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
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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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- 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
-
- 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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- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epidemiology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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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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| 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 |
| SG11201912770SA (en) | 2017-06-23 | 2020-01-30 | Kyowa Kirin Co Ltd | a, ß-UNSATURATED AMIDE COMPOUND |
| 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 |
| US20230212121A1 (en) * | 2020-05-29 | 2023-07-06 | Daegu-Gyeongbuk Medical Innovation Foundation | Sulfonamide derivative and pharmaceutical composition comprising same as active ingredient for preventing or treating mental illness |
| 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 |
| CN119384413A (zh) * | 2022-06-16 | 2025-01-28 | 昂胜医药有限公司 | 苯胺基-吡唑衍生物、其组合物和方法 |
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| EP2123651A4 (en) | 2007-01-12 | 2011-05-04 | Astellas Pharma Inc | CONDENSED PYRIDINE COMPOUND |
| TW201105674A (en) * | 2009-07-08 | 2011-02-16 | Leo Pharma As | Novel JAK receptor and protein tyrosine kinase inhibitors and pharmaceutical use thereof |
| RU2538204C2 (ru) * | 2009-09-10 | 2015-01-10 | Ф.Хоффманн-Ля Рош Аг | Ингибиторы jak |
| SMT201800137T1 (it) | 2010-03-10 | 2018-07-17 | Incyte Holdings Corp | Derivati di piperidin-4-il azetidina come inibitori di jak1 |
| EP2688890B1 (en) * | 2011-03-22 | 2017-08-30 | 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 |
| BR112014029705A2 (pt) | 2012-06-01 | 2017-06-27 | Takeda Pharmaceuticals Co | composto ou sal, medicamento, métodos para inibir quinase de janus em um mamífero, e para a profilaxia ou tratamento de doenças autoimunes, e, uso de um composto ou sal |
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Also Published As
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| KR20150132170A (ko) | 2015-11-25 |
| MX2015013419A (es) | 2016-07-19 |
| AU2014234909B2 (en) | 2017-10-05 |
| JP6305510B2 (ja) | 2018-04-04 |
| US20160272634A1 (en) | 2016-09-22 |
| US10059705B2 (en) | 2018-08-28 |
| AU2014234909A1 (en) | 2015-08-13 |
| EP2976341A4 (en) | 2016-10-12 |
| BR112015024050A2 (pt) | 2017-07-18 |
| EP2976341A1 (en) | 2016-01-27 |
| EP2976341B1 (en) | 2018-02-28 |
| JP2016514711A (ja) | 2016-05-23 |
| WO2014146493A1 (en) | 2014-09-25 |
| CN105121444A (zh) | 2015-12-02 |
| CA2901770A1 (en) | 2014-09-25 |
| CN105121444B (zh) | 2018-02-16 |
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