JP2017531672A5 - - Google Patents
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- JP2017531672A5 JP2017531672A5 JP2017521567A JP2017521567A JP2017531672A5 JP 2017531672 A5 JP2017531672 A5 JP 2017531672A5 JP 2017521567 A JP2017521567 A JP 2017521567A JP 2017521567 A JP2017521567 A JP 2017521567A JP 2017531672 A5 JP2017531672 A5 JP 2017531672A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- tert
- butyl
- carboxylate
- pyridin
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 58
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 46
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 23
- -1 morpholinylcarbonyl Chemical group 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 208000006673 asthma Diseases 0.000 claims 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 8
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 claims 3
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 3
- 230000001668 ameliorated effect Effects 0.000 claims 3
- 206010003246 arthritis Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 230000005764 inhibitory process Effects 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- AQCRZGMLYVPHJE-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-(1,4-oxazepane-4-carbonyl)anilino]-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1NC(Nc2ccc(C(=O)N3CCCOCC3)c(C)c2)C2C1CCNC2=O AQCRZGMLYVPHJE-UHFFFAOYSA-N 0.000 claims 2
- VPEYITDXALJWIP-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-(1,4-thiazepane-4-carbonyl)anilino]-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1NC(Nc2ccc(C(=O)N3CCCSCC3)c(C)c2)C2C1CCNC2=O VPEYITDXALJWIP-UHFFFAOYSA-N 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- 208000000884 Airway Obstruction Diseases 0.000 claims 1
- DTRJMDAVHUVYAE-UHFFFAOYSA-N C(C)(C)(C)NC(C(F)(F)F)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC Chemical compound C(C)(C)(C)NC(C(F)(F)F)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC DTRJMDAVHUVYAE-UHFFFAOYSA-N 0.000 claims 1
- QYHXGVWXCTYPJI-UHFFFAOYSA-N C(C)(C)(C)OC(=O)N1CCC(CC1)(CC)N1N=C(C=2C(NC=CC=21)=O)NC1=CC(=C(C(=O)O)C=C1)C Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)(CC)N1N=C(C=2C(NC=CC=21)=O)NC1=CC(=C(C(=O)O)C=C1)C QYHXGVWXCTYPJI-UHFFFAOYSA-N 0.000 claims 1
- HCUJMXUNTUJCQO-UHFFFAOYSA-N CC1C(N(CCO1)C(=O)C1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)C)C Chemical compound CC1C(N(CCO1)C(=O)C1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)C)C HCUJMXUNTUJCQO-UHFFFAOYSA-N 0.000 claims 1
- ZZESVEZOCNMYKO-UHFFFAOYSA-N CC1N(C(COC1)C)C(=O)C1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)C Chemical compound CC1N(C(COC1)C)C(=O)C1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)C ZZESVEZOCNMYKO-UHFFFAOYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 102000042838 JAK family Human genes 0.000 claims 1
- 108091082332 JAK family Proteins 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000020410 Psoriasis-related juvenile idiopathic arthritis Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 201000009961 allergic asthma Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 208000023819 chronic asthma Diseases 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000428 dust Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000024711 extrinsic asthma Diseases 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 230000009610 hypersensitivity Effects 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 201000010659 intrinsic asthma Diseases 0.000 claims 1
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- VCZVQTITSMRSGI-UHFFFAOYSA-N tert-butyl 4-[3-[(2-tert-butyl-1,1-dioxo-3H-1,2-benzothiazol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1N=C(NC2=CC3=C(C=C2)S(=O)(=O)N(C3)C(C)(C)C)C2=C1C=CNC2=O VCZVQTITSMRSGI-UHFFFAOYSA-N 0.000 claims 1
- OVMSVEDTZIBSSS-UHFFFAOYSA-N tert-butyl 4-[3-[3-(cyanomethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound C(#N)CC=1C=C(C=CC=1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC OVMSVEDTZIBSSS-UHFFFAOYSA-N 0.000 claims 1
- UJYBRGPHKIPGOP-UHFFFAOYSA-N tert-butyl 4-[3-[3-(difluoromethyl)-4-(thiomorpholine-4-carbonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound FC(C=1C=C(C=CC=1C(=O)N1CCSCC1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)F UJYBRGPHKIPGOP-UHFFFAOYSA-N 0.000 claims 1
- MQIVXAPBLCFOLV-UHFFFAOYSA-N tert-butyl 4-[3-[4-(3,3-dimethylmorpholine-4-carbonyl)-3-methylanilino]-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1NC(Nc2ccc(C(=O)N3CCOCC3(C)C)c(C)c2)C2C1CCNC2=O MQIVXAPBLCFOLV-UHFFFAOYSA-N 0.000 claims 1
- IBXSTINXLIQXHQ-UHFFFAOYSA-N tert-butyl 4-[3-[4-(4,4-difluoropiperidine-1-carbonyl)-3-methylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound FC1(CCN(CC1)C(=O)C1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)C)F IBXSTINXLIQXHQ-UHFFFAOYSA-N 0.000 claims 1
- XBTDFAVREZFIFS-UHFFFAOYSA-N tert-butyl 4-[3-[4-(dimethylsulfamoyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound CN(S(=O)(=O)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)C XBTDFAVREZFIFS-UHFFFAOYSA-N 0.000 claims 1
- DTRJMDAVHUVYAE-HSZRJFAPSA-N tert-butyl 4-[3-[4-[(1R)-1-(tert-butylamino)-2,2,2-trifluoroethyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound C(C)(C)(C)N[C@@H](C(F)(F)F)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC DTRJMDAVHUVYAE-HSZRJFAPSA-N 0.000 claims 1
- DTRJMDAVHUVYAE-QHCPKHFHSA-N tert-butyl 4-[3-[4-[(1S)-1-(tert-butylamino)-2,2,2-trifluoroethyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound C(C)(C)(C)N[C@H](C(F)(F)F)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC DTRJMDAVHUVYAE-QHCPKHFHSA-N 0.000 claims 1
- VCIDUKMABVZQBK-MZZLKFDNSA-N tert-butyl 4-[3-[4-[(2R,6S)-2,6-dimethylmorpholine-4-carbonyl]-3-methylanilino]-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1NC(Nc2ccc(C(=O)N3C[C@H](C)O[C@H](C)C3)c(C)c2)C2C1CCNC2=O VCIDUKMABVZQBK-MZZLKFDNSA-N 0.000 claims 1
- VCIDUKMABVZQBK-ZYRNILTFSA-N tert-butyl 4-[3-[4-[(2S,6S)-2,6-dimethylmorpholine-4-carbonyl]-3-methylanilino]-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1NC(Nc2ccc(C(=O)N3C[C@H](C)O[C@@H](C)C3)c(C)c2)C2C1CCNC2=O VCIDUKMABVZQBK-ZYRNILTFSA-N 0.000 claims 1
- ZZESVEZOCNMYKO-FGZHOGPDSA-N tert-butyl 4-[3-[4-[(3R,5R)-3,5-dimethylmorpholine-4-carbonyl]-3-methylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound C[C@H]1N([C@@H](COC1)C)C(=O)C1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)C ZZESVEZOCNMYKO-FGZHOGPDSA-N 0.000 claims 1
- ZZESVEZOCNMYKO-SZPZYZBQSA-N tert-butyl 4-[3-[4-[(3S,5R)-3,5-dimethylmorpholine-4-carbonyl]-3-methylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1N=C(NC2=CC=C(C(=O)N3[C@@H](C)COC[C@H]3C)C(C)=C2)C2=C1C=CNC2=O ZZESVEZOCNMYKO-SZPZYZBQSA-N 0.000 claims 1
- ZZESVEZOCNMYKO-VXKWHMMOSA-N tert-butyl 4-[3-[4-[(3S,5S)-3,5-dimethylmorpholine-4-carbonyl]-3-methylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound C[C@@H]1N([C@H](COC1)C)C(=O)C1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)C ZZESVEZOCNMYKO-VXKWHMMOSA-N 0.000 claims 1
- AJYAJOWIKLAPEZ-UHFFFAOYSA-N tert-butyl 4-[3-[[2-(4,4-difluoro-1-methylcyclohexyl)-1-oxo-3H-isoindol-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound FC1(CCC(CC1)(C)N1C(C2=CC=C(C=C2C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)=O)F AJYAJOWIKLAPEZ-UHFFFAOYSA-N 0.000 claims 1
- VRWJMTDFUJOLKU-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-ethyl-4-(morpholine-4-carbonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C(C)C1(CCN(CC1)C(=O)OC(C)(C)C)N1N=C(C=2C(NC=CC=21)=O)NC1=CC(=C(C=C1)C(=O)N1CCOCC1)CC VRWJMTDFUJOLKU-UHFFFAOYSA-N 0.000 claims 1
- UOAGZDRBAXUGTD-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-fluoro-4-(morpholine-4-carbonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C(C)C1(CCN(CC1)C(=O)OC(C)(C)C)N1N=C(C=2C(NC=CC=21)=O)NC1=CC(=C(C=C1)C(=O)N1CCOCC1)F UOAGZDRBAXUGTD-UHFFFAOYSA-N 0.000 claims 1
- FKLIUQABHHPDSC-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-(2-oxa-5-azabicyclo[4.1.0]heptane-5-carbonyl)anilino]-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1NC(Nc2ccc(C(=O)N3CCOC4CC34)c(C)c2)C2C1CCNC2=O FKLIUQABHHPDSC-UHFFFAOYSA-N 0.000 claims 1
- JCRNVEAIVFJQIC-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-(2-oxomorpholine-4-carbonyl)phenyl]imino-4-oxo-2,3a-dihydropyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1N\C(=N/c2ccc(C(=O)N3CCOC(=O)C3)c(C)c2)C2C1=CC=NC2=O JCRNVEAIVFJQIC-UHFFFAOYSA-N 0.000 claims 1
- VULKABYBBCMRDJ-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-(3-oxa-8-azabicyclo[3.2.1]octane-8-carbonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C12COCC(CC1)N2C(=O)C1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)C VULKABYBBCMRDJ-UHFFFAOYSA-N 0.000 claims 1
- CJWLOOHFRAPWQZ-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-(4-thiomorpholin-4-ylpiperidine-1-carbonyl)anilino]-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1NC(Nc2ccc(C(=O)N3CCC(CC3)N3CCSCC3)c(C)c2)C2C1CCNC2=O CJWLOOHFRAPWQZ-UHFFFAOYSA-N 0.000 claims 1
- VBNOMIJWDQGIST-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-(6-oxa-3-azabicyclo[3.1.1]heptane-3-carbonyl)anilino]-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1NC(Nc2ccc(C(=O)N3CC4CC(C3)O4)c(C)c2)C2C1CCNC2=O VBNOMIJWDQGIST-UHFFFAOYSA-N 0.000 claims 1
- UFJYEMKQRJJTSP-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-(6-oxa-9-azaspiro[4.5]decane-9-carbonyl)anilino]-4-oxo-3,3a,5,6,7,7a-hexahydro-2H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound CCC1(CCN(CC1)C(=O)OC(C)(C)C)N1NC(Nc2ccc(C(=O)N3CCOC4(CCCC4)C3)c(C)c2)C2C1CCNC2=O UFJYEMKQRJJTSP-UHFFFAOYSA-N 0.000 claims 1
- XTOJHQAKCRPBFI-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octane-3-carbonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C12CN(CC(CC1)O2)C(=O)C1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)C XTOJHQAKCRPBFI-UHFFFAOYSA-N 0.000 claims 1
- VBQKXAAABIIWAA-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-(morpholine-4-carbonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C(C)C1(CCN(CC1)C(=O)OC(C)(C)C)N1N=C(C=2C(NC=CC=21)=O)NC1=CC(=C(C=C1)C(=O)N1CCOCC1)C VBQKXAAABIIWAA-UHFFFAOYSA-N 0.000 claims 1
- AROXZIHWXGMKHB-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-(thiomorpholine-4-carbonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C(C)C1(CCN(CC1)C(=O)OC(C)(C)C)N1N=C(C=2C(NC=CC=21)=O)NC1=CC(=C(C=C1)C(=O)N1CCSCC1)C AROXZIHWXGMKHB-UHFFFAOYSA-N 0.000 claims 1
- XKLMPWQCHSGFNF-FGZHOGPDSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-[(1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptane-5-carbonyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound [C@H]12OC[C@H](N(C1)C(=O)C1=C(C=C(C=C1)NC1=NN(C3=C1C(NC=C3)=O)C1(CCN(CC1)C(=O)OC(C)(C)C)CC)C)C2 XKLMPWQCHSGFNF-FGZHOGPDSA-N 0.000 claims 1
- XKLMPWQCHSGFNF-VXKWHMMOSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane-5-carbonyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)(CC)N1N=C(C=2C(NC=CC=21)=O)NC1=CC(=C(C=C1)C(=O)N1[C@@H]2CO[C@H](C1)C2)C XKLMPWQCHSGFNF-VXKWHMMOSA-N 0.000 claims 1
- MIXUUNJGYMRPJW-OAQYLSRUSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-[(2R)-2-methylmorpholine-4-carbonyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)(N1N=C(C=2C(NC=CC=21)=O)NC1=CC(=C(C=C1)C(=O)N1C[C@H](OCC1)C)C)CC MIXUUNJGYMRPJW-OAQYLSRUSA-N 0.000 claims 1
- LTCPXQDINYBYHF-OAQYLSRUSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-[(3R)-3-methylmorpholine-4-carbonyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)(N1N=C(C=2C(NC=CC=21)=O)NC1=CC(=C(C=C1)C(=O)N1[C@@H](COCC1)C)C)CC LTCPXQDINYBYHF-OAQYLSRUSA-N 0.000 claims 1
- LTCPXQDINYBYHF-NRFANRHFSA-N tert-butyl 4-ethyl-4-[3-[3-methyl-4-[(3S)-3-methylmorpholine-4-carbonyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C(C)C1(CCN(CC1)C(=O)OC(C)(C)C)N1N=C(C=2C(NC=CC=21)=O)NC1=CC(=C(C=C1)C(=O)N1[C@H](COCC1)C)C LTCPXQDINYBYHF-NRFANRHFSA-N 0.000 claims 1
- BWISHMDVCOHCAS-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[3-[[2-(oxan-4-yl)-1,1-dioxo-3H-1,2-benzothiazol-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C(C)C1(CCN(CC1)C(=O)OC(C)(C)C)N1N=C(C=2C(NC=CC=21)=O)NC=1C=CC2=C(CN(S2(=O)=O)C2CCOCC2)C=1 BWISHMDVCOHCAS-UHFFFAOYSA-N 0.000 claims 1
- IOMXYGDCDPKFOJ-UHFFFAOYSA-N tert-butyl 4-ethyl-4-[4-oxo-3-(4-piperidin-4-ylanilino)-5H-pyrazolo[4,3-c]pyridin-1-yl]piperidine-1-carboxylate Chemical compound C(C)C1(CCN(CC1)C(=O)OC(C)(C)C)N1N=C(C=2C(NC=CC=21)=O)NC1=CC=C(C=C1)C1CCNCC1 IOMXYGDCDPKFOJ-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
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|---|---|---|---|
| CNPCT/CN2014/089139 | 2014-10-22 | ||
| PCT/CN2014/089139 WO2016061751A1 (en) | 2014-10-22 | 2014-10-22 | Ethyl n-boc piperidinyl pyrazolo pyridones as janus kinase inhibitors |
| PCT/US2015/056541 WO2016064935A1 (en) | 2014-10-22 | 2015-10-21 | Ethyl n-boc piperidinyl pyrazolo pyridones as janus kinase inhibitors |
Publications (2)
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| JP2017531672A JP2017531672A (ja) | 2017-10-26 |
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| EP (1) | EP3209296B1 (enExample) |
| JP (1) | JP2017531672A (enExample) |
| KR (1) | KR20170068585A (enExample) |
| CN (1) | CN107106547A (enExample) |
| AU (1) | AU2015336035A1 (enExample) |
| BR (1) | BR112017008103A2 (enExample) |
| CA (1) | CA2964375A1 (enExample) |
| MX (1) | MX2017005281A (enExample) |
| RU (1) | RU2017117248A (enExample) |
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| JP7034942B2 (ja) | 2016-05-05 | 2022-03-14 | エフ．ホフマン－ラ ロシュ アーゲー | ピラゾール誘導体、その組成物及び治療的使用 |
| CN106749081B (zh) * | 2016-11-21 | 2019-06-25 | 浙江嘉圣生物医药有限公司 | 一种(s)-(4-溴-2-甲苯)(3-甲基吗啉)甲酮的制备方法 |
| US10040804B2 (en) | 2016-12-21 | 2018-08-07 | Biotheryx, Inc. | Compounds targeting proteins, compositions, methods, and uses thereof |
| US10406165B2 (en) | 2017-03-14 | 2019-09-10 | Biotheryx, Inc. | Compounds targeting proteins, compositions, methods, and uses thereof |
| JP7085641B2 (ja) | 2017-12-22 | 2022-06-16 | ジークフリート アクチェンゲゼルシャフト | アルコラート塩基の存在下でのニコチン酸エチルとｎ－ビニルピロリドンとの反応によるラセミ体ニコチンの調製方法 |
| WO2019214399A1 (zh) * | 2018-05-10 | 2019-11-14 | 罗欣药业(上海)有限公司 | 苯并七元杂环类化合物、其制备方法、药物组合物及应用 |
| US20210395239A1 (en) * | 2018-09-27 | 2021-12-23 | Hoffmann-La Roche Inc. | Heterocyclyl compounds for the treatment of autoimmune disease |
| US11697648B2 (en) | 2019-11-26 | 2023-07-11 | Theravance Biopharma R&D Ip, Llc | Fused pyrimidine pyridinone compounds as JAK inhibitors |
| WO2021170046A1 (en) * | 2020-02-26 | 2021-09-02 | Beigene, Ltd. | Tyk-2 inhibitor |
| EP4263535A1 (en) * | 2020-12-17 | 2023-10-25 | Astrazeneca AB | N-(2-(4-cyanothiazolidin-3-yl)-2-oxoethyl)- quinoline-4-carboxamides |
| CN114644633B (zh) * | 2020-12-18 | 2026-02-03 | 北京诺诚健华医药科技有限公司 | 杂环类jak抑制剂 |
| CN114939349B (zh) * | 2022-05-03 | 2023-08-01 | 北京工业大学 | 一种用于气体分离的金属-有机空穴配合物混合基质膜的制备 |
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| UA111854C2 (uk) * | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| JP6305510B2 (ja) * | 2013-03-19 | 2018-04-04 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | ヤヌスキナーゼ阻害剤としての非環式シアノエチルピラゾロピリドン |
| WO2014146249A1 (en) * | 2013-03-19 | 2014-09-25 | Merck Sharp & Dohme Corp. | Geminally substituted cyanoethylpyrazolo pyridones as janus kinase inhibitors |
| WO2014146492A1 (en) * | 2013-03-19 | 2014-09-25 | Merck Sharp & Dohme Corp. | N-(2-cyano heterocyclyl)pyrazolo pyridones as janus kinase inhibitors |
-
2014
- 2014-10-22 WO PCT/CN2014/089139 patent/WO2016061751A1/en not_active Ceased
-
2015
- 2015-10-21 KR KR1020177013258A patent/KR20170068585A/ko not_active Withdrawn
- 2015-10-21 JP JP2017521567A patent/JP2017531672A/ja not_active Withdrawn
- 2015-10-21 CA CA2964375A patent/CA2964375A1/en not_active Abandoned
- 2015-10-21 CN CN201580070401.7A patent/CN107106547A/zh active Pending
- 2015-10-21 US US15/519,740 patent/US10072025B2/en active Active
- 2015-10-21 BR BR112017008103A patent/BR112017008103A2/pt not_active Application Discontinuation
- 2015-10-21 RU RU2017117248A patent/RU2017117248A/ru not_active Application Discontinuation
- 2015-10-21 AU AU2015336035A patent/AU2015336035A1/en not_active Abandoned
- 2015-10-21 EP EP15853280.4A patent/EP3209296B1/en active Active
- 2015-10-21 WO PCT/US2015/056541 patent/WO2016064935A1/en not_active Ceased
- 2015-10-21 MX MX2017005281A patent/MX2017005281A/es unknown
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