CA2699787A1 - (3-hydroxy-4-amino-butan-2-yl)-3-(2-thiazol-2-yl-pyrrolidine-1-carbonyl) benzamide derivatives and related compounds as beta-secretase inhibitors for treating - Google Patents

(3-hydroxy-4-amino-butan-2-yl)-3-(2-thiazol-2-yl-pyrrolidine-1-carbonyl) benzamide derivatives and related compounds as beta-secretase inhibitors for treating Download PDF

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Publication number
CA2699787A1
CA2699787A1 CA2699787A CA2699787A CA2699787A1 CA 2699787 A1 CA2699787 A1 CA 2699787A1 CA 2699787 A CA2699787 A CA 2699787A CA 2699787 A CA2699787 A CA 2699787A CA 2699787 A1 CA2699787 A1 CA 2699787A1
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CA
Canada
Prior art keywords
substituted
unsubstituted
compound
solvate
pharmaceutically acceptable
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.)
Abandoned
Application number
CA2699787A
Other languages
English (en)
French (fr)
Inventor
Arun K. Ghosh
Chunfeng Liu
Thippeswamy Devasamudram
Hui Lei
Lisa M. Swanson
Sudha V. Ankala
John C. Lilly
Geoffrey M. Bilcer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Purdue Research Foundation
CoMentis Inc
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2699787A1 publication Critical patent/CA2699787A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • 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
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pyrrole Compounds (AREA)
CA2699787A 2007-09-24 2008-09-24 (3-hydroxy-4-amino-butan-2-yl)-3-(2-thiazol-2-yl-pyrrolidine-1-carbonyl) benzamide derivatives and related compounds as beta-secretase inhibitors for treating Abandoned CA2699787A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US97479307P 2007-09-24 2007-09-24
US60/974,793 2007-09-24
PCT/US2008/077537 WO2009042694A1 (en) 2007-09-24 2008-09-24 (3-hydroxy-4-amino-butan-2-yl) -3- (2-thiazol-2-yl-pyrrolidine-1-carbonyl) benzamide derivatives and related compounds as beta-secretase inhibitors for treating

Publications (1)

Publication Number Publication Date
CA2699787A1 true CA2699787A1 (en) 2009-04-02

Family

ID=40343545

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2699787A Abandoned CA2699787A1 (en) 2007-09-24 2008-09-24 (3-hydroxy-4-amino-butan-2-yl)-3-(2-thiazol-2-yl-pyrrolidine-1-carbonyl) benzamide derivatives and related compounds as beta-secretase inhibitors for treating

Country Status (8)

Country Link
US (1) US8299267B2 (OSRAM)
EP (1) EP2205596A1 (OSRAM)
JP (1) JP5055432B2 (OSRAM)
KR (1) KR20100059919A (OSRAM)
CN (1) CN101868457B (OSRAM)
CA (1) CA2699787A1 (OSRAM)
MX (1) MX2010002938A (OSRAM)
WO (1) WO2009042694A1 (OSRAM)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2205596A1 (en) 2007-09-24 2010-07-14 Comentis, Inc. (3-hydroxy-4-amino-butan-2-yl) -3- (2-thiazol-2-yl-pyrrolidine-1-carbonyl) benzamide derivatives and related compounds as beta-secretase inhibitors for treating
WO2011028288A1 (en) * 2009-09-04 2011-03-10 Tactical Therapeutics, Inc Novel compositions and processes for preparing 5-amino or substituted amino 1,2,3-triazoles and triazole orotate formulations
CN102695546B (zh) 2009-09-11 2014-09-10 前体生物药物股份公司 作为谷氨酰胺酰环化酶抑制剂的杂环衍生物
EP2486006A4 (en) * 2009-10-05 2013-05-01 Comentis Inc SULFONAMIDO PYRROLIDINE COMPOUNDS THAT INHIBIT BETA SECRETASE ACTIVITY AND METHODS OF USE THEREOF
WO2012027495A1 (en) 2010-08-27 2012-03-01 University Of The Pacific Piperazinylpyrimidine analogues as protein kinase inhibitors
US20120053200A1 (en) * 2010-09-01 2012-03-01 Harald Mauser Bace 2 inhibitors
KR20150021036A (ko) 2012-06-14 2015-02-27 다이이찌 산쿄 가부시키가이샤 피페리디닐피라졸로피리딘 유도체
CN105669365B (zh) * 2016-03-04 2022-06-21 中国科学院上海有机化学研究所 含二氟烷基取代的芳基或杂芳基化合物、制备方法和应用
PL3461819T3 (pl) 2017-09-29 2020-11-30 Probiodrug Ag Inhibitory cyklazy glutaminylowej
CN110117237B (zh) * 2018-02-05 2024-02-02 中国科学院上海有机化学研究所 一种芳香腈或烯基腈类化合物的制备方法
CN110642789B (zh) * 2019-11-25 2020-05-26 天津凯莱英制药有限公司 2-氯嘧啶-4-甲酸类化合物的连续性合成方法
CN112321515A (zh) * 2020-10-21 2021-02-05 上海馨远医药科技有限公司 一种手性1-叔丁基-3-甲基-6-甲基哌嗪-1,3-二甲酸酯的制备方法
WO2023149945A1 (en) * 2022-02-03 2023-08-10 Purdue Research Foundation Peptidomimetic inhibitors of protein n-terminal methyltransferase 1, composition, and method of use
US12191004B2 (en) 2022-06-27 2025-01-07 Microsoft Technology Licensing, Llc Machine learning system with two encoder towers for semantic matching

Family Cites Families (63)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4911920A (en) 1986-07-30 1990-03-27 Alcon Laboratories, Inc. Sustained release, comfort formulation for glaucoma therapy
FR2588189B1 (fr) 1985-10-03 1988-12-02 Merck Sharp & Dohme Composition pharmaceutique de type a transition de phase liquide-gel
US4902505A (en) 1986-07-30 1990-02-20 Alkermes Chimeric peptides for neuropeptide delivery through the blood-brain barrier
US4801575A (en) 1986-07-30 1989-01-31 The Regents Of The University Of California Chimeric peptides for neuropeptide delivery through the blood-brain barrier
US6407061B1 (en) 1989-12-05 2002-06-18 Chiron Corporation Method for administering insulin-like growth factor to the brain
US5624898A (en) 1989-12-05 1997-04-29 Ramsey Foundation Method for administering neurologic agents to the brain
EP0495421B1 (en) 1991-01-15 1996-08-21 Alcon Laboratories, Inc. Use of carrageenans in topical ophthalmic compositions
US5212162A (en) 1991-03-27 1993-05-18 Alcon Laboratories, Inc. Use of combinations gelling polysaccharides and finely divided drug carrier substrates in topical ophthalmic compositions
US6287792B1 (en) 1991-06-17 2001-09-11 The Regents Of The University Of California Drug delivery of antisense oligonucleotides and peptides to tissues in vivo and to cells using avidin-biotin technology
TW282460B (OSRAM) 1993-12-28 1996-08-01 Yamanouchi Pharma Co Ltd
US6309853B1 (en) 1994-08-17 2001-10-30 The Rockfeller University Modulators of body weight, corresponding nucleic acids and proteins, and diagnostic and therapeutic uses thereof
US5728718A (en) 1994-12-20 1998-03-17 The United States Of America As Represented By The Department Of Health And Human Services 2,5-diamino-3,4-disubstituted-1,6-diphenylhexane isosteres comprising benzamide, sulfonamide and anthranilamide subunits and methods of using same
AU5773500A (en) 1999-06-28 2001-01-31 Board Of Trustees Of The University Of Illinois, The Inhibitors of memapsin 2 and use thereof
DE60038183T2 (de) 1999-12-16 2009-02-19 Emisphere Technologies, Inc. Verbindungen und zusammensetzungen zur abgabe aktiver wirkstoffe
EP1272222A2 (en) 2000-04-12 2003-01-08 Implyx Ltd. Compositions for drug delivery
US6372250B1 (en) 2000-04-25 2002-04-16 The Regents Of The University Of California Non-invasive gene targeting to the brain
US6846813B2 (en) 2000-06-30 2005-01-25 Pharmacia & Upjohn Company Compounds to treat alzheimer's disease
PE20020276A1 (es) 2000-06-30 2002-04-06 Elan Pharm Inc COMPUESTOS DE AMINA SUSTITUIDA COMO INHIBIDORES DE ß-SECRETASA PARA EL TRATAMIENTO DE ALZHEIMER
MXPA02012560A (es) 2000-06-30 2003-05-14 Elan Pharm Inc Compuestos para tratar la enfermedad de alzheimer.
EP1404718A2 (en) 2000-12-28 2004-04-07 Oklahoma Medical Research Foundation Inhibitors of memapsin 2 and use thereof
US20040121947A1 (en) 2000-12-28 2004-06-24 Oklahoma Medical Research Foundation Compounds which inhibit beta-secretase activity and methods of use thereof
WO2002064558A2 (en) 2001-02-14 2002-08-22 Sankyo Company, Limited Oxazole derivatives, their preparation and their use as cytokine inhibitors
US20060234944A1 (en) 2001-10-23 2006-10-19 Oklahoma Medical Reseach Foundation Beta-secretase inhibitors and methods of use
CA2464736A1 (en) 2001-10-23 2003-05-15 Oklahoma Medical Research Foundation Beta-secretase inhibitors and methods of use
EP1453789A2 (en) 2001-11-08 2004-09-08 Elan Pharmaceuticals, Inc. N,n'-substituted-1,3-diamino-2-hydroxypropane derivatives
BR0214736A (pt) 2001-12-06 2004-11-23 Elan Pharm Inc Composto e seus sais farmaceuticamente aceitáveis, composição farmacêutica e método de tratar seres humanos ou animais que sofrem de doenças ou condições
MXPA04008317A (es) 2002-02-27 2005-06-08 Upjohn Co Hidroxietilaminas sustituidas.
AU2003220115A1 (en) 2002-05-20 2003-12-12 Board Of Regents, The University Of Texas System Methods and compositions for delivering enzymes and nucleic acid molecules to brain, bone, and other tissues
JP2005538162A (ja) 2002-09-06 2005-12-15 イーラン ファーマスーティカルズ、インコーポレイテッド １，３−ジアミノ−２−ヒドロキシプロパンプロドラッグ誘導体
CA2505098A1 (en) 2002-11-12 2004-05-27 Merck & Co., Inc. Phenylcarboxamide beta-secretase inhibitors for the treatment of alzheimer's disease
US20040102369A1 (en) 2002-11-27 2004-05-27 The Regents Of The University Of California Transport of basic fibroblast growth factor across the blood brain barrier
US7388079B2 (en) 2002-11-27 2008-06-17 The Regents Of The University Of California Delivery of pharmaceutical agents via the human insulin receptor
GB0228410D0 (en) 2002-12-05 2003-01-08 Glaxo Group Ltd Novel Compounds
GB0305918D0 (en) 2003-03-14 2003-04-23 Glaxo Group Ltd Novel compounds
DE602004019793D1 (de) 2003-08-08 2009-04-16 Schering Corp Cyclische amine mit benzamidsubstituent als bace-1-inhibitoren
KR100793095B1 (ko) 2003-10-01 2008-01-10 주식회사 프로메디텍 Ｂａｃｅ 저해효능을 가진 신규한 술폰 아미드 유도체
AU2004311749A1 (en) 2003-12-19 2005-07-21 Merck & Co., Inc. Phenylamide and pyridylamide beta-secretase inhibitors for the treatment of Alzheimer's disease
US7585885B2 (en) 2004-04-22 2009-09-08 Eli Lilly And Company Pyrrolidine derivatives useful as BACE inhibitors
EP1740575A2 (en) 2004-04-22 2007-01-10 Eli Lilly And Company Pyrrolidine derivatives useful as bace inhibitors
CN1968924B (zh) 2004-06-15 2011-08-03 默沙东公司 作为β-分泌酶抑制剂用于治疗阿尔茨海默氏病的吡咯烷-3-基化合物
US8436006B2 (en) 2004-08-06 2013-05-07 Jansssen Pharmaceutica N.V. 2-amino-quinazoline derivatives useful as inhibitors of β-secretase (BACE)
CA2580238A1 (en) * 2004-09-17 2006-03-30 Comentis, Inc. Bicyclic compounds which inhibit beta-secretase activity and methods of use thereof
US7659289B2 (en) 2004-09-17 2010-02-09 Comentis, Inc. Hydroxyethylene-based β-secretase inhibitors and use thereof
CN100475786C (zh) * 2005-02-18 2009-04-08 中国科学院上海药物研究所 一类4-羟基戊酰胺类化合物及其制备方法和用途
US7745470B2 (en) 2005-03-10 2010-06-29 Bristol-Myers Squibb Company Isophthalates as beta-secretase inhibitors
JP2008535863A (ja) 2005-04-08 2008-09-04 コメンティス，インコーポレーテッド β−セクレターゼ活性を阻害する化合物およびその使用方法
MY144968A (en) 2005-04-11 2011-11-30 Xenon Pharmaceuticals Inc Spiro-oxindole compounds and their uses as therapeutic agents
AR054044A1 (es) 2005-05-23 2007-05-30 Astrazeneca Ab Derivados de cromano y tetrahidronaftaleno como moduladores del receptor 5 - ht6; intermediarios en su preparacion; composiciones farmaceuticas que los contienen y su empelo en la fabricacion de medicamentos para el tratamiento de enfermedades del snc y de la obesidad.
AR054363A1 (es) 2005-05-23 2007-06-20 Astrazeneca Ab Compuestos que exhiben actividad moduladora en el receptor 5-hidroxi-triptamina 6
GB0513886D0 (en) 2005-07-06 2005-08-10 Glaxo Group Ltd Novel compounds
US7476764B2 (en) 2005-08-04 2009-01-13 Bristol-Myers Squibb Company Phenylcarboxyamides as beta-secretase inhibitors
US7790745B2 (en) 2005-10-21 2010-09-07 Bristol-Myers Squibb Company Tetrahydroisoquinoline LXR Modulators
TW200804290A (en) 2005-11-15 2008-01-16 Astrazeneca Ab Compounds and uses thereof
US8143405B2 (en) 2006-09-21 2012-03-27 Merck, Sharp & Dohme Corp Piperidine and pyrrolidine beta-secretase inhibitors for the treatment of alzheimer's disease
WO2009015369A2 (en) 2007-07-26 2009-01-29 Comentis, Inc. Compounds which inhibit beta-secretase activity and methods of use thereof
EP2205596A1 (en) 2007-09-24 2010-07-14 Comentis, Inc. (3-hydroxy-4-amino-butan-2-yl) -3- (2-thiazol-2-yl-pyrrolidine-1-carbonyl) benzamide derivatives and related compounds as beta-secretase inhibitors for treating
US8791135B2 (en) 2008-07-01 2014-07-29 Purdue Research Foundation Nonpeptide HIV-1 protease inhibitors
EP2349244A4 (en) 2008-10-10 2012-09-19 Comentis Inc PYRROLIDINE COMPOUNDS THAT PREVENT BETA-SECRETASE ACTIVITY AND METHODS OF USE THEREOF
JP2012505241A (ja) 2008-10-10 2012-03-01 パーデュー・リサーチ・ファウンデーション アルツハイマー病の治療用組成物
CA2744425A1 (en) 2008-11-20 2010-05-27 Purdue Research Foundation Quinazoline inhibitors of bace 1 and methods of using
US8859590B2 (en) 2008-12-05 2014-10-14 Purdue Research Foundation Inhibitors of BACE1 and methods for treating Alzheimer's disease
WO2010110817A1 (en) 2009-03-25 2010-09-30 Comentis, Inc. Pyrrolidine compounds which inhibit beta-secretase activity and methods of use thereof
EP2486006A4 (en) 2009-10-05 2013-05-01 Comentis Inc SULFONAMIDO PYRROLIDINE COMPOUNDS THAT INHIBIT BETA SECRETASE ACTIVITY AND METHODS OF USE THEREOF

Also Published As

Publication number Publication date
JP5055432B2 (ja) 2012-10-24
CN101868457B (zh) 2013-02-13
US20100286170A1 (en) 2010-11-11
WO2009042694A1 (en) 2009-04-02
US8299267B2 (en) 2012-10-30
KR20100059919A (ko) 2010-06-04
MX2010002938A (es) 2010-04-01
JP2010540462A (ja) 2010-12-24
EP2205596A1 (en) 2010-07-14
CN101868457A (zh) 2010-10-20

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Legal Events

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FZDE Discontinued

Effective date: 20140924