EP2953947A1 - 3,5-diaryl-azaindoles comme inhibiteurs de la protéine dyrk1a pour le traitement des déficiences cognitives liées au syndrome de down et à la maladie d'alzheimer - Google Patents
3,5-diaryl-azaindoles comme inhibiteurs de la protéine dyrk1a pour le traitement des déficiences cognitives liées au syndrome de down et à la maladie d'alzheimerInfo
- Publication number
- EP2953947A1 EP2953947A1 EP13811495.4A EP13811495A EP2953947A1 EP 2953947 A1 EP2953947 A1 EP 2953947A1 EP 13811495 A EP13811495 A EP 13811495A EP 2953947 A1 EP2953947 A1 EP 2953947A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- compound
- different
- radicals
- nmr
- 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.)
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000011895 specific detection Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
Classifications
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hospice & Palliative Care (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1262275A FR2999575A1 (fr) | 2012-12-18 | 2012-12-18 | 3,5-diaryl-azaindoles comme inhibiteurs de la proteine dyrk1a pour le traitement des deficiences cognitives liees au syndrome de down et a la maladie d'alzheimer |
PCT/EP2013/077224 WO2014096093A1 (fr) | 2012-12-18 | 2013-12-18 | 3,5-diaryl-azaindoles comme inhibiteurs de la protéine dyrk1a pour le traitement des déficiences cognitives liées au syndrome de down et à la maladie d'alzheimer |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2953947A1 true EP2953947A1 (fr) | 2015-12-16 |
Family
ID=48407628
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP13811495.4A Withdrawn EP2953947A1 (fr) | 2012-12-18 | 2013-12-18 | 3,5-diaryl-azaindoles comme inhibiteurs de la protéine dyrk1a pour le traitement des déficiences cognitives liées au syndrome de down et à la maladie d'alzheimer |
Country Status (6)
Country | Link |
---|---|
US (1) | US9447093B2 (fr) |
EP (1) | EP2953947A1 (fr) |
JP (1) | JP2016505584A (fr) |
CA (1) | CA2896209A1 (fr) |
FR (1) | FR2999575A1 (fr) |
WO (1) | WO2014096093A1 (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11945818B1 (en) | 2023-09-06 | 2024-04-02 | King Faisal University | Pyrrolo[3,2-c]quinoline compounds as CK2 inhibitors |
US11945823B1 (en) | 2023-09-14 | 2024-04-02 | King Faisal University | Substituted pyrrolo[2,3-d]pyrimidines as CK2 inhibitors |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4787150B2 (ja) * | 2003-03-06 | 2011-10-05 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Jnk阻害剤 |
EP2786995A1 (fr) * | 2004-03-30 | 2014-10-08 | Vertex Pharmaceuticals Incorporated | Azaindoles utiles en tant qu'inhibiteurs de JAK et autres kinases de protéine |
US7709645B2 (en) * | 2004-07-27 | 2010-05-04 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
US7361764B2 (en) * | 2004-07-27 | 2008-04-22 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
EP1828180A4 (fr) * | 2004-12-08 | 2010-09-15 | Glaxosmithkline Llc | 1h -pyrrolo[2,3-beta]pyridines |
FR2912744B1 (fr) * | 2007-02-16 | 2012-09-07 | Centre Nat Rech Scient | Composes pyrrolo°2,3-b!pyridine,composes azaindoles utiles dans la synthese de ces composes pyrrolo°2,3-b!pyridine, leurs procedes de fabrication et leurs utilisations. |
WO2010049173A1 (fr) * | 2008-10-31 | 2010-05-06 | Cenix Bioscience Gmbh | Utilisation d’inhibiteurs de kinases hôtes pour traiter les maladies infectieuses |
CN103153994B (zh) * | 2010-05-24 | 2016-02-10 | 罗切斯特大学 | 双环杂芳基激酶抑制剂及使用方法 |
-
2012
- 2012-12-18 FR FR1262275A patent/FR2999575A1/fr active Pending
-
2013
- 2013-12-18 US US14/653,570 patent/US9447093B2/en active Active
- 2013-12-18 EP EP13811495.4A patent/EP2953947A1/fr not_active Withdrawn
- 2013-12-18 JP JP2015548535A patent/JP2016505584A/ja active Pending
- 2013-12-18 WO PCT/EP2013/077224 patent/WO2014096093A1/fr active Application Filing
- 2013-12-18 CA CA2896209A patent/CA2896209A1/fr not_active Abandoned
Non-Patent Citations (1)
Title |
---|
STÉPHANIE GOURDAIN ET AL: "Development of DANDYs, New 3,5-Diaryl-7-azaindoles Demonstrating Potent DYRK1A Kinase Inhibitory Activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 56, no. 23, 12 December 2013 (2013-12-12), US, pages 9569 - 9585, XP055582476, ISSN: 0022-2623, DOI: 10.1021/jm401049v * |
Also Published As
Publication number | Publication date |
---|---|
US20150307492A1 (en) | 2015-10-29 |
FR2999575A1 (fr) | 2014-06-20 |
JP2016505584A (ja) | 2016-02-25 |
US9447093B2 (en) | 2016-09-20 |
WO2014096093A1 (fr) | 2014-06-26 |
CA2896209A1 (fr) | 2014-06-26 |
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