JP2016520537A5 - - Google Patents
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- Publication number
- JP2016520537A5 JP2016520537A5 JP2016504633A JP2016504633A JP2016520537A5 JP 2016520537 A5 JP2016520537 A5 JP 2016520537A5 JP 2016504633 A JP2016504633 A JP 2016504633A JP 2016504633 A JP2016504633 A JP 2016504633A JP 2016520537 A5 JP2016520537 A5 JP 2016520537A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- heterocycle
- alkenyl
- alkynyl
- aryl
- 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 1759
- 125000003118 aryl group Chemical group 0.000 claims description 551
- 125000000623 heterocyclic group Chemical group 0.000 claims description 491
- 125000000304 alkynyl group Chemical group 0.000 claims description 465
- 125000003342 alkenyl group Chemical group 0.000 claims description 434
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 354
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 315
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 315
- 229910052736 halogen Inorganic materials 0.000 claims description 314
- 150000002367 halogens Chemical class 0.000 claims description 314
- -1 cycloalkynyl Chemical group 0.000 claims description 277
- 125000005842 heteroatom Chemical group 0.000 claims description 258
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 238
- 229910052739 hydrogen Inorganic materials 0.000 claims description 237
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 232
- 125000001424 substituent group Chemical group 0.000 claims description 231
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 224
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 223
- 239000001257 hydrogen Substances 0.000 claims description 210
- 150000002431 hydrogen Chemical class 0.000 claims description 165
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 162
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 161
- 150000001875 compounds Chemical class 0.000 claims description 127
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 102
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 85
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 82
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 82
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 82
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 78
- 229910052799 carbon Inorganic materials 0.000 claims description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
- 229910052760 oxygen Inorganic materials 0.000 claims description 44
- 229910052717 sulfur Inorganic materials 0.000 claims description 44
- JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical compound [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 39
- 239000008194 pharmaceutical composition Substances 0.000 claims description 28
- 125000002757 morpholinyl group Chemical group 0.000 claims description 25
- 125000003386 piperidinyl group Chemical group 0.000 claims description 25
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 24
- 125000004193 piperazinyl group Chemical group 0.000 claims description 24
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 24
- 208000015181 infectious disease Diseases 0.000 claims description 23
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
- 241000725619 Dengue virus Species 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 16
- 206010054261 Flavivirus infection Diseases 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 229940002612 prodrug Drugs 0.000 claims description 15
- 239000000651 prodrug Substances 0.000 claims description 15
- 241000282412 Homo Species 0.000 claims description 14
- 241001465754 Metazoa Species 0.000 claims description 13
- 241000710772 Yellow fever virus Species 0.000 claims description 12
- 229940051021 yellow-fever virus Drugs 0.000 claims description 12
- 229910005965 SO 2 Inorganic materials 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 230000002265 prevention Effects 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- BPUYNABLDRBCTQ-UHFFFAOYSA-N 2-anilino-1-(2-phenylpiperidin-1-yl)-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C(C(=O)N1C(CCCC1)C=1C=CC=CC=1)NC1=CC=CC=C1 BPUYNABLDRBCTQ-UHFFFAOYSA-N 0.000 claims description 3
- ITCHPTBCVOHEJI-UHFFFAOYSA-N 2-anilino-2-(4-tert-butylphenyl)-1-(2-phenylazepan-1-yl)ethanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C(=O)N1C(CCCCC1)C=1C=CC=CC=1)NC1=CC=CC=C1 ITCHPTBCVOHEJI-UHFFFAOYSA-N 0.000 claims description 3
- MPZVGBLBUFENCC-UHFFFAOYSA-N 2-anilino-2-(4-tert-butylphenyl)-1-(2-phenylpiperidin-1-yl)ethanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C(=O)N1C(CCCC1)C=1C=CC=CC=1)NC1=CC=CC=C1 MPZVGBLBUFENCC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 241000907681 Morpho Species 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical group O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229920000728 polyester Polymers 0.000 description 159
- 238000000034 method Methods 0.000 description 23
- 206010012310 Dengue fever Diseases 0.000 description 15
- 208000036142 Viral infection Diseases 0.000 description 12
- 230000009385 viral infection Effects 0.000 description 12
- 208000025729 dengue disease Diseases 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 208000001490 Dengue Diseases 0.000 description 9
- 208000009714 Severe Dengue Diseases 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 241000700605 Viruses Species 0.000 description 8
- 241000710831 Flavivirus Species 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 241000255925 Diptera Species 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 201000002950 dengue hemorrhagic fever Diseases 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000002541 furyl group Chemical group 0.000 description 5
- 125000000842 isoxazolyl group Chemical group 0.000 description 5
- 239000008177 pharmaceutical agent Substances 0.000 description 5
- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- 241000710781 Flaviviridae Species 0.000 description 4
- 241000282414 Homo sapiens Species 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 4
- 241000710829 Dengue virus group Species 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- 229960005486 vaccine Drugs 0.000 description 3
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 208000003322 Coinfection Diseases 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- 241000256173 Aedes albopictus Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 206010061192 Haemorrhagic fever Diseases 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 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 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 201000009892 dengue shock syndrome Diseases 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000008774 maternal effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 229940031351 tetravalent vaccine Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361805054P | 2013-03-25 | 2013-03-25 | |
| GB1305376.4 | 2013-03-25 | ||
| US61/805,054 | 2013-03-25 | ||
| GB201305376A GB201305376D0 (en) | 2013-03-25 | 2013-03-25 | Novel viral replication inhibitors |
| PCT/EP2014/055946 WO2014154682A1 (en) | 2013-03-25 | 2014-03-25 | Novel viral replication inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016520537A JP2016520537A (ja) | 2016-07-14 |
| JP2016520537A5 true JP2016520537A5 (enExample) | 2017-04-27 |
| JP6382299B2 JP6382299B2 (ja) | 2018-08-29 |
Family
ID=48326577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016504633A Active JP6382299B2 (ja) | 2013-03-25 | 2014-03-25 | 新規のウイルス複製阻害剤 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US10633378B2 (enExample) |
| EP (1) | EP2978753B1 (enExample) |
| JP (1) | JP6382299B2 (enExample) |
| CN (1) | CN105283451B (enExample) |
| AU (2) | AU2014243101B2 (enExample) |
| BR (1) | BR112015024552B1 (enExample) |
| CA (1) | CA2907603C (enExample) |
| ES (1) | ES2829907T3 (enExample) |
| GB (1) | GB201305376D0 (enExample) |
| MX (1) | MX365624B (enExample) |
| MY (1) | MY194294A (enExample) |
| PH (1) | PH12015502230B1 (enExample) |
| SG (2) | SG10201707033PA (enExample) |
| TW (1) | TWI639583B (enExample) |
| WO (1) | WO2014154682A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201116559D0 (en) | 2011-09-26 | 2011-11-09 | Univ Leuven Kath | Novel viral replication inhibitors |
| GB201305376D0 (en) | 2013-03-25 | 2013-05-08 | Univ Leuven Kath | Novel viral replication inhibitors |
| JOP20160086B1 (ar) | 2015-05-08 | 2021-08-17 | 2 Katholieke Univ Leuven Ku Leuven Research And Development | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20160198B1 (ar) | 2015-09-16 | 2022-03-14 | Janssen Pharmaceuticals Inc | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JO3633B1 (ar) | 2015-09-16 | 2020-08-27 | Katholieke Univ Leuven Ku Leuven Research & Development | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| CA3013407A1 (en) | 2016-03-31 | 2017-10-05 | Janssen Pharmaceuticals, Inc. | Substituted indoline derivatives as dengue viral replication inhibitors |
| AU2017242893A1 (en) | 2016-03-31 | 2018-08-09 | Janssen Pharmaceuticals, Inc. | Substituted indole derivatives as dengue viral replication inhibitors |
| KR102359766B1 (ko) | 2016-04-01 | 2022-02-07 | 얀센 파마슈티칼즈, 인코포레이티드 | 뎅기 바이러스 복제 억제제로서 치환된 인돌 화합물 유도체 |
| JOP20170069B1 (ar) * | 2016-04-01 | 2021-08-17 | 1 Janssen Pharmaceuticals Inc | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20180025B1 (ar) * | 2017-03-31 | 2021-08-17 | Janssen Pharmaceuticals Inc | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20180026A1 (ar) | 2017-03-31 | 2019-01-30 | Univ Leuven Kath | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JP7203764B2 (ja) * | 2017-05-22 | 2023-01-13 | ヤンセン ファーマシューティカルズ，インコーポレーテッド | デングウイルス複製阻害剤としての置換インドリン誘導体 |
| DK3630724T3 (da) * | 2017-05-22 | 2021-07-26 | Janssen Pharmaceuticals Inc | Substituerede indolinderivater som inhibitorer af virusreplikation af denguevirus |
| WO2023283256A1 (en) | 2021-07-09 | 2023-01-12 | Aligos Therapeutics, Inc. | Anti-viral compounds |
| WO2023043816A1 (en) * | 2021-09-17 | 2023-03-23 | Aligos Therapeutics, Inc. | Anti-viral compounds for treating coronavirus, picornavirus, and norovirus infections |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| TW200524575A (en) | 2003-10-27 | 2005-08-01 | S Bio Pte Ltd | Biaryl linked hydroxamates: preparation and pharmaceutical applications |
| KR20090082221A (ko) * | 2006-10-19 | 2009-07-29 | 노파르티스 아게 | 유기 화합물 |
| ES2612731T3 (es) | 2008-08-19 | 2017-05-18 | Janssen Pharmaceutica Nv | Antagonistas de receptores al frío de mentol |
| TWI453207B (zh) | 2008-09-08 | 2014-09-21 | Signal Pharm Llc | 胺基三唑并吡啶，其組合物及使用其之治療方法 |
| WO2010062821A1 (en) | 2008-11-28 | 2010-06-03 | Glaxosmithkline Llc | Anti-viral compounds, compositions, and methods of use |
| WO2010094977A1 (en) * | 2009-02-23 | 2010-08-26 | Arrow Therapeutics Limited | Novel biphenyl compounds useful for the treatment of hepatitis c |
| CA2753313A1 (en) * | 2009-02-23 | 2010-08-26 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| CN102612651A (zh) * | 2009-09-18 | 2012-07-25 | 诺瓦提斯公司 | Iap抑制剂化合物的生物标志物 |
| MX2012006026A (es) * | 2009-11-25 | 2012-08-15 | Vertex Pharma | Derivados de acido 5-alquinil-tiofen-2-carboxilico y usos para tratamiento o prevencion de infecciones por flavivirus. |
| CN102552271B (zh) * | 2010-12-09 | 2014-08-06 | 中国科学院上海药物研究所 | 一类喹唑啉类化合物在制备抗黄病毒科病毒的药物中的用途 |
| GB201116559D0 (en) | 2011-09-26 | 2011-11-09 | Univ Leuven Kath | Novel viral replication inhibitors |
| GB201305376D0 (en) | 2013-03-25 | 2013-05-08 | Univ Leuven Kath | Novel viral replication inhibitors |
| KR102478311B1 (ko) | 2014-10-01 | 2022-12-15 | 얀센 파마슈티칼즈, 인코포레이티드 | 뎅기 바이러스 복제 억제제로서의 １치환 또는 ２치환 인돌 유도체 |
| PH12017501272B1 (en) | 2015-01-16 | 2023-01-11 | Janssen Pharmaceuticals Inc | Indole derivatives as dengue viral replication inhibitors |
| JOP20160086B1 (ar) | 2015-05-08 | 2021-08-17 | 2 Katholieke Univ Leuven Ku Leuven Research And Development | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JO3633B1 (ar) | 2015-09-16 | 2020-08-27 | Katholieke Univ Leuven Ku Leuven Research & Development | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20160198B1 (ar) | 2015-09-16 | 2022-03-14 | Janssen Pharmaceuticals Inc | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| AU2017242893A1 (en) | 2016-03-31 | 2018-08-09 | Janssen Pharmaceuticals, Inc. | Substituted indole derivatives as dengue viral replication inhibitors |
| CA3013407A1 (en) | 2016-03-31 | 2017-10-05 | Janssen Pharmaceuticals, Inc. | Substituted indoline derivatives as dengue viral replication inhibitors |
| JOP20170069B1 (ar) | 2016-04-01 | 2021-08-17 | 1 Janssen Pharmaceuticals Inc | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| KR102359766B1 (ko) | 2016-04-01 | 2022-02-07 | 얀센 파마슈티칼즈, 인코포레이티드 | 뎅기 바이러스 복제 억제제로서 치환된 인돌 화합물 유도체 |
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2013
- 2013-03-25 GB GB201305376A patent/GB201305376D0/en not_active Ceased
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2014
- 2014-03-25 SG SG10201707033PA patent/SG10201707033PA/en unknown
- 2014-03-25 US US14/777,765 patent/US10633378B2/en active Active
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- 2014-03-25 MY MYPI2015002431A patent/MY194294A/en unknown
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- 2014-03-25 WO PCT/EP2014/055946 patent/WO2014154682A1/en not_active Ceased
- 2014-03-25 ES ES14718338T patent/ES2829907T3/es active Active
- 2014-03-25 BR BR112015024552-8A patent/BR112015024552B1/pt active IP Right Grant
- 2014-03-25 CN CN201480023957.6A patent/CN105283451B/zh active Active
- 2014-03-25 JP JP2016504633A patent/JP6382299B2/ja active Active
- 2014-03-25 AU AU2014243101A patent/AU2014243101B2/en active Active
- 2014-03-25 TW TW103111110A patent/TWI639583B/zh not_active IP Right Cessation
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2015
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2018
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2020
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