JP2015516392A5 - - Google Patents
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- Publication number
- JP2015516392A5 JP2015516392A5 JP2015505896A JP2015505896A JP2015516392A5 JP 2015516392 A5 JP2015516392 A5 JP 2015516392A5 JP 2015505896 A JP2015505896 A JP 2015505896A JP 2015505896 A JP2015505896 A JP 2015505896A JP 2015516392 A5 JP2015516392 A5 JP 2015516392A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazo
- pyrazin
- phenylethyl
- pentan
- bromo
- 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 description 78
- 210000002027 skeletal muscle Anatomy 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 45
- 229940125913 troponin activator Drugs 0.000 claims description 43
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 38
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 38
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 32
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 30
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- -1 hexa-1-enyl Chemical group 0.000 claims description 19
- 210000003371 toe Anatomy 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 206010019280 Heart failures Diseases 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- RSQGZEAXODVTOL-UHFFFAOYSA-N 5-ethynyl-3-pentan-3-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C#CC1=CN=C2NC(=O)N(C(CC)CC)C2=N1 RSQGZEAXODVTOL-UHFFFAOYSA-N 0.000 claims description 7
- 208000030175 lameness Diseases 0.000 claims description 7
- 206010049565 Muscle fatigue Diseases 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000004220 muscle function Effects 0.000 claims description 3
- 239000005541 ACE inhibitor Substances 0.000 claims description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 claims description 2
- 239000005528 B01AC05 - Ticlopidine Substances 0.000 claims description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 2
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 claims description 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 2
- 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 2
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 2
- 239000002170 aldosterone antagonist Substances 0.000 claims description 2
- 229940083712 aldosterone antagonist Drugs 0.000 claims description 2
- 238000002399 angioplasty Methods 0.000 claims description 2
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 2
- 229940127218 antiplatelet drug Drugs 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000002876 beta blocker Substances 0.000 claims description 2
- 229940097320 beta blocking agent Drugs 0.000 claims description 2
- 239000000480 calcium channel blocker Substances 0.000 claims description 2
- 229960004195 carvedilol Drugs 0.000 claims description 2
- NPAKNKYSJIDKMW-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=NC3=CC=C[CH]C3=C12 NPAKNKYSJIDKMW-UHFFFAOYSA-N 0.000 claims description 2
- 229960003009 clopidogrel Drugs 0.000 claims description 2
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 claims description 2
- 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 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 229960005156 digoxin Drugs 0.000 claims description 2
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical group C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 claims description 2
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 claims description 2
- 239000002934 diuretic Substances 0.000 claims description 2
- 229940030606 diuretics Drugs 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 229960001208 eplerenone Drugs 0.000 claims description 2
- JUKPWJGBANNWMW-VWBFHTRKSA-N eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 claims description 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 2
- 230000003834 intracellular effect Effects 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229960002237 metoprolol Drugs 0.000 claims description 2
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 2
- 210000003205 muscle Anatomy 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229960002256 spironolactone Drugs 0.000 claims description 2
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 238000001356 surgical procedure Methods 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229960005001 ticlopidine Drugs 0.000 claims description 2
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 claims description 2
- SBJUQVUTJXSWQG-UHFFFAOYSA-N 5-ethenyl-3-pentan-3-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C=CC1=CN=C2NC(=O)N(C(CC)CC)C2=N1 SBJUQVUTJXSWQG-UHFFFAOYSA-N 0.000 claims 5
- SSZGBXHOXMJQIV-NSCUHMNNSA-N 3-(oxan-4-yl)-5-[(e)-prop-1-enyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(/C=C/C)=CN=C2N=C(O)N1C1CCOCC1 SSZGBXHOXMJQIV-NSCUHMNNSA-N 0.000 claims 4
- SSZGBXHOXMJQIV-IHWYPQMZSA-N 3-(oxan-4-yl)-5-[(z)-prop-1-enyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(\C=C/C)=CN=C2NC(=O)N1C1CCOCC1 SSZGBXHOXMJQIV-IHWYPQMZSA-N 0.000 claims 4
- NSPIDWPREXAAAQ-QHHAFSJGSA-N 3-cyclohexyl-5-[(e)-prop-1-enyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(/C=C/C)=CN=C2NC(=O)N1C1CCCCC1 NSPIDWPREXAAAQ-QHHAFSJGSA-N 0.000 claims 4
- KUFBAWMESFZISC-NSCUHMNNSA-N 3-cyclopropyl-5-[(e)-prop-1-enyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(/C=C/C)=CN=C2NC(=O)N1C1CC1 KUFBAWMESFZISC-NSCUHMNNSA-N 0.000 claims 4
- KUFBAWMESFZISC-IHWYPQMZSA-N 3-cyclopropyl-5-[(z)-prop-1-enyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(\C=C/C)=CN=C2NC(=O)N1C1CC1 KUFBAWMESFZISC-IHWYPQMZSA-N 0.000 claims 4
- TUPQQYNBJJLKFQ-UHFFFAOYSA-N 3-pentan-3-yl-5-(trifluoromethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound FC(F)(F)C1=CN=C2NC(=O)N(C(CC)CC)C2=N1 TUPQQYNBJJLKFQ-UHFFFAOYSA-N 0.000 claims 4
- WYRAXYZTIXGPNA-DAXSKMNVSA-N 3-pentan-3-yl-5-[(z)-prop-1-enyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C\C=C/C1=CN=C2NC(=O)N(C(CC)CC)C2=N1 WYRAXYZTIXGPNA-DAXSKMNVSA-N 0.000 claims 4
- ZUKQRELSXSZGNR-UHFFFAOYSA-N 3-pentan-3-yl-5-prop-1-en-2-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound CC(=C)C1=CN=C2NC(=O)N(C(CC)CC)C2=N1 ZUKQRELSXSZGNR-UHFFFAOYSA-N 0.000 claims 4
- PFKZWBXZBQPWJI-SNAWJCMRSA-N 3-propan-2-yl-5-[(e)-prop-1-enyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C\C=C\C1=CN=C2NC(=O)N(C(C)C)C2=N1 PFKZWBXZBQPWJI-SNAWJCMRSA-N 0.000 claims 4
- PFKZWBXZBQPWJI-PLNGDYQASA-N 3-propan-2-yl-5-[(z)-prop-1-enyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C\C=C/C1=CN=C2N=C(O)N(C(C)C)C2=N1 PFKZWBXZBQPWJI-PLNGDYQASA-N 0.000 claims 4
- OOWPKYXJAWXXJL-UHFFFAOYSA-N 5-(dimethylamino)-3-pentan-3-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=C(N(C)C)N=C2N(C(CC)CC)C(O)=NC2=N1 OOWPKYXJAWXXJL-UHFFFAOYSA-N 0.000 claims 4
- XLKNITFKTUIDMX-UHFFFAOYSA-N 5-bromo-3-(2-methyl-1-morpholin-4-ylpropan-2-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound OC1=NC2=NC=C(Br)N=C2N1C(C)(C)CN1CCOCC1 XLKNITFKTUIDMX-UHFFFAOYSA-N 0.000 claims 4
- JVUXJJNMSWDQNZ-MRVPVSSYSA-N 5-bromo-3-[(2r)-1-morpholin-4-ylpropan-2-yl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C([C@@H](C)N1C2=NC(Br)=CN=C2N=C1O)N1CCOCC1 JVUXJJNMSWDQNZ-MRVPVSSYSA-N 0.000 claims 4
- GMOWAKFCILZILA-GFCCVEGCSA-N 5-ethynyl-3-[(2r)-1-morpholin-4-ylbutan-2-yl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C([C@@H](CC)N1C2=NC(=CN=C2N=C1O)C#C)N1CCOCC1 GMOWAKFCILZILA-GFCCVEGCSA-N 0.000 claims 4
- JCLOPOHRCQTTGK-UHFFFAOYSA-N 5-methoxy-3-pentan-3-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=C(OC)N=C2N(C(CC)CC)C(O)=NC2=N1 JCLOPOHRCQTTGK-UHFFFAOYSA-N 0.000 claims 4
- NSPIDWPREXAAAQ-KXFIGUGUSA-N 3-cyclohexyl-5-[(z)-prop-1-enyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(\C=C/C)=CN=C2NC(=O)N1C1CCCCC1 NSPIDWPREXAAAQ-KXFIGUGUSA-N 0.000 claims 3
- WYRAXYZTIXGPNA-QPJJXVBHSA-N 3-pentan-3-yl-5-[(e)-prop-1-enyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C/C=C/C1=CN=C2NC(=O)N(C(CC)CC)C2=N1 WYRAXYZTIXGPNA-QPJJXVBHSA-N 0.000 claims 3
- RKWUIYMGQOAXEZ-UHFFFAOYSA-N 3-pentan-3-yl-5-prop-1-ynyl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound CC#CC1=CN=C2NC(=O)N(C(CC)CC)C2=N1 RKWUIYMGQOAXEZ-UHFFFAOYSA-N 0.000 claims 3
- WAXQRVPDPGLRKE-QMMMGPOBSA-N 5-bromo-3-[(1s)-1-phenylethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical group C1([C@H](C)N2C(NC3=NC=C(Br)N=C32)=O)=CC=CC=C1 WAXQRVPDPGLRKE-QMMMGPOBSA-N 0.000 claims 3
- YHNUAFQPACGRHG-UHFFFAOYSA-N 2-(5-bromo-2-oxo-1h-imidazo[4,5-b]pyrazin-3-yl)butanoic acid Chemical compound C1=C(Br)N=C2N(C(C(O)=O)CC)C(O)=NC2=N1 YHNUAFQPACGRHG-UHFFFAOYSA-N 0.000 claims 2
- OEKBTLYYLIHXOZ-UHFFFAOYSA-N 2-oxo-1-pentan-3-yl-3h-imidazo[4,5-b]pyrazine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C2N(C(CC)CC)C(O)=NC2=N1 OEKBTLYYLIHXOZ-UHFFFAOYSA-N 0.000 claims 2
- UPHGKXBLNGRTEU-VIFPVBQESA-N 2-oxo-3-[(1s)-1-phenylethyl]-1h-imidazo[4,5-b]pyrazine-5-carbonitrile Chemical compound C1([C@H](C)N2C3=NC(=CN=C3N=C2O)C#N)=CC=CC=C1 UPHGKXBLNGRTEU-VIFPVBQESA-N 0.000 claims 2
- AUEBQUCREPKUBN-QMMMGPOBSA-N 2-oxo-3-[(1s)-1-phenylethyl]-1h-imidazo[4,5-b]pyrazine-5-carboxylic acid Chemical compound C1([C@H](C)N2C3=NC(=CN=C3N=C2O)C(O)=O)=CC=CC=C1 AUEBQUCREPKUBN-QMMMGPOBSA-N 0.000 claims 2
- BWMYZRWUZRHUKK-UHFFFAOYSA-N 2-oxo-3-pentan-3-yl-1h-imidazo[4,5-b]pyrazine-5-carbonitrile Chemical compound C1=C(C#N)N=C2N(C(CC)CC)C(O)=NC2=N1 BWMYZRWUZRHUKK-UHFFFAOYSA-N 0.000 claims 2
- OIDUDOFDKDVFTB-UHFFFAOYSA-N 3-(1-aminobutan-2-yl)-5-bromo-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=C(Br)N=C2N(C(CN)CC)C(O)=NC2=N1 OIDUDOFDKDVFTB-UHFFFAOYSA-N 0.000 claims 2
- ZKELHGFJSAVRCZ-UHFFFAOYSA-N 3-(1-morpholin-4-ylbutan-2-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound OC1=NC2=NC=CN=C2N1C(CC)CN1CCOCC1 ZKELHGFJSAVRCZ-UHFFFAOYSA-N 0.000 claims 2
- GXTJPCRFZLLAQY-VIFPVBQESA-N 3-[(1s)-1-phenylethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](C)N2C(NC3=NC=CN=C32)=O)=CC=CC=C1 GXTJPCRFZLLAQY-VIFPVBQESA-N 0.000 claims 2
- KMPZIANLLDHFPH-NSHDSACASA-N 3-[(1s)-1-phenylethyl]-1h-imidazo[4,5-b]quinoxalin-2-one Chemical compound C1([C@H](C)N2C(NC3=NC4=CC=CC=C4N=C32)=O)=CC=CC=C1 KMPZIANLLDHFPH-NSHDSACASA-N 0.000 claims 2
- FGVNKQWCHAKDRY-AWEZNQCLSA-N 3-[(1s)-1-phenylethyl]-5-(piperidin-1-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](C)N2C(NC3=NC=C(CN4CCCCC4)N=C32)=O)=CC=CC=C1 FGVNKQWCHAKDRY-AWEZNQCLSA-N 0.000 claims 2
- SFDROONMRQVZOL-ZDUSSCGKSA-N 3-[(1s)-1-phenylethyl]-5-(piperidine-1-carbonyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](C)N2C(NC3=NC=C(N=C32)C(=O)N2CCCCC2)=O)=CC=CC=C1 SFDROONMRQVZOL-ZDUSSCGKSA-N 0.000 claims 2
- SYUYQEHWWBTQJK-UFVHFEBBSA-N 3-[(1s)-1-phenylethyl]-5-[(z)-prop-1-enyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](C)N2C(=O)NC3=NC=C(N=C32)\C=C/C)=CC=CC=C1 SYUYQEHWWBTQJK-UFVHFEBBSA-N 0.000 claims 2
- HGXDYLNWUSYQKP-NSHDSACASA-N 3-[(1s)-1-phenylethyl]-5-propyl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](C)N2C(=O)NC3=NC=C(N=C32)CCC)=CC=CC=C1 HGXDYLNWUSYQKP-NSHDSACASA-N 0.000 claims 2
- FMCGTDCYKPWFQL-UHFFFAOYSA-N 3-benzyl-5-bromo-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(Br)=CN=C2NC(=O)N1CC1=CC=CC=C1 FMCGTDCYKPWFQL-UHFFFAOYSA-N 0.000 claims 2
- GZESQDDXLPQCPD-UHFFFAOYSA-N 3-benzyl-5-methylsulfanyl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(SC)=CN=C2NC(=O)N1CC1=CC=CC=C1 GZESQDDXLPQCPD-UHFFFAOYSA-N 0.000 claims 2
- QTFTVOGPJMOQQQ-UHFFFAOYSA-N 3-cyclohexyl-5-methylsulfanyl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(SC)=CN=C2N=C(O)N1C1CCCCC1 QTFTVOGPJMOQQQ-UHFFFAOYSA-N 0.000 claims 2
- WJOZHHCMYYPKPL-UHFFFAOYSA-N 3-cyclopropyl-5-methylsulfanyl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(SC)=CN=C2NC(=O)N1C1CC1 WJOZHHCMYYPKPL-UHFFFAOYSA-N 0.000 claims 2
- LJPNHODRROZMGG-UHFFFAOYSA-N 3-pentan-3-yl-1,4-dihydroimidazo[4,5-b]pyrazine-2,5-dione Chemical compound C1=C(O)N=C2N(C(CC)CC)C(O)=NC2=N1 LJPNHODRROZMGG-UHFFFAOYSA-N 0.000 claims 2
- OQTVWLOQVMHOME-UHFFFAOYSA-N 3-pentan-3-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CN=C2N(C(CC)CC)C(O)=NC2=N1 OQTVWLOQVMHOME-UHFFFAOYSA-N 0.000 claims 2
- QWIGXPXZXMRYFN-UHFFFAOYSA-N 3-pentan-3-yl-1h-imidazo[4,5-b]quinoxalin-2-one Chemical compound C1=CC=C2N=C(NC(N3C(CC)CC)=O)C3=NC2=C1 QWIGXPXZXMRYFN-UHFFFAOYSA-N 0.000 claims 2
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- NAPPLGJAEMHOAG-UHFFFAOYSA-N n-methyl-2-oxo-1-pentan-3-yl-3h-imidazo[4,5-b]pyrazine-5-carboxamide Chemical compound CNC(=O)C1=CN=C2N(C(CC)CC)C(O)=NC2=N1 NAPPLGJAEMHOAG-UHFFFAOYSA-N 0.000 claims 2
- QYQZBGDQEVAJKO-VIFPVBQESA-N n-methyl-2-oxo-3-[(1s)-1-phenylethyl]-1h-imidazo[4,5-b]pyrazine-5-carboxamide Chemical compound C1([C@H](C)N2C(O)=NC3=NC=C(N=C32)C(=O)NC)=CC=CC=C1 QYQZBGDQEVAJKO-VIFPVBQESA-N 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- AKWIAIDKXNKXDI-UHFFFAOYSA-N 1h-pyrrole-3-carboxamide Chemical compound NC(=O)C=1C=CNC=1 AKWIAIDKXNKXDI-UHFFFAOYSA-N 0.000 claims 1
- FAICLJXBBVXJHR-QMMMGPOBSA-N 2-oxo-3-[(1s)-1-phenylethyl]-1h-imidazo[4,5-b]pyrazine-5-carboxamide Chemical compound C1([C@H](C)N2C3=NC(=CN=C3N=C2O)C(N)=O)=CC=CC=C1 FAICLJXBBVXJHR-QMMMGPOBSA-N 0.000 claims 1
- SSZWKKQDZMVWCW-UHFFFAOYSA-N 3,5,6-trimethyl-1h-imidazo[4,5-b]pyrazin-2-one Chemical group N1=C(C)C(C)=NC2=C1N(C)C(=O)N2 SSZWKKQDZMVWCW-UHFFFAOYSA-N 0.000 claims 1
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- DGXUBNJTSDKMNH-UHFFFAOYSA-N 3-[2-[[3-fluoro-1-(3-fluoropyridin-2-yl)cyclobutyl]methylamino]pyrimidin-5-yl]benzamide Chemical group NC(=O)C1=CC=CC(C=2C=NC(NCC3(CC(F)C3)C=3C(=CC=CN=3)F)=NC=2)=C1 DGXUBNJTSDKMNH-UHFFFAOYSA-N 0.000 claims 1
- VGMPXCLEQITWTP-UHFFFAOYSA-N 3-methyl-1h-imidazo[4,5-b]pyrazin-2-one Chemical group C1=CN=C2NC(=O)N(C)C2=N1 VGMPXCLEQITWTP-UHFFFAOYSA-N 0.000 claims 1
- AEUJTZJJOJMFJG-UHFFFAOYSA-N 3-piperidin-4-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=CN=C2N1C1CCNCC1 AEUJTZJJOJMFJG-UHFFFAOYSA-N 0.000 claims 1
- XGYMKEPKOZVQSB-UHFFFAOYSA-N 5-(hydroxymethyl)-1,6-dimethyl-3h-imidazo[4,5-b]pyrazin-2-one Chemical group N1=C(CO)C(C)=NC2=C1NC(=O)N2C XGYMKEPKOZVQSB-UHFFFAOYSA-N 0.000 claims 1
- QZCBPABKXFZXCW-UHFFFAOYSA-N 5-[2-(2-oxo-3-pentan-3-yl-1h-imidazo[4,5-b]pyrazin-5-yl)ethynyl]-3-pentan-3-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1=C2NC(=O)N(C(CC)CC)C2=NC(C#CC2=CN=C3N=C(O)N(C3=N2)C(CC)CC)=C1 QZCBPABKXFZXCW-UHFFFAOYSA-N 0.000 claims 1
- QUCSBNPOJMPNDS-UHFFFAOYSA-N 5-bromo-3-[(3-nitrophenyl)methyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical group [O-][N+](=O)C1=CC=CC(CN2C(NC3=NC=C(Br)N=C32)=O)=C1 QUCSBNPOJMPNDS-UHFFFAOYSA-N 0.000 claims 1
- DZHHDFNQNKJYQE-UHFFFAOYSA-N 5-bromo-3-[1-(4-methylpiperazin-1-yl)butan-2-yl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound OC1=NC2=NC=C(Br)N=C2N1C(CC)CN1CCN(C)CC1 DZHHDFNQNKJYQE-UHFFFAOYSA-N 0.000 claims 1
- CHJDFFWYGFUOHU-UHFFFAOYSA-N C(=CC)N1C(=NC=2C1=NC=CN=2)O Chemical compound C(=CC)N1C(=NC=2C1=NC=CN=2)O CHJDFFWYGFUOHU-UHFFFAOYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 210000002683 foot Anatomy 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- 0 **c1c(*)nc(N(*)*)nc1* Chemical compound **c1c(*)nc(N(*)*)nc1* 0.000 description 1
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| US8299248B2 (en) | 2006-08-02 | 2012-10-30 | Cytokinetics, Incorporated | Certain 1H-imidazo[4,5-b]pyrazin-2(3H)-ones and 1H-imidazo[4,5-b]pyrazin-2-ols and methods for their use |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| EP2560488B1 (en) | 2010-04-23 | 2015-10-28 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| EA201791043A1 (ru) | 2011-07-13 | 2017-09-29 | Сайтокинетикс, Инк. | Комбинированная терапия бокового амиотрофического склероза |
| WO2014141104A1 (en) | 2013-03-14 | 2014-09-18 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant idh |
| DK3137622T3 (da) * | 2014-04-29 | 2022-02-07 | Cytokinetics Inc | Fremgangsmåder til at reducere tilbagegang af vitalkapacitet |
| JP6769963B2 (ja) | 2014-08-29 | 2020-10-14 | ティエエッセ ファルマ ソチエタ レスポンサビリタ リミタータ | α−アミノ−β−カルボキシムコン酸セミアルデヒド脱炭酸酵素の阻害剤 |
| BR112017004505A2 (pt) * | 2014-09-09 | 2018-01-23 | Astellas Pharma Inc. | agente terapêutico e método para prevenção e/ou tratamento de incontinência urinária, e, composto ou um sal do mesmo. |
| KR20180120701A (ko) | 2016-02-12 | 2018-11-06 | 아스테라스 세이야쿠 가부시키가이샤 | 테트라히드로이소퀴놀린 유도체 |
| EP3484876A1 (en) | 2016-07-14 | 2019-05-22 | Pfizer Inc | Novel pyrimidine carboxamides as inhibitors of vanin-1 enzyme |
| WO2018165520A1 (en) | 2017-03-10 | 2018-09-13 | Vps-3, Inc. | Metalloenzyme inhibitor compounds |
| JP2022541124A (ja) | 2019-07-23 | 2022-09-22 | アモーフィカル リミテッド． | 運動能力を向上させるための非晶質炭酸カルシウム |
| JP2023548342A (ja) | 2020-11-06 | 2023-11-16 | サイトキネティックス， インコーポレイテッド | 二環式１，４－ジアゼパノン及びその治療的使用 |
| WO2023107705A1 (en) | 2021-12-10 | 2023-06-15 | Incyte Corporation | Bicyclic amines as cdk12 inhibitors |
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| US8227603B2 (en) * | 2006-08-01 | 2012-07-24 | Cytokinetics, Inc. | Modulating skeletal muscle |
| CN101522681B (zh) * | 2006-08-02 | 2012-10-03 | 赛特凯恩蒂克公司 | 特定的化学个体、组合物和方法 |
| US8299248B2 (en) * | 2006-08-02 | 2012-10-30 | Cytokinetics, Incorporated | Certain 1H-imidazo[4,5-b]pyrazin-2(3H)-ones and 1H-imidazo[4,5-b]pyrazin-2-ols and methods for their use |
| BRPI0907502A2 (pt) * | 2008-02-04 | 2019-01-15 | Cytokinetics Inc | pelo menos um entidade química, composição, e, métodos para tratar um paciente tendo uma condição, para aumentar a função ou atividade do músculo esquelético, para aumentar a eficiência do músculo esquelético, parab aumentar o tempo da fadiga de fibra muscular esquelética rápida, para sensibilizar uma fibra muscular esquelética rápida para produzir força em resposta a baixas concentreações de íons cálcio e para aumentar o tempo de fadiga muscular esquelética |
| AR081331A1 (es) * | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| MX354965B (es) * | 2012-04-02 | 2018-03-27 | Cytokinetics Inc | Metodo para mejorar la funcion del diafragma. |
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- 2013-04-11 AU AU2013245917A patent/AU2013245917A1/en not_active Abandoned
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- 2013-04-11 EA EA201491666A patent/EA032480B1/ru not_active IP Right Cessation
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2014
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2017
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2018
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