RU2690853C2 - Производные изохинолинона, полезные для лечения рака - Google Patents
Производные изохинолинона, полезные для лечения рака Download PDFInfo
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- RU2690853C2 RU2690853C2 RU2017108909A RU2017108909A RU2690853C2 RU 2690853 C2 RU2690853 C2 RU 2690853C2 RU 2017108909 A RU2017108909 A RU 2017108909A RU 2017108909 A RU2017108909 A RU 2017108909A RU 2690853 C2 RU2690853 C2 RU 2690853C2
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- amino
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- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 15
- 201000011510 cancer Diseases 0.000 title claims abstract description 12
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- 150000004677 hydrates Chemical class 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 230000003993 interaction Effects 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 208000014018 liver neoplasm Diseases 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
- 230000008774 maternal effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
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- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- YSEORDDJWGLYRL-UHFFFAOYSA-N methyl 2-(3-hydroxyprop-1-ynyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C#CCO YSEORDDJWGLYRL-UHFFFAOYSA-N 0.000 description 1
- XYMZAFDNPJLOTP-UHFFFAOYSA-N methyl 2-bromo-4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C=C1Br XYMZAFDNPJLOTP-UHFFFAOYSA-N 0.000 description 1
- VSEYYEKRZNRECT-UHFFFAOYSA-N methyl 2-bromo-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC=C1Br VSEYYEKRZNRECT-UHFFFAOYSA-N 0.000 description 1
- SWGQITQOBPXVRC-UHFFFAOYSA-N methyl 2-bromobenzoate Chemical compound COC(=O)C1=CC=CC=C1Br SWGQITQOBPXVRC-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- 206010028537 myelofibrosis Diseases 0.000 description 1
- ZQGJEUVBUVKZKS-UHFFFAOYSA-N n,2-dimethylpropan-2-amine Chemical compound CNC(C)(C)C ZQGJEUVBUVKZKS-UHFFFAOYSA-N 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 239000012038 nucleophile Substances 0.000 description 1
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- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
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- 150000003016 phosphoric acids Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 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
- 230000019491 signal transduction Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
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- 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
- 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
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14306352.7 | 2014-09-02 | ||
| EP14306352 | 2014-09-02 | ||
| PCT/EP2015/070082 WO2016034642A1 (en) | 2014-09-02 | 2015-09-02 | Isoquinolinone derivatives useful in the treatment of cancer |
Publications (3)
| Publication Number | Publication Date |
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| RU2017108909A RU2017108909A (ru) | 2018-10-03 |
| RU2017108909A3 RU2017108909A3 (enExample) | 2018-12-13 |
| RU2690853C2 true RU2690853C2 (ru) | 2019-06-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| RU2017108909A RU2690853C2 (ru) | 2014-09-02 | 2015-09-02 | Производные изохинолинона, полезные для лечения рака |
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| EP (1) | EP3189051A1 (enExample) |
| JP (1) | JP2017525734A (enExample) |
| CN (1) | CN106795154B (enExample) |
| BR (1) | BR112017003651A2 (enExample) |
| MX (1) | MX2017002544A (enExample) |
| RU (1) | RU2690853C2 (enExample) |
| WO (1) | WO2016034642A1 (enExample) |
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|---|---|---|---|---|
| US10130623B2 (en) * | 2016-07-08 | 2018-11-20 | Rigel Pharmaceuticals, Inc. | Tyrosine kinase inhibitors |
| CN106699608A (zh) * | 2016-12-26 | 2017-05-24 | 常州大学 | 一种含有强吸电子基团的苯胍及其盐的制备方法 |
| CN111683976B (zh) | 2018-02-05 | 2022-11-18 | 生物辐射实验室股份有限公司 | 具有阴离子交换-疏水混合模式配体的色谱树脂 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA016152B1 (ru) * | 2005-09-30 | 2012-02-28 | Новартис Аг | 2-АМИНО-7,8-ДИГИДРО-6Н-ПИРИДО[4,3-d]ПИРИМИДИН-5-ОНЫ, СПОСОБ ИХ ПОЛУЧЕНИЯ, СПОСОБ ТЕРАПИИ С ИХ ПОМОЩЬЮ, КОМПОНЕНТ КОМПОЗИЦИИ, КОМПОЗИЦИЯ И ЛЕКАРСТВЕННОЕ СРЕДСТВО НА ИХ ОСНОВЕ, 2,4-ДИОКСОПИПЕРИДИНОВЫЕ СОЕДИНЕНИЯ ДЛЯ ИХ ПОЛУЧЕНИЯ |
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| EP2100894A1 (en) * | 2008-03-12 | 2009-09-16 | 4Sc Ag | Pyridopyrimidines used as Plk1 (polo-like kinase) inhibitors |
| WO2012102985A1 (en) | 2011-01-24 | 2012-08-02 | Glaxosmithkline Llc | Isoquinoline compounds and methods for treating hiv |
| HK1198365A1 (en) | 2011-09-20 | 2015-04-10 | F. Hoffmann-La Roche Ag | Imidazopyridine compounds, compositions and methods of use |
| JP6128133B2 (ja) * | 2012-01-23 | 2017-05-17 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｉｇｆ−１ｒ／ｉｒ阻害剤としての５，８−ジヒドロ−６ｈ−ピラゾロ［３，４−ｈ］キナゾリン |
| JP2015511245A (ja) * | 2012-02-23 | 2015-04-16 | アッヴィ・インコーポレイテッド | ピリドピリミジノン系キナーゼ阻害薬 |
| JP6553589B2 (ja) * | 2013-03-15 | 2019-07-31 | ダナ−ファーバー キャンサー インスティテュート，インコーポレイテッド | ピリミド−ジアゼピノン化合物および障害の治療方法 |
-
2015
- 2015-09-02 MX MX2017002544A patent/MX2017002544A/es unknown
- 2015-09-02 BR BR112017003651A patent/BR112017003651A2/pt not_active IP Right Cessation
- 2015-09-02 WO PCT/EP2015/070082 patent/WO2016034642A1/en not_active Ceased
- 2015-09-02 JP JP2017512003A patent/JP2017525734A/ja active Pending
- 2015-09-02 RU RU2017108909A patent/RU2690853C2/ru not_active IP Right Cessation
- 2015-09-02 EP EP15762963.5A patent/EP3189051A1/en not_active Withdrawn
- 2015-09-02 CN CN201580047253.7A patent/CN106795154B/zh not_active Expired - Fee Related
- 2015-09-02 US US15/507,941 patent/US9944641B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA016152B1 (ru) * | 2005-09-30 | 2012-02-28 | Новартис Аг | 2-АМИНО-7,8-ДИГИДРО-6Н-ПИРИДО[4,3-d]ПИРИМИДИН-5-ОНЫ, СПОСОБ ИХ ПОЛУЧЕНИЯ, СПОСОБ ТЕРАПИИ С ИХ ПОМОЩЬЮ, КОМПОНЕНТ КОМПОЗИЦИИ, КОМПОЗИЦИЯ И ЛЕКАРСТВЕННОЕ СРЕДСТВО НА ИХ ОСНОВЕ, 2,4-ДИОКСОПИПЕРИДИНОВЫЕ СОЕДИНЕНИЯ ДЛЯ ИХ ПОЛУЧЕНИЯ |
Non-Patent Citations (1)
| Title |
|---|
| FRESNEAU NATHALIE ET AL: "Synthesis of substituted diazino[c]quinolin-5(6H)-ones, diazino[c] isoquinolin-6(5H)-ones, diazino[c]naphthyridin-6(5H)-ones and diazino[c]naphthyridin-5(6H)-ones ", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol.69, no.26, 28.04.2013, pp.5393-5400, DOI: 10.1016/J.TET.2013.04.104. * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017525734A (ja) | 2017-09-07 |
| US9944641B2 (en) | 2018-04-17 |
| MX2017002544A (es) | 2017-07-19 |
| RU2017108909A3 (enExample) | 2018-12-13 |
| CN106795154A (zh) | 2017-05-31 |
| BR112017003651A2 (pt) | 2017-12-05 |
| RU2017108909A (ru) | 2018-10-03 |
| WO2016034642A1 (en) | 2016-03-10 |
| US20170240544A1 (en) | 2017-08-24 |
| EP3189051A1 (en) | 2017-07-12 |
| CN106795154B (zh) | 2019-07-05 |
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