JP2019505595A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims 1
- 0 **C1=NC=C*1 Chemical compound **C1=NC=C*1 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
- HROOMWGGFGWBOX-OZMOBFKHSA-N CC(C)[C@@H](C)/C=C\CC(c1cc(N(C)C)ccc1)N Chemical compound CC(C)[C@@H](C)/C=C\CC(c1cc(N(C)C)ccc1)N HROOMWGGFGWBOX-OZMOBFKHSA-N 0.000 description 1
- QADGOIBIXXQEJL-UHFFFAOYSA-N Cc1cc(C(CCC2)N2I)n[n]1C Chemical compound Cc1cc(C(CCC2)N2I)n[n]1C QADGOIBIXXQEJL-UHFFFAOYSA-N 0.000 description 1
- CCPLZTQBOPSOEU-UHFFFAOYSA-N NN(CCC1)C1c1cccc(Cl)c1 Chemical compound NN(CCC1)C1c1cccc(Cl)c1 CCPLZTQBOPSOEU-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16156533 | 2016-02-19 | ||
| EP16156533.8 | 2016-02-19 | ||
| PCT/EP2017/053614 WO2017140843A1 (en) | 2016-02-19 | 2017-02-17 | 6-heterocyclyl-4-morpholin-4-ylpyridine-2-one compounds useful for the treatment of cancer and diabetes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019505595A JP2019505595A (ja) | 2019-02-28 |
| JP2019505595A5 true JP2019505595A5 (enExample) | 2020-03-26 |
| JP6858984B2 JP6858984B2 (ja) | 2021-04-14 |
Family
ID=55404646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018562702A Active JP6858984B2 (ja) | 2016-02-19 | 2017-02-17 | がんおよび糖尿病の治療に有用な６−ヘテロシクリル−４−モルホリン−４−イルピリジン−２−オン化合物 |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US11179399B2 (enExample) |
| EP (1) | EP3416957B1 (enExample) |
| JP (1) | JP6858984B2 (enExample) |
| CN (1) | CN108884067B (enExample) |
| AU (1) | AU2017219847B2 (enExample) |
| CY (1) | CY1123349T1 (enExample) |
| DK (1) | DK3416957T3 (enExample) |
| ES (1) | ES2821400T3 (enExample) |
| HR (1) | HRP20201430T1 (enExample) |
| HU (1) | HUE051059T2 (enExample) |
| LT (1) | LT3416957T (enExample) |
| PL (1) | PL3416957T3 (enExample) |
| PT (1) | PT3416957T (enExample) |
| RS (1) | RS60900B1 (enExample) |
| RU (1) | RU2762968C2 (enExample) |
| SI (1) | SI3416957T1 (enExample) |
| SM (1) | SMT202000529T1 (enExample) |
| TW (1) | TWI723131B (enExample) |
| WO (1) | WO2017140843A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT3416957T (lt) * | 2016-02-19 | 2020-11-25 | Sprint Bioscience Ab | 6-heterociklil-4-morfolin-4-ilpiridin-2-ono junginiai, tinkami vėžio ir diabeto gydymui |
| CN116589461A (zh) | 2017-08-23 | 2023-08-15 | 思普瑞特生物科学公司 | 氮杂吲哚基吡啶酮化合物和二氮杂吲哚基吡啶酮化合物 |
| EP4056556A1 (en) | 2017-08-23 | 2022-09-14 | Sprint Bioscience AB | Pyridylpyridone compounds |
| IL302293A (en) | 2017-08-23 | 2023-06-01 | Sprint Bioscience Ab | Pyridinamine-pyridone and pyrimidinamine-pyridone compounds |
| IL302077A (en) | 2017-08-23 | 2023-06-01 | Sprint Bioscience Ab | Morpholinylpyridone compounds |
| AU2019251363B2 (en) * | 2018-04-10 | 2024-03-07 | Neuropore Therapies, Inc. | Morpholine derivates as inhibitors of Vps34 |
| 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 |
| WO2020008046A1 (en) | 2018-07-06 | 2020-01-09 | Sprint Bioscience Ab | Biomarker |
| ES3023544T3 (en) * | 2019-12-04 | 2025-06-02 | Chdi Foundation Inc | Atm kinase inhibitors and compositions and methods of use thereof |
| JP2023550638A (ja) * | 2020-11-25 | 2023-12-04 | デシフェラ・ファーマシューティカルズ，エルエルシー | ウイルス感染症の処置に使用するための、ｖｓｐ３４阻害剤としてのモルホリノ誘導体 |
| 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 |
| JP2023550641A (ja) * | 2020-11-25 | 2023-12-04 | デシフェラ・ファーマシューティカルズ，エルエルシー | ウイルス感染症の治療に使用するためのｖｓｐ３４阻害剤としてのモルホリノ誘導体 |
| JP2024532780A (ja) | 2021-08-13 | 2024-09-10 | デシフェラ・ファーマシューティカルズ，エルエルシー | Ｖｐｓ３４阻害剤を使用した併用療法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2412273T3 (es) | 2002-11-21 | 2013-07-10 | Novartis Ag | Inhibidores de 2-morfolín-4-pirimidinas como inhibidores de fosfotidilinositol (PI) 3-quinasa y su uso en el tratamiento del cáncer. |
| GB2465405A (en) | 2008-11-10 | 2010-05-19 | Univ Basel | Triazine, pyrimidine and pyridine analogues and their use in therapy |
| ES2487623T3 (es) | 2009-07-02 | 2014-08-22 | Sanofi | Derivados de 6,7,8,9-tetrahidro-pirimido{1,2-a}pirimidin-4-ona, su preparación y su aplicación farmacéutica |
| WO2012085815A1 (en) | 2010-12-21 | 2012-06-28 | Novartis Ag | Bi-heteroaryl compounds as vps34 inhibitors |
| HUE024504T2 (en) | 2010-12-23 | 2016-01-28 | Sanofi Sa | Pyrimidine derivatives, a process for their preparation and their use in medicine |
| 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 |
| TN2016000270A1 (en) | 2014-01-14 | 2017-10-06 | Millennium Pharm Inc | Heteroaryls and uses thereof. |
| EP3094326A4 (en) | 2014-01-14 | 2017-07-26 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| MA39823A (fr) | 2014-04-03 | 2018-01-09 | Janssen Pharmaceutica Nv | Dérivés de pyridine macrocyclique |
| MA39822A (fr) | 2014-04-03 | 2018-02-06 | Janssen Pharmaceutica Nv | Dérivés de pyrimidine bicycle |
| BR112017004704A2 (pt) | 2014-09-17 | 2018-01-23 | Verseon Corp | composto, composição farmacêutica, e, método para tratar uma doença ou distúrbio em um indivíduo |
| LT3416957T (lt) * | 2016-02-19 | 2020-11-25 | Sprint Bioscience Ab | 6-heterociklil-4-morfolin-4-ilpiridin-2-ono junginiai, tinkami vėžio ir diabeto gydymui |
| 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 |
-
2017
- 2017-02-17 LT LTEP17704791.7T patent/LT3416957T/lt unknown
- 2017-02-17 RU RU2018131766A patent/RU2762968C2/ru active
- 2017-02-17 ES ES17704791T patent/ES2821400T3/es active Active
- 2017-02-17 AU AU2017219847A patent/AU2017219847B2/en active Active
- 2017-02-17 SM SM20200529T patent/SMT202000529T1/it unknown
- 2017-02-17 EP EP17704791.7A patent/EP3416957B1/en active Active
- 2017-02-17 DK DK17704791.7T patent/DK3416957T3/da active
- 2017-02-17 CN CN201780015103.7A patent/CN108884067B/zh active Active
- 2017-02-17 WO PCT/EP2017/053614 patent/WO2017140843A1/en not_active Ceased
- 2017-02-17 RS RS20201061A patent/RS60900B1/sr unknown
- 2017-02-17 PL PL17704791T patent/PL3416957T3/pl unknown
- 2017-02-17 SI SI201730405T patent/SI3416957T1/sl unknown
- 2017-02-17 PT PT177047917T patent/PT3416957T/pt unknown
- 2017-02-17 HU HUE17704791A patent/HUE051059T2/hu unknown
- 2017-02-17 US US15/999,432 patent/US11179399B2/en active Active
- 2017-02-17 TW TW106105178A patent/TWI723131B/zh not_active IP Right Cessation
- 2017-02-17 HR HRP20201430TT patent/HRP20201430T1/hr unknown
- 2017-02-17 JP JP2018562702A patent/JP6858984B2/ja active Active
-
2020
- 2020-09-15 CY CY20201100870T patent/CY1123349T1/el unknown
-
2021
- 2021-10-14 US US17/501,407 patent/US11963963B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019505595A5 (enExample) | ||
| RU2018131766A (ru) | 6-гетероциклил-4-морфолин-4-илпиридин-2-оны, пригодные для лечения рака и диабета | |
| KR101985984B1 (ko) | 키나아제 저해제로서의 벤조니트릴 유도체 | |
| JP6162144B2 (ja) | ４，４−二置換−１，４−ジヒドロピリミジン、及びｂ型肝炎の処置のための医薬としてのその使用 | |
| JP6013375B2 (ja) | キナーゼ阻害剤としてのチアゾリルフェニル−ベンゼンスルホンアミド誘導体 | |
| AU2014233414B2 (en) | N-acyl-N'-(pyridin-2-yl) ureas and analogs exhibiting anti-cancer and anti-proliferative activities | |
| JP4638355B2 (ja) | チアゾール誘導体 | |
| CN1960731B (zh) | 调节炎性和转移过程的方法 | |
| RU2451674C2 (ru) | Пиридинкарбоксамиды в качестве ингибиторов 11-бета-hsd1 | |
| CA2529686C (en) | 2-acylaminothiazole derivative or salt thereof | |
| JP2019527731A (ja) | Ｈｂｖ感染の治療のための新規治療薬 | |
| JP2017530999A5 (enExample) | ||
| JP2012501312A5 (enExample) | ||
| JP5852678B2 (ja) | 抗腫瘍剤の効果増強剤 | |
| JP2019505594A5 (enExample) | ||
| JP2009529047A5 (enExample) | ||
| JP2010508338A5 (enExample) | ||
| RU2017121044A (ru) | Производные амидотиадиазола в качестве ингибиторов надфн-оксидазы | |
| RU2018131775A (ru) | 6-арил-4-морфолин-1-илпиридоны, пригодные для лечения рака или диабета | |
| JP2017505794A5 (enExample) | ||
| RU2016102137A (ru) | Первичные карбоксамиды в качестве ингибиторов bik | |
| JP2009513575A5 (enExample) | ||
| HUE033177T2 (en) | Pyrazine carboxamide compound | |
| WO2011142316A1 (ja) | キヌレニン産生抑制作用を有する含窒素複素環化合物 | |
| JP2017537948A5 (enExample) |