RU2015144385A - Ациклические цианоэтилпиразолопиридоны в качестве ингибиторов янус-киназы - Google Patents
Ациклические цианоэтилпиразолопиридоны в качестве ингибиторов янус-киназы Download PDFInfo
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- RU2015144385A RU2015144385A RU2015144385A RU2015144385A RU2015144385A RU 2015144385 A RU2015144385 A RU 2015144385A RU 2015144385 A RU2015144385 A RU 2015144385A RU 2015144385 A RU2015144385 A RU 2015144385A RU 2015144385 A RU2015144385 A RU 2015144385A
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- dihydro
- oxo
- pyrazolo
- amino
- pyridin
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- -1 Acyclic cyanoethylpyrazolopyridones Chemical class 0.000 title claims 64
- 229940122245 Janus kinase inhibitor Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 74
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 238000000034 method Methods 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 208000006673 asthma Diseases 0.000 claims 8
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 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
- 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 claims 3
- 206010003246 arthritis Diseases 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 2
- YTKKUWMLXHAVOP-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[(1,1-dioxospiro[3H-1-benzothiophene-2,1'-cyclohexane]-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound C1(CC1)C(CC#N)N1N=C(C=2C(NC=CC21)=O)NC2=CC1=C(S(C3(C1)CCCCC3)(=O)=O)C=C2 YTKKUWMLXHAVOP-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- 230000000414 obstructive effect Effects 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 239000010802 sludge Substances 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000001544 thienyl 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
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- PUJCTTRZKKGKHG-UHFFFAOYSA-N 2-[3-(4-tert-butylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound C(C)(C)(C)S(=O)(=O)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C(C#N)CC2CC2 PUJCTTRZKKGKHG-UHFFFAOYSA-N 0.000 claims 1
- JWKBQSYOGDEYIF-UHFFFAOYSA-N 2-cyclopropyl-3-[4-oxo-3-(4-propan-2-ylsulfonylanilino)-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound C1(CC1)C(C#N)CN1N=C(C=2C(NC=CC=21)=O)NC1=CC=C(C=C1)S(=O)(=O)C(C)C JWKBQSYOGDEYIF-UHFFFAOYSA-N 0.000 claims 1
- LZENBEADSYVOQL-UHFFFAOYSA-N 3-[3-(1,3-benzodioxol-5-ylamino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound O1COC2=C1C=CC(=C2)NC2=NN(C1=C2C(NC=C1)=O)C(CC#N)C1CC1 LZENBEADSYVOQL-UHFFFAOYSA-N 0.000 claims 1
- YCAZAQPLKSEBCX-UHFFFAOYSA-N 3-[3-(1,3-benzodioxol-5-ylamino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CC(CC#N)n1nc(Nc2ccc3OCOc3c2)c2c1cc[nH]c2=O YCAZAQPLKSEBCX-UHFFFAOYSA-N 0.000 claims 1
- QIQVCJYVNYITSC-UHFFFAOYSA-N 3-[3-(2,3-dihydro-1-benzofuran-5-ylamino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CC(CC#N)n1nc(Nc2ccc3OCCc3c2)c2c1cc[nH]c2=O QIQVCJYVNYITSC-UHFFFAOYSA-N 0.000 claims 1
- MPXSGJUPTRUVQH-UHFFFAOYSA-N 3-[3-(3-fluoro-4-methylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CC(CC#N)n1nc(Nc2ccc(c(F)c2)S(C)(=O)=O)c2c1cc[nH]c2=O MPXSGJUPTRUVQH-UHFFFAOYSA-N 0.000 claims 1
- DYHROIXUDZRNNM-UHFFFAOYSA-N 3-[3-(4-chloroanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound Clc1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1 DYHROIXUDZRNNM-UHFFFAOYSA-N 0.000 claims 1
- FMCARZFTQXFHQD-UHFFFAOYSA-N 3-[3-(4-chloroanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CC(CC#N)n1nc(Nc2ccc(Cl)cc2)c2c1cc[nH]c2=O FMCARZFTQXFHQD-UHFFFAOYSA-N 0.000 claims 1
- TXVFVSLOZYUJKZ-UHFFFAOYSA-N 3-[3-(4-fluoroanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CC(CC#N)n1nc(Nc2ccc(F)cc2)c2c1cc[nH]c2=O TXVFVSLOZYUJKZ-UHFFFAOYSA-N 0.000 claims 1
- MGLOSMDWIOJCOJ-UHFFFAOYSA-N 3-[3-(4-methylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CS(=O)(=O)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C(CC#N)C MGLOSMDWIOJCOJ-UHFFFAOYSA-N 0.000 claims 1
- YVWVPBDKGWAOGI-UHFFFAOYSA-N 3-[3-[(1,1-dioxo-2,3-dihydro-1-benzothiophen-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CC(CC#N)n1nc(Nc2ccc3c(CCS3(=O)=O)c2)c2c1cc[nH]c2=O YVWVPBDKGWAOGI-UHFFFAOYSA-N 0.000 claims 1
- LUDBODPGAPKSSG-UHFFFAOYSA-N 3-[3-[(2-benzyl-1,1-dioxo-3H-1,2-benzothiazol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound O=C1NC=CC2=C1C(NC1=CC3=C(C=C1)S(=O)(=O)N(CC1=CC=CC=C1)C3)=NN2C(CC#N)C1CC1 LUDBODPGAPKSSG-UHFFFAOYSA-N 0.000 claims 1
- JHYAEMZTZKEJFR-UHFFFAOYSA-N 3-[3-[(2-cyclohexyl-1,1-dioxo-3H-1,2-benzothiazol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound O=C1NC=CC2=C1C(NC1=CC3=C(C=C1)S(=O)(=O)N(C3)C1CCCCC1)=NN2C(CC#N)C1CC1 JHYAEMZTZKEJFR-UHFFFAOYSA-N 0.000 claims 1
- ORZWYGZWIPXVQQ-UHFFFAOYSA-N 3-[3-[(2-cyclohexyl-1-oxo-3H-isoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound O=C1N(Cc2cc(Nc3nn(C(CC#N)C4CC4)c4cc[nH]c(=O)c34)ccc12)C1CCCCC1 ORZWYGZWIPXVQQ-UHFFFAOYSA-N 0.000 claims 1
- MBSKILWBEYZPSS-UHFFFAOYSA-N 3-[3-[(2-cyclopentyl-1-oxo-3H-isoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound O=C1N(Cc2cc(Nc3nn(C(CC#N)C4CC4)c4cc[nH]c(=O)c34)ccc12)C1CCCC1 MBSKILWBEYZPSS-UHFFFAOYSA-N 0.000 claims 1
- FXOCINSAVMVAEV-UHFFFAOYSA-N 3-[3-[(2-fluoropyridin-4-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CC(CC#N)n1nc(Nc2ccnc(F)c2)c2c1cc[nH]c2=O FXOCINSAVMVAEV-UHFFFAOYSA-N 0.000 claims 1
- XQDMKEQGSSOJTN-UHFFFAOYSA-N 3-[3-[(2-methyl-1,1-dioxo-3H-1,2-benzothiazol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CC(CC#N)n1nc(Nc2ccc3c(CN(C)S3(=O)=O)c2)c2c1cc[nH]c2=O XQDMKEQGSSOJTN-UHFFFAOYSA-N 0.000 claims 1
- KFAWTQCXIFRJIF-UHFFFAOYSA-N 3-[3-[(2-tert-butyl-1,1-dioxo-3H-1,2-benzothiazol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound C(C)(C)(C)N1S(C2=C(C1)C=C(C=C2)NC1=NN(C2=C1C(NC=C2)=O)C(CC#N)C1CC1)(=O)=O KFAWTQCXIFRJIF-UHFFFAOYSA-N 0.000 claims 1
- PXJDIEBDCSPYNS-UHFFFAOYSA-N 3-[3-[(2-tert-butyl-1,1-dioxo-3H-1,2-benzothiazol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound C(C)(C)(C)N1S(C2=C(C1)C=C(C=C2)NC2=NN(C1=C2C(NC=C1)=O)C(CC#N)C)(=O)=O PXJDIEBDCSPYNS-UHFFFAOYSA-N 0.000 claims 1
- KVNPGZVFMJXRBG-UHFFFAOYSA-N 3-[3-[3-chloro-4-(1-methylpyrazol-3-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound Cn1ccc(n1)-c1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1Cl KVNPGZVFMJXRBG-UHFFFAOYSA-N 0.000 claims 1
- URXBTNDUCYUJCG-UHFFFAOYSA-N 3-[3-[3-chloro-4-(2,2,2-trifluoro-1-hydroxyethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound OC(c1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1Cl)C(F)(F)F URXBTNDUCYUJCG-UHFFFAOYSA-N 0.000 claims 1
- YZEHISRDAFAIQS-UHFFFAOYSA-N 3-[3-[3-chloro-4-[1-(2-cyanoethyl)pyrazol-3-yl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound Clc1cc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)ccc1-c1ccn(CCC#N)n1 YZEHISRDAFAIQS-UHFFFAOYSA-N 0.000 claims 1
- QBAYDHLMAOYXDT-UHFFFAOYSA-N 3-[3-[4-(1-amino-2,2,2-trifluoroethyl)-3-methylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound Cc1cc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)ccc1C(N)C(F)(F)F QBAYDHLMAOYXDT-UHFFFAOYSA-N 0.000 claims 1
- DLSSATVVRBJGOD-UHFFFAOYSA-N 3-[3-[4-(1-amino-2,2,2-trifluoroethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound NC(c1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1)C(F)(F)F DLSSATVVRBJGOD-UHFFFAOYSA-N 0.000 claims 1
- QUUXUJXRRWXOBK-UHFFFAOYSA-N 3-[3-[4-(2-azaspiro[3.3]heptan-2-ylsulfonyl)-3-methylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound Cc1cc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)ccc1S(=O)(=O)N1CC2(CCC2)C1 QUUXUJXRRWXOBK-UHFFFAOYSA-N 0.000 claims 1
- WSKPORIUCCXCOR-UHFFFAOYSA-N 3-[3-[4-(3,4a,5,6,7,7a-hexahydro-2H-cyclopenta[b][1,4]oxazin-4-ylsulfonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound C1(CC1)C(CC#N)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N2C1C(OCC2)CCC1 WSKPORIUCCXCOR-UHFFFAOYSA-N 0.000 claims 1
- QMOFLCCHJKKOAI-UHFFFAOYSA-N 3-[3-[4-(azepane-1-carbonyl)-3-methylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound Cc1cc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)ccc1C(=O)N1CCCCCC1 QMOFLCCHJKKOAI-UHFFFAOYSA-N 0.000 claims 1
- MYQQFTMYYBRRKB-UHFFFAOYSA-N 3-[3-[4-(azetidin-1-ylsulfonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccc(cc3)S(=O)(=O)N3CCC3)c12)C(CC#N)C1CC1 MYQQFTMYYBRRKB-UHFFFAOYSA-N 0.000 claims 1
- LBIJRMDGIKKCLS-UHFFFAOYSA-N 3-[3-[4-(azetidin-1-ylsulfonyl)anilino]-7-(hydroxymethyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound OCc1c[nH]c(=O)c2c(Nc3ccc(cc3)S(=O)(=O)N3CCC3)nn(C(CC#N)C3CC3)c12 LBIJRMDGIKKCLS-UHFFFAOYSA-N 0.000 claims 1
- ZKLMXRYSSKJXNR-UHFFFAOYSA-N 3-[3-[4-[1-(azetidin-1-yl)-2,2,2-trifluoroethyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound FC(F)(F)C(N1CCC1)c1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1 ZKLMXRYSSKJXNR-UHFFFAOYSA-N 0.000 claims 1
- DLKIFOLPNAAMOY-UHFFFAOYSA-N 3-[3-[4-[1-(tert-butylamino)-2,2,2-trifluoroethyl]-3-chloroanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound C(C)(C)(C)NC(C(F)(F)F)C1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C(CC#N)C1CC1)Cl DLKIFOLPNAAMOY-UHFFFAOYSA-N 0.000 claims 1
- BZTPLLBKFUGABX-UHFFFAOYSA-N 3-[3-[4-[1-(tert-butylamino)-2,2,2-trifluoroethyl]-3-fluoroanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound C(C)(C)(C)NC(C(F)(F)F)C1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C(CC#N)C1CC1)F BZTPLLBKFUGABX-UHFFFAOYSA-N 0.000 claims 1
- SMTCYVIKUKDWPA-UHFFFAOYSA-N 3-[3-[4-[cyclopentyl(triazol-2-yl)methyl]-3-methylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound CC1=C(C=CC(NC2=NN(C(CC#N)C3CC3)C3=C2C(=O)NC=C3)=C1)C(C1CCCC1)N1N=CC=N1 SMTCYVIKUKDWPA-UHFFFAOYSA-N 0.000 claims 1
- JGVWCMCWOOCBLQ-UHFFFAOYSA-N 3-[3-[[1-hydroxy-1-(trifluoromethyl)-2,3-dihydroinden-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound OC1(CCC2=CC(=CC=C12)NC1=NN(C2=C1C(NC=C2)=O)C(CC#N)C)C(F)(F)F JGVWCMCWOOCBLQ-UHFFFAOYSA-N 0.000 claims 1
- IXBZTRNBWJYVGI-UHFFFAOYSA-N 3-[4-oxo-3-(3,4,5-trifluoroanilino)-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CC(CC#N)n1nc(Nc2cc(F)c(F)c(F)c2)c2c1cc[nH]c2=O IXBZTRNBWJYVGI-UHFFFAOYSA-N 0.000 claims 1
- SKGUBSPPXCKWSP-UHFFFAOYSA-N 3-[4-oxo-3-(quinolin-6-ylamino)-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound O=C1NC=CC2=C1C(=NN2C(CC#N)C)NC=2C=C1C=CC=NC1=CC2 SKGUBSPPXCKWSP-UHFFFAOYSA-N 0.000 claims 1
- CCJYPQWXAGEKAJ-UHFFFAOYSA-N 3-[4-oxo-3-(quinoxalin-6-ylamino)-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CC(CC#N)n1nc(Nc2ccc3nccnc3c2)c2c1cc[nH]c2=O CCJYPQWXAGEKAJ-UHFFFAOYSA-N 0.000 claims 1
- XDGLXLXPPCJMJF-UHFFFAOYSA-N 3-[4-oxo-3-[(1-oxo-2,3-dihydroinden-5-yl)amino]-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound CC(CC#N)n1nc(Nc2ccc3C(=O)CCc3c2)c2c1cc[nH]c2=O XDGLXLXPPCJMJF-UHFFFAOYSA-N 0.000 claims 1
- AEIBLQPBOBHCOV-UHFFFAOYSA-N 3-[4-oxo-3-[4-(trifluoromethyl)anilino]-5H-pyrazolo[4,3-c]pyridin-1-yl]butanenitrile Chemical compound O=C1NC=CC2=C1C(=NN2C(CC#N)C)NC1=CC=C(C=C1)C(F)(F)F AEIBLQPBOBHCOV-UHFFFAOYSA-N 0.000 claims 1
- PXJHCFJRDTVWPX-UHFFFAOYSA-N 3-cyclobutyl-3-[4-oxo-3-(4-pyrrolidin-1-ylsulfonylanilino)-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccc(cc3)S(=O)(=O)N3CCCC3)c12)C(CC#N)C1CCC1 PXJHCFJRDTVWPX-UHFFFAOYSA-N 0.000 claims 1
- XJNFIOGKNBIWRQ-UHFFFAOYSA-N 3-cyclopropyl-3-[3-(2,3-dihydro-1-benzofuran-5-ylamino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound C1(CC1)C(CC#N)N1N=C(C=2C(NC=CC=21)=O)NC=1C=CC2=C(CCO2)C=1 XJNFIOGKNBIWRQ-UHFFFAOYSA-N 0.000 claims 1
- PWLBDDXNPCYIFF-UHFFFAOYSA-N 3-cyclopropyl-3-[3-(3-methyl-4-pyrrolidin-1-ylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound C1(CC1)C(CC#N)N1N=C(C=2C(NC=CC21)=O)NC2=CC(=C(C=C2)S(=O)(=O)N2CCCC2)C PWLBDDXNPCYIFF-UHFFFAOYSA-N 0.000 claims 1
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- DAPPJWVDRCNIOP-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[4-[1-(ethylamino)-2,2,2-trifluoroethyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound C1(CC1)C(CC#N)N1N=C(C=2C(NC=CC=21)=O)NC1=CC=C(C=C1)C(C(F)(F)F)NCC DAPPJWVDRCNIOP-UHFFFAOYSA-N 0.000 claims 1
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- PBFXWUVYOSGQRL-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[4-[3-hydroxy-3-(trifluoromethyl)pyrrolidin-1-yl]sulfonylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound C1(CC1)C(CC#N)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N2CC(CC2)(C(F)(F)F)O PBFXWUVYOSGQRL-UHFFFAOYSA-N 0.000 claims 1
- VFEFOPFPKVKTJU-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[4-[4-(2-hydroxypropan-2-yl)piperidine-1-carbonyl]-3-methylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound Cc1cc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)ccc1C(=O)N1CCC(CC1)C(C)(C)O VFEFOPFPKVKTJU-UHFFFAOYSA-N 0.000 claims 1
- AGFXWLQMNJKGNT-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[[1-hydroxy-1-(trifluoromethyl)-2,3-dihydroinden-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound C1(CC1)C(CC#N)N1N=C(C=2C(NC=CC21)=O)NC=2C=C1CCC(C1=CC2)(C(F)(F)F)O AGFXWLQMNJKGNT-UHFFFAOYSA-N 0.000 claims 1
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- SRJBZWDRDFVLBD-UHFFFAOYSA-N 3-cyclopropyl-3-[4-oxo-3-[4-[2-(trifluoromethyl)oxolan-2-yl]anilino]-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound FC(F)(F)C1(CCCO1)c1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1 SRJBZWDRDFVLBD-UHFFFAOYSA-N 0.000 claims 1
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- ZIZIGOYRJXMERM-UHFFFAOYSA-N 3-cyclopropyl-3-[4-oxo-3-[4-[2-(trifluoromethyl)pyrrolidin-1-yl]sulfonylanilino]-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound FC(F)(F)C1CCCN1S(=O)(=O)c1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1 ZIZIGOYRJXMERM-UHFFFAOYSA-N 0.000 claims 1
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- UFMDTBJDHWTRSF-UHFFFAOYSA-N 3-cyclopropyl-3-[4-oxo-3-[4-[3-(trifluoromethyl)pyrrolidin-1-yl]sulfonylanilino]-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound FC(F)(F)C1CCN(C1)S(=O)(=O)c1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1 UFMDTBJDHWTRSF-UHFFFAOYSA-N 0.000 claims 1
- FHSOIHFCBYAHTJ-UHFFFAOYSA-N 3-cyclopropyl-3-[4-oxo-3-[[1-oxo-2-[1-(trifluoromethyl)cyclohexyl]-3H-isoindol-5-yl]amino]-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound FC(F)(F)C1(CCCCC1)N1Cc2cc(Nc3nn(C(CC#N)C4CC4)c4cc[nH]c(=O)c34)ccc2C1=O FHSOIHFCBYAHTJ-UHFFFAOYSA-N 0.000 claims 1
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- GFTCIBSVVIJOTR-UHFFFAOYSA-N 4-[[1-(2-cyano-1-cyclopropylethyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]-N,N-dimethylbenzenesulfonamide Chemical compound C(#N)CC(C1CC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C GFTCIBSVVIJOTR-UHFFFAOYSA-N 0.000 claims 1
- XBGUAPSYQMIJMX-UHFFFAOYSA-N 4-[[1-(2-cyano-1-cyclopropylethyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]-N-methylbenzenesulfonamide Chemical compound C(#N)CC(C1CC1)N1N=C(C=2C(NC=CC=21)=O)NC1=CC=C(C=C1)S(=O)(=O)NC XBGUAPSYQMIJMX-UHFFFAOYSA-N 0.000 claims 1
- IMTRDOJOGBPLGC-UHFFFAOYSA-N 4-[[1-(2-cyano-1-cyclopropylethyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]benzoic acid Chemical compound C(#N)CC(C1CC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C(=O)O)C=C2 IMTRDOJOGBPLGC-UHFFFAOYSA-N 0.000 claims 1
- JTZQNDIXTQDVOE-UHFFFAOYSA-N 4-[[1-(2-cyano-1-cyclopropylethyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]benzonitrile Chemical compound C(#N)CC(C1CC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C#N)C=C2 JTZQNDIXTQDVOE-UHFFFAOYSA-N 0.000 claims 1
- GCWVONWDGUVUEW-UHFFFAOYSA-N 4-[[1-[2-cyano-1-(2,2-dimethylcyclopropyl)ethyl]-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]-N,N-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)c1ccc(Nc2nn(C(CC#N)C3CC3(C)C)c3cc[nH]c(=O)c23)cc1 GCWVONWDGUVUEW-UHFFFAOYSA-N 0.000 claims 1
- 208000000884 Airway Obstruction Diseases 0.000 claims 1
- 206010003559 Asthma late onset Diseases 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 206010014561 Emphysema Diseases 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
- 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
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 1
- 201000009961 allergic asthma Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 208000023819 chronic asthma Diseases 0.000 claims 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000428 dust Substances 0.000 claims 1
- ZNHJTMAKBXDJIV-UHFFFAOYSA-N ethyl 1-[4-[[1-(2-cyano-1-cyclopropylethyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]-2-methylphenyl]pyrazole-4-carboxylate Chemical compound C(#N)CC(C1CC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC(=C(C=C2)N2N=CC(=C2)C(=O)OCC)C ZNHJTMAKBXDJIV-UHFFFAOYSA-N 0.000 claims 1
- BZAZILNZTPOWNV-UHFFFAOYSA-N ethyl 2-[[4-[[1-(2-cyano-1-cyclopropylethyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]phenyl]sulfonyl-methylamino]-2-methylpropanoate Chemical compound C(#N)CC(C1CC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C(C(=O)OCC)(C)C BZAZILNZTPOWNV-UHFFFAOYSA-N 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000009610 hypersensitivity Effects 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- IRFPZZVVAKHCCC-UHFFFAOYSA-N methyl 3-[4-(azetidin-1-ylsulfonyl)anilino]-1-(2-cyano-1-cyclopropylethyl)-4-oxo-5H-pyrazolo[4,3-c]pyridine-7-carboxylate Chemical compound COC(=O)c1c[nH]c(=O)c2c(Nc3ccc(cc3)S(=O)(=O)N3CCC3)nn(C(CC#N)C3CC3)c12 IRFPZZVVAKHCCC-UHFFFAOYSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- DZBUGZXBQABLFQ-UHFFFAOYSA-N propan-2-yl 3-[4-[[1-(2-cyano-1-cyclopropylethyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]phenyl]-4,4,4-trifluoro-3-hydroxy-2,2-dimethylbutanoate Chemical compound C(#N)CC(C1CC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)C(C(C(=O)OC(C)C)(C)C)(C(F)(F)F)O DZBUGZXBQABLFQ-UHFFFAOYSA-N 0.000 claims 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-M quinaldate Chemical compound C1=CC=CC2=NC(C(=O)[O-])=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-M 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- JARNXUZSANRLLA-UHFFFAOYSA-N tert-butyl 2-[6-[[1-(2-cyano-1-cyclopropylethyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]-3-oxo-1H-isoindol-2-yl]-2-methylpropanoate Chemical compound C(#N)CC(C1CC1)N1N=C(C=2C(NC=CC21)=O)NC=2C=C1CN(C(C1=CC2)=O)C(C(=O)OC(C)(C)C)(C)C JARNXUZSANRLLA-UHFFFAOYSA-N 0.000 claims 1
- NTIMHFOMMPVJME-UHFFFAOYSA-N tert-butyl 2-[[4-[[1-(2-cyano-1-cyclopropylethyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]phenyl]sulfonyl-methylamino]-2-methylpropanoate Chemical compound C(#N)CC(C1CC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)S(=O)(=O)N(C)C(C(=O)OC(C)(C)C)(C)C NTIMHFOMMPVJME-UHFFFAOYSA-N 0.000 claims 1
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
- C07D471/10—Spiro-condensed systems
-
- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
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- 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
- C07D487/08—Bridged systems
-
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- Public Health (AREA)
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- Neurology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| US201361803241P | 2013-03-19 | 2013-03-19 | |
| US61/803,241 | 2013-03-19 | ||
| PCT/CN2014/000299 WO2014146493A1 (en) | 2013-03-19 | 2014-03-19 | Acyclic cyanoethylpyrazolo pyridones as janus kinase inhibitors |
Publications (1)
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| RU2015144385A true RU2015144385A (ru) | 2017-04-26 |
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| EP (1) | EP2976341B1 (https=) |
| JP (1) | JP6305510B2 (https=) |
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| WO2014146246A1 (en) * | 2013-03-19 | 2014-09-25 | Merck Sharp & Dohme Corp. | Cycloalkyl nitrile pyrazolo pyridones as janus kinase inhibitors |
| WO2016061751A1 (en) | 2014-10-22 | 2016-04-28 | Merck Sharp & Dohme Corp. | Ethyl n-boc piperidinyl pyrazolo pyridones as janus kinase inhibitors |
| CN105327207A (zh) * | 2015-12-07 | 2016-02-17 | 雷文金 | 一种治疗风湿热痹的中药组合物 |
| CN105435170A (zh) * | 2015-12-11 | 2016-03-30 | 张量才 | 一种食药同源的中药保健食品 |
| WO2018235926A1 (ja) | 2017-06-23 | 2018-12-27 | 協和発酵キリン株式会社 | α、β不飽和アミド化合物 |
| US11098216B2 (en) | 2017-09-28 | 2021-08-24 | Ricoh Company, Ltd. | Image forming method, image forming apparatus, and method for manufacturing printed matter |
| EP3650447A1 (en) * | 2018-11-08 | 2020-05-13 | Universite de Nantes | New selective modulators of insect nicotinic acetylcholine receptors |
| CN111499592B (zh) * | 2020-03-14 | 2023-06-23 | 江苏省农用激素工程技术研究中心有限公司 | 5-氨甲基糖精的合成方法 |
| CN116157124A (zh) * | 2020-05-29 | 2023-05-23 | 大邱庆北尖端医疗产业振兴财团 | 磺胺衍生物和含其作为活性成分的用于预防或治疗精神疾病的药物组合物 |
| CN112694497A (zh) * | 2020-12-25 | 2021-04-23 | 蚌埠中实化学技术有限公司 | 一种4-异丙基磺酰基苯硼酸的制备方法 |
| KR20250031189A (ko) * | 2022-06-16 | 2025-03-06 | 엔썸 테라퓨틱스, 아이엔씨. | 아닐리노-피라졸 유도체, 이의 조성물 및 방법 |
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| EP2123651A4 (en) | 2007-01-12 | 2011-05-04 | Astellas Pharma Inc | CONDENSED PYRIDINE COMPOUND |
| US9346809B2 (en) | 2009-07-08 | 2016-05-24 | Leo Pharma A/S | Heterocyclic compounds as JAK receptor and protein tyrosine kinase inhibitors |
| EP2475667A1 (en) * | 2009-09-10 | 2012-07-18 | F. Hoffmann-La Roche AG | Inhibitors of jak |
| PT3354652T (pt) | 2010-03-10 | 2020-07-20 | Incyte Holdings Corp | Derivados de piperidin-4-ilazetidina como inibidores de jak1 |
| WO2012127506A1 (en) | 2011-03-22 | 2012-09-27 | Advinus Therapeutics Limited | Substituted fused tricyclic compounds, compositions and medicinal applications thereof |
| WO2013017480A1 (en) | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
| WO2013017479A1 (en) | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
| WO2013180265A1 (ja) * | 2012-06-01 | 2013-12-05 | 武田薬品工業株式会社 | 複素環化合物 |
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Also Published As
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|---|---|
| CN105121444A (zh) | 2015-12-02 |
| WO2014146493A1 (en) | 2014-09-25 |
| CA2901770A1 (en) | 2014-09-25 |
| US20160272634A1 (en) | 2016-09-22 |
| EP2976341A1 (en) | 2016-01-27 |
| KR20150132170A (ko) | 2015-11-25 |
| MX2015013419A (es) | 2016-07-19 |
| US10059705B2 (en) | 2018-08-28 |
| AU2014234909B2 (en) | 2017-10-05 |
| JP2016514711A (ja) | 2016-05-23 |
| EP2976341A4 (en) | 2016-10-12 |
| JP6305510B2 (ja) | 2018-04-04 |
| BR112015024050A2 (pt) | 2017-07-18 |
| CN105121444B (zh) | 2018-02-16 |
| AU2014234909A1 (en) | 2015-08-13 |
| EP2976341B1 (en) | 2018-02-28 |
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