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WO2004046122A3 - Benzoxazole, benzthiazole and benzimidazole acid derivatives and their use as heparanase inhibitors - Google Patents

Benzoxazole, benzthiazole and benzimidazole acid derivatives and their use as heparanase inhibitors Download PDF

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Publication number
WO2004046122A3
WO2004046122A3 PCT/GB2003/004991 GB0304991W WO2004046122A3 WO 2004046122 A3 WO2004046122 A3 WO 2004046122A3 GB 0304991 W GB0304991 W GB 0304991W WO 2004046122 A3 WO2004046122 A3 WO 2004046122A3
Authority
WO
WIPO (PCT)
Prior art keywords
benzthiazole
benzoxazole
acid derivatives
heparanase inhibitors
benzimidazole acid
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.)
Ceased
Application number
PCT/GB2003/004991
Other languages
French (fr)
Other versions
WO2004046122A2 (en
Inventor
Stephen Martin Courtney
Philip Andrew Hay
David Ian Carter Scopes
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.)
Oxford Glycosciences UK Ltd
Original Assignee
Oxford Glycosciences UK Ltd
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
Priority claimed from GB0226820A external-priority patent/GB0226820D0/en
Priority claimed from GB0319542A external-priority patent/GB0319542D0/en
Application filed by Oxford Glycosciences UK Ltd filed Critical Oxford Glycosciences UK Ltd
Priority to AU2003283597A priority Critical patent/AU2003283597A1/en
Publication of WO2004046122A2 publication Critical patent/WO2004046122A2/en
Publication of WO2004046122A3 publication Critical patent/WO2004046122A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/12—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 linked by a chain containing hetero atoms as chain links
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compounds of formula (I): wherein R1, R2 and R3 are independently, hydrogen, halogen, CF3, OR6, NR7R8, NR8COR10, NR8SO2R10 or C1-6 alkyl optionally substituted by hydroxy, C1-6 alkoxy or NR7R8; R4 is NR8CONR8R9, NR8COR9, NR8SO2R9, or W-CONR8R9, where W is a bond, C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene; and R5 is Formula (A) methods for their synthesis, pharmaceutical compositions comprising them and their use in medicine, in particular for the treatment of cancer.
PCT/GB2003/004991 2002-11-16 2003-11-17 Benzoxazole, benzthiazole and benzimidazole acid derivatives and their use as heparanase inhibitors Ceased WO2004046122A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003283597A AU2003283597A1 (en) 2002-11-16 2003-11-17 Benzoxazole, benzthiazole and benzimidazole acid derivatives and their use as heparanase inhibitors

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB0226820A GB0226820D0 (en) 2002-11-16 2002-11-16 Novel compounds
GB0226820.9 2002-11-16
GB0319542.7 2003-08-20
GB0319542A GB0319542D0 (en) 2003-08-20 2003-08-20 Novel compounds

Publications (2)

Publication Number Publication Date
WO2004046122A2 WO2004046122A2 (en) 2004-06-03
WO2004046122A3 true WO2004046122A3 (en) 2004-07-15

Family

ID=32328067

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2003/004991 Ceased WO2004046122A2 (en) 2002-11-16 2003-11-17 Benzoxazole, benzthiazole and benzimidazole acid derivatives and their use as heparanase inhibitors

Country Status (2)

Country Link
AU (1) AU2003283597A1 (en)
WO (1) WO2004046122A2 (en)

Families Citing this family (22)

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Publication number Priority date Publication date Assignee Title
EP2363129A1 (en) * 2004-10-13 2011-09-07 PTC Therapeutics, Inc. Pyrazole or triazole compounds and their use for the manufacture of a medicament for treating somatic mutation-related diseases
EP1688413A1 (en) * 2005-02-03 2006-08-09 Hikma Pharmaceuticals Co. Ltd. Benzoxazole derivatives for the prophylaxis and treatment of inflammatory bowel diseases
WO2006094236A1 (en) * 2005-03-03 2006-09-08 Sirtris Pharmaceuticals, Inc. N-phenyl benzamide derivatives as sirtuin modulators
WO2007042816A1 (en) * 2005-10-12 2007-04-19 Biolipox Ab Benzoxazoles useful in the treatment of inflammation
JP5301999B2 (en) 2005-10-31 2013-09-25 メルク・シャープ・アンド・ドーム・コーポレーション CETP inhibitor
CN101541783B (en) * 2006-06-30 2014-10-01 苏尼西斯制药有限公司 Pyridinone-based PDK1 inhibitors
EP2102177A1 (en) * 2006-12-14 2009-09-23 Boehringer Ingelheim International GmbH Benzoxazoles useful in the treatment of inflammation
AU2008205252B2 (en) * 2007-01-09 2013-02-21 Amgen Inc. Bis-aryl amide derivatives useful for the treatment of cancer
WO2010126914A1 (en) * 2009-04-27 2010-11-04 Elan Pharmaceuticals, Inc. Pyridinone antagonists of alpha-4 integrins
CN104220058A (en) 2012-01-27 2014-12-17 国立大学法人富山大学 Serine racemase inhibitor
PT3137456T (en) 2014-04-29 2021-08-06 Fmc Corp PYRIDAZINONE HERBICIDES
CN104529729B (en) * 2014-12-31 2016-03-30 浙江永太科技股份有限公司 The preparation method of the fluoro-3-chlorobenzaldehyde of a kind of 2-
JP6905521B2 (en) 2015-10-28 2021-07-21 エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ New pyridadinone herbicide
JP2020503377A (en) 2016-12-13 2020-01-30 ベータ セラピューティクス プロプライアタリー リミティド Heparanase inhibitors and uses thereof
US11787783B2 (en) 2016-12-13 2023-10-17 Beta Therapeutics Pty Ltd Heparanase inhibitors and use thereof
EP3381908A1 (en) 2017-03-27 2018-10-03 Leadiant Biosciences SA 2-(4-(4-(bromo-methoxybenzamido)benzylamino)phenyl)benzazole derivatives and their use as anti-heparanase
EP3381907A1 (en) 2017-03-27 2018-10-03 Leadiant Biosciences SA Symmetrical 2-aminophenyl-benzazolyl-5-acetate compounds and their use as anti-heparanase
TWI785022B (en) 2017-03-28 2022-12-01 美商富曼西公司 Novel pyridazinone herbicides
US11548867B2 (en) 2017-07-19 2023-01-10 Idea Ya Biosciences, Inc. Amido compounds as AhR modulators
EP4046636A4 (en) * 2019-11-18 2023-04-19 YJ Cerapeutics Inc. Composition for treating spinal cord injury, comprising stem cells treated with novel compound
WO2021116820A1 (en) * 2019-12-10 2021-06-17 Aurobindo Pharma Limited An improved process for the preparation of benoxaprofen
CN117924386B (en) * 2023-12-22 2024-07-12 合肥综合性国家科学中心大健康研究院 HPA1 degradation agent and preparation method and application thereof

Citations (6)

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US3267081A (en) * 1962-09-19 1966-08-16 Koppers Co Inc Benzothiazole dicarboxylic acids and polymers derived therefrom
JPS4943974A (en) * 1972-09-06 1974-04-25
US3912748A (en) * 1972-05-18 1975-10-14 Lilly Industries Ltd Benzoxazole derivatives
US4659360A (en) * 1984-11-30 1987-04-21 Fmc Corporation Plant growth and development modification using benzoxazole derivatives
US4705861A (en) * 1984-11-29 1987-11-10 Bayer Aktiengesellschaft Aminophenylbenzothiazoles
WO2002060374A2 (en) * 2001-01-29 2002-08-08 Insight Strategy And Marketing Ltd Benz-1,3-azole derivatives and their uses as heparanase inhibitors

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3267081A (en) * 1962-09-19 1966-08-16 Koppers Co Inc Benzothiazole dicarboxylic acids and polymers derived therefrom
US3912748A (en) * 1972-05-18 1975-10-14 Lilly Industries Ltd Benzoxazole derivatives
JPS4943974A (en) * 1972-09-06 1974-04-25
US4705861A (en) * 1984-11-29 1987-11-10 Bayer Aktiengesellschaft Aminophenylbenzothiazoles
US4659360A (en) * 1984-11-30 1987-04-21 Fmc Corporation Plant growth and development modification using benzoxazole derivatives
WO2002060374A2 (en) * 2001-01-29 2002-08-08 Insight Strategy And Marketing Ltd Benz-1,3-azole derivatives and their uses as heparanase inhibitors

Non-Patent Citations (8)

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Title
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002277729, retrieved from STN Database accession no. 1974:505488 *
HASKELL T H ET AL: "Neuraminidase inhibition and viral chemotherapy", JOURNAL OF MEDICINAL CHEMISTRY, vol. 13, no. 4, July 1970 (1970-07-01), pages 697 - 704, XP002277728 *
KREIMEYER A ET AL: "Suramin analogues with a 2-phenylbenzimidazole moiety as partial structure", DIE PHARMAZIE, vol. 52, no. 4, April 1997 (1997-04-01), pages 268 - 271, XP002277724 *
MARCOS-FERNANDEZ A ET AL: "Novel aromatic polyamides with 1,3-benzoazole groups in the main chain. 1. Polymers derived from 2-(4-carboxyphenyl) benzoxazole-5- and 6-carboxylic acids. Synthesis and characterization", POLYMER, vol. 42, no. 19, September 2001 (2001-09-01), pages 7933 - 7941, XP004245973 *
SCHUBERT M: "Zur Kenntnis der Dehydrothiotoluidin- und Primulin-sulfosäuren", LIEBIGS ANNALEN DER CHEMIE, vol. 558, 1947, pages 10 - 34, XP002277725 *
STEPHENS F F ET AL: "The preparation of benziminazoles and benzoxazoles from Schiff's bases. Part II", JOURNAL OF THE CHMICAL SOCIETY, 1950, pages 1722 - 1726, XP002277727 *
THOMAS P R ET AL: "Some new benzimidazole derivatives", JOURNAL OF THE CHEMICAL SOCIETY, 1957, pages 2197 - 2201, XP002277726 *
YOKUM T S ET AL: "Solid-phase syntheses of heterocycles containing the 2-aminothiophenol moiety", JOURNAL OF COMBINATORIAL CHEMISTRY, vol. 2, no. 3, 19 May 2000 (2000-05-19), pages 282 - 292, XP002184776 *

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Publication number Publication date
WO2004046122A2 (en) 2004-06-03
AU2003283597A8 (en) 2004-06-15
AU2003283597A1 (en) 2004-06-15

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