AU2006315467B2 - Bisamide inhibitors of hedgehog signaling - Google Patents
Bisamide inhibitors of hedgehog signaling Download PDFInfo
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- AU2006315467B2 AU2006315467B2 AU2006315467A AU2006315467A AU2006315467B2 AU 2006315467 B2 AU2006315467 B2 AU 2006315467B2 AU 2006315467 A AU2006315467 A AU 2006315467A AU 2006315467 A AU2006315467 A AU 2006315467A AU 2006315467 B2 AU2006315467 B2 AU 2006315467B2
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- chloro
- nicotinamide
- phenyl
- alkyl
- amino
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- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
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- Pain & Pain Management (AREA)
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- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73586105P | 2005-11-14 | 2005-11-14 | |
| US60/735,861 | 2005-11-14 | ||
| PCT/US2006/044240 WO2007059157A1 (en) | 2005-11-14 | 2006-11-14 | Bisamide inhibitors of hedgehog signaling |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006315467A1 AU2006315467A1 (en) | 2007-05-24 |
| AU2006315467B2 true AU2006315467B2 (en) | 2013-02-07 |
Family
ID=37734100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006315467A Ceased AU2006315467B2 (en) | 2005-11-14 | 2006-11-14 | Bisamide inhibitors of hedgehog signaling |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8101610B2 (https=) |
| EP (1) | EP1957461B1 (https=) |
| JP (2) | JP5225857B2 (https=) |
| AU (1) | AU2006315467B2 (https=) |
| CA (1) | CA2629814C (https=) |
| DK (1) | DK1957461T3 (https=) |
| ES (1) | ES2604539T3 (https=) |
| WO (1) | WO2007059157A1 (https=) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI433674B (zh) | 2006-12-28 | 2014-04-11 | Infinity Discovery Inc | 環杷明(cyclopamine)類似物類 |
| PE20090188A1 (es) * | 2007-03-15 | 2009-03-20 | Novartis Ag | Compuestos heterociclicos como moduladores de la senda de hedgehog |
| AU2008345097A1 (en) | 2007-12-27 | 2009-07-09 | Infinity Pharmaceuticals, Inc. | Methods for stereoselective reduction |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| US20100041663A1 (en) * | 2008-07-18 | 2010-02-18 | Novartis Ag | Organic Compounds as Smo Inhibitors |
| FR2948367A1 (fr) | 2009-07-24 | 2011-01-28 | Centre Nat Rech Scient | Derives d'acyl-guanidines modulateurs de la voie de signalisation des proteines hedgehog |
| WO2011014888A1 (en) * | 2009-07-31 | 2011-02-03 | Selexagen Therapeutics | Novel hedgehog inhibitors |
| JP6141015B2 (ja) | 2009-08-05 | 2017-06-07 | インフィニティ ファーマスーティカルズ、インク. | シクロパミン類似体の酵素によるアミノ基転移 |
| DK2473522T3 (en) | 2009-09-02 | 2016-11-28 | Genentech Inc | Smoothened MUTANT AND METHODS OF USING THE SAME |
| WO2011085128A1 (en) | 2010-01-07 | 2011-07-14 | Selexagen Therapeutics, Inc. | Hedgehog inhibitors |
| CA2799579A1 (en) | 2010-05-21 | 2011-11-24 | Intellikine, Inc. | Chemical compounds, compositions and methods for kinase modulation |
| US9394313B2 (en) | 2010-09-14 | 2016-07-19 | Infinity Pharmaceuticals, Inc. | Transfer hydrogenation of cyclopamine analogs |
| US8481680B2 (en) | 2010-10-05 | 2013-07-09 | Genentech, Inc. | Mutant smoothened and methods of using the same |
| JP2013545749A (ja) | 2010-11-10 | 2013-12-26 | インフィニティー ファーマシューティカルズ, インコーポレイテッド | 複素環化合物及びその使用 |
| FR2967498B1 (fr) | 2010-11-16 | 2015-01-02 | Centre Nat Rech Scient | Utilisation de derives de quinolinone comme outil de recherche |
| US9708299B2 (en) | 2011-01-03 | 2017-07-18 | Genentech, Inc. | Hedgehog antagonists having zinc binding moieties |
| TWI674262B (zh) | 2011-01-10 | 2019-10-11 | 美商英菲尼提製藥股份有限公司 | 製備異喹啉酮之方法及異喹啉酮之固體形式 |
| WO2012151544A1 (en) | 2011-05-05 | 2012-11-08 | Wisconsin Alumni Research Foundation | Micelles for the solubilization of gossypol |
| WO2013012915A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| MX2014000648A (es) | 2011-07-19 | 2014-09-25 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos y sus usos. |
| KR20140075693A (ko) | 2011-08-29 | 2014-06-19 | 인피니티 파마슈티칼스, 인코포레이티드 | 헤테로사이클릭 화합물 및 그의 용도 |
| FR2980477B1 (fr) | 2011-09-23 | 2013-10-18 | Centre Nat Rech Scient | Nouveaux composes modulateurs de la voie de signalisation des proteines hedgehog, leurs formes marquees, et applications |
| WO2013049332A1 (en) | 2011-09-29 | 2013-04-04 | Infinity Pharmaceuticals, Inc. | Inhibitors of monoacylglycerol lipase and methods of their use |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| JP6233932B2 (ja) | 2012-08-30 | 2017-11-22 | 国立大学法人広島大学 | BBF2H7(BBF2 human homologue on chromosome7)部分アミノ酸配列を有するペプチドまたはそれに結合する抗体を含む細胞増殖調節用組成物 |
| EP2895474B1 (en) * | 2012-09-17 | 2019-12-11 | Duke University | Smoothened receptor modulators and methods of use thereof |
| EP2914296B2 (en) | 2012-11-01 | 2021-09-29 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
| JP6372666B2 (ja) | 2012-11-03 | 2018-08-15 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | サイトメガロウイルスの阻害剤 |
| CA2893133A1 (en) | 2012-11-29 | 2014-06-05 | Strasspharma Llc | Methods of modulating follicle stimulating hormone activity |
| US20160024051A1 (en) | 2013-03-15 | 2016-01-28 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| RU2665688C2 (ru) * | 2013-04-12 | 2018-09-04 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Производные бисамидов дикарбоновых кислот, их применение, фармацевтическая композиция на их основе, способы их получения |
| US9192609B2 (en) | 2013-04-17 | 2015-11-24 | Hedgepath Pharmaceuticals, Inc. | Treatment and prognostic monitoring of proliferation disorders using hedgehog pathway inhibitors |
| SG11201509842SA (en) | 2013-05-30 | 2015-12-30 | Infinity Pharmaceuticals Inc | Treatment of cancers using pi3 kinase isoform modulators |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| GB201317609D0 (en) | 2013-10-04 | 2013-11-20 | Cancer Rec Tech Ltd | Inhibitor compounds |
| MX2021012208A (es) | 2013-10-04 | 2023-01-19 | Infinity Pharmaceuticals Inc | Compuestos heterocíclicos y usos de los mismos. |
| WO2015061204A1 (en) | 2013-10-21 | 2015-04-30 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| EP3079682A4 (en) * | 2013-12-13 | 2017-08-30 | Dana-Farber Cancer Institute, Inc. | Methods to treat lymphoplasmacytic lymphoma |
| US9856223B2 (en) | 2013-12-13 | 2018-01-02 | Dana-Farber Cancer Institute, Inc. | Methods to treat lymphoplasmacytic lymphoma |
| JP6736467B2 (ja) | 2014-02-04 | 2020-08-05 | ジェネンテック, インコーポレイテッド | 平滑化変異体及びその使用方法 |
| NZ724368A (en) | 2014-03-19 | 2023-07-28 | Infinity Pharmaceuticals Inc | Heterocyclic compounds for use in the treatment of pi3k-gamma mediated disorders |
| US20150320754A1 (en) | 2014-04-16 | 2015-11-12 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| WO2015168079A1 (en) | 2014-04-29 | 2015-11-05 | Infinity Pharmaceuticals, Inc. | Pyrimidine or pyridine derivatives useful as pi3k inhibitors |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US10112957B2 (en) | 2014-10-22 | 2018-10-30 | Dana-Farber Cancer Institute, Inc. | Thiazolyl-containing compounds for treating proliferative diseases |
| CA2975875A1 (en) | 2015-02-04 | 2016-08-11 | Genentech, Inc. | Mutant smoothened and methods of using the same |
| GB201505658D0 (en) | 2015-04-01 | 2015-05-13 | Cancer Rec Tech Ltd | Inhibitor compounds |
| CN104876879B (zh) * | 2015-04-14 | 2018-05-18 | 中国科学院合肥物质科学研究院 | 一种bcr-abl激酶抑制剂 |
| CA2988289C (en) | 2015-06-04 | 2023-12-05 | PellePharm, Inc. | Topical formulations for delivery of hedgehog inhibitor compounds and use thereof |
| EP4585268A3 (en) | 2015-09-14 | 2025-10-15 | Twelve Therapeutics, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| US20170231968A1 (en) | 2016-02-11 | 2017-08-17 | PellePharm, Inc. | Method for relief of and treatment of pruritus |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| RU2754507C2 (ru) | 2016-06-24 | 2021-09-02 | Инфинити Фармасьютикалз, Инк. | Комбинированная терапия |
| US10548908B2 (en) * | 2016-09-15 | 2020-02-04 | Nostopharma, LLC | Compositions and methods for preventing and treating heterotopic ossification and pathologic calcification |
| GB201617103D0 (en) | 2016-10-07 | 2016-11-23 | Cancer Research Technology Limited | Compound |
| RU2709529C1 (ru) * | 2018-08-06 | 2019-12-18 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Производные бисамидов дикарбоновых кислот, их применение, фармацевтическая композиция на их основе, способы их получения |
| RU2725881C2 (ru) * | 2018-08-06 | 2020-07-07 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Производное бисамидов дикарбоновых кислот, его применение, фармацевтическая композиция на его основе, способы его получения |
| RU2721421C2 (ru) * | 2018-08-06 | 2020-05-19 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Производное бисамидов дикарбоновых кислот, его применение, фармацевтическая композиция на его основе, способы его получения |
| RU2725770C2 (ru) * | 2018-08-06 | 2020-07-07 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Производное бисамидов дикарбоновых кислот, его применение, фармацевтическая композиция на его основе, способы его получения |
| WO2021241913A1 (ko) * | 2020-05-29 | 2021-12-02 | 주식회사 헤지호그 | 페닐렌 디벤즈아미드계 화합물 및 이를 유효성분으로 포함하는 암질환 예방 또는 치료용 약제학적 조성물 |
| US12605387B2 (en) | 2020-07-24 | 2026-04-21 | Secura Bio, Inc. | Treatment of cancers using PI3 kinase isoform modulators |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998022103A1 (en) * | 1996-11-16 | 1998-05-28 | Zeneca Limited | Raf kinase inhibitors |
| WO1999015164A1 (en) * | 1997-09-23 | 1999-04-01 | Zeneca Limited | Amide derivatives for the treatment of diseases mediated by cytokines |
| WO1999059960A1 (en) * | 1998-05-15 | 1999-11-25 | Astrazeneca Ab | Benzamide derivatives for the treatment of diseases mediated by cytokines |
| WO2000007991A1 (en) * | 1998-08-04 | 2000-02-17 | Astrazeneca Ab | Amide derivatives useful as inhibitors of the production of cytokines |
| WO2000018738A1 (en) * | 1998-09-25 | 2000-04-06 | Astrazeneca Ab | Benzamide derivatives and their use as cytokine inhibitors |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7351834B1 (en) * | 1999-01-13 | 2008-04-01 | Bayer Pharmaceuticals Corporation | ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US7202257B2 (en) * | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| US8067608B2 (en) * | 2003-09-29 | 2011-11-29 | The Johns Hopkins University | Hedgehog pathway antagonists |
| WO2006007520A1 (en) | 2004-07-01 | 2006-01-19 | Wisconsin Alumni Research Foundation | Hydroxybenazamide compounds for treatment of cancer |
| TW200616974A (en) * | 2004-07-01 | 2006-06-01 | Astrazeneca Ab | Chemical compounds |
| EP1789400A1 (en) * | 2004-09-01 | 2007-05-30 | AstraZeneca AB | Quinazolinone derivatives and their use as b-raf inhibitors |
| WO2006040568A1 (en) * | 2004-10-15 | 2006-04-20 | Astrazeneca Ab | Quinoxalines as b raf inhibitors |
-
2006
- 2006-11-14 US US12/093,530 patent/US8101610B2/en not_active Expired - Fee Related
- 2006-11-14 JP JP2008541289A patent/JP5225857B2/ja not_active Expired - Fee Related
- 2006-11-14 ES ES06844364.7T patent/ES2604539T3/es active Active
- 2006-11-14 WO PCT/US2006/044240 patent/WO2007059157A1/en not_active Ceased
- 2006-11-14 CA CA2629814A patent/CA2629814C/en not_active Expired - Fee Related
- 2006-11-14 AU AU2006315467A patent/AU2006315467B2/en not_active Ceased
- 2006-11-14 EP EP06844364.7A patent/EP1957461B1/en active Active
- 2006-11-14 DK DK06844364.7T patent/DK1957461T3/en active
-
2013
- 2013-01-16 JP JP2013005689A patent/JP2013079283A/ja active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998022103A1 (en) * | 1996-11-16 | 1998-05-28 | Zeneca Limited | Raf kinase inhibitors |
| WO1999015164A1 (en) * | 1997-09-23 | 1999-04-01 | Zeneca Limited | Amide derivatives for the treatment of diseases mediated by cytokines |
| WO1999059960A1 (en) * | 1998-05-15 | 1999-11-25 | Astrazeneca Ab | Benzamide derivatives for the treatment of diseases mediated by cytokines |
| WO2000007991A1 (en) * | 1998-08-04 | 2000-02-17 | Astrazeneca Ab | Amide derivatives useful as inhibitors of the production of cytokines |
| WO2000018738A1 (en) * | 1998-09-25 | 2000-04-06 | Astrazeneca Ab | Benzamide derivatives and their use as cytokine inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080269215A1 (en) | 2008-10-30 |
| US8101610B2 (en) | 2012-01-24 |
| WO2007059157A1 (en) | 2007-05-24 |
| JP2013079283A (ja) | 2013-05-02 |
| EP1957461B1 (en) | 2016-11-02 |
| JP2009516685A (ja) | 2009-04-23 |
| AU2006315467A1 (en) | 2007-05-24 |
| DK1957461T3 (en) | 2016-12-19 |
| ES2604539T3 (es) | 2017-03-07 |
| EP1957461A1 (en) | 2008-08-20 |
| JP5225857B2 (ja) | 2013-07-03 |
| CA2629814A1 (en) | 2007-05-24 |
| CA2629814C (en) | 2013-12-31 |
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