CU24316B1 - Nuevos derivados fosfatos de 1,2,3,4-tetraisoquinolina amida fenilo, métodos de preparación de los mismos y composiciones farmacéuticas que los contienen - Google Patents
Nuevos derivados fosfatos de 1,2,3,4-tetraisoquinolina amida fenilo, métodos de preparación de los mismos y composiciones farmacéuticas que los contienenInfo
- Publication number
- CU24316B1 CU24316B1 CUP2014000095A CU20140095A CU24316B1 CU 24316 B1 CU24316 B1 CU 24316B1 CU P2014000095 A CUP2014000095 A CU P2014000095A CU 20140095 A CU20140095 A CU 20140095A CU 24316 B1 CU24316 B1 CU 24316B1
- Authority
- CU
- Cuba
- Prior art keywords
- formula
- compounds
- preparation
- tetraisoquinolina
- phyphate
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 2
- 241000670727 Amida Species 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 108010090931 Proto-Oncogene Proteins c-bcl-2 Proteins 0.000 abstract 1
- 102000013535 Proto-Oncogene Proteins c-bcl-2 Human genes 0.000 abstract 1
- 206010041067 Small cell lung cancer Diseases 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000006909 anti-apoptosis Effects 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000002512 chemotherapy Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 230000003211 malignant effect Effects 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 208000000587 small cell lung carcinoma Diseases 0.000 abstract 1
Classifications
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- 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
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
- A61N5/00—Radiation therapy
- A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
- A61N5/00—Radiation therapy
- A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
- A61N2005/1092—Details
- A61N2005/1098—Enhancing the effect of the particle by an injected agent or implanted device
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Radiology & Medical Imaging (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
<p>Compuestos derivados de fosfatos de 1,2,3,4- tetraisoquinolina amida fenilo de fórmula (I):</p> <p>ESPACIO PARA FORMULA</p> <p>El método de preparación comprende una reacción de Heck, entre dos compuestos, para formar otro compuesto, cuyo aldehído se oxida, se acopla peptídicamente al compuesto de fórmula (VI) formando un compuesto cuyo éster se hidroliza, forma el ácido carboxílico o carboxilato correspondiente, se convierte en un derivado de ácido, se acopla con una amina NHR3R4, reacciona con un derivado fosfato y se hidroliza o hidrogenoliza. Dichos compuestos poseen solubilidad muy superior a los compuestos de fórmula (I´), que inhiben la antiapoptosis causada por proteínas Bcl-2, por lo que son útiles contra cánceres quimio o radioresistentes, hemopatías malignas y cáncer de pulmón de células pequeñas.</p>
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1357259A FR3008979B1 (fr) | 2013-07-23 | 2013-07-23 | Nouveaux derives phosphates, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CU20140095A7 CU20140095A7 (es) | 2016-02-29 |
| CU24316B1 true CU24316B1 (es) | 2018-02-08 |
Family
ID=50288170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CUP2014000095A CU24316B1 (es) | 2013-07-23 | 2014-07-23 | Nuevos derivados fosfatos de 1,2,3,4-tetraisoquinolina amida fenilo, métodos de preparación de los mismos y composiciones farmacéuticas que los contienen |
Country Status (48)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| FR3008976A1 (fr) * | 2013-07-23 | 2015-01-30 | Servier Lab | "nouveaux derives d'indolizine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent" |
| FR3008977A1 (fr) | 2013-07-23 | 2015-01-30 | Servier Lab | Nouveaux derives d'isoindoline ou d'isoquinoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| UY37316A (es) * | 2016-07-07 | 2018-01-31 | Servier Lab | Dispersión sólida farmacéutica de un inhibidor de bcl-2, composiciones farmacéuticas de ésta, y usos para el tratamiento de cáncer |
| CR20220452A (es) * | 2016-07-22 | 2022-10-27 | Novartis Ag | COMBINACIÓN DE UN INHIBIDOR DE BCL-2 Y UN INHIBIDOR DE MCL1, USOS Y COMPOSICIONES FARMACÉUTICAS DE ESTOS (Divisional del Expediente 2019-0022) |
| WO2018015526A1 (en) | 2016-07-22 | 2018-01-25 | Les Laboratoires Servier | Combination of a bcl-2 inhibitor and a mcl-1 inhibitor, uses and pharmaceutical compositions thereof |
| WO2018158225A1 (en) | 2017-02-28 | 2018-09-07 | Les Laboratoires Servier | Combination of a bcl-2 inhibitor and a mdm2 inhibitor, uses and pharmaceutical compositions thereof |
| EA039621B1 (ru) * | 2017-06-09 | 2022-02-17 | Ле Лаборатуар Сервье | Комбинация bcl-2 ингибитора и mcl-1 ингибитора, их применения и фармацевтические композиции |
| TWI672302B (zh) * | 2017-07-06 | 2019-09-21 | 法商施維雅藥廠 | Bcl-2抑制劑之新結晶型、其製備方法及含其之醫藥組合物 |
| FR3072679B1 (fr) * | 2017-10-25 | 2020-10-30 | Servier Lab | Nouveaux derives macrocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CA3089566A1 (en) | 2018-01-31 | 2019-08-08 | Deciphera Pharmaceuticals, Llc | Combination therapy for the treatment of gastrointestinal stromal tumors |
| WO2021030405A1 (en) | 2019-08-12 | 2021-02-18 | Deciphera Pharmaceuticals, Llc | Ripretinib for treating gastrointestinal stromal tumors |
| JP2022544234A (ja) | 2019-08-12 | 2022-10-17 | デシフェラ・ファーマシューティカルズ，エルエルシー | 胃腸間質腫瘍を治療するためのリプレチニブ |
| CN110606860B (zh) | 2019-09-29 | 2021-12-10 | 上海勋和医药科技有限公司 | 一种吡啶磺酰胺磷酸酯类化合物、其制备方法及其用途 |
| EP4084778B1 (en) | 2019-12-30 | 2023-11-01 | Deciphera Pharmaceuticals, LLC | Amorphous kinase inhibitor formulations and methods of use thereof |
| KR20220123058A (ko) | 2019-12-30 | 2022-09-05 | 데시페라 파마슈티칼스, 엘엘씨. | 1-(4-브로모-5-(1-에틸-7-(메틸아미노)-2-옥소-1,2-디히드로-1,6-나프티리딘-3-일)-2-플루오로페닐)-3-페닐우레아의 조성물 |
| TW202302585A (zh) * | 2021-03-12 | 2023-01-16 | 美商伊爾治療學股份有限公司 | 具有四氫吲哚－１－甲醯胺作為ｂｃｌ－２抑制劑之化合物 |
| WO2023057394A1 (en) | 2021-10-04 | 2023-04-13 | Forx Therapeutics Ag | N,n-dimethyl-4-(7-(n-(1-methylcyclopropyl)sulfamoyl)-imidazo[1,5-a]pyridin-5-yl)piperazine-1-carboxamide derivatives and the corresponding pyrazolo[1,5-a]pyridine derivatives as parg inhibitors for the treatment of cancer |
| WO2023225359A1 (en) | 2022-05-20 | 2023-11-23 | Novartis Ag | Antibody-drug conjugates of antineoplastic compounds and methods of use thereof |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
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| CA2484209C (en) * | 2002-05-03 | 2013-06-11 | Exelixis, Inc. | Protein kinase modulators and methods of use |
| AU2003249713A1 (en) * | 2002-07-03 | 2004-01-23 | Axys Pharmaceuticals, Inc. | 3,4-dihydroisoquinolin-1-one derivatives as inducers of apoptosis |
| GB0224557D0 (en) * | 2002-10-22 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
| CA2631777A1 (en) * | 2005-12-22 | 2007-07-05 | Wyeth | Substituted isoquinoline-1,3(2h,4h)-diones, 1-thioxo-1,4-dihydro-2h-isoquinoline-3-ones and 1,4-dihydro-3(2h)-isoquinolones and use thereof as kinase inhibitor |
| US7902218B2 (en) | 2006-12-12 | 2011-03-08 | Bristol-Myers Squibb Company | Substituted tetrahydroisoquinolines as β-secretase inhibitors |
| KR101511074B1 (ko) * | 2007-04-16 | 2015-04-13 | 애브비 인코포레이티드 | 7-치환된 인돌 Ｍｃｌ-1 억제제 |
| BRPI0811145A2 (pt) * | 2007-05-22 | 2014-12-23 | Astellas Pharma Inc | Composto tetraidroisoquinolina 1-substituído |
| JP5496915B2 (ja) * | 2008-02-13 | 2014-05-21 | シージーアイ ファーマシューティカルズ，インコーポレーテッド | ６−アリール−イミダゾ［１，２−ａ］ピラジン誘導体、その製造方法、及びその使用方法 |
| US8232273B2 (en) * | 2008-12-19 | 2012-07-31 | Genentech, Inc. | Heterocyclic compounds and methods of use |
| TWI520960B (zh) * | 2010-05-26 | 2016-02-11 | 艾伯維有限公司 | 用於治療癌症及免疫及自體免疫疾病之細胞凋亡誘導劑 |
| US20120301080A1 (en) | 2011-05-23 | 2012-11-29 | Senko Advanced Components, Inc. | True one piece housing fiber optic adapter |
| CN104136429A (zh) | 2011-12-23 | 2014-11-05 | 诺华股份有限公司 | 用于抑制bcl2与结合配偶体相互作用的化合物 |
| CA2859862A1 (en) | 2011-12-23 | 2013-06-27 | Novartis Ag | Compounds for inhibiting the interaction of bcl2 with binding partners |
| CN104125954A (zh) | 2011-12-23 | 2014-10-29 | 诺华股份有限公司 | 用于抑制bcl2与结合配偶体相互作用的化合物 |
| MX2014007725A (es) | 2011-12-23 | 2015-01-12 | Novartis Ag | Compuestos para inhibir la interaccion de bcl2 con los componentes de enlace. |
| AU2012355624A1 (en) | 2011-12-23 | 2014-07-17 | Novartis Ag | Compounds for inhibiting the interaction of BCL2 with binding partners |
| CN103177906A (zh) | 2011-12-26 | 2013-06-26 | 西门子公司 | 用于中压开关设备的断路器 |
| ITPR20110103A1 (it) | 2011-12-27 | 2013-06-28 | G E A F S R L | Metodo e apparato per la sterilizzazione di una soluzione liquida mediante radio frequenza |
| US9114953B2 (en) | 2011-12-29 | 2015-08-25 | Inventio Ag | Emergency operation of elevators based on an indicated emergency condition |
| CN204345829U (zh) | 2012-01-24 | 2015-05-20 | 丹佛斯电力电子有限公司 | 除湿器和包括该除湿器的除湿系统 |
| FR2986002B1 (fr) * | 2012-01-24 | 2014-02-21 | Servier Lab | Nouveaux derives d'indolizine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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2013
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2014
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- 2016-07-18 CY CY20161100696T patent/CY1117834T1/el unknown
- 2016-09-20 HR HRP20161202TT patent/HRP20161202T8/hr unknown
- 2016-12-23 KR KR1020160177980A patent/KR20170001694A/ko not_active Application Discontinuation
-
2017
- 2017-02-06 US US15/425,119 patent/US20170143746A1/en not_active Abandoned
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