JP2018522046A5 - - Google Patents
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- Publication number
- JP2018522046A5 JP2018522046A5 JP2018505695A JP2018505695A JP2018522046A5 JP 2018522046 A5 JP2018522046 A5 JP 2018522046A5 JP 2018505695 A JP2018505695 A JP 2018505695A JP 2018505695 A JP2018505695 A JP 2018505695A JP 2018522046 A5 JP2018522046 A5 JP 2018522046A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- substituted
- phenyl
- triazol
- oxopyrimidin
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 106
- 125000000623 heterocyclic group Chemical group 0.000 claims 75
- 229910052799 carbon Inorganic materials 0.000 claims 66
- 229910052739 hydrogen Inorganic materials 0.000 claims 62
- -1 substituted Chemical class 0.000 claims 53
- 125000004452 carbocyclyl group Chemical group 0.000 claims 36
- 229910052801 chlorine Inorganic materials 0.000 claims 36
- 229910052731 fluorine Inorganic materials 0.000 claims 36
- 229910052736 halogen Inorganic materials 0.000 claims 36
- 150000002367 halogens Chemical class 0.000 claims 36
- 229910052794 bromium Inorganic materials 0.000 claims 30
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 25
- 229910052760 oxygen Inorganic materials 0.000 claims 22
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 18
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical group FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 16
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 239000005711 Benzoic acid Substances 0.000 claims 7
- 235000010233 benzoic acid Nutrition 0.000 claims 7
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 5
- 230000009424 thromboembolic effect Effects 0.000 claims 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- BVNIREPGHLFKNZ-UHFFFAOYSA-N n-methylcyclopropanecarboxamide Chemical compound CNC(=O)C1CC1 BVNIREPGHLFKNZ-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- NXERLUTWYXJQPD-VWLOTQADSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenyl-N-[(3-propan-2-yl-1,2-oxazol-5-yl)methyl]propanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NCC1=CC(=NO1)C(C)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl NXERLUTWYXJQPD-VWLOTQADSA-N 0.000 claims 1
- CSBZSKMQSZCXAP-NRFANRHFSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenyl-N-[2-(1H-1,2,4-triazol-5-yl)ethyl]propanamide Chemical compound N1N=CN=C1CCNC([C@H](CC1=CC=CC=C1)N1C=NC(=CC1=O)C1=C(C=CC(=C1)Cl)N1N=NC(=C1)Cl)=O CSBZSKMQSZCXAP-NRFANRHFSA-N 0.000 claims 1
- SGGWHGAKELRTAJ-NRFANRHFSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenyl-N-propylpropanamide Chemical compound CCCNC(=O)[C@H](CC1=CC=CC=C1)N1C=NC(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(Cl)N=N1 SGGWHGAKELRTAJ-NRFANRHFSA-N 0.000 claims 1
- LJMWBHQTEHWPLC-DEOSSOPVSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N,3-diphenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=CC=CC=C1)CC1=CC=CC=C1)N1N=NC(=C1)Cl LJMWBHQTEHWPLC-DEOSSOPVSA-N 0.000 claims 1
- UTLJRHNHDYVJSO-FQEVSTJZSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(1-methyltriazol-4-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1N=NN(C=1)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl UTLJRHNHDYVJSO-FQEVSTJZSA-N 0.000 claims 1
- LCPQDFNPFHVSSF-SANMLTNESA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(1-oxo-2H-isoquinolin-6-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1C=C2C=CNC(C2=CC=1)=O)CC1=CC=CC=C1)N1N=NC(=C1)Cl LCPQDFNPFHVSSF-SANMLTNESA-N 0.000 claims 1
- DNOOIIBEGSANSQ-SANMLTNESA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(1-oxo-3,4-dihydro-2H-isoquinolin-6-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1C=C2CCNC(C2=CC=1)=O)CC1=CC=CC=C1)N1N=NC(=C1)Cl DNOOIIBEGSANSQ-SANMLTNESA-N 0.000 claims 1
- KEIALZBYKNJFPP-DEOSSOPVSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(1H-indazol-3-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=NNC2=CC=CC=C12)CC1=CC=CC=C1)N1N=NC(=C1)Cl KEIALZBYKNJFPP-DEOSSOPVSA-N 0.000 claims 1
- JSTWHMSWKCBCGP-VWLOTQADSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(1H-indazol-6-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=CC=C2C=NNC2=C1)CC1=CC=CC=C1)N1N=NC(=C1)Cl JSTWHMSWKCBCGP-VWLOTQADSA-N 0.000 claims 1
- UTYKEDLGMGIUAB-SANMLTNESA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(1H-indol-4-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=C2C=CNC2=CC=C1)CC1=CC=CC=C1)N1N=NC(=C1)Cl UTYKEDLGMGIUAB-SANMLTNESA-N 0.000 claims 1
- KVUXITIYMWLAEE-QFIPXVFZSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(2,2-dimethyl-3-oxo-4H-pyrido[3,2-b][1,4]oxazin-6-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1C=CC=2OC(C(NC=2N=1)=O)(C)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl KVUXITIYMWLAEE-QFIPXVFZSA-N 0.000 claims 1
- LUMNENKHPXENSR-YNMFNDETSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(2,3-dihydro-1-benzofuran-3-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1COC2=C1C=CC=C2)CC1=CC=CC=C1)N1N=NC(=C1)Cl LUMNENKHPXENSR-YNMFNDETSA-N 0.000 claims 1
- CHVVWEMCFKBNGU-WKDCXCOVSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(2,3-dihydro-1H-inden-1-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1CCC2=CC=CC=C12)CC1=CC=CC=C1)N1N=NC(=C1)Cl CHVVWEMCFKBNGU-WKDCXCOVSA-N 0.000 claims 1
- DVOMCITUKHLEAH-QHCPKHFHSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(2-ethyl-5-methylpyrazol-3-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=CC(=NN1CC)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl DVOMCITUKHLEAH-QHCPKHFHSA-N 0.000 claims 1
- RZMLVXWPDMIYPL-FQEVSTJZSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(2-hydroxyethyl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NCCO)CC1=CC=CC=C1)N1N=NC(=C1)Cl RZMLVXWPDMIYPL-FQEVSTJZSA-N 0.000 claims 1
- KICFASXCSNWFOG-NRFANRHFSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(2-methoxyethyl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NCCOC)CC1=CC=CC=C1)N1N=NC(=C1)Cl KICFASXCSNWFOG-NRFANRHFSA-N 0.000 claims 1
- IQPIMEZLRZTMCJ-QFIPXVFZSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(2-methoxyethyl)-N-methyl-3-phenylpropanamide Chemical compound COCCN(C)C(=O)[C@H](CC1=CC=CC=C1)N1C=NC(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(Cl)N=N1 IQPIMEZLRZTMCJ-QFIPXVFZSA-N 0.000 claims 1
- HOFIXSKDZBPEEH-VWLOTQADSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(2-methyl-1,3-benzoxazol-6-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=CC2=C(N=C(O2)C)C=C1)CC1=CC=CC=C1)N1N=NC(=C1)Cl HOFIXSKDZBPEEH-VWLOTQADSA-N 0.000 claims 1
- SNPUONCEDOBCBY-VWLOTQADSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(2-oxo-1,3-dihydroindol-5-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1C=C2CC(NC2=CC=1)=O)CC1=CC=CC=C1)N1N=NC(=C1)Cl SNPUONCEDOBCBY-VWLOTQADSA-N 0.000 claims 1
- YILDMAHMRNNPEL-QHCPKHFHSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(3-methylbutyl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NCCC(C)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl YILDMAHMRNNPEL-QHCPKHFHSA-N 0.000 claims 1
- BIMYSLYQEQZUMU-DEOSSOPVSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(3-methylimidazo[4,5-b]pyridin-6-yl)-3-phenylpropanamide Chemical compound Cn1cnc2cc(NC(=O)[C@H](Cc3ccccc3)n3cnc(cc3=O)-c3cc(Cl)ccc3-n3cc(Cl)nn3)cnc12 BIMYSLYQEQZUMU-DEOSSOPVSA-N 0.000 claims 1
- RKQCUABJCVNEPR-VWLOTQADSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(3-oxo-1,2-dihydroisoindol-5-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1C=C2C(NCC2=CC=1)=O)CC1=CC=CC=C1)N1N=NC(=C1)Cl RKQCUABJCVNEPR-VWLOTQADSA-N 0.000 claims 1
- JJSKORKLDKWXFN-VWLOTQADSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(4-cyano-3-fluorophenyl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=CC(=C(C=C1)C#N)F)CC1=CC=CC=C1)N1N=NC(=C1)Cl JJSKORKLDKWXFN-VWLOTQADSA-N 0.000 claims 1
- PRTZHJYVCCRYQX-IMQCZEGASA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(4-hydroxycyclohexyl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1CCC(CC1)O)CC1=CC=CC=C1)N1N=NC(=C1)Cl PRTZHJYVCCRYQX-IMQCZEGASA-N 0.000 claims 1
- UOCVVWYEHOQVEQ-QFIPXVFZSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(5-cyclobutyl-1H-1,2,4-triazol-3-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=NN=C(N1)C1CCC1)CC1=CC=CC=C1)N1N=NC(=C1)Cl UOCVVWYEHOQVEQ-QFIPXVFZSA-N 0.000 claims 1
- QAEKGQRIHDQNGG-NRFANRHFSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(5-methyl-6H-1,3,4-thiadiazin-2-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1SCC(=NN=1)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl QAEKGQRIHDQNGG-NRFANRHFSA-N 0.000 claims 1
- KUJFPOBHISVWJM-MHZLTWQESA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(6-chloroquinolin-4-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=CC=NC2=CC=C(C=C12)Cl)CC1=CC=CC=C1)N1N=NC(=C1)Cl KUJFPOBHISVWJM-MHZLTWQESA-N 0.000 claims 1
- RATQSILLPWNWLK-DEOSSOPVSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(6-cyanopyridin-3-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1C=NC(=CC=1)C#N)CC1=CC=CC=C1)N1N=NC(=C1)Cl RATQSILLPWNWLK-DEOSSOPVSA-N 0.000 claims 1
- IEXRDHPVSNQERC-VWLOTQADSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(6-fluoro-3-oxo-1,2-dihydroisoindol-5-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1C=C2C(NCC2=CC=1F)=O)CC1=CC=CC=C1)N1N=NC(=C1)Cl IEXRDHPVSNQERC-VWLOTQADSA-N 0.000 claims 1
- LXPHUYVGWZTIQI-DEOSSOPVSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(6-methyl-1,2-benzoxazol-3-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=NOC2=C1C=CC(=C2)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl LXPHUYVGWZTIQI-DEOSSOPVSA-N 0.000 claims 1
- ZWYVUYFTRVZRGJ-QFIPXVFZSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-(6-methylpyridazin-3-yl)-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1N=NC(=CC=1)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl ZWYVUYFTRVZRGJ-QFIPXVFZSA-N 0.000 claims 1
- XVGJUKGNLGDHGX-MHZLTWQESA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[(1-methylindazol-5-yl)methyl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NCC=1C=C2C=NN(C2=CC=1)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl XVGJUKGNLGDHGX-MHZLTWQESA-N 0.000 claims 1
- BKZSOHBAWGYLTM-QHCPKHFHSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[(1-methylpyrazol-3-yl)methyl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NCC1=NN(C=C1)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl BKZSOHBAWGYLTM-QHCPKHFHSA-N 0.000 claims 1
- JTTUFNWHYADWQI-WIIYFNMSSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[(1-methylpyrrolidin-3-yl)methyl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NCC1CN(CC1)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl JTTUFNWHYADWQI-WIIYFNMSSA-N 0.000 claims 1
- VGHFGIGIKHMEOQ-MHZLTWQESA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[(2-methyl-3H-benzimidazol-5-yl)methyl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NCC=1C=CC2=C(NC(=N2)C)C=1)CC1=CC=CC=C1)N1N=NC(=C1)Cl VGHFGIGIKHMEOQ-MHZLTWQESA-N 0.000 claims 1
- BZNQXVZVUHTIER-RXVVDRJESA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[(3S)-2-oxooxolan-3-yl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)N[C@@H]1C(OCC1)=O)CC1=CC=CC=C1)N1N=NC(=C1)Cl BZNQXVZVUHTIER-RXVVDRJESA-N 0.000 claims 1
- JIHRUQILRDXGAN-SANMLTNESA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[(4-methoxyphenyl)methyl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NCC1=CC=C(C=C1)OC)CC1=CC=CC=C1)N1N=NC(=C1)Cl JIHRUQILRDXGAN-SANMLTNESA-N 0.000 claims 1
- OFLLHWPQTRVPKJ-MHZLTWQESA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[1-(4-chlorophenyl)pyrazol-4-yl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1C=NN(C=1)C1=CC=C(C=C1)Cl)CC1=CC=CC=C1)N1N=NC(=C1)Cl OFLLHWPQTRVPKJ-MHZLTWQESA-N 0.000 claims 1
- RUVJMKIPJVXASC-VWLOTQADSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[1-(cyclopentylmethyl)-1,2,4-triazol-3-yl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=NN(C=N1)CC1CCCC1)CC1=CC=CC=C1)N1N=NC(=C1)Cl RUVJMKIPJVXASC-VWLOTQADSA-N 0.000 claims 1
- PZVYCGOKNSULOG-QHCPKHFHSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[3-(dimethylamino)propyl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NCCCN(C)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl PZVYCGOKNSULOG-QHCPKHFHSA-N 0.000 claims 1
- SNTPMCVQVNBFEF-NDEPHWFRSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[4-(2-methylimidazol-1-yl)phenyl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=CC=C(C=C1)N1C(=NC=C1)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl SNTPMCVQVNBFEF-NDEPHWFRSA-N 0.000 claims 1
- ASNOFIZZDHWDKZ-MHZLTWQESA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[4-(3-oxomorpholin-4-yl)phenyl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=CC=C(C=C1)N1C(COCC1)=O)CC1=CC=CC=C1)N1N=NC(=C1)Cl ASNOFIZZDHWDKZ-MHZLTWQESA-N 0.000 claims 1
- WCEQNBQIWJXEDU-LJAQVGFWSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[4-[2-[(dimethylamino)methyl]imidazol-1-yl]-2-fluorophenyl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=C(C=C(C=C1)N1C(=NC=C1)CN(C)C)F)CC1=CC=CC=C1)N1N=NC(=C1)Cl WCEQNBQIWJXEDU-LJAQVGFWSA-N 0.000 claims 1
- BSVKNQOVAMJJJD-VWLOTQADSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-[6-(3-methyl-1,2,4-triazol-1-yl)pyridin-3-yl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1C=NC(=CC=1)N1N=C(N=C1)C)CC1=CC=CC=C1)N1N=NC(=C1)Cl BSVKNQOVAMJJJD-VWLOTQADSA-N 0.000 claims 1
- JOYAXZQVRPJABR-DEOSSOPVSA-N (2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-N-cyclohexyl-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1CCCCC1)CC1=CC=CC=C1)N1N=NC(=C1)Cl JOYAXZQVRPJABR-DEOSSOPVSA-N 0.000 claims 1
- MEZJSIPEIFCHEV-QHCPKHFHSA-N (2S)-N-(1,2-benzoxazol-3-yl)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanamide Chemical compound O1N=C(C2=C1C=CC=C2)NC([C@H](CC1=CC=CC=C1)N1C=NC(=CC1=O)C1=C(C=CC(=C1)Cl)N1N=NC(=C1)Cl)=O MEZJSIPEIFCHEV-QHCPKHFHSA-N 0.000 claims 1
- GNOLGOXHZRGALA-QHCPKHFHSA-N (2S)-N-(1,3-benzodioxol-5-yl)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanamide Chemical compound O1COC2=C1C=CC(=C2)NC([C@H](CC1=CC=CC=C1)N1C=NC(=CC1=O)C1=C(C=CC(=C1)Cl)N1N=NC(=C1)Cl)=O GNOLGOXHZRGALA-QHCPKHFHSA-N 0.000 claims 1
- HJCCOODYMBPDKS-IBGZPJMESA-N (2S)-N-(2-amino-2-oxoethyl)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanamide Chemical compound NC(CNC([C@H](CC1=CC=CC=C1)N1C=NC(=CC1=O)C1=C(C=CC(=C1)Cl)N1N=NC(=C1)Cl)=O)=O HJCCOODYMBPDKS-IBGZPJMESA-N 0.000 claims 1
- CKWAJMISUCXQQJ-FQEVSTJZSA-N (2S)-N-(3-amino-3-oxopropyl)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanamide Chemical compound NC(CCNC([C@H](CC1=CC=CC=C1)N1C=NC(=CC1=O)C1=C(C=CC(=C1)Cl)N1N=NC(=C1)Cl)=O)=O CKWAJMISUCXQQJ-FQEVSTJZSA-N 0.000 claims 1
- VKKDOARQEHGRNN-DEOSSOPVSA-N (2S)-N-(4-carbamimidoylphenyl)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanamide Chemical compound C(N)(=N)C1=CC=C(C=C1)NC([C@H](CC1=CC=CC=C1)N1C=NC(=CC1=O)C1=C(C=CC(=C1)Cl)N1N=NC(=C1)Cl)=O VKKDOARQEHGRNN-DEOSSOPVSA-N 0.000 claims 1
- XFOGMVSPNTVGCF-QHCPKHFHSA-N (2S)-N-(7-chloro-1,2-benzoxazol-3-yl)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC1=NOC2=C1C=CC=C2Cl)CC1=CC=CC=C1)N1N=NC(=C1)Cl XFOGMVSPNTVGCF-QHCPKHFHSA-N 0.000 claims 1
- ATNCKMVZTVHXNI-VWLOTQADSA-N (2S)-N-benzyl-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanamide Chemical compound C(C1=CC=CC=C1)NC([C@H](CC1=CC=CC=C1)N1C=NC(=CC1=O)C1=C(C=CC(=C1)Cl)N1N=NC(=C1)Cl)=O ATNCKMVZTVHXNI-VWLOTQADSA-N 0.000 claims 1
- GGRMBIKQXRRVAU-QFIPXVFZSA-N 1-[(2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanoyl]-1,4-diazepan-5-one Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)N1CCNC(CC1)=O)CC1=CC=CC=C1)N1N=NC(=C1)Cl GGRMBIKQXRRVAU-QFIPXVFZSA-N 0.000 claims 1
- XIVCTZXRSYNICH-QFIPXVFZSA-N 2-[4-[[(2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanoyl]amino]pyrazol-1-yl]acetic acid Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1C=NN(C=1)CC(=O)O)CC1=CC=CC=C1)N1N=NC(=C1)Cl XIVCTZXRSYNICH-QFIPXVFZSA-N 0.000 claims 1
- BQBREPDQCJOBIF-DEOSSOPVSA-N 3-[(2S)-1-(4-acetylpiperazin-1-yl)-1-oxo-3-phenylpropan-2-yl]-6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]pyrimidin-4-one Chemical compound C(C)(=O)N1CCN(CC1)C([C@H](CC1=CC=CC=C1)N1C=NC(=CC1=O)C1=C(C=CC(=C1)Cl)N1N=NC(=C1)Cl)=O BQBREPDQCJOBIF-DEOSSOPVSA-N 0.000 claims 1
- ORHSXQCAJPKBCF-MHZLTWQESA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-(3,4-dihydro-1H-isoquinolin-2-yl)-1-oxo-3-phenylpropan-2-yl]pyrimidin-4-one Chemical compound ClC=1C=CC(=C(C=1)C1=CC(N(C=N1)[C@H](C(=O)N1CC2=CC=CC=C2CC1)CC1=CC=CC=C1)=O)N1N=NC(=C1)Cl ORHSXQCAJPKBCF-MHZLTWQESA-N 0.000 claims 1
- MZZHKIQLYHIWIM-QHCPKHFHSA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-(4-hydroxypiperidin-1-yl)-1-oxo-3-phenylpropan-2-yl]pyrimidin-4-one Chemical compound ClC=1C=CC(=C(C=1)C1=CC(N(C=N1)[C@H](C(=O)N1CCC(CC1)O)CC1=CC=CC=C1)=O)N1N=NC(=C1)Cl MZZHKIQLYHIWIM-QHCPKHFHSA-N 0.000 claims 1
- DETMDQAGMSPQRV-QHCPKHFHSA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-(4-methylpiperazin-1-yl)-1-oxo-3-phenylpropan-2-yl]pyrimidin-4-one Chemical compound ClC=1C=CC(=C(C=1)C1=CC(N(C=N1)[C@H](C(=O)N1CCN(CC1)C)CC1=CC=CC=C1)=O)N1N=NC(=C1)Cl DETMDQAGMSPQRV-QHCPKHFHSA-N 0.000 claims 1
- VMCWKRGUHTXGOL-VWLOTQADSA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-[4-(1-methylimidazol-2-yl)piperazin-1-yl]-1-oxo-3-phenylpropan-2-yl]pyrimidin-4-one Chemical compound ClC=1C=CC(=C(C=1)C1=CC(N(C=N1)[C@H](C(=O)N1CCN(CC1)C=1N(C=CN=1)C)CC1=CC=CC=C1)=O)N1N=NC(=C1)Cl VMCWKRGUHTXGOL-VWLOTQADSA-N 0.000 claims 1
- UZUXGFFUWKYBDB-PVCWFJFTSA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-[4-(2-hydroxy-5-oxopyrrolidin-1-yl)piperidin-1-yl]-1-oxo-3-phenylpropan-2-yl]pyrimidin-4-one Chemical compound ClC=1C=CC(=C(C=1)C1=CC(N(C=N1)[C@H](C(=O)N1CCC(CC1)N1C(CCC1=O)O)CC1=CC=CC=C1)=O)N1N=NC(=C1)Cl UZUXGFFUWKYBDB-PVCWFJFTSA-N 0.000 claims 1
- HPMHZCLFIXVMSN-VWLOTQADSA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-[4-(dimethylamino)piperidin-1-yl]-1-oxo-3-phenylpropan-2-yl]pyrimidin-4-one Chemical compound ClC=1C=CC(=C(C=1)C1=CC(N(C=N1)[C@H](C(=O)N1CCC(CC1)N(C)C)CC1=CC=CC=C1)=O)N1N=NC(=C1)Cl HPMHZCLFIXVMSN-VWLOTQADSA-N 0.000 claims 1
- FXRYXILRRLUALX-DEOSSOPVSA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-[4-(hydroxymethyl)piperidin-1-yl]-1-oxo-3-phenylpropan-2-yl]pyrimidin-4-one Chemical compound ClC=1C=CC(=C(C=1)C1=CC(N(C=N1)[C@H](C(=O)N1CCC(CC1)CO)CC1=CC=CC=C1)=O)N1N=NC(=C1)Cl FXRYXILRRLUALX-DEOSSOPVSA-N 0.000 claims 1
- CPXCCIGMILROQW-QFIPXVFZSA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-morpholin-4-yl-1-oxo-3-phenylpropan-2-yl]pyrimidin-4-one Chemical compound ClC=1C=CC(=C(C=1)C1=CC(N(C=N1)[C@H](C(=O)N1CCOCC1)CC1=CC=CC=C1)=O)N1N=NC(=C1)Cl CPXCCIGMILROQW-QFIPXVFZSA-N 0.000 claims 1
- OXIPPJCEVYNTRK-NRFANRHFSA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-oxo-1-(3-oxopiperazin-1-yl)-3-phenylpropan-2-yl]pyrimidin-4-one Chemical compound ClC=1C=CC(=C(C=1)C1=CC(N(C=N1)[C@H](C(N1CC(NCC1)=O)=O)CC1=CC=CC=C1)=O)N1N=NC(=C1)Cl OXIPPJCEVYNTRK-NRFANRHFSA-N 0.000 claims 1
- GHCZFILVLOZLJX-DEOSSOPVSA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-oxo-3-phenyl-1-(3-propan-2-yl-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)propan-2-yl]pyrimidin-4-one Chemical compound CC(C)C1=NN=C2CN(CCN12)C(=O)[C@H](CC1=CC=CC=C1)N1C=NC(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(Cl)N=N1 GHCZFILVLOZLJX-DEOSSOPVSA-N 0.000 claims 1
- HQXAZIAJPIKYEO-LJAQVGFWSA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-oxo-3-phenyl-1-(4-phenylpiperidin-1-yl)propan-2-yl]pyrimidin-4-one Chemical compound ClC=1C=CC(=C(C=1)C1=CC(N(C=N1)[C@H](C(N1CCC(CC1)C1=CC=CC=C1)=O)CC1=CC=CC=C1)=O)N1N=NC(=C1)Cl HQXAZIAJPIKYEO-LJAQVGFWSA-N 0.000 claims 1
- VPAUYZHHKWINEF-MHZLTWQESA-N 6-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-3-[(2S)-1-oxo-3-phenyl-1-(4-pyridin-4-ylpiperazin-1-yl)propan-2-yl]pyrimidin-4-one Chemical compound ClC=1C=CC(=C(C=1)C1=CC(N(C=N1)[C@H](C(N1CCN(CC1)C1=CC=NC=C1)=O)CC1=CC=CC=C1)=O)N1N=NC(=C1)Cl VPAUYZHHKWINEF-MHZLTWQESA-N 0.000 claims 1
- LTYBKMUNWBJWSF-SUHMBNCMSA-N 9-[(2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanoyl]-2-methyl-2,9-diazaspiro[4.5]decan-1-one Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)N1CC2(CCN(C2=O)C)CCC1)CC1=CC=CC=C1)N1N=NC(=C1)Cl LTYBKMUNWBJWSF-SUHMBNCMSA-N 0.000 claims 1
- JMJJYDQIZMSBNX-VWLOTQADSA-N N-[1-[(2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanoyl]piperidin-4-yl]acetamide Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)N1CCC(CC1)NC(C)=O)CC1=CC=CC=C1)N1N=NC(=C1)Cl JMJJYDQIZMSBNX-VWLOTQADSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 1
- 210000005242 cardiac chamber Anatomy 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- LFHGKLGCOFBGBR-VWLOTQADSA-N ethyl 7-[(2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanoyl]-6,8-dihydro-5H-imidazo[1,2-a]pyrazine-2-carboxylate Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)N1CC=2N(CC1)C=C(N=2)C(=O)OCC)CC1=CC=CC=C1)N1N=NC(=C1)Cl LFHGKLGCOFBGBR-VWLOTQADSA-N 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- GMBGXJJHGZLQJV-QHCPKHFHSA-N methyl 4-[[(2S)-2-[4-[5-chloro-2-(4-chlorotriazol-1-yl)phenyl]-6-oxopyrimidin-1-yl]-3-phenylpropanoyl]amino]-1-methylpyrrole-2-carboxylate Chemical compound ClC=1C=CC(=C(C=1)C=1N=CN(C(C=1)=O)[C@H](C(=O)NC=1C=C(N(C=1)C)C(=O)OC)CC1=CC=CC=C1)N1N=NC(=C1)Cl GMBGXJJHGZLQJV-QHCPKHFHSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 230000003836 peripheral circulation Effects 0.000 claims 1
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| US10160750B2 (en) | 2015-06-19 | 2018-12-25 | Bristol-Myers Squibb Company | Diamide macrocycles as factor XIa inhibitors |
| JO3703B1 (ar) * | 2015-07-09 | 2021-01-31 | Bayer Pharma AG | مشتقات أوكسوبيريدين مستبدلة |
| CN107849026B (zh) | 2015-07-29 | 2021-01-01 | 百时美施贵宝公司 | 携带烷基或环烷基p2′部分的因子xia大环抑制剂 |
| KR102729666B1 (ko) | 2015-07-29 | 2024-11-12 | 브리스톨-마이어스 스큅 컴퍼니 | 비-방향족 P2' 기를 갖는 인자 XIa 신규 마크로사이클 |
| EP3331872B1 (en) | 2015-08-05 | 2019-09-25 | Bristol-Myers Squibb Company | Novel substituted glycine derived fxia inhibitors |
| JP7112715B2 (ja) * | 2018-03-23 | 2022-08-04 | 株式会社Kyulux | 有機発光素子材料合成用原料および化合物 |
| CN112004810B (zh) | 2018-07-02 | 2022-04-08 | 江苏恒瑞医药股份有限公司 | 一种氧代吡啶酰胺类衍生物的晶型及制备方法 |
| US20210292279A1 (en) * | 2018-07-19 | 2021-09-23 | Jiangsu Hengrui Medicine Co., Ltd. | Method for preparing coagulation factor xia inhibitor and intermediate thereof |
| CA3123324A1 (en) * | 2018-12-17 | 2020-06-25 | Bayer Aktiengesellschaft | Substituted oxopyridine derivatives for the treatment and/or prophylaxis of thrombotic or thromboembolic disorders and/or thrombotic or thromboembolic complications |
| CN112047931B (zh) * | 2019-06-06 | 2024-03-08 | 上海美悦生物科技发展有限公司 | FXIa凝血因子抑制剂、其药物组合物和用途 |
| CN112341377B (zh) * | 2019-08-09 | 2024-05-14 | 上海美悦生物科技发展有限公司 | 一种杂环类化合物及其应用 |
| WO2021057818A1 (zh) * | 2019-09-27 | 2021-04-01 | 深圳信立泰药业股份有限公司 | FXIa抑制剂及其制备方法和医药用途 |
| CN113005176A (zh) * | 2019-12-20 | 2021-06-22 | 深圳市帝迈生物技术有限公司 | 稳定剂、凝血酶原时间检测试剂及其制备方法、试剂盒 |
| WO2022018156A1 (en) * | 2020-07-22 | 2022-01-27 | Janssen Pharmaceutica Nv | Compounds useful as factor xia inhibitors |
| JP7700218B2 (ja) * | 2020-09-17 | 2025-06-30 | 浙江海正薬業股▲ふん▼有限公司 | ピペラジン誘導体、その製造方法、およびその使用 |
| WO2022083707A1 (zh) * | 2020-10-23 | 2022-04-28 | 深圳信立泰药业股份有限公司 | FXIa抑制剂化合物或其盐的医药用途 |
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| WO2022122035A1 (zh) * | 2020-12-11 | 2022-06-16 | 上海领泰生物医药科技有限公司 | 凝血因子XIa抑制剂及其制备方法和应用 |
| CN112675173B (zh) * | 2020-12-25 | 2022-04-05 | 华南理工大学 | FXIa抑制剂化合物或其盐的医药用途 |
| WO2022194225A1 (zh) * | 2021-03-18 | 2022-09-22 | 深圳信立泰药业股份有限公司 | FXIa抑制剂化合物杂质及其制备方法和用途FXIa抑制剂化合物杂质及其制备方法和用途 |
| CN116283750B (zh) * | 2021-09-09 | 2025-02-07 | 成都泰和伟业生物科技有限公司 | 一种杂环酰胺类衍生物及其制备方法和用途 |
| CN116199672A (zh) * | 2021-11-30 | 2023-06-02 | 成都泰和伟业生物科技有限公司 | 一种嘧啶酰胺类衍生物及其制备方法和用途 |
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| CN117164562B (zh) * | 2023-09-07 | 2025-06-13 | 成都施贝康生物医药科技有限公司 | 一种氧代哒嗪类化合物及其制备方法和用途 |
| CN117164564B (zh) * | 2023-09-07 | 2025-07-08 | 成都施贝康生物医药科技有限公司 | 氧代哒嗪类化合物及其制备方法和用途 |
| CN117164566B (zh) * | 2023-09-07 | 2025-06-06 | 成都施贝康生物医药科技有限公司 | 一种氧代哒嗪类化合物及其制备方法和用途 |
| CN117164563B (zh) * | 2023-09-07 | 2025-06-10 | 成都施贝康生物医药科技有限公司 | 氧代嘧啶类化合物及其制备方法和用途 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3900483A (en) * | 1972-04-15 | 1975-08-19 | Konishiroku Photo Ind | ' -(2(1h)pyridone)+65 -pivalyl-5-(' -2,4-di-t-amyl-phenoxybutyramide)-acetanilides and derivatives |
| US4008086A (en) * | 1972-04-15 | 1977-02-15 | Konishiroku Photo Industry Co., Ltd. | Silver halide emulsion containing photographic yellow coupler |
| ATE27T1 (de) | 1978-05-08 | 1981-04-15 | Ucb Sa | Lactam-n-essigsaeuren und ihre amide, verfahren zu ihrer herstellung und heilmittel, die sie enthalten |
| EP0028489B1 (en) | 1979-11-05 | 1983-10-05 | Beecham Group Plc | Enzyme derivatives, and their preparation |
| BR8108745A (pt) | 1980-08-07 | 1982-07-06 | Diamond Shamrock Corp | Difenilpiridazinonas herbicidas e reguladores do crescimento da planta |
| AU1595997A (en) | 1996-01-26 | 1997-08-20 | Smithkline Beecham Plc | Thienoxazinone derivatives useful as antiviral agents |
| PE121699A1 (es) | 1997-02-18 | 1999-12-08 | Boehringer Ingelheim Pharma | Heterociclos biciclicos disustituidos como inhibidores de la trombina |
| ZA985247B (en) | 1997-06-19 | 1999-12-17 | Du Pont Merck Pharma | Guanidine mimics as factor Xa inhibitors. |
| WO2000077027A2 (en) | 1999-06-14 | 2000-12-21 | Tularik Limited | Serine protease inhibitors |
| US6329372B1 (en) | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| AR035216A1 (es) | 2000-12-01 | 2004-05-05 | Astrazeneca Ab | Derivados de acido mandelico ,derivados farmaceuticamente aceptables, uso de estos derivados para la fabricacion de medicamentos, metodos de tratamiento ,procesos para la preparacion de estos derivados, y compuestos intermediarios |
| WO2002094787A1 (en) | 2001-05-23 | 2002-11-28 | Ucb, S.A. | 2-oxo-piperidinyl- and 2-oxo-azepanyl alkanoic acid derivativ es for the treatment of epilepsy and other neurological disorders |
| AU2002341693B2 (en) | 2001-09-21 | 2008-05-29 | Bristol-Myers Squibb Holdings Ireland Unlimited Company | Lactam-containing compounds and derivatives thereof as factor Xa inhibitors |
| AU2003298740A1 (en) | 2002-12-05 | 2004-06-30 | Axys Pharmaceuticals, Inc. | Cyanomethyl derivatives as cysteine protease inhibitors |
| ZA200504813B (en) | 2002-12-24 | 2006-10-25 | Daiichi Seiyaku Co | Novel ethylenediamine derivatives |
| US20040180855A1 (en) | 2003-02-19 | 2004-09-16 | Schumacher William A. | Methods of treating thrombosis with reduced risk of increased bleeding times |
| WO2005061462A2 (en) | 2003-12-19 | 2005-07-07 | Neurogen Corporation | Diaryl pyrazole derivatives and their use as neurokinin-3 receptor modulators |
| WO2006090234A1 (en) | 2005-02-22 | 2006-08-31 | Ranbaxy Laboratories Limited | Heterocyclic derivatives as cell adhesion inhibitors |
| US8865707B2 (en) | 2005-12-30 | 2014-10-21 | Merck Sharp & Dohme Corp. | Cholesteryl ester transfer protein inhibitors |
| TW200829171A (en) | 2006-11-17 | 2008-07-16 | Nihon Nohyaku Co Ltd | Haloalkyl sulfonanilide derivatives or salts thereof, herbicide using it as effective constituent and use-method thereof |
| PT2099769E (pt) | 2006-12-07 | 2012-08-31 | Novartis Ag | 6-oxo-1,6-di-hidropirimidin-2-ilos no tratamento de doenças proliferativas |
| WO2008106128A2 (en) | 2007-02-26 | 2008-09-04 | Vitae Pharmaceuticals, Inc. | CYCLIC UREA AND CARBAMATE INHIBITORS OF 11β -HYDROXYSTEROID DEHYDROGENASE 1 |
| WO2009078498A1 (en) | 2007-12-17 | 2009-06-25 | Green Cross Corporation | Biarylpyrazole 4-carboxamides as cannabinoid cb1 receptor ligands |
| CA2715290A1 (en) | 2008-02-15 | 2009-08-20 | Vitae Pharmaceuticals, Inc. | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| AR071069A1 (es) | 2008-03-26 | 2010-05-26 | Takeda Pharmaceutical | Derivados sustituidos de pirazol y su uso para la prevencion o el tratamiento de cancer |
| US8258134B2 (en) | 2008-04-16 | 2012-09-04 | Hoffmann-La Roche Inc. | Pyridazinone glucokinase activators |
| EP2297112B1 (en) | 2008-05-06 | 2013-04-03 | Boehringer Ingelheim International GmbH | Pyrazole compounds as ccr1 antagonists |
| WO2010111059A1 (en) | 2009-03-23 | 2010-09-30 | Merck Sharp & Dohme Corp. | P2x3 receptor antagonists for treatment of pain |
| JP2010280638A (ja) | 2009-06-08 | 2010-12-16 | Nippon Nohyaku Co Ltd | ハロアルキルスルホンアニリド誘導体又はその塩類及びこれを有効成分とする除草剤並びにその使用方法 |
| CA2778684A1 (en) | 2009-10-29 | 2011-05-05 | Schering Corporation | Bridged bicyclic piperidine derivatives and methods of use thereof |
| CN103987696B (zh) * | 2011-10-14 | 2016-12-21 | 百时美施贵宝公司 | 作为因子xia抑制剂的取代的四氢异喹啉化合物 |
| IN2014CN04676A (OSRAM) | 2011-12-21 | 2015-09-18 | Ono Pharmaceutical Co | |
| HUE032622T2 (en) * | 2012-08-03 | 2017-10-30 | Bristol Myers Squibb Co | Dihydropyridone p1 as factor xia inhibitors |
| AU2014214325B2 (en) | 2013-02-06 | 2018-06-07 | Merck Patent Gmbh | Substituted carboxylic acid derivatives as aggrecanase inhibitors for the treatment of osteoarthritis |
| WO2014160592A2 (en) * | 2013-03-27 | 2014-10-02 | Merck Sharp & Dohme Corp. | FACTOR XIa INHIBITORS |
| EP3331872B1 (en) | 2015-08-05 | 2019-09-25 | Bristol-Myers Squibb Company | Novel substituted glycine derived fxia inhibitors |
-
2016
- 2016-08-03 EP EP16750350.7A patent/EP3331872B1/en active Active
- 2016-08-03 CN CN201680058331.8A patent/CN108137549B/zh active Active
- 2016-08-03 ES ES16750350T patent/ES2754599T3/es active Active
- 2016-08-03 JP JP2018505695A patent/JP6785838B2/ja active Active
- 2016-08-03 KR KR1020187005764A patent/KR102697816B1/ko active Active
- 2016-08-03 US US15/750,212 patent/US10336730B2/en active Active
- 2016-08-03 WO PCT/US2016/045276 patent/WO2017023992A1/en not_active Ceased
-
2019
- 2019-06-27 US US16/454,848 patent/US10899743B2/en active Active
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