JP2017518326A5 - - Google Patents
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- JP2017518326A5 JP2017518326A5 JP2016573030A JP2016573030A JP2017518326A5 JP 2017518326 A5 JP2017518326 A5 JP 2017518326A5 JP 2016573030 A JP2016573030 A JP 2016573030A JP 2016573030 A JP2016573030 A JP 2016573030A JP 2017518326 A5 JP2017518326 A5 JP 2017518326A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- pyrazolo
- ethyl
- indolizin
- pyrimidin
- 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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- -1 3H-purin-3-yl Chemical group 0.000 claims description 141
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims 8
- 206010011224 Cough Diseases 0.000 claims 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000006709 (C5-C7) cycloalkenyl group Chemical group 0.000 claims 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 4
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 4
- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- SMSPJZGBTODFFP-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-[3-[(dimethylamino)methyl]phenyl]indolizine-1-carbonitrile Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=CC(=CC(=C1)O)F)C(C)C=1C(=C2C=CC=CN2C=1C1=CC(=CC=C1)CN(C)C)C#N SMSPJZGBTODFFP-UHFFFAOYSA-N 0.000 claims 3
- XQZIGBMAAJMDAN-UHFFFAOYSA-N 3-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 XQZIGBMAAJMDAN-UHFFFAOYSA-N 0.000 claims 3
- FTKFPUJIGJVOHP-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[3-[(dimethylamino)methyl]phenyl]indolizin-2-yl]ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2C=CC=CN2C=1C1=CC(=CC=C1)CN(C)C FTKFPUJIGJVOHP-UHFFFAOYSA-N 0.000 claims 3
- WGOFXIRSBXDCOB-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]indolizin-2-yl]ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2C=CC=CN2C=1C1=NC=C(C=C1)CN1CCN(CC1)C WGOFXIRSBXDCOB-UHFFFAOYSA-N 0.000 claims 3
- ULFPBCMWNKNLGW-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[5-[[bis(2-hydroxyethyl)amino]methyl]pyridin-2-yl]indolizin-2-yl]ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2C=CC=CN2C=1C1=NC=C(C=C1)CN(CCO)CCO ULFPBCMWNKNLGW-UHFFFAOYSA-N 0.000 claims 3
- NBFICFJEUMXPQC-UHFFFAOYSA-N 4-[2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]indolizin-3-yl]-1-(2-morpholin-4-ylethyl)pyridin-2-one Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=CC(=CC(=C1)O)F)C(C)C=1C=C2C=CC=CN2C=1C1=CC(N(C=C1)CCN1CCOCC1)=O NBFICFJEUMXPQC-UHFFFAOYSA-N 0.000 claims 3
- IUXXLROJLDTEQT-UHFFFAOYSA-N 4-[2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]indolizin-3-yl]-1-[2-(dimethylamino)ethyl]pyridin-2-one Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=CC(=CC(=C1)O)F)C(C)C=1C=C2C=CC=CN2C=1C1=CC(N(C=C1)CCN(C)C)=O IUXXLROJLDTEQT-UHFFFAOYSA-N 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 3
- 206010062106 Respiratory tract infection viral Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 208000014674 injury Diseases 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 3
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 2
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- NQMSWINNJOYTKY-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]indolizin-2-yl]ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2C=CC=CN2C=1C1=NC=C(C=C1)CN1CCOCC1 NQMSWINNJOYTKY-UHFFFAOYSA-N 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 108091007960 PI3Ks Proteins 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 230000007247 enzymatic mechanism Effects 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 230000000241 respiratory effect Effects 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 230000003612 virological effect Effects 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- ALUPHCBAOUBAGI-OPEKNORGSA-N (NE)-N-[[4-amino-6-[1-(3-pyridin-2-ylindolizin-2-yl)ethylamino]pyrimidin-5-yl]methylidene]hydroxylamine Chemical compound O\N=C\C=1C(=NC=NC=1N)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 ALUPHCBAOUBAGI-OPEKNORGSA-N 0.000 claims 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims 1
- UDKBTHABGBWSPH-UHFFFAOYSA-N 1-(2-morpholin-4-ylethyl)pyridin-2-one Chemical compound O=C1C=CC=CN1CCN1CCOCC1 UDKBTHABGBWSPH-UHFFFAOYSA-N 0.000 claims 1
- QCOWWVUQLLHHDY-UHFFFAOYSA-N 1-[2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]indolizin-3-yl]-4-methylpiperazin-2-one Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=CC(=CC(=C1)O)F)C(C)C=1C=C2C=CC=CN2C=1N1C(CN(CC1)C)=O QCOWWVUQLLHHDY-UHFFFAOYSA-N 0.000 claims 1
- ZUJHJNOOIKEXOE-UHFFFAOYSA-N 1-[2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]indolizin-3-yl]pyrrolidin-2-one Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=CC(=CC(=C1)O)F)C(C)C=1C=C2C=CC=CN2C=1N1C(CCC1)=O ZUJHJNOOIKEXOE-UHFFFAOYSA-N 0.000 claims 1
- XRMDCWJNPDVAFI-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[N+]1=O XRMDCWJNPDVAFI-UHFFFAOYSA-N 0.000 claims 1
- BISMMRXMISYAPR-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-(morpholin-4-ylmethyl)indolizine-1-carbonitrile Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=CC(=CC(=C1)O)F)C(C)C=1C(=C2C=CC=CN2C=1CN1CCOCC1)C#N BISMMRXMISYAPR-UHFFFAOYSA-N 0.000 claims 1
- UXEDXFZCKRXEGH-UHFFFAOYSA-N 2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-3-pyridin-2-ylindolizine-1-carbonitrile Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=CC(=CC(=C1)O)F)C(C)C=1C(=C2C=CC=CN2C=1C1=NC=CC=C1)C#N UXEDXFZCKRXEGH-UHFFFAOYSA-N 0.000 claims 1
- CVVXUHXCPHZJQU-UHFFFAOYSA-N 2-[2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]indolizin-3-yl]benzonitrile Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=CC(=CC(=C1)O)F)C(C)C=1C=C2C=CC=CN2C=1C1=C(C#N)C=CC=C1 CVVXUHXCPHZJQU-UHFFFAOYSA-N 0.000 claims 1
- HOPXFKDWTZAVSO-UHFFFAOYSA-N 3-(3-fluoro-5-methoxyphenyl)-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound FC=1C=C(C=C(C=1)OC)C1=NN(C2=NC=NC(=C21)N)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 HOPXFKDWTZAVSO-UHFFFAOYSA-N 0.000 claims 1
- OBAOSKCZHKWZPL-UHFFFAOYSA-N 3-(3-fluorophenyl)-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound FC=1C=C(C=CC=1)C1=NN(C2=NC=NC(=C21)N)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 OBAOSKCZHKWZPL-UHFFFAOYSA-N 0.000 claims 1
- SVHXKZJVBJDHEX-CTXDPNEZSA-N 3-[1-[1-[3-[[(3aR,6aS)-2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]methyl]indolizin-2-yl]ethyl]-4-aminopyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound CN1C[C@@H]2[C@H](C1)CN(C2)CC1=C(C=C2C=CC=CN12)C(C)N1N=C(C=2C1=NC=NC=2N)C=1C=C(C=C(C=1)F)O SVHXKZJVBJDHEX-CTXDPNEZSA-N 0.000 claims 1
- SZGHAXXIYBAPNK-UHFFFAOYSA-N 3-[4-amino-1-[(3-pyridin-2-ylindolizin-2-yl)methyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)CC=1C=C2C=CC=CN2C=1C1=NC=CC=C1 SZGHAXXIYBAPNK-UHFFFAOYSA-N 0.000 claims 1
- SXKLHJOUZBEQLK-UHFFFAOYSA-N 3-[4-amino-1-[(3-pyridin-3-ylindolizin-2-yl)methyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)CC=1C=C2C=CC=CN2C=1C=1C=NC=CC=1 SXKLHJOUZBEQLK-UHFFFAOYSA-N 0.000 claims 1
- CGBLOJQNWPFMSR-UHFFFAOYSA-N 3-[4-amino-1-[(3-pyridin-4-ylindolizin-2-yl)methyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)CC=1C=C2C=CC=CN2C=1C1=CC=NC=C1 CGBLOJQNWPFMSR-UHFFFAOYSA-N 0.000 claims 1
- NQICHPUBKIPKDN-UHFFFAOYSA-N 3-[4-amino-1-[(7-pyridin-2-ylpyrrolo[1,2-b]pyridazin-6-yl)methyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)CC=1C=C2N(N=CC=C2)C=1C1=NC=CC=C1 NQICHPUBKIPKDN-UHFFFAOYSA-N 0.000 claims 1
- FWEQVSGRVOPLEJ-UHFFFAOYSA-N 3-[4-amino-1-[1-(1-methyl-3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C(=C2C=CC=CN2C=1C1=NC=CC=C1)C FWEQVSGRVOPLEJ-UHFFFAOYSA-N 0.000 claims 1
- WDTYOFMXFANFDU-UHFFFAOYSA-N 3-[4-amino-1-[1-(3-phenylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2C=CC=CN2C=1C1=CC=CC=C1 WDTYOFMXFANFDU-UHFFFAOYSA-N 0.000 claims 1
- QCBTZJKIGDQRSL-UHFFFAOYSA-N 3-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-(trifluoromethyl)phenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)C(F)(F)F)O)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 QCBTZJKIGDQRSL-UHFFFAOYSA-N 0.000 claims 1
- QNYFAYIPFMHVBN-UHFFFAOYSA-N 3-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-chlorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)Cl)O)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 QNYFAYIPFMHVBN-UHFFFAOYSA-N 0.000 claims 1
- GWWUUEAIGYYREE-UHFFFAOYSA-N 3-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorobenzenesulfonamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)S(=O)(=O)N)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 GWWUUEAIGYYREE-UHFFFAOYSA-N 0.000 claims 1
- VDVIQHWZGATIFT-UHFFFAOYSA-N 3-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-hydroxybenzonitrile Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C#N)C=C(C=1)O)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 VDVIQHWZGATIFT-UHFFFAOYSA-N 0.000 claims 1
- RORBWKNADQEFMU-UHFFFAOYSA-N 3-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]benzenesulfonamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=CC=1)S(=O)(=O)N)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 RORBWKNADQEFMU-UHFFFAOYSA-N 0.000 claims 1
- AXSDJCWSPITBBH-UHFFFAOYSA-N 3-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=CC=1)O)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 AXSDJCWSPITBBH-UHFFFAOYSA-N 0.000 claims 1
- OBLVELXYJRNMFK-UHFFFAOYSA-N 3-[4-amino-1-[1-(3-pyridin-4-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2C=CC=CN2C=1C1=CC=NC=C1 OBLVELXYJRNMFK-UHFFFAOYSA-N 0.000 claims 1
- MLDUHDBKBRTEMB-UHFFFAOYSA-N 3-[4-amino-1-[1-(6-methyl-3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2C=CC(=CN2C=1C1=NC=CC=C1)C MLDUHDBKBRTEMB-UHFFFAOYSA-N 0.000 claims 1
- AZABZSCFRCGZOF-UHFFFAOYSA-N 3-[4-amino-1-[1-(7-chloro-3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2C=C(C=CN2C=1C1=NC=CC=C1)Cl AZABZSCFRCGZOF-UHFFFAOYSA-N 0.000 claims 1
- KLUCHNTYBFDTCS-UHFFFAOYSA-N 3-[4-amino-1-[1-(7-methyl-3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2C=C(C=CN2C=1C1=NC=CC=C1)C KLUCHNTYBFDTCS-UHFFFAOYSA-N 0.000 claims 1
- YIEONKPPZYOSRS-UHFFFAOYSA-N 3-[4-amino-1-[1-(7-pyridin-2-ylpyrrolo[1,2-b]pyridazin-6-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2N(N=CC=C2)C=1C1=NC=CC=C1 YIEONKPPZYOSRS-UHFFFAOYSA-N 0.000 claims 1
- KGYZYKRTYVUXDV-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-(1,2,3,6-tetrahydropyridin-4-yl)indolizin-2-yl]ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)O)C(C)C=1C=C2C=CC=CN2C=1C=1CCNCC=1 KGYZYKRTYVUXDV-UHFFFAOYSA-N 0.000 claims 1
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| EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| KR101815193B1 (ko) * | 2015-12-29 | 2018-01-30 | (주)스파크바이오파마 | PPARγ 인산화 저해제 및 이를 포함하는 약학적 조성물 |
| US10787433B2 (en) | 2016-01-15 | 2020-09-29 | The Brigham And Women's Hospital, Inc. | Pyridazine derivatives as EAAT2 activators |
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| CN109963854B (zh) | 2017-03-16 | 2022-04-12 | 江苏恒瑞医药股份有限公司 | 杂芳基并[4,3-c]嘧啶-5-胺类衍生物、其制备方法及其在医药上的应用 |
| CN108129480A (zh) * | 2018-03-11 | 2018-06-08 | 赵艳阳 | 一种含芳杂环亚甲基吲嗪衍生物的制备方法 |
| CA3102762A1 (en) | 2018-06-04 | 2019-12-12 | Ohio State Innovation Foundation | Eaat2 activators and methods of using thereof |
| WO2020200918A1 (en) * | 2019-04-04 | 2020-10-08 | Chiesi Farmaceutici S.P.A. | Isochromene derivatives as phosphoinositide 3-kinases inhibitors |
| CN110156785B (zh) * | 2019-04-15 | 2020-08-28 | 浙江大学 | 吲唑类化合物及其制备方法和应用 |
| AU2020299632A1 (en) * | 2019-07-03 | 2022-02-17 | Sanford Burnham Prebys Medical Discovery Institute | Inhibitors of low molecular weight protein tyrosine phosphatase (LMPTP) and uses thereof |
| CA3154079A1 (en) | 2019-09-19 | 2021-03-25 | Totus Medicines Inc. | Therapeutic conjugates |
| US20250002491A1 (en) | 2021-10-04 | 2025-01-02 | Forx Therapeutics Ag | N,n-dimethyl-4-(7-(n-(1-methylcyclopropyl)sulfamoyl)-imidazo[1,5-a]pyridin-5-yl)piperazine-1-carboxamide derivatives and the corresponding pyrazolo[1,5-a]pyridine derivatives as parg inhibitors for the treatment of cancer |
| KR102866487B1 (ko) | 2023-01-06 | 2025-10-01 | 연세대학교 산학협력단 | 새로운 인돌리진-피롤로피리미딘 하이브리드 유도체 제조방법 및 이를 포함하는 항암제 조성물 |
| WO2024186827A2 (en) * | 2023-03-06 | 2024-09-12 | The Regents Of The University Of California | Novel host-directed therapeutic agent for the treatment of infectious diseases |
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| US8063071B2 (en) | 2007-10-31 | 2011-11-22 | GlaxoSmithKline, LLC | Chemical compounds |
| JP5552121B2 (ja) * | 2008-09-04 | 2014-07-16 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロイコトリエン産生のインドリジン阻害剤 |
| AR077428A1 (es) * | 2009-07-29 | 2011-08-24 | Sanofi Aventis | (aza) indolizinacarboxamidas ciclicas su preparacion y su uso como agentes farmaceuticos |
| US8759359B2 (en) | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| EP2571357B1 (en) | 2010-05-21 | 2016-07-06 | Infinity Pharmaceuticals, Inc. | Chemical compounds, compositions and methods for kinase modulation |
| JP6026544B2 (ja) * | 2011-09-27 | 2016-11-16 | ノバルティス アーゲー | 変異体ｉｄｈの阻害剤としての３−ピリミジン−４−イル−オキサゾリジン−２−オン類 |
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