HUE024989T2 - Azaindole derivatives as ABI and SRC protein kinase inhibitors - Google Patents
Azaindole derivatives as ABI and SRC protein kinase inhibitors Download PDFInfo
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- HUE024989T2 HUE024989T2 HUE10710439A HUE10710439A HUE024989T2 HU E024989 T2 HUE024989 T2 HU E024989T2 HU E10710439 A HUE10710439 A HU E10710439A HU E10710439 A HUE10710439 A HU E10710439A HU E024989 T2 HUE024989 T2 HU E024989T2
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- 239000003112 inhibitor Substances 0.000 title claims description 50
- 102000001253 Protein Kinase Human genes 0.000 title claims description 30
- 108060006633 protein kinase Proteins 0.000 title claims description 30
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- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 229910010277 boron hydride Inorganic materials 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 201000010902 chronic myelomonocytic leukemia Diseases 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 238000012866 crystallographic experiment Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- IZCSREAMZDZVFW-UHFFFAOYSA-N ethyl 5-amino-1,3-thiazole-2-carboxylate Chemical compound CCOC(=O)C1=NC=C(N)S1 IZCSREAMZDZVFW-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 102000037865 fusion proteins Human genes 0.000 description 1
- 108020001507 fusion proteins Proteins 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 229940080856 gleevec Drugs 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000000021 kinase assay Methods 0.000 description 1
- 230000036212 malign transformation Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- IHGOYDMXENEUOO-UHFFFAOYSA-N methyl 2-aminopyrimidine-4-carboxylate Chemical compound COC(=O)C1=CC=NC(N)=N1 IHGOYDMXENEUOO-UHFFFAOYSA-N 0.000 description 1
- PYQRUDYLXHRTQU-UHFFFAOYSA-N methyl 4-aminopyrimidine-2-carboxylate Chemical compound COC(=O)C1=NC=CC(N)=N1 PYQRUDYLXHRTQU-UHFFFAOYSA-N 0.000 description 1
- FCDMJPPRJSFFRX-UHFFFAOYSA-N methyl 5-[(2-fluoro-6-methoxybenzoyl)amino]-1h-pyrrolo[2,3-b]pyridine-2-carboxylate Chemical compound C=1N=C2NC(C(=O)OC)=CC2=CC=1NC(=O)C1=C(F)C=CC=C1OC FCDMJPPRJSFFRX-UHFFFAOYSA-N 0.000 description 1
- PGQWALGGBUYLQF-UHFFFAOYSA-N methyl 5-[[2-methyl-5-[[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)benzoyl]amino]phenyl]methylamino]-1h-pyrrolo[2,3-b]pyridine-2-carboxylate Chemical compound C=1N=C2NC(C(=O)OC)=CC2=CC=1NCC(C(=CC=1)C)=CC=1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1N1C=NC(C)=C1 PGQWALGGBUYLQF-UHFFFAOYSA-N 0.000 description 1
- NXIWKVKEGODGND-UHFFFAOYSA-N methyl 5-[[5-[[4-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]-3-(trifluoromethyl)benzoyl]amino]-2-methylbenzoyl]amino]-1h-pyrrolo[2,3-b]pyridine-2-carboxylate Chemical compound C=1N=C2NC(C(=O)OC)=CC2=CC=1NC(=O)C(C(=CC=1)C)=CC=1NC(=O)C(C=C1C(F)(F)F)=CC=C1CN1CCC(N(C)C)C1 NXIWKVKEGODGND-UHFFFAOYSA-N 0.000 description 1
- OHIHEJTUXNQOPM-UHFFFAOYSA-N methyl 6-aminopyridine-2-carboxylate Chemical compound COC(=O)C1=CC=CC(N)=N1 OHIHEJTUXNQOPM-UHFFFAOYSA-N 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- AVAWMINJNRAQFS-UHFFFAOYSA-N n,n-dimethylpyrrolidin-3-amine Chemical compound CN(C)C1CCNC1 AVAWMINJNRAQFS-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- JCSQXEINQFERDM-UHFFFAOYSA-N n-benzyl-1h-indazol-3-amine Chemical compound N=1NC2=CC=CC=C2C=1NCC1=CC=CC=C1 JCSQXEINQFERDM-UHFFFAOYSA-N 0.000 description 1
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 201000004931 neurofibromatosis Diseases 0.000 description 1
- 230000036963 noncompetitive effect Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 238000009521 phase II clinical trial Methods 0.000 description 1
- 210000004214 philadelphia chromosome Anatomy 0.000 description 1
- 208000015768 polyposis Diseases 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 description 1
- UTEQROVYZDJSOO-UHFFFAOYSA-N quinoxaline-6-carbonyl chloride Chemical compound N1=CC=NC2=CC(C(=O)Cl)=CC=C21 UTEQROVYZDJSOO-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 150000003667 tyrosine derivatives Chemical class 0.000 description 1
- 239000003643 water by type Substances 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20227909P | 2009-02-12 | 2009-02-12 | |
| FR0900631A FR2941948B1 (fr) | 2009-02-12 | 2009-02-12 | Derives d'azaindoles en tant qu'inhibiteur des proteines kinases abl et src |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUE024989T2 true HUE024989T2 (en) | 2016-01-28 |
Family
ID=40886859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE10710439A HUE024989T2 (en) | 2009-02-12 | 2010-02-12 | Azaindole derivatives as ABI and SRC protein kinase inhibitors |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8580815B2 (enExample) |
| EP (1) | EP2396325B1 (enExample) |
| JP (1) | JP5583698B2 (enExample) |
| AU (1) | AU2010212560B2 (enExample) |
| CA (1) | CA2751478A1 (enExample) |
| DK (1) | DK2396325T3 (enExample) |
| ES (1) | ES2540962T3 (enExample) |
| FR (1) | FR2941948B1 (enExample) |
| HR (1) | HRP20150697T8 (enExample) |
| HU (1) | HUE024989T2 (enExample) |
| PL (1) | PL2396325T3 (enExample) |
| PT (1) | PT2396325E (enExample) |
| SI (1) | SI2396325T1 (enExample) |
| SM (1) | SMT201500175B (enExample) |
| WO (1) | WO2010092489A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ME03000B (me) * | 2012-12-21 | 2018-10-20 | Plexxikon Inc | Jedinjenja i metode modulacije kinaze i povezane indikacije |
| FR3000493A1 (fr) * | 2012-12-28 | 2014-07-04 | Oribase Pharma | Nouveaux inhibiteurs de proteines kinases |
| FR3000494B1 (fr) * | 2012-12-28 | 2015-08-21 | Oribase Pharma | Nouveaux derives d'azaindoles en tant qu'inhibiteurs de proteines kinases |
| FR3000492B1 (fr) * | 2012-12-28 | 2015-09-11 | Oribase Pharma | Nouveaux derives azaindole en tant qu'inhibiteurs multikinases |
| US10722484B2 (en) | 2016-03-09 | 2020-07-28 | K-Gen, Inc. | Methods of cancer treatment |
| MA49014A (fr) * | 2017-03-21 | 2020-02-05 | Arbutus Biopharma Corp | Dihydroindène-4-carboxamides substitués, leurs analogues et procédés d'utilisation correspondant |
| AU2021263383A1 (en) | 2020-04-29 | 2022-11-24 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| CN111943947B (zh) * | 2020-07-24 | 2021-04-30 | 重庆文理学院 | 1H-吡咯[2,3-b]吡啶衍生物及其合成方法与应用 |
| CA3196620A1 (en) | 2020-10-05 | 2022-04-14 | Enliven Therapeutics, Inc. | 5- and 6-azaindole compounds for inhibition of bcr-abl tyrosine kinases |
| WO2022076973A1 (en) * | 2020-10-05 | 2022-04-14 | Enliven Therapeutics, Inc. | 7-azaindole compounds for inhibition of bcr-abl tyrosine kinases |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0330043D0 (en) * | 2003-12-24 | 2004-01-28 | Pharmacia Italia Spa | Pyrrolo [2,3-b] pyridine derivatives active as kinase inhibitors process for their preparation and pharmaceutical compositions comprising them |
| GB0330042D0 (en) | 2003-12-24 | 2004-01-28 | Pharmacia Italia Spa | Pyrrolo [2,3-b] pyridine derivatives active as kinase inhibitors process for their preparation and pharmaceutical compositions them |
| TW200616632A (en) * | 2004-06-17 | 2006-06-01 | Plexxikon Inc | Compounds modulating c-kit activity and uses therefor |
| US7361764B2 (en) | 2004-07-27 | 2008-04-22 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
| NZ553267A (en) | 2004-07-27 | 2010-09-30 | Sgx Pharmaceuticals Inc | Pyrrolo-pyridine kinase modulators |
| US7709645B2 (en) | 2004-07-27 | 2010-05-04 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
| WO2006104971A1 (en) * | 2005-03-28 | 2006-10-05 | Bristol-Myers Squibb Company | Atp competitive kinase inhibitors |
| BRPI0716477A2 (pt) | 2006-09-06 | 2014-03-18 | Hoffmann La Roche | Derivados heteroarila como inibidores de quinase protéica |
| JP5244118B2 (ja) * | 2006-11-10 | 2013-07-24 | ブリストル−マイヤーズ スクイブ カンパニー | 新規キナーゼ阻害剤 |
| WO2008144253A1 (en) * | 2007-05-14 | 2008-11-27 | Irm Llc | Protein kinase inhibitors and methods for using thereof |
| WO2009111278A2 (en) * | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | Raf inhibitor compounds and methods of use thereof |
| HUE035798T2 (en) * | 2008-11-03 | 2018-05-28 | Syntarga Bv | CC-1065 analogues and conjugates |
-
2009
- 2009-02-12 FR FR0900631A patent/FR2941948B1/fr not_active Expired - Fee Related
-
2010
- 2010-02-12 HR HRP20150697TT patent/HRP20150697T8/hr unknown
- 2010-02-12 AU AU2010212560A patent/AU2010212560B2/en not_active Ceased
- 2010-02-12 EP EP10710439.0A patent/EP2396325B1/en not_active Not-in-force
- 2010-02-12 PT PT107104390T patent/PT2396325E/pt unknown
- 2010-02-12 JP JP2011549698A patent/JP5583698B2/ja not_active Expired - Fee Related
- 2010-02-12 US US13/148,988 patent/US8580815B2/en not_active Expired - Fee Related
- 2010-02-12 WO PCT/IB2010/000593 patent/WO2010092489A1/en not_active Ceased
- 2010-02-12 HU HUE10710439A patent/HUE024989T2/en unknown
- 2010-02-12 ES ES10710439.0T patent/ES2540962T3/es active Active
- 2010-02-12 DK DK10710439.0T patent/DK2396325T3/en active
- 2010-02-12 CA CA2751478A patent/CA2751478A1/en not_active Abandoned
- 2010-02-12 SI SI201030964T patent/SI2396325T1/sl unknown
- 2010-02-12 PL PL10710439T patent/PL2396325T3/pl unknown
-
2015
- 2015-07-22 SM SM201500175T patent/SMT201500175B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US8580815B2 (en) | 2013-11-12 |
| ES2540962T3 (es) | 2015-07-15 |
| DK2396325T3 (en) | 2015-06-29 |
| EP2396325B1 (en) | 2015-04-01 |
| SI2396325T1 (sl) | 2015-08-31 |
| FR2941948A1 (fr) | 2010-08-13 |
| JP5583698B2 (ja) | 2014-09-03 |
| US20110312959A1 (en) | 2011-12-22 |
| PT2396325E (pt) | 2015-08-21 |
| AU2010212560B2 (en) | 2016-01-21 |
| FR2941948B1 (fr) | 2013-04-05 |
| HRP20150697T8 (xx) | 2015-11-06 |
| WO2010092489A1 (en) | 2010-08-19 |
| HRP20150697T1 (hr) | 2015-08-14 |
| AU2010212560A1 (en) | 2011-08-11 |
| JP2012517465A (ja) | 2012-08-02 |
| SMT201500175B (it) | 2015-09-07 |
| EP2396325A1 (en) | 2011-12-21 |
| CA2751478A1 (en) | 2010-08-19 |
| PL2396325T3 (pl) | 2015-10-30 |
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