combination therapies
CA2963281A1 (en) 2014-10-03 2016-04-07 Novartis Ag Combination therapies
EP3204516B1 (en) 2014-10-06 2023-04-26 Dana-Farber Cancer Institute, Inc. Angiopoietin-2 biomarkers predictive of anti-immune checkpoint response
EP4245376A3 (en) 2014-10-14 2023-12-13 Novartis AG Antibody molecules to pd-l1 and uses thereof
EP3233918A1 (en) 2014-12-19 2017-10-25 Novartis AG Combination therapies
MA41338B1 (fr) * 2015-01-16 2019-07-31 Hoffmann La Roche Composés de pyrazine pour le traitement de maladies infectieuses
MA41866A (fr) 2015-03-31 2018-02-06 Massachusetts Gen Hospital Molécules à auto-assemblage pour l'administration ciblée de médicaments
EP3328418A1 (en) 2015-07-29 2018-06-06 Novartis AG Combination therapies comprising antibody molecules to pd-1
LT3317301T (lt) 2015-07-29 2021-07-26 Novartis Ag Kombinuotos terapijos, apimančios antikūno molekules prieš lag-3
US20180207273A1 (en) 2015-07-29 2018-07-26 Novartis Ag Combination therapies comprising antibody molecules to tim-3
WO2017033113A1 (en) 2015-08-21 2017-03-02 Acerta Pharma B.V. Therapeutic combinations of a mek inhibitor and a btk inhibitor
MA43186B1 (fr) 2015-11-03 2022-03-31 Janssen Biotech Inc Anticorps se liant spécifiquement à pd-1 et leurs utilisations
CN105399661A (zh) * 2015-12-14 2016-03-16 华东师范大学 2,6-二溴甲基吡啶的制备方法
MX2018007423A (es) 2015-12-17 2018-11-09 Novartis Ag Moleculas de anticuerpo que se unen a pd-1 y usos de las mismas.
AU2017249229A1 (en) 2016-04-15 2018-10-04 Genentech, Inc. Diagnostic and therapeutic methods for cancer
EP3458455B1 (en) 2016-05-20 2021-06-16 F. Hoffmann-La Roche AG Novel pyrazine compounds with oxygen, sulfur and nitrogen linker for the treatment of infectious diseases
CN109476659B (zh) 2016-07-14 2021-07-09 豪夫迈·罗氏有限公司 用于治疗感染性疾病的新的四氢吡唑并吡啶化合物
JP7051804B2 (ja) * 2016-07-14 2022-04-11 エフ．ホフマン－ラ ロシュ アーゲー 感染症の治療のための６，７－ジヒドロ－４Ｈ－ピラゾロ［１，５－ａ］ピラジン化合物と６，７－ジヒドロ－４Ｈ－トリアゾロ［１，５－ａ］ピラジン化合物
WO2018011162A1 (en) 2016-07-14 2018-01-18 F. Hoffmann-La Roche Ag Carboxy 6,7-dihydro-4h-pyrazolo[1,5-a]pyrazine compounds for the treatment of infectious diseases
WO2018011160A1 (en) * 2016-07-14 2018-01-18 F. Hoffmann-La Roche Ag 6,7-dihydro-4h-pyrazolo[1,5-a]pyrazine compounds for the treatment of infectious diseases
AU2017315572B2 (en) * 2016-08-23 2021-07-15 Beijing Innocare Pharma Tech Co., Ltd. Fused heterocyclic derivative, preparation method therefor and medical use thereof
AU2018329925A1 (en) 2017-09-08 2020-03-05 F. Hoffmann-La Roche Ag Diagnostic and therapeutic methods for cancer
MX2020004756A (es) 2017-11-16 2020-08-20 Novartis Ag Terapias de combinacion.
EP3752200A1 (en) 2018-02-13 2020-12-23 Vib Vzw Targeting minimal residual disease in cancer with rxr antagonists
SG11202011633SA (en) 2018-05-24 2020-12-30 Janssen Biotech Inc Psma binding agents and uses thereof
AR116109A1 (es) 2018-07-10 2021-03-31 Novartis Ag Derivados de 3-(5-amino-1-oxoisoindolin-2-il)piperidina-2,6-diona y usos de los mismos
WO2020106306A1 (en) * 2018-11-20 2020-05-28 Nflection Therapeutics, Inc. Cyanoaryl-aniline compounds for treatment of dermal disorders
KR20210106437A (ko) 2018-12-20 2021-08-30 노파르티스 아게 3-(1-옥소이소인돌린-2-일)피페리딘-2,6-디온 유도체를 포함하는 투약 요법 및 약학적 조합물
EP3924055B1 (en) 2019-02-15 2024-04-03 Novartis AG Substituted 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof
US20220144807A1 (en) 2019-02-15 2022-05-12 Novartis Ag 3-(1-oxo-5-(piperidin-4-yl)isoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof
AR118720A1 (es) 2019-04-19 2021-10-27 Janssen Biotech Inc Métodos para tratar el cáncer de próstata con un anticuerpo anti-psma / cd3
BR112021021652A2 (pt) * 2019-04-30 2021-12-21 Aicuris Gmbh & Co Kg Oxalil piperazinas inovadoras ativas contra o vírus da hepatite b (hbv)
WO2021123996A1 (en) 2019-12-20 2021-06-24 Novartis Ag Uses of anti-tgf-beta antibodies and checkpoint inhibitors for the treatment of proliferative diseases
CN115916199A (zh) 2020-06-23 2023-04-04 诺华股份有限公司 包含3-(1-氧代异吲哚啉-2-基)哌啶-2,6-二酮衍生物的给药方案
BR112023015097A2 (pt) 2021-01-28 2023-10-03 Janssen Biotech Inc Proteínas de ligação a psma e usos das mesmas
EP4288434A1 (en) 2021-02-02 2023-12-13 Les Laboratoires Servier Selective bcl-xl protac compounds and methods of use
JP2024511373A (ja) 2021-03-18 2024-03-13 ノバルティス アーゲー がんのためのバイオマーカーおよびその使用
TW202304979A (zh) 2021-04-07 2023-02-01 瑞士商諾華公司 抗ＴＧＦβ抗體及其他治療劑用於治療增殖性疾病之用途
AR125874A1 (es) 2021-05-18 2023-08-23 Novartis Ag Terapias de combinación
WO2023225320A1 (en) 2022-05-20 2023-11-23 Novartis Ag Epha2 bcl-xl inhibitor antibody-drug conjugates and methods of use thereof
WO2023225336A1 (en) 2022-05-20 2023-11-23 Novartis Ag Met bcl-xl inhibitor antibody-drug conjugates and methods of use thereof
WO2024033381A1 (en) 2022-08-10 2024-02-15 Vib Vzw Inhibition of tcf4/itf2 in the treatment of cancer

Family Cites Families (65)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU11248A1 (ru) 1927-03-29 1929-09-30 В.С. Григорьев Способ очистки антрацена
ZA711710B (en) * 1970-05-28 1971-12-29 Squibb & Sons Inc Amino derivatives of purazolo-pyridine carboxylic acids and esters
GB8827305D0 (en) 1988-11-23 1988-12-29 British Bio Technology Compounds
ATE174917T1 (de) * 1991-04-22 1999-01-15 Otsuka Pharma Co Ltd Pyrazolo(1,5-a>pyrimidinderivate und sie enthaltende antiinflammatorische mittel
US5455258A (en) 1993-01-06 1995-10-03 Ciba-Geigy Corporation Arylsulfonamido-substituted hydroxamic acids
JPH08176070A (ja) 1994-12-19 1996-07-09 Mitsubishi Chem Corp ジデプシド誘導体及びｐｉ３キナーゼ阻害剤
JPH08175990A (ja) 1994-12-19 1996-07-09 Mitsubishi Chem Corp Ｐｉ３キナーゼ阻害剤とその製造法
US5863949A (en) 1995-03-08 1999-01-26 Pfizer Inc Arylsulfonylamino hydroxamic acid derivatives
JP3053222B2 (ja) 1995-04-20 2000-06-19 ファイザー・インコーポレーテッド Ｍｍｐおよびｔｎｆ抑制剤としてのアリールスルホニルヒドロキサム酸誘導体
GB9521987D0 (en) 1995-10-26 1996-01-03 Ludwig Inst Cancer Res Phosphoinositide 3-kinase modulators
GB9624482D0 (en) 1995-12-18 1997-01-15 Zeneca Phaema S A Chemical compounds
ATE225343T1 (de) 1995-12-20 2002-10-15 Hoffmann La Roche Matrix-metalloprotease inhibitoren
EP0880508B1 (en) 1996-02-13 2003-04-16 AstraZeneca AB Quinazoline derivatives as vegf inhibitors
ATE211134T1 (de) 1996-03-05 2002-01-15 4-anilinochinazolin derivate
EP0818442A3 (en) 1996-07-12 1998-12-30 Pfizer Inc. Cyclic sulphone derivatives as inhibitors of metalloproteinases and of the production of tumour necrosis factor
TR199900066T2 (xx) 1996-07-18 1999-04-21 Pfizer Inc. Matriks metalloproteazlar�n fosfinat bazl� inhibit�rleri
SK21499A3 (en) 1996-08-23 2000-05-16 Pfizer Arylsulfonylamino hydroxamic acid derivatives
GB9718972D0 (en) 1996-09-25 1997-11-12 Zeneca Ltd Chemical compounds
US6077864A (en) 1997-01-06 2000-06-20 Pfizer Inc. Cyclic sulfone derivatives
DE69817801T2 (de) 1997-02-03 2004-03-11 Pfizer Products Inc., Groton Arylsulfonylhydroxamsäurederivate
BR9807824A (pt) 1997-02-07 2000-03-08 Pfizer Derivados de n-hidróxi-beta-sulfonil-propionamida e seu uso como inibidores de metaloproteinases de matriz
EP0960098A1 (en) 1997-02-11 1999-12-01 Pfizer Inc. Arylsulfonyl hydroxamic acid derivatives
JP4367866B2 (ja) 1997-02-12 2009-11-18 ザ リージェンツ オブ ジ ユニバーシティ オブ ミシガン 肺癌用のタンパク質マーカーおよびその使用
TR200000368T2 (tr) 1997-08-08 2000-07-21 Pfizer Products Inc. Ariloksiariarilsülfonilamino hidroksamik asit türevleri.
GB9725782D0 (en) 1997-12-05 1998-02-04 Pfizer Ltd Therapeutic agents
GB9801690D0 (en) 1998-01-27 1998-03-25 Pfizer Ltd Therapeutic agents
JP4462654B2 (ja) 1998-03-26 2010-05-12 ソニー株式会社 映像素材選択装置及び映像素材選択方法
PA8469401A1 (es) 1998-04-10 2000-05-24 Pfizer Prod Inc Derivados biciclicos del acido hidroxamico
PA8469501A1 (es) 1998-04-10 2000-09-29 Pfizer Prod Inc Hidroxamidas del acido (4-arilsulfonilamino)-tetrahidropiran-4-carboxilico
DE69915004T2 (de) 1998-11-05 2004-09-09 Pfizer Products Inc., Groton 5-Oxo-pyrrolidine-2-Carbonsäure-Hydroxamidderivate
HUP0105113A3 (en) 1999-01-13 2004-11-29 Warner Lambert Co Benzoheterocycles and their use as mek inhibitors and pharmaceutical compositions containing the compounds
ATE482946T1 (de) 1999-02-10 2010-10-15 Astrazeneca Ab Chinazolinderivate als angiogenesehemmer und zwischenprodukte dafür
PL352835A1 (en) 1999-07-16 2003-09-08 Warner-Lambert Company Method for treating chronic pain using mek inhibitors
MXPA02004366A (es) 1999-11-05 2002-11-07 Astrazeneca Ab Derivados de quinazolina como inhibidores vegf.
US6420365B1 (en) * 2000-01-18 2002-07-16 Neurogen Corporation Imidazopyridines and related derivatives as selective modulators of bradykinin B2 receptors
SK287142B6 (sk) 2000-02-15 2010-01-07 Sugen, Inc. Inhibítory proteínkináz na báze pyrolom substituovaného 2-indolinónu, farmaceutický prípravok s ich obsahom a ich použitie
JP2001247477A (ja) 2000-03-03 2001-09-11 Teikoku Hormone Mfg Co Ltd 抗腫瘍剤
US6608053B2 (en) 2000-04-27 2003-08-19 Yamanouchi Pharmaceutical Co., Ltd. Fused heteroaryl derivatives
US6403588B1 (en) 2000-04-27 2002-06-11 Yamanouchi Pharmaceutical Co., Ltd. Imidazopyridine derivatives
JP2002020386A (ja) * 2000-07-07 2002-01-23 Ono Pharmaceut Co Ltd ピラゾロピリジン誘導体
FR2811987A1 (fr) 2000-07-18 2002-01-25 Expansia Sa Procede de preparation du 2,2'-dithiobis(ethanesulfonate) de disodium
EP1304324B1 (en) 2000-07-18 2007-10-03 Dainippon Sumitomo Pharma Co., Ltd. Serotonin reuptake inhibitors
CN1219753C (zh) * 2000-07-19 2005-09-21 沃尼尔·朗伯公司 4－碘苯氨基苯氧肟酸的氧合酯
CA2454976C (en) 2001-07-26 2011-05-10 Santen Pharmaceutical Co., Ltd. Therapeutic agent for glaucoma comprising compound having pi3 kinase inhibitory action as active ingredient
US6703414B2 (en) 2001-09-14 2004-03-09 Arizona Board Of Regents On Behalf Of The University Of Arizona Device and method for treating restenosis
AU2002357667A1 (en) 2001-10-24 2003-05-06 Iconix Pharmaceuticals, Inc. Modulators of phosphoinositide 3-kinase
AU2002349912A1 (en) 2001-10-24 2003-05-06 Iconix Pharmaceuticals, Inc. Modulators of phosphoinositide 3-kinase
JP2005509645A (ja) 2001-10-30 2005-04-14 ファルマシア・コーポレーション 炎症処置用のヘテロ芳香族カルボキサミド誘導体
AU2003245700A1 (en) 2002-02-12 2003-09-04 Glaxo Group Limited Pyrazolopyridine derivatives
UA76837C2 (uk) * 2002-03-13 2006-09-15 Еррей Байофарма Інк. N3 алкіловані похідні бензімідазолу як інгібітори мек
ES2549159T3 (es) 2002-03-13 2015-10-23 Array Biopharma, Inc. Derivados de bencimidazol N3-alquilados como inhibidores de MEK
US20040092561A1 (en) 2002-11-07 2004-05-13 Thomas Ruckle Azolidinone-vinyl fused -benzene derivatives
AU2003255529B2 (en) 2002-07-10 2008-11-20 Laboratoires Serono Sa Use of compounds for increasing spermatozoa motility
BR0312752A (pt) 2002-07-10 2005-04-26 Applied Research Systems Derivados de benzeno fundido de azolidinona-vinil
AU2003255845A1 (en) 2002-08-22 2004-03-11 Piramed Limited Phosphadidylinositol 3,5-biphosphate inhibitors as anti-viral agents
ATE378336T1 (de) * 2002-09-19 2007-11-15 Schering Corp Imidazopyridine als hemmstoffe cyclin abhängiger kinasen
SE0301373D0 (sv) 2003-05-09 2003-05-09 Astrazeneca Ab Novel compounds
US20050049276A1 (en) 2003-07-23 2005-03-03 Warner-Lambert Company, Llc Imidazopyridines and triazolopyridines
US7144907B2 (en) * 2003-09-03 2006-12-05 Array Biopharma Inc. Heterocyclic inhibitors of MEK and methods of use thereof
DK1689233T3 (da) * 2003-11-19 2012-10-15 Array Biopharma Inc Bicykliske inhibitorer af MEK
GB0423653D0 (en) 2004-10-25 2004-11-24 Piramed Ltd Pharmaceutical compounds
DE602005016718D1 (de) * 2004-12-01 2009-10-29 Merck Serono Sa Coinsins Ä1,2,4ütriazoloä4,3-aüpyridin-derivative zur behandlung hyperproliferativer erkrankungen
GB0520657D0 (en) 2005-10-11 2005-11-16 Ludwig Inst Cancer Res Pharmaceutical compounds
MY180595A (en) 2006-12-07 2020-12-03 Genentech Inc Phosphoinositide 3-kinase inhibitor compounds and methods of use
RU2498985C2 (ru) * 2007-12-19 2013-11-20 Дженентек, Инк. 8-анилиноимидазопиридины и способы их использования

Also Published As

Publication number Publication date
EP2690101A1 (en) 2014-01-29
EP2222675A1 (en) 2010-09-01
HRP20151002T1 (hr) 2015-10-23
SI2222675T1 (sl) 2013-12-31
TWI441820B (zh) 2014-06-21
RU2441004C1 (ru) 2012-01-27
CA2706571C (en) 2012-11-27
TW200932745A (en) 2009-08-01
US20100004269A1 (en) 2010-01-07
HK1188209A1 (en) 2014-04-25
HUE025192T2 (en) 2016-01-28
PE20131210A1 (es) 2013-10-31
US7923456B2 (en) 2011-04-12
IL205977A0 (en) 2010-11-30
CY1116681T1 (el) 2017-03-15
BRPI0819529A2 (pt) 2015-05-26
AR069803A1 (es) 2010-02-17
MX2010006800A (es) 2010-10-05
AU2008343065A1 (en) 2009-07-09
PT2690101E (pt) 2015-10-08
KR20100093608A (ko) 2010-08-25
EP2222675B1 (en) 2013-09-11
CN101945870B (zh) 2012-10-03
CA2706571A1 (en) 2009-07-09
US9206174B2 (en) 2015-12-08
DK2222675T3 (da) 2013-11-04
US20110158990A1 (en) 2011-06-30
PL2222675T3 (pl) 2014-02-28
JP5421925B2 (ja) 2014-02-19
ZA201003625B (en) 2011-08-31
PE20091158A1 (es) 2009-08-28
EP2690101B1 (en) 2015-06-24
US8288408B2 (en) 2012-10-16
WO2009085983A1 (en) 2009-07-09
KR101195329B1 (ko) 2012-10-29
SI2690101T1 (sl) 2015-10-30
CL2008003810A1 (es) 2009-05-22
AU2008343065B2 (en) 2012-04-05
JP2011507889A (ja) 2011-03-10
PT2222675E (pt) 2013-11-13
MY158829A (en) 2016-11-15
ES2546171T3 (es) 2015-09-21
HK1147254A1 (en) 2011-08-05
US20120309765A1 (en) 2012-12-06
NZ586802A (en) 2012-03-30
CY1114663T1 (el) 2016-10-05
CN101945870A (zh) 2011-01-12
PL2690101T3 (pl) 2015-12-31
IL205977A (en) 2015-05-31
US20130150584A1 (en) 2013-06-13
ES2437141T3 (es) 2014-01-09

Similar Documents

Publication Publication Date Title
DK2690101T3 (da) 5-anilinoimidazopyridiner og fremgangsmåder til anvendelse
EP2307364B1 (en) Isoindolone derivatives as mek kinase inhibitors and methods of use
EP2069359B1 (en) Aza-benzothiophenyl compounds and methods of use
AU2008343062B2 (en) 8-Anilinoimidazopyridines and their use as anti-cancer and/or anti-inflammatory agents
CA2708176A1 (en) Azaindolizines and methods of use
ES2368305T3 (es) 8-anilinoimidazopiridinas y su uso como agentes anticancerígenos y/o antiinflamatorios.