JP2019505595A5 - - Google Patents
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- JP2019505595A5 JP2019505595A5 JP2018562702A JP2018562702A JP2019505595A5 JP 2019505595 A5 JP2019505595 A5 JP 2019505595A5 JP 2018562702 A JP2018562702 A JP 2018562702A JP 2018562702 A JP2018562702 A JP 2018562702A JP 2019505595 A5 JP2019505595 A5 JP 2019505595A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- methylmorpholin
- compound according
- pyrrolidin
- phenyl
- 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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- 150000001875 compounds Chemical class 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 208000036142 Viral infection Diseases 0.000 claims description 5
- 230000009385 viral infection Effects 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- -1 1-azetidinyl Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 208000022679 triple-negative breast carcinoma Diseases 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- IKRSDSVEUUDANC-TZMCWYRMSA-N 1-methyl-4-[(3R)-3-methylmorpholin-4-yl]-6-[(2R)-2-(trifluoromethyl)piperidin-1-yl]pyridin-2-one Chemical compound CN1C(C=C(C=C1N1[C@H](CCCC1)C(F)(F)F)N1[C@@H](COCC1)C)=O IKRSDSVEUUDANC-TZMCWYRMSA-N 0.000 claims 1
- GEPVAUNVJFZVOF-UHFFFAOYSA-N 1-methyl-4-morpholin-4-yl-6-(2-phenylpyrrolidin-1-yl)pyridin-2-one Chemical compound CN1C(C=C(C=C1N1C(CCC1)C1=CC=CC=C1)N1CCOCC1)=O GEPVAUNVJFZVOF-UHFFFAOYSA-N 0.000 claims 1
- DNHWJOKDRSZNOZ-UHFFFAOYSA-N 4-(3-methylmorpholin-4-yl)-6-(2-phenylpyrrolidin-1-yl)-1H-pyridin-2-one Chemical compound CC1N(CCOC1)C1=CC(NC(=C1)N1C(CCC1)C1=CC=CC=C1)=O DNHWJOKDRSZNOZ-UHFFFAOYSA-N 0.000 claims 1
- GEYOWPVRKFMLPA-UHFFFAOYSA-N 4-(3-methylmorpholin-4-yl)-6-(2-pyridin-3-ylpyrrolidin-1-yl)-1H-pyridin-2-one Chemical compound CC1N(CCOC1)C1=CC(NC(=C1)N1C(CCC1)C=1C=NC=CC=1)=O GEYOWPVRKFMLPA-UHFFFAOYSA-N 0.000 claims 1
- PTBANPMTCAZHMW-UHFFFAOYSA-N 4-(3-methylmorpholin-4-yl)-6-(oxan-4-yl)-1H-pyridin-2-one Chemical compound CC1N(CCOC1)C1=CC(NC(=C1)C1CCOCC1)=O PTBANPMTCAZHMW-UHFFFAOYSA-N 0.000 claims 1
- DNHWJOKDRSZNOZ-NNJIEVJOSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-(2-phenylpyrrolidin-1-yl)-1H-pyridin-2-one Chemical compound C[C@H]1N(CCOC1)C1=CC(NC(=C1)N1C(CCC1)C1=CC=CC=C1)=O DNHWJOKDRSZNOZ-NNJIEVJOSA-N 0.000 claims 1
- PVTKINADSZXHMB-XPCCGILXSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-(2-pyridin-2-ylpyrrolidin-1-yl)-1H-pyridin-2-one Chemical compound C[C@@H]1COCCN1c1cc([nH]c(=O)c1)N1CCCC1c1ccccn1 PVTKINADSZXHMB-XPCCGILXSA-N 0.000 claims 1
- DTQNLEMAQOJYJU-JHJMLUEUSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-(3-methylmorpholin-4-yl)-1H-pyridin-2-one Chemical compound C[C@H]1N(CCOC1)C1=CC(NC(=C1)N1C(COCC1)C)=O DTQNLEMAQOJYJU-JHJMLUEUSA-N 0.000 claims 1
- DBAKZEXBDFLYJS-NNJIEVJOSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-(3-phenylmorpholin-4-yl)-1H-pyridin-2-one Chemical compound C[C@H]1N(CCOC1)C1=CC(NC(=C1)N1C(COCC1)C1=CC=CC=C1)=O DBAKZEXBDFLYJS-NNJIEVJOSA-N 0.000 claims 1
- CQGZGSXVKTYYNB-VTBWFHPJSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-(4-methyl-2-phenylpiperazin-1-yl)-1H-pyridin-2-one Chemical compound C[C@H]1N(CCOC1)C1=CC(NC(=C1)N1C(CN(CC1)C)C1=CC=CC=C1)=O CQGZGSXVKTYYNB-VTBWFHPJSA-N 0.000 claims 1
- ZCJJZKBILRFGMJ-CYBMUJFWSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-(8-oxa-5-azaspiro[3.5]nonan-5-yl)-1H-pyridin-2-one Chemical compound C[C@H]1N(CCOC1)C1=CC(NC(=C1)N1C2(CCC2)COCC1)=O ZCJJZKBILRFGMJ-CYBMUJFWSA-N 0.000 claims 1
- MKNQUJFOKNHRDF-ZYHUDNBSSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[(2R)-2-(trifluoromethyl)pyrrolidin-1-yl]-1H-pyridin-2-one Chemical compound C[C@@H]1COCCN1c1cc([nH]c(=O)c1)N1CCC[C@@H]1C(F)(F)F MKNQUJFOKNHRDF-ZYHUDNBSSA-N 0.000 claims 1
- BNZSFCIZMOKBJZ-VQIMIIECSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[(2R)-2-phenylpiperidin-1-yl]-1H-pyridin-2-one Chemical compound C[C@H]1N(CCOC1)C1=CC(NC(=C1)N1[C@H](CCCC1)C1=CC=CC=C1)=O BNZSFCIZMOKBJZ-VQIMIIECSA-N 0.000 claims 1
- MKNQUJFOKNHRDF-PWSUYJOCSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[(2S)-2-(trifluoromethyl)pyrrolidin-1-yl]-1H-pyridin-2-one Chemical compound C[C@@H]1COCCN1c1cc([nH]c(=O)c1)N1CCC[C@H]1C(F)(F)F MKNQUJFOKNHRDF-PWSUYJOCSA-N 0.000 claims 1
- HYEKDPGQMZZYGZ-PUODRLBUSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[2-(1,3-thiazol-2-yl)pyrrolidin-1-yl]-1H-pyridin-2-one Chemical compound C[C@H]1N(CCOC1)C1=CC(NC(=C1)N1C(CCC1)C=1SC=CN=1)=O HYEKDPGQMZZYGZ-PUODRLBUSA-N 0.000 claims 1
- PUWKHNNESZZNEQ-JBZHPUCOSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[2-(1-methylpyrazol-4-yl)pyrrolidin-1-yl]-1H-pyridin-2-one Chemical compound C[C@H]1N(CCOC1)C1=CC(NC(=C1)N1C(CCC1)C=1C=NN(C=1)C)=O PUWKHNNESZZNEQ-JBZHPUCOSA-N 0.000 claims 1
- HNJWOJXQTQJHCS-ZGTOLYCTSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[2-(5-methyl-1,2-oxazol-3-yl)pyrrolidin-1-yl]-1H-pyridin-2-one Chemical compound CC1=CC(=NO1)C1N(CCC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C HNJWOJXQTQJHCS-ZGTOLYCTSA-N 0.000 claims 1
- IARAUFAUVKBTEM-JTDNENJMSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[2-(trifluoromethyl)piperidin-1-yl]-1H-pyridin-2-one Chemical compound C[C@@H]1COCCN1c1cc([nH]c(=O)c1)N1CCCCC1C(F)(F)F IARAUFAUVKBTEM-JTDNENJMSA-N 0.000 claims 1
- XOMBIBRABUIJDB-IKJXHCRLSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[2-[3-(trifluoromethoxy)phenyl]pyrrolidin-1-yl]-1H-pyridin-2-one Chemical compound C[C@H]1N(CCOC1)C1=CC(NC(=C1)N1C(CCC1)C1=CC(=CC=C1)OC(F)(F)F)=O XOMBIBRABUIJDB-IKJXHCRLSA-N 0.000 claims 1
- LPPNQVSUXZTYEJ-IKJXHCRLSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[2-[3-(trifluoromethyl)phenyl]pyrrolidin-1-yl]-1H-pyridin-2-one Chemical compound C[C@H]1N(CCOC1)C1=CC(NC(=C1)N1C(CCC1)C1=CC(=CC=C1)C(F)(F)F)=O LPPNQVSUXZTYEJ-IKJXHCRLSA-N 0.000 claims 1
- HMQUAFQWSSAWFO-RWANSRKNSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[3-(trifluoromethyl)morpholin-4-yl]-1H-pyridin-2-one Chemical compound C[C@@H]1COCCN1c1cc([nH]c(=O)c1)N1CCOCC1C(F)(F)F HMQUAFQWSSAWFO-RWANSRKNSA-N 0.000 claims 1
- PJLOZUMADBELJZ-IUDNXUCKSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[4-(oxolane-2-carbonyl)-2-(trifluoromethyl)piperazin-1-yl]-1H-pyridin-2-one Chemical compound C[C@@H]1COCCN1c1cc([nH]c(=O)c1)N1CCN(CC1C(F)(F)F)C(=O)C1CCCO1 PJLOZUMADBELJZ-IUDNXUCKSA-N 0.000 claims 1
- DGSKQMNTQWRXAO-JTDNENJMSA-N 4-[(3R)-3-methylmorpholin-4-yl]-6-[4-methyl-2-(trifluoromethyl)piperazin-1-yl]-1H-pyridin-2-one Chemical compound C[C@H]1N(CCOC1)C1=CC(NC(=C1)N1C(CN(CC1)C)C(F)(F)F)=O DGSKQMNTQWRXAO-JTDNENJMSA-N 0.000 claims 1
- ARBITBIHOFPTEL-UHFFFAOYSA-N 4-morpholin-4-yl-6-(2-phenylpyrrolidin-1-yl)-1H-pyridin-2-one Chemical compound O1CCN(CC1)C1=CC(NC(=C1)N1C(CCC1)C1=CC=CC=C1)=O ARBITBIHOFPTEL-UHFFFAOYSA-N 0.000 claims 1
- ARBITBIHOFPTEL-QGZVFWFLSA-N 4-morpholin-4-yl-6-[(2R)-2-phenylpyrrolidin-1-yl]-1H-pyridin-2-one Chemical compound O1CCN(CC1)C1=CC(NC(=C1)N1[C@H](CCC1)C1=CC=CC=C1)=O ARBITBIHOFPTEL-QGZVFWFLSA-N 0.000 claims 1
- ARBITBIHOFPTEL-KRWDZBQOSA-N 4-morpholin-4-yl-6-[(2S)-2-phenylpyrrolidin-1-yl]-1H-pyridin-2-one Chemical compound O1CCN(CC1)C1=CC(NC(=C1)N1[C@@H](CCC1)C1=CC=CC=C1)=O ARBITBIHOFPTEL-KRWDZBQOSA-N 0.000 claims 1
- BOHGTZPCBPVZJP-NNJIEVJOSA-N 6-(2-cyclohexylpyrrolidin-1-yl)-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound C1(CCCCC1)C1N(CCC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C BOHGTZPCBPVZJP-NNJIEVJOSA-N 0.000 claims 1
- OVFSASMMZLUCNU-UHFFFAOYSA-N 6-(3,6-dihydro-2H-pyran-4-yl)-4-(3-methylmorpholin-4-yl)-1H-pyridin-2-one Chemical compound O1CCC(=CC1)C1=CC(=CC(N1)=O)N1C(COCC1)C OVFSASMMZLUCNU-UHFFFAOYSA-N 0.000 claims 1
- ZATNXQFOVADOAQ-KEKZHRQWSA-N 6-(3-cyclopropylmorpholin-4-yl)-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound C1(CC1)C1N(CCOC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C ZATNXQFOVADOAQ-KEKZHRQWSA-N 0.000 claims 1
- HPLBRXRJVYSEKW-GFCCVEGCSA-N 6-(4-acetylpiperazin-1-yl)-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound C(C)(=O)N1CCN(CC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C HPLBRXRJVYSEKW-GFCCVEGCSA-N 0.000 claims 1
- JHNMTPGBZPUSKU-XPCCGILXSA-N 6-[2-(1,5-dimethylpyrazol-3-yl)pyrrolidin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound CN1N=C(C=C1C)C1N(CCC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C JHNMTPGBZPUSKU-XPCCGILXSA-N 0.000 claims 1
- XZJOKDHNHJPLGC-XPCCGILXSA-N 6-[2-(1-ethylpyrazol-3-yl)pyrrolidin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound C(C)N1N=C(C=C1)C1N(CCC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C XZJOKDHNHJPLGC-XPCCGILXSA-N 0.000 claims 1
- YCUJAYXTVJFLSC-YJJYDOSJSA-N 6-[2-(2,5-difluorophenyl)pyrrolidin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound FC1=C(C=C(C=C1)F)C1N(CCC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C YCUJAYXTVJFLSC-YJJYDOSJSA-N 0.000 claims 1
- PSAUUOVHPLDEPK-AFYYWNPRSA-N 6-[2-(2-methoxypropan-2-yl)pyrrolidin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound COC(C)(C)C1N(CCC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C PSAUUOVHPLDEPK-AFYYWNPRSA-N 0.000 claims 1
- DGGVYASTBIYPGX-IKJXHCRLSA-N 6-[2-(3-chlorophenyl)pyrrolidin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound ClC=1C=C(C=CC=1)C1N(CCC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C DGGVYASTBIYPGX-IKJXHCRLSA-N 0.000 claims 1
- ZZOLVSJDRQQXEZ-IKJXHCRLSA-N 6-[2-(3-fluorophenyl)pyrrolidin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound FC=1C=C(C=CC=1)C1N(CCC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C ZZOLVSJDRQQXEZ-IKJXHCRLSA-N 0.000 claims 1
- RJZKTHDWYBRNAN-QRIPLOBPSA-N 6-[2-(3-methoxyphenyl)piperidin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound COc1cccc(c1)C1CCCCN1c1cc(cc(=O)[nH]1)N1CCOC[C@H]1C RJZKTHDWYBRNAN-QRIPLOBPSA-N 0.000 claims 1
- FNSMSXAOAFPMGK-UHFFFAOYSA-N 6-[2-(3-methoxyphenyl)pyrrolidin-1-yl]-4-(3-methylmorpholin-4-yl)-1H-pyridin-2-one Chemical compound COC=1C=C(C=CC=1)C1N(CCC1)C1=CC(=CC(N1)=O)N1C(COCC1)C FNSMSXAOAFPMGK-UHFFFAOYSA-N 0.000 claims 1
- FNSMSXAOAFPMGK-NYRJJRHWSA-N 6-[2-(3-methoxyphenyl)pyrrolidin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound COC=1C=C(C=CC=1)C1N(CCC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C FNSMSXAOAFPMGK-NYRJJRHWSA-N 0.000 claims 1
- BOTFAMLEOGEUBK-JBZHPUCOSA-N 6-[2-(5-methylfuran-2-yl)pyrrolidin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound C[C@@H]1COCCN1c1cc([nH]c(=O)c1)N1CCCC1c1ccc(C)o1 BOTFAMLEOGEUBK-JBZHPUCOSA-N 0.000 claims 1
- WUPGYACORAXQIZ-QRIPLOBPSA-N 6-[2-[3-(dimethylamino)phenyl]pyrrolidin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound C[C@@H]1COCCN1c1cc([nH]c(=O)c1)N1CCCC1c1cccc(c1)N(C)C WUPGYACORAXQIZ-QRIPLOBPSA-N 0.000 claims 1
- AZNSSDSMKRAUCP-FWJOYPJLSA-N 6-[4-(5-fluoropyridine-3-carbonyl)-2-(trifluoromethyl)piperazin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound FC=1C=C(C=NC=1)C(=O)N1CC(N(CC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C)C(F)(F)F AZNSSDSMKRAUCP-FWJOYPJLSA-N 0.000 claims 1
- FIQAKPIBLSCANW-NYRJJRHWSA-N 6-[4-[2-(4-fluorophenyl)acetyl]-2-(trifluoromethyl)piperazin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound FC1=CC=C(C=C1)CC(=O)N1CC(N(CC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C)C(F)(F)F FIQAKPIBLSCANW-NYRJJRHWSA-N 0.000 claims 1
- XUVMGZJILCHMEP-YNODCEANSA-N 6-[4-acetyl-2-(trifluoromethyl)piperazin-1-yl]-4-[(3R)-3-methylmorpholin-4-yl]-1H-pyridin-2-one Chemical compound C(C)(=O)N1CC(N(CC1)C1=CC(=CC(N1)=O)N1[C@@H](COCC1)C)C(F)(F)F XUVMGZJILCHMEP-YNODCEANSA-N 0.000 claims 1
- 208000004672 Cardiovascular Infections Diseases 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- ISEVHXBSGDKMBU-PUODRLBUSA-N N,N-dimethyl-1-[4-[(3R)-3-methylmorpholin-4-yl]-6-oxo-1H-pyridin-2-yl]pyrrolidine-2-carboxamide Chemical compound CN(C(=O)C1N(CCC1)C=1NC(C=C(C=1)N1[C@@H](COCC1)C)=O)C ISEVHXBSGDKMBU-PUODRLBUSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 230000008512 biological response Effects 0.000 claims 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 239000003667 hormone antagonist Substances 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 239000003607 modifier Substances 0.000 claims 1
- 230000000626 neurodegenerative effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 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 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
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| DK3416957T3 (da) * | 2016-02-19 | 2020-09-21 | Sprint Bioscience Ab | 6-heterocyclyl-4-morpholin-4-ylpyridin-2-on-forbindelser anvendelige ved behandlingen af cancer og diabetes |
| US11560374B2 (en) * | 2017-08-23 | 2023-01-24 | Sprint Bioscience Ab | Morpholinylpyridone compounds |
| CN111094271B (zh) | 2017-08-23 | 2023-02-28 | 思普瑞特生物科学公司 | 吡啶胺-吡啶酮化合物和嘧啶胺-吡啶酮化合物 |
| JP7199738B2 (ja) | 2017-08-23 | 2023-01-06 | スプリント バイオサイエンス アクティエボラーグ | アザインドリルピリドンおよびジアザインドリルピリドン化合物 |
| WO2019038387A1 (en) | 2017-08-23 | 2019-02-28 | Sprint Bioscience Ab | PYRIDYLPYRIDONE COMPOUNDS |
| ES3032793T3 (en) | 2018-04-10 | 2025-07-24 | Neuropore Therapies Inc | Tri-substituted aryl and heteroaryl derivatives as modulators of pi3-kinase and autophagy pathways |
| CN112533917B (zh) * | 2018-04-10 | 2024-06-21 | 神经孔疗法股份有限公司 | 作为vps34的抑制剂的吗啉衍生物 |
| WO2020008046A1 (en) | 2018-07-06 | 2020-01-09 | Sprint Bioscience Ab | Biomarker |
| WO2021113506A1 (en) * | 2019-12-04 | 2021-06-10 | Chdi Foundation, Inc. | Atm kinase inhibitors and compositions and methods of use thereof |
| EP4251165A1 (en) * | 2020-11-25 | 2023-10-04 | Deciphera Pharmaceuticals, LLC | Morpholino derivatives as vsp34 inhibitors for use in the treatment of a viral infection |
| CA3199988A1 (en) | 2020-11-25 | 2022-06-02 | Daniel L. Flynn | Pyridylpyridone derivatives as vsp34 inhibitors for use in the treatment of a viral infection |
| WO2022115562A1 (en) * | 2020-11-25 | 2022-06-02 | Deciphera Pharmaceuticals, Llc | Morpholino derivatives as vsp34 inhibitors for use in the treatment of a viral infection |
| AU2022326573A1 (en) | 2021-08-13 | 2024-02-15 | Deciphera Pharmaceuticals, Llc | Combination therapy of vps34 inhibitors and sting agonist for use in the treatment of cancer |
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| US7423148B2 (en) | 2002-11-21 | 2008-09-09 | Chiron Corporation | Small molecule PI 3-kinase inhibitors and methods of their use |
| GB2465405A (en) | 2008-11-10 | 2010-05-19 | Univ Basel | Triazine, pyrimidine and pyridine analogues and their use in therapy |
| BRPI1015943A8 (pt) | 2009-07-02 | 2018-01-09 | Sanofi Sa | derivados de 1,2,3,4-tetra - hidro - pirimido {1,2-a} pirimidin-6-ona, o respectivo preparo e a respectiva utilização farmacêutica. |
| AU2011346567A1 (en) | 2010-12-21 | 2013-07-25 | Novartis Ag | Bi-heteroaryl compounds as Vps34 inhibitors |
| DK2655375T3 (en) | 2010-12-23 | 2015-03-09 | Sanofi Sa | PYRIMIDINON DERIVATIVES, PREPARATION AND PHARMACEUTICAL USE THEREOF |
| GB201120317D0 (en) | 2011-11-24 | 2012-01-04 | Queen Mary & Westfield College | Screening method |
| FR2992314B1 (fr) | 2012-06-22 | 2015-10-16 | Sanofi Sa | Nouveaux derives de 2,3-dihydro-1h-imidazo{1,2-a}pyrimidin-5-one et 1,2,3,4-tetrahydro-pyrimido{1,2-a}pyrimidin-6-one comportant une morpholine substituee, leur preparation et leur utilisation pharmaceutique |
| US9242969B2 (en) * | 2013-03-14 | 2016-01-26 | Novartis Ag | Biaryl amide compounds as kinase inhibitors |
| JP6074043B2 (ja) * | 2013-08-29 | 2017-02-01 | 富士フイルム株式会社 | 新規なモルホリン誘導体またはその塩 |
| AU2015206652A1 (en) | 2014-01-14 | 2016-08-04 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2015108881A1 (en) | 2014-01-14 | 2015-07-23 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| MA39822A (fr) | 2014-04-03 | 2018-02-06 | Janssen Pharmaceutica Nv | Dérivés de pyrimidine bicycle |
| MA39823A (fr) | 2014-04-03 | 2018-01-09 | Janssen Pharmaceutica Nv | Dérivés de pyridine macrocyclique |
| US10189810B2 (en) | 2014-09-17 | 2019-01-29 | Verseon Corporation | Pyrazolyl-substituted pyridone compounds as serine protease inhibitors |
| AU2017219846B2 (en) * | 2016-02-19 | 2021-05-13 | Sprint Bioscience Ab | 6-aryl-4-morpholin-1-ylpyridone compounds useful for the treatment of cancer and diabetes |
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