JP2014518870A5 - - Google Patents
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- Publication number
- JP2014518870A5 JP2014518870A5 JP2014510933A JP2014510933A JP2014518870A5 JP 2014518870 A5 JP2014518870 A5 JP 2014518870A5 JP 2014510933 A JP2014510933 A JP 2014510933A JP 2014510933 A JP2014510933 A JP 2014510933A JP 2014518870 A5 JP2014518870 A5 JP 2014518870A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl
- pharmaceutically acceptable
- acceptable salt
- phosphate
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 19
- -1 oct-7-yl Chemical group 0.000 claims description 18
- 229910019142 PO4 Inorganic materials 0.000 claims description 16
- 239000010452 phosphate Substances 0.000 claims description 16
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- YEWZQCDRZRYAEB-UHFFFAOYSA-M ditert-butyl phosphate Chemical compound CC(C)(C)OP([O-])(=O)OC(C)(C)C YEWZQCDRZRYAEB-UHFFFAOYSA-M 0.000 claims description 6
- 239000012467 final product Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 230000004761 fibrosis Effects 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000006751 Mitsunobu reaction Methods 0.000 claims description 3
- DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 230000000865 phosphorylative effect Effects 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 208000030507 AIDS Diseases 0.000 claims description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 2
- 206010019280 Heart failures Diseases 0.000 claims description 2
- 208000032456 Hemorrhagic Shock Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 206010022680 Intestinal ischaemia Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
- 206010040047 Sepsis Diseases 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims description 2
- 206010049771 Shock haemorrhagic Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 2
- 206010044541 Traumatic shock Diseases 0.000 claims description 2
- 208000024248 Vascular System injury Diseases 0.000 claims description 2
- 208000012339 Vascular injury Diseases 0.000 claims description 2
- 206010053648 Vascular occlusion Diseases 0.000 claims description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 230000033115 angiogenesis Effects 0.000 claims description 2
- 238000002399 angioplasty Methods 0.000 claims description 2
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 210000004413 cardiac myocyte Anatomy 0.000 claims description 2
- 208000015114 central nervous system disease Diseases 0.000 claims description 2
- 206010008118 cerebral infarction Diseases 0.000 claims description 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 210000003979 eosinophil Anatomy 0.000 claims description 2
- 208000024908 graft versus host disease Diseases 0.000 claims description 2
- 210000003630 histaminocyte Anatomy 0.000 claims description 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 201000006370 kidney failure Diseases 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 150000004682 monohydrates Chemical class 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- 201000002793 renal fibrosis Diseases 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 230000036303 septic shock Effects 0.000 claims description 2
- 208000021331 vascular occlusion disease Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 102000001253 Protein Kinase Human genes 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 108060006633 protein kinase Proteins 0.000 claims 1
- YIQFXQJHSDPEQS-UHFFFAOYSA-N 3-[3-(4,7-diazaspiro[2.5]octan-7-yl)isoquinolin-1-yl]-1-(hydroxymethyl)-4-(7-methyl-1h-indol-3-yl)pyrrole-2,5-dione Chemical compound C=1NC=2C(C)=CC=CC=2C=1C(C(N(CO)C1=O)=O)=C1C(C1=CC=CC=C1C=1)=NC=1N(C1)CCNC21CC2 YIQFXQJHSDPEQS-UHFFFAOYSA-N 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161486808P | 2011-05-17 | 2011-05-17 | |
| US61/486,808 | 2011-05-17 | ||
| PCT/IB2012/052473 WO2012156936A1 (en) | 2011-05-17 | 2012-05-16 | Substituted indole derivatives for the treatment of immunological disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014518870A JP2014518870A (ja) | 2014-08-07 |
| JP2014518870A5 true JP2014518870A5 (https=) | 2015-07-02 |
| JP6043344B2 JP6043344B2 (ja) | 2016-12-14 |
Family
ID=46210333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014510933A Active JP6043344B2 (ja) | 2011-05-17 | 2012-05-16 | 免疫学的障害の治療のための置換インドール誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US8703782B2 (https=) |
| EP (1) | EP2709998B1 (https=) |
| JP (1) | JP6043344B2 (https=) |
| KR (1) | KR20140023354A (https=) |
| CN (1) | CN103534250B (https=) |
| AR (1) | AR088414A1 (https=) |
| AU (1) | AU2012257345B2 (https=) |
| BR (1) | BR112013029416A2 (https=) |
| CA (1) | CA2835169C (https=) |
| EA (1) | EA023238B1 (https=) |
| ES (1) | ES2565200T3 (https=) |
| MX (1) | MX2013013436A (https=) |
| TW (1) | TW201249858A (https=) |
| UY (1) | UY34072A (https=) |
| WO (1) | WO2012156936A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY34072A (es) | 2011-05-17 | 2013-01-03 | Novartis Ag | Derivados sustituidos de indol |
| BR112015009214A2 (pt) * | 2012-11-07 | 2017-07-04 | Novartis Ag | derivados de indol substituído |
| CN105828822B (zh) | 2013-08-14 | 2019-10-18 | 诺华股份有限公司 | 用于治疗癌症的组合疗法 |
| ES2851724T3 (es) | 2013-09-18 | 2021-09-08 | Epiaxis Therapeutics Pty Ltd | Modulación de células madre |
| CA2958704A1 (en) | 2014-08-25 | 2016-03-03 | University Of Canberra | Compositions for modulating cancer stem cells and uses therefor |
| WO2025091442A1 (zh) * | 2023-11-03 | 2025-05-08 | 北京凯因科技股份有限公司 | 一种神经氨酸酶抑制剂及在流感病毒中的应用 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4925860A (en) | 1987-08-05 | 1990-05-15 | E. I. Du Pont De Nemours And Company | Stable pharmaceutical composition of 3-(hydroxymethyl)-5,5-diphenylhydantoin disodium phosphate ester |
| DE4005970A1 (de) | 1990-02-26 | 1991-08-29 | Boehringer Mannheim Gmbh | Neue trisubstituierte maleinimide, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten |
| GB9721069D0 (en) | 1997-10-03 | 1997-12-03 | Pharmacia & Upjohn Spa | Polymeric derivatives of camptothecin |
| US6204257B1 (en) | 1998-08-07 | 2001-03-20 | Universtiy Of Kansas | Water soluble prodrugs of hindered alcohols |
| CA2385071A1 (en) | 1999-10-12 | 2001-04-19 | Norman Kong | Substituted pyrroles as antiproliferative agents for the treatment of cancer |
| EP2070921A1 (en) | 2000-11-07 | 2009-06-17 | Novartis Ag | Indolylmaleimide derivatives as protein kinase c inhibitors |
| JP4369237B2 (ja) | 2001-12-21 | 2009-11-18 | エーザイ コーポレーション オブ ノース アメリカ | アルコールおよびフェノールの水溶性ホスホノオキシメチル誘導体の調製法 |
| NZ533536A (en) | 2001-12-28 | 2006-11-30 | Mgi Gp Inc | Aqueous based pharmaceutical formulations of water-soluble prodrugs of propofol such as O-phosphonooxymethyl propofol |
| TW200918046A (en) | 2002-04-03 | 2009-05-01 | Novartis Ag | Indolylmaleimide derivatives |
| HUP0600241A2 (en) | 2002-04-08 | 2006-07-28 | Mgi Gp | Pharmaceutical compositions containing water-soluble prodrugs of propofol and methods of administering same |
| JP2007524596A (ja) | 2003-02-28 | 2007-08-30 | トランスフォーム・ファーマシューティカルズ・インコーポレイテッド | 共結晶医薬組成物 |
| AU2003223104A1 (en) | 2003-03-19 | 2004-10-11 | Suven Life Sciences Limited | A process for the preparation of indolymaleimides |
| AU2006206458B2 (en) | 2005-01-19 | 2012-10-25 | Rigel Pharmaceuticals, Inc. | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
| WO2007008514A2 (en) | 2005-07-07 | 2007-01-18 | Georgetown University | Inhibitors of glycogen synthase kinase 3 |
| US20070203236A1 (en) | 2006-01-11 | 2007-08-30 | Smith Jeffrey W | Novel antagonists of the human fatty acid synthase thioesterase |
| GB0605691D0 (en) | 2006-03-21 | 2006-05-03 | Novartis Ag | Organic Compounds |
| ATE540041T1 (de) | 2006-11-21 | 2012-01-15 | Rigel Pharmaceuticals Inc | Prodrug-salze von 2,4-pyrimidindiaminverbindungen und anwendungen davon |
| WO2011057204A2 (en) | 2009-11-06 | 2011-05-12 | The Johns Hopkins University | Lrrk2-mediated neuronal toxicity |
| CN101812097B (zh) | 2010-04-17 | 2012-04-25 | 中国海洋大学 | 吲哚咔唑和双吲哚马来酰亚胺生物碱及其制备方法和应用 |
| UY34072A (es) | 2011-05-17 | 2013-01-03 | Novartis Ag | Derivados sustituidos de indol |
-
2012
- 2012-05-14 UY UY34072A patent/UY34072A/es not_active Application Discontinuation
- 2012-05-15 US US13/471,512 patent/US8703782B2/en active Active
- 2012-05-16 MX MX2013013436A patent/MX2013013436A/es not_active Application Discontinuation
- 2012-05-16 TW TW101117465A patent/TW201249858A/zh unknown
- 2012-05-16 JP JP2014510933A patent/JP6043344B2/ja active Active
- 2012-05-16 EA EA201391710A patent/EA023238B1/ru not_active IP Right Cessation
- 2012-05-16 KR KR20137030038A patent/KR20140023354A/ko not_active Withdrawn
- 2012-05-16 CA CA2835169A patent/CA2835169C/en active Active
- 2012-05-16 CN CN201280023473.2A patent/CN103534250B/zh active Active
- 2012-05-16 ES ES12726226.9T patent/ES2565200T3/es active Active
- 2012-05-16 WO PCT/IB2012/052473 patent/WO2012156936A1/en not_active Ceased
- 2012-05-16 AU AU2012257345A patent/AU2012257345B2/en active Active
- 2012-05-16 EP EP12726226.9A patent/EP2709998B1/en active Active
- 2012-05-16 BR BR112013029416A patent/BR112013029416A2/pt not_active IP Right Cessation
- 2012-05-18 AR ARP120101769 patent/AR088414A1/es not_active Application Discontinuation
-
2014
- 2014-03-03 US US14/194,879 patent/US9029396B2/en active Active
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