JPWO2019180644A5 - - Google Patents
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- Publication number
- JPWO2019180644A5 JPWO2019180644A5 JP2020550099A JP2020550099A JPWO2019180644A5 JP WO2019180644 A5 JPWO2019180644 A5 JP WO2019180644A5 JP 2020550099 A JP2020550099 A JP 2020550099A JP 2020550099 A JP2020550099 A JP 2020550099A JP WO2019180644 A5 JPWO2019180644 A5 JP WO2019180644A5
- Authority
- JP
- Japan
- Prior art keywords
- triazole
- dihydro
- aminomethyl
- fluoropropa
- hydrochloride
- 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 description 111
- 150000001875 compounds Chemical class 0.000 claims description 36
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 claims description 7
- -1 benzoxazinezole Natural products 0.000 claims 52
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 42
- 150000003839 salts Chemical class 0.000 claims 30
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 24
- 125000004122 cyclic group Chemical group 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 10
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-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
- 235000010290 biphenyl Nutrition 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 5
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 5
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 4
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical group O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 4
- 229930192474 thiophene Natural products 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 3
- MENHXVNCWVKFRA-UHFFFAOYSA-N 1,4-oxazin-2-one Chemical compound O=C1C=NC=CO1 MENHXVNCWVKFRA-UHFFFAOYSA-N 0.000 claims 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 3
- LWTIGYSPAXKMDG-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole Chemical compound C1NC=CN1 LWTIGYSPAXKMDG-UHFFFAOYSA-N 0.000 claims 3
- LTWFBZQFHPDLNU-UHFFFAOYSA-N 2,3-dihydro-1h-pyrido[2,3-b][1,4]oxazine Chemical compound C1=CC=C2NCCOC2=N1 LTWFBZQFHPDLNU-UHFFFAOYSA-N 0.000 claims 3
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical group C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 3
- GZOJTRITAZODJV-UHFFFAOYSA-N 3,1-benzoxazin-2-one Chemical compound C1=CC=CC2=COC(=O)N=C21 GZOJTRITAZODJV-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
- QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 claims 3
- XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical compound O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 claims 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 3
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 3
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 3
- 239000004305 biphenyl Substances 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 150000002240 furans Chemical class 0.000 claims 3
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims 3
- LIRDJALZRPAZOR-UHFFFAOYSA-N indolin-3-one Chemical compound C1=CC=C2C(=O)CNC2=C1 LIRDJALZRPAZOR-UHFFFAOYSA-N 0.000 claims 3
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 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
- 125000001715 oxadiazolyl 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
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 3
- 229920002554 vinyl polymer Polymers 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 2
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims 2
- QQVXDMFULJVZLA-UHFFFAOYSA-N 3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazine Chemical compound C1=CN=C2NCCOC2=C1 QQVXDMFULJVZLA-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 230000001587 cholestatic effect Effects 0.000 claims 2
- 230000002440 hepatic effect Effects 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 230000003211 malignant effect Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- OVBSMCVFDKBNOZ-UHFFFAOYSA-N 1,4-oxazin-2-one;hydrochloride Chemical compound Cl.O=C1C=NC=CO1 OVBSMCVFDKBNOZ-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
- LNNAVTXQURDFNC-ZFXMFRGYSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(3,4-difluorophenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccc(F)c(F)c2)c1=O)=C/F LNNAVTXQURDFNC-ZFXMFRGYSA-N 0.000 claims 1
- HGFFVIWRPPMYKR-SZKNIZGXSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(3-bromophenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(Br)c2)c1=O)=C/F HGFFVIWRPPMYKR-SZKNIZGXSA-N 0.000 claims 1
- XIDNWQYVUFHKAQ-NSPIFIKESA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(3-isoquinolin-4-ylphenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2cncc3ccccc23)c1=O)=C/F XIDNWQYVUFHKAQ-NSPIFIKESA-N 0.000 claims 1
- KFXKQAUEQIFLDG-NTUHNPAUSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(3-methyl-5-piperazin-1-ylpyridin-2-yl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=NC=C(C=C1C)N1CCNCC1)=C\F KFXKQAUEQIFLDG-NTUHNPAUSA-N 0.000 claims 1
- FHTHSCFVCJAAFC-FNXZNAJJSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(3-pyridin-3-ylphenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2cccnc2)c1=O)=C/F FHTHSCFVCJAAFC-FNXZNAJJSA-N 0.000 claims 1
- XTXUBEUHLZFYFD-CDQVLDCRSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-2,5-difluorophenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cc(F)c(Br)cc2F)c1=O)=C/F XTXUBEUHLZFYFD-CDQVLDCRSA-N 0.000 claims 1
- AKGRZPCKCYAPMI-CDQVLDCRSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-2,6-difluorophenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2c(F)cc(Br)cc2F)c1=O)=C/F AKGRZPCKCYAPMI-CDQVLDCRSA-N 0.000 claims 1
- CZAOVKWJEGRXFJ-ZFXMFRGYSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-2-fluorophenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccc(Br)cc2F)c1=O)=C/F CZAOVKWJEGRXFJ-ZFXMFRGYSA-N 0.000 claims 1
- JTWWQVXWRVGBMG-CDQVLDCRSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-3,5-difluorophenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cc(F)c(Br)c(F)c2)c1=O)=C/F JTWWQVXWRVGBMG-CDQVLDCRSA-N 0.000 claims 1
- MWRNTNCCYLXFNY-ZFXMFRGYSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-3-fluorophenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccc(Br)c(F)c2)c1=O)=C/F MWRNTNCCYLXFNY-ZFXMFRGYSA-N 0.000 claims 1
- UAXJKRJRWXGIIP-SZKNIZGXSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-3-methoxyphenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.COc1cc(ccc1Br)-n1cnn(C\C(CN)=C\F)c1=O UAXJKRJRWXGIIP-SZKNIZGXSA-N 0.000 claims 1
- GAHNPMHFRGVQFU-OAZHBLANSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-3-methylphenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(ccc1Br)-n1cnn(C\C(CN)=C\F)c1=O GAHNPMHFRGVQFU-OAZHBLANSA-N 0.000 claims 1
- OVLNEZKGFPFKBE-WEVVVXLNSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromophenyl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=CC=C(C=C1)Br)=C\F OVLNEZKGFPFKBE-WEVVVXLNSA-N 0.000 claims 1
- JKOHPDMNLSJUQE-SZKNIZGXSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-fluorophenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccc(F)cc2)c1=O)=C/F JKOHPDMNLSJUQE-SZKNIZGXSA-N 0.000 claims 1
- LCSBIYHTPMIVEZ-QFHYWFJHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-phenylmethoxyphenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccc(OCc3ccccc3)cc2)c1=O)=C/F LCSBIYHTPMIVEZ-QFHYWFJHSA-N 0.000 claims 1
- OROWTEQIOPGQCQ-RRWNKNEUSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromo-1,3-thiazol-2-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ncc(Br)s2)c1=O)=C/F OROWTEQIOPGQCQ-RRWNKNEUSA-N 0.000 claims 1
- ZMHCMQRENOKDPW-MXZHIVQLSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromo-2-methoxy-4-morpholin-4-ylphenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.COc1cc(N2CCOCC2)c(Br)cc1-n1cnn(C\C(CN)=C\F)c1=O ZMHCMQRENOKDPW-MXZHIVQLSA-N 0.000 claims 1
- HAKTYEDEZRQLLX-NIBQXPITSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromo-3-fluoropyridin-2-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ncc(Br)cc2F)c1=O)=C/F HAKTYEDEZRQLLX-NIBQXPITSA-N 0.000 claims 1
- MJPYHQVGWJYBSE-JSGFVSQVSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromo-3-methylpyridin-2-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(Br)cnc1-n1cnn(C\C(CN)=C\F)c1=O MJPYHQVGWJYBSE-JSGFVSQVSA-N 0.000 claims 1
- YCBYNLCFSOXSRD-JSGFVSQVSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromo-4-methylpyridin-2-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(ncc1Br)-n1cnn(C\C(CN)=C\F)c1=O YCBYNLCFSOXSRD-JSGFVSQVSA-N 0.000 claims 1
- MIHKMVHYVACGRV-LREOWRDNSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromopyrazin-2-yl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=NC=C(N=C1)Br)=C\F MIHKMVHYVACGRV-LREOWRDNSA-N 0.000 claims 1
- FEWZFLYLSRJMLB-DCDCITSCSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromopyridin-2-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccc(Br)cn2)c1=O)=C/F FEWZFLYLSRJMLB-DCDCITSCSA-N 0.000 claims 1
- NWKVPGAPNWCQJK-JSGFVSQVSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(6-bromo-4-methylpyridin-3-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(Br)ncc1-n1cnn(C\C(CN)=C\F)c1=O NWKVPGAPNWCQJK-JSGFVSQVSA-N 0.000 claims 1
- LYSKIQZSHQMLGO-XBXARRHUSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(6-bromopyridin-2-yl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=NC(=CC=C1)Br)=C\F LYSKIQZSHQMLGO-XBXARRHUSA-N 0.000 claims 1
- HFIDCJRREBSNJY-DCDCITSCSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(6-bromopyridin-3-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccc(Br)nc2)c1=O)=C/F HFIDCJRREBSNJY-DCDCITSCSA-N 0.000 claims 1
- VQOIGMJUXCYREY-CLNHMMGSSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[2-(4-morpholin-4-ylphenyl)pyridin-4-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccnc(c2)-c2ccc(cc2)N2CCOCC2)c1=O)=C/F VQOIGMJUXCYREY-CLNHMMGSSA-N 0.000 claims 1
- PKMLMKFUNLFMJM-XNTDXEJSSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[2-methyl-3-(4-methylsulfonylphenyl)phenyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C=1C(=C(C=CC=1)C1=CC=C(C=C1)S(=O)(=O)C)C)=C\F PKMLMKFUNLFMJM-XNTDXEJSSA-N 0.000 claims 1
- CLQDOBNWZVNGEF-LFIBNONCSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[2-methyl-3-[4-(1,2-oxazol-3-yl)phenyl]phenyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C=1C(=C(C=CC=1)C1=CC=C(C=C1)C1=NOC=C1)C)=C\F CLQDOBNWZVNGEF-LFIBNONCSA-N 0.000 claims 1
- LUHMMDFKCRMTJW-IGUOPLJTSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-1,2,4-triazol-3-one dihydrochloride Chemical compound Cl.Cl.NC\C(Cn1ncn(-c2cccc(c2)C2=CCNCC2)c1=O)=C/F LUHMMDFKCRMTJW-IGUOPLJTSA-N 0.000 claims 1
- KLNYFUSRICQZQH-RIYZIHGNSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(1,3-benzodioxol-5-yl)-2-methylphenyl]-1,2,4-triazol-3-one Chemical compound CC1=C(C=CC=C1C1=CC2=C(OCO2)C=C1)N1C=NN(C\C(CN)=C\F)C1=O KLNYFUSRICQZQH-RIYZIHGNSA-N 0.000 claims 1
- XWRRDIAOOJOBOJ-FNXZNAJJSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(1,3-benzodioxol-5-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2ccc3OCOc3c2)c1=O)=C/F XWRRDIAOOJOBOJ-FNXZNAJJSA-N 0.000 claims 1
- DPOFQJPPPSQEPV-KMZJGFRYSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(1-benzothiophen-2-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2cc3ccccc3s2)c1=O)=C/F DPOFQJPPPSQEPV-KMZJGFRYSA-N 0.000 claims 1
- DIJBNXFDXBZPJJ-KYIGKLDSSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(1H-indol-3-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2c[nH]c3ccccc23)c1=O)=C/F DIJBNXFDXBZPJJ-KYIGKLDSSA-N 0.000 claims 1
- UJWYIJIOHLAUKI-KMZJGFRYSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(1H-indol-4-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2cccc3[nH]ccc23)c1=O)=C/F UJWYIJIOHLAUKI-KMZJGFRYSA-N 0.000 claims 1
- JAXHPHMUHNZAMB-MDWZMJQESA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(2,1,3-benzoxadiazol-5-yl)-2-methylphenyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=C(C(=CC=C1)C1=CC=2C(=NON=2)C=C1)C)=C\F JAXHPHMUHNZAMB-MDWZMJQESA-N 0.000 claims 1
- YHPMMBQBDQSOEO-MXZHIVQLSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(2,1,3-benzoxadiazol-5-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2ccc3nonc3c2)c1=O)=C/F YHPMMBQBDQSOEO-MXZHIVQLSA-N 0.000 claims 1
- IQORWWWEQYNPRZ-KJEVSKRMSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(2-methoxypyridin-4-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.COc1cc(ccn1)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O IQORWWWEQYNPRZ-KJEVSKRMSA-N 0.000 claims 1
- TXQFSQZUCNWMIQ-AWFSDRIXSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(2-methylpyrimidin-5-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1ncc(cn1)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O TXQFSQZUCNWMIQ-AWFSDRIXSA-N 0.000 claims 1
- IBHZRWLTOIUJLR-LZMXEPDESA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(2-pyridin-3-ylethynyl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)C#Cc2cccnc2)c1=O)=C/F IBHZRWLTOIUJLR-LZMXEPDESA-N 0.000 claims 1
- GYLPFOOMKPDYIG-KMZJGFRYSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(4-methylsulfonylphenyl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CS(=O)(=O)c1ccc(cc1)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O GYLPFOOMKPDYIG-KMZJGFRYSA-N 0.000 claims 1
- SBWLJZVZWLHIIP-IWSIBTJSSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(4-morpholin-4-ylphenyl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2ccc(cc2)N2CCOCC2)c1=O)=C/F SBWLJZVZWLHIIP-IWSIBTJSSA-N 0.000 claims 1
- RNPMQEADBTXLRJ-RRAJOLSVSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(6-chloropyridin-3-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2ccc(Cl)nc2)c1=O)=C/F RNPMQEADBTXLRJ-RRAJOLSVSA-N 0.000 claims 1
- FXJWZUSCBYCUJM-FNXZNAJJSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(6-methoxypyridin-3-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.COc1ccc(cn1)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O FXJWZUSCBYCUJM-FNXZNAJJSA-N 0.000 claims 1
- BCUVGSARMMJDSW-YFMOEUEHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(6-morpholin-4-ylpyridin-3-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2ccc(nc2)N2CCOCC2)c1=O)=C/F BCUVGSARMMJDSW-YFMOEUEHSA-N 0.000 claims 1
- DZNWQCFSFMYHIA-YFMOEUEHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(8-methylquinolin-5-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1ccc(-c2cccc(c2)-n2cnn(C\C(CN)=C\F)c2=O)c2cccnc12 DZNWQCFSFMYHIA-YFMOEUEHSA-N 0.000 claims 1
- BFLYPRHGBLYIHK-NTEUORMPSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-[3-(1,2,4-oxadiazol-3-yl)phenyl]phenyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C=1C=C(C=CC=1)C1=CC(=CC=C1)C1=NOC=N1)=C\F BFLYPRHGBLYIHK-NTEUORMPSA-N 0.000 claims 1
- QYCUIXZJHDTPNJ-NBVRZTHBSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-[3-(4-methylsulfonylphenyl)phenyl]phenyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C=1C=C(C=CC=1)C1=CC(=CC=C1)C1=CC=C(C=C1)S(=O)(=O)C)=C\F QYCUIXZJHDTPNJ-NBVRZTHBSA-N 0.000 claims 1
- DCINTCFSWUEVQA-YFMOEUEHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-[3-(5-propan-2-yl-1,2,4-oxadiazol-3-yl)phenyl]phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CC(C)c1nc(no1)-c1cccc(c1)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O DCINTCFSWUEVQA-YFMOEUEHSA-N 0.000 claims 1
- GDYHNUVTXZTYJZ-NTEUORMPSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-[4-(1,2,4-oxadiazol-3-yl)phenyl]phenyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C=1C=C(C=CC=1)C1=CC=C(C=C1)C1=NOC=N1)=C\F GDYHNUVTXZTYJZ-NTEUORMPSA-N 0.000 claims 1
- LGJDYKHLUYPXSZ-LSJACRKWSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-[4-(4-methylsulfonylphenyl)phenyl]phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CS(=O)(=O)c1ccc(cc1)-c1ccc(cc1)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O LGJDYKHLUYPXSZ-LSJACRKWSA-N 0.000 claims 1
- AWAQZXWACXBZEY-YFMOEUEHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-[4-(5-propan-2-yl-1,2,4-oxadiazol-3-yl)phenyl]phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CC(C)c1nc(no1)-c1ccc(cc1)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O AWAQZXWACXBZEY-YFMOEUEHSA-N 0.000 claims 1
- MDTOPIOIOUNJRU-KRWCAOSLSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-[4-(dimethylamino)phenyl]phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CN(C)c1ccc(cc1)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O MDTOPIOIOUNJRU-KRWCAOSLSA-N 0.000 claims 1
- WRXRNZISFPULOK-IWSIBTJSSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-[4-(morpholine-4-carbonyl)phenyl]phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2ccc(cc2)C(=O)N2CCOCC2)c1=O)=C/F WRXRNZISFPULOK-IWSIBTJSSA-N 0.000 claims 1
- QQPXUKAFHKSFSM-KJEVSKRMSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-[4-(trifluoromethoxy)phenyl]phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2ccc(OC(F)(F)F)cc2)c1=O)=C/F QQPXUKAFHKSFSM-KJEVSKRMSA-N 0.000 claims 1
- KESYTKVNHKBTQS-RRAJOLSVSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-[6-(trifluoromethyl)pyridin-3-yl]phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2ccc(nc2)C(F)(F)F)c1=O)=C/F KESYTKVNHKBTQS-RRAJOLSVSA-N 0.000 claims 1
- NZQCBRZZSAPKCM-SJDTYFKWSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-methyl-5-(4-piperazin-1-ylphenyl)pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(cnc1-n1cnn(C\C(CN)=C\F)c1=O)-c1ccc(cc1)N1CCNCC1 NZQCBRZZSAPKCM-SJDTYFKWSA-N 0.000 claims 1
- RJFNRUMFPROAIB-QOVZSLTQSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-methyl-5-(6-morpholin-4-ylpyridin-3-yl)pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(cnc1-n1cnn(C\C(CN)=C\F)c1=O)-c1ccc(nc1)N1CCOCC1 RJFNRUMFPROAIB-QOVZSLTQSA-N 0.000 claims 1
- BMJZKQGAKHZXQE-NTUHNPAUSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-methyl-5-[3-(2H-tetrazol-5-yl)phenyl]pyridin-2-yl]-1,2,4-triazol-3-one Chemical compound CC1=CC(=CN=C1N1C=NN(C\C(CN)=C\F)C1=O)C1=CC(=CC=C1)C1=NN=NN1 BMJZKQGAKHZXQE-NTUHNPAUSA-N 0.000 claims 1
- RRBWIORHEYFAEU-SJDTYFKWSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-methyl-5-[4-(morpholine-4-carbonyl)phenyl]pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(cnc1-n1cnn(C\C(CN)=C\F)c1=O)-c1ccc(cc1)C(=O)N1CCOCC1 RRBWIORHEYFAEU-SJDTYFKWSA-N 0.000 claims 1
- AENBGUFHEYFEDD-NKPNRJPBSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-methyl-5-[6-(trifluoromethyl)pyridin-3-yl]pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(cnc1-n1cnn(C\C(CN)=C\F)c1=O)-c1ccc(nc1)C(F)(F)F AENBGUFHEYFEDD-NKPNRJPBSA-N 0.000 claims 1
- WSCVVORBVGPFMG-KCUXUEJTSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-methyl-6-[4-(morpholine-4-carbonyl)phenyl]pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1ccc(nc1-n1cnn(C\C(CN)=C\F)c1=O)-c1ccc(cc1)C(=O)N1CCOCC1 WSCVVORBVGPFMG-KCUXUEJTSA-N 0.000 claims 1
- MFDGZIOBZHZYTJ-RRAJOLSVSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[4-(1,3-benzodioxol-5-yl)-2-fluorophenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccc(cc2F)-c2ccc3OCOc3c2)c1=O)=C/F MFDGZIOBZHZYTJ-RRAJOLSVSA-N 0.000 claims 1
- BBWOLVFWPVKNNX-RVDQCCQOSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[4-(2,1,3-benzoxadiazol-5-yl)-2-fluorophenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccc(cc2F)-c2ccc3nonc3c2)c1=O)=C/F BBWOLVFWPVKNNX-RVDQCCQOSA-N 0.000 claims 1
- CTUNBHGIAJQWFB-GYVLLFFHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[4-(2-pyridin-2-ylethynyl)pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cc(ccn2)C#Cc2ccccn2)c1=O)=C/F CTUNBHGIAJQWFB-GYVLLFFHSA-N 0.000 claims 1
- HNHSWLUBZFTPRG-QOVZSLTQSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[4-(2-pyridin-3-ylethynyl)pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cc(ccn2)C#Cc2cccnc2)c1=O)=C/F HNHSWLUBZFTPRG-QOVZSLTQSA-N 0.000 claims 1
- RIXYHBZMYPFTHQ-QFHYWFJHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[4-(2-pyridin-4-ylethynyl)pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cc(ccn2)C#Cc2ccncc2)c1=O)=C/F RIXYHBZMYPFTHQ-QFHYWFJHSA-N 0.000 claims 1
- AXFZXTMTUBTMTR-UKTHLTGXSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[4-(4-methylsulfonylphenyl)pyridin-2-yl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=NC=CC(=C1)C1=CC=C(C=C1)S(=O)(=O)C)=C\F AXFZXTMTUBTMTR-UKTHLTGXSA-N 0.000 claims 1
- NBEWFSLBYUPTKB-VNFWPAMTSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[4-[(E)-2-phenylethenyl]pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cc(\C=C\c3ccccc3)ccn2)c1=O)=C/F NBEWFSLBYUPTKB-VNFWPAMTSA-N 0.000 claims 1
- ALFBDHUCRJXZTA-GXDHUFHOSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[4-[4-(1,2-oxazol-3-yl)phenyl]pyridin-2-yl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=NC=CC(=C1)C1=CC=C(C=C1)C1=NOC=C1)=C\F ALFBDHUCRJXZTA-GXDHUFHOSA-N 0.000 claims 1
- UJBGRVKPMCCYSD-CXUHLZMHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[4-methyl-6-(6-morpholin-4-ylpyridin-3-yl)pyridin-3-yl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C=1C(=CC(=NC=1)C=1C=NC(=CC=1)N1CCOCC1)C)=C\F UJBGRVKPMCCYSD-CXUHLZMHSA-N 0.000 claims 1
- KKUINFYWYMVEOJ-AWFSDRIXSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[5-(1,3-benzodioxol-5-yl)-3-methylpyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(cnc1-n1cnn(C\C(CN)=C\F)c1=O)-c1ccc2OCOc2c1 KKUINFYWYMVEOJ-AWFSDRIXSA-N 0.000 claims 1
- GGYJLYLDZXXUPC-AWNIVKPZSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[5-(1,3-benzodioxol-5-yl)-4-methylpyridin-2-yl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=NC=C(C(=C1)C)C1=CC2=C(OCO2)C=C1)=C\F GGYJLYLDZXXUPC-AWNIVKPZSA-N 0.000 claims 1
- QOJQIHFOHCMAKX-NYYWCZLTSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[5-(1H-indazol-6-yl)pyrazin-2-yl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=NC=C(N=C1)C1=CC=C2C=NNC2=C1)=C\F QOJQIHFOHCMAKX-NYYWCZLTSA-N 0.000 claims 1
- OTKQXQMOGWINGN-WXIWBVQFSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[5-(2,1,3-benzoxadiazol-5-yl)-3-methylpyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(cnc1-n1cnn(C\C(CN)=C\F)c1=O)-c1ccc2nonc2c1 OTKQXQMOGWINGN-WXIWBVQFSA-N 0.000 claims 1
- XJCYCNHOVMLTGS-WUXMJOGZSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[5-(4-methylsulfonylphenyl)pyrazin-2-yl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=NC=C(N=C1)C1=CC=C(C=C1)S(=O)(=O)C)=C\F XJCYCNHOVMLTGS-WUXMJOGZSA-N 0.000 claims 1
- KGHXGEFFAOYDEZ-VGOFMYFVSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[5-(6-morpholin-4-ylpyridin-3-yl)pyrazin-2-yl]-1,2,4-triazol-3-one Chemical compound NC\C(CN1N=CN(C1=O)C1=CN=C(C=N1)C1=CC=C(N=C1)N1CCOCC1)=C/F KGHXGEFFAOYDEZ-VGOFMYFVSA-N 0.000 claims 1
- FFVCKBHKJKCOQX-BJMVGYQFSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[5-[3-(2H-tetrazol-5-yl)phenyl]-1,3-thiazol-2-yl]-1,2,4-triazol-3-one Chemical compound NC\C(CN1N=CN(C1=O)C1=NC=C(S1)C1=CC(=CC=C1)C1=NN=NN1)=C/F FFVCKBHKJKCOQX-BJMVGYQFSA-N 0.000 claims 1
- AYPIUPRZLFMDSD-FTPOTTDRSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-(1,3-benzodioxol-5-yl)-3-methylpyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1ccc(nc1-n1cnn(C\C(CN)=C\F)c1=O)-c1ccc2OCOc2c1 AYPIUPRZLFMDSD-FTPOTTDRSA-N 0.000 claims 1
- KHEGOJHNUXMICK-AWNIVKPZSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-(1,3-benzodioxol-5-yl)-5-methylpyridin-3-yl]-1,2,4-triazol-3-one Chemical compound CC1=C(N=CC(=C1)N1C=NN(C\C(CN)=C\F)C1=O)C1=CC2=C(OCO2)C=C1 KHEGOJHNUXMICK-AWNIVKPZSA-N 0.000 claims 1
- QFMUMDOMKHUJJU-WUXMJOGZSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-(2,1,3-benzoxadiazol-5-yl)-4-methylpyridin-3-yl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C=1C=NC(=CC=1C)C1=CC=2C(=NON=2)C=C1)=C\F QFMUMDOMKHUJJU-WUXMJOGZSA-N 0.000 claims 1
- KZXOJSXVIPEPDR-CLNHMMGSSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-(4-piperazin-1-ylphenyl)pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(n2)-c2ccc(cc2)N2CCNCC2)c1=O)=C/F KZXOJSXVIPEPDR-CLNHMMGSSA-N 0.000 claims 1
- GCDUKJNOFJWINK-CLNHMMGSSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-(4-pyrrolidin-1-ylphenyl)pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(n2)-c2ccc(cc2)N2CCCC2)c1=O)=C/F GCDUKJNOFJWINK-CLNHMMGSSA-N 0.000 claims 1
- RYGYPCXHOSALJV-MZGBUDIQSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(\C=C\c3ccc(cc3)C(F)(F)F)n2)c1=O)=C/F RYGYPCXHOSALJV-MZGBUDIQSA-N 0.000 claims 1
- LADOWRDSUSGOTQ-DLBFRJOTSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-[(E)-2-thiophen-3-ylethenyl]pyridin-2-yl]-1,2,4-triazol-3-one Chemical compound NC\C(CN1N=CN(C1=O)C1=NC(\C=C\C2=CSC=C2)=CC=C1)=C/F LADOWRDSUSGOTQ-DLBFRJOTSA-N 0.000 claims 1
- WEPXKCSAIMKPDF-FJUODKGNSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-[2-(1-methylpyrazol-4-yl)ethynyl]pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cn1cc(cn1)C#Cc1cccc(n1)-n1cnn(C\C(CN)=C\F)c1=O WEPXKCSAIMKPDF-FJUODKGNSA-N 0.000 claims 1
- ATDUFYSQWQFXCS-XNTDXEJSSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-[3-(5-propan-2-yl-1,2,4-oxadiazol-3-yl)phenyl]pyridin-2-yl]-1,2,4-triazol-3-one Chemical compound CC(C)C1=NC(=NO1)C1=CC=CC(=C1)C1=CC=CC(=N1)N1C=NN(C\C(CN)=C\F)C1=O ATDUFYSQWQFXCS-XNTDXEJSSA-N 0.000 claims 1
- CBZXNWLWZPFVAT-KMZJGFRYSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-[3-(dimethylamino)phenyl]pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CN(C)c1cccc(c1)-c1cccc(n1)-n1cnn(C\C(CN)=C\F)c1=O CBZXNWLWZPFVAT-KMZJGFRYSA-N 0.000 claims 1
- XJNHZNGUHNRPGR-GXDHUFHOSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-[4-(1,2-oxazol-3-yl)phenyl]pyridin-2-yl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=NC(=CC=C1)C1=CC=C(C=C1)C1=NOC=C1)=C\F XJNHZNGUHNRPGR-GXDHUFHOSA-N 0.000 claims 1
- OHOWFSBDSJXRCD-XNTDXEJSSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-[4-(5-propan-2-yl-1,2,4-oxadiazol-3-yl)phenyl]pyridin-2-yl]-1,2,4-triazol-3-one Chemical compound CC(C)C1=NC(=NO1)C1=CC=C(C=C1)C1=CC=CC(=N1)N1C=NN(C\C(CN)=C\F)C1=O OHOWFSBDSJXRCD-XNTDXEJSSA-N 0.000 claims 1
- HNNLSKUEHRNMAG-RRAJOLSVSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-[6-(dimethylamino)-5-fluoropyridin-3-yl]pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CN(C)c1ncc(cc1F)-c1cccc(n1)-n1cnn(C\C(CN)=C\F)c1=O HNNLSKUEHRNMAG-RRAJOLSVSA-N 0.000 claims 1
- YTNULMSPASJTCG-FNXZNAJJSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[6-[6-(dimethylamino)pyridin-3-yl]pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CN(C)c1ccc(cn1)-c1cccc(n1)-n1cnn(C\C(CN)=C\F)c1=O YTNULMSPASJTCG-FNXZNAJJSA-N 0.000 claims 1
- NPJYUSJLXTUPIH-WYLUAFJRSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(1,3-thiazol-2-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2nccs2)c1=O)=C\F NPJYUSJLXTUPIH-WYLUAFJRSA-N 0.000 claims 1
- QVRHWSQWMHSWOE-YWEYNIOJSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(3,4-difluorophenyl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=CC(=C(C=C1)F)F)=C/F QVRHWSQWMHSWOE-YWEYNIOJSA-N 0.000 claims 1
- HGFFVIWRPPMYKR-UYTGOYFPSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(3-bromophenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(Br)c2)c1=O)=C\F HGFFVIWRPPMYKR-UYTGOYFPSA-N 0.000 claims 1
- AKGRZPCKCYAPMI-WYLUAFJRSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-2,6-difluorophenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2c(F)cc(Br)cc2F)c1=O)=C\F AKGRZPCKCYAPMI-WYLUAFJRSA-N 0.000 claims 1
- CZAOVKWJEGRXFJ-ZYFYRQFPSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-2-fluorophenyl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccc(Br)cc2F)c1=O)=C\F CZAOVKWJEGRXFJ-ZYFYRQFPSA-N 0.000 claims 1
- LNICKCYYFKZKAS-CLTKARDFSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-3,5-difluorophenyl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=CC(=C(C(=C1)F)Br)F)=C/F LNICKCYYFKZKAS-CLTKARDFSA-N 0.000 claims 1
- IVTYTVNABFOAGQ-YWEYNIOJSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-3-fluorophenyl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=CC(=C(C=C1)Br)F)=C/F IVTYTVNABFOAGQ-YWEYNIOJSA-N 0.000 claims 1
- KUGYRJSUFNPQRX-UITAMQMPSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-3-methoxyphenyl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=CC(=C(C=C1)Br)OC)=C/F KUGYRJSUFNPQRX-UITAMQMPSA-N 0.000 claims 1
- DCLRXPMXQQLCDM-YHYXMXQVSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromo-3-methylphenyl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=CC(=C(C=C1)Br)C)=C/F DCLRXPMXQQLCDM-YHYXMXQVSA-N 0.000 claims 1
- OVLNEZKGFPFKBE-UITAMQMPSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-bromophenyl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=CC=C(C=C1)Br)=C/F OVLNEZKGFPFKBE-UITAMQMPSA-N 0.000 claims 1
- JLDNBQOBJKSYOQ-UITAMQMPSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-fluorophenyl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=CC=C(C=C1)F)=C/F JLDNBQOBJKSYOQ-UITAMQMPSA-N 0.000 claims 1
- CUXPVTTZXJOTGW-YBEGLDIGSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(4-phenylmethoxyphenyl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C1=CC=C(C=C1)OCC1=CC=CC=C1)=C/F CUXPVTTZXJOTGW-YBEGLDIGSA-N 0.000 claims 1
- OROWTEQIOPGQCQ-WLVHXSKESA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromo-1,3-thiazol-2-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ncc(Br)s2)c1=O)=C\F OROWTEQIOPGQCQ-WLVHXSKESA-N 0.000 claims 1
- HAKTYEDEZRQLLX-YMWUIOJXSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromo-3-fluoropyridin-2-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ncc(Br)cc2F)c1=O)=C\F HAKTYEDEZRQLLX-YMWUIOJXSA-N 0.000 claims 1
- MJPYHQVGWJYBSE-WPUSIDMCSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromo-3-methylpyridin-2-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(Br)cnc1-n1cnn(C\C(CN)=C/F)c1=O MJPYHQVGWJYBSE-WPUSIDMCSA-N 0.000 claims 1
- YCBYNLCFSOXSRD-WPUSIDMCSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromo-4-methylpyridin-2-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(ncc1Br)-n1cnn(C\C(CN)=C/F)c1=O YCBYNLCFSOXSRD-WPUSIDMCSA-N 0.000 claims 1
- FEWZFLYLSRJMLB-NGRDVXTNSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(5-bromopyridin-2-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ccc(Br)cn2)c1=O)=C\F FEWZFLYLSRJMLB-NGRDVXTNSA-N 0.000 claims 1
- MWOXPBMPQOONII-WPUSIDMCSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(6-bromo-5-methylpyridin-3-yl)-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(cnc1Br)-n1cnn(C\C(CN)=C/F)c1=O MWOXPBMPQOONII-WPUSIDMCSA-N 0.000 claims 1
- JYLZHSNPRRWTCH-BAQGIRSFSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-(6-bromopyridin-3-yl)-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)C=1C=NC(=CC=1)Br)=C/F JYLZHSNPRRWTCH-BAQGIRSFSA-N 0.000 claims 1
- XWRRDIAOOJOBOJ-MGAWDJABSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(1,3-benzodioxol-5-yl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2ccc3OCOc3c2)c1=O)=C\F XWRRDIAOOJOBOJ-MGAWDJABSA-N 0.000 claims 1
- GYLPFOOMKPDYIG-DZOOLQPHSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[3-(4-methylsulfonylphenyl)phenyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CS(=O)(=O)c1ccc(cc1)-c1cccc(c1)-n1cnn(C\C(CN)=C/F)c1=O GYLPFOOMKPDYIG-DZOOLQPHSA-N 0.000 claims 1
- FXYNHNWDLJPNTF-MDZFRNKHSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[5-(1,3-benzodioxol-5-yl)-1,3-thiazol-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ncc(s2)-c2ccc3OCOc3c2)c1=O)=C\F FXYNHNWDLJPNTF-MDZFRNKHSA-N 0.000 claims 1
- QHRLBOGRUUBIMW-WONROIIJSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[5-(2,1,3-benzoxadiazol-5-yl)-1,3-thiazol-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ncc(s2)-c2ccc3nonc3c2)c1=O)=C\F QHRLBOGRUUBIMW-WONROIIJSA-N 0.000 claims 1
- YJPOGJITSXTWKY-MGAWDJABSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[5-(4-methylsulfonylphenyl)pyridin-2-yl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CS(=O)(=O)c1ccc(cc1)-c1ccc(nc1)-n1cnn(C\C(CN)=C/F)c1=O YJPOGJITSXTWKY-MGAWDJABSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims 1
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims 1
- RDOAUPPSCNSYPM-UHFFFAOYSA-N 3,4-dihydropyridine Chemical compound C1CC=NC=C1 RDOAUPPSCNSYPM-UHFFFAOYSA-N 0.000 claims 1
- QSDIXCHNEBIQHJ-UHFFFAOYSA-N 3-methyl-1,2-dihydroimidazole Chemical compound CN1CNC=C1 QSDIXCHNEBIQHJ-UHFFFAOYSA-N 0.000 claims 1
- JJOAUJAKDQYOFM-MDWZMJQESA-N 4-[3-(2-amino-1,3-benzothiazol-5-yl)-2-methylphenyl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one Chemical compound CC1=C(C=CC=C1C1=CC=C2SC(N)=NC2=C1)N1C=NN(C\C(CN)=C\F)C1=O JJOAUJAKDQYOFM-MDWZMJQESA-N 0.000 claims 1
- HDFZHQZEKXGZPK-MXZHIVQLSA-N 4-[3-(2-amino-1,3-benzothiazol-5-yl)phenyl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2cccc(c2)-c2ccc3sc(N)nc3c2)c1=O)=C/F HDFZHQZEKXGZPK-MXZHIVQLSA-N 0.000 claims 1
- OVNXFLRWIYTCLR-FNXZNAJJSA-N 4-[3-(5-acetylthiophen-2-yl)phenyl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CC(=O)c1ccc(s1)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O OVNXFLRWIYTCLR-FNXZNAJJSA-N 0.000 claims 1
- OUDNXZZGMFWJQK-KRWCAOSLSA-N 4-[3-[1-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-5-oxo-1,2,4-triazol-4-yl]phenyl]-N,N-dimethylbenzenesulfonamide hydrochloride Chemical compound Cl.CN(C)S(=O)(=O)c1ccc(cc1)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O OUDNXZZGMFWJQK-KRWCAOSLSA-N 0.000 claims 1
- MLTTVJUNSUIPKG-UGAWPWHASA-N 4-[3-[4-(4-acetylpiperazin-1-yl)phenyl]phenyl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CC(=O)N1CCN(CC1)c1ccc(cc1)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O MLTTVJUNSUIPKG-UGAWPWHASA-N 0.000 claims 1
- AMJUVKXSWAVDEO-YRNVUSSQSA-N 4-[4-(2-amino-1,3-benzothiazol-5-yl)pyridin-2-yl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one Chemical compound NC\C(CN1N=CN(C1=O)C1=NC=CC(=C1)C1=CC=C2SC(N)=NC2=C1)=C/F AMJUVKXSWAVDEO-YRNVUSSQSA-N 0.000 claims 1
- XJAHSGAHYFDRJG-MGAWDJABSA-N 4-[4-(5-acetylthiophen-2-yl)phenyl]-2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.CC(=O)c1ccc(s1)-c1ccc(cc1)-n1cnn(C\C(CN)=C/F)c1=O XJAHSGAHYFDRJG-MGAWDJABSA-N 0.000 claims 1
- MEHNUYXHTVTNTM-OAZHBLANSA-N 4-[5-(2-amino-1,3-benzothiazol-5-yl)-3-fluoropyridin-2-yl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC\C(Cn1ncn(-c2ncc(cc2F)-c2ccc3sc(N)nc3c2)c1=O)=C/F MEHNUYXHTVTNTM-OAZHBLANSA-N 0.000 claims 1
- IATSTAXFCUBZGB-WXIWBVQFSA-N 4-[5-(2-amino-1,3-benzothiazol-5-yl)-4-methylpyridin-2-yl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(ncc1-c1ccc2sc(N)nc2c1)-n1cnn(C\C(CN)=C\F)c1=O IATSTAXFCUBZGB-WXIWBVQFSA-N 0.000 claims 1
- JLDHLHVYSAQNAK-ONNFQVAWSA-N 4-[5-(2-amino-1,3-benzothiazol-5-yl)pyrazin-2-yl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one Chemical compound NC\C(CN1N=CN(C1=O)C1=CN=C(C=N1)C1=CC=C2SC(N)=NC2=C1)=C/F JLDHLHVYSAQNAK-ONNFQVAWSA-N 0.000 claims 1
- PSNVZNYNACPVIK-WUXMJOGZSA-N 4-[6-(2-amino-1,3-benzothiazol-5-yl)-4-methylpyridin-3-yl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one Chemical compound CC1=C(C=NC(=C1)C1=CC=C2SC(N)=NC2=C1)N1C=NN(C\C(CN)=C\F)C1=O PSNVZNYNACPVIK-WUXMJOGZSA-N 0.000 claims 1
- VOMUGMZVTHZLTI-WXIWBVQFSA-N 4-[6-(2-amino-1,3-benzothiazol-5-yl)-5-methylpyridin-3-yl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.Cc1cc(cnc1-c1ccc2sc(N)nc2c1)-n1cnn(C\C(CN)=C\F)c1=O VOMUGMZVTHZLTI-WXIWBVQFSA-N 0.000 claims 1
- WTQKXAPDTWLQIP-YRNVUSSQSA-N 4-[6-(2-amino-1,3-benzothiazol-5-yl)pyridin-2-yl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one Chemical compound NC\C(CN1N=CN(C1=O)C1=NC(=CC=C1)C1=CC=C2SC(N)=NC2=C1)=C/F WTQKXAPDTWLQIP-YRNVUSSQSA-N 0.000 claims 1
- CXACPMQHIHBJOU-XHIXCECLSA-N 5-[3-[1-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-5-oxo-1,2,4-triazol-4-yl]phenyl]-1,3-dimethylpyridin-2-one hydrochloride Chemical compound Cl.Cc1cc(cn(C)c1=O)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O CXACPMQHIHBJOU-XHIXCECLSA-N 0.000 claims 1
- NWKPIXBOOSCWFF-NSPIFIKESA-N 5-[3-[1-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-5-oxo-1,2,4-triazol-4-yl]phenyl]-1-propan-2-ylpyridin-2-one hydrochloride Chemical compound Cl.CC(C)n1cc(ccc1=O)-c1cccc(c1)-n1cnn(C\C(CN)=C\F)c1=O NWKPIXBOOSCWFF-NSPIFIKESA-N 0.000 claims 1
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| KR20200004036A (ko) * | 2018-07-03 | 2020-01-13 | 주식회사유한양행 | (e)-(2-(클로로메틸)-3-플루오로알릴)카바메이트 유도체의 제조방법 |
| 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 |
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Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2725148A1 (de) | 1977-06-03 | 1978-12-14 | Hoechst Ag | 1-aryl-4-alkyl-1,2,4-triazol-5-one und verfahren zu ihrer herstellung |
| US20050096360A1 (en) | 2003-08-08 | 2005-05-05 | Salter-Cid Luisa M. | Inhibitors of semicarbazide-sensitive amine oxidase (SSAO) and VAP-1 mediated adhesion useful for treatment of diseases |
| KR100572996B1 (ko) | 2003-08-12 | 2006-04-25 | 한국화학연구원 | 불소화 비닐 에테르 측쇄기를 갖는 아졸계 살균제 화합물및 그의 제조방법 |
| KR20060135781A (ko) | 2004-02-25 | 2006-12-29 | 라 졸라 파마슈티칼 컴파니 | 질병의 치료를 위한 아민 및 아미드 |
| TW200726765A (en) | 2005-06-17 | 2007-07-16 | Bristol Myers Squibb Co | Triazolopyridine cannabinoid receptor 1 antagonists |
| WO2007120528A2 (en) * | 2006-03-31 | 2007-10-25 | La Jolla Pharmaceutical Company | Inhibitors of semicarbazide-sensitive amine oxidase (ssao) and vap-1 mediated adhesion useful for treatment and prevention of diseases |
| WO2008118414A1 (en) | 2007-03-28 | 2008-10-02 | Merck & Co., Inc. | Substituted pyrido[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine derivatives as cannabinoid-1 receptor modulators |
| BRPI0809617A2 (pt) | 2007-03-29 | 2014-09-16 | Hoffmann La Roche | Inibidores não-nucleosídicos da transcriptase reversa |
| GB0722075D0 (en) | 2007-11-09 | 2007-12-19 | Smithkline Beecham Corp | Compounds |
| JP2011504485A (ja) | 2007-11-21 | 2011-02-10 | ファーマクシス リミテッド | Ｓｓａｏ／ｖａｐ−１のハロアリルアミン阻害剤およびその用途 |
| WO2010096722A1 (en) | 2009-02-20 | 2010-08-26 | Takeda Pharmaceutical Company Limited | 3-oxo-2, 3-dihydro- [1,2, 4] triazolo [4, 3-a]pyridines as soluble epoxide hydrolase (seh) inhibitors |
| WO2013134562A1 (en) * | 2012-03-09 | 2013-09-12 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| US9192617B2 (en) | 2012-03-20 | 2015-11-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| EP3438087A1 (en) | 2012-05-02 | 2019-02-06 | Boehringer Ingelheim International GmbH | Substituted 3-haloallylamine inhibitors of ssao and uses thereof |
| BR112015026631A2 (pt) * | 2013-04-25 | 2017-07-25 | Yuhan Corp | compostos ou sais farmaceuticamente aceitáveis dos mesmos e respectivos usos, composição farmacêutica e método para prevenir ou tratar diabetes melito em mamífero |
| WO2016007727A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| EP3230277B1 (en) | 2014-12-11 | 2019-09-18 | Zenith Epigenetics Ltd. | Substituted heterocycles as bromodomain inhibitors |
| WO2016101119A1 (en) | 2014-12-23 | 2016-06-30 | Merck Sharp & Dohme Corp. | Fused heteroaryl derivatives as orexin receptor antagonists |
| 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 |
| WO2020063854A1 (zh) | 2018-09-27 | 2020-04-02 | 南京明德新药研发有限公司 | 作为vap-1抑制剂的喹啉类衍生物 |
| CN113164454A (zh) | 2018-09-28 | 2021-07-23 | 奥克塞拉有限公司 | Vap-1的抑制剂 |
| MX2021003731A (es) | 2018-09-28 | 2021-08-05 | Acucela Inc | Inhibidores de vap-1. |
| 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 |
-
2018
- 2018-03-21 KR KR1020180032554A patent/KR20190110740A/ko active Pending
-
2019
- 2019-03-20 KR KR1020207029749A patent/KR20200123846A/ko not_active Ceased
- 2019-03-20 CN CN201980020750.6A patent/CN111886227B/zh not_active Expired - Fee Related
- 2019-03-20 EP EP19770858.9A patent/EP3768663A4/en not_active Withdrawn
- 2019-03-20 JP JP2020550099A patent/JP7322052B2/ja active Active
- 2019-03-20 CA CA3093051A patent/CA3093051A1/en active Pending
- 2019-03-20 AU AU2019237342A patent/AU2019237342B2/en not_active Ceased
- 2019-03-20 WO PCT/IB2019/052276 patent/WO2019180644A1/en not_active Ceased
- 2019-03-20 US US16/359,984 patent/US10562865B2/en active Active
- 2019-03-21 AR ARP190100712A patent/AR115006A1/es not_active Application Discontinuation
- 2019-03-21 TW TW108109844A patent/TWI825079B/zh not_active IP Right Cessation
- 2019-12-19 US US16/721,020 patent/US10899719B2/en not_active Expired - Fee Related
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2020
- 2020-11-25 US US17/104,557 patent/US11492335B2/en active Active
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2023
- 2023-07-26 JP JP2023121661A patent/JP2023134824A/ja active Pending
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