CA2415169C - Novel c-4 substituted retinoids - Google Patents

Novel c-4 substituted retinoids Download PDF

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Publication number
CA2415169C
CA2415169C CA2415169A CA2415169A CA2415169C CA 2415169 C CA2415169 C CA 2415169C CA 2415169 A CA2415169 A CA 2415169A CA 2415169 A CA2415169 A CA 2415169A CA 2415169 C CA2415169 C CA 2415169C
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CA
Canada
Prior art keywords
atra
group
retinoic acid
pharmaceutical composition
compound
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.)
Expired - Fee Related
Application number
CA2415169A
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English (en)
French (fr)
Other versions
CA2415169A1 (en
Inventor
Vincent C. O. Njar
Angela M. H. Brodie
Ivo P. Nnane
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.)
University of Maryland, Baltimore
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University of Maryland, Baltimore
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Publication of CA2415169A1 publication Critical patent/CA2415169A1/en
Application granted granted Critical
Publication of CA2415169C publication Critical patent/CA2415169C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • 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
    • 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
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/61—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
    • C07D331/02—Three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (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)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2415169A 2000-07-11 2001-07-11 Novel c-4 substituted retinoids Expired - Fee Related CA2415169C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US21746500P 2000-07-11 2000-07-11
US60/217,465 2000-07-11
PCT/US2001/016524 WO2002003912A2 (en) 2000-07-11 2001-07-11 Novel c-4 substituted retinoids

Publications (2)

Publication Number Publication Date
CA2415169A1 CA2415169A1 (en) 2002-01-17
CA2415169C true CA2415169C (en) 2010-06-01

Family

ID=22811193

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2415169A Expired - Fee Related CA2415169C (en) 2000-07-11 2001-07-11 Novel c-4 substituted retinoids

Country Status (6)

Country Link
US (2) US7265143B2 (enExample)
EP (1) EP1305274A4 (enExample)
JP (1) JP2004509073A (enExample)
AU (2) AU7126501A (enExample)
CA (1) CA2415169C (enExample)
WO (1) WO2002003912A2 (enExample)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050107352A1 (en) * 1999-08-26 2005-05-19 Parks L. D. Method of treating benign prostatic hyperplasia
US20040242689A1 (en) * 1999-08-26 2004-12-02 Parks L. Dean Method of treating benign prostatic hyperplasia and other benign prostate conditions
FR2894577B1 (fr) * 2005-12-14 2008-02-22 Fabre Pierre Dermo Cosmetique Nouveaux composes polyinsatures, leur procede de preparation et les compositions les contenant.
FR2894465B1 (fr) 2005-12-14 2010-09-10 Fabre Pierre Dermo Cosmetique Utilisation de composes polyinsatures en tant qu'agents blanchissants
GB2454118B (en) 2007-06-06 2010-06-02 Univ Maryland Hdac inhibitors and hormone targeted drugs for the treatment of cancer
EP2164480A1 (en) * 2007-06-06 2010-03-24 University of Maryland, Baltimore Mutual prodrugs and methods to treat cancer
US9156792B2 (en) * 2008-05-09 2015-10-13 University Of Maryland, Baltimore Retinamide and uses thereof
US20120190716A1 (en) * 2009-08-05 2012-07-26 Oehlen Lambertus J W M Methods and uses of cytochrome p450 inhibitors
US10414760B2 (en) 2016-11-29 2019-09-17 Angion Biomedica Corp. Cytochrome P450 inhibitors and uses thereof
US8513291B2 (en) 2010-06-01 2013-08-20 Angion Biomedica Corp. Cytochrome P450 inhibitors and uses thereof
US9248120B2 (en) 2011-08-23 2016-02-02 The Board Of Trustees Of The Leland Stanford Junior University Reversing intestinal inflammation by inhibiting retinoic acid metabolism
WO2014093960A1 (en) * 2012-12-16 2014-06-19 Angion Biomedica Corp. Compositions and methods for treating disease
CA2957785C (en) 2014-08-11 2023-01-03 Angion Biomedica Corporation Cytochrome p450 inhibitors and uses thereof
EP3221284B1 (en) 2014-11-20 2025-09-10 University of Maryland, Baltimore 13-cis-ramba retinamides that degrade mnks for treating cancer
CA2970819A1 (en) 2014-12-31 2016-07-07 Angion Biomedica Corp. Methods and agents for treating disease
CN109675256B (zh) * 2019-03-02 2023-05-23 哈尔滨理工大学 一种内齿啮合式乳腺癌术后康复训练装置及使用方法
CN115087487A (zh) * 2019-12-19 2022-09-20 马里兰大学巴尔的摩分校 使用维甲酰胺治疗皮肤病的组合物和方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4169103A (en) * 1978-04-12 1979-09-25 Hoffmann-La Roche Inc. Nonatetraenoic acid derivatives
US5124083A (en) * 1990-08-30 1992-06-23 Southern Research Institute 3-substituted and 3,3-disubstituted 4-oxoretinoic acids and their esters
US5808120A (en) * 1995-08-22 1998-09-15 Wisconsin Alumni Research Foundation Method of synthesis of retinoic acid

Also Published As

Publication number Publication date
EP1305274A4 (en) 2005-10-12
US20120122908A1 (en) 2012-05-17
AU2001271265B2 (en) 2005-01-06
US20030162823A1 (en) 2003-08-28
WO2002003912A2 (en) 2002-01-17
JP2004509073A (ja) 2004-03-25
CA2415169A1 (en) 2002-01-17
US7265143B2 (en) 2007-09-04
AU7126501A (en) 2002-01-21
WO2002003912A3 (en) 2002-07-18
EP1305274A2 (en) 2003-05-02

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