AU2005206570A1 - Tetrahydrocarboline compounds as anticancer agents - Google Patents
Tetrahydrocarboline compounds as anticancer agents Download PDFInfo
- Publication number
- AU2005206570A1 AU2005206570A1 AU2005206570A AU2005206570A AU2005206570A1 AU 2005206570 A1 AU2005206570 A1 AU 2005206570A1 AU 2005206570 A AU2005206570 A AU 2005206570A AU 2005206570 A AU2005206570 A AU 2005206570A AU 2005206570 A1 AU2005206570 A1 AU 2005206570A1
- Authority
- AU
- Australia
- Prior art keywords
- substituted
- beta
- tetrahydro
- carbolin
- compound
- 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.)
- Abandoned
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- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical group CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53898004P | 2004-01-23 | 2004-01-23 | |
| US60/538,980 | 2004-01-23 | ||
| PCT/US2005/002270 WO2005070930A2 (en) | 2004-01-23 | 2005-01-24 | Tetrahydrocarboline compounds as anticancer agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2005206570A1 true AU2005206570A1 (en) | 2005-08-04 |
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|---|---|---|---|
| AU2005206570A Abandoned AU2005206570A1 (en) | 2004-01-23 | 2005-01-24 | Tetrahydrocarboline compounds as anticancer agents |
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| Country | Link |
|---|---|
| US (1) | US7855295B2 (enExample) |
| EP (1) | EP1706404A2 (enExample) |
| JP (1) | JP2007518822A (enExample) |
| CN (1) | CN1910183A (enExample) |
| AU (1) | AU2005206570A1 (enExample) |
| BR (1) | BRPI0506977A (enExample) |
| CA (1) | CA2554150A1 (enExample) |
| MX (1) | MXPA06008211A (enExample) |
| WO (1) | WO2005070930A2 (enExample) |
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| EP1637521B1 (en) * | 2003-06-23 | 2013-06-19 | Ono Pharmaceutical Co., Ltd. | Novel tricyclic heterocycle compound |
| US7767689B2 (en) | 2004-03-15 | 2010-08-03 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the treatment of cancer |
| US8076353B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Inhibition of VEGF translation |
| ES2401335T3 (es) | 2004-03-15 | 2013-04-18 | Ptc Therapeutics, Inc. | Derivados de carbolina útiles en la inhibición de la angiogénesis |
| US8076352B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| PL1829874T3 (pl) | 2004-12-22 | 2014-07-31 | Ono Pharmaceutical Co | Tricykliczny związek i jego zastosowanie |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| BRPI0719883A2 (pt) | 2006-10-09 | 2015-05-05 | Takeda Pharmaceutical | Inibidores de quinase |
| WO2008103470A2 (en) | 2007-02-21 | 2008-08-28 | Trustees Of Columbia University In The City Of New York | Oncogenic-ras-signal dependent lethal compounds |
| EP2214485B1 (en) * | 2007-09-25 | 2016-07-20 | Minerva Biotechnologies Corp. | Methods for treatment of cancer |
| US11202775B2 (en) | 2007-09-25 | 2021-12-21 | Minerva Biotechnologies Corporation | Methods for treatment of cancer |
| EP2050747A1 (en) * | 2007-10-12 | 2009-04-22 | BioAlliance Pharma | Dimers of harmol or of its derivatives and uses thereof |
| ES2523580T3 (es) | 2008-01-11 | 2014-11-27 | Albany Molecular Research, Inc. | Piridoindoles substituidos con (1-Azinona) |
| CN101591348B (zh) * | 2008-05-30 | 2011-07-27 | 首都医科大学 | 四氢咔啉酰氨基酸苄酯及其制备方法和应用 |
| CN101597289B (zh) * | 2008-06-02 | 2011-09-21 | 首都医科大学 | 2-色氨酰-β-四氢咔啉-3-甲酰基氨基酸苄酯及其制备方法和应用 |
| CA2763479A1 (en) | 2009-05-27 | 2010-12-02 | Ptc Therapeutics, Inc. | Processes for the preparation of substituted tetrahydro beta-carbolines |
| CN102480957A (zh) | 2009-05-27 | 2012-05-30 | Ptc医疗公司 | 治疗癌症及非肿瘤病症的方法 |
| WO2010138685A1 (en) | 2009-05-27 | 2010-12-02 | Ptc Therapeutics, Inc. | Methods for treating prostate conditions |
| WO2010138652A1 (en) | 2009-05-27 | 2010-12-02 | Ptc Therapeutics, Inc. | Methods for treating kaposi sarcoma |
| US8629158B2 (en) | 2009-07-01 | 2014-01-14 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| US9073925B2 (en) | 2009-07-01 | 2015-07-07 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| US8618299B2 (en) | 2009-07-01 | 2013-12-31 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle MCH-1 antagonists, methods of making, and use thereof |
| US8637501B2 (en) * | 2009-07-01 | 2014-01-28 | Albany Molecular Research, Inc. | Azinone-substituted azepino[b]indole and pyrido-pyrrolo-azepine MCH-1 antagonists, methods of making, and use thereof |
| FR2953839A1 (fr) * | 2009-12-14 | 2011-06-17 | Sanofi Aventis | Nouveaux derives d'(heterocycle-piperidine condensee)-(piperazinyl)-1alcanone ou d'(heterocycle-pyrrolidine condensee)-(piperazinyl)-1alcanone et leur utilisation comme inhibiteurs de p75 |
| SG186826A1 (en) * | 2010-07-06 | 2013-02-28 | Ono Pharmaceutical Co | Tetrahydrocarboline derivative |
| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
| WO2012088038A2 (en) | 2010-12-21 | 2012-06-28 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline mch-1 antagonists, methods of making, and uses thereof |
| ES2587856T3 (es) | 2011-03-18 | 2016-10-27 | Ono Pharmaceutical Co., Ltd. | Derivado de tetrahidrocarbolina |
| EP2802328B1 (en) | 2012-01-09 | 2018-03-07 | X-Chem, Inc. | Tryptoline derivatives having kinase inhibitory activity and uses thereof |
| CN103087062B (zh) * | 2013-01-19 | 2015-06-03 | 安徽师范大学 | N-磺酰基取代-β-四氢咔啉衍生物的制备方法 |
| LT3004090T (lt) * | 2013-05-28 | 2018-01-10 | Astrazeneca Ab | Cheminiai junginiai |
| EP3352566A4 (en) * | 2015-09-23 | 2019-07-31 | Minerva Biotechnologies Corporation | SCREENING METHOD FOR ACTIVE SUBSTANCES FOR DIFFERENTIATING STEM CELLS |
| JP2019001715A (ja) * | 2015-10-30 | 2019-01-10 | 協和発酵キリン株式会社 | 三環性化合物 |
| JP6592197B2 (ja) * | 2015-11-12 | 2019-10-16 | 浙江海正薬業股▲ふん▼有限公司Ｚｈｅｊｉａｎｇ Ｈｉｓｕｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌ ＣＯ．，ＬＴＤ． | アクリル酸誘導体、製造方法、および医薬としてのその使用 |
| CN106967063B (zh) * | 2017-03-21 | 2019-01-11 | 浙江大学 | 1-三氟甲基-1,2,3,4-四氢-β-咔啉衍生物及其制备方法 |
| EP3664803A4 (en) | 2017-08-01 | 2021-05-05 | PTC Therapeutics, Inc. | DHODH INHIBITOR FOR USE IN THE TREATMENT OF HEMATOLOGICAL CANCERS |
| WO2020072675A1 (en) | 2018-10-02 | 2020-04-09 | Northwestern University | Beta-carbolines as positive allosteric modulators of the human serotonin receptor 2c (5-ht2c) |
| CN110791389B (zh) * | 2019-09-30 | 2021-06-01 | 义乌欧风汽车用品有限公司 | 一种除胶剂及其制备方法和应用 |
| JP2025501285A (ja) * | 2021-12-31 | 2025-01-17 | ピーティーシー セラピューティクス， インコーポレイテッド | カルボリン化合物及びその使用 |
| CN120265629A (zh) * | 2022-11-07 | 2025-07-04 | 默克专利股份公司 | 被取代的双环和三环hset抑制剂 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE136032T1 (de) | 1987-07-20 | 1996-04-15 | Duphar Int Res | 8,9-anellierte 1,2,3,4-tetrahydro-beta-carbolin- derivate |
| EP0357122A3 (en) | 1988-08-29 | 1991-10-23 | Duphar International Research B.V | Use of beta-carbolines, their bio-isosteric benzofuran and benzothiophene analogues for the manufacture of a medicament having cytostatic properties |
| JPH03287586A (ja) | 1990-04-02 | 1991-12-18 | Taisho Pharmaceut Co Ltd | テトラヒドロ―β―カルボリン誘導体 |
| JP3287586B2 (ja) | 1991-07-09 | 2002-06-04 | キヤノン株式会社 | カラー画像処理方法、及びカラー画像処理装置 |
| US5206377A (en) * | 1991-12-05 | 1993-04-27 | Whitby Research, Inc. | Compounds useful as antiproliferative agents |
| US5622960A (en) | 1992-04-14 | 1997-04-22 | The United States Of America As Represented By The Department Of Health And Human Services | Topoisomerase II inhibitors and therapeutic uses therefor |
| US6069150A (en) * | 1996-04-04 | 2000-05-30 | F. Hoffman-La Roche Ag | Use of derivatives of tetrahydro-beta-carbolines as antimetastatic agents |
| FR2796644B1 (fr) | 1999-07-23 | 2001-09-07 | Adir | Nouveaux derives de beta-carboline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| UA74826C2 (en) | 2000-05-17 | 2006-02-15 | Ortho Mcneil Pharm Inc | ?-carboline derivatives as phosphodiesterase inhibitors |
| US6720331B2 (en) * | 2001-04-03 | 2004-04-13 | National Sun Yat-Sen University | 1-substituted 1,2,3,4-tetrahydro-β-carboline and 3,4-dihydro-β-carboline and analogs as antitumor agents |
| DK1438310T3 (da) * | 2001-10-19 | 2007-03-26 | Transtech Pharma Inc | Beta-carbolin-derivater som PTP-inhibitorer |
-
2005
- 2005-01-24 US US11/042,474 patent/US7855295B2/en not_active Expired - Fee Related
- 2005-01-24 CA CA002554150A patent/CA2554150A1/en not_active Abandoned
- 2005-01-24 EP EP05711958A patent/EP1706404A2/en not_active Withdrawn
- 2005-01-24 MX MXPA06008211A patent/MXPA06008211A/es unknown
- 2005-01-24 CN CNA2005800030203A patent/CN1910183A/zh active Pending
- 2005-01-24 WO PCT/US2005/002270 patent/WO2005070930A2/en not_active Ceased
- 2005-01-24 JP JP2006551391A patent/JP2007518822A/ja active Pending
- 2005-01-24 AU AU2005206570A patent/AU2005206570A1/en not_active Abandoned
- 2005-01-24 BR BRPI0506977-7A patent/BRPI0506977A/pt not_active IP Right Cessation
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|---|---|
| US20050215580A1 (en) | 2005-09-29 |
| CA2554150A1 (en) | 2005-08-04 |
| BRPI0506977A (pt) | 2007-07-03 |
| EP1706404A2 (en) | 2006-10-04 |
| WO2005070930A2 (en) | 2005-08-04 |
| JP2007518822A (ja) | 2007-07-12 |
| MXPA06008211A (es) | 2006-08-31 |
| CN1910183A (zh) | 2007-02-07 |
| WO2005070930A3 (en) | 2006-01-19 |
| US7855295B2 (en) | 2010-12-21 |
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| TH | Corrigenda |
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