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WO2009037705A3 - Esters of n-phenylanthranilic acid for use in the treatment of cancer and inflammation - Google Patents

Esters of n-phenylanthranilic acid for use in the treatment of cancer and inflammation Download PDF

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Publication number
WO2009037705A3
WO2009037705A3 PCT/IL2008/001255 IL2008001255W WO2009037705A3 WO 2009037705 A3 WO2009037705 A3 WO 2009037705A3 IL 2008001255 W IL2008001255 W IL 2008001255W WO 2009037705 A3 WO2009037705 A3 WO 2009037705A3
Authority
WO
WIPO (PCT)
Prior art keywords
inflammation
cancer
esters
treatment
phenylanthranilic 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/IL2008/001255
Other languages
French (fr)
Other versions
WO2009037705A2 (en
Inventor
Amiram Raz
Bernard Attali
Asher Peretz
Maya Talmon
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.)
Ramot at Tel Aviv University Ltd
Original Assignee
Ramot at Tel Aviv University 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
Application filed by Ramot at Tel Aviv University Ltd filed Critical Ramot at Tel Aviv University Ltd
Publication of WO2009037705A2 publication Critical patent/WO2009037705A2/en
Publication of WO2009037705A3 publication Critical patent/WO2009037705A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Landscapes

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

Abstract

Methods, unit dosage forms and compositions for treating cancer and inflammation, and which utilize ester derivatives of N-phenylanthranilic acid that exhibit tissue-selective anti-COX activity are disclosed.
PCT/IL2008/001255 2007-09-20 2008-09-18 Esters of n-phenylanthranilic acid for use in the treatment of cancer and inflammation Ceased WO2009037705A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US96021607P 2007-09-20 2007-09-20
US60/960,216 2007-09-20

Publications (2)

Publication Number Publication Date
WO2009037705A2 WO2009037705A2 (en) 2009-03-26
WO2009037705A3 true WO2009037705A3 (en) 2009-07-09

Family

ID=40468560

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IL2008/001255 Ceased WO2009037705A2 (en) 2007-09-20 2008-09-18 Esters of n-phenylanthranilic acid for use in the treatment of cancer and inflammation

Country Status (1)

Country Link
WO (1) WO2009037705A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7632866B2 (en) 2002-10-21 2009-12-15 Ramot At Tel Aviv University Derivatives of N-phenylanthranilic acid and 2-benzimidazolone as potassium channel and/or neuron activity modulators
CN101868443A (en) 2007-09-20 2010-10-20 特拉维夫大学拉莫特有限公司 N-phenyl anthranilic acid derivatives and uses thereof
US20120022116A1 (en) * 2010-07-20 2012-01-26 Huayun Deng Compositions and methods for the treatment of pathological condition(s) related to gpr35 and/or gpr35-herg complex
US9376376B2 (en) 2012-03-14 2016-06-28 Sinochem Corporation Substitute diphenylamine compounds use thereof as antitumor agents
CN105267214B (en) * 2014-07-21 2019-04-30 沈阳化工研究院有限公司 Application of N-heteroarylaniline compounds as antitumor drugs

Citations (30)

* Cited by examiner, † Cited by third party
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US3652762A (en) * 1970-04-14 1972-03-28 Ciba Geigy Corp Pharmaceutical compositions and methods employing substituted derivatives of 2-anilinophenylacetic acids and esters
FR2411825A1 (en) * 1977-02-26 1979-07-13 Hokuriku Pharmaceutical N- (TRIFLUOROMETHYL-3-PHENYL) ALKYL ANTHRANILATE, USED AS ANTI-INFLAMMATORY AGENT
FR2462420A1 (en) * 1979-07-31 1981-02-13 Simes O-ALCOXYCARBONYL-PHENYL ESTERS OF ANTHRANILIC ACID, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
EP0131790A2 (en) * 1983-07-01 1985-01-23 Troponwerke GmbH & Co. KG Etofenamate preparation
US4734434A (en) * 1986-03-11 1988-03-29 Rorer Pharmaceutical Corporation Method for the treatment of pruritus and composition for the use therein
JPS63275593A (en) * 1987-05-08 1988-11-14 Fujirebio Inc β-aminoethyl phosphate derivative
JPS63275549A (en) * 1987-05-07 1988-11-14 ファブリカ、エスパニョ−ラ、デ、プロドゥクトス、キミコス、イ、ファルマセウティコス、ソシエダ、アノニマ　（エ−フェア−エ−エ−セ） Diethyleneglycol ester and medicine containing same
EP0307599A1 (en) * 1987-08-12 1989-03-22 Bayer Ag Medicaments for the region of the buccal cavity
JPH0196158A (en) * 1987-10-09 1989-04-14 Santen Pharmaceut Co Ltd Anti-inflammatory agent
EP0335164A2 (en) * 1988-03-31 1989-10-04 Merckle GmbH Ester derivatives of neopentanol, process for their preparation and their use as medicines
EP0336147A2 (en) * 1988-03-31 1989-10-11 Merckle GmbH Diethylene glycol monoesters, process for their preparation and their use as medicines
US5017604A (en) * 1990-04-11 1991-05-21 Warner-Lambert Company Novel fenamic acid methyl hydroxamate derivatives having cyclooxygenase and 5-lipoxygenase inhibition
WO1999001421A1 (en) * 1997-07-01 1999-01-14 Warner-Lambert Company 2-(4-bromo or 4-iodo phenylamino) benzoic acid derivatives and their use as mek inhibitors
WO2001093680A1 (en) * 2000-06-02 2001-12-13 Medinox, Inc. Protected forms of a combination of pharmacologically active agents and uses therefor
US6355666B1 (en) * 2000-06-23 2002-03-12 Medinox, Inc. Protected forms of pharmacologically active agents and uses therefor
WO2002065977A2 (en) * 2001-02-20 2002-08-29 Israel Institute For Biological Research Compounds co-inducing cholinergic up-regulation and inflammation down-regulation and uses thereof
WO2003103602A2 (en) * 2002-06-11 2003-12-18 Nitromed, Inc. Nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use
WO2004000300A1 (en) * 2002-06-25 2003-12-31 Nicox S.A. Cyclooxygenase-2 inhibitors
WO2004026808A1 (en) * 2002-09-20 2004-04-01 Nicox Sa. Manufacturing process for no-donating compounds such as no-donating diclofenac
WO2004052840A1 (en) * 2002-12-12 2004-06-24 Galderma Research & Development, S.N.C. Compounds which modulate pparϝ type receptors, and use thereof in cosmetic or pharmaceutical compositions
WO2005009975A2 (en) * 2003-07-24 2005-02-03 Warner-Lambert Company Llc Benzimidazole derivatives as mek inhibitors
US20050250833A1 (en) * 2002-10-21 2005-11-10 Ramot At Tel Aviv University Ltd. Derivatives of N-phenylanthranilic acid and 2-benzimidazolone as potassium channel and/or neuron activity modulators
WO2006042387A1 (en) * 2004-10-21 2006-04-27 Cmax Otimizacão De Resultados S C Ltda Drugs derived from diclofenac containing no-donor heterocycles, composition and method of inflammation treatment
WO2006117316A1 (en) * 2005-04-29 2006-11-09 Nycomed Gmbh Mutual prodrug compounds for use us antiinflammatory agents with gastrointestinal protective activity
US20080004245A1 (en) * 2005-05-27 2008-01-03 Antibe Therapeutics Inc. Hydrogen sulfide derivatives of non-steroidal anti-inflammatory drugs
WO2008012602A1 (en) * 2006-07-25 2008-01-31 Techfields Biochem Co. Ltd Positively charged water-soluble prodrugs of diclofenac with very fast skin penetration rate
WO2008029199A1 (en) * 2006-09-03 2008-03-13 Techfields Biochem Co. Ltd Positively charged water-soluble prodrugs of n-arylanthranilic acids with very fast skin penetration rate
US7378442B1 (en) * 2007-03-11 2008-05-27 Sami Labs Limited Chemical entities with multiple modes of anti-inflammatory action
WO2009007827A2 (en) * 2007-07-10 2009-01-15 Chemisches Institut Schaefer Ag Novel diclofenac esters and uses thereof
WO2009037707A2 (en) * 2007-09-20 2009-03-26 Ramot At Tel Aviv University Ltd. N-phenyl anthranilic acid derivatives and uses thereof

Patent Citations (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3652762A (en) * 1970-04-14 1972-03-28 Ciba Geigy Corp Pharmaceutical compositions and methods employing substituted derivatives of 2-anilinophenylacetic acids and esters
FR2411825A1 (en) * 1977-02-26 1979-07-13 Hokuriku Pharmaceutical N- (TRIFLUOROMETHYL-3-PHENYL) ALKYL ANTHRANILATE, USED AS ANTI-INFLAMMATORY AGENT
FR2462420A1 (en) * 1979-07-31 1981-02-13 Simes O-ALCOXYCARBONYL-PHENYL ESTERS OF ANTHRANILIC ACID, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
EP0131790A2 (en) * 1983-07-01 1985-01-23 Troponwerke GmbH & Co. KG Etofenamate preparation
US4734434A (en) * 1986-03-11 1988-03-29 Rorer Pharmaceutical Corporation Method for the treatment of pruritus and composition for the use therein
JPS63275549A (en) * 1987-05-07 1988-11-14 ファブリカ、エスパニョ−ラ、デ、プロドゥクトス、キミコス、イ、ファルマセウティコス、ソシエダ、アノニマ　（エ−フェア−エ−エ−セ） Diethyleneglycol ester and medicine containing same
JPS63275593A (en) * 1987-05-08 1988-11-14 Fujirebio Inc β-aminoethyl phosphate derivative
EP0307599A1 (en) * 1987-08-12 1989-03-22 Bayer Ag Medicaments for the region of the buccal cavity
JPH0196158A (en) * 1987-10-09 1989-04-14 Santen Pharmaceut Co Ltd Anti-inflammatory agent
EP0335164A2 (en) * 1988-03-31 1989-10-04 Merckle GmbH Ester derivatives of neopentanol, process for their preparation and their use as medicines
EP0336147A2 (en) * 1988-03-31 1989-10-11 Merckle GmbH Diethylene glycol monoesters, process for their preparation and their use as medicines
US5017604A (en) * 1990-04-11 1991-05-21 Warner-Lambert Company Novel fenamic acid methyl hydroxamate derivatives having cyclooxygenase and 5-lipoxygenase inhibition
WO1999001421A1 (en) * 1997-07-01 1999-01-14 Warner-Lambert Company 2-(4-bromo or 4-iodo phenylamino) benzoic acid derivatives and their use as mek inhibitors
WO2001093680A1 (en) * 2000-06-02 2001-12-13 Medinox, Inc. Protected forms of a combination of pharmacologically active agents and uses therefor
US6355666B1 (en) * 2000-06-23 2002-03-12 Medinox, Inc. Protected forms of pharmacologically active agents and uses therefor
WO2002065977A2 (en) * 2001-02-20 2002-08-29 Israel Institute For Biological Research Compounds co-inducing cholinergic up-regulation and inflammation down-regulation and uses thereof
WO2003103602A2 (en) * 2002-06-11 2003-12-18 Nitromed, Inc. Nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use
WO2004000300A1 (en) * 2002-06-25 2003-12-31 Nicox S.A. Cyclooxygenase-2 inhibitors
WO2004026808A1 (en) * 2002-09-20 2004-04-01 Nicox Sa. Manufacturing process for no-donating compounds such as no-donating diclofenac
US20050250833A1 (en) * 2002-10-21 2005-11-10 Ramot At Tel Aviv University Ltd. Derivatives of N-phenylanthranilic acid and 2-benzimidazolone as potassium channel and/or neuron activity modulators
WO2004052840A1 (en) * 2002-12-12 2004-06-24 Galderma Research & Development, S.N.C. Compounds which modulate pparϝ type receptors, and use thereof in cosmetic or pharmaceutical compositions
WO2005009975A2 (en) * 2003-07-24 2005-02-03 Warner-Lambert Company Llc Benzimidazole derivatives as mek inhibitors
WO2006042387A1 (en) * 2004-10-21 2006-04-27 Cmax Otimizacão De Resultados S C Ltda Drugs derived from diclofenac containing no-donor heterocycles, composition and method of inflammation treatment
WO2006117316A1 (en) * 2005-04-29 2006-11-09 Nycomed Gmbh Mutual prodrug compounds for use us antiinflammatory agents with gastrointestinal protective activity
US20080004245A1 (en) * 2005-05-27 2008-01-03 Antibe Therapeutics Inc. Hydrogen sulfide derivatives of non-steroidal anti-inflammatory drugs
WO2008012602A1 (en) * 2006-07-25 2008-01-31 Techfields Biochem Co. Ltd Positively charged water-soluble prodrugs of diclofenac with very fast skin penetration rate
WO2008029199A1 (en) * 2006-09-03 2008-03-13 Techfields Biochem Co. Ltd Positively charged water-soluble prodrugs of n-arylanthranilic acids with very fast skin penetration rate
US7378442B1 (en) * 2007-03-11 2008-05-27 Sami Labs Limited Chemical entities with multiple modes of anti-inflammatory action
WO2009007827A2 (en) * 2007-07-10 2009-01-15 Chemisches Institut Schaefer Ag Novel diclofenac esters and uses thereof
WO2009037707A2 (en) * 2007-09-20 2009-03-26 Ramot At Tel Aviv University Ltd. N-phenyl anthranilic acid derivatives and uses thereof

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
"Supporting Text S1. Synthesis of Compounds", 20071226, 26 December 2007 (2007-12-26), pages 1 - 13, XP007908469 *
BONINA F ET AL: "Oligoethylene ester derivatives of ketoprofen, naproxen and diclofenac as oral prodrugs: a pharmacological evaluation", PHARMAZIE, DIE, GOVI VERLAG, ESCHBORN, DE, vol. 57, no. 8, 1 August 2002 (2002-08-01), pages 552 - 555, XP001539451, ISSN: 0031-7144 *
CENZO CONGIU ET AL: "New Potential Anticancer Agents Based on the Anthranilic Acid Scaffold. Synthesis and Evaluation of Biological Activity", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 48, no. 26, 1 January 2005 (2005-01-01), pages 8245 - 8252, XP007908449, ISSN: 0022-2623, [retrieved on 20051115] *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KUTSUMA, TERUO ET AL: "Preparation of .beta.-aminoethyl phosphates containing indomethacin- and diclofenac residues as analgesic inflammation inhibitors", XP002526999, retrieved from STN Database accession no. 1989:193120 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; ORJALES VENERO, AURELIO ET AL: "Preparation of hydroxyethoxyethyl 2-(2,6-dichlorophenylamino)phenylacetate as an analgesic and antiinflammatory", XP002526998, retrieved from STN Database accession no. 1989:172889 *
FREGNAN G B ET AL: "Local anti-inflammatory properties of etoclofene. A new fenamate derivative", PHARMACOLOGY, S. KARGER AG, vol. 11, no. 4, 1 January 1974 (1974-01-01), pages 213 - 219, XP009116638, ISSN: 0031-7012 *
KALGUTKAR A S ET AL: "Amide Derivatives of Meclofenamic Acid as Selective Cyclooxygenase-2 Inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 12, 1 January 2002 (2002-01-01), pages 521 - 524, XP002319950, ISSN: 0960-894X *
PERETZ ASHER ET AL: "A tale of switched functions: from cyclooxygenase inhibition to M-channel modulation in new diphenylamine derivatives", PLOS ONE, PUBLIC LIBRARY OF SCIENCE, SAN FRANCISCO, CA, US, vol. 2, no. 12, 26 December 2007 (2007-12-26), pages e1332 - 1, XP009116544, ISSN: 1932-6203 *

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