JPWO2019180646A5 - - Google Patents
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- Publication number
- JPWO2019180646A5 JPWO2019180646A5 JP2020550176A JP2020550176A JPWO2019180646A5 JP WO2019180646 A5 JPWO2019180646 A5 JP WO2019180646A5 JP 2020550176 A JP2020550176 A JP 2020550176A JP 2020550176 A JP2020550176 A JP 2020550176A JP WO2019180646 A5 JPWO2019180646 A5 JP WO2019180646A5
- Authority
- JP
- Japan
- Prior art keywords
- triazole
- dihydro
- aminomethyl
- methyl
- thiophene
- 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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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 127
- -1 thiazazole Chemical compound 0.000 claims 116
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 54
- 150000001875 compounds Chemical class 0.000 claims 36
- 150000003839 salts Chemical class 0.000 claims 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 30
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 28
- 125000004122 cyclic group Chemical group 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 229930192474 thiophene Natural products 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 10
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 9
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 7
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 6
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims 6
- CTOUNZIAEBIWAW-UHFFFAOYSA-N 3,4-dihydro-1h-quinazolin-2-one Chemical compound C1=CC=C2NC(=O)NCC2=C1 CTOUNZIAEBIWAW-UHFFFAOYSA-N 0.000 claims 6
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims 6
- QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 claims 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 6
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 claims 6
- 229920002554 vinyl polymer Polymers 0.000 claims 6
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 5
- IQPNCCUMIBKUMI-UHFFFAOYSA-N 2-methyl-4H-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cn1nc[nH]c1=O IQPNCCUMIBKUMI-UHFFFAOYSA-N 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- RGPBQGGBWIMGMA-BJMVGYQFSA-N 5-[(e)-[5-(4-bromophenyl)-6-hydroxy-3,6-dihydro-1,3,4-oxadiazin-2-ylidene]methyl]-1h-pyrimidine-2,4-dione Chemical compound OC1O\C(=C\C=2C(NC(=O)NC=2)=O)NN=C1C1=CC=C(Br)C=C1 RGPBQGGBWIMGMA-BJMVGYQFSA-N 0.000 claims 5
- 101710132836 Membrane primary amine oxidase Proteins 0.000 claims 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 5
- 102000056133 human AOC3 Human genes 0.000 claims 5
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 4
- SYZIUAAQNFJPJY-UHFFFAOYSA-N 1,4-dihydro-3,1-benzoxazin-2-one Chemical compound C1=CC=C2COC(=O)NC2=C1 SYZIUAAQNFJPJY-UHFFFAOYSA-N 0.000 claims 4
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims 4
- YWPMKTWUFVOFPL-UHFFFAOYSA-N 3,4-dihydro-2h-isoquinolin-1-one Chemical compound C1=CC=C2C(=O)NCCC2=C1 YWPMKTWUFVOFPL-UHFFFAOYSA-N 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims 4
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- XXBQLHATYQHJQC-UHFFFAOYSA-N 1,2-dihydroquinoxaline Chemical compound C1=CC=C2N=CCNC2=C1 XXBQLHATYQHJQC-UHFFFAOYSA-N 0.000 claims 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 3
- ORNSLMJWQDGQFF-UHFFFAOYSA-N 1h-pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C1=CC=C2NC(=O)COC2=N1 ORNSLMJWQDGQFF-UHFFFAOYSA-N 0.000 claims 3
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 3
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 3
- BIGWXAGEQONZGD-UHFFFAOYSA-N 2h-oxadiazol-5-one Chemical compound O=C1C=NNO1 BIGWXAGEQONZGD-UHFFFAOYSA-N 0.000 claims 3
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 claims 3
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 claims 3
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 3
- WFIHKLWVLPBMIQ-UHFFFAOYSA-N [1,3]thiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SC=NC2=C1 WFIHKLWVLPBMIQ-UHFFFAOYSA-N 0.000 claims 3
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000005145 cycloalkylaminosulfonyl group Chemical group 0.000 claims 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- OVLXOTUWFLHWQT-UHFFFAOYSA-N oxazolo[4,5-b]pyridin-2(3H)-one Chemical compound C1=CC=C2OC(=O)NC2=N1 OVLXOTUWFLHWQT-UHFFFAOYSA-N 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 3
- HAMAGKWXRRTWCJ-UHFFFAOYSA-N pyrido[2,3-b][1,4]oxazin-3-one Chemical compound C1=CN=C2OC(=O)C=NC2=C1 HAMAGKWXRRTWCJ-UHFFFAOYSA-N 0.000 claims 3
- MDBYWLYSYMTHNY-UHFFFAOYSA-N pyrido[2,3-d][1,3]oxazin-2-one Chemical compound O=c1nc2ncccc2co1 MDBYWLYSYMTHNY-UHFFFAOYSA-N 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- DFOURCCNIGVXNT-UHFFFAOYSA-N pyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CC=NC2=NC(=O)C=C21 DFOURCCNIGVXNT-UHFFFAOYSA-N 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- OVBSMCVFDKBNOZ-UHFFFAOYSA-N 1,4-oxazin-2-one;hydrochloride Chemical compound Cl.O=C1C=NC=CO1 OVBSMCVFDKBNOZ-UHFFFAOYSA-N 0.000 claims 2
- GTFMIJNXNMDHAB-UHFFFAOYSA-N 4h-1,4-benzothiazin-3-one Chemical compound C1=CC=C2NC(=O)CSC2=C1 GTFMIJNXNMDHAB-UHFFFAOYSA-N 0.000 claims 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 125000000033 alkoxyamino group Chemical group 0.000 claims 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
- JXHYCCGOZUGBFD-UHFFFAOYSA-N benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1 JXHYCCGOZUGBFD-UHFFFAOYSA-N 0.000 claims 2
- 230000001587 cholestatic effect Effects 0.000 claims 2
- 230000002440 hepatic effect Effects 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 230000003211 malignant effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- YBBBFMHGPCMHRZ-UHFFFAOYSA-N pyrido[2,3-b][1,4]oxazine Chemical compound C1=CC=C2[N]C=COC2=N1 YBBBFMHGPCMHRZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
- MQSLINQSJFALSP-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)pyrazole Chemical compound CN1C=CC(C(F)(F)F)=N1 MQSLINQSJFALSP-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- NRGKFNDKBDBBGY-UHFFFAOYSA-N 1h-pyridin-2-one;hydrochloride Chemical compound Cl.O=C1C=CC=CN1 NRGKFNDKBDBBGY-UHFFFAOYSA-N 0.000 claims 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- IJNRRDWXVLAQSD-UXBLZVDNSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(2-thiophen-2-ylethyl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)CCC=1SC=CC=1)=C\F IJNRRDWXVLAQSD-UXBLZVDNSA-N 0.000 claims 1
- VVVXXTRJVQHYQH-DCDCITSCSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[(5-bromothiophen-2-yl)methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound C1=C(SC(=C1)Br)CN2C=NN(C2=O)C/C(=C/F)/CN.Cl VVVXXTRJVQHYQH-DCDCITSCSA-N 0.000 claims 1
- IXMBLQQKTYERQH-VZUCSPMQSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[(5-pyridazin-4-ylthiophen-2-yl)methyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)CC=1SC(=CC=1)C1=CN=NC=C1)=C\F IXMBLQQKTYERQH-VZUCSPMQSA-N 0.000 claims 1
- GJOWGUSKXMGBDP-KPKJPENVSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[(5-pyridin-4-ylthiophen-2-yl)methyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)CC=1SC(=CC=1)C1=CC=NC=C1)=C\F GJOWGUSKXMGBDP-KPKJPENVSA-N 0.000 claims 1
- JTYXNWWQVCXSTP-MDWZMJQESA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[2-[5-(1,3-benzodioxol-5-yl)thiophen-2-yl]ethyl]-1,2,4-triazol-3-one Chemical compound NC\C(CN1N=CN(CCC2=CC=C(S2)C2=CC3=C(OCO3)C=C2)C1=O)=C/F JTYXNWWQVCXSTP-MDWZMJQESA-N 0.000 claims 1
- XQMFNFQTZSRXIP-NTUHNPAUSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[2-[5-(1-ethylpyrazol-4-yl)thiophen-2-yl]ethyl]-1,2,4-triazol-3-one Chemical compound CCN1C=C(C=N1)C1=CC=C(CCN2C=NN(C\C(CN)=C\F)C2=O)S1 XQMFNFQTZSRXIP-NTUHNPAUSA-N 0.000 claims 1
- USKKSBJWSQVRCM-KPKJPENVSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[2-[5-[6-(trifluoromethyl)pyridin-3-yl]thiophen-2-yl]ethyl]-1,2,4-triazol-3-one Chemical compound NC\C(CN1N=CN(CCC2=CC=C(S2)C2=CC=C(N=C2)C(F)(F)F)C1=O)=C/F USKKSBJWSQVRCM-KPKJPENVSA-N 0.000 claims 1
- NIWPXTJFXXWNMQ-KPKJPENVSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(1,2,3,6-tetrahydropyridin-4-yl)thiophen-2-yl]methyl]-1,2,4-triazol-3-one Chemical compound NC\C(CN1N=CN(CC2=CC=C(S2)C2=CCNCC2)C1=O)=C/F NIWPXTJFXXWNMQ-KPKJPENVSA-N 0.000 claims 1
- VIBMDHOBBSMNED-RIYZIHGNSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(1,3-benzodioxol-5-yl)-1-benzothiophen-2-yl]methyl]-1,2,4-triazol-3-one Chemical compound NC\C(CN1N=CN(CC2=CC3=CC(=CC=C3S2)C2=CC3=C(OCO3)C=C2)C1=O)=C/F VIBMDHOBBSMNED-RIYZIHGNSA-N 0.000 claims 1
- HAFZDZQKOCNVJG-XCVCLJGOSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(1H-pyrazol-4-yl)thiophen-2-yl]methyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)CC=1SC(=CC=1)C=1C=NNC=1)=C\F HAFZDZQKOCNVJG-XCVCLJGOSA-N 0.000 claims 1
- IMDXJKUXQWLVSV-XCVCLJGOSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(2-aminopyrimidin-5-yl)thiophen-2-yl]methyl]-1,2,4-triazol-3-one Chemical compound NC\C(CN1N=CN(CC2=CC=C(S2)C2=CN=C(N)N=C2)C1=O)=C/F IMDXJKUXQWLVSV-XCVCLJGOSA-N 0.000 claims 1
- WHJDKWIGXYXDBK-LFYBBSHMSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(2-ethoxypyrimidin-5-yl)thiophen-2-yl]methyl]-1,2,4-triazol-3-one Chemical compound CCOC1=NC=C(C=N1)C1=CC=C(CN2C=NN(C\C(CN)=C\F)C2=O)S1 WHJDKWIGXYXDBK-LFYBBSHMSA-N 0.000 claims 1
- FSMUBHOWLGCFPN-MDWZMJQESA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(3-methylsulfonylphenyl)thiophen-2-yl]methyl]-1,2,4-triazol-3-one Chemical compound CS(=O)(=O)C1=CC=CC(=C1)C1=CC=C(CN2C=NN(C\C(CN)=C\F)C2=O)S1 FSMUBHOWLGCFPN-MDWZMJQESA-N 0.000 claims 1
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| WO2016007727A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
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| TW201722958A (zh) | 2015-09-15 | 2017-07-01 | 葛蘭素史克智慧財產（第二）有限公司 | 化學化合物 |
| JP6849197B2 (ja) | 2016-02-12 | 2021-03-24 | ファーマクシス リミテッド | リジルオキシダーゼのインドールおよびアザインドールハロアリルアミン誘導体阻害剤およびその使用 |
| WO2017191112A1 (en) | 2016-05-03 | 2017-11-09 | Bayer Pharma Aktiengesellschaft | Fluoroalkyl-substituted aryltriazole derivatives and uses thereof |
| WO2018027892A1 (en) | 2016-08-12 | 2018-02-15 | Eli Lilly And Company | Amino pyrimidine ssao inhibitors |
| BR112019005930A2 (pt) | 2016-10-19 | 2019-06-11 | Boehringer Ingelheim Int | combinações compreendendo um inibidor de ssao/vap-1 e um inibidor de sglt2, e usos das mesmas |
| US20200069648A1 (en) | 2017-03-02 | 2020-03-05 | Pharmaxis Ltd. | Haloallylamine pyrazole derivative inhibitors of lysyl oxidases and uses thereof |
| US20200087248A1 (en) | 2017-04-28 | 2020-03-19 | Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. | Fluoroallylamine Derivative And Use Thereof |
| AU2018287777B2 (en) | 2017-06-20 | 2020-05-21 | Shandong Danhong Pharmaceutical Co., Ltd. | SSAO inhibitor |
| CN109810041B (zh) | 2017-11-21 | 2023-08-15 | 药捷安康(南京)科技股份有限公司 | 卤代烯丙基胺类ssao/vap-1抑制剂及其应用 |
| CN109988109B (zh) | 2017-12-29 | 2020-12-29 | 广东东阳光药业有限公司 | 抑制ssao/vap-1的胺类化合物及其用途 |
| KR20190110740A (ko) | 2018-03-21 | 2019-10-01 | 주식회사유한양행 | 신규의 아릴 또는 헤테로아릴 트라이아졸론 유도체 또는 이의 염 및 이를 포함하는 약학 조성물 |
| KR20190110736A (ko) * | 2018-03-21 | 2019-10-01 | 주식회사유한양행 | 신규의 트라이아졸론 유도체 또는 이의 염 및 이를 포함하는 약학 조성물 |
| CN110938059A (zh) | 2018-09-25 | 2020-03-31 | 上海轶诺药业有限公司 | 胺基脲敏感性胺氧化酶抑制剂制备及其应用 |
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| CN112789277B (zh) | 2018-10-22 | 2022-11-04 | 广东东阳光药业有限公司 | 胍类衍生物及其用途 |
| AU2019365213A1 (en) | 2018-10-24 | 2021-06-03 | Metacrine, Inc. | SSAO inhibitors and uses thereof |
| TWI835945B (zh) | 2018-12-14 | 2024-03-21 | 南韓商柳韓洋行股份有限公司 | 3,3-二氟烯丙胺化物或其鹽及包含彼的醫藥組合物 |
| TW202039486A (zh) | 2018-12-14 | 2020-11-01 | 南韓商柳韓洋行股份有限公司 | 三唑并吡啶-3-酮化物或其鹽及包含彼之醫藥組合物 |
| BR112021013429A2 (pt) | 2019-01-11 | 2021-10-19 | Nanjing Transthera Biosciences Co., Ltd. | Composto, composição farmacêutica, e, uso do composto |
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2018
- 2018-03-21 KR KR1020180032548A patent/KR20190110736A/ko active Pending
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2019
- 2019-03-20 JP JP2020550176A patent/JP7383627B2/ja active Active
- 2019-03-20 WO PCT/IB2019/052278 patent/WO2019180646A1/en not_active Ceased
- 2019-03-20 US US16/359,985 patent/US10995086B2/en active Active
- 2019-03-20 CA CA3093057A patent/CA3093057A1/en active Pending
- 2019-03-20 AU AU2019237344A patent/AU2019237344B2/en not_active Ceased
- 2019-03-20 KR KR1020207029750A patent/KR102788118B1/ko active Active
- 2019-03-20 EP EP19772403.2A patent/EP3768675B1/en active Active
- 2019-03-20 CN CN201980020696.5A patent/CN111886233B/zh active Active
- 2019-03-21 TW TW108109864A patent/TWI803600B/zh not_active IP Right Cessation
- 2019-03-21 AR ARP190100713A patent/AR115007A1/es not_active Application Discontinuation
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2021
- 2021-03-22 US US17/208,887 patent/US11780830B2/en active Active
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2023
- 2023-08-07 JP JP2023128580A patent/JP2023145748A/ja active Pending
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