ES2424259T3 - Triazoles sustituidos con arilo policíclico y heteroarilo policíclico, útiles como agentes inhibidores del Axl - Google Patents
Triazoles sustituidos con arilo policíclico y heteroarilo policíclico, útiles como agentes inhibidores del Axl Download PDFInfo
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- ES2424259T3 ES2424259T3 ES07870108T ES07870108T ES2424259T3 ES 2424259 T3 ES2424259 T3 ES 2424259T3 ES 07870108 T ES07870108 T ES 07870108T ES 07870108 T ES07870108 T ES 07870108T ES 2424259 T3 ES2424259 T3 ES 2424259T3
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- Prior art keywords
- optionally substituted
- heteroaryl
- independently
- alkyl
- heterocyclyl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title description 3
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 370
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 323
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- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 221
- 125000004419 alkynylene group Chemical group 0.000 claims abstract description 213
- 125000001424 substituent group Chemical group 0.000 claims abstract description 200
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 199
- 239000001257 hydrogen Substances 0.000 claims abstract description 198
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 198
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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| EP4568670A1 (en) | 2022-08-10 | 2025-06-18 | Institut National de la Santé et de la Recherche Médicale | Sigmar1 ligand for the treatment of pancreatic cancer |
| WO2024033400A1 (en) | 2022-08-10 | 2024-02-15 | Institut National de la Santé et de la Recherche Médicale | Sk2 inhibitor for the treatment of pancreatic cancer |
| WO2024051667A1 (zh) * | 2022-09-05 | 2024-03-14 | 南京正大天晴制药有限公司 | 具有axl抑制活性的取代三唑化合物 |
| EP4587040A1 (en) | 2022-09-14 | 2025-07-23 | Institut National de la Santé et de la Recherche Médicale | Methods and pharmaceutical compositions for the treatment of dilated cardiomyopathy |
| WO2024084034A1 (en) | 2022-10-21 | 2024-04-25 | Institut National de la Santé et de la Recherche Médicale | Methods and pharmaceutical compositions for the treatment of osteoarthritis |
| WO2024200571A1 (en) | 2023-03-28 | 2024-10-03 | Institut National de la Santé et de la Recherche Médicale | Method for discriminating mono-immunotherapy from combined immunotherapy in cancers |
| WO2024231384A1 (en) | 2023-05-10 | 2024-11-14 | Institut National de la Santé et de la Recherche Médicale | Compositions for treating senescence related disease |
| AU2024273407A1 (en) | 2023-05-17 | 2025-12-04 | Centre National De La Recherche Scientifique | Anti-cathepsin-d antibodies |
| WO2024245951A1 (en) | 2023-05-26 | 2024-12-05 | Institut National de la Santé et de la Recherche Médicale | Combination of slc8a1 inhibitor and mitochondria-targeted antioxidant for treating melanoma |
| WO2024256635A1 (en) | 2023-06-15 | 2024-12-19 | Institut National de la Santé et de la Recherche Médicale | Dpm1 inhibitor for treating cancer |
| WO2025068180A1 (en) | 2023-09-25 | 2025-04-03 | Institut National de la Santé et de la Recherche Médicale | Methods of treatment of cancer by targetting cancer - associated fibroblasts |
| WO2025073765A1 (en) | 2023-10-03 | 2025-04-10 | Institut National de la Santé et de la Recherche Médicale | Methods of prognosis and treatment of patients suffering from melanoma |
| WO2025078632A1 (en) | 2023-10-12 | 2025-04-17 | Institut National de la Santé et de la Recherche Médicale | Methods of prognosis and treatment of patients suffering from cancer |
| WO2025132479A1 (en) | 2023-12-18 | 2025-06-26 | Institut National de la Santé et de la Recherche Médicale | Flt3 inhibitor for modulating macrophages polarization |
| WO2025132770A1 (en) | 2023-12-22 | 2025-06-26 | Institut National de la Santé et de la Recherche Médicale | Affitins for the treatment of cancer |
| WO2025210123A1 (en) | 2024-04-03 | 2025-10-09 | Institut National de la Santé et de la Recherche Médicale | Methods and pharmaceutical composition for treating cancers |
| WO2025219330A1 (en) | 2024-04-15 | 2025-10-23 | Institut National de la Santé et de la Recherche Médicale | Detection of ppix for use in methods for melanoma ferroptosis sensitivity and targeted therapy resistance prediction |
| WO2025228998A1 (en) | 2024-04-30 | 2025-11-06 | Institut National de la Santé et de la Recherche Médicale | Use of hdac4 inhibitors for the treatment of melanoma |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1403866A (en) | 1971-12-06 | 1975-08-28 | Wyeth John & Brother Ltd | Derivatives of 3-amino-1,2,4-triazoles |
| US5750545A (en) | 1993-07-23 | 1998-05-12 | The Green Cross Corporation | Triazole derivative and pharmaceutical use thereof |
| GB9918180D0 (en) | 1999-08-02 | 1999-10-06 | Smithkline Beecham Plc | Novel compositions |
| EP1355889B1 (en) * | 2000-12-22 | 2006-06-07 | Ortho-McNeil Pharmaceutical, Inc. | Substituted triazole diamine derivatives as kinase inhibitors |
| TW201041580A (en) | 2001-09-27 | 2010-12-01 | Alcon Inc | Inhibitors of glycogen synthase kinase-3 (GSK-3) for treating glaucoma |
| US20060034797A1 (en) | 2002-05-03 | 2006-02-16 | Arien Albertina M E | Polymeric micromulsions |
| JP4483581B2 (ja) * | 2002-08-06 | 2010-06-16 | 東レ株式会社 | 腎疾患治療又は予防剤及び腎疾患の診断方法 |
| AU2003286746A1 (en) | 2002-10-29 | 2004-05-25 | Rigel Pharmaceuticals, Inc. | Modulators of angiogenesis and tumorigenesis |
| AR042052A1 (es) * | 2002-11-15 | 2005-06-08 | Vertex Pharma | Diaminotriazoles utiles como inhibidores de proteinquinasas |
| US7226920B2 (en) | 2003-08-06 | 2007-06-05 | Vertex Pharmaceuticals Inc. | Aminotriazole compounds useful as inhibitors of protein kinases |
| EP1720843A2 (en) | 2004-02-11 | 2006-11-15 | Janssen Pharmaceutica N.V. | Process for the preparation of substituted triazole compounds |
| ES2401138T3 (es) | 2004-08-13 | 2013-04-17 | Genentech, Inc. | Inhibidores basados en tiazol de enzimas que usan ATP |
| DK1791830T3 (da) | 2004-09-17 | 2011-04-18 | Vertex Pharma | Diaminotriazol-forbindelser der er nyttige som protein-kinase-inhibitorer |
| US7884119B2 (en) * | 2005-09-07 | 2011-02-08 | Rigel Pharmaceuticals, Inc. | Triazole derivatives useful as Axl inhibitors |
| US8097630B2 (en) * | 2006-10-10 | 2012-01-17 | Rigel Pharmaceuticals, Inc. | Pinane-substituted pyrimidinediamine derivatives useful as Axl inhibitors |
| US7879856B2 (en) * | 2006-12-22 | 2011-02-01 | Rigel Pharmaceuticals, Inc. | Diaminothiazoles useful as Axl inhibitors |
| US8012965B2 (en) * | 2006-12-29 | 2011-09-06 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic aryl and bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| EP2074115B1 (en) * | 2006-12-29 | 2018-03-07 | Rigel Pharmaceuticals, Inc. | N3-heteroaryl substituted triazoles and n5-heteroaryl substituted triazoles useful as axl inhibitors |
| EP2078010B1 (en) * | 2006-12-29 | 2014-01-29 | Rigel Pharmaceuticals, Inc. | Polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
| AU2007342007A1 (en) * | 2006-12-29 | 2008-07-10 | Rigel Pharmaceuticals, Inc. | Substituted triazoles useful as Axl inhibitors |
| WO2008083353A1 (en) * | 2006-12-29 | 2008-07-10 | Rigel Pharmaceuticals, Inc. | Bicyclic aryl and bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CA2690653A1 (en) | 2007-06-15 | 2008-12-24 | Irm Llc | Protein kinase inhibitors and methods for using thereof |
| ES2424259T3 (es) * | 2007-10-26 | 2013-09-30 | Rigel Pharmaceuticals, Inc. | Triazoles sustituidos con arilo policíclico y heteroarilo policíclico, útiles como agentes inhibidores del Axl |
| LT2265607T (lt) * | 2008-02-15 | 2017-03-27 | Rigel Pharmaceuticals, Inc. | Pirimidin-2-amino junginiai ir jų panaudojimas kaip jak kinazių slopiklių |
| WO2010005879A1 (en) * | 2008-07-09 | 2010-01-14 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| JP5592884B2 (ja) * | 2008-07-09 | 2014-09-17 | ライジェル ファーマシューティカルズ, インコーポレイテッド | Axl阻害剤として有用な多環式ヘテロアリール置換トリアゾール |
| CA2749843C (en) * | 2009-01-16 | 2017-09-05 | Rigel Pharmaceuticals, Inc. | Axl inhibitors for use in combination therapy for preventing, treating or managing metastatic cancer |
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| EP2205592B1 (en) | 2013-05-08 |
| JP5635909B2 (ja) | 2014-12-03 |
| EP2205592A1 (en) | 2010-07-14 |
| US7935693B2 (en) | 2011-05-03 |
| CA2704052C (en) | 2015-04-21 |
| SI2205592T1 (sl) | 2013-09-30 |
| US20110183986A1 (en) | 2011-07-28 |
| JP2011500801A (ja) | 2011-01-06 |
| CA2704052A1 (en) | 2009-04-30 |
| US8809364B2 (en) | 2014-08-19 |
| US20090111816A1 (en) | 2009-04-30 |
| WO2009054864A1 (en) | 2009-04-30 |
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