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

5-anilinoimidazopyridiner og fremgangsmåder til anvendelse Download PDF

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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
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cr14r15
cr19r20
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imidazo
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Stephen Price
Robert Heald
Wendy Lee
Mark E Zak
Joanne Frances Mary Hewitt
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Genentech Inc
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    • 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
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    • 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
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • 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
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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.
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Families Citing this family (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009018657A1 (en) 2007-08-03 2009-02-12 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
KR20100098534A (ko) 2007-12-19 2010-09-07 베링거 인겔하임 인터내셔날 게엠베하 바이러스 폴리머라제 억제제
US8343977B2 (en) 2009-12-30 2013-01-01 Arqule, Inc. Substituted triazolo-pyrimidine compounds
US8329705B2 (en) 2009-12-30 2012-12-11 Arqule, Inc. Substituted triazolo-pyrazine 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
MY170117A (en) 2011-08-01 2019-07-05 Genentech Inc Methods of treating cancer using pd-1 axis binding antagonists and mek inhibitors
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
SG11201507477XA (en) 2013-03-14 2015-10-29 Genentech Inc Combinations of a mek inhibitor compound with an her3/egfr inhibitor compound and methods of use
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
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
ES2770684T3 (es) 2014-03-14 2020-07-02 Novartis Ag Moléculas de anticuerpos contra LAG-3 y usos de los mismos
EP3169361B1 (en) 2014-07-15 2019-06-19 F.Hoffmann-La Roche Ag Compositions for treating cancer using pd-1 axis binding antagonists and mek inhibitors
CN105315293A (zh) * 2014-07-29 2016-02-10 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
KR20170060042A (ko) 2014-09-13 2017-05-31 노파르티스 아게 Alk 억제제의 조합 요법
JP2017535528A (ja) 2014-10-03 2017-11-30 ノバルティス アーゲー 組み合わせ治療
US20170248603A1 (en) 2014-10-06 2017-08-31 Dana-Farber Cancer Institute, Inc. Angiopoiten-2 biomarkers predictive of anti-immune checkpoint response
MX2017004810A (es) 2014-10-14 2017-10-16 Novartis Ag Moleculas de anticuerpo que se unen a pd-l1 y usos de las mismas.
WO2016100882A1 (en) 2014-12-19 2016-06-23 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
EP3964528A1 (en) 2015-07-29 2022-03-09 Novartis AG Combination therapies comprising antibody molecules to lag-3
WO2017019897A1 (en) 2015-07-29 2017-02-02 Novartis Ag Combination therapies comprising antibody molecules to tim-3
US20180222982A1 (en) 2015-07-29 2018-08-09 Novartis Ag Combination therapies comprising antibody molecules to pd-1
WO2017033113A1 (en) 2015-08-21 2017-03-02 Acerta Pharma B.V. Therapeutic combinations of a mek inhibitor and a btk inhibitor
MX2018005550A (es) 2015-11-03 2019-07-18 Janssen Biotech Inc Anticuerpos que se unen especificamente a tim-3 y sus usos.
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
JP2019503349A (ja) 2015-12-17 2019-02-07 ノバルティス アーゲー Ｐｄ−１に対する抗体分子およびその使用
AU2017249229A1 (en) 2016-04-15 2018-10-04 Genentech, Inc. Diagnostic and therapeutic methods for cancer
CN109153682B (zh) 2016-05-20 2021-05-25 豪夫迈·罗氏有限公司 用于治疗感染性疾病的具有氧、硫和氮连接基的新的吡嗪化合物
WO2018011100A1 (en) 2016-07-14 2018-01-18 F. Hoffmann-La Roche Ag Novel tetrahydropyrazolopyridine compounds for the treatment of infectious diseases
CN109415368B (zh) * 2016-07-14 2021-04-30 豪夫迈·罗氏有限公司 用于治疗感染性疾病的羧基6,7-二氢-4H-吡唑并[1,5-a]吡嗪化合物
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
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
EP3505517A4 (en) * 2016-08-23 2020-01-15 Beijing InnoCare Pharma Tech Co., Ltd. FUSED HETEROCYCLIC DERIVATIVE, ITS PREPARATION METHOD AND ITS MEDICAL USE
MX2020002553A (es) 2017-09-08 2020-07-22 Hoffmann La Roche Metodos de diagnostico y terapeuticos para el cancer.
AU2018368731A1 (en) 2017-11-16 2020-05-14 Novartis Ag Combination therapies
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
CN113473978A (zh) * 2018-11-20 2021-10-01 恩福莱克逊治疗有限公司 用于治疗皮肤疾病氰基芳烃-苯胺化合物
CA3123511A1 (en) 2018-12-20 2020-06-25 Novartis Ag Dosing regimen and pharmaceutical combination comprising 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives
WO2020165833A1 (en) 2019-02-15 2020-08-20 Novartis Ag 3-(1-oxo-5-(piperidin-4-yl)isoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof
CA3123519A1 (en) 2019-02-15 2020-08-20 Novartis Ag Substituted 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof
MX2021012767A (es) 2019-04-19 2021-11-18 Janssen Biotech Inc Metodos para tratar el cancer de prostata con un anticuerpo anti-psma/cd3.
MX2021013105A (es) * 2019-04-30 2021-11-17 Aicuris Gmbh & Co Kg Nuevas oxalil piperazinas activas contra el virus de la hepatitis b (vhb).
CA3165274A1 (en) 2019-12-20 2021-06-24 Novartis Ag Combination of anti tim-3 antibody mbg453 and anti tgf-beta antibody nis793, with or without decitabine or the anti pd-1 antibody spartalizumab, for treating myelofibrosis and myelodysplastic syndrome
JP2023531676A (ja) 2020-06-23 2023-07-25 ノバルティス アーゲー ３－（１－オキソイソインドリン－２－イル）ピぺリジン－２，６－ジオン誘導体を含む投与レジメン
BR112023015097A2 (pt) 2021-01-28 2023-10-03 Janssen Biotech Inc Proteínas de ligação a psma e usos das mesmas
WO2022169780A1 (en) 2021-02-02 2022-08-11 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
WO2023225336A1 (en) 2022-05-20 2023-11-23 Novartis Ag Met bcl-xl inhibitor antibody-drug conjugates and methods of use thereof
WO2023225320A1 (en) 2022-05-20 2023-11-23 Novartis Ag Epha2 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
CA920592A (en) * 1970-05-28 1973-02-06 Denzel Theodor Amino derivatives of pyrazolo-pyridine carboxylic acids and esters
GB8827305D0 (en) 1988-11-23 1988-12-29 British Bio Technology Compounds
EP0591528B1 (en) 1991-04-22 1998-12-23 Otsuka Pharmaceutical Factory, Inc. PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVE AND ANTI-INFLAMMATORY CONTAINING THE SAME
US5455258A (en) 1993-01-06 1995-10-03 Ciba-Geigy Corporation Arylsulfonamido-substituted hydroxamic acids
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
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
US5863949A (en) 1995-03-08 1999-01-26 Pfizer Inc Arylsulfonylamino hydroxamic acid derivatives
WO1996033172A1 (en) 1995-04-20 1996-10-24 Pfizer Inc. Arylsulfonyl hydroxamic acid derivatives as mmp and tnf inhibitors
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
EP0780386B1 (en) 1995-12-20 2002-10-02 F. Hoffmann-La Roche Ag Matrix metalloprotease inhibitors
HUP9901155A3 (en) 1996-02-13 2003-04-28 Astrazeneca Ab Quinazoline derivatives as vegf inhibitors
DK0885198T3 (da) 1996-03-05 2002-03-25 Astrazeneca Ab 4-Anilinoquinazolinderivater
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
EA199900036A1 (ru) 1996-07-18 1999-06-24 Пфайзер Инк Ингибиторы металлопротеаз матрикса на основе фосфинатов, фармацевтическая композиция, способ лечения
JP2000501423A (ja) 1996-08-23 2000-02-08 ファイザー インク． アリールスルホニルアミノヒドロキサム酸誘導体
GB9718972D0 (en) 1996-09-25 1997-11-12 Zeneca Ltd Chemical compounds
EP0950059B1 (en) 1997-01-06 2004-08-04 Pfizer Inc. Cyclic sulfone derivatives
PL335027A1 (en) 1997-02-03 2000-03-27 Pfizer Prod Inc Derivatives of arylsulphonylamino hydroxamic acid
EP0966438A1 (en) 1997-02-07 1999-12-29 Pfizer Inc. N-hydroxy-beta-sulfonyl-propionamide derivatives and their use as inhibitors of matrix metalloproteinases
JP3710489B2 (ja) 1997-02-11 2005-10-26 ファイザー・インク アリールスルホニルヒドロキサム酸誘導体
DE69837529T2 (de) 1997-02-12 2007-07-26 Electrophoretics Ltd., Cobham Proteinmarker für lungenkrebs und deren verwendung
WO1999007675A1 (en) 1997-08-08 1999-02-18 Pfizer Products Inc. Aryloxyarylsulfonylamino hydroxamic acid derivatives
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
ATE260255T1 (de) 1998-11-05 2004-03-15 Pfizer Prod Inc 5-oxo-pyrrolidine-2-carbonsäure- hydroxamidderivate
DE69926800T2 (de) * 1999-01-13 2006-05-18 Warner-Lambert Company Llc Benzoheterozyklen und ihre verwendung als mek inhibitoren
EE05345B1 (et) 1999-02-10 2010-10-15 Astrazeneca Ab Kinasoliini derivaadid angiogeneesi inhibiitoritena
WO2001005390A2 (en) 1999-07-16 2001-01-25 Warner-Lambert Company Method for treating chronic pain using mek inhibitors
PL203782B1 (pl) 1999-11-05 2009-11-30 Astrazeneca Ab Pochodne chinazoliny,sposoby ich wytwarzania,ich kompozycje farmaceutyczne oraz ich zastosowania
AU2001236471A1 (en) * 2000-01-18 2001-07-31 Neurogen Corporation Imidazopyridines and related azacyclic derivatives as selective modulators of bradykinin b2 receptors
AU2001239770B2 (en) 2000-02-15 2006-01-05 Pharmacia & Upjohn Company Pyrrole substituted 2-indolinone protein kinase inhibitors
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
JP5079202B2 (ja) 2000-07-18 2012-11-21 大日本住友製薬株式会社 セロトニン再取り込み阻害剤
JP3811775B2 (ja) 2000-07-19 2006-08-23 ワーナー−ランバート カンパニー リミティド ライアビリティー カンパニー ４−ヨードフェニルアミノベンズヒドロキサム酸の酸素化エステル
WO2003018057A1 (fr) 2001-07-26 2003-03-06 Santen Pharmaceutical Co., Ltd. Remede contre le glaucome contenant en tant qu'ingredient actif un compose presentant un effet inhibiteur de la kinase pi3
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
WO2003034997A2 (en) 2001-10-24 2003-05-01 Iconix Pharmaceuticals, Inc. Modulators of phosphoinositide 3-kinase
WO2003035618A2 (en) 2001-10-24 2003-05-01 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
WO2003068773A1 (en) 2002-02-12 2003-08-21 Glaxo Group Limited Pyrazolopyridine derivatives
IL163995A0 (en) 2002-03-13 2005-12-18 Array Biopharma Inc N3 alkylated benzimidazole derivatives as mek inhibitors
CN1652792A (zh) * 2002-03-13 2005-08-10 阵列生物制药公司 作为mek抑制剂的n3烷基化苯并咪唑衍生物
US20050222225A1 (en) 2002-07-10 2005-10-06 Applied Research Systems Ars Holding Nv Use of compounds for increasing spermatozoa motility
US20040092561A1 (en) 2002-11-07 2004-05-13 Thomas Ruckle Azolidinone-vinyl fused -benzene derivatives
JP4782564B2 (ja) 2002-07-10 2011-09-28 メルク セローノ ソシエテ アノニム アゾリジノン−ビニル縮合−ベンゼン誘導体
AU2003255845A1 (en) 2002-08-22 2004-03-11 Piramed Limited Phosphadidylinositol 3,5-biphosphate inhibitors as anti-viral agents
CN100549011C (zh) * 2002-09-19 2009-10-14 先灵公司 用作细胞周期蛋白依赖性激酶抑制剂的新颖咪唑并吡啶
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
KR101190912B1 (ko) * 2003-11-19 2012-10-12 어레이 바이오파마 인크. Ｍｅｋ의 헤테로시클릭 억제제 및 그의 사용 방법
GB0423653D0 (en) 2004-10-25 2004-11-24 Piramed Ltd Pharmaceutical compounds
WO2006058752A1 (en) * 2004-12-01 2006-06-08 Laboratoires Serono S.A. [1,2,4]triazolo[4,3-a]pyridine derivatives for the treatment of hyperproliferative diseases
GB0520657D0 (en) 2005-10-11 2005-11-16 Ludwig Inst Cancer Res Pharmaceutical compounds
AU2007329352B2 (en) 2006-12-07 2013-01-17 F. Hoffmann-La Roche Ag 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

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