WO1999058096A3 - 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

Info

Publication number
WO1999058096A3
WO1999058096A3 PCT/US1999/010287 US9910287W WO9958096A3 WO 1999058096 A3 WO1999058096 A3 WO 1999058096A3 US 9910287 W US9910287 W US 9910287W WO 9958096 A3 WO9958096 A3 WO 9958096A3
Authority
WO
WIPO (PCT)
Prior art keywords
analogs
phthalimidinoglutaric
phthalimidinoglutaric acid
methyl
angiogenesis
Prior art date
Application number
PCT/US1999/010287
Other languages
French (fr)
Other versions
WO1999058096A2 (en
WO1999058096A9 (en
Inventor
Jamshed H Shah
Glenn M Swartz
Adonia E Papathanassiu
William E Fogler
John W Madsen
Shawn J Green
Original Assignee
Entremed Inc
Jamshed H Shah
Glenn M Swartz
Adonia E Papathanassiu
William E Fogler
John W Madsen
Shawn J Green
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 Entremed Inc, Jamshed H Shah, Glenn M Swartz, Adonia E Papathanassiu, William E Fogler, John W Madsen, Shawn J Green filed Critical Entremed Inc
Priority to EP99925585A priority Critical patent/EP1091726A2/en
Priority to AU41837/99A priority patent/AU749356B2/en
Priority to JP2000547948A priority patent/JP2002514578A/en
Priority to CA002331461A priority patent/CA2331461C/en
Publication of WO1999058096A2 publication Critical patent/WO1999058096A2/en
Publication of WO1999058096A3 publication Critical patent/WO1999058096A3/en
Publication of WO1999058096A9 publication Critical patent/WO1999058096A9/en

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)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Virology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Oncology (AREA)
  • Immunology (AREA)
  • Communicable Diseases (AREA)
  • Rheumatology (AREA)
  • Cardiology (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Pain & Pain Management (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Hematology (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (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 for 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.
PCT/US1999/010287 1998-05-11 1999-05-11 Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis WO1999058096A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP99925585A EP1091726A2 (en) 1998-05-11 1999-05-11 Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis
AU41837/99A AU749356B2 (en) 1998-05-11 1999-05-11 Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis
JP2000547948A JP2002514578A (en) 1998-05-11 1999-05-11 Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis
CA002331461A CA2331461C (en) 1998-05-11 1999-05-11 Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis

Applications Claiming Priority (6)

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

Publications (3)

Publication Number Publication Date
WO1999058096A2 WO1999058096A2 (en) 1999-11-18
WO1999058096A3 true WO1999058096A3 (en) 2000-05-18
WO1999058096A9 WO1999058096A9 (en) 2000-07-13

Family

ID=27374997

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/010287 WO1999058096A2 (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
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
KR20050062649A (en) * 2002-10-31 2005-06-23 셀진 코포레이션 Methods of using and compositions comprising selective cytokine inhibitory drugs for treatment and management of macular degeneration
US8952895B2 (en) 2011-06-03 2015-02-10 Apple Inc. Motion-based device operations
JP4943845B2 (en) 2003-09-17 2012-05-30 ザ ガバメント オブ ザ ユナイテッド ステイツ オブ アメリカ アズ リプレゼンティッド バイ ザ セクレタリー オブ ザ デパートメント オブ ヘルス アンド ヒューマン サービシーズ Thalidomide analog
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-isobenzazole compounds as well as preparation method and use thereof
US9617212B2 (en) 2013-12-17 2017-04-11 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

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994020085A1 (en) * 1993-03-01 1994-09-15 The Children's Medical Center Corporation Methods and compositions for inhibition of angiogenesis
EP0688771A1 (en) * 1994-06-24 1995-12-27 Grünenthal GmbH Use of lactam compounds as pharmaceutical agents

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994020085A1 (en) * 1993-03-01 1994-09-15 The Children's Medical Center Corporation Methods and compositions for inhibition of angiogenesis
EP0688771A1 (en) * 1994-06-24 1995-12-27 Grünenthal GmbH Use of lactam compounds as pharmaceutical agents

Also Published As

Publication number Publication date
CA2331461A1 (en) 1999-11-18
KR100699968B1 (en) 2007-03-28
JP2002514578A (en) 2002-05-21
EP1091726A2 (en) 2001-04-18
AU4183799A (en) 1999-11-29
WO1999058096A2 (en) 1999-11-18
WO1999058096A9 (en) 2000-07-13
AU749356B2 (en) 2002-06-27
CA2331461C (en) 2008-10-07
KR20010052332A (en) 2001-06-25

Similar Documents

Publication Publication Date Title
WO2002064083A3 (en) Synthesis of 3-amino-thalidomide and its enantiomers
CA2322204A1 (en) 5-aminoindeno(1,2-c)pyrazol-4-ones as anti-cancer and anti-proliferative agents
CA2449729A1 (en) Prodrugs of gaba analogs, compositions and uses thereof
WO2002076976A3 (en) Rho-kinase inhibitors
WO2002076977A3 (en) Rho-kinase inhibitors
WO2000010507A3 (en) Use of melanin for inhibition of angiogenesis and macular degeneration
WO2003020212A3 (en) Treatment for central nervous system disorders
WO2005051304A3 (en) Akt protein kinase inhibitors
CA2337991A1 (en) Benzocycloheptenes, process for their production, pharmaceutical preparations that contain the latter as well as their use for the production of pharmaceutical agents
WO1999058096A3 (en) Analogs of 2-phthalimidinoglutaric acid and their use as inhibitors of angiogenesis
WO2003045330A3 (en) Materials and methods for making improved micelle compositions
WO2000066528A3 (en) Quinones for treatment of diseases
WO2002040484A3 (en) Novel imidazole derivatives, production method thereof and use thereof
ES8704482A1 (en) Method of treating liver diseases using pure silibinin
GB0322510D0 (en) Novel compounds
WO2003007883A3 (en) Acylsemicarbazides as cyclin dependent kinase inhibitors useful as anti-cancer and anti-proliferative agents
WO2006019685A3 (en) Compounds and their preparation for the treatment of alzheimer's disease by inhibiting beta-amyloid peptide production
WO2001000617A3 (en) Novel piperazinylalkylthiopyrimidine derivatives, pharmaceutical compositions containing the same, and a process for the preparation of the same
WO2004073375A3 (en) Podophyllotoxin derivatives as antitumor agents
WO2001080845A3 (en) (2-aminoethyl) oxime derivatives for the treatment of depression
ATE339423T1 (en) METHOD FOR PRODUCING 4'-O-SUBSTITUTED 4'-DEMETHYL-1 DEOXYPODOPHYLLOTOXINE DERIVATIVES AND GEOMETRIC ISOMERS THEREOF, AND ANTICANCER PREPARATION CONTAINING SAME
WO2003080624A3 (en) Dithiolopyrrolone derivatives useful in the treatment of proliferative diseases
WO2002046163A3 (en) Quinoline derivatives and their use as anti-epileptics
WO2005020911A3 (en) Benzo[1, 3]dioxole compounds, pharmaceutical compositions thereof, and processes of making and using the same
WO2004062596A3 (en) Antineoplastic ether lipid compounds having a four carbon backbone

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW SD SL SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): GH GM KE LS MW SD SL SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

AK Designated states

Kind code of ref document: C2

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: C2

Designated state(s): GH GM KE LS MW SD SL SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

COP Corrected version of pamphlet

Free format text: PAGES 1/14-14/14, DRAWINGS, REPLACED BY NEW PAGES 1/14-14/14; DUE TO LATE TRANSMITTAL BY THE RECEIVING OFFICE

ENP Entry into the national phase

Ref document number: 2331461

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 1020007012550

Country of ref document: KR

ENP Entry into the national phase

Ref country code: JP

Ref document number: 2000 547948

Kind code of ref document: A

Format of ref document f/p: F

WWE Wipo information: entry into national phase

Ref document number: 41837/99

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 1999925585

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWP Wipo information: published in national office

Ref document number: 1999925585

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1020007012550

Country of ref document: KR

WWG Wipo information: grant in national office

Ref document number: 41837/99

Country of ref document: AU

WWR Wipo information: refused in national office

Ref document number: 1020007012550

Country of ref document: KR