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CA2331461A1 - Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis - Google Patents

Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis Download PDF

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Publication number
CA2331461A1
CA2331461A1 CA002331461A CA2331461A CA2331461A1 CA 2331461 A1 CA2331461 A1 CA 2331461A1 CA 002331461 A CA002331461 A CA 002331461A CA 2331461 A CA2331461 A CA 2331461A CA 2331461 A1 CA2331461 A1 CA 2331461A1
Authority
CA
Canada
Prior art keywords
analogs
phthalimidinoglutaric
phthalimidinoglutaric acid
methyl
angiogenesis
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.)
Granted
Application number
CA002331461A
Other languages
French (fr)
Other versions
CA2331461C (en
Inventor
Jamshed H. Shah
Glenn M. Swartz
Adonia E. Papathanassiu
William E. Fogler
John W. Madsen
Shawn J. Green
Robert J. D'amato
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.)
Boston Childrens Hospital
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 CA2331461A1 publication Critical patent/CA2331461A1/en
Application granted granted Critical
Publication of CA2331461C publication Critical patent/CA2331461C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
    • 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
    • A61P17/06—Antipsoriatics
    • 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
    • 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
    • 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
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Immunology (AREA)
  • Communicable Diseases (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Cardiology (AREA)
  • Hematology (AREA)
  • Neurosurgery (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Indole Compounds (AREA)

Abstract

The invention provides new and useful analogs of 2-phthalimidinoglutaric acid.
These analogs include DL-2-methyl-2-phthalimidinoglutaric acid and hydroxylated analogs of 2-phthalimidinoglutaric wherein each of R3 and R4 are independently H or OH. The invention also provides processes for making these analogs. The invention also provides the two individual enantiomers of DL-2-methyl-2--phthalimidinoglutaric acid. (R)-(+)-2-methyl-2-phthalimidinoglutaric acid and (S)-(-)-2-methyl-2-phthalimidinoglutaric acid, and processes or separating these individual enantiomers from the racemate. Further, the invention provides methods for inhibiting angiogenesis and treating angiogenesis-associated diseases. including cancer and macular degeneration, by administering one or more of these compounds.
CA002331461A 1998-05-11 1999-05-11 Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis Expired - Fee Related CA2331461C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US8503798P 1998-05-11 1998-05-11
US60/085,037 1998-05-11
US9738498P 1998-08-21 1998-08-21
US60/097,384 1998-08-21
US10803798P 1998-11-12 1998-11-12
US60/108,037 1998-11-12
PCT/US1999/010287 WO1999058096A2 (en) 1998-05-11 1999-05-11 Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis

Publications (2)

Publication Number Publication Date
CA2331461A1 true CA2331461A1 (en) 1999-11-18
CA2331461C CA2331461C (en) 2008-10-07

Family

ID=27374997

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002331461A Expired - Fee Related CA2331461C (en) 1998-05-11 1999-05-11 Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis

Country Status (6)

Country Link
EP (1) EP1091726A2 (en)
JP (1) JP2002514578A (en)
KR (1) KR100699968B1 (en)
AU (1) AU749356B2 (en)
CA (1) CA2331461C (en)
WO (1) WO1999058096A2 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7182953B2 (en) 1999-12-15 2007-02-27 Celgene Corporation Methods and compositions for the prevention and treatment of atherosclerosis restenosis and related disorders
WO2002068414A2 (en) 2001-02-27 2002-09-06 The Governement Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services Analogs of thalidomide as potential angiogenesis inhibitors
EP1567148A4 (en) * 2002-10-31 2010-09-15 Celgene Corp Methods of using and compositions comprising selective cytokine inhibitory drugs for treatment and management of macular degeneration
US7776907B2 (en) 2002-10-31 2010-08-17 Celgene Corporation Methods for the treatment and management of macular degeneration using cyclopropyl-N-{2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-3-oxoisoindoline-4-yl}carboxamide
SG133603A1 (en) 2003-09-17 2007-07-30 Us Gov Health & Human Serv Thalidomide analogs as tnf-alpha modulators
US8952895B2 (en) 2011-06-03 2015-02-10 Apple Inc. Motion-based device operations
US8927725B2 (en) 2011-12-02 2015-01-06 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Thio compounds
CN104045594B (en) * 2012-02-21 2016-08-17 四川大学 One class 1,3-dihydro-1-oxygen-2H-isoindoles compound and application thereof
CN102603610B (en) * 2012-02-21 2014-07-09 四川大学 1,3-dihydro-1-oxo-2H-isoindole compound, its preparation method and use
WO2015095052A1 (en) * 2013-12-17 2015-06-25 Controlled Chemicals, Inc. Isoindolin-1-ones as macrophage migration inhibitory factor (mif) inhibitors
CN109467550B (en) * 2017-12-31 2022-02-18 苏州亚科科技股份有限公司 Synthesis method of phthalic diamide-L-glutamic anhydride

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5629327A (en) * 1993-03-01 1997-05-13 Childrens Hospital Medical Center Corp. Methods and compositions for inhibition of angiogenesis
DE4422237A1 (en) * 1994-06-24 1996-01-04 Gruenenthal Gmbh Use of lactam compounds as active pharmaceutical ingredients

Also Published As

Publication number Publication date
WO1999058096A9 (en) 2000-07-13
WO1999058096A2 (en) 1999-11-18
JP2002514578A (en) 2002-05-21
CA2331461C (en) 2008-10-07
AU749356B2 (en) 2002-06-27
AU4183799A (en) 1999-11-29
WO1999058096A3 (en) 2000-05-18
KR20010052332A (en) 2001-06-25
KR100699968B1 (en) 2007-03-28
EP1091726A2 (en) 2001-04-18

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Effective date: 20190513