JP2018522046A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562201267P | 2015-08-05 | 2015-08-05 | |
| US62/201,267 | 2015-08-05 | ||
| PCT/US2016/045276 WO2017023992A1 (en) | 2015-08-05 | 2016-08-03 | Novel substituted glycine derived fxia inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018522046A JP2018522046A (ja) | 2018-08-09 |
| JP2018522046A5 true JP2018522046A5 (enExample) | 2019-09-12 |
| JP6785838B2 JP6785838B2 (ja) | 2020-11-18 |
Family
ID=56618292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018505695A Active JP6785838B2 (ja) | 2015-08-05 | 2016-08-03 | 新規な置換グリシン誘導のｆｘｉａ阻害剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US10336730B2 (enExample) |
| EP (1) | EP3331872B1 (enExample) |
| JP (1) | JP6785838B2 (enExample) |
| KR (1) | KR102697816B1 (enExample) |
| CN (1) | CN108137549B (enExample) |
| ES (1) | ES2754599T3 (enExample) |
| WO (1) | WO2017023992A1 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2762987T3 (es) | 2015-06-19 | 2020-05-26 | Bristol Myers Squibb Co | Macrociclos de diamida como inhibidores del factor XIA |
| JO3703B1 (ar) * | 2015-07-09 | 2021-01-31 | Bayer Pharma AG | مشتقات أوكسوبيريدين مستبدلة |
| EP3868753B1 (en) | 2015-07-29 | 2022-12-21 | Bristol-Myers Squibb Company | Factor xia macrocyclic inhibitors bearing a non-aromatic p2' group |
| 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 |
| WO2017023992A1 (en) | 2015-08-05 | 2017-02-09 | 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 |
| EP3822264A4 (en) | 2018-07-02 | 2021-11-10 | Jiangsu Hengrui Medicine Co., Ltd. | CRYSTALLINE FORMS OF AN OXYPYRIDINE AMIDE DERIVATIVE AND THEIR PREPARATION PROCESS |
| TW202019904A (zh) * | 2018-07-19 | 2020-06-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 一種凝血因子ＸＩａ抑制劑及其中間體的製備方法 |
| 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 |
| KR20220084301A (ko) * | 2019-09-27 | 2022-06-21 | 심천 사루브리스 퍼머수티칼스 컴퍼니 리미티드 | FXIa 억제제와 이의 제조 방법 및 의약 용도 |
| 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 |
| ES3048448T3 (en) * | 2020-07-22 | 2025-12-10 | Janssen Pharmaceutica Nv | Compounds useful as factor xia inhibitors |
| EP4215525A4 (en) * | 2020-09-17 | 2024-08-21 | Zhejiang Hisun Pharmaceutical Co., Ltd. | Piperazine derivative, preparation method therefor and use thereof |
| WO2022083706A1 (zh) * | 2020-10-23 | 2022-04-28 | 深圳信立泰药业股份有限公司 | FXIa抑制剂化合物的盐及其制备方法和医药用途 |
| CN115427043B (zh) * | 2020-10-23 | 2023-04-07 | 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 |
| CN112679446A (zh) * | 2020-10-26 | 2021-04-20 | 都创(上海)医药科技有限公司 | 一种合成反式-3-(3-氯-2-氟-6-(1h-四氮唑-1-基)苯基)丙烯酸的方法 |
| 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 |
| CN115461330A (zh) * | 2021-03-18 | 2022-12-09 | 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 |
| 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 |
| CN116262740A (zh) * | 2022-11-18 | 2023-06-16 | 成都施贝康生物医药科技有限公司 | 新型氧代吡啶类化合物及其制备方法和用途 |
| TW202515882A (zh) | 2023-06-30 | 2025-04-16 | 大陸商深圳信立泰藥業股份有限公司 | 一種多取代的大環化合物及其製備方法與應用 |
| 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 |
| 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 |
| 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 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4008086A (en) * | 1972-04-15 | 1977-02-15 | Konishiroku Photo Industry Co., Ltd. | Silver halide emulsion containing photographic yellow coupler |
| 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 |
| DE2960194D1 (en) | 1978-05-08 | 1981-04-16 | Ucb Sa | Lactam-n-acetic acids, their amides, process for their preparation and therapeutic compositions containing them |
| DE3065190D1 (en) | 1979-11-05 | 1983-11-10 | Beecham Group Plc | Enzyme derivatives, and their preparation |
| JPS57501328A (enExample) | 1980-08-07 | 1982-07-29 | ||
| WO1997027200A1 (en) | 1996-01-26 | 1997-07-31 | 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. |
| US6329372B1 (en) | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| AU5546000A (en) | 1999-06-14 | 2001-01-02 | Protherics Molecular Design Limited | Compounds |
| 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 |
| EP1395560A1 (en) | 2001-05-23 | 2004-03-10 | Ucb, S.A. | 2-oxo-piperidinyl- and 2-oxo-azepanyl alkanoic acid derivativ es for the treatment of epilepsy and other neurological disorders |
| BRPI0212726B8 (pt) | 2001-09-21 | 2021-05-25 | Bristol Myers Squibb Co | compostos contendo lactamas, e derivados dos mesmos, composição farmacêutica que os compreende e seus usos |
| US20060122184A1 (en) | 2002-12-05 | 2006-06-08 | Axys Pharmaceuticals, Inc. | Cyanomethyl derivatives as cysteine protease inhibitors |
| AU2003292748A1 (en) | 2002-12-24 | 2004-07-22 | Daiichi Pharmaceutical Co., Ltd. | 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 |
| WO2007081570A2 (en) | 2005-12-30 | 2007-07-19 | Merck & Co., Inc. | 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 |
| ATE517873T1 (de) | 2006-12-07 | 2011-08-15 | Novartis Ag | 6-oxo-1,6-dihydropyrimidin-2-yle bei der behandlung proliferativer krankheiten |
| EP2125750B1 (en) | 2007-02-26 | 2014-05-21 | Vitae Pharmaceuticals, Inc. | Cyclic urea and carbamate inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2009078498A1 (en) | 2007-12-17 | 2009-06-25 | Green Cross Corporation | Biarylpyrazole 4-carboxamides as cannabinoid cb1 receptor ligands |
| US8598160B2 (en) | 2008-02-15 | 2013-12-03 | Vitae Pharmaceuticals, Inc. | Cycloalkyl lactame derivatives as inhibitors of 11-beta-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 |
| CA2722811C (en) | 2008-05-06 | 2016-07-05 | Boehringer Ingelheim International Gmbh | Pyrazole compounds as ccr1 antagonists |
| EP2410858B1 (en) | 2009-03-23 | 2016-09-07 | 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 |
| AU2010313469A1 (en) | 2009-10-29 | 2012-06-07 | Merck Sharp & Dohme Corp. | Bridged Bicyclic Piperidine Derivatives and methods of use thereof |
| ES2579832T3 (es) * | 2011-10-14 | 2016-08-17 | Bristol-Myers Squibb Company | Compuestos de tetrahidroisoquinolina sustituida como inhibidores del factor XIa |
| CN104136431B (zh) | 2011-12-21 | 2017-03-15 | 小野药品工业株式会社 | 作为凝血因子XIa抑制剂的吡啶酮和嘧啶酮衍生物 |
| HUE032622T2 (en) * | 2012-08-03 | 2017-10-30 | Bristol Myers Squibb Co | Dihydropyridone p1 as factor xia inhibitors |
| ES2627281T3 (es) | 2013-02-06 | 2017-07-27 | Merck Patent Gmbh | Derivados del ácido carboxílico sustituidos como agregados agrecanasa para el tratamiento de la artrosis |
| WO2014160592A2 (en) * | 2013-03-27 | 2014-10-02 | Merck Sharp & Dohme Corp. | FACTOR XIa INHIBITORS |
| WO2017023992A1 (en) | 2015-08-05 | 2017-02-09 | Bristol-Myers Squibb Company | Novel substituted glycine derived fxia inhibitors |
-
2016
- 2016-08-03 WO PCT/US2016/045276 patent/WO2017023992A1/en not_active Ceased
- 2016-08-03 ES ES16750350T patent/ES2754599T3/es active Active
- 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 JP JP2018505695A patent/JP6785838B2/ja active Active
- 2016-08-03 US US15/750,212 patent/US10336730B2/en active Active
- 2016-08-03 KR KR1020187005764A patent/KR102697816B1/ko active Active
-
2019
- 2019-06-27 US US16/454,848 patent/US10899743B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018522046A5 (enExample) | ||
| AU2016240033B2 (en) | 1-cyano-pyrrolidine compounds as USP30 inhibitors | |
| AU2022201352A1 (en) | Pyrazole derivatives as MALT1 inhibitors | |
| JP2019504821A5 (enExample) | ||
| AU2011240808B2 (en) | 5, 7-substituted-imidazo [1, 2-c] pyrimidines as inhibitors of JAK kinases | |
| EP2566477B1 (en) | Amino-quinolines as kinase inhibitors | |
| CA2775475C (en) | Pyridinylimidazolone derivatives for the inhibition of pi3 kinases | |
| HUE032770T2 (en) | Novel nk-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in nk-3 receptors mediated disorders | |
| US10703748B2 (en) | Diazanaphthalen-3-yl carboxamides and preparation and use thereof | |
| JP2014521711A5 (enExample) | ||
| EP2603218B1 (en) | Quinolyl amines as kinase inhibitors | |
| JP2019504821A (ja) | ユビキチン特異的プロテアーゼ１阻害剤としてのプリノン | |
| JP2016500671A5 (enExample) | ||
| RU2015129538A (ru) | Замещенные имидазопиридины в качестве ингибиторов hdm2 | |
| US10023576B2 (en) | Heteroaryl substituted pyrrolotriazine amine compounds as PI3K inhibitors | |
| RU2013120966A (ru) | ФУРО[3,2-d]ПИРИМИДИНОВЫЕ СОЕДИНЕНИЯ | |
| RU2017105296A (ru) | Новые соединения | |
| WO2015015318A4 (en) | Novel quinazolinones as bromodomain inhibitors | |
| CZ20031676A3 (en) | Benzimidazole and pyridylimidazole derivatives as ligands for gaba receptors | |
| PT2081937E (pt) | Moduladores de proteína-cinase de triazolo-piridazina | |
| ES2550201T3 (es) | Moduladores de la PDE10 | |
| HRP20250272T1 (hr) | Derivati benzimidazola i njihova uporaba | |
| RU2014119244A (ru) | Гетероциклические соединения и способы их использования | |
| CA3202212A1 (en) | Indole derivatives useful in treating conditions associated with cgas | |
| CN114945571A (zh) | 环状化合物及其使用方法 |