JP2016501254A5 - - Google Patents
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- Publication number
- JP2016501254A5 JP2016501254A5 JP2015546026A JP2015546026A JP2016501254A5 JP 2016501254 A5 JP2016501254 A5 JP 2016501254A5 JP 2015546026 A JP2015546026 A JP 2015546026A JP 2015546026 A JP2015546026 A JP 2015546026A JP 2016501254 A5 JP2016501254 A5 JP 2016501254A5
- Authority
- JP
- Japan
- Prior art keywords
- indol
- acrylonitrile
- bromo
- pyridin
- chloro
- 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
- 150000001875 compounds Chemical class 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical group 0.000 claims 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- -1 5-chloro-1H-indol-3-yl Chemical group 0.000 claims 9
- 206010028980 Neoplasm Diseases 0.000 claims 9
- 201000011510 cancer Diseases 0.000 claims 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 208000019693 Lung disease Diseases 0.000 claims 3
- 208000036142 Viral infection Diseases 0.000 claims 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 229940041181 antineoplastic drug Drugs 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 230000009385 viral infection Effects 0.000 claims 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 102100037694 Kinesin-like protein KIF20A Human genes 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 230000008685 targeting Effects 0.000 claims 2
- 125000005000 thioaryl group Chemical group 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- BYIJBBWWVRHOKH-MDWZMJQESA-N (z)-3-(4-ethoxypyridin-3-yl)-2-(5-methoxy-1h-indol-3-yl)prop-2-enenitrile Chemical compound CCOC1=CC=NC=C1\C=C(/C#N)C1=CNC2=CC=C(OC)C=C12 BYIJBBWWVRHOKH-MDWZMJQESA-N 0.000 claims 1
- OVQIIIWKDPJWGD-UHFFFAOYSA-N 2-(4-fluorophenoxy)benzonitrile Chemical compound C1=CC(F)=CC=C1OC1=CC=CC=C1C#N OVQIIIWKDPJWGD-UHFFFAOYSA-N 0.000 claims 1
- OTNOMEKVRRGLFG-UHFFFAOYSA-N 2-[2-(5-bromo-1h-indol-3-yl)-2-cyanoethenyl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C(C=C(C#N)C=2C3=CC(Br)=CC=C3NC=2)=C1 OTNOMEKVRRGLFG-UHFFFAOYSA-N 0.000 claims 1
- 102000003915 DNA Topoisomerases Human genes 0.000 claims 1
- 108090000323 DNA Topoisomerases Proteins 0.000 claims 1
- 239000012624 DNA alkylating agent Substances 0.000 claims 1
- 229940126161 DNA alkylating agent Drugs 0.000 claims 1
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 208000037357 HIV infectious disease Diseases 0.000 claims 1
- 241000598436 Human T-cell lymphotropic virus Species 0.000 claims 1
- 206010020843 Hyperthermia Diseases 0.000 claims 1
- 229940121849 Mitotic inhibitor Drugs 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 208000009608 Papillomavirus Infections Diseases 0.000 claims 1
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 1
- 102000007537 Type II DNA Topoisomerases Human genes 0.000 claims 1
- 108010046308 Type II DNA Topoisomerases Proteins 0.000 claims 1
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 230000008827 biological function Effects 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 230000003013 cytotoxicity Effects 0.000 claims 1
- 231100000135 cytotoxicity Toxicity 0.000 claims 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical group [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000008482 dysregulation Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000036031 hyperthermia Effects 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261734451P | 2012-12-07 | 2012-12-07 | |
| US61/734,451 | 2012-12-07 | ||
| EP12306536.9 | 2012-12-07 | ||
| EP12306536 | 2012-12-07 | ||
| EP13157372 | 2013-03-01 | ||
| EP13157372.7 | 2013-03-01 | ||
| PCT/EP2013/075776 WO2014086964A1 (en) | 2012-12-07 | 2013-12-06 | New derivatives of indole for the treatment of cancer, viral infections and lung diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016501254A JP2016501254A (ja) | 2016-01-18 |
| JP2016501254A5 true JP2016501254A5 (enExample) | 2017-11-16 |
| JP6250062B2 JP6250062B2 (ja) | 2017-12-20 |
Family
ID=50882829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015546026A Active JP6250062B2 (ja) | 2012-12-07 | 2013-12-06 | がん、ウイルス感染症、及び肺疾患の処置のためのインドールの新規誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US9643923B2 (enExample) |
| EP (1) | EP2928864B1 (enExample) |
| JP (1) | JP6250062B2 (enExample) |
| KR (1) | KR102169940B1 (enExample) |
| CN (2) | CN108341799B (enExample) |
| CA (1) | CA2891900C (enExample) |
| IL (1) | IL238722B (enExample) |
| PL (1) | PL2928864T3 (enExample) |
| WO (1) | WO2014086964A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2928864B1 (en) | 2012-12-07 | 2020-01-15 | Biokinesis | New derivatives of indole for the treatment of cancer, viral infections and lung diseases |
| JP7130180B2 (ja) * | 2016-10-24 | 2022-09-05 | ディアキュレイト | 子宮内膜症の処置のためのインドールの新規誘導体 |
| US20220213099A1 (en) * | 2019-05-07 | 2022-07-07 | Bristol-Myers Squibb Company | Prodrug compounds |
| WO2024003002A1 (en) | 2022-06-27 | 2024-01-04 | Diaccurate | N-substituted indole derivatives and conjugates for the treatment of cancer |
| US20260199308A1 (en) | 2022-12-05 | 2026-07-16 | Centre National De La Recherche Scientifique | Derivatives of indole for the treatment of cancer |
| JP2025539491A (ja) | 2022-12-16 | 2025-12-05 | イヴクスタ・バイオ | （ｚ）－３－（２－（５－ブロモ－１ｈ－インドール－３－イル）－２－シアノビニル）－４－メトキシベンゾニトリルを調製する方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002500190A (ja) | 1998-01-08 | 2002-01-08 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 海洋海綿から誘導されるキネシンモーターモジュレーター |
| JP2000336075A (ja) * | 1999-05-26 | 2000-12-05 | Sankyo Co Ltd | アクリロニトリル誘導体 |
| US6890933B1 (en) | 2000-02-24 | 2005-05-10 | President And Fellows Of Harvard College | Kinesin inhibitors |
| US6335342B1 (en) * | 2000-06-19 | 2002-01-01 | Pharmacia & Upjohn S.P.A. | Azaindole derivatives, process for their preparation, and their use as antitumor agents |
| US7361764B2 (en) | 2004-07-27 | 2008-04-22 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
| CN101027302B (zh) * | 2004-07-27 | 2011-05-11 | Sgx药物公司 | 吡咯并吡啶激酶调节剂 |
| EP2266562A1 (en) * | 2009-06-23 | 2010-12-29 | Centre National de la Recherche Scientifique | Use of derivatives of indoles for the treatment of cancer |
| WO2012009097A1 (en) | 2010-06-17 | 2012-01-19 | Cytokinetics, Inc. | Methods of treating lung disease |
| EP2455456A1 (en) | 2010-11-22 | 2012-05-23 | Institut Curie | Use of kinesin inhibitors in HIV infection treatment and a method for screening them |
| EP2928864B1 (en) | 2012-12-07 | 2020-01-15 | Biokinesis | New derivatives of indole for the treatment of cancer, viral infections and lung diseases |
| JP7130180B2 (ja) | 2016-10-24 | 2022-09-05 | ディアキュレイト | 子宮内膜症の処置のためのインドールの新規誘導体 |
-
2013
- 2013-12-06 EP EP13802038.3A patent/EP2928864B1/en active Active
- 2013-12-06 PL PL13802038T patent/PL2928864T3/pl unknown
- 2013-12-06 CA CA2891900A patent/CA2891900C/en active Active
- 2013-12-06 US US14/647,521 patent/US9643923B2/en active Active
- 2013-12-06 KR KR1020157018178A patent/KR102169940B1/ko active Active
- 2013-12-06 WO PCT/EP2013/075776 patent/WO2014086964A1/en not_active Ceased
- 2013-12-06 CN CN201810021544.4A patent/CN108341799B/zh active Active
- 2013-12-06 CN CN201380063540.8A patent/CN104854088B/zh active Active
- 2013-12-06 JP JP2015546026A patent/JP6250062B2/ja active Active
-
2015
- 2015-05-10 IL IL238722A patent/IL238722B/en active IP Right Grant
-
2017
- 2017-05-04 US US15/586,343 patent/US10189782B2/en active Active
-
2019
- 2019-01-25 US US16/257,096 patent/US10851054B2/en active Active
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