JP2016518344A5 - - Google Patents
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- JP2016518344A5 JP2016518344A5 JP2016503520A JP2016503520A JP2016518344A5 JP 2016518344 A5 JP2016518344 A5 JP 2016518344A5 JP 2016503520 A JP2016503520 A JP 2016503520A JP 2016503520 A JP2016503520 A JP 2016503520A JP 2016518344 A5 JP2016518344 A5 JP 2016518344A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- dihydro
- amino
- oxo
- pyrazolo
- 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 306
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 88
- -1 aminocarbonyloxy Chemical group 0.000 claims 83
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 64
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 claims 30
- 125000001072 heteroaryl group Chemical group 0.000 claims 25
- 125000003282 alkyl amino group Chemical group 0.000 claims 23
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 23
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 18
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000004404 heteroalkyl group Chemical group 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 9
- 208000006673 asthma Diseases 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000006413 ring segment Chemical group 0.000 claims 5
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 4
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 125000006374 C2-C10 alkenyl 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
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 230000001668 ameliorated effect Effects 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 206010003246 arthritis Diseases 0.000 claims 3
- UIZRDFICGGONJJ-UHFFFAOYSA-N cycloheptanecarbonitrile Chemical compound N#CC1CCCCCC1 UIZRDFICGGONJJ-UHFFFAOYSA-N 0.000 claims 3
- SVPZJHKVRMRREG-UHFFFAOYSA-N cyclopentanecarbonitrile Chemical compound N#CC1CCCC1 SVPZJHKVRMRREG-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000005764 inhibitory process Effects 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 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
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- UAZBMUAXZPHBEH-UHFFFAOYSA-N 2-[3-[3-(aminomethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound NCc1cccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)c1 UAZBMUAXZPHBEH-UHFFFAOYSA-N 0.000 claims 2
- PJGQQHWVCVIHBU-UHFFFAOYSA-N 2-[3-[4-(1-amino-2,2,2-trifluoroethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclopentane-1-carbonitrile Chemical compound NC(c1ccc(Nc2nn(C3CCCC3C#N)c3cc[nH]c(=O)c23)cc1)C(F)(F)F PJGQQHWVCVIHBU-UHFFFAOYSA-N 0.000 claims 2
- ATDOLCJEBSOYTC-UHFFFAOYSA-N 2-[4-oxo-3-[4-[1-(2,2,2-trifluoroethylamino)ethyl]anilino]-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC(NCC(F)(F)F)c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1 ATDOLCJEBSOYTC-UHFFFAOYSA-N 0.000 claims 2
- UXOUMFKAAGLFPS-UHFFFAOYSA-N 2-[4-oxo-3-[4-[2-(triazol-1-yl)propan-2-yl]anilino]-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC(C)(c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1)n1ccnn1 UXOUMFKAAGLFPS-UHFFFAOYSA-N 0.000 claims 2
- HAOJRYPDUQJHGB-UHFFFAOYSA-N 5-(1-cyclopropylethylamino)-2-[4-oxo-3-[4-(trifluoromethyl)anilino]-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound C1(CC1)C(C)NC1CCC(C(C1)C#N)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)C(F)(F)F HAOJRYPDUQJHGB-UHFFFAOYSA-N 0.000 claims 2
- VTJWCDXVXRPCAT-UHFFFAOYSA-N 6-[3-(4-methylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]spiro[2.5]octane-7-carbonitrile Chemical compound CS(=O)(=O)c1ccc(Nc2nn(C3CCC4(CC4)CC3C#N)c3cc[nH]c(=O)c23)cc1 VTJWCDXVXRPCAT-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- VGUHOWNAJPXECC-UHFFFAOYSA-N 1-[3-[(2-methyl-1,3-dihydroisoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CN1Cc2ccc(Nc3nn(c4cc[nH]c(=O)c34)C3(CCCCC3)C#N)cc2C1 VGUHOWNAJPXECC-UHFFFAOYSA-N 0.000 claims 1
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- 125000005938 2,3-dihydro-1H-isoindolyl group Chemical group 0.000 claims 1
- VOXOHXOGJVKLMU-UHFFFAOYSA-N 2-(3-anilino-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexane-1-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccccc3)c12)C1CCCCC1C#N VOXOHXOGJVKLMU-UHFFFAOYSA-N 0.000 claims 1
- GBHIKDNNYJBTRC-UHFFFAOYSA-N 2-(aminomethyl)-4-[[1-(2-cyanocyclohexyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]-N,N-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1CN GBHIKDNNYJBTRC-UHFFFAOYSA-N 0.000 claims 1
- DYDILULJFRNVHO-UHFFFAOYSA-N 2-[3-(2,3-dihydro-1H-isoindol-5-ylamino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccc4CNCc4c3)c12)C1CCCCC1C#N DYDILULJFRNVHO-UHFFFAOYSA-N 0.000 claims 1
- UKIPVDAJUNAYOH-UHFFFAOYSA-N 2-[3-(4-chloro-3-fluoroanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-5-(1-cyclopropylethylamino)cyclohexane-1-carbonitrile Chemical compound ClC1=C(C=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C2C(CC(CC2)NC(C)C2CC2)C#N)F UKIPVDAJUNAYOH-UHFFFAOYSA-N 0.000 claims 1
- CTAVNIWHFDNHFG-UHFFFAOYSA-N 2-[3-(4-chloroanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-5-(3-hydroxy-3-methylazetidin-1-yl)cyclohexane-1-carbonitrile Chemical compound CC1(O)CN(C1)C1CCC(C(C1)C#N)n1nc(Nc2ccc(Cl)cc2)c2c1cc[nH]c2=O CTAVNIWHFDNHFG-UHFFFAOYSA-N 0.000 claims 1
- DZMPLXBTLJHOAP-UHFFFAOYSA-N 2-[3-(4-chloroanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-5-(3-hydroxyazetidin-1-yl)cyclohexane-1-carbonitrile Chemical compound OC1CN(C1)C1CCC(C(C1)C#N)n1nc(Nc2ccc(Cl)cc2)c2c1cc[nH]c2=O DZMPLXBTLJHOAP-UHFFFAOYSA-N 0.000 claims 1
- JNKWGCLPFCMWJB-UHFFFAOYSA-N 2-[3-(4-chloroanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-5-(dimethylamino)cyclohexane-1-carbonitrile Chemical compound CN(C)C1CCC(C(C1)C#N)n1nc(Nc2ccc(Cl)cc2)c2c1cc[nH]c2=O JNKWGCLPFCMWJB-UHFFFAOYSA-N 0.000 claims 1
- NQRSUOLAPVLOMC-UHFFFAOYSA-N 2-[3-(4-chloroanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound Clc1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1 NQRSUOLAPVLOMC-UHFFFAOYSA-N 0.000 claims 1
- CPSWKXQLHRUVAH-UHFFFAOYSA-N 2-[3-(4-fluoroanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound Fc1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1 CPSWKXQLHRUVAH-UHFFFAOYSA-N 0.000 claims 1
- VCOKRWKMGKNSAQ-UHFFFAOYSA-N 2-[3-(4-methylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CS(=O)(=O)c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1 VCOKRWKMGKNSAQ-UHFFFAOYSA-N 0.000 claims 1
- XNFBERIMCFBCPW-UHFFFAOYSA-N 2-[3-(4-methylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclopentane-1-carbonitrile Chemical compound CS(=O)(=O)c1ccc(Nc2nn(C3CCCC3C#N)c3cc[nH]c(=O)c23)cc1 XNFBERIMCFBCPW-UHFFFAOYSA-N 0.000 claims 1
- BIEAHKDFPDDCMJ-UHFFFAOYSA-N 2-[3-(4-morpholin-4-ylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccc(cc3)S(=O)(=O)N3CCOCC3)c12)C1CCCCC1C#N BIEAHKDFPDDCMJ-UHFFFAOYSA-N 0.000 claims 1
- OKKSQYGPSXAHSK-UHFFFAOYSA-N 2-[3-(4-tert-butylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]-4,4-difluorocyclopentane-1-carbonitrile Chemical compound C(C)(C)(C)S(=O)(=O)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C2C(CC(C2)(F)F)C#N OKKSQYGPSXAHSK-UHFFFAOYSA-N 0.000 claims 1
- GZAHUQDDMULFOK-UHFFFAOYSA-N 2-[3-(4-tert-butylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cycloheptane-1-carbonitrile Chemical compound C(C)(C)(C)S(=O)(=O)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1C(CCCCC1)C#N GZAHUQDDMULFOK-UHFFFAOYSA-N 0.000 claims 1
- MIOFBJPHSJSMQP-UHFFFAOYSA-N 2-[3-(4-tert-butylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound C(C)(C)(C)S(=O)(=O)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1C(CCCC1)C#N MIOFBJPHSJSMQP-UHFFFAOYSA-N 0.000 claims 1
- VJDNXRHBICPHQQ-UHFFFAOYSA-N 2-[3-(4-tert-butylsulfonylanilino)-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclopentane-1-carbonitrile Chemical compound C(C)(C)(C)S(=O)(=O)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1C(CCC1)C#N VJDNXRHBICPHQQ-UHFFFAOYSA-N 0.000 claims 1
- DXCALSOZWMAYAH-UHFFFAOYSA-N 2-[3-[(1-methyl-2,3-dihydro-1H-isoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC1NCc2cc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)ccc12 DXCALSOZWMAYAH-UHFFFAOYSA-N 0.000 claims 1
- VRQZJCHFVYKQRJ-UHFFFAOYSA-N 2-[3-[(1-methyl-2-propan-2-yl-1,3-dihydroisoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC(C)N1Cc2cc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)ccc2C1C VRQZJCHFVYKQRJ-UHFFFAOYSA-N 0.000 claims 1
- HFHNVRVTIYDFPV-UHFFFAOYSA-N 2-[3-[(2-acetyl-1,3-dihydroisoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC(=O)N1Cc2ccc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)cc2C1 HFHNVRVTIYDFPV-UHFFFAOYSA-N 0.000 claims 1
- YVCKPLXYPICZFN-UHFFFAOYSA-N 2-[3-[(2-cyclohexyl-1-oxo-3H-isoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=C1N(Cc2cc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)ccc12)C1CCCCC1 YVCKPLXYPICZFN-UHFFFAOYSA-N 0.000 claims 1
- CLQIXXQBNKZNQN-UHFFFAOYSA-N 2-[3-[(2-cyclopentyl-1-oxo-3H-isoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cycloheptane-1-carbonitrile Chemical compound O=C1N(Cc2cc(Nc3nn(C4CCCCCC4C#N)c4cc[nH]c(=O)c34)ccc12)C1CCCC1 CLQIXXQBNKZNQN-UHFFFAOYSA-N 0.000 claims 1
- CVLDIBUYNTTXTB-UHFFFAOYSA-N 2-[3-[(2-cyclopentyl-1-oxo-3H-isoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=C1N(Cc2cc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)ccc12)C1CCCC1 CVLDIBUYNTTXTB-UHFFFAOYSA-N 0.000 claims 1
- PJNRISQXTFKGGR-UHFFFAOYSA-N 2-[3-[(2-ethyl-1,3-dihydroisoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CCN1Cc2ccc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)cc2C1 PJNRISQXTFKGGR-UHFFFAOYSA-N 0.000 claims 1
- GJMZBZAUPKWIIB-UHFFFAOYSA-N 2-[3-[(2-fluoropyridin-4-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound Fc1cc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)ccn1 GJMZBZAUPKWIIB-UHFFFAOYSA-N 0.000 claims 1
- WCYNPWNUKWZKPY-UHFFFAOYSA-N 2-[3-[(2-fluoropyridin-4-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclopentane-1-carbonitrile Chemical compound Fc1cc(Nc2nn(C3CCCC3C#N)c3cc[nH]c(=O)c23)ccn1 WCYNPWNUKWZKPY-UHFFFAOYSA-N 0.000 claims 1
- QTGWYEWTYFFVCK-UHFFFAOYSA-N 2-[3-[(2-methyl-1,3-benzothiazol-6-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound Cc1nc2ccc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)cc2s1 QTGWYEWTYFFVCK-UHFFFAOYSA-N 0.000 claims 1
- AMQXWQZKGXOBRL-UHFFFAOYSA-N 2-[3-[(2-tert-butyl-1-oxo-3H-isoindol-5-yl)amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound C(C)(C)(C)N1C(C2=CC=C(C=C2C1)NC1=NN(C2=C1C(NC=C2)=O)C1C(CCCC1)C#N)=O AMQXWQZKGXOBRL-UHFFFAOYSA-N 0.000 claims 1
- HIHZYZIKHGCBEA-UHFFFAOYSA-N 2-[3-[3-(1,2-dihydroxypropan-2-yl)-4-methylsulfonylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC(O)(CO)c1cc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)ccc1S(C)(=O)=O HIHZYZIKHGCBEA-UHFFFAOYSA-N 0.000 claims 1
- YYXWWSMVXRDURD-UHFFFAOYSA-N 2-[3-[3-(1,2-dihydroxypropan-2-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC(O)(CO)c1cccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)c1 YYXWWSMVXRDURD-UHFFFAOYSA-N 0.000 claims 1
- GYHGNFLPFAUJBG-UHFFFAOYSA-N 2-[3-[3-(1,5-dihydro-1,2,4-triazol-4-ylmethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=C1NC=CC2=C1C(NC1=CC(CN3CNN=C3)=CC=C1)=NN2C1CCCCC1C#N GYHGNFLPFAUJBG-UHFFFAOYSA-N 0.000 claims 1
- ADTCEHDKQGPDDH-UHFFFAOYSA-N 2-[3-[3-(1-amino-2,2,2-trifluoroethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound NC(c1cccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)c1)C(F)(F)F ADTCEHDKQGPDDH-UHFFFAOYSA-N 0.000 claims 1
- KJSMYXLVRYQCHA-UHFFFAOYSA-N 2-[3-[3-(1-hydroxyethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound OC(C)C=1C=C(C=CC1)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N KJSMYXLVRYQCHA-UHFFFAOYSA-N 0.000 claims 1
- LEFREDRJGSTZPV-UHFFFAOYSA-N 2-[3-[3-(2,4-dihydroxybutan-2-yl)-4-methylsulfonylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound OC(CCO)(C)C=1C=C(C=CC1S(=O)(=O)C)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N LEFREDRJGSTZPV-UHFFFAOYSA-N 0.000 claims 1
- GWBIDPBMLMCWJJ-UHFFFAOYSA-N 2-[3-[3-(2-hydroxy-1-methoxypropan-2-yl)-4-methylsulfonylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound COCC(C)(O)c1cc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)ccc1S(C)(=O)=O GWBIDPBMLMCWJJ-UHFFFAOYSA-N 0.000 claims 1
- GCXNPUUZRKRWBG-UHFFFAOYSA-N 2-[3-[3-(aminomethyl)-4-fluoroanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound NCC=1C=C(C=CC1F)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N GCXNPUUZRKRWBG-UHFFFAOYSA-N 0.000 claims 1
- TULDCTUWXTXKOZ-UHFFFAOYSA-N 2-[3-[3-(aminomethyl)-4-methylsulfonylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound NCC=1C=C(C=CC1S(=O)(=O)C)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N TULDCTUWXTXKOZ-UHFFFAOYSA-N 0.000 claims 1
- AGHKZBGURRMENU-UHFFFAOYSA-N 2-[3-[3-(imidazol-1-ylmethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3cccc(Cn4ccnc4)c3)c12)C1CCCCC1C#N AGHKZBGURRMENU-UHFFFAOYSA-N 0.000 claims 1
- USFNKWFJXVRGKA-UHFFFAOYSA-N 2-[3-[3-(methylsulfanylmethyl)-5-(triazol-1-ylmethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CSCc1cc(Cn2ccnn2)cc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)c1 USFNKWFJXVRGKA-UHFFFAOYSA-N 0.000 claims 1
- OGCDZPLWWLGYAY-UHFFFAOYSA-N 2-[3-[3-(morpholin-4-ylmethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3cccc(CN4CCOCC4)c3)c12)C1CCCCC1C#N OGCDZPLWWLGYAY-UHFFFAOYSA-N 0.000 claims 1
- NXKINVPKJWSQMQ-UHFFFAOYSA-N 2-[3-[3-[(4-methyltriazol-1-yl)methyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound Cc1cn(Cc2cccc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)c2)nn1 NXKINVPKJWSQMQ-UHFFFAOYSA-N 0.000 claims 1
- LWHYZOANIAWTOD-UHFFFAOYSA-N 2-[3-[3-[(dimethylamino)methyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CN(C)CC=1C=C(C=CC1)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N LWHYZOANIAWTOD-UHFFFAOYSA-N 0.000 claims 1
- XKLZUPAFXVYMQF-UHFFFAOYSA-N 2-[3-[3-[[4-(2-hydroxypropan-2-yl)triazol-1-yl]methyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC(C)(O)c1cn(Cc2cccc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)c2)nn1 XKLZUPAFXVYMQF-UHFFFAOYSA-N 0.000 claims 1
- UMDUAFFINPREKZ-UHFFFAOYSA-N 2-[3-[3-chloro-4-(1-methylpyrazol-4-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound Cn1cc(cn1)-c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1Cl UMDUAFFINPREKZ-UHFFFAOYSA-N 0.000 claims 1
- ISRSDFMAQWVGFF-UHFFFAOYSA-N 2-[3-[3-methyl-4-(2,2,2-trifluoro-1-hydroxyethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cycloheptane-1-carbonitrile Chemical compound Cc1cc(Nc2nn(C3CCCCCC3C#N)c3cc[nH]c(=O)c23)ccc1C(O)C(F)(F)F ISRSDFMAQWVGFF-UHFFFAOYSA-N 0.000 claims 1
- AWPSAAQGCJQFHE-UHFFFAOYSA-N 2-[3-[3-methyl-4-(morpholine-4-carbonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC=1C=C(C=CC1C(=O)N1CCOCC1)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N AWPSAAQGCJQFHE-UHFFFAOYSA-N 0.000 claims 1
- UTEXWWBVIAGLGX-UHFFFAOYSA-N 2-[3-[3-methyl-4-(pyrrolidine-1-carbonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cycloheptane-1-carbonitrile Chemical compound Cc1cc(Nc2nn(C3CCCCCC3C#N)c3cc[nH]c(=O)c23)ccc1C(=O)N1CCCC1 UTEXWWBVIAGLGX-UHFFFAOYSA-N 0.000 claims 1
- WZWDGTNVIDQZIW-UHFFFAOYSA-N 2-[3-[3-methyl-4-(pyrrolidine-1-carbonyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound Cc1cc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)ccc1C(=O)N1CCCC1 WZWDGTNVIDQZIW-UHFFFAOYSA-N 0.000 claims 1
- GTTCCHTWJUTFER-UHFFFAOYSA-N 2-[3-[3-methyl-4-[2-(triazol-2-yl)propan-2-yl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound Cc1cc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)ccc1C(C)(C)n1nccn1 GTTCCHTWJUTFER-UHFFFAOYSA-N 0.000 claims 1
- DOGQIXWODOXNFJ-UHFFFAOYSA-N 2-[3-[3-methyl-4-[2-methyl-1-(triazol-1-yl)propyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC=1C=C(C=CC=1C(C(C)C)N1N=NC=C1)NC1=NN(C2=C1C(NC=C2)=O)C1C(CCCC1)C#N DOGQIXWODOXNFJ-UHFFFAOYSA-N 0.000 claims 1
- OLMVEFZLGYDEHT-UHFFFAOYSA-N 2-[3-[3-methyl-4-[2-methyl-1-(triazol-2-yl)propyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC=1C=C(C=CC=1C(C(C)C)N1N=CC=N1)NC1=NN(C2=C1C(NC=C2)=O)C1C(CCCC1)C#N OLMVEFZLGYDEHT-UHFFFAOYSA-N 0.000 claims 1
- WDBRDFPFLXOBLW-UHFFFAOYSA-N 2-[3-[4-(1,2,4-oxadiazol-3-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O1N=C(N=C1)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N WDBRDFPFLXOBLW-UHFFFAOYSA-N 0.000 claims 1
- SHRHJHVEQFNDKE-UHFFFAOYSA-N 2-[3-[4-(1,2,4-oxadiazol-5-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O1N=CN=C1C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N SHRHJHVEQFNDKE-UHFFFAOYSA-N 0.000 claims 1
- ICWALPQGNFEDJX-UHFFFAOYSA-N 2-[3-[4-(1,2-oxazol-3-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccc(cc3)-c3ccon3)c12)C1CCCCC1C#N ICWALPQGNFEDJX-UHFFFAOYSA-N 0.000 claims 1
- MDYMNELEGYVHIZ-UHFFFAOYSA-N 2-[3-[4-(1,2-oxazol-5-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccc(cc3)-c3ccno3)c12)C1CCCCC1C#N MDYMNELEGYVHIZ-UHFFFAOYSA-N 0.000 claims 1
- BNXGDFOGPPWZLC-UHFFFAOYSA-N 2-[3-[4-(1,3-oxazol-2-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccc(cc3)-c3ncco3)c12)C1CCCCC1C#N BNXGDFOGPPWZLC-UHFFFAOYSA-N 0.000 claims 1
- WXTKCDRDBWXULE-UHFFFAOYSA-N 2-[3-[4-(1,3-oxazol-5-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O1C=NC=C1C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N WXTKCDRDBWXULE-UHFFFAOYSA-N 0.000 claims 1
- CTUPBUJYNCQIRR-UHFFFAOYSA-N 2-[3-[4-(1-amino-2,2,2-trifluoroethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound NC(c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1)C(F)(F)F CTUPBUJYNCQIRR-UHFFFAOYSA-N 0.000 claims 1
- DNIZTARTTLUFJQ-UHFFFAOYSA-N 2-[3-[4-(1-amino-2,2-difluoroethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound NC(C(F)F)c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1 DNIZTARTTLUFJQ-UHFFFAOYSA-N 0.000 claims 1
- ZYXCNVOWZVXSCD-UHFFFAOYSA-N 2-[3-[4-(2,2-difluoro-1-hydroxyethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound OC(C(F)F)c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1 ZYXCNVOWZVXSCD-UHFFFAOYSA-N 0.000 claims 1
- ARYAQZUKPZQZJL-UHFFFAOYSA-N 2-[3-[4-(3-hydroxyoxetan-3-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound OC1(COC1)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C1C(CCCC1)C#N ARYAQZUKPZQZJL-UHFFFAOYSA-N 0.000 claims 1
- ZNJYOOTZYOFRAE-UHFFFAOYSA-N 2-[3-[4-(3-methyloxetan-3-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC1(COC1)c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1 ZNJYOOTZYOFRAE-UHFFFAOYSA-N 0.000 claims 1
- HVJUIUIEMYNGII-UHFFFAOYSA-N 2-[3-[4-(4,4-difluoropiperidine-1-carbonyl)-3-methylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound Cc1cc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)ccc1C(=O)N1CCC(F)(F)CC1 HVJUIUIEMYNGII-UHFFFAOYSA-N 0.000 claims 1
- XCRURJVKVSWTAM-UHFFFAOYSA-N 2-[3-[4-(8-azabicyclo[3.2.1]octan-3-yl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccc(cc3)C3CC4CCC(C3)N4)c12)C1CCCCC1C#N XCRURJVKVSWTAM-UHFFFAOYSA-N 0.000 claims 1
- ZOVJWSJAJOZSHM-UHFFFAOYSA-N 2-[3-[4-(aminomethyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound NCc1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1 ZOVJWSJAJOZSHM-UHFFFAOYSA-N 0.000 claims 1
- WQZISHYNPRQKEK-UHFFFAOYSA-N 2-[3-[4-(methylsulfonimidoyl)anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CS(=N)(=O)c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1 WQZISHYNPRQKEK-UHFFFAOYSA-N 0.000 claims 1
- KAYPIXOLPAYIHO-UHFFFAOYSA-N 2-[3-[4-[1-(2-cyanoethyl)pyrazol-4-yl]-3-methylanilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound Cc1cc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)ccc1-c1cnn(CCC#N)c1 KAYPIXOLPAYIHO-UHFFFAOYSA-N 0.000 claims 1
- FBZZXRLHBDPWIN-UHFFFAOYSA-N 2-[3-[4-[1-(2-cyanoethyl)pyrazol-4-yl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccc(cc3)-c3cnn(CCC#N)c3)c12)C1CCCCC1C#N FBZZXRLHBDPWIN-UHFFFAOYSA-N 0.000 claims 1
- HHONVTVNGIQVLY-UHFFFAOYSA-N 2-[3-[4-[1-(2-methoxyethyl)pyrazol-4-yl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound COCCn1cc(cn1)-c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1 HHONVTVNGIQVLY-UHFFFAOYSA-N 0.000 claims 1
- YYMDSPNSTINZRI-UHFFFAOYSA-N 2-[3-[4-[1-(4-tert-butyltriazol-1-yl)-2-methylpropyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound C(C)(C)(C)C=1N=NN(C1)C(C(C)C)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N YYMDSPNSTINZRI-UHFFFAOYSA-N 0.000 claims 1
- VWKCSBAJDUQLME-UHFFFAOYSA-N 2-[3-[4-[1-(dimethylamino)-2,2,2-trifluoroethyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CN(C)C(c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1)C(F)(F)F VWKCSBAJDUQLME-UHFFFAOYSA-N 0.000 claims 1
- WVCMIRMVNCFOSR-UHFFFAOYSA-N 2-[3-[4-[1-(ethylamino)-2,2,2-trifluoroethyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclopentane-1-carbonitrile Chemical compound CCNC(c1ccc(Nc2nn(C3CCCC3C#N)c3cc[nH]c(=O)c23)cc1)C(F)(F)F WVCMIRMVNCFOSR-UHFFFAOYSA-N 0.000 claims 1
- ZKZIPHUCGFOVLB-UHFFFAOYSA-N 2-[3-[4-[2-methyl-1-(triazol-1-yl)propyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC(C)C(c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1)n1ccnn1 ZKZIPHUCGFOVLB-UHFFFAOYSA-N 0.000 claims 1
- BFEYDXASQIJAFX-UHFFFAOYSA-N 2-[3-[4-[2-methyl-1-(triazol-2-yl)propyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC(C)C(c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1)n1nccn1 BFEYDXASQIJAFX-UHFFFAOYSA-N 0.000 claims 1
- SIYUZFDVNLUNCX-UHFFFAOYSA-N 2-[3-[4-[[4-(2-hydroxypropan-2-yl)triazol-1-yl]methyl]anilino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC(C)(O)c1cn(Cc2ccc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)cc2)nn1 SIYUZFDVNLUNCX-UHFFFAOYSA-N 0.000 claims 1
- NISSGNRGHLJWNR-UHFFFAOYSA-N 2-[3-[[1-(difluoromethyl)-2,3-dihydro-1H-isoindol-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound FC(F)C1NCc2cc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)ccc12 NISSGNRGHLJWNR-UHFFFAOYSA-N 0.000 claims 1
- LGYANGVIADNXKN-UHFFFAOYSA-N 2-[3-[[1-hydroxy-1-(trifluoromethyl)spiro[3H-indene-2,1'-cyclopropane]-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound OC1(C2(CC3=CC(=CC=C13)NC1=NN(C3=C1C(NC=C3)=O)C1C(CCCC1)C#N)CC2)C(F)(F)F LGYANGVIADNXKN-UHFFFAOYSA-N 0.000 claims 1
- CCCZIBMGTXABJH-UHFFFAOYSA-N 2-[3-[[1-hydroxy-2,2-dimethyl-1-(trifluoromethyl)-3H-inden-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound OC1(C(CC2=CC(=CC=C12)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N)(C)C)C(F)(F)F CCCZIBMGTXABJH-UHFFFAOYSA-N 0.000 claims 1
- KGXWGLAAORNYHC-UHFFFAOYSA-N 2-[3-[[2-(2,5-dimethylmorpholin-4-yl)quinolin-6-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC1CN(C(C)CO1)c1ccc2cc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)ccc2n1 KGXWGLAAORNYHC-UHFFFAOYSA-N 0.000 claims 1
- ATKCCCGNTGNAIY-UHFFFAOYSA-N 2-[3-[[2-(3-methylbutan-2-yl)-1,3-dihydroisoindol-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC(C)C(C)N1CC2=CC=C(NC3=NN(C4CCCCC4C#N)C4=C3C(=O)NC=C4)C=C2C1 ATKCCCGNTGNAIY-UHFFFAOYSA-N 0.000 claims 1
- JZCKKPDNCNCXLJ-UHFFFAOYSA-N 2-[3-[[2-(4-methyloxan-4-yl)-1-oxo-3H-isoindol-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound CC1(CCOCC1)N1Cc2cc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)ccc2C1=O JZCKKPDNCNCXLJ-UHFFFAOYSA-N 0.000 claims 1
- TVFDGOFYJFASLX-UHFFFAOYSA-N 2-[3-[[2-(cyclopentylmethyl)-1,3-dihydroisoindol-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound C1(CCCC1)CN1CC2=CC=C(C=C2C1)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCC2)C#N TVFDGOFYJFASLX-UHFFFAOYSA-N 0.000 claims 1
- FJESDGARAVAKKN-UHFFFAOYSA-N 2-[3-[[2-(cyclopropylmethyl)-1,3-dihydroisoindol-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=c1[nH]ccc2n(nc(Nc3ccc4CN(CC5CC5)Cc4c3)c12)C1CCCCC1C#N FJESDGARAVAKKN-UHFFFAOYSA-N 0.000 claims 1
- UKJBUBBQJRMSNN-UHFFFAOYSA-N 2-[3-[[2-(oxan-4-yl)-1-oxo-3H-isoindol-5-yl]amino]-4-oxo-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=C1N(Cc2cc(Nc3nn(C4CCCCC4C#N)c4cc[nH]c(=O)c34)ccc12)C1CCOCC1 UKJBUBBQJRMSNN-UHFFFAOYSA-N 0.000 claims 1
- BYTLKMQMWMIOQR-UHFFFAOYSA-N 2-[4-oxo-3-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)-5H-pyrazolo[4,3-c]pyridin-1-yl]cyclohexane-1-carbonitrile Chemical compound O=C1NC=CC2=C1C(=NN2C1C(CCCC1)C#N)NC=1C=C2CCNCC2=CC=1 BYTLKMQMWMIOQR-UHFFFAOYSA-N 0.000 claims 1
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- PRDKGBHGLAXRKO-UHFFFAOYSA-N N-[1-[4-[[1-(2-cyanocyclohexyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]phenyl]-2,2,2-trifluoroethyl]-2-methylpropane-2-sulfinamide Chemical compound C(#N)C1C(CCCC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(C=C2)C(C(F)(F)F)NS(=O)C(C)(C)C PRDKGBHGLAXRKO-UHFFFAOYSA-N 0.000 claims 1
- BKFLCEIRDZAROW-UHFFFAOYSA-N N-[[3-[[1-(2-cyanocyclohexyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]phenyl]methyl]-1,3-oxazole-5-carboxamide Chemical compound C(#N)C1C(CCCC1)N1N=C(C=2C(NC=CC21)=O)NC=2C=C(CNC(=O)C1=CN=CO1)C=CC2 BKFLCEIRDZAROW-UHFFFAOYSA-N 0.000 claims 1
- HUTCBQJYCVVCAW-UHFFFAOYSA-N N-[[3-[[1-(2-cyanocyclohexyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]phenyl]methyl]pyrimidine-2-carboxamide Chemical compound C(#N)C1C(CCCC1)N1N=C(C=2C(NC=CC21)=O)NC=2C=C(CNC(=O)C1=NC=CC=N1)C=CC2 HUTCBQJYCVVCAW-UHFFFAOYSA-N 0.000 claims 1
- MSSYLELXOQWMDA-UHFFFAOYSA-N N-[[4-[[1-(2-cyanocyclohexyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]phenyl]methyl]-1,3-oxazole-5-carboxamide Chemical compound C(#N)C1C(CCCC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(CNC(=O)C1=CN=CO1)C=C2 MSSYLELXOQWMDA-UHFFFAOYSA-N 0.000 claims 1
- FNABBFLNQUBWDU-UHFFFAOYSA-N N-[[4-[[1-(2-cyanocyclohexyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]phenyl]methyl]pyrimidine-2-carboxamide Chemical compound C(#N)C1C(CCCC1)N1N=C(C=2C(NC=CC21)=O)NC2=CC=C(CNC(=O)C1=NC=CC=N1)C=C2 FNABBFLNQUBWDU-UHFFFAOYSA-N 0.000 claims 1
- YGIVJNKHBGEKKY-UHFFFAOYSA-N N-tert-butyl-4-[[1-(2-cyanocycloheptyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]-N-methylbenzenesulfonamide Chemical compound C(C)(C)(C)N(S(=O)(=O)C1=CC=C(C=C1)NC1=NN(C2=C1C(NC=C2)=O)C2C(CCCCC2)C#N)C YGIVJNKHBGEKKY-UHFFFAOYSA-N 0.000 claims 1
- OFLKYUCVHVLYAM-UHFFFAOYSA-N N-tert-butyl-4-[[1-(2-cyanocyclohexyl)-4-oxo-5H-pyrazolo[4,3-c]pyridin-3-yl]amino]-N-methylbenzenesulfonamide Chemical compound CN(C(C)(C)C)S(=O)(=O)c1ccc(Nc2nn(C3CCCCC3C#N)c3cc[nH]c(=O)c23)cc1 OFLKYUCVHVLYAM-UHFFFAOYSA-N 0.000 claims 1
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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
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- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
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- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000005879 dioxolanyl group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
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- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
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- 125000001153 fluoro group Chemical group F* 0.000 claims 1
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- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
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| PCT/CN2013/072867 WO2014146246A1 (en) | 2013-03-19 | 2013-03-19 | Cycloalkyl nitrile pyrazolo pyridones as janus kinase inhibitors |
| CNPCT/CN2013/072867 | 2013-03-19 | ||
| PCT/CN2014/000296 WO2014146490A1 (en) | 2013-03-19 | 2014-03-19 | Cycloalkyl nitrile pyrazolo pyridones as janus kinase inhibitors |
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| JP2016518344A JP2016518344A (ja) | 2016-06-23 |
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| EP (1) | EP2976340B1 (OSRAM) |
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| RU (1) | RU2655380C2 (OSRAM) |
| TR (1) | TR201811198T4 (OSRAM) |
| WO (2) | WO2014146246A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12509463B2 (en) | 2019-01-30 | 2025-12-30 | Felicamed Biotechnology Co., Ltd. | JAK inhibitor and preparation method therefor |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2014234908B2 (en) * | 2013-03-19 | 2017-08-17 | Merck Sharp & Dohme Corp. | N-(2-cyano heterocyclyl)pyrazolo pyridones as Janus kinase inhibitors |
| AU2017233739A1 (en) | 2016-03-15 | 2018-09-20 | Bayer Cropscience Aktiengesellschaft | Substituted sulfonyl amides for controlling animal pests |
| TW201822637A (zh) | 2016-11-07 | 2018-07-01 | 德商拜耳廠股份有限公司 | 用於控制動物害蟲的經取代磺醯胺類 |
| EP3555074B1 (en) | 2016-12-14 | 2022-07-27 | Intervet International B.V. | Aminopyrazoles as selective janus kinase inhibitors |
| CA3127892A1 (en) * | 2019-01-30 | 2020-08-06 | Gargamel (Zhuhai) Biotech Ltd. | Jak inhibitor and preparation method thereof |
| US20220380318A1 (en) | 2019-11-07 | 2022-12-01 | Bayer Aktiengesellschaft | Substituted sulfonyl amides for controlling animal pests |
| CN113372364B (zh) * | 2020-03-10 | 2024-05-31 | 明慧医药（上海）有限公司 | 一类jak激酶抑制剂及其制备和应用 |
| AU2022418280A1 (en) | 2021-12-24 | 2024-06-13 | Intervet International B.V. | Use of aminopyrazole compounds |
| TW202345806A (zh) | 2022-03-31 | 2023-12-01 | 美商艾伯維有限公司 | 噻唑并〔５，４－ｂ〕吡啶ｍａｌｔ－１抑制劑 |
| CN116715656B (zh) * | 2022-07-26 | 2025-05-02 | 北京先通国际医药科技股份有限公司 | 心肌灌注显像剂前体的制备方法及其用途 |
| CN118561689B (zh) * | 2024-08-05 | 2024-11-22 | 中节能万润股份有限公司 | 一种3-氧代环丁羧酸酯类化合物的制备方法 |
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| EP2251341A1 (en) * | 2005-07-14 | 2010-11-17 | Astellas Pharma Inc. | Heterocyclic Janus kinase 3 inhibitors |
| KR20090106604A (ko) * | 2007-01-12 | 2009-10-09 | 아스텔라스세이야쿠 가부시키가이샤 | 축합 피리딘 화합물 |
| CA2698256A1 (en) * | 2007-09-11 | 2009-03-19 | Merck Sharp & Dohme Corp. | Inhibitors of janus kinases |
| EP2451813B1 (en) | 2009-07-08 | 2014-10-01 | Leo Pharma A/S | Heterocyclic compounds as jak receptor and protein tyrosine kinase inhibitors |
| AU2011224484A1 (en) * | 2010-03-10 | 2012-09-27 | Incyte Holdings Corporation | Piperidin-4-yl azetidine derivatives as JAK1 inhibitors |
| CA2830882C (en) * | 2011-03-22 | 2021-03-16 | Dinesh Barawkar | Substituted fused tricyclic compounds, compositions and medicinal applications thereof |
| EP2527344A1 (en) * | 2011-05-25 | 2012-11-28 | Almirall, S.A. | Pyridin-2(1H)-one derivatives useful as medicaments for the treatment of myeloproliferative disorders, transplant rejection, immune-mediated and inflammatory diseases |
| 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 |
| WO2014146249A1 (en) * | 2013-03-19 | 2014-09-25 | Merck Sharp & Dohme Corp. | Geminally substituted cyanoethylpyrazolo pyridones as janus kinase inhibitors |
| JP6305510B2 (ja) * | 2013-03-19 | 2018-04-04 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | ヤヌスキナーゼ阻害剤としての非環式シアノエチルピラゾロピリドン |
| AU2014234908B2 (en) * | 2013-03-19 | 2017-08-17 | Merck Sharp & Dohme Corp. | N-(2-cyano heterocyclyl)pyrazolo pyridones as Janus kinase inhibitors |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12509463B2 (en) | 2019-01-30 | 2025-12-30 | Felicamed Biotechnology Co., Ltd. | JAK inhibitor and preparation method therefor |
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