JP2013510122A5 - - Google Patents
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- Publication number
- JP2013510122A5 JP2013510122A5 JP2012537380A JP2012537380A JP2013510122A5 JP 2013510122 A5 JP2013510122 A5 JP 2013510122A5 JP 2012537380 A JP2012537380 A JP 2012537380A JP 2012537380 A JP2012537380 A JP 2012537380A JP 2013510122 A5 JP2013510122 A5 JP 2013510122A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- methyl
- alkyl
- triazolo
- benzodiazepin
- 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.)
- Withdrawn
Links
- 125000000217 alkyl group Chemical group 0.000 claims 33
- -1 nitro, cyano, dimethylamino, benzoyl Chemical group 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000004452 carbocyclyl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- NOXULISRIXJOPU-DTQAZKPQSA-N (e)-3-(4-chlorophenyl)-n-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)prop-2-enamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N2C(C)=NN=C2C1NC(=O)\C=C\C1=CC=C(Cl)C=C1 NOXULISRIXJOPU-DTQAZKPQSA-N 0.000 claims 1
- HQXKNLNBUWKEHU-DTQAZKPQSA-N (e)-3-(4-fluorophenyl)-n-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)prop-2-enamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N2C(C)=NN=C2C1NC(=O)\C=C\C1=CC=C(F)C=C1 HQXKNLNBUWKEHU-DTQAZKPQSA-N 0.000 claims 1
- XOBMKWPZTPKYHP-SAPNQHFASA-N (e)-3-(4-methoxyphenyl)-n-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)prop-2-enamide Chemical compound C1=CC(OC)=CC=C1\C=C\C(=O)NC1C2=NN=C(C)N2C2=CC=CC=C2C(C=2C=CC=CC=2)=N1 XOBMKWPZTPKYHP-SAPNQHFASA-N 0.000 claims 1
- AIBGAEDELSKJMK-UHFFFAOYSA-N 1-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)-3-phenylurea Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N2C(C)=NN=C2C1NC(=O)NC1=CC=CC=C1 AIBGAEDELSKJMK-UHFFFAOYSA-N 0.000 claims 1
- YKHPDEJRXBTLOU-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-3-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)urea Chemical compound C1=CC(OC)=CC=C1CNC(=O)NC1C2=NN=C(C)N2C2=CC=CC=C2C(C=2C=CC=CC=2)=N1 YKHPDEJRXBTLOU-UHFFFAOYSA-N 0.000 claims 1
- RATMGGWUORWQNG-UHFFFAOYSA-N 1-benzyl-3-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)urea Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N2C(C)=NN=C2C1NC(=O)NCC1=CC=CC=C1 RATMGGWUORWQNG-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- NOIUHLVGASAAKC-UHFFFAOYSA-N 3-bromo-n-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)benzamide Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N2C(C)=NN=C2C1NC(=O)C1=CC=CC(Br)=C1 NOIUHLVGASAAKC-UHFFFAOYSA-N 0.000 claims 1
- BOVHWQDJYASZCX-UHFFFAOYSA-N 5-methyl-n-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)-1h-indole-2-carboxamide Chemical compound C12=CC=CC=C2N2C(C)=NN=C2C(NC(=O)C=2NC3=CC=C(C)C=C3C=2)N=C1C1=CC=CC=C1 BOVHWQDJYASZCX-UHFFFAOYSA-N 0.000 claims 1
- AHGSTKPQVCTIHA-UHFFFAOYSA-N 6-methoxy-n-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)-1h-indole-2-carboxamide Chemical compound N1C2=CC(OC)=CC=C2C=C1C(=O)NC(C1=NN=C(C)N1C1=CC=CC=C11)N=C1C1=CC=CC=C1 AHGSTKPQVCTIHA-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical group CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 230000005784 autoimmunity Effects 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- TUWDLUFFAHHNEF-UHFFFAOYSA-N benzyl n-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)carbamate Chemical compound N1=C(C=2C=CC=CC=2)C2=CC=CC=C2N2C(C)=NN=C2C1NC(=O)OCC1=CC=CC=C1 TUWDLUFFAHHNEF-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000006073 displacement reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- YIIAEOSGRYXGSO-UHFFFAOYSA-N ethyl n-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)carbamate Chemical compound C12=CC=CC=C2N2C(C)=NN=C2C(NC(=O)OCC)N=C1C1=CC=CC=C1 YIIAEOSGRYXGSO-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- BOHXEHCCMXOJMM-UHFFFAOYSA-N n-(1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)naphthalene-2-carboxamide Chemical compound C12=CC=CC=C2N2C(C)=NN=C2C(NC(=O)C=2C=C3C=CC=CC3=CC=2)N=C1C1=CC=CC=C1 BOHXEHCCMXOJMM-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0919426.7 | 2009-11-05 | ||
| GBGB0919426.7A GB0919426D0 (en) | 2009-11-05 | 2009-11-05 | Novel compounds |
| PCT/EP2010/066696 WO2011054844A1 (en) | 2009-11-05 | 2010-11-03 | Condensed azepine derivatives as bromodomain inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013510122A JP2013510122A (ja) | 2013-03-21 |
| JP2013510122A5 true JP2013510122A5 (enExample) | 2013-11-28 |
Family
ID=41501969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012537380A Withdrawn JP2013510122A (ja) | 2009-11-05 | 2010-11-03 | ブロモドメイン阻害剤としての縮合アゼピン誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20120202799A1 (enExample) |
| EP (1) | EP2496581A1 (enExample) |
| JP (1) | JP2013510122A (enExample) |
| GB (1) | GB0919426D0 (enExample) |
| WO (1) | WO2011054844A1 (enExample) |
Families Citing this family (75)
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| CN103154246B (zh) | 2010-05-14 | 2015-11-25 | 达那-法伯癌症研究所 | 用于治疗白血病的组合物和方法 |
| ES2606958T3 (es) | 2010-05-14 | 2017-03-28 | Dana-Farber Cancer Institute, Inc. | Compuestos de tienotriazolodiazepina para tratar una neoplasia |
| CN103180318B (zh) | 2010-05-14 | 2017-05-10 | 达那-法伯癌症研究所 | 雄性避孕组合物以及使用方法 |
| AR084070A1 (es) | 2010-12-02 | 2013-04-17 | Constellation Pharmaceuticals Inc | Inhibidores del bromodominio y usos de los mismos |
| WO2012075456A1 (en) | 2010-12-02 | 2012-06-07 | Constellation Pharmaceuticals | Bromodomain inhibitors and uses thereof |
| WO2012151512A2 (en) | 2011-05-04 | 2012-11-08 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| WO2012174487A2 (en) | 2011-06-17 | 2012-12-20 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| WO2013027168A1 (en) | 2011-08-22 | 2013-02-28 | Pfizer Inc. | Novel heterocyclic compounds as bromodomain inhibitors |
| WO2013033268A2 (en) * | 2011-08-29 | 2013-03-07 | Coferon, Inc. | Bivalent bromodomain ligands, and methods of using same |
| WO2013033269A1 (en) * | 2011-08-29 | 2013-03-07 | Coferon, Inc. | Bioorthogonal monomers capable of dimerizing and targeting bromodomains and methods of using same |
| DE102011082013A1 (de) | 2011-09-01 | 2013-03-07 | Bayer Pharma AG | 6H-Thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
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| TWI602820B (zh) | 2012-06-06 | 2017-10-21 | 星宿藥物公司 | 溴域抑制劑及其用途 |
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| EP2970312B1 (en) | 2013-03-11 | 2017-11-15 | The Regents of The University of Michigan | Bet bromodomain inhibitors and therapeutic methods using the same |
| BR112015022391B1 (pt) * | 2013-03-12 | 2021-12-21 | Abbvie Inc | Compostos inibidores do domínio bromo tetracíclico, composição farmacêutica que compreende os referidos compostos e usos terapêuticos dos mesmos |
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| US11446309B2 (en) | 2013-11-08 | 2022-09-20 | Dana-Farber Cancer Institute, Inc. | Combination therapy for cancer using bromodomain and extra-terminal (BET) protein inhibitors |
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| US9315501B2 (en) | 2013-11-26 | 2016-04-19 | Incyte Corporation | Bicyclic heterocycles as BET protein inhibitors |
| US9309246B2 (en) | 2013-12-19 | 2016-04-12 | Incyte Corporation | Tricyclic heterocycles as BET protein inhibitors |
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| US9580430B2 (en) | 2014-02-28 | 2017-02-28 | The Regents Of The University Of Michigan | 9H-pyrimido[4,5-B]indoles and related analogs as BET bromodomain inhibitors |
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| CN106687463B (zh) | 2014-06-20 | 2019-04-09 | 星座制药公司 | 一种乙酰胺类化合物的晶型 |
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| JP6599979B2 (ja) | 2014-09-15 | 2019-10-30 | インサイト・コーポレイション | Ｂｅｔタンパク質阻害剤として用いるための三環式複素環化合物 |
| EP3262045A1 (en) | 2015-02-27 | 2018-01-03 | The Regents of The University of Michigan | 9h-pyrimido [4,5-b]indoles as bet bromodomain inhibitors |
| GB201504694D0 (en) | 2015-03-19 | 2015-05-06 | Glaxosmithkline Ip Dev Ltd | Covalent conjugates |
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| CA2986441A1 (en) | 2015-06-12 | 2016-12-15 | Dana-Farber Cancer Institute, Inc. | Combination therapy of transcription inhibitors and kinase inhibitors |
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| US11306105B2 (en) | 2015-09-11 | 2022-04-19 | Dana-Farber Cancer Institute, Inc. | Cyano thienotriazolodiazepines and uses thereof |
| RU2018112953A (ru) | 2015-09-11 | 2019-10-14 | Дана-Фарбер Кэнсер Инститьют, Инк. | Ацетамидтиенотриазолодиазепины и пути их применения |
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| EP3440082A1 (en) | 2016-04-06 | 2019-02-13 | The Regents of The University of Michigan | Monofunctional intermediates for ligand-dependent target protein degradation |
| AU2017246452C1 (en) | 2016-04-06 | 2021-06-03 | The Regents Of The University Of Michigan | MDM2 protein degraders |
| AU2017250076B2 (en) | 2016-04-12 | 2021-07-22 | The Regents Of The University Of Michigan | Bet protein degraders |
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| CN109715625B (zh) | 2016-06-20 | 2022-04-19 | 因赛特公司 | Bet抑制剂的结晶固体形式 |
| EP3490552B1 (en) | 2016-07-26 | 2022-11-23 | University of Southern California | Selective bromodomain inhibition of fungal bdf1 |
| CA3036834A1 (en) | 2016-09-13 | 2018-03-22 | The Regents Of The University Of Michigan | Fused 1,4-oxazepines as bet protein degraders |
| ES2857743T3 (es) | 2016-09-13 | 2021-09-29 | Univ Michigan Regents | 1,4-diazepinas fusionadas como degradadores de proteína BET |
| EP3577120A1 (en) | 2017-02-03 | 2019-12-11 | The Regents of The University of Michigan | Fused 1,4-diazepines as bet bromodomain inhibitors |
| CN108727380A (zh) * | 2017-04-13 | 2018-11-02 | 中国科学院上海药物研究所 | 一种brd4抑制剂及其制备和应用 |
| EP3638677A1 (en) | 2017-06-16 | 2020-04-22 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
| US11267822B2 (en) | 2017-09-13 | 2022-03-08 | The Regents Of The University Of Michigan | BET bromodomain protein degraders with cleavable linkers |
| EP3774722B1 (en) | 2018-04-04 | 2024-07-24 | Epiodyne, Inc. | Opioid receptor modulators and products and methods related thereto |
| WO2021175432A1 (en) | 2020-03-04 | 2021-09-10 | Boehringer Ingelheim International Gmbh | Method for administration of an anti cancer agent |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| AR122707A1 (es) | 2020-06-23 | 2022-09-28 | Genentech Inc | Compuestos macrocíclicos y métodos de uso de los mismos |
| TW202304869A (zh) | 2021-04-05 | 2023-02-01 | 美商艾碧奧戴股份有限公司 | 類鴉片受體調節劑 |
| US20240316061A1 (en) | 2021-09-17 | 2024-09-26 | Institut Curie | Bet inhibitors for treating pab1 deficient cancer |
| CA3255932A1 (en) | 2022-04-19 | 2023-10-26 | Nuevolution A/S | ACTIVE COMPOUNDS AGAINST BROMODOMAINS |
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| PL330635A1 (en) * | 1996-06-12 | 1999-05-24 | Japan Tobacco Inc | Inhibitor of cytokin production, triazepin compound and intermediate compounds used for obtaining the last mentioned one |
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-
2009
- 2009-11-05 GB GBGB0919426.7A patent/GB0919426D0/en not_active Ceased
-
2010
- 2010-11-03 EP EP10773086A patent/EP2496581A1/en not_active Withdrawn
- 2010-11-03 WO PCT/EP2010/066696 patent/WO2011054844A1/en not_active Ceased
- 2010-11-03 JP JP2012537380A patent/JP2013510122A/ja not_active Withdrawn
- 2010-11-03 US US13/501,557 patent/US20120202799A1/en not_active Abandoned
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