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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| 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 |
| WO2021241875A1 (ko) * | 2020-05-29 | 2021-12-02 | 재단법인 대구경북첨단의료산업진흥재단 | 설폰아미드 유도체 및 이를 유효성분으로 함유하는 정신질환의 예방 또는 치료용 약학적 조성물 |
| 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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100105661A1 (en) | 2007-01-12 | 2010-04-29 | 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 |
| EP3715347B1 (en) | 2010-03-10 | 2021-12-22 | Incyte Holdings Corporation | Piperidin-4-yl azetidine derivatives as jak1 inhibitors |
| WO2012127506A1 (en) * | 2011-03-22 | 2012-09-27 | Advinus Therapeutics Limited | Substituted fused tricyclic compounds, compositions and medicinal applications thereof |
| 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 |
| EA201492250A1 (ru) * | 2012-06-01 | 2015-08-31 | Такеда Фармасьютикал Компани Лимитед | Гетероциклическое соединение |
-
2014
- 2014-03-19 US US14/778,055 patent/US10059705B2/en active Active
- 2014-03-19 BR BR112015024050A patent/BR112015024050A2/pt not_active Application Discontinuation
- 2014-03-19 AU AU2014234909A patent/AU2014234909B2/en not_active Ceased
- 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
- 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 CA CA2901770A patent/CA2901770A1/en not_active Abandoned
- 2014-03-19 EP EP14770056.1A patent/EP2976341B1/en active Active
- 2014-03-19 JP JP2016503523A patent/JP6305510B2/ja not_active Expired - Fee Related
- 2014-03-19 KR KR1020157025520A patent/KR20150132170A/ko not_active Withdrawn
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