JP2016514711A5 - - Google Patents
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- Publication number
- JP2016514711A5 JP2016514711A5 JP2016503523A JP2016503523A JP2016514711A5 JP 2016514711 A5 JP2016514711 A5 JP 2016514711A5 JP 2016503523 A JP2016503523 A JP 2016503523A JP 2016503523 A JP2016503523 A JP 2016503523A JP 2016514711 A5 JP2016514711 A5 JP 2016514711A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- oxo
- amino
- pyrazolo
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 73
- -1 trifluoromethoxy, trifluoroethoxy Chemical group 0.000 claims 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 36
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 27
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 13
- 208000006673 asthma Diseases 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 5
- 125000005605 benzo 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
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims 5
- 206010003246 arthritis Diseases 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000006652 (C3-C12) cycloalkyl group Chemical group 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
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 230000005764 inhibitory process Effects 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 208000023275 Autoimmune 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
- 125000004644 alkyl sulfinyl 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
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 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
- 150000002431 hydrogen Chemical class 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
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
- PCNHZFDBRNGATB-UHFFFAOYSA-N 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-methylpropanoic acid Chemical compound C(#N)CC(C1CC1)N1N=C(C=2C(NC=CC21)=O)NC=2C=C1CN(C(C1=CC2)=O)C(C(=O)O)(C)C PCNHZFDBRNGATB-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
- 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
- OMKGHJWWGRREQE-UHFFFAOYSA-N 3-[3-[(2-tert-butyl-1-oxo-3H-isoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-3-cyclopropylpropanenitrile Chemical compound C(C)(C)(C)N1C(C2=CC=C(C=C2C1)NC1=NN(C2=C1C(NC=C2)=O)C(CC#N)C1CC1)=O OMKGHJWWGRREQE-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
- 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
- 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
- LAXNEAONBBFSGC-UHFFFAOYSA-N 3-cyclopropyl-3-[3-(3-fluoro-4-methylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound CS(=O)(=O)c1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1F LAXNEAONBBFSGC-UHFFFAOYSA-N 0.000 claims 1
- RIUKWICIEVYYFD-UHFFFAOYSA-N 3-cyclopropyl-3-[3-(4-fluoroanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound Fc1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1 RIUKWICIEVYYFD-UHFFFAOYSA-N 0.000 claims 1
- VMSDCHMWZZFAHB-UHFFFAOYSA-N 3-cyclopropyl-3-[3-(4-methylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound CS(=O)(=O)c1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1 VMSDCHMWZZFAHB-UHFFFAOYSA-N 0.000 claims 1
- RFEFYMMLCQFKDD-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[(2-fluoropyridin-4-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound Fc1cc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)ccn1 RFEFYMMLCQFKDD-UHFFFAOYSA-N 0.000 claims 1
- ZHGMGFIKGZDCGQ-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[(2-hydroxy-2-methyl-1,3-dihydroinden-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound CC1(O)Cc2ccc(Nc3nn(C(CC#N)C4CC4)c4cc[nH]c(=O)c34)cc2C1 ZHGMGFIKGZDCGQ-UHFFFAOYSA-N 0.000 claims 1
- YMVJHFGFPMQTAI-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[(2-methyl-1,3-benzothiazol-6-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound Cc1nc2ccc(Nc3nn(C(CC#N)C4CC4)c4cc[nH]c(=O)c34)cc2s1 YMVJHFGFPMQTAI-UHFFFAOYSA-N 0.000 claims 1
- SLKKJAHWCHMJCP-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[(2-morpholin-4-ylquinolin-6-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccc4nc(ccc4c3)N3CCOCC3)c12)C(CC#N)C1CC1 SLKKJAHWCHMJCP-UHFFFAOYSA-N 0.000 claims 1
- WEYUNWFIDXOVSJ-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[(3,3-dimethyl-2-oxo-1H-indol-6-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound CC1(C)C(=O)Nc2cc(Nc3nn(C(CC#N)C4CC4)c4cc[nH]c(=O)c34)ccc12 WEYUNWFIDXOVSJ-UHFFFAOYSA-N 0.000 claims 1
- XVIBPYRSHXBYFS-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[3-fluoro-4-(2,2,2-trifluoro-1-hydroxyethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]propanenitrile Chemical compound OC(c1ccc(Nc2nn(C(CC#N)C3CC3)c3cc[nH]c(=O)c23)cc1F)C(F)(F)F XVIBPYRSHXBYFS-UHFFFAOYSA-N 0.000 claims 1
- RXSJBDXBUQLLNZ-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[3-fluoro-4-[2,2,2-trifluoro-1-(propan-2-ylamino)ethyl]anilino]-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)C(C(F)(F)F)NC(C)C)F RXSJBDXBUQLLNZ-UHFFFAOYSA-N 0.000 claims 1
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| 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 |
| US11447471B2 (en) | 2017-06-23 | 2022-09-20 | Kyowa Kirin Co., Ltd. | α,β-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 |
| 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 |
| CN120842212A (zh) * | 2022-06-16 | 2025-10-28 | 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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| AR064879A1 (es) | 2007-01-12 | 2009-04-29 | Astellas Pharma Inc | Compuesto de piridina condensado |
| WO2011003418A1 (en) * | 2009-07-08 | 2011-01-13 | Leo Pharma A/S | Heterocyclic compounds as jak receptor and protein tyrosine kinase inhibitors |
| JP5658756B2 (ja) * | 2009-09-10 | 2015-01-28 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｊａｋの阻害剤 |
| EP3354652B1 (en) | 2010-03-10 | 2020-05-06 | Incyte Holdings Corporation | Piperidin-4-yl azetidine derivatives as jak1 inhibitors |
| CN103547580B (zh) * | 2011-03-22 | 2016-12-07 | 阿迪维纳斯疗法有限公司 | 取代的稠合三环化合物、其组合物及医药用途 |
| WO2013017479A1 (en) * | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
| WO2013017480A1 (en) | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
| US9371320B2 (en) * | 2012-06-01 | 2016-06-21 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
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2014
- 2014-03-19 JP JP2016503523A patent/JP6305510B2/ja not_active Expired - Fee Related
- 2014-03-19 KR KR1020157025520A patent/KR20150132170A/ko not_active Withdrawn
- 2014-03-19 US US14/778,055 patent/US10059705B2/en active Active
- 2014-03-19 CA CA2901770A patent/CA2901770A1/en not_active Abandoned
- 2014-03-19 AU AU2014234909A patent/AU2014234909B2/en not_active Ceased
- 2014-03-19 EP EP14770056.1A patent/EP2976341B1/en active Active
- 2014-03-19 BR BR112015024050A patent/BR112015024050A2/pt not_active Application Discontinuation
- 2014-03-19 WO PCT/CN2014/000299 patent/WO2014146493A1/en not_active Ceased
- 2014-03-19 MX MX2015013419A patent/MX2015013419A/es unknown
- 2014-03-19 RU RU2015144385A patent/RU2015144385A/ru not_active Application Discontinuation
- 2014-03-19 CN CN201480016814.2A patent/CN105121444B/zh not_active Expired - Fee Related
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