JP2014522847A5 - - Google Patents
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- Publication number
- JP2014522847A5 JP2014522847A5 JP2014519190A JP2014519190A JP2014522847A5 JP 2014522847 A5 JP2014522847 A5 JP 2014522847A5 JP 2014519190 A JP2014519190 A JP 2014519190A JP 2014519190 A JP2014519190 A JP 2014519190A JP 2014522847 A5 JP2014522847 A5 JP 2014522847A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydrobenzo
- phenyl
- alkyl
- oxazepin
- trifluoromethoxy
- 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 description 371
- 125000001072 heteroaryl group Chemical group 0.000 claims description 361
- -1 4-cyclopropoxy, 4-cyclobutylmethoxy Chemical group 0.000 claims description 356
- 125000003118 aryl group Chemical group 0.000 claims description 329
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 315
- 125000000623 heterocyclic group Chemical group 0.000 claims description 315
- 125000005843 halogen group Chemical group 0.000 claims description 199
- 125000001424 substituent group Chemical group 0.000 claims description 189
- NBJDSMIOWPVWRW-UHFFFAOYSA-N 2h-oxazepin-5-one Chemical compound O=C1C=CNOC=C1 NBJDSMIOWPVWRW-UHFFFAOYSA-N 0.000 claims description 154
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 82
- 150000001875 compounds Chemical class 0.000 claims description 78
- 150000002431 hydrogen Chemical class 0.000 claims description 72
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 69
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- 125000000304 alkynyl group Chemical group 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 49
- 229910052799 carbon Inorganic materials 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 47
- 125000003342 alkenyl group Chemical group 0.000 claims description 46
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 43
- 150000002148 esters Chemical class 0.000 claims description 43
- 125000004442 acylamino group Chemical group 0.000 claims description 42
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 38
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 38
- 125000004043 oxo group Chemical group O=* 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- KCUHSGJIUSNWHG-UHFFFAOYSA-N 2,3-dihydrooxazepin-6-one Chemical compound O1NCC=CC(C1)=O KCUHSGJIUSNWHG-UHFFFAOYSA-N 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- YNUAEEJQYHYLMS-UHFFFAOYSA-N 4-(pyrimidin-2-ylmethyl)-7-[4-(trifluoromethoxy)phenyl]-2,3-dihydro-1,4-benzoxazepin-5-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(OCCN(CC=2N=CC=CN=2)C2=O)C2=C1 YNUAEEJQYHYLMS-UHFFFAOYSA-N 0.000 claims description 10
- WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 claims description 9
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 5
- 206010019280 Heart failures Diseases 0.000 claims description 5
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 5
- 208000028867 ischemia Diseases 0.000 claims description 5
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- RPXNJCVSRBNJHA-UHFFFAOYSA-N n-[2-[5-oxo-7-[4-(trifluoromethoxy)phenyl]-2,3-dihydro-1,4-benzoxazepin-4-yl]ethyl]pyrimidine-2-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(OCCN(CCNC(=O)C=2N=CC=CN=2)C2=O)C2=C1 RPXNJCVSRBNJHA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 3
- XOFKKGMAEWHODX-UHFFFAOYSA-N 4-(pyrimidin-2-ylmethyl)-7-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1,4-benzoxazepin-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(OCCN(CC=2N=CC=CN=2)C2=O)C2=C1 XOFKKGMAEWHODX-UHFFFAOYSA-N 0.000 claims description 3
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 3
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 3
- 206010007556 Cardiac failure acute Diseases 0.000 claims description 3
- 208000003037 Diastolic Heart Failure Diseases 0.000 claims description 3
- 206010022562 Intermittent claudication Diseases 0.000 claims description 3
- 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 3
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 208000007718 Stable Angina Diseases 0.000 claims description 3
- 208000008253 Systolic Heart Failure Diseases 0.000 claims description 3
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 3
- 230000000306 recurrent effect Effects 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 2
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 2
- NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 claims description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 206010033799 Paralysis Diseases 0.000 claims description 2
- 208000007814 Unstable Angina Diseases 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000003111 delayed effect Effects 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 208000004296 neuralgia Diseases 0.000 claims description 2
- 208000021722 neuropathic pain Diseases 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- MSMUGKYVPPWLNZ-UHFFFAOYSA-N 1-[4-[5-oxo-4-(pyrimidin-2-ylmethyl)-2,3-dihydro-1,4-benzoxazepin-7-yl]phenyl]cyclopentane-1-carbonitrile Chemical compound C1COC2=CC=C(C=3C=CC(=CC=3)C3(CCCC3)C#N)C=C2C(=O)N1CC1=NC=CC=N1 MSMUGKYVPPWLNZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- VCLXRLYZVCWRIV-UHFFFAOYSA-N n-[2-[5-oxo-7-[4-(trifluoromethoxy)phenyl]-2,3-dihydro-1,4-benzoxazepin-4-yl]ethyl]cyclopropanesulfonamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(OCCN(CCNS(=O)(=O)C2CC2)C2=O)C2=C1 VCLXRLYZVCWRIV-UHFFFAOYSA-N 0.000 claims 2
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims 2
- JXNDSKLORQDUHC-UHFFFAOYSA-N 6-[[5-oxo-7-[4-(trifluoromethoxy)phenyl]-2,3-dihydro-1,4-benzoxazepin-4-yl]methyl]pyridine-2-carbonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(OCCN(CC=2N=C(C=CC=2)C#N)C2=O)C2=C1 JXNDSKLORQDUHC-UHFFFAOYSA-N 0.000 claims 1
- VOTBLROURANVRM-UHFFFAOYSA-N 7-[3-fluoro-4-(trifluoromethyl)phenyl]-4-(pyrimidin-2-ylmethyl)-2,3-dihydro-1,4-benzoxazepin-5-one Chemical compound C1=C(C(F)(F)F)C(F)=CC(C=2C=C3C(=O)N(CC=4N=CC=CN=4)CCOC3=CC=2)=C1 VOTBLROURANVRM-UHFFFAOYSA-N 0.000 claims 1
- 206010002388 Angina unstable Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- GRJHONXDTNBDTC-UHFFFAOYSA-N phenyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC=C1 GRJHONXDTNBDTC-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 42
- QHXILXDHCYOAQA-UHFFFAOYSA-N 2h-1,4-oxazepin-5-one Chemical compound O=C1C=COCC=N1 QHXILXDHCYOAQA-UHFFFAOYSA-N 0.000 description 31
- 125000004965 chloroalkyl group Chemical group 0.000 description 18
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 17
- 241000102542 Kara Species 0.000 description 14
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 description 11
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 125000004419 alkynylene group Chemical group 0.000 description 4
- 125000002757 morpholinyl group Chemical group 0.000 description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 241000239366 Euphausiacea Species 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
- PKVNVXXWANAAFP-UHFFFAOYSA-N 1,7-dihydro-1,4-diazepin-6-one Chemical compound O=C1CNC=CN=C1 PKVNVXXWANAAFP-UHFFFAOYSA-N 0.000 description 2
- GXQLLMGNQZULKS-UHFFFAOYSA-N 1-methyl-4-(2-phenylmethoxyethyl)-7-[4-(trifluoromethoxy)phenyl]-3h-1,4-benzodiazepine-2,5-dione Chemical compound C1C(=O)N(C)C2=CC=C(C=3C=CC(OC(F)(F)F)=CC=3)C=C2C(=O)N1CCOCC1=CC=CC=C1 GXQLLMGNQZULKS-UHFFFAOYSA-N 0.000 description 2
- LBHUBBRMFWBZLH-UHFFFAOYSA-N 4-benzyl-1-methyl-7-[4-(trifluoromethyl)phenyl]-3h-1,4-benzodiazepine-2,5-dione Chemical compound C1C(=O)N(C)C2=CC=C(C=3C=CC(=CC=3)C(F)(F)F)C=C2C(=O)N1CC1=CC=CC=C1 LBHUBBRMFWBZLH-UHFFFAOYSA-N 0.000 description 2
- RDQOUFQBZLSFIE-UHFFFAOYSA-N 4-benzyl-7-[4-(trifluoromethyl)phenyl]-1,3-dihydro-1,4-benzodiazepine-2,5-dione Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(NC(=O)CN(CC=2C=CC=CC=2)C2=O)C2=C1 RDQOUFQBZLSFIE-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 2
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- SVPZJHKVRMRREG-UHFFFAOYSA-N cyclopentanecarbonitrile Chemical compound N#CC1CCCC1 SVPZJHKVRMRREG-UHFFFAOYSA-N 0.000 description 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- MDWWPRNUHKMQCT-UHFFFAOYSA-N 2-cyclopropylthiophene Chemical group C1CC1C1=CC=CS1 MDWWPRNUHKMQCT-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- FGKQHXRVPDLTDF-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazepin-5-one Chemical compound O=C1NCCOC2=CC=CC=C12 FGKQHXRVPDLTDF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 101100037618 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ant-1 gene Proteins 0.000 description 1
- 229910000752 Prince's Metal Inorganic materials 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161503980P | 2011-07-01 | 2011-07-01 | |
| US61/503,980 | 2011-07-01 | ||
| US201161582160P | 2011-12-30 | 2011-12-30 | |
| US61/582,160 | 2011-12-30 | ||
| PCT/US2012/045086 WO2013006485A1 (en) | 2011-07-01 | 2012-06-29 | Fused benzoxazepinones as ion channel modulators |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015255906A Division JP6273250B2 (ja) | 2011-07-01 | 2015-12-28 | イオンチャネルモジュレーターとしての縮合複素環式化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014522847A JP2014522847A (ja) | 2014-09-08 |
| JP2014522847A5 true JP2014522847A5 (enExample) | 2015-10-15 |
| JP5889407B2 JP5889407B2 (ja) | 2016-03-22 |
Family
ID=46513866
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014519190A Expired - Fee Related JP5889407B2 (ja) | 2011-07-01 | 2012-06-29 | イオンチャネルモジュレーターとしての縮合複素環式化合物 |
| JP2015255906A Expired - Fee Related JP6273250B2 (ja) | 2011-07-01 | 2015-12-28 | イオンチャネルモジュレーターとしての縮合複素環式化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015255906A Expired - Fee Related JP6273250B2 (ja) | 2011-07-01 | 2015-12-28 | イオンチャネルモジュレーターとしての縮合複素環式化合物 |
Country Status (38)
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI625121B (zh) | 2009-07-13 | 2018-06-01 | 基利科學股份有限公司 | 調節細胞凋亡信號之激酶的抑制劑 |
| HUE034911T2 (hu) | 2009-07-27 | 2018-03-28 | Gilead Sciences Inc | Fúzionált heterociklusos vegyületek mint ioncsatorna modulátorok |
| EP2588197B1 (en) | 2010-07-02 | 2014-11-05 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| WO2012154760A1 (en) | 2011-05-10 | 2012-11-15 | Gilead Sciences, Inc. | Fused heterocyclic compounds as sodium channel modulators |
| NO3175985T3 (enExample) | 2011-07-01 | 2018-04-28 | ||
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- 2016-12-15 HK HK16114300.8A patent/HK1226061A1/en unknown
- 2016-12-15 HK HK16114299.1A patent/HK1226060A1/en unknown
-
2018
- 2018-01-08 IL IL256779A patent/IL256779A/en unknown
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