JP2017518326A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- -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
- GHKYQSIPCSPGNX-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-(1,3-thiazol-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=1N=CSC=1 GHKYQSIPCSPGNX-UHFFFAOYSA-N 0.000 claims 1
- QZGHWFCJLYDOBI-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-(1,3-thiazol-5-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=CN=CS1 QZGHWFCJLYDOBI-UHFFFAOYSA-N 0.000 claims 1
- KAMOFOASAAPREY-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-(2-fluorophenyl)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=C(C=CC=C1)F KAMOFOASAAPREY-UHFFFAOYSA-N 0.000 claims 1
- OLUZZVYKMDCHTA-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-(2-methylpyridin-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=1C1=CC(=NC=C1)C OLUZZVYKMDCHTA-UHFFFAOYSA-N 0.000 claims 1
- YYXAJTDZWOEUMJ-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-(morpholin-4-ylmethyl)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=1CN1CCOCC1 YYXAJTDZWOEUMJ-UHFFFAOYSA-N 0.000 claims 1
- JFERLYGMAFCWBY-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[(2-methyl-2,9-diazaspiro[5.5]undecan-9-yl)methyl]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=1CN1CCC2(CCCN(C2)C)CC1 JFERLYGMAFCWBY-UHFFFAOYSA-N 0.000 claims 1
- HPILLOOFYGGMKK-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[(7-methyl-2,7-diazaspiro[3.5]nonan-2-yl)methyl]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=1CN1CC2(C1)CCN(CC2)C HPILLOOFYGGMKK-UHFFFAOYSA-N 0.000 claims 1
- ZVKGKCTZSQYLKC-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[(9-methyl-3,9-diazaspiro[5.5]undecan-3-yl)methyl]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=1CN1CCC2(CC1)CCN(CC2)C ZVKGKCTZSQYLKC-UHFFFAOYSA-N 0.000 claims 1
- GTRJUJYWRYRVCQ-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[1-(2-morpholin-4-ylethyl)pyrazol-3-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=NN(C=C1)CCN1CCOCC1 GTRJUJYWRYRVCQ-UHFFFAOYSA-N 0.000 claims 1
- SUNAFVVMEGQULY-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[1-[2-(4-methylpiperazin-1-yl)ethyl]pyrazol-3-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=NN(C=C1)CCN1CCN(CC1)C SUNAFVVMEGQULY-UHFFFAOYSA-N 0.000 claims 1
- DOIXNSREQFBLEI-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[1-[2-(dimethylamino)ethyl]pyrazol-3-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=NN(C=C1)CCN(C)C DOIXNSREQFBLEI-UHFFFAOYSA-N 0.000 claims 1
- WMQBLBVCTKNXHX-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[1-[2-[bis(2-hydroxyethyl)amino]ethyl]pyrazol-3-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=NN(C=C1)CCN(CCO)CCO WMQBLBVCTKNXHX-UHFFFAOYSA-N 0.000 claims 1
- JWWKBKBMQVSCDT-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[2-(morpholin-4-ylmethyl)-1,3-thiazol-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=1N=C(SC=1)CN1CCOCC1 JWWKBKBMQVSCDT-UHFFFAOYSA-N 0.000 claims 1
- ILDXVPVHJAZUQD-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[3-(1-methylpyrrolidin-2-yl)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)C1N(CCC1)C ILDXVPVHJAZUQD-UHFFFAOYSA-N 0.000 claims 1
- NWCPENXOQRHFDH-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[4-(morpholin-4-ylmethyl)phenyl]indolizin-2-yl]ethyl]indazol-3-yl]-5-fluorophenol Chemical compound NC1=C2C(=NN(C2=CC=C1)C(C)C=1C=C2C=CC=CN2C=1C1=CC=C(C=C1)CN1CCOCC1)C=1C=C(C=C(C=1)F)O NWCPENXOQRHFDH-UHFFFAOYSA-N 0.000 claims 1
- WTMCVYGJKXUCFR-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[4-(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=CC(=C1)CN1CCOCC1 WTMCVYGJKXUCFR-UHFFFAOYSA-N 0.000 claims 1
- MYYVZMBDVLAFCI-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[4-[(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=CC(=C1)CN1CCN(CC1)C MYYVZMBDVLAFCI-UHFFFAOYSA-N 0.000 claims 1
- RKULABCJEDESIZ-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[4-[(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=C(C=C1)CN(C)C RKULABCJEDESIZ-UHFFFAOYSA-N 0.000 claims 1
- ODMMKZPTSMDTPO-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[4-[(dimethylamino)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=CC(=C1)CN(C)C ODMMKZPTSMDTPO-UHFFFAOYSA-N 0.000 claims 1
- LCCYYNMCSCMUQN-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[5-(2-morpholin-4-ylethoxy)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)OCCN1CCOCC1 LCCYYNMCSCMUQN-UHFFFAOYSA-N 0.000 claims 1
- BDEHNUIUOOLMBA-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[5-(morpholin-4-ylmethyl)thiophen-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=1C=1SC(=CC=1)CN1CCOCC1 BDEHNUIUOOLMBA-UHFFFAOYSA-N 0.000 claims 1
- VPFSVHYFVUKDMR-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[5-(pyrrolidin-1-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)CN1CCCC1 VPFSVHYFVUKDMR-UHFFFAOYSA-N 0.000 claims 1
- JRIBMLSJVZXNFN-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[5-[(dimethylamino)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(C)C JRIBMLSJVZXNFN-UHFFFAOYSA-N 0.000 claims 1
- QCSOHEIWJNVUCV-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[6-(1-methylpiperidin-4-yl)oxypyridazin-3-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=1N=NC(=CC=1)OC1CCN(CC1)C QCSOHEIWJNVUCV-UHFFFAOYSA-N 0.000 claims 1
- GJOGVVHEERVDBL-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[6-(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(=CC=C1)CN1CCOCC1 GJOGVVHEERVDBL-UHFFFAOYSA-N 0.000 claims 1
- GANYAAHMLWOTSG-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[6-[(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(=CC=C1)CN1CCN(CC1)C GANYAAHMLWOTSG-UHFFFAOYSA-N 0.000 claims 1
- KFZISIFIJYSPFI-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[6-[2-(1-methylpiperidin-4-yl)ethoxy]pyridazin-3-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=1N=NC(=CC=1)OCCC1CCN(CC1)C KFZISIFIJYSPFI-UHFFFAOYSA-N 0.000 claims 1
- XRTIWPFQLYFTPZ-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[6-[2-(4-methylpiperazin-1-yl)ethoxy]pyridazin-3-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=1N=NC(=CC=1)OCCN1CCN(CC1)C XRTIWPFQLYFTPZ-UHFFFAOYSA-N 0.000 claims 1
- LXNGHBBHCVEKBZ-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-[6-[2-(dimethylamino)ethoxy]pyridazin-3-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=1N=NC(=CC=1)OCCN(C)C LXNGHBBHCVEKBZ-UHFFFAOYSA-N 0.000 claims 1
- WVGWCEJBSGPDHA-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-pyridin-2-yl-1-(trifluoromethyl)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=CC=C1)C(F)(F)F WVGWCEJBSGPDHA-UHFFFAOYSA-N 0.000 claims 1
- ZBAXBRIRGABAEW-UHFFFAOYSA-N 3-[4-amino-1-[1-[3-pyridin-2-yl-6-(trifluoromethyl)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=CC=C1)C(F)(F)F ZBAXBRIRGABAEW-UHFFFAOYSA-N 0.000 claims 1
- YVMADEYJLRGOTM-UHFFFAOYSA-N 3-[4-amino-6-[1-(3-pyridin-2-ylindolizin-2-yl)ethylamino]pyrimidin-5-yl]prop-2-yn-1-ol Chemical compound NC1=NC=NC(=C1C#CCO)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 YVMADEYJLRGOTM-UHFFFAOYSA-N 0.000 claims 1
- YJPZNSCHODNLJB-UHFFFAOYSA-N 3-amino-N-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC=CN=1)C(=O)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 YJPZNSCHODNLJB-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- PVBVQNRJGOUPQR-UHFFFAOYSA-N 3-phenyl-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1(=CC=CC=C1)C1=NN(C2=NC=NC(=C21)N)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 PVBVQNRJGOUPQR-UHFFFAOYSA-N 0.000 claims 1
- XYEASLCAJOINCA-UHFFFAOYSA-N 3-pyridin-3-yl-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C=CC=C1)C1=C(C=C2C=CC=CN12)C(C)N1N=C(C=2C1=NC=NC=2N)C=1C=NC=CC=1 XYEASLCAJOINCA-UHFFFAOYSA-N 0.000 claims 1
- MUGSKSNNEORSJG-UHFFFAOYSA-N 3174-74-1 Chemical compound C1CC=CCO1 MUGSKSNNEORSJG-UHFFFAOYSA-N 0.000 claims 1
- NPHUCUJOXFXSRP-UHFFFAOYSA-N 4-N-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]-5-(trifluoromethyl)pyrimidine-4,6-diamine Chemical compound N1=C(C=CC=C1)C1=C(C=C2C=CC=CN12)C(C)NC1=NC=NC(=C1C(F)(F)F)N NPHUCUJOXFXSRP-UHFFFAOYSA-N 0.000 claims 1
- CCALNKPIVBGPQO-UHFFFAOYSA-N 4-[2-[1-[4-amino-3-(5-hydroxypyridin-3-yl)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=C2C=1C=NC=C(C=1)O)C(C)C=1C=C2C=CC=CN2C=1C1=CC(N(C=C1)CCN1CCOCC1)=O CCALNKPIVBGPQO-UHFFFAOYSA-N 0.000 claims 1
- XUTWEGKTQVRMGQ-UHFFFAOYSA-N 4-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-2-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=CC(=C(C=C1)O)F)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 XUTWEGKTQVRMGQ-UHFFFAOYSA-N 0.000 claims 1
- NNGBQDSTAMAHJZ-UHFFFAOYSA-N 4-amino-6-(indolizin-2-ylmethylamino)pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NCC=1C=C2C=CC=CN2C=1 NNGBQDSTAMAHJZ-UHFFFAOYSA-N 0.000 claims 1
- JKLNFPRETDYTGY-UHFFFAOYSA-N 4-amino-6-[(1-phenylindolizin-2-yl)methylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NCC=1C(=C2C=CC=CN2C=1)C1=CC=CC=C1 JKLNFPRETDYTGY-UHFFFAOYSA-N 0.000 claims 1
- DWWWNYUIWWYBCK-UHFFFAOYSA-N 4-amino-6-[(1-pyridin-2-ylindolizin-2-yl)methylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NCC=1C(=C2C=CC=CN2C=1)C1=NC=CC=C1 DWWWNYUIWWYBCK-UHFFFAOYSA-N 0.000 claims 1
- SOCSBFBVZVLELS-UHFFFAOYSA-N 4-amino-6-[(3-phenylindolizin-2-yl)methylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NCC=1C=C2C=CC=CN2C=1C1=CC=CC=C1 SOCSBFBVZVLELS-UHFFFAOYSA-N 0.000 claims 1
- XVZSDTCCLNPSJO-UHFFFAOYSA-N 4-amino-6-[(3-pyridin-2-ylindolizin-2-yl)methylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NCC=1C=C2C=CC=CN2C=1C1=NC=CC=C1 XVZSDTCCLNPSJO-UHFFFAOYSA-N 0.000 claims 1
- FVFHRMOJEVPZJI-UHFFFAOYSA-N 4-amino-6-[1-(3-pent-1-ynylindolizin-2-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=CN2C=1C#CCCC FVFHRMOJEVPZJI-UHFFFAOYSA-N 0.000 claims 1
- LQPOBXWZSUZGKG-UHFFFAOYSA-N 4-amino-6-[1-(3-phenylindolizin-2-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=CN2C=1C1=CC=CC=C1 LQPOBXWZSUZGKG-UHFFFAOYSA-N 0.000 claims 1
- QUFPLYLRFHEVDW-UHFFFAOYSA-N 4-amino-6-[1-(3-pyrazin-2-ylindolizin-2-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CN=C1 QUFPLYLRFHEVDW-UHFFFAOYSA-N 0.000 claims 1
- VXKHBIZHFXRQSO-UHFFFAOYSA-N 4-amino-6-[1-(3-pyridin-2-ylindolizin-2-yl)ethylamino]pyrimidine-5-carbaldehyde Chemical compound NC1=NC=NC(=C1C=O)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 VXKHBIZHFXRQSO-UHFFFAOYSA-N 0.000 claims 1
- ULEOXBUVTVKZIS-UHFFFAOYSA-N 4-amino-6-[1-(3-pyridin-2-ylindolizin-2-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 ULEOXBUVTVKZIS-UHFFFAOYSA-N 0.000 claims 1
- VCDYCOPYICGTKV-UHFFFAOYSA-N 4-amino-6-[1-(3-pyridin-2-ylindolizin-2-yl)ethylamino]pyrimidine-5-carboxamide Chemical compound NC1=NC=NC(=C1C(=O)N)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 VCDYCOPYICGTKV-UHFFFAOYSA-N 0.000 claims 1
- YCPCQHDROBZVDC-UHFFFAOYSA-N 4-amino-6-[1-(3-pyridin-2-ylindolizin-2-yl)ethylamino]pyrimidine-5-carboxylic acid Chemical compound NC1=NC=NC(=C1C(=O)O)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 YCPCQHDROBZVDC-UHFFFAOYSA-N 0.000 claims 1
- RTVQKTUWXNUBIN-UHFFFAOYSA-N 4-amino-6-[1-(3-pyridin-2-ylindolizin-2-yl)propylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(CC)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 RTVQKTUWXNUBIN-UHFFFAOYSA-N 0.000 claims 1
- RRLFVJJIMVJFMV-UHFFFAOYSA-N 4-amino-6-[1-(3-pyridin-3-ylindolizin-2-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=CN2C=1C=1C=NC=CC=1 RRLFVJJIMVJFMV-UHFFFAOYSA-N 0.000 claims 1
- IJVXCEOUPOCFOP-UHFFFAOYSA-N 4-amino-6-[1-(3-pyridin-4-ylindolizin-2-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=CN2C=1C1=CC=NC=C1 IJVXCEOUPOCFOP-UHFFFAOYSA-N 0.000 claims 1
- QBVIUKCSSKRNDB-UHFFFAOYSA-N 4-amino-6-[1-(3-thiophen-2-ylindolizin-2-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=CN2C=1C=1SC=CC=1 QBVIUKCSSKRNDB-UHFFFAOYSA-N 0.000 claims 1
- RIMWXDAWJNCAQU-UHFFFAOYSA-N 4-amino-6-[1-(3-thiophen-3-ylindolizin-2-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=CN2C=1C1=CSC=C1 RIMWXDAWJNCAQU-UHFFFAOYSA-N 0.000 claims 1
- KISNUPQXDUDESZ-UHFFFAOYSA-N 4-amino-6-[1-(5-methyl-3-pyridin-2-ylindolizin-2-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=C(N2C=1C1=NC=CC=C1)C KISNUPQXDUDESZ-UHFFFAOYSA-N 0.000 claims 1
- PNBFMEQQWPXVDD-UHFFFAOYSA-N 4-amino-6-[1-(8-fluoro-3-pyridin-2-ylindolizin-2-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C(=CC=CN2C=1C1=NC=CC=C1)F PNBFMEQQWPXVDD-UHFFFAOYSA-N 0.000 claims 1
- HEIAMQOQGJIRRK-UHFFFAOYSA-N 4-amino-6-[1-(8-methyl-3-pyridin-2-ylindolizin-2-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C(=CC=CN2C=1C1=NC=CC=C1)C HEIAMQOQGJIRRK-UHFFFAOYSA-N 0.000 claims 1
- XOTRJTOHEPAQHI-UHFFFAOYSA-N 4-amino-6-[1-[3-(1,2,3,6-tetrahydropyridin-4-yl)indolizin-2-yl]ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=CN2C=1C=1CCNCC=1 XOTRJTOHEPAQHI-UHFFFAOYSA-N 0.000 claims 1
- NHNFODGCPUMWNF-UHFFFAOYSA-N 4-amino-6-[1-[3-(3,6-dihydro-2H-pyran-4-yl)indolizin-2-yl]ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=CN2C=1C=1CCOCC=1 NHNFODGCPUMWNF-UHFFFAOYSA-N 0.000 claims 1
- LAIDJSNFFKOSGR-UHFFFAOYSA-N 4-amino-6-[1-[3-(3-hydroxyprop-1-ynyl)indolizin-2-yl]ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NC(C)C=1C=C2C=CC=CN2C=1C#CCO LAIDJSNFFKOSGR-UHFFFAOYSA-N 0.000 claims 1
- GODVUPLMUWELNK-UHFFFAOYSA-N 4-amino-6-[[1-(2-methylphenyl)indolizin-2-yl]methylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NCC=1C(=C2C=CC=CN2C=1)C1=C(C=CC=C1)C GODVUPLMUWELNK-UHFFFAOYSA-N 0.000 claims 1
- PRDFQZUJXARUBZ-UHFFFAOYSA-N 4-amino-6-[[1-(3-fluorophenyl)indolizin-2-yl]methylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NCC=1C(=C2C=CC=CN2C=1)C1=CC(=CC=C1)F PRDFQZUJXARUBZ-UHFFFAOYSA-N 0.000 claims 1
- UEFZHMJQSKPQAQ-UHFFFAOYSA-N 4-amino-6-[[3-(2-fluorophenyl)indolizin-2-yl]methylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NCC=1C=C2C=CC=CN2C=1C1=C(C=CC=C1)F UEFZHMJQSKPQAQ-UHFFFAOYSA-N 0.000 claims 1
- VMLDNGJOJPYDAQ-UHFFFAOYSA-N 4-amino-6-[[3-(2-methylphenyl)indolizin-2-yl]methylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NCC=1C=C2C=CC=CN2C=1C1=C(C=CC=C1)C VMLDNGJOJPYDAQ-UHFFFAOYSA-N 0.000 claims 1
- JRIBFGXUZMWSPM-UHFFFAOYSA-N 4-amino-6-[[3-(3-fluorophenyl)indolizin-2-yl]methylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC(=C1C#N)NCC=1C=C2C=CC=CN2C=1C1=CC(=CC=C1)F JRIBFGXUZMWSPM-UHFFFAOYSA-N 0.000 claims 1
- HWUIYFXHXQLWFH-UHFFFAOYSA-N 4-amino-N-methyl-6-[1-(3-pyridin-2-ylindolizin-2-yl)ethylamino]pyrimidine-5-carboxamide Chemical compound NC1=NC=NC(=C1C(=O)NC)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 HWUIYFXHXQLWFH-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- QSUPTQRIHVZVFY-UHFFFAOYSA-N 5-(morpholin-4-ylmethyl)-4-N-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrimidine-4,6-diamine Chemical compound N1(CCOCC1)CC=1C(=NC=NC=1N)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 QSUPTQRIHVZVFY-UHFFFAOYSA-N 0.000 claims 1
- URKGAJSHGMNQQR-UHFFFAOYSA-N 5-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-2-fluorophenol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=CC(=C(C=1)O)F)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 URKGAJSHGMNQQR-UHFFFAOYSA-N 0.000 claims 1
- HHCUIPVBVJIJGD-UHFFFAOYSA-N 5-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]pyridin-3-ol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=NC=1)O)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 HHCUIPVBVJIJGD-UHFFFAOYSA-N 0.000 claims 1
- BOEMPEHXKDJIFU-UHFFFAOYSA-N 5-[4-amino-1-[1-[3-(2-methylpyridin-4-yl)indolizin-2-yl]ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]pyridin-3-ol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=NC=1)O)C(C)C=1C=C2C=CC=CN2C=1C1=CC(=NC=C1)C BOEMPEHXKDJIFU-UHFFFAOYSA-N 0.000 claims 1
- VGRMZASJJRTPDI-UHFFFAOYSA-N 5-bromo-4-N-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrimidine-4,6-diamine Chemical compound BrC=1C(=NC=NC=1N)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 VGRMZASJJRTPDI-UHFFFAOYSA-N 0.000 claims 1
- PQSUVOBITMGLLM-UHFFFAOYSA-N 5-methyl-4-N-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrimidine-4,6-diamine Chemical compound CC=1C(=NC=NC=1N)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 PQSUVOBITMGLLM-UHFFFAOYSA-N 0.000 claims 1
- MNWOXYSLKFKBQI-UHFFFAOYSA-N 6-[2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]indolizin-3-yl]-2-(2-pyrrolidin-1-ylethyl)pyridazin-3-one Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=CC(=CC(=C1)O)F)C(C)C=1C=C2C=CC=CN2C=1C=1C=CC(N(N=1)CCN1CCCC1)=O MNWOXYSLKFKBQI-UHFFFAOYSA-N 0.000 claims 1
- YOXWCAWMADHVCQ-UHFFFAOYSA-N 6-[2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]indolizin-3-yl]-2-[2-(4-methylpiperazin-1-yl)ethyl]pyridazin-3-one Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=CC(=CC(=C1)O)F)C(C)C=1C=C2C=CC=CN2C=1C=1C=CC(N(N=1)CCN1CCN(CC1)C)=O YOXWCAWMADHVCQ-UHFFFAOYSA-N 0.000 claims 1
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 1
- JYONZQQMDDSZIK-UHFFFAOYSA-N 9-(indolizin-2-ylmethyl)purin-6-amine Chemical compound C=1C(=CN2C=CC=CC=12)CN1C2=NC=NC(=C2N=C1)N JYONZQQMDDSZIK-UHFFFAOYSA-N 0.000 claims 1
- TYADNVJKMDGJEN-UHFFFAOYSA-N 9-[(1-phenylindolizin-2-yl)methyl]purin-6-amine Chemical compound C1(=CC=CC=C1)C=1C(=CN2C=CC=CC=12)CN1C2=NC=NC(=C2N=C1)N TYADNVJKMDGJEN-UHFFFAOYSA-N 0.000 claims 1
- HUPYGVPHFNOHQV-UHFFFAOYSA-N 9-[(3-phenylindolizin-2-yl)methyl]purin-6-amine Chemical compound C1(=CC=CC=C1)C1=C(C=C2C=CC=CN12)CN1C2=NC=NC(=C2N=C1)N HUPYGVPHFNOHQV-UHFFFAOYSA-N 0.000 claims 1
- LIUQPPIEDIHETE-UHFFFAOYSA-N 9-[(3-pyridin-2-ylindolizin-2-yl)methyl]purin-6-amine Chemical compound N1=C(C=CC=C1)C1=C(C=C2C=CC=CN12)CN1C2=NC=NC(=C2N=C1)N LIUQPPIEDIHETE-UHFFFAOYSA-N 0.000 claims 1
- HMPQFJCMTNLMKC-UHFFFAOYSA-N 9-[[1-(2-methylphenyl)indolizin-2-yl]methyl]purin-6-amine Chemical compound CC1=C(C=CC=C1)C=1C(=CN2C=CC=CC=12)CN1C2=NC=NC(=C2N=C1)N HMPQFJCMTNLMKC-UHFFFAOYSA-N 0.000 claims 1
- DINRFZPBBHNGAN-UHFFFAOYSA-N 9-[[1-(3-fluorophenyl)indolizin-2-yl]methyl]purin-6-amine Chemical compound FC=1C=C(C=CC=1)C=1C(=CN2C=CC=CC=12)CN1C2=NC=NC(=C2N=C1)N DINRFZPBBHNGAN-UHFFFAOYSA-N 0.000 claims 1
- JTTPWXHZRHACCR-UHFFFAOYSA-N 9-[[3-(2-fluorophenyl)indolizin-2-yl]methyl]purin-6-amine Chemical compound FC1=C(C=CC=C1)C1=C(C=C2C=CC=CN12)CN1C2=NC=NC(=C2N=C1)N JTTPWXHZRHACCR-UHFFFAOYSA-N 0.000 claims 1
- PQHJJZLTNXZGSP-UHFFFAOYSA-N 9-[[3-(2-methylphenyl)indolizin-2-yl]methyl]purin-6-amine Chemical compound CC1=C(C=CC=C1)C1=C(C=C2C=CC=CN12)CN1C2=NC=NC(=C2N=C1)N PQHJJZLTNXZGSP-UHFFFAOYSA-N 0.000 claims 1
- SRPUQEAPOUWTGT-UHFFFAOYSA-N 9-[[3-(3-fluorophenyl)indolizin-2-yl]methyl]purin-6-amine Chemical compound FC=1C=C(C=CC=1)C1=C(C=C2C=CC=CN12)CN1C2=NC=NC(=C2N=C1)N SRPUQEAPOUWTGT-UHFFFAOYSA-N 0.000 claims 1
- 241000228212 Aspergillus Species 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000008035 Back Pain Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- SGZKPNUBJWPDGB-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(C=C2C=CC=CN12)CN1C=NC(=C2N=CN=C12)N Chemical compound C1(=CC=CC=C1)C1=C(C=C2C=CC=CN12)CN1C=NC(=C2N=CN=C12)N SGZKPNUBJWPDGB-UHFFFAOYSA-N 0.000 claims 1
- GGCAXKGPXJSROC-UHFFFAOYSA-N CC1=C(C=CC=C1)C1=C(C=C2C=CC=CN12)CN1C=NC(=C2N=CN=C12)N Chemical compound CC1=C(C=CC=C1)C1=C(C=C2C=CC=CN12)CN1C=NC(=C2N=CN=C12)N GGCAXKGPXJSROC-UHFFFAOYSA-N 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- RMZIMKVEFJQTTJ-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1=C(C=C2C=CC=CN12)CN1C=NC(=C2N=CN=C12)N Chemical compound FC=1C=C(C=CC=1)C1=C(C=C2C=CC=CN12)CN1C=NC(=C2N=CN=C12)N RMZIMKVEFJQTTJ-UHFFFAOYSA-N 0.000 claims 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 1
- 208000004554 Leishmaniasis Diseases 0.000 claims 1
- 208000004852 Lung Injury Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000034486 Multi-organ failure Diseases 0.000 claims 1
- 208000010718 Multiple Organ Failure Diseases 0.000 claims 1
- RGHNPWRTBKLCEU-UHFFFAOYSA-N N-(indolizin-2-ylmethyl)-7H-purin-6-amine Chemical compound C=1C(=CN2C=CC=CC=12)CNC1=C2N=CNC2=NC=N1 RGHNPWRTBKLCEU-UHFFFAOYSA-N 0.000 claims 1
- LLGCZKLHOPOIBI-UHFFFAOYSA-N N-[(1-phenylindolizin-2-yl)methyl]-7H-purin-6-amine Chemical compound C1(=CC=CC=C1)C=1C(=CN2C=CC=CC=12)CNC1=C2N=CNC2=NC=N1 LLGCZKLHOPOIBI-UHFFFAOYSA-N 0.000 claims 1
- DWSKLBXLASTSJQ-UHFFFAOYSA-N N-[(1-pyridin-2-ylindolizin-2-yl)methyl]-7H-purin-6-amine Chemical compound N1=C(C=CC=C1)C=1C(=CN2C=CC=CC=12)CNC1=C2N=CNC2=NC=N1 DWSKLBXLASTSJQ-UHFFFAOYSA-N 0.000 claims 1
- RQHWBMBAIWGPHI-UHFFFAOYSA-N N-[(3-phenylindolizin-2-yl)methyl]-7H-purin-6-amine Chemical compound C1(=CC=CC=C1)C1=C(C=C2C=CC=CN12)CNC1=C2N=CNC2=NC=N1 RQHWBMBAIWGPHI-UHFFFAOYSA-N 0.000 claims 1
- QUCZTXWWMCDXBA-UHFFFAOYSA-N N-[(3-pyridin-2-ylindolizin-2-yl)methyl]-7H-purin-6-amine Chemical compound N1=C(C=CC=C1)C1=C(C=C2C=CC=CN12)CNC1=C2N=CNC2=NC=N1 QUCZTXWWMCDXBA-UHFFFAOYSA-N 0.000 claims 1
- WZQWXUKOVXUYSY-UHFFFAOYSA-N N-[3-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]-5-fluorophenyl]methanesulfonamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=C(C=1)F)NS(=O)(=O)C)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 WZQWXUKOVXUYSY-UHFFFAOYSA-N 0.000 claims 1
- AEELJRJXZMBYMH-UHFFFAOYSA-N N-[3-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]acetamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=CC=1)NC(C)=O)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 AEELJRJXZMBYMH-UHFFFAOYSA-N 0.000 claims 1
- IGRDPHYBUUISBP-UHFFFAOYSA-N N-[3-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methanesulfonamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=CC=1)NS(=O)(=O)C)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 IGRDPHYBUUISBP-UHFFFAOYSA-N 0.000 claims 1
- GRJSWFOIPLBNNY-UHFFFAOYSA-N N-[[1-(2-methylphenyl)indolizin-2-yl]methyl]-7H-purin-6-amine Chemical compound CC1=C(C=CC=C1)C=1C(=CN2C=CC=CC=12)CNC1=C2N=CNC2=NC=N1 GRJSWFOIPLBNNY-UHFFFAOYSA-N 0.000 claims 1
- ISRDTYFNLDZHLQ-UHFFFAOYSA-N N-[[1-(3-fluorophenyl)indolizin-2-yl]methyl]-7H-purin-6-amine Chemical compound FC=1C=C(C=CC=1)C=1C(=CN2C=CC=CC=12)CNC1=C2N=CNC2=NC=N1 ISRDTYFNLDZHLQ-UHFFFAOYSA-N 0.000 claims 1
- ZBPSFHHAFLIJKN-UHFFFAOYSA-N N-[[3-(2-fluorophenyl)indolizin-2-yl]methyl]-7H-purin-6-amine Chemical compound FC1=C(C=CC=C1)C1=C(C=C2C=CC=CN12)CNC1=C2N=CNC2=NC=N1 ZBPSFHHAFLIJKN-UHFFFAOYSA-N 0.000 claims 1
- KBUAOMIEDOBXAW-UHFFFAOYSA-N N-[[3-(3-fluorophenyl)indolizin-2-yl]methyl]-7H-purin-6-amine Chemical compound FC=1C=C(C=CC=1)C1=C(C=C2C=CC=CN12)CNC1=C2N=CNC2=NC=N1 KBUAOMIEDOBXAW-UHFFFAOYSA-N 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 201000005702 Pertussis Diseases 0.000 claims 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims 1
- 206010057190 Respiratory tract infections Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 206010069363 Traumatic lung injury Diseases 0.000 claims 1
- 206010070488 Upper-airway cough syndrome Diseases 0.000 claims 1
- QAJZWOGIWSZORI-UHFFFAOYSA-N [3-[4-amino-1-[1-(3-pyridin-2-ylindolizin-2-yl)ethyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methanol Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1C=C(C=CC=1)CO)C(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 QAJZWOGIWSZORI-UHFFFAOYSA-N 0.000 claims 1
- NKPQYJNITRXHFA-UHFFFAOYSA-N [4-amino-6-[1-(3-pyridin-2-ylindolizin-2-yl)ethylamino]pyrimidin-5-yl]methanol Chemical compound NC1=NC=NC(=C1CO)NC(C)C=1C=C2C=CC=CN2C=1C1=NC=CC=C1 NKPQYJNITRXHFA-UHFFFAOYSA-N 0.000 claims 1
- LCAKUCNRZOHKIK-UHFFFAOYSA-N [6-[2-[1-[4-amino-3-(3-fluoro-5-hydroxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]indolizin-3-yl]pyridin-3-yl]-morpholin-4-ylmethanone 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)C(=O)N1CCOCC1 LCAKUCNRZOHKIK-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 125000005014 aminoalkynyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 206010007604 cardiac sarcoidosis Diseases 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 208000013116 chronic cough Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000005713 exacerbation Effects 0.000 claims 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 230000002440 hepatic effect Effects 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 231100000515 lung injury Toxicity 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 230000035772 mutation Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 230000019100 sperm motility Effects 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 210000000115 thoracic cavity Anatomy 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 206010044652 trigeminal neuralgia Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14172764 | 2014-06-17 | ||
| EP14172764.4 | 2014-06-17 | ||
| PCT/EP2015/063390 WO2015193263A1 (en) | 2014-06-17 | 2015-06-16 | Indolizine derivatives as phoshoinositide 3-kinases inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017518326A JP2017518326A (ja) | 2017-07-06 |
| JP2017518326A5 true JP2017518326A5 (show.php) | 2018-07-19 |
| JP6730200B2 JP6730200B2 (ja) | 2020-07-29 |
Family
ID=50942205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016573030A Expired - Fee Related JP6730200B2 (ja) | 2014-06-17 | 2015-06-16 | ホスホイノシチド３−キナーゼ阻害剤としてのインドリジン誘導体 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US9527869B2 (show.php) |
| EP (1) | EP3157920B1 (show.php) |
| JP (1) | JP6730200B2 (show.php) |
| KR (1) | KR102420322B1 (show.php) |
| CN (1) | CN106661019B (show.php) |
| AR (1) | AR100879A1 (show.php) |
| AU (1) | AU2015276264B2 (show.php) |
| BR (1) | BR112016028845B1 (show.php) |
| CA (1) | CA2952287C (show.php) |
| CL (1) | CL2016003214A1 (show.php) |
| EA (1) | EA031409B1 (show.php) |
| ES (1) | ES2750791T3 (show.php) |
| GE (2) | GEAP201814349A (show.php) |
| IL (1) | IL249554A0 (show.php) |
| MX (1) | MX373129B (show.php) |
| PE (1) | PE20170303A1 (show.php) |
| PH (1) | PH12016502291A1 (show.php) |
| PL (1) | PL3157920T3 (show.php) |
| SG (1) | SG11201610473QA (show.php) |
| TN (1) | TN2016000555A1 (show.php) |
| TW (1) | TW201625611A (show.php) |
| WO (1) | WO2015193263A1 (show.php) |
| ZA (1) | ZA201608637B (show.php) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014237340C1 (en) | 2013-03-15 | 2018-11-08 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| EA202092627A1 (ru) | 2013-11-18 | 2021-09-30 | 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 |
| CA3011465A1 (en) * | 2016-01-15 | 2017-07-20 | The Brigham And Women's Hospital, Inc. | Pyridazine derivatives as eaat2 activators |
| EP3411375B1 (en) | 2016-02-04 | 2020-08-05 | Chiesi Farmaceutici S.p.A. | Pyrazole derivatives as phosphoinositide 3-kinases inhibitors |
| UA125592C2 (uk) | 2017-03-16 | 2022-04-27 | Джянгсу Хенгруй Медісін Ко., Лтд. | ПОХІДНА ГЕТЕРОАРИЛ[4,3-c]ПІРИМІДИН-5-АМІНУ, СПОСІБ ЇЇ ОТРИМАННЯ ТА ЇЇ МЕДИЧНІ ЗАСТОСУВАННЯ |
| 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 |
| WO2019236625A1 (en) | 2018-06-04 | 2019-12-12 | Ohio State Innovation Foundation | Eaat2 activators and methods of using thereof |
| CA3135309A1 (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 |
| US20230102520A1 (en) * | 2019-07-03 | 2023-03-30 | 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 |
| WO2023057394A1 (en) | 2021-10-04 | 2023-04-13 | 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY28931A1 (es) * | 2004-06-03 | 2005-12-30 | Bayer Pharmaceuticals Corp | Derivados de pirrolotriazina utiles para tratar trastornos hiper-proliferativos y enfermedades asociadas con angiogenesis |
| US8063071B2 (en) | 2007-10-31 | 2011-11-22 | GlaxoSmithKline, LLC | Chemical compounds |
| EP2331541B1 (en) * | 2008-09-04 | 2015-04-22 | Boehringer Ingelheim International GmbH | Indolizine inhibitors of leukotriene production |
| 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 |
| CN103002738A (zh) | 2010-05-21 | 2013-03-27 | 英特利凯恩有限责任公司 | 用于激酶调节的化学化合物、组合物和方法 |
| 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 |
-
2015
- 2015-06-16 TN TN2016000555A patent/TN2016000555A1/en unknown
- 2015-06-16 GE GEAP201814349A patent/GEAP201814349A/en unknown
- 2015-06-16 CA CA2952287A patent/CA2952287C/en active Active
- 2015-06-16 EP EP15735639.5A patent/EP3157920B1/en active Active
- 2015-06-16 WO PCT/EP2015/063390 patent/WO2015193263A1/en not_active Ceased
- 2015-06-16 TW TW104119395A patent/TW201625611A/zh unknown
- 2015-06-16 BR BR112016028845-9A patent/BR112016028845B1/pt not_active IP Right Cessation
- 2015-06-16 PE PE2016002720A patent/PE20170303A1/es unknown
- 2015-06-16 CN CN201580032341.XA patent/CN106661019B/zh not_active Expired - Fee Related
- 2015-06-16 GE GEAP201514349A patent/GEP20186938B/en unknown
- 2015-06-16 JP JP2016573030A patent/JP6730200B2/ja not_active Expired - Fee Related
- 2015-06-16 AR ARP150101923A patent/AR100879A1/es unknown
- 2015-06-16 ES ES15735639T patent/ES2750791T3/es active Active
- 2015-06-16 AU AU2015276264A patent/AU2015276264B2/en not_active Ceased
- 2015-06-16 KR KR1020177000424A patent/KR102420322B1/ko active Active
- 2015-06-16 MX MX2016016583A patent/MX373129B/es active IP Right Grant
- 2015-06-16 SG SG11201610473QA patent/SG11201610473QA/en unknown
- 2015-06-16 PL PL15735639T patent/PL3157920T3/pl unknown
- 2015-06-16 EA EA201692313A patent/EA031409B1/ru not_active IP Right Cessation
- 2015-06-17 US US14/741,965 patent/US9527869B2/en not_active Expired - Fee Related
-
2016
- 2016-11-17 PH PH12016502291A patent/PH12016502291A1/en unknown
- 2016-12-14 CL CL2016003214A patent/CL2016003214A1/es unknown
- 2016-12-14 ZA ZA2016/08637A patent/ZA201608637B/en unknown
- 2016-12-14 IL IL249554A patent/IL249554A0/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017518326A5 (show.php) | ||
| AU2010249380B2 (en) | N-(hetero)aryl-pyrrolidine derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines and pyrrol-3-yl-pyrrolo[2,3-d]pyrimidines as Janus kinase inhibitors | |
| US8962596B2 (en) | 5,7-substituted-imidazo[1,2-C]pyrimidines as inhibitors of JAK kinases | |
| RU2473549C2 (ru) | Пиримидиновые соединения, композиции и способы применения | |
| AU2015276264B2 (en) | Indolizine derivatives as phosphoinositide 3-kinases inhibitors | |
| HRP20240935T1 (hr) | Heterociklični i heteroaril spojevi za liječenje huntingtonove bolesti | |
| AU2019216728A1 (en) | Heteroaryl pyridone and aza-pyridone compounds as inhibitors of Btk activity | |
| TW202423440A (zh) | Ｋｒａｓ ｇ１２ｃ突變蛋白的系鏈之雜環抑制劑及其用途 | |
| JPWO2020005873A5 (show.php) | ||
| JP2019535664A5 (show.php) | ||
| CA2687035A1 (en) | Amino-heterocyclic compounds | |
| JP2013523884A5 (show.php) | ||
| JP2015533822A5 (show.php) | ||
| AU2011343477A1 (en) | Bicyclic triazole and pyrazole lactams as allosteric modulators of mGluR5 receptors | |
| AU2021370660A1 (en) | Heterocyclic spiro compounds and methods of use | |
| HRP20192151T1 (hr) | Derivati izokromena kao inhibitori fosfoinozitid 3-kinaza | |
| RU2020127848A (ru) | Производные 4-гидроксипиперидина и их применение в качестве ингибиторов убиквитин-специфической протеазы 19 (usp19) | |
| JP2013518823A5 (show.php) | ||
| TW202412783A (zh) | 酪胺酸激酶２抑制劑及其用途 | |
| WO2025230878A1 (en) | Macrocyclic compounds as modulators of kras and uses thereof | |
| WO2025230862A1 (en) | Macrocyclic amino compounds as modulators of kras and uses therof | |
| NZ771414A (en) | Heterocyclic and heteroaryl compounds for treating huntington's disease | |
| AU2015201991A1 (en) | 5, 7-substituted-imidazo [1, 2-c] pyrimidines as inhibitors of JAK kinases |