MX2010013920A - Alcoholes alquinilicos como inhibidores de cinasas. - Google Patents
Alcoholes alquinilicos como inhibidores de cinasas.Info
- Publication number
- MX2010013920A MX2010013920A MX2010013920A MX2010013920A MX2010013920A MX 2010013920 A MX2010013920 A MX 2010013920A MX 2010013920 A MX2010013920 A MX 2010013920A MX 2010013920 A MX2010013920 A MX 2010013920A MX 2010013920 A MX2010013920 A MX 2010013920A
- Authority
- MX
- Mexico
- Prior art keywords
- mmol
- bromo
- esi
- amino
- mhz
- Prior art date
Links
- -1 Alkynyl alcohols Chemical class 0.000 title claims description 444
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 73
- 125000002947 alkylene group Chemical group 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000002500 ions Chemical class 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
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- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
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- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 18
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
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- 238000010992 reflux Methods 0.000 description 17
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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Families Citing this family (44)
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| CA2787785C (en) | 2010-01-28 | 2018-03-06 | President And Fellows Of Harvard College | Compositions and methods for enhancing proteasome activity |
| EP2796456A1 (en) * | 2010-12-09 | 2014-10-29 | Amgen Inc. | Bicyclic compounds as Pim inhibitors |
| CN103476768B (zh) | 2011-03-16 | 2015-07-08 | 弗·哈夫曼-拉罗切有限公司 | 6,5-杂环炔丙醇化合物及其用途 |
| EP2688886A1 (en) | 2011-03-22 | 2014-01-29 | Amgen Inc. | Azole compounds as pim inhibitors |
| WO2012135697A2 (en) * | 2011-03-30 | 2012-10-04 | H. Lee Moffitt Cancer Center & Research Institute Inc. | Novel rho kinase inhibitors and methods of use |
| WO2012154967A1 (en) | 2011-05-12 | 2012-11-15 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
| EP2551670A1 (en) | 2011-07-27 | 2013-01-30 | Merck Patent GmbH | NIK inhibitors cell-based assay |
| WO2013057944A1 (ja) | 2011-10-19 | 2013-04-25 | 興和株式会社 | 新規なスピロインドリン化合物、及びそれを含有する医薬 |
| BR112014019209A2 (pt) | 2012-02-17 | 2017-07-04 | Hoffmann La Roche | compostos tricíclicos e métodos de uso para os mesmos |
| US9849135B2 (en) | 2013-01-25 | 2017-12-26 | President And Fellows Of Harvard College | USP14 inhibitors for treating or preventing viral infections |
| TWI663166B (zh) | 2013-04-24 | 2019-06-21 | 健生藥品公司 | 新化合物 |
| RU2016110016A (ru) * | 2013-08-22 | 2017-09-27 | Ф. Хоффманн-Ля Рош Аг | Алкиниловые спирты и способы их применения |
| US20150057260A1 (en) * | 2013-08-22 | 2015-02-26 | Genentech, Inc. | Alkynyl alcohols and methods of use |
| TWI627173B (zh) * | 2013-09-26 | 2018-06-21 | 比利時商健生藥品公司 | 作為NIK抑制劑的新穎3-(1H-吡唑-4-基)-1H-吡咯并[2,3-c]吡啶衍生物 |
| TWI704146B (zh) * | 2013-09-26 | 2020-09-11 | 比利時商健生藥品公司 | 用作NIK抑制劑之新的1-(4-嘧啶基)-1H-吡唑並[3,2-c]吡啶衍生物 |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| HUE052099T2 (hu) | 2014-04-04 | 2021-04-28 | Iomet Pharma Ltd | Indol származékok felhasználásra az orvostudományban |
| KR101551313B1 (ko) | 2014-07-28 | 2015-09-09 | 충남대학교산학협력단 | 신규한 인덴 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 망막 질환의 예방 또는 치료용 약학적 조성물 |
| EP3209663B1 (en) * | 2014-10-23 | 2018-12-12 | Janssen Pharmaceutica N.V. | New pyrazolopyrimidine derivatives as nik inhibitors |
| US10323045B2 (en) * | 2014-10-23 | 2019-06-18 | Janssen Pharmaceutica Nv | Thienopyrimidine derivatives as NIK inhibitors |
| ES2718557T3 (es) * | 2014-10-23 | 2019-07-02 | Janssen Pharmaceutica Nv | Nuevos compuestos como inhibidores de nik |
| KR102499862B1 (ko) * | 2014-10-23 | 2023-02-13 | 얀센 파마슈티카 엔.브이. | Nik 억제제로서의 신규 피라졸 유도체 |
| EP3262035A1 (en) * | 2015-02-25 | 2018-01-03 | F. Hoffmann-La Roche AG | Alkynyl alcohols and methods of use |
| CN107973791B (zh) * | 2015-04-29 | 2020-04-07 | 南京圣和药业股份有限公司 | 稠环或三环芳基嘧啶化合物用作激酶抑制剂 |
| SI3405196T1 (sl) * | 2016-01-22 | 2020-03-31 | Janssen Pharmaceutica Nv | Novi substituirani derivati cianoindolina kot inhibitorji NIK |
| KR102720461B1 (ko) * | 2016-01-22 | 2024-10-21 | 잔센파마슈티카엔.브이. | Nik 억제제로서의 신규 6원 헤테로방향족 치환된 시아노인돌린 유도체 |
| CN105769871A (zh) * | 2016-03-03 | 2016-07-20 | 东北师范大学 | Nik蛋白激酶抑制剂作为制备治疗肝病的药物的应用 |
| EA037358B1 (ru) * | 2016-03-10 | 2021-03-17 | Янссен Фармасьютика Нв | Новые замещённые производные цианиндолина в качестве nik-ингибиторов |
| CA3027416A1 (en) | 2016-06-30 | 2018-01-04 | Janssen Pharmaceutica Nv | Heteroaromatic derivatives as nik inhibitors |
| ES2837157T3 (es) | 2016-06-30 | 2021-06-29 | Janssen Pharmaceutica Nv | Derivados de cianoindolina como inhibidores de NIK |
| WO2018037058A1 (en) * | 2016-08-24 | 2018-03-01 | F. Hoffmann-La Roche Ag | 2-azabicyclo[3.1.0]hexan-3-one derivatives and methods of use |
| EP3504206B1 (en) | 2016-08-24 | 2022-03-23 | F. Hoffmann-La Roche AG | 2-azabicyclo[3.1.0]hexan-3-one derivatives and methods of use |
| US10858319B2 (en) | 2016-10-03 | 2020-12-08 | Iomet Pharma Ltd. | Indole derivatives for use in medicine |
| CA3063288A1 (en) | 2017-05-12 | 2018-11-15 | Mavalon Therapeutics Limited | Substituted heterocyclic compounds as allosteric modulators of group ii metabotropic glutamate receptors |
| CN109810110B (zh) * | 2017-11-22 | 2023-01-24 | 中国科学院上海药物研究所 | 一种具有2-氨基嘧啶结构的化合物,其制备方法和用途 |
| WO2019183145A1 (en) | 2018-03-20 | 2019-09-26 | Plexxikon Inc. | Compounds and methods for ido and tdo modulation, and indications therefor |
| RS66105B1 (sr) * | 2019-05-31 | 2024-11-29 | Janssen Pharmaceutica Nv | Inhibitori malih molekula nf-kb koji indukuju kinazu |
| EP3782702A1 (en) * | 2019-08-21 | 2021-02-24 | AC BioScience SA | Compounds and use thereof for the treatment of infectious diseases and cancer |
| AU2021286728A1 (en) * | 2020-06-12 | 2023-01-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of APOL1 and use of the same |
| CN113831325A (zh) * | 2020-06-23 | 2021-12-24 | 沈阳药科大学 | 新型吲哚类衍生物及其制备方法和应用 |
| CN111960983A (zh) * | 2020-08-31 | 2020-11-20 | 南通大学 | 一种n-甲基-3-(1-甲基吡咯烷-3-基)丙-1-胺及其合成方法 |
| CN112194609B (zh) * | 2020-10-22 | 2022-11-04 | 西北农林科技大学 | 3,3-二取代氧化吲哚类化合物及其制备方法与用途 |
| CN112174938A (zh) * | 2020-10-27 | 2021-01-05 | 浙江工业大学 | 4-吲哚-2-氨基嘧啶类化合物及其应用 |
| CN115215861B (zh) * | 2021-04-16 | 2024-03-15 | 上海翊石医药科技有限公司 | 一种芳杂环取代的炔烃类化合物及其制备方法和用途 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK429884A (da) * | 1983-10-07 | 1985-04-08 | Hoffmann La Roche | Heterocycliske forbindelser |
| GB8714537D0 (en) * | 1987-06-22 | 1987-07-29 | Ici Plc | Pyrazine derivatives |
| GB2208860B (en) * | 1987-08-20 | 1991-10-09 | Ici Plc | Pyrimidine derivatives |
| GB9016783D0 (en) * | 1989-09-01 | 1990-09-12 | Ici Plc | Agrochemical compositions |
| CA2167673C (en) * | 1993-07-21 | 2004-09-21 | Akihiro Tanaka | Condensed benzazepine derivative and pharmaceutical composition thereof |
| EP0746554A1 (en) * | 1994-02-23 | 1996-12-11 | Pfizer Inc. | 4-heterocyclyl-substituted quinazoline derivatives, processes for their preparation and their use as anti-cancer agents |
| US6063930A (en) * | 1996-04-03 | 2000-05-16 | Merck & Co., Inc. | Substituted imidazole compounds useful as farnesyl-protein transferase inhibitors |
| ZA986729B (en) * | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitors of tyrosine kinases |
| GB9716446D0 (en) * | 1997-08-05 | 1997-10-08 | Agrevo Uk Ltd | Fungicides |
| US6576656B1 (en) * | 1998-08-20 | 2003-06-10 | Sumitomo Pharmaceuticals Co., Ltd. | Oxindole derivative |
| UA71945C2 (en) * | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
| JP2002053561A (ja) * | 1999-12-08 | 2002-02-19 | Sumitomo Chem Co Ltd | ジフルオロメチルトリアゾロン化合物、その用途およびその製造中間体 |
| US6313310B1 (en) * | 1999-12-15 | 2001-11-06 | Hoffmann-La Roche Inc. | 4-and 5-alkynyloxindoles and 4-and 5-alkenyloxindoles |
| US20020019527A1 (en) * | 2000-04-27 | 2002-02-14 | Wei-Bo Wang | Substituted phenyl farnesyltransferase inhibitors |
| US20020115640A1 (en) * | 2000-11-30 | 2002-08-22 | Claiborne Akiyo K. | Farnesyltransferase inhibitors |
| US7211595B2 (en) * | 2000-11-30 | 2007-05-01 | Abbott Laboratories | Farnesyltransferase inhibitors |
| US6504034B2 (en) * | 2001-01-23 | 2003-01-07 | Hoffmann-La Roche Inc. | Naphthostyrils |
| GB0123589D0 (en) * | 2001-10-01 | 2001-11-21 | Syngenta Participations Ag | Organic compounds |
| JP4559087B2 (ja) * | 2002-04-26 | 2010-10-06 | イーライ リリー アンド カンパニー | タキキニン受容体アンタゴニストとしてのトリアゾール誘導体 |
| PT1501808E (pt) * | 2002-04-26 | 2008-09-26 | Lilly Co Eli | Antagonistas de receptores taquiquininas |
| US20030216441A1 (en) * | 2002-05-10 | 2003-11-20 | Gwaltney Stephen L. | Farnesyltransferase inhibitors |
| DE10229762A1 (de) * | 2002-07-03 | 2004-01-22 | Aventis Pharma Deutschland Gmbh | Pyrazoloisoquinolinenderivaten zur Inhibierung von NFkappaB-induzierende Kinase |
| US20050035498A1 (en) * | 2003-08-13 | 2005-02-17 | Stevens Randal Alan | Methods of making a negative hearing aid mold |
| US20070167426A1 (en) * | 2004-06-02 | 2007-07-19 | Schering Corporation | Compounds for the treatment of inflammatory disorders and microbial diseases |
| PE20060426A1 (es) * | 2004-06-02 | 2006-06-28 | Schering Corp | DERIVADOS DE ACIDO TARTARICO COMO INHIBIDORES DE MMPs, ADAMs, TACE Y TNF-alfa |
| US7396852B2 (en) * | 2005-11-16 | 2008-07-08 | Xerox Corporation | Compound having indolocarbazole moiety and divalent linkage |
| US7829727B2 (en) * | 2005-11-16 | 2010-11-09 | Xerox Corporation | Device containing compound having indolocarbazole moiety and divalent linkage |
| CA2570780C (en) * | 2004-06-17 | 2013-12-03 | Infinity Pharmaceuticals, Inc. | Compounds and methods for inhibiting the interaction of bcl proteins with binding partners |
| JP2008519850A (ja) * | 2004-11-10 | 2008-06-12 | シンタ ファーマシューティカルズ コーポレーション | Il−12調節化合物 |
| US20060174937A1 (en) * | 2005-02-09 | 2006-08-10 | Zhang-Lin Zhou | High performance organic materials for solar cells |
| AR056786A1 (es) * | 2005-11-10 | 2007-10-24 | Smithkline Beecham Corp | Compuesto de 1h- imidazo ( 4,5-c) piridin-2-ilo, composicion farmaceutica que lo comprende, procedimiento para preparar dicha composicion, su uso para preparar unmedicamento, uso de una combinacion que omprende al compuesto y al menos un agente antineoplasico para preparar un medicamento y dicha com |
| WO2007058852A2 (en) * | 2005-11-10 | 2007-05-24 | Smithkline Beecham Corporation | Inhibitors of akt activity |
| US20080269131A1 (en) * | 2005-11-10 | 2008-10-30 | Smithkline Beecham Corporation | Inhibitors of Akt Activity |
| JP2010518014A (ja) * | 2007-01-31 | 2010-05-27 | バーテックス ファーマシューティカルズ インコーポレイテッド | キナーゼ阻害剤として有用な2−アミノピリジン誘導体 |
| US8343966B2 (en) * | 2008-01-11 | 2013-01-01 | Novartis Ag | Organic compounds |
-
2009
- 2009-06-26 US US12/997,868 patent/US20110086834A1/en not_active Abandoned
- 2009-06-26 WO PCT/US2009/003803 patent/WO2009158011A1/en not_active Ceased
- 2009-06-26 MX MX2010013920A patent/MX2010013920A/es not_active Application Discontinuation
- 2009-06-26 EP EP09770549A patent/EP2315751A1/en not_active Withdrawn
- 2009-06-26 AU AU2009263037A patent/AU2009263037B2/en not_active Ceased
- 2009-06-26 JP JP2011516311A patent/JP2011525915A/ja not_active Withdrawn
- 2009-06-26 CA CA2728767A patent/CA2728767A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011525915A (ja) | 2011-09-29 |
| EP2315751A1 (en) | 2011-05-04 |
| AU2009263037A1 (en) | 2009-12-30 |
| WO2009158011A1 (en) | 2009-12-30 |
| AU2009263037B2 (en) | 2011-10-06 |
| US20110086834A1 (en) | 2011-04-14 |
| CA2728767A1 (en) | 2009-12-30 |
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| Date | Code | Title | Description |
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| FA | Abandonment or withdrawal |