TWI537266B - 充當離子通道調節劑的稠合雜環化合物 - Google Patents
充當離子通道調節劑的稠合雜環化合物 Download PDFInfo
- Publication number
- TWI537266B TWI537266B TW100123352A TW100123352A TWI537266B TW I537266 B TWI537266 B TW I537266B TW 100123352 A TW100123352 A TW 100123352A TW 100123352 A TW100123352 A TW 100123352A TW I537266 B TWI537266 B TW I537266B
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- Taiwan
- Prior art keywords
- group
- pyridine
- phenyl
- triazolo
- trifluoromethoxy
- Prior art date
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- 102000004310 Ion Channels Human genes 0.000 title 1
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 430
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 371
- 125000003118 aryl group Chemical group 0.000 claims description 358
- 125000001072 heteroaryl group Chemical group 0.000 claims description 313
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 292
- 125000001424 substituent group Chemical group 0.000 claims description 278
- 125000000623 heterocyclic group Chemical group 0.000 claims description 265
- 125000003545 alkoxy group Chemical group 0.000 claims description 264
- 125000000217 alkyl group Chemical group 0.000 claims description 257
- 150000001875 compounds Chemical class 0.000 claims description 248
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 227
- 125000005843 halogen group Chemical group 0.000 claims description 210
- 125000003342 alkenyl group Chemical group 0.000 claims description 133
- 229910052739 hydrogen Inorganic materials 0.000 claims description 112
- 239000001257 hydrogen Substances 0.000 claims description 112
- 239000011734 sodium Substances 0.000 claims description 111
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 100
- -1 -CF 3 Chemical group 0.000 claims description 99
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 97
- 150000002431 hydrogen Chemical class 0.000 claims description 84
- 125000000304 alkynyl group Chemical group 0.000 claims description 81
- 150000001412 amines Chemical class 0.000 claims description 56
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 47
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 46
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 45
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 201000010099 disease Diseases 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 206010002383 Angina Pectoris Diseases 0.000 claims description 16
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims description 15
- 206010019280 Heart failures Diseases 0.000 claims description 15
- WCKSPUOMUKLNAH-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)NN=C2C=C1 WCKSPUOMUKLNAH-UHFFFAOYSA-N 0.000 claims description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 13
- LJRXNXBFJXXRNQ-UHFFFAOYSA-N 2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC=CN2C(=O)NN=C21 LJRXNXBFJXXRNQ-UHFFFAOYSA-N 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 11
- 208000028867 ischemia Diseases 0.000 claims description 11
- 150000002576 ketones Chemical class 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 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 8
- 241000124008 Mammalia Species 0.000 claims description 8
- 208000007814 Unstable Angina Diseases 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- FHOXTMMDQPXGEB-UHFFFAOYSA-N 6-[4-(trifluoromethyl)phenyl]-2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN2C(=O)NN=C2C=C1 FHOXTMMDQPXGEB-UHFFFAOYSA-N 0.000 claims description 7
- 206010002388 Angina unstable Diseases 0.000 claims description 7
- 206010022562 Intermittent claudication Diseases 0.000 claims description 7
- 208000007718 Stable Angina Diseases 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 7
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 7
- 208000010125 myocardial infarction Diseases 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- UUEZDKYARYKPTK-UHFFFAOYSA-N 2-[2-(4-cyclopropylpyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=C(C=CN=3)C3CC3)N=C2C=C1 UUEZDKYARYKPTK-UHFFFAOYSA-N 0.000 claims description 6
- 200000000007 Arterial disease Diseases 0.000 claims description 6
- 208000003037 Diastolic Heart Failure Diseases 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 6
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 6
- VECCJOMKYSSSIJ-UHFFFAOYSA-N 2-(2-pyridin-2-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3N=CC=CC=3)N=C2C=C1 VECCJOMKYSSSIJ-UHFFFAOYSA-N 0.000 claims description 5
- BCMKIAFOKMLLCY-UHFFFAOYSA-N 2-(2-pyrimidin-4-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3N=CN=CC=3)N=C2C=C1 BCMKIAFOKMLLCY-UHFFFAOYSA-N 0.000 claims description 5
- RRAJQAYXEXKFHG-UHFFFAOYSA-N 2-[(5-cyclopropyl-2-methylpyrazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CN1N=C(C2CC2)C=C1CN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 RRAJQAYXEXKFHG-UHFFFAOYSA-N 0.000 claims description 5
- RVEZVRQDJRMSLZ-UHFFFAOYSA-N 2-[2-(3-methylpyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=CC=CN=C1CCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 RVEZVRQDJRMSLZ-UHFFFAOYSA-N 0.000 claims description 5
- IDVVEYCFEYNEGJ-UHFFFAOYSA-N 2-[2-[4-(dimethylamino)-5-fluoropyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(F)C(N(C)C)=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 IDVVEYCFEYNEGJ-UHFFFAOYSA-N 0.000 claims description 5
- CKSVRMWEVBWXQA-UHFFFAOYSA-N 2-[3-(2-chlorophenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCOC=3C(=CC=CC=3)Cl)N=C2C=C1 CKSVRMWEVBWXQA-UHFFFAOYSA-N 0.000 claims description 5
- LOZNQJGOYFAIMZ-UHFFFAOYSA-N 2-[3-(4,5-dichloro-2-methoxyphenoxy)-2-hydroxypropyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC(Cl)=C(Cl)C=C1OCC(O)CN1C(=O)N2C=C(C=3C=CC(=CC=3)C(F)(F)F)C=CC2=N1 LOZNQJGOYFAIMZ-UHFFFAOYSA-N 0.000 claims description 5
- KETWVEPWCQNJBR-UHFFFAOYSA-N 2-methyl-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1N2C(=O)N(C)N=C2C=CC=1C1=CC=C(C(F)(F)F)C=C1 KETWVEPWCQNJBR-UHFFFAOYSA-N 0.000 claims description 5
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- 230000000306 recurrent effect Effects 0.000 claims description 5
- OVXHQIODPLLPGS-UHFFFAOYSA-N 2-(2-hydroxy-3-phenoxypropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(O)COC1=CC=CC=C1 OVXHQIODPLLPGS-UHFFFAOYSA-N 0.000 claims description 4
- BULIWKSBFXZAGF-UHFFFAOYSA-N 2-(2-pyridin-2-ylpropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1C=CC=NC=1C(C)CN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 BULIWKSBFXZAGF-UHFFFAOYSA-N 0.000 claims description 4
- HCIVEOQQCFYJPE-UHFFFAOYSA-N 2-(2-pyrimidin-2-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3N=CC=CN=3)N=C2C=C1 HCIVEOQQCFYJPE-UHFFFAOYSA-N 0.000 claims description 4
- JPBBULQEKZVHQV-UHFFFAOYSA-N 2-(3-phenoxypropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCOC=3C=CC=CC=3)N=C2C=C1 JPBBULQEKZVHQV-UHFFFAOYSA-N 0.000 claims description 4
- YWPYCDLKADHMCQ-GOSISDBHSA-N 2-[(2r)-3-(2-chlorophenoxy)-2-methoxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C([C@H](OC)CN1C(N2C=C(C=CC2=N1)C=1C=CC(OC(F)(F)F)=CC=1)=O)OC1=CC=CC=C1Cl YWPYCDLKADHMCQ-GOSISDBHSA-N 0.000 claims description 4
- YFLRCGNFZGDKJZ-KRWDZBQOSA-N 2-[(2s)-3-methoxy-2-[3-(trifluoromethyl)pyridin-2-yl]oxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C([C@@H](COC)OC=1C(=CC=CN=1)C(F)(F)F)N(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 YFLRCGNFZGDKJZ-KRWDZBQOSA-N 0.000 claims description 4
- LROYJVODHXKYIJ-UHFFFAOYSA-N 2-[2-(2-chlorophenoxy)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C(=CC=CC=3)Cl)N=C2C=C1 LROYJVODHXKYIJ-UHFFFAOYSA-N 0.000 claims description 4
- LCYDBKHIAPRFCQ-UHFFFAOYSA-N 2-[2-(3-chlorophenoxy)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C=C(Cl)C=CC=3)N=C2C=C1 LCYDBKHIAPRFCQ-UHFFFAOYSA-N 0.000 claims description 4
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- HCNSGWVLGRSJRT-UHFFFAOYSA-N 2-[2-(3-phenoxypyrrolidin-1-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCN3CC(CC3)OC=3C=CC=CC=3)N=C2C=C1 HCNSGWVLGRSJRT-UHFFFAOYSA-N 0.000 claims description 4
- WIJCIFKHSGPZJO-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C=CC(Cl)=CC=3)N=C2C=C1 WIJCIFKHSGPZJO-UHFFFAOYSA-N 0.000 claims description 4
- BIDPHMBOBGPSFW-UHFFFAOYSA-N 2-[2-(4-chloropyrazol-1-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCN3N=CC(Cl)=C3)N=C2C=C1 BIDPHMBOBGPSFW-UHFFFAOYSA-N 0.000 claims description 4
- PQXDNFUGLLOROY-UHFFFAOYSA-N 2-[2-(4-ethoxypyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CCOC1=CC=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 PQXDNFUGLLOROY-UHFFFAOYSA-N 0.000 claims description 4
- GCNDSKRXUCBSLW-UHFFFAOYSA-N 2-[2-(4-methylpyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=CC=NC(CCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=C1 GCNDSKRXUCBSLW-UHFFFAOYSA-N 0.000 claims description 4
- GJCXAVXCYWJLBZ-UHFFFAOYSA-N 2-[2-(4-phenylpyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=C(C=CN=3)C=3C=CC=CC=3)N=C2C=C1 GJCXAVXCYWJLBZ-UHFFFAOYSA-N 0.000 claims description 4
- GUKRGCNHZGAJRU-UHFFFAOYSA-N 2-[2-(5-methoxypyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=CC(OC)=CN=C1OCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 GUKRGCNHZGAJRU-UHFFFAOYSA-N 0.000 claims description 4
- FDGAKDDEXYYGQQ-UHFFFAOYSA-N 2-[2-(6-methylpyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=CC=CC(CCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 FDGAKDDEXYYGQQ-UHFFFAOYSA-N 0.000 claims description 4
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- GPVLBTKDPJWJQG-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2-[3-[2-(trifluoromethyl)phenoxy]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCOC=3C(=CC=CC=3)C(F)(F)F)N=C2C=C1 GPVLBTKDPJWJQG-UHFFFAOYSA-N 0.000 claims description 4
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- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
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Classifications
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| US36105610P | 2010-07-02 | 2010-07-02 |
Publications (2)
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| TWI537266B true TWI537266B (zh) | 2016-06-11 |
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| US8952034B2 (en) | 2009-07-27 | 2015-02-10 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| EA026385B9 (ru) | 2010-07-02 | 2017-08-31 | Джилид Сайэнс, Инк. | Конденсированные гетероциклические соединения в качестве модуляторов ионных каналов |
| CN105693645B (zh) | 2011-05-10 | 2018-10-09 | 吉利德科学公司 | 作为离子通道调节剂的稠合杂环化合物 |
| TWI549944B (zh) | 2011-07-01 | 2016-09-21 | 吉李德科學股份有限公司 | 作為離子通道調節劑之稠合雜環化合物 |
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| US9266881B2 (en) * | 2011-11-14 | 2016-02-23 | Merck Sharp & Dohme Corp. | Triazolopyridinone PDE10 inhibitors |
| WO2013112932A1 (en) | 2012-01-27 | 2013-08-01 | Gilead Sciences, Inc. | Combination therapies using late sodium ion channel blockers and potassium ion channel blockers |
| BR112015022488A2 (pt) * | 2013-03-14 | 2017-07-18 | Genentech Inc | triazolopiridinas substituídas e métodos de uso das mesmas |
| US9493442B2 (en) | 2014-02-13 | 2016-11-15 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| KR102421235B1 (ko) | 2014-02-13 | 2022-07-15 | 인사이트 코포레이션 | Lsd1 저해제로서 사이클로프로필아민 |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| TWI720451B (zh) | 2014-02-13 | 2021-03-01 | 美商英塞特控股公司 | 作為lsd1抑制劑之環丙胺 |
| KR102495840B1 (ko) * | 2014-06-17 | 2023-02-03 | 치아타이 티안큉 파마수티컬 그룹 주식회사 | PI3K 억제제로 사용되는 피리디노[1,2-a]피리미돈 유사체 |
| US9758523B2 (en) | 2014-07-10 | 2017-09-12 | Incyte Corporation | Triazolopyridines and triazolopyrazines as LSD1 inhibitors |
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| AU2011272787B2 (en) | 2015-06-18 |
| ES2529119T3 (es) | 2015-02-17 |
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| US20150080370A1 (en) | 2015-03-19 |
| PT2588197E (pt) | 2015-02-09 |
| EA026385B9 (ru) | 2017-08-31 |
| EP2588197A1 (en) | 2013-05-08 |
| AU2011272787A1 (en) | 2013-01-10 |
| EA026385B1 (ru) | 2017-04-28 |
| EA201291272A1 (ru) | 2013-12-30 |
| CA2802288C (en) | 2018-08-21 |
| US9079901B2 (en) | 2015-07-14 |
| TW201215608A (en) | 2012-04-16 |
| BR112012033402A2 (pt) | 2017-01-24 |
| CN103096977B (zh) | 2017-02-15 |
| JP5858586B2 (ja) | 2016-02-10 |
| EP2588197B1 (en) | 2014-11-05 |
| HK1184092A1 (en) | 2014-01-17 |
| NZ604478A (en) | 2014-12-24 |
| JP2013535423A (ja) | 2013-09-12 |
| CN103096977A (zh) | 2013-05-08 |
| MX2012015096A (es) | 2013-05-28 |
| WO2012003392A1 (en) | 2012-01-05 |
| JP2016029107A (ja) | 2016-03-03 |
| US8703759B2 (en) | 2014-04-22 |
| CA2802288A1 (en) | 2012-01-05 |
| KR20130043158A (ko) | 2013-04-29 |
| KR101911560B1 (ko) | 2018-10-24 |
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