JP2013523884A5 - - Google Patents
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- Publication number
- JP2013523884A5 JP2013523884A5 JP2013504972A JP2013504972A JP2013523884A5 JP 2013523884 A5 JP2013523884 A5 JP 2013523884A5 JP 2013504972 A JP2013504972 A JP 2013504972A JP 2013504972 A JP2013504972 A JP 2013504972A JP 2013523884 A5 JP2013523884 A5 JP 2013523884A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- alkyl
- imidazo
- pyrimidin
- methyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
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- 125000000217 alkyl group Chemical group 0.000 claims description 365
- 150000001875 compounds Chemical class 0.000 claims description 191
- 125000001424 substituent group Chemical group 0.000 claims description 71
- 150000003839 salts Chemical class 0.000 claims description 67
- 239000012453 solvate Substances 0.000 claims description 66
- -1 pyridinonyl Chemical group 0.000 claims description 63
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 41
- 125000001153 fluoro group Chemical group F* 0.000 claims description 34
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 230000008878 coupling Effects 0.000 claims description 18
- 238000010168 coupling process Methods 0.000 claims description 18
- 238000005859 coupling reaction Methods 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000003566 oxetanyl group Chemical group 0.000 claims description 8
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 239000012025 fluorinating agent Substances 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 2
- FHBAQURBTKEYHG-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[3-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrrol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(C=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 FHBAQURBTKEYHG-UHFFFAOYSA-N 0.000 claims description 2
- KLNXUTSCUIBQGB-UHFFFAOYSA-N 2-bromo-2-fluoroacetaldehyde Chemical compound FC(Br)C=O KLNXUTSCUIBQGB-UHFFFAOYSA-N 0.000 claims description 2
- AVAHZUUYBFUOPN-UHFFFAOYSA-N 2-chloro-2-fluoroacetaldehyde Chemical compound FC(Cl)C=O AVAHZUUYBFUOPN-UHFFFAOYSA-N 0.000 claims description 2
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Chemical class CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 208000037979 autoimmune inflammatory disease Diseases 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000006380 bromopyridyl group Chemical group 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 238000002054 transplantation Methods 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 6
- CDGWLOBEPYFSQW-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[7-(4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C=2C=CC(=CC=2)N2CCOCC2)C=NN1C(CC#N)C1CCCC1 CDGWLOBEPYFSQW-UHFFFAOYSA-N 0.000 claims 3
- PMKAQVQNDAXKOW-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[7-[4-(1-methylpiperidin-4-yl)phenyl]imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1CN(C)CCC1C1=CC=C(C=2N=C(N3C=CN=C3C=2)C2=CN(N=C2)C(CC#N)C2CCCC2)C=C1 PMKAQVQNDAXKOW-UHFFFAOYSA-N 0.000 claims 3
- YUPDWXZOLVVALZ-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 YUPDWXZOLVVALZ-UHFFFAOYSA-N 0.000 claims 3
- GEYUNVRSROHFKM-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]pentanedinitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)CC#N)=N1 GEYUNVRSROHFKM-UHFFFAOYSA-N 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 2
- ABNBEHYCFTZPKW-GDBMZVCRSA-N (3r)-3-[(1r)-2,2-difluorocyclopropyl]-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)[C@H](CC#N)[C@@H]2C(C2)(F)F)=N1 ABNBEHYCFTZPKW-GDBMZVCRSA-N 0.000 claims 1
- ABNBEHYCFTZPKW-GOEBONIOSA-N (3r)-3-[(1s)-2,2-difluorocyclopropyl]-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)[C@H](CC#N)[C@H]2C(C2)(F)F)=N1 ABNBEHYCFTZPKW-GOEBONIOSA-N 0.000 claims 1
- ABNBEHYCFTZPKW-HOCLYGCPSA-N (3s)-3-[(1s)-2,2-difluorocyclopropyl]-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)[C@@H](CC#N)[C@H]2C(C2)(F)F)=N1 ABNBEHYCFTZPKW-HOCLYGCPSA-N 0.000 claims 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 1
- STHHLVCQSLRQNI-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octane Chemical compound C1C2CCN1CCC2 STHHLVCQSLRQNI-UHFFFAOYSA-N 0.000 claims 1
- BVXLHMZUEHXJBO-UHFFFAOYSA-N 2-[1-(1,3-difluoropropan-2-yl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)C(CF)CF)=N1 BVXLHMZUEHXJBO-UHFFFAOYSA-N 0.000 claims 1
- RRXZOVJYCGCGPH-UHFFFAOYSA-N 2-[1-(2,2-difluoroethyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC(F)F)C2)=N1 RRXZOVJYCGCGPH-UHFFFAOYSA-N 0.000 claims 1
- XMUCZZPNAALHEK-UHFFFAOYSA-N 2-[1-(2-fluoroethyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CCF)C2)=N1 XMUCZZPNAALHEK-UHFFFAOYSA-N 0.000 claims 1
- UVPTWQHOIAUESY-UHFFFAOYSA-N 2-[1-(2-methylpropyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1N(CC(C)C)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 UVPTWQHOIAUESY-UHFFFAOYSA-N 0.000 claims 1
- WSXKODFFQDPKQQ-UHFFFAOYSA-N 2-[1-(3-fluoropropyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CCCF)C2)=N1 WSXKODFFQDPKQQ-UHFFFAOYSA-N 0.000 claims 1
- LIZHKRHZDLAJCN-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C=2C=CC=CC=2)=N1 LIZHKRHZDLAJCN-UHFFFAOYSA-N 0.000 claims 1
- IXDYSBQNTZFBQM-UHFFFAOYSA-N 2-[1-(cyanomethyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC#N)C2)=N1 IXDYSBQNTZFBQM-UHFFFAOYSA-N 0.000 claims 1
- AHXUTYXPZLGWHS-UHFFFAOYSA-N 2-[1-(cyclobutylmethyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC3CCC3)C2)=N1 AHXUTYXPZLGWHS-UHFFFAOYSA-N 0.000 claims 1
- NUHSETASQOIQEV-UHFFFAOYSA-N 2-[1-(cyclopropylmethyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC3CC3)C2)=N1 NUHSETASQOIQEV-UHFFFAOYSA-N 0.000 claims 1
- MZRDVCTYXZXBCQ-UHFFFAOYSA-N 2-[1-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]cyclohexyl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CCCCC2)=N1 MZRDVCTYXZXBCQ-UHFFFAOYSA-N 0.000 claims 1
- AXJNUSNMBMLDCE-UHFFFAOYSA-N 2-[1-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]cyclopentyl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CCCC2)=N1 AXJNUSNMBMLDCE-UHFFFAOYSA-N 0.000 claims 1
- GRVGHRKEVBNTAR-UHFFFAOYSA-N 2-[1-acetyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1N(C(=O)C)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 GRVGHRKEVBNTAR-UHFFFAOYSA-N 0.000 claims 1
- LYNKUIAJEDKUOU-UHFFFAOYSA-N 2-[1-acetyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]pyrrolidin-3-yl]acetonitrile Chemical compound C1N(C(=O)C)CCC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 LYNKUIAJEDKUOU-UHFFFAOYSA-N 0.000 claims 1
- WIKHNPCHNOOJMO-UHFFFAOYSA-N 2-[1-but-2-ynyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1N(CC#CC)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 WIKHNPCHNOOJMO-UHFFFAOYSA-N 0.000 claims 1
- AWVZDWQVTXEGAK-UHFFFAOYSA-N 2-[1-cyclohexylsulfonyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CCCCC2)=N1 AWVZDWQVTXEGAK-UHFFFAOYSA-N 0.000 claims 1
- MEKZXNYRRWVDBH-UHFFFAOYSA-N 2-[1-cyclopropyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)C2CC2)=N1 MEKZXNYRRWVDBH-UHFFFAOYSA-N 0.000 claims 1
- DTOPBQTXJVBHDA-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 DTOPBQTXJVBHDA-UHFFFAOYSA-N 0.000 claims 1
- KVSNEJVQFAUGNO-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[4-[7-(2-methoxypyrimidin-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NC(OC)=NC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 KVSNEJVQFAUGNO-UHFFFAOYSA-N 0.000 claims 1
- VRVAYYXJPPDRDE-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[4-[7-(2-methyl-1,3-thiazol-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound S1C(C)=NC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 VRVAYYXJPPDRDE-UHFFFAOYSA-N 0.000 claims 1
- BVAOKWYKPDLRNN-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[4-[7-(4-methoxyphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=CC(OC)=CC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 BVAOKWYKPDLRNN-UHFFFAOYSA-N 0.000 claims 1
- GDQAHRLJKRQHDZ-UHFFFAOYSA-N 2-[1-ethyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1N(CC)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 GDQAHRLJKRQHDZ-UHFFFAOYSA-N 0.000 claims 1
- QTISHRMBUYAIPL-UHFFFAOYSA-N 2-[1-ethyl-4-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(CC)CCC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 QTISHRMBUYAIPL-UHFFFAOYSA-N 0.000 claims 1
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- DFWMDEUJRFPCJI-UHFFFAOYSA-N 2-[3-[4-[7-(4-methoxyphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(trifluoromethylsulfonyl)azetidin-3-yl]acetonitrile Chemical compound C1=CC(OC)=CC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C(F)(F)F)=N1 DFWMDEUJRFPCJI-UHFFFAOYSA-N 0.000 claims 1
- IZRUVVZILHUJBC-UHFFFAOYSA-N 2-[3-[4-[7-[1-(oxetan-3-yl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(2,2,2-trifluoroethyl)azetidin-3-yl]acetonitrile Chemical compound C1N(CC(F)(F)F)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(N=C2)C2COC2)=C1 IZRUVVZILHUJBC-UHFFFAOYSA-N 0.000 claims 1
- MYFUQDIKPISEBR-UHFFFAOYSA-N 2-[3-[4-[7-[1-(oxetan-3-yl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(2,2,3,3,3-pentafluoropropyl)azetidin-3-yl]acetonitrile Chemical compound C1N(CC(F)(F)C(F)(F)F)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(N=C2)C2COC2)=C1 MYFUQDIKPISEBR-UHFFFAOYSA-N 0.000 claims 1
- NSOQJYLCMLVDSD-UHFFFAOYSA-N 2-[3-[4-[7-[4-(4-methylpiperazin-1-yl)phenyl]imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(2,2,2-trifluoroethyl)azetidin-3-yl]acetonitrile Chemical compound C1CN(C)CCN1C1=CC=C(C=2N=C(N3C=CN=C3C=2)C2=CN(N=C2)C2(CC#N)CN(CC(F)(F)F)C2)C=C1 NSOQJYLCMLVDSD-UHFFFAOYSA-N 0.000 claims 1
- HMZOXQBZHCFMOR-UHFFFAOYSA-N 2-[3-[4-[7-[4-(4-methylpiperazin-1-yl)phenyl]imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(trifluoromethylsulfonyl)azetidin-3-yl]acetonitrile Chemical compound C1CN(C)CCN1C1=CC=C(C=2N=C(N3C=CN=C3C=2)C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C(F)(F)F)C=C1 HMZOXQBZHCFMOR-UHFFFAOYSA-N 0.000 claims 1
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- KRKSMAMKUHJRAO-UHFFFAOYSA-N 3-(5-bromopyridin-3-yl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2C=C(Br)C=NC=2)=N1 KRKSMAMKUHJRAO-UHFFFAOYSA-N 0.000 claims 1
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- AJPWDEWJGZFKES-UHFFFAOYSA-N 3-[4-[3-chloro-7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-3-cyclopropylpropanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=C(Cl)N2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 AJPWDEWJGZFKES-UHFFFAOYSA-N 0.000 claims 1
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- UQFLUXXENJUNNR-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2C=C(C=CC=2)C(F)(F)F)=N1 UQFLUXXENJUNNR-UHFFFAOYSA-N 0.000 claims 1
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- QFKUHHHTOCDBBJ-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-3-pyridin-2-ylpropanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2N=CC=CC=2)=N1 QFKUHHHTOCDBBJ-UHFFFAOYSA-N 0.000 claims 1
- RARCFHGIWRCBSK-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-3-pyridin-3-ylpropanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2C=NC=CC=2)=N1 RARCFHGIWRCBSK-UHFFFAOYSA-N 0.000 claims 1
- OYSMCZSDTIWOJT-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-3-pyridin-4-ylpropanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2C=CN=CC=2)=N1 OYSMCZSDTIWOJT-UHFFFAOYSA-N 0.000 claims 1
- GXAMHDZDASSNKZ-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(CCC#N)N=C2)=N1 GXAMHDZDASSNKZ-UHFFFAOYSA-N 0.000 claims 1
- COIHEXKIXPEXTH-UHFFFAOYSA-N 3-[4-[7-(4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]butanenitrile Chemical compound C1=NN(C(CC#N)C)C=C1C1=NC(C=2C=CC(=CC=2)N2CCOCC2)=CC2=NC=CN12 COIHEXKIXPEXTH-UHFFFAOYSA-N 0.000 claims 1
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- CMQJUUYCKXJGGQ-UHFFFAOYSA-N 3-cyclobutyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CCC2)=N1 CMQJUUYCKXJGGQ-UHFFFAOYSA-N 0.000 claims 1
- MHBLMJUJRRLINT-UHFFFAOYSA-N 3-cyclopentyl-3-[3-methyl-4-[7-(4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound CC1=NN(C(CC#N)C2CCCC2)C=C1C(N1C=CN=C1C=1)=NC=1C(C=C1)=CC=C1N1CCOCC1 MHBLMJUJRRLINT-UHFFFAOYSA-N 0.000 claims 1
- JMUWHIMQRSJDOC-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CCCC2)=N1 JMUWHIMQRSJDOC-UHFFFAOYSA-N 0.000 claims 1
- AKPSVTAHTDVPLQ-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=NN(C=C2)C(CC#N)C2CC2)=N1 AKPSVTAHTDVPLQ-UHFFFAOYSA-N 0.000 claims 1
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- VRPDPZTVSKSYRJ-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[3-fluoro-7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=C(F)N2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 VRPDPZTVSKSYRJ-UHFFFAOYSA-N 0.000 claims 1
- DWAIHCDEWKZVTH-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1,2,3,4-tetrahydroisoquinolin-6-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C=2C=C3CCNCC3=CC=2)C=NN1C(CC#N)C1CC1 DWAIHCDEWKZVTH-UHFFFAOYSA-N 0.000 claims 1
- ZTKNHJIXJVXOBT-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1,2,3,4-tetrahydroisoquinolin-7-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C=2C=C3CNCCC3=CC=2)C=NN1C(CC#N)C1CC1 ZTKNHJIXJVXOBT-UHFFFAOYSA-N 0.000 claims 1
- VLWHWRQGLKVENE-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1,3-oxazol-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C=2OC=NC=2)C=NN1C(CC#N)C1CC1 VLWHWRQGLKVENE-UHFFFAOYSA-N 0.000 claims 1
- LAFPPLQHGHUMHU-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1,3-thiazol-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C=2SC=NC=2)C=NN1C(CC#N)C1CC1 LAFPPLQHGHUMHU-UHFFFAOYSA-N 0.000 claims 1
- QLKWQBWEZHFRCD-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1-ethylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(CC)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 QLKWQBWEZHFRCD-UHFFFAOYSA-N 0.000 claims 1
- QPWQVIRMVCSPIJ-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1-propan-2-ylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C(C)C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 QPWQVIRMVCSPIJ-UHFFFAOYSA-N 0.000 claims 1
- OLCSDVVNTNKXDO-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1h-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C2=CNN=C2)C=NN1C(CC#N)C1CC1 OLCSDVVNTNKXDO-UHFFFAOYSA-N 0.000 claims 1
- HMTOHHCQXJAJIR-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(2-methyl-1,3-thiazol-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound S1C(C)=NC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 HMTOHHCQXJAJIR-UHFFFAOYSA-N 0.000 claims 1
- CIKUAIFCICQYFL-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(2-methyl-3,4-dihydro-1h-isoquinolin-6-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C=1C=C2CN(C)CCC2=CC=1C(N=1)=CC2=NC=CN2C=1C(=C1)C=NN1C(CC#N)C1CC1 CIKUAIFCICQYFL-UHFFFAOYSA-N 0.000 claims 1
- SYKYCBPRCKWSDD-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C2CN(C)CCC2=CC=C1C(N=1)=CC2=NC=CN2C=1C(=C1)C=NN1C(CC#N)C1CC1 SYKYCBPRCKWSDD-UHFFFAOYSA-N 0.000 claims 1
- KXIGBXQAKMNERW-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(2-methylpyridin-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NC(C)=CC(C=2N=C(N3C=CN=C3C=2)C2=CN(N=C2)C(CC#N)C2CC2)=C1 KXIGBXQAKMNERW-UHFFFAOYSA-N 0.000 claims 1
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Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1966202E (pt) | 2005-12-13 | 2012-01-03 | Incyte Corp | Pirrolo[2,3-b] pirimidinas e pirrolo[2,3-b]piridinas substituídas com heteroarilo como inibidores de janus quinase |
| RS53245B2 (sr) | 2007-06-13 | 2022-10-31 | Incyte Holdings Corp | Soli inhibitora janus kinaze (r)-3-(4-(7h-pirolo(2,3-d) pirimidin-4-il)-1h-pirazol-1-il)-3-ciklopentilpropan-nitrila |
| TW201100429A (en) | 2009-05-22 | 2011-01-01 | Incyte Corp | N-(hetero)aryl-pyrrolidine derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines and pyrrol-3-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| PL2432472T3 (pl) | 2009-05-22 | 2020-03-31 | Incyte Holdings Corporation | 3-[4-(7H-Pirolo[2,3-d]pirymidyn-4-ylo)-1H-pirazol-1-ilo]oktano- lub heptano-nitryle jako inhibitory JAK |
| KR101903354B1 (ko) | 2009-06-17 | 2018-10-04 | 버텍스 파마슈티칼스 인코포레이티드 | 인플루엔자 바이러스 복제의 억제제 |
| TW201113285A (en) | 2009-09-01 | 2011-04-16 | Incyte Corp | Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| MX354212B (es) | 2010-03-10 | 2018-02-19 | Incyte Corp | Derivados de piperidin-4-il azetidina como inhibidores de janus cinasa 1 (jak1). |
| EA202091303A3 (ru) | 2010-05-21 | 2021-05-31 | Инсайт Холдингс Корпорейшн | Композиция ингибитора jak для местного применения |
| WO2012068440A1 (en) | 2010-11-19 | 2012-05-24 | Incyte Corporation | Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as jak inhibitors |
| CA2818542A1 (en) | 2010-11-19 | 2012-05-24 | Incyte Corporation | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| EP2651940A1 (en) | 2010-12-16 | 2013-10-23 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| CN103797010B (zh) | 2011-06-20 | 2016-02-24 | 因塞特控股公司 | 作为jak抑制剂的氮杂环丁烷基苯基、吡啶基或吡嗪基甲酰胺衍生物 |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物 |
| UA111854C2 (uk) * | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| BR112014008865A2 (pt) * | 2011-10-12 | 2017-04-25 | Array Biopharma Inc | imidazo[1,2-c]pirimidinas 5,7-substituídas |
| MX2014005565A (es) * | 2011-11-07 | 2014-05-30 | Vertex Pharma | Metodos para tratar enfermedades inflamatorias y composiciones farmaceuticas utiles para los mismos. |
| US9193733B2 (en) | 2012-05-18 | 2015-11-24 | Incyte Holdings Corporation | Piperidinylcyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as JAK inhibitors |
| JP6196678B2 (ja) | 2012-10-24 | 2017-09-13 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｃ型肝炎ウイルス阻害剤 |
| NZ708157A (en) | 2012-11-15 | 2019-07-26 | Incyte Holdings Corp | Sustained-release dosage forms of ruxolitinib |
| US20160123982A1 (en) | 2013-02-04 | 2016-05-05 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for assaying jak2 activity in red blood cells and uses thereof |
| TWI634121B (zh) * | 2013-03-06 | 2018-09-01 | 英塞特控股公司 | 用於製備ｊａｋ抑制劑之方法及中間物 |
| WO2014146249A1 (en) | 2013-03-19 | 2014-09-25 | Merck Sharp & Dohme Corp. | Geminally substituted cyanoethylpyrazolo pyridones as janus kinase inhibitors |
| EA201591881A1 (ru) * | 2013-03-28 | 2016-04-29 | Такеда Фармасьютикал Компани Лимитед | Гетероциклическое соединение |
| WO2014172639A1 (en) * | 2013-04-19 | 2014-10-23 | Ruga Corporation | Raf kinase inhibitors |
| WO2014186706A1 (en) * | 2013-05-17 | 2014-11-20 | Incyte Corporation | Bipyrazole derivatives as jak inhibitors |
| MX394928B (es) | 2013-08-07 | 2025-03-24 | Incyte Holdings Corp | Formas de dosificacion de liberacion prolongada para un inhibidor de jak 1 (cinasa de janus 1). |
| DK3068776T3 (da) | 2013-11-13 | 2019-07-29 | Vertex Pharma | Inhibitorer af replikation af influenzavira |
| ES2684755T3 (es) | 2013-11-13 | 2018-10-04 | Vertex Pharmaceuticals Incorporated | Métodos para preparar inhibidores de la replicación de virus de la gripe |
| US9498467B2 (en) | 2014-05-30 | 2016-11-22 | Incyte Corporation | Treatment of chronic neutrophilic leukemia (CNL) and atypical chronic myeloid leukemia (aCML) by inhibitors of JAK1 |
| US10155727B2 (en) | 2014-08-15 | 2018-12-18 | Janssen Pharmaceuticals, Inc. | Pyrazoles |
| HUE054371T2 (hu) * | 2014-12-05 | 2021-09-28 | Array Biopharma Inc | 4,6-szubsztituált pirazolo[l,5-A]pirazinok mint janus kináz inhibitorok |
| CN105777754B (zh) * | 2014-12-16 | 2019-07-26 | 北京赛林泰医药技术有限公司 | 吡咯并嘧啶化合物 |
| HUE064003T2 (hu) | 2015-01-20 | 2024-02-28 | Wuxi Fortune Pharmaceutical Co Ltd | JAK-gátló |
| JP6600365B2 (ja) | 2015-04-29 | 2019-10-30 | 无▲錫▼福祈制▲薬▼有限公司 | Ｊａｋ阻害剤 |
| WO2016183116A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| WO2016183120A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| UA118822C2 (uk) | 2015-05-29 | 2019-03-11 | Вуксі Фортуне Фармасьютікал Ко., Лтд | Інгібітор янус-кінази |
| AR104918A1 (es) * | 2015-06-19 | 2017-08-23 | Lilly Co Eli | Procesos e intermediarios para la preparación de {1-(etilsulfonil)-3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il]azetidin-3-il}acetonitrilo |
| CN105294699B (zh) * | 2015-12-04 | 2019-06-11 | 上海勋和医药科技有限公司 | 巴瑞替尼的制备方法 |
| JP6770580B2 (ja) * | 2016-01-26 | 2020-10-14 | 杭州華東医薬集団生物医薬有限公司Ｈａｎｇｚｈｏｕ Ｈｕａｄｏｎｇ Ｍｅｄｉｃｉｎｅ Ｇｒｏｕｐ Ｂｉｏｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．， Ｌｔｄ． | ピロロピリミジン５員環アザ環状誘導体およびその利用 |
| AU2017222417B2 (en) * | 2016-02-24 | 2020-07-09 | Pfizer Inc. | Pyrazolo[1,5-a]pyrazin-4-yl derivatives as JAK-inhibitors |
| CA3055233C (en) | 2017-01-23 | 2022-08-09 | Shanghai Longwood Biopharmaceuticals Co., Ltd. | Jak kinase inhibitor and preparation method and use thereof |
| WO2018167283A1 (en) | 2017-03-17 | 2018-09-20 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the diagnosis and treatment of pancreatic ductal adenocarcinoma associated neural remodeling |
| US20200088732A1 (en) | 2017-04-13 | 2020-03-19 | INSERM (Institut National de la Santé et de la Recherche Mèdicale) | Methods for the diagnosis and treatment of pancreatic ductal adenocarcinoma |
| EP3666770A4 (en) | 2017-08-07 | 2021-04-07 | Joint Stock Company "Biocad" | NEW HETEROCYCLIC COMPOUNDS AS CDK8 / 19 INHIBITORS |
| EP3668858A1 (en) | 2017-08-14 | 2020-06-24 | Pfizer Inc | Pyrazolo[1,5-a]pyrazin-4-yl and related derivatives |
| AR113922A1 (es) | 2017-12-08 | 2020-07-01 | Incyte Corp | Terapia de combinación de dosis baja para el tratamiento de neoplasias mieloproliferativas |
| WO2019152374A1 (en) | 2018-01-30 | 2019-08-08 | Incyte Corporation | Processes for preparing (1 -(3-fluoro-2-(trifluoromethyl)isonicotinyl)piperidine-4-one) |
| WO2019161098A1 (en) | 2018-02-16 | 2019-08-22 | Incyte Corporation | Jak1 pathway inhibitors for the treatment of cytokine-related disorders |
| HUE067471T2 (hu) | 2018-03-30 | 2024-10-28 | Incyte Corp | Gennyes verejtékmirigy-gyulladás kezelése jak inhibitorok alkalmazásával |
| JP2022503932A (ja) * | 2018-09-27 | 2022-01-12 | フォチョン・ファーマシューティカルズ・リミテッド | Ｒｅｔキナーゼ阻害剤としての置換イミダゾ［１，２－ａ］ピリジン及び［１，２，４］トリアゾロ［１，５－ａ］ピリジン化合物 |
| US11071730B2 (en) | 2018-10-31 | 2021-07-27 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds |
| US11203591B2 (en) | 2018-10-31 | 2021-12-21 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds |
| WO2020092015A1 (en) | 2018-11-02 | 2020-05-07 | University Of Rochester | Therapeutic mitigation of epithelial infection |
| CN111320624B (zh) * | 2018-12-14 | 2023-05-12 | 中国医药研究开发中心有限公司 | 三唑并吡啶类和咪唑并吡啶类化合物及其制备方法和医药用途 |
| MX2021012487A (es) * | 2019-04-12 | 2021-11-12 | Primegene Beijing Co Ltd | Compuestos derivados de pirazolopirazina, composicion farmaceutica y uso de la misma. |
| WO2020237025A1 (en) | 2019-05-23 | 2020-11-26 | Gilead Sciences, Inc. | Substituted exo-methylene-oxindoles which are hpk1/map4k1 inhibitors |
| CN111039963B (zh) * | 2019-12-31 | 2021-03-19 | 卓和药业集团有限公司 | Wxfl10203614水溶性类似物及其合成方法 |
| JP2023528868A (ja) | 2020-06-02 | 2023-07-06 | インサイト・コーポレイション | Ｊａｋ１阻害剤の調製プロセス |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| EP3944859A1 (en) | 2020-07-30 | 2022-02-02 | Assistance Publique Hôpitaux de Paris | Method for treating immune toxicities induced by immune checkpoint inhibitors |
| JP2023552452A (ja) | 2020-12-08 | 2023-12-15 | インサイト・コーポレイション | 白斑治療用のｊａｋ１経路阻害薬 |
| US12268667B2 (en) | 2021-05-03 | 2025-04-08 | Incyte Corporation | JAK1 pathway inhibitors for the treatment of prurigo nodularis |
| CA3237632A1 (en) * | 2021-11-12 | 2023-05-19 | Changqing WEI | Pyrazolo fused ring compound and use thereof |
| CA3250151A1 (en) * | 2022-04-25 | 2023-11-02 | Eli Lilly And Company | FGFR2 INHIBITOR COMPOUNDS |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5728536A (en) | 1993-07-29 | 1998-03-17 | St. Jude Children's Research Hospital | Jak kinases and regulation of Cytokine signal transduction |
| EP1105378B1 (en) | 1998-08-21 | 2005-03-30 | Parker Hughes Institute | Quinazoline derivatives |
| JP2001302667A (ja) * | 2000-04-28 | 2001-10-31 | Bayer Ag | イミダゾピリミジン誘導体およびトリアゾロピリミジン誘導体 |
| US7713973B2 (en) * | 2004-10-15 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| PT1966202E (pt) * | 2005-12-13 | 2012-01-03 | Incyte Corp | Pirrolo[2,3-b] pirimidinas e pirrolo[2,3-b]piridinas substituídas com heteroarilo como inibidores de janus quinase |
| EP2497470B8 (en) | 2006-11-22 | 2015-12-02 | Incyte Holdings Corporation | Imidazotriazines and imidazopyrimidines as kinase inhibitors |
| DE102007012645A1 (de) * | 2007-03-16 | 2008-09-18 | Bayer Healthcare Ag | Substituierte Imidazo- und Triazolopyrimidine |
| CL2008001709A1 (es) * | 2007-06-13 | 2008-11-03 | Incyte Corp | Compuestos derivados de pirrolo [2,3-b]pirimidina, moduladores de quinasas jak; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como cancer, psoriasis, artritis reumatoide, entre otras. |
| BRPI0909040B8 (pt) | 2008-03-11 | 2021-05-25 | Incyte Holdings Corp | derivados de azetidina e ciclobutano, seus usos, e composição |
| JOP20190231A1 (ar) | 2009-01-15 | 2017-06-16 | Incyte Corp | طرق لاصلاح مثبطات انزيم jak و المركبات الوسيطة المتعلقة به |
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2011
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- 2011-04-11 CN CN201180029128.5A patent/CN102985424B/zh not_active Expired - Fee Related
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