CA3066009A1 - Pyridoquinazoline derivatives useful as protein kinase inhibitors - Google Patents
Pyridoquinazoline derivatives useful as protein kinase inhibitors Download PDFInfo
- Publication number
- CA3066009A1 CA3066009A1 CA3066009A CA3066009A CA3066009A1 CA 3066009 A1 CA3066009 A1 CA 3066009A1 CA 3066009 A CA3066009 A CA 3066009A CA 3066009 A CA3066009 A CA 3066009A CA 3066009 A1 CA3066009 A1 CA 3066009A1
- Authority
- CA
- Canada
- Prior art keywords
- oxo
- pyrido
- carboxamide
- quinazoline
- branched
- 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.)
- Pending
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- 239000003909 protein kinase inhibitor Substances 0.000 title description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
- HWHQDEHKRIXJQN-UHFFFAOYSA-N quinazoline-6-carboxamide Chemical compound N1=CN=CC2=CC(C(=O)N)=CC=C21 HWHQDEHKRIXJQN-UHFFFAOYSA-N 0.000 claims description 26
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- 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
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical class COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 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
- 210000000440 neutrophil Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 229950005157 peficitinib Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000001175 peptic effect Effects 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
- 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
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000008707 rearrangement Effects 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
- 230000008054 signal transmission Effects 0.000 description 1
- 239000011734 sodium Substances 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
- 239000006190 sub-lingual tablet Substances 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
- 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ESP201730759 | 2017-06-01 | ||
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA3066009A1 true CA3066009A1 (en) | 2018-12-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3066009A Pending CA3066009A1 (en) | 2017-06-01 | 2018-05-31 | Pyridoquinazoline derivatives useful as protein kinase inhibitors |
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| EP (1) | EP3632912B1 (enExample) |
| JP (1) | JP7110335B2 (enExample) |
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| CN (1) | CN111247143B (enExample) |
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| CA (1) | CA3066009A1 (enExample) |
| CY (1) | CY1124087T1 (enExample) |
| DK (1) | DK3632912T3 (enExample) |
| EA (1) | EA037384B1 (enExample) |
| ES (1) | ES2881960T3 (enExample) |
| HR (1) | HRP20210814T1 (enExample) |
| HU (1) | HUE054792T2 (enExample) |
| LT (1) | LT3632912T (enExample) |
| MX (1) | MX385475B (enExample) |
| PL (1) | PL3632912T3 (enExample) |
| PT (1) | PT3632912T (enExample) |
| RS (1) | RS61833B1 (enExample) |
| SI (1) | SI3632912T1 (enExample) |
| SM (1) | SMT202100312T1 (enExample) |
| WO (1) | WO2018220252A1 (enExample) |
| ZA (1) | ZA201908372B (enExample) |
Families Citing this family (1)
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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 |
Family Cites Families (6)
| 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 |
| EP0944628B1 (en) * | 1996-11-26 | 2002-06-05 | American Cyanamid Company | Hetero-biaryl-pyridoquinazolinone derivatives as anti-cancer agents |
| 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 |
| US11001581B2 (en) | 2014-03-20 | 2021-05-11 | The Johns Hopkins University and Lieber Institute, Inc. | Compounds which inhibit RNA polymerase, compositions including such compounds, and their use |
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2018
- 2018-05-31 MX MX2019014436A patent/MX385475B/es unknown
- 2018-05-31 SM SM20210312T patent/SMT202100312T1/it unknown
- 2018-05-31 SI SI201830289T patent/SI3632912T1/sl unknown
- 2018-05-31 AU AU2018278283A patent/AU2018278283B2/en active Active
- 2018-05-31 PL PL18759146T patent/PL3632912T3/pl unknown
- 2018-05-31 DK DK18759146.6T patent/DK3632912T3/da active
- 2018-05-31 EP EP18759146.6A patent/EP3632912B1/en active Active
- 2018-05-31 US US16/615,867 patent/US11021479B2/en active Active
- 2018-05-31 PT PT187591466T patent/PT3632912T/pt unknown
- 2018-05-31 HR HRP20210814TT patent/HRP20210814T1/hr unknown
- 2018-05-31 RS RS20210545A patent/RS61833B1/sr unknown
- 2018-05-31 JP JP2020516962A patent/JP7110335B2/ja active Active
- 2018-05-31 KR KR1020197038842A patent/KR102629854B1/ko active Active
- 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
- 2018-05-31 HU HUE18759146A patent/HUE054792T2/hu unknown
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2019
- 2019-12-13 ZA ZA2019/08372A patent/ZA201908372B/en unknown
-
2021
- 2021-05-20 CY CY20211100437T patent/CY1124087T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RS61833B1 (sr) | 2021-06-30 |
| EA201992793A1 (ru) | 2020-03-26 |
| EA037384B1 (ru) | 2021-03-23 |
| HRP20210814T1 (hr) | 2021-06-25 |
| 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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