KR20190110736A - 신규의 트라이아졸론 유도체 또는 이의 염 및 이를 포함하는 약학 조성물 - Google Patents
신규의 트라이아졸론 유도체 또는 이의 염 및 이를 포함하는 약학 조성물 Download PDFInfo
- Publication number
- KR20190110736A KR20190110736A KR1020180032548A KR20180032548A KR20190110736A KR 20190110736 A KR20190110736 A KR 20190110736A KR 1020180032548 A KR1020180032548 A KR 1020180032548A KR 20180032548 A KR20180032548 A KR 20180032548A KR 20190110736 A KR20190110736 A KR 20190110736A
- Authority
- KR
- South Korea
- Prior art keywords
- triazol
- aminomethyl
- dihydro
- hydrochloride
- methyl
- 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.)
- Pending
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- 150000003839 salts Chemical class 0.000 title claims abstract description 54
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical class O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 28
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 16
- 101710132836 Membrane primary amine oxidase Proteins 0.000 claims abstract description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 258
- 150000001875 compounds Chemical class 0.000 claims description 248
- -1 trifluoroethoxy, 3,5 Dimethoxybenzyloxy, amino Chemical group 0.000 claims description 177
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 156
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 83
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 32
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 32
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 26
- 229920002554 vinyl polymer Polymers 0.000 claims description 25
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 12
- QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 10
- 229930192474 thiophene Natural products 0.000 claims description 10
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 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 description 7
- GZOJTRITAZODJV-UHFFFAOYSA-N 3,1-benzoxazin-2-one Chemical compound C1=CC=CC2=COC(=O)N=C21 GZOJTRITAZODJV-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 102100027159 Membrane primary amine oxidase Human genes 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims description 4
- TVXFVQWXAICAHY-KYIGKLDSSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[3-(dimethylamino)phenyl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC/C(/CN1N=CN(C1=O)CC=1SC(=CC=1)C1=CC(=CC=C1)N(C)C)=C\F TVXFVQWXAICAHY-KYIGKLDSSA-N 0.000 claims description 4
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 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 description 4
- GTFMIJNXNMDHAB-UHFFFAOYSA-N 4h-1,4-benzothiazin-3-one Chemical compound C1=CC=C2NC(=O)CSC2=C1 GTFMIJNXNMDHAB-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 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 description 3
- IKLUNRZWPMVYAZ-YFMOEUEHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(3-piperazin-1-ylphenyl)thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound C1CN(CCN1)C2=CC=CC(=C2)C3=CC=C(S3)CN4C=NN(C4=O)C/C(=C/F)/CN.Cl IKLUNRZWPMVYAZ-YFMOEUEHSA-N 0.000 claims description 3
- WFIIAHWNJKNJQO-YFMOEUEHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(4-piperazin-1-ylphenyl)thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound C1CN(CCN1)C2=CC=C(C=C2)C3=CC=C(S3)CN4C=NN(C4=O)C/C(=C/F)/CN.Cl WFIIAHWNJKNJQO-YFMOEUEHSA-N 0.000 claims description 3
- WDWMKMCUWYNMTC-NTUHNPAUSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[3-(1H-1,2,4-triazol-5-yl)phenyl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)CC=1SC(=CC=1)C1=CC(=CC=C1)C1=NN=CN1)=C\F WDWMKMCUWYNMTC-NTUHNPAUSA-N 0.000 claims description 3
- LQSKQTJWTDUCJQ-NTUHNPAUSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[4-(1H-1,2,4-triazol-5-yl)phenyl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)CC=1SC(=CC=1)C1=CC=C(C=C1)C1=NN=CN1)=C\F LQSKQTJWTDUCJQ-NTUHNPAUSA-N 0.000 claims description 3
- XUHPYJPZEQBGIB-GYVLLFFHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[4-(2-methoxyethoxy)phenyl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound COCCOC1=CC=C(C=C1)C2=CC=C(S2)CN3C=NN(C3=O)C/C(=C/F)/CN.Cl XUHPYJPZEQBGIB-GYVLLFFHSA-N 0.000 claims description 3
- NAURNGZPFZHQRX-KYIGKLDSSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[4-(dimethylamino)phenyl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound CN(C)C1=CC=C(C=C1)C2=CC=C(S2)CN3C=NN(C3=O)C/C(=C/F)/CN.Cl NAURNGZPFZHQRX-KYIGKLDSSA-N 0.000 claims description 3
- JSVQXEHLKVUAFY-YFMOEUEHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[4-(oxan-4-yl)phenyl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound C1COCCC1C2=CC=C(C=C2)C3=CC=C(S3)CN4C=NN(C4=O)C/C(=C/F)/CN.Cl JSVQXEHLKVUAFY-YFMOEUEHSA-N 0.000 claims description 3
- MCHGMLZWEZCLTO-FTPOTTDRSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[6-(dimethylamino)pyridin-3-yl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound CN(C)C1=NC=C(C=C1)C2=CC=C(S2)CN3C=NN(C3=O)C/C(=C/F)/CN.Cl MCHGMLZWEZCLTO-FTPOTTDRSA-N 0.000 claims description 3
- WBMMJLIYZRARLK-BAQGIRSFSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[(5-bromothiophen-2-yl)methyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)CC=1SC(=CC=1)Br)=C/F WBMMJLIYZRARLK-BAQGIRSFSA-N 0.000 claims description 3
- WDWMKMCUWYNMTC-QPEQYQDCSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[3-(1H-1,2,4-triazol-5-yl)phenyl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)CC=1SC(=CC=1)C1=CC(=CC=C1)C1=NN=CN1)=C/F WDWMKMCUWYNMTC-QPEQYQDCSA-N 0.000 claims description 3
- LQSKQTJWTDUCJQ-QPEQYQDCSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[4-(1H-1,2,4-triazol-5-yl)phenyl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one Chemical compound NC/C(/CN1N=CN(C1=O)CC=1SC(=CC=1)C1=CC=C(C=C1)C1=NN=CN1)=C/F LQSKQTJWTDUCJQ-QPEQYQDCSA-N 0.000 claims description 3
- QOYPZTKFHBBPRX-MWVRIADDSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[4-(morpholine-4-carbonyl)phenyl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC/C(/CN1N=CN(C1=O)CC=1SC(=CC=1)C1=CC=C(C=C1)C(=O)N1CCOCC1)=C/F QOYPZTKFHBBPRX-MWVRIADDSA-N 0.000 claims description 3
- OZQIFKTXPBBKJC-JIBDQCPFSA-N 2-[(Z)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[6-(trifluoromethyl)pyridin-3-yl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC/C(/CN1N=CN(C1=O)CC=1SC(=CC1)C=1C=NC(=CC1)C(F)(F)F)=C/F OZQIFKTXPBBKJC-JIBDQCPFSA-N 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical group C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 3
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 3
- JCIPYQWZFWCRTI-XMMWENQYSA-N 4-[[5-[4-(4-acetylpiperazin-1-yl)phenyl]thiophen-2-yl]methyl]-2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-1,2,4-triazol-3-one hydrochloride Chemical compound CC(=O)N1CCN(CC1)C2=CC=C(C=C2)C3=CC=C(S3)CN4C=NN(C4=O)C/C(=C/F)/CN.Cl JCIPYQWZFWCRTI-XMMWENQYSA-N 0.000 claims description 3
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 3
- OENORFKWCZXKCB-KJEVSKRMSA-N Cl.NC/C(/CN1N=C(N(C1=O)C=1SC(=CC1)C1=CC(=C(C=C1)OC)OC)C)=C\F Chemical compound Cl.NC/C(/CN1N=C(N(C1=O)C=1SC(=CC1)C1=CC(=C(C=C1)OC)OC)C)=C\F OENORFKWCZXKCB-KJEVSKRMSA-N 0.000 claims description 3
- VCTZNIHWEJNKLU-RRAJOLSVSA-N methyl 3-[5-[[1-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-5-oxo-1,2,4-triazol-4-yl]methyl]thiophen-2-yl]-5-fluorobenzoate hydrochloride Chemical compound COC(=O)C1=CC(=CC(=C1)C2=CC=C(S2)CN3C=NN(C3=O)C/C(=C/F)/CN)F.Cl VCTZNIHWEJNKLU-RRAJOLSVSA-N 0.000 claims description 3
- GYQDNZLMOLJYSH-RRAJOLSVSA-N methyl 4-[5-[[1-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-5-oxo-1,2,4-triazol-4-yl]methyl]thiophen-2-yl]-2-fluorobenzoate hydrochloride Chemical compound Cl.COC(=O)c1ccc(cc1F)-c1ccc(Cn2cnn(C\C(CN)=C\F)c2=O)s1 GYQDNZLMOLJYSH-RRAJOLSVSA-N 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- AQWOIRBQLOOZGX-UHFFFAOYSA-N triazolo[1,5-a]pyridine Chemical compound C1=CC=CC2=CN=NN21 AQWOIRBQLOOZGX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- ZCZVGQCBSJLDDS-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridine Chemical compound C1=CC=C2CCCNC2=N1 ZCZVGQCBSJLDDS-UHFFFAOYSA-N 0.000 claims description 2
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 claims description 2
- XXBQLHATYQHJQC-UHFFFAOYSA-N 1,2-dihydroquinoxaline Chemical compound C1=CC=C2N=CCNC2=C1 XXBQLHATYQHJQC-UHFFFAOYSA-N 0.000 claims description 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- MENHXVNCWVKFRA-UHFFFAOYSA-N 1,4-oxazin-2-one Chemical compound O=C1C=NC=CO1 MENHXVNCWVKFRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- JBYNDDWUEAYKSE-SODSUQDMSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(2-methylsulfanylpyrimidin-5-yl)thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC/C(/CN1N=CN(C1=O)CC=1SC(=CC1)C=1C=NC(=NC1)SC)=C\F JBYNDDWUEAYKSE-SODSUQDMSA-N 0.000 claims description 2
- ZWNBHZHIZIHONA-FJUODKGNSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(2-morpholin-4-ylpyrimidin-5-yl)thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC/C(/CN1N=CN(C1=O)CC=1SC(=CC1)C=1C=NC(=NC1)N1CCOCC1)=C\F ZWNBHZHIZIHONA-FJUODKGNSA-N 0.000 claims description 2
- DDKKFMIVBFDVFD-YFMOEUEHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(3-pyrrolidin-1-ylsulfonylphenyl)thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC/C(/CN1N=CN(C1=O)CC=1SC(=CC1)C1=CC(=CC=C1)S(=O)(=O)N1CCCC1)=C\F DDKKFMIVBFDVFD-YFMOEUEHSA-N 0.000 claims description 2
- LTBPJFXEMMTUTJ-QFHYWFJHSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-(6-piperidin-1-ylpyridin-3-yl)thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound C1CCN(CC1)C2=NC=C(C=C2)C3=CC=C(S3)CN4C=NN(C4=O)C/C(=C/F)/CN.Cl LTBPJFXEMMTUTJ-QFHYWFJHSA-N 0.000 claims description 2
- WKBPKGQKMQEYKZ-JSSTZBRYSA-N 2-[(E)-2-(aminomethyl)-3-fluoroprop-2-enyl]-4-[[5-[2-(1-methylpyrazol-4-yl)ethynyl]thiophen-2-yl]methyl]-1,2,4-triazol-3-one hydrochloride Chemical compound Cl.NC/C(/CN1N=CN(C1=O)CC=1SC(=CC1)C#CC=1C=NN(C1)C)=C\F WKBPKGQKMQEYKZ-JSSTZBRYSA-N 0.000 claims description 2
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 210000003556 vascular endothelial cell Anatomy 0.000 description 1
- 210000000264 venule Anatomy 0.000 description 1
- 239000002676 xenobiotic agent Substances 0.000 description 1
- 230000002034 xenobiotic effect Effects 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| EP19772403.2A EP3768675B1 (en) | 2018-03-21 | 2019-03-20 | Novel triazolone derivatives or salts thereof and pharmaceutical compositions comprising the same |
| KR1020207029750A KR102788118B1 (ko) | 2018-03-21 | 2019-03-20 | 신규한 트리아졸론 유도체 또는 그의 염, 및 그를 포함하는 제약 조성물 |
| JP2020550176A JP7383627B2 (ja) | 2018-03-21 | 2019-03-20 | 新規トリアゾロン誘導体またはその塩、およびこれらを含む医薬組成物 |
| CA3093057A CA3093057A1 (en) | 2018-03-21 | 2019-03-20 | Novel triazolone derivatives or salts thereof and pharmaceutical compositions comprising the same |
| CN201980020696.5A CN111886233B (zh) | 2018-03-21 | 2019-03-20 | 三唑酮衍生物或其盐以及包含其的药物组合物 |
| US16/359,985 US10995086B2 (en) | 2018-03-21 | 2019-03-20 | Triazolone derivatives or salts thereof and pharmaceutical compositions comprising the same |
| PCT/IB2019/052278 WO2019180646A1 (en) | 2018-03-21 | 2019-03-20 | Novel triazolone derivatives or salts thereof and pharmaceutical compositions comprising the same |
| AU2019237344A AU2019237344B2 (en) | 2018-03-21 | 2019-03-20 | Novel triazolone derivatives or salts thereof and pharmaceutical compositions comprising the same |
| TW108109864A TWI803600B (zh) | 2018-03-21 | 2019-03-21 | 新穎的三唑酮衍生物或其鹽及包含彼等之醫藥組合物 |
| ARP190100713A AR115007A1 (es) | 2018-03-21 | 2019-03-21 | Derivados de triazolona o sales de los mismos y composiciones farmacéuticas que comprenden los mismos |
| US17/208,887 US11780830B2 (en) | 2018-03-21 | 2021-03-22 | Triazolone derivatives or salts thereof and pharmaceutical compositions comprising the same |
| JP2023128580A JP2023145748A (ja) | 2018-03-21 | 2023-08-07 | 新規トリアゾロン誘導体またはその塩、およびこれらを含む医薬組成物 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2022224195A1 (en) * | 2021-04-22 | 2022-10-27 | Yuhan Corporation | Triazolones, tetrazolones, and imidazolones, or their salts, and pharmaceutical compositions comprising the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| 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 |
| 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 |
| BR112021013429A2 (pt) | 2019-01-11 | 2021-10-19 | Nanjing Transthera Biosciences Co., Ltd. | Composto, composição farmacêutica, e, uso do composto |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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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2019
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2023
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022224195A1 (en) * | 2021-04-22 | 2022-10-27 | Yuhan Corporation | Triazolones, tetrazolones, and imidazolones, or their salts, and pharmaceutical compositions comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2023145748A (ja) | 2023-10-11 |
| CN111886233B (zh) | 2024-01-02 |
| JP7383627B2 (ja) | 2023-11-20 |
| EP3768675B1 (en) | 2026-04-01 |
| WO2019180646A1 (en) | 2019-09-26 |
| EP3768675A4 (en) | 2021-12-22 |
| AU2019237344B2 (en) | 2023-07-06 |
| US10995086B2 (en) | 2021-05-04 |
| US20190322655A1 (en) | 2019-10-24 |
| KR20200124759A (ko) | 2020-11-03 |
| AR115007A1 (es) | 2020-11-18 |
| CA3093057A1 (en) | 2019-09-26 |
| TW202003508A (zh) | 2020-01-16 |
| CN111886233A (zh) | 2020-11-03 |
| EP3768675A1 (en) | 2021-01-27 |
| KR102788118B1 (ko) | 2025-03-31 |
| TWI803600B (zh) | 2023-06-01 |
| US11780830B2 (en) | 2023-10-10 |
| AU2019237344A1 (en) | 2020-10-01 |
| JP2021518384A (ja) | 2021-08-02 |
| US20210317110A1 (en) | 2021-10-14 |
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