EA037384B1 - Ингибиторы протеинкиназ - Google Patents
Ингибиторы протеинкиназ Download PDFInfo
- Publication number
- EA037384B1 EA037384B1 EA201992793A EA201992793A EA037384B1 EA 037384 B1 EA037384 B1 EA 037384B1 EA 201992793 A EA201992793 A EA 201992793A EA 201992793 A EA201992793 A EA 201992793A EA 037384 B1 EA037384 B1 EA 037384B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- quinazoline
- pyrido
- oxo
- carboxamide
- cyclohexyl
- Prior art date
Links
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
- 239000003909 protein kinase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
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- 101000970023 Homo sapiens NUAK family SNF1-like kinase 1 Proteins 0.000 claims description 28
- -1 N-cyclohexyl-2-cyclopropyl-11-oxo-11H-pyrido [2,1-b] quinazoline-6-carboxyamide Chemical compound 0.000 claims description 28
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- HWHQDEHKRIXJQN-UHFFFAOYSA-N quinazoline-6-carboxamide Chemical compound N1=CN=CC2=CC(C(=O)N)=CC=C21 HWHQDEHKRIXJQN-UHFFFAOYSA-N 0.000 claims description 20
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052731 fluorine Inorganic materials 0.000 claims description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
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- 230000003436 cytoskeletal effect Effects 0.000 description 1
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
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- 230000008482 dysregulation Effects 0.000 description 1
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- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000002825 functional assay Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000007274 generation of a signal involved in cell-cell signaling Effects 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 231100001252 long-term toxicity Toxicity 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004066 metabolic change Effects 0.000 description 1
- 230000006609 metabolic stress Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- OOKUTMZSIGOCSB-UHFFFAOYSA-N methyl 2-amino-5-(4-fluorophenyl)benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC(C=2C=CC(F)=CC=2)=C1 OOKUTMZSIGOCSB-UHFFFAOYSA-N 0.000 description 1
- PNNRKISKHNTAHL-UHFFFAOYSA-N methyl 2-amino-5-thiophen-2-ylbenzoate Chemical compound C1=C(N)C(C(=O)OC)=CC(C=2SC=CC=2)=C1 PNNRKISKHNTAHL-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 230000009437 off-target effect Effects 0.000 description 1
- 108091008819 oncoproteins Proteins 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
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- 230000008506 pathogenesis Effects 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 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
- 230000035939 shock Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 108091006106 transcriptional activators Proteins 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
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- 238000007738 vacuum evaporation Methods 0.000 description 1
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- 239000008096 xylene 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
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24C—DOMESTIC STOVES OR RANGES ; DETAILS OF DOMESTIC STOVES OR RANGES, OF GENERAL APPLICATION
- F24C7/00—Stoves or ranges heated by electric energy
- F24C7/08—Arrangement or mounting of control or safety devices
- F24C7/082—Arrangement or mounting of control or safety devices on ranges, e.g. control panels, illumination
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24C—DOMESTIC STOVES OR RANGES ; DETAILS OF DOMESTIC STOVES OR RANGES, OF GENERAL APPLICATION
- F24C7/00—Stoves or ranges heated by electric energy
- F24C7/08—Arrangement or mounting of control or safety devices
- F24C7/087—Arrangement or mounting of control or safety devices of electric circuits regulating heat
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES201730759 | 2017-06-01 | ||
| PCT/ES2018/070396 WO2018220252A1 (es) | 2017-06-01 | 2018-05-31 | Derivados de piridoquinazolina eficaces como inhibidores de proteína quinasa |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201992793A1 EA201992793A1 (ru) | 2020-03-26 |
| EA037384B1 true EA037384B1 (ru) | 2021-03-23 |
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| RS (1) | RS61833B1 (enExample) |
| SI (1) | SI3632912T1 (enExample) |
| SM (1) | SMT202100312T1 (enExample) |
| WO (1) | WO2018220252A1 (enExample) |
| ZA (1) | ZA201908372B (enExample) |
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| JP7525609B2 (ja) | 2020-01-31 | 2024-07-30 | エルジー エナジー ソリューション リミテッド | 多層構造の無機物層を含む分離膜一体型電極の製造方法及びそれによる分離膜一体型電極 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998023617A1 (en) * | 1996-11-26 | 1998-06-04 | American Cyanamid Company | Hetero-biaryl-pyridoquinazolinone derivatives as anti-cancer agents |
| WO2015143293A1 (en) * | 2014-03-20 | 2015-09-24 | The Johns Hopkins University | Compounds which inhibit rna polymerase, compositions including such compounds, and their use |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4551460A (en) | 1982-05-10 | 1985-11-05 | Hoffmann-La Roche Inc. | Pyrido[2,1-b]quinazoline derivatives useful as agents for treatment of allergic conditions and vascular disorders involving thrombosis |
| US20050171172A1 (en) * | 2003-11-13 | 2005-08-04 | Ambit Biosciences Corporation | Amide derivatives as PDGFR modulators |
| AU2008345225A1 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| KR101361027B1 (ko) | 2008-11-28 | 2014-02-11 | 코와 가부시키가이샤 | 피리딘-3-카르복시아미드 유도체 |
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2018
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- 2018-05-31 ES ES18759146T patent/ES2881960T3/es active Active
- 2018-05-31 WO PCT/ES2018/070396 patent/WO2018220252A1/es not_active Ceased
- 2018-05-31 LT LTEP18759146.6T patent/LT3632912T/lt unknown
- 2018-05-31 EA EA201992793A patent/EA037384B1/ru unknown
- 2018-05-31 CN CN201880048531.4A patent/CN111247143B/zh active Active
- 2018-05-31 CA CA3066009A patent/CA3066009A1/en active Pending
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- 2019-12-13 ZA ZA2019/08372A patent/ZA201908372B/en unknown
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998023617A1 (en) * | 1996-11-26 | 1998-06-04 | American Cyanamid Company | Hetero-biaryl-pyridoquinazolinone derivatives as anti-cancer agents |
| WO2015143293A1 (en) * | 2014-03-20 | 2015-09-24 | The Johns Hopkins University | Compounds which inhibit rna polymerase, compositions including such compounds, and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| RS61833B1 (sr) | 2021-06-30 |
| EA201992793A1 (ru) | 2020-03-26 |
| HRP20210814T1 (hr) | 2021-06-25 |
| CA3066009A1 (en) | 2018-12-06 |
| CN111247143B (zh) | 2022-07-05 |
| SMT202100312T1 (it) | 2021-07-12 |
| EP3632912B1 (en) | 2021-03-17 |
| JP7110335B2 (ja) | 2022-08-01 |
| ES2881960T3 (es) | 2021-11-30 |
| JP2020521817A (ja) | 2020-07-27 |
| MX385475B (es) | 2025-03-18 |
| CN111247143A (zh) | 2020-06-05 |
| US20200148676A1 (en) | 2020-05-14 |
| US11021479B2 (en) | 2021-06-01 |
| DK3632912T3 (da) | 2021-05-10 |
| MX2019014436A (es) | 2020-02-10 |
| AU2018278283B2 (en) | 2021-06-17 |
| KR20200011990A (ko) | 2020-02-04 |
| SI3632912T1 (sl) | 2021-08-31 |
| KR102629854B1 (ko) | 2024-01-25 |
| CY1124087T1 (el) | 2022-05-27 |
| PL3632912T3 (pl) | 2021-09-06 |
| LT3632912T (lt) | 2021-06-10 |
| PT3632912T (pt) | 2021-06-02 |
| HUE054792T2 (hu) | 2021-09-28 |
| EP3632912A1 (en) | 2020-04-08 |
| WO2018220252A1 (es) | 2018-12-06 |
| AU2018278283A1 (en) | 2019-12-19 |
| BR112019024892A2 (pt) | 2020-06-16 |
| ZA201908372B (en) | 2021-04-28 |
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