CA2715662C - Phenylpropanoid diglycerides for the treatment of cancer - Google Patents

Phenylpropanoid diglycerides for the treatment of cancer Download PDF

Info

Publication number
CA2715662C
CA2715662C CA2715662A CA2715662A CA2715662C CA 2715662 C CA2715662 C CA 2715662C CA 2715662 A CA2715662 A CA 2715662A CA 2715662 A CA2715662 A CA 2715662A CA 2715662 C CA2715662 C CA 2715662C
Authority
CA
Canada
Prior art keywords
compound
alkoxy
alkylcarbonyloxy
formula
use according
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.)
Active
Application number
CA2715662A
Other languages
English (en)
French (fr)
Other versions
CA2715662A1 (en
Inventor
Alexander Macgregor
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.)
Individual
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 CA2715662A1 publication Critical patent/CA2715662A1/en
Application granted granted Critical
Publication of CA2715662C publication Critical patent/CA2715662C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • 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
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • 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
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Epoxy Compounds (AREA)
CA2715662A 2009-10-09 2010-10-08 Phenylpropanoid diglycerides for the treatment of cancer Active CA2715662C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US25028709P 2009-10-09 2009-10-09
US61/250,287 2009-10-09

Publications (2)

Publication Number Publication Date
CA2715662A1 CA2715662A1 (en) 2010-12-14
CA2715662C true CA2715662C (en) 2013-05-07

Family

ID=43352967

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2715662A Active CA2715662C (en) 2009-10-09 2010-10-08 Phenylpropanoid diglycerides for the treatment of cancer

Country Status (20)

Country Link
US (2) US9061993B2 (https=)
EP (1) EP2486026B1 (https=)
JP (1) JP5529280B2 (https=)
CN (1) CN102264713A (https=)
BR (1) BR112012008204A2 (https=)
CA (1) CA2715662C (https=)
CY (1) CY1123161T1 (https=)
DK (1) DK2486026T3 (https=)
ES (1) ES2810906T3 (https=)
HR (1) HRP20201217T1 (https=)
HU (1) HUE051549T2 (https=)
LT (1) LT2486026T (https=)
MX (1) MX360417B (https=)
MY (2) MY160378A (https=)
PL (1) PL2486026T3 (https=)
PT (1) PT2486026T (https=)
RS (1) RS60667B1 (https=)
SI (1) SI2486026T1 (https=)
SM (1) SMT202000428T1 (https=)
WO (1) WO2011041907A1 (https=)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8907117B2 (en) * 2011-09-08 2014-12-09 Henry Lowe Anti-tumor and anti-inflammatory dicinnamoyl-glycerol esters and their analogues
US9907786B2 (en) 2014-10-21 2018-03-06 Ions Pharmaceutical S.À R.L. Therapeutic compositions containing harmine and isovanillin components, and methods of use thereof
US10092550B2 (en) 2014-10-21 2018-10-09 Ions Pharmaceutical S.À R.L. Therapeutic compositions containing curcumin, harmine, and isovanillin components, and methods of use thereof
US20160106687A1 (en) 2014-10-21 2016-04-21 Life Plus, LLC Human therapeutic agents
US12129265B2 (en) 2020-07-21 2024-10-29 Ankh Life Sciences Limited Therapeutic agents and uses thereof

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3857873A (en) 1974-02-11 1974-12-31 Warner Lambert Co 3-hydroxy-5-(3-(substituted-amino)-2-hydroxypropoxy)-benzyl alcohols
CH648753A5 (de) * 1981-07-22 1985-04-15 Givaudan & Cie Sa Lichtschutzmittel.
CN1238333C (zh) * 2003-06-18 2006-01-25 清华大学 药物化合物菠萝酰酯及其制备方法和用途
US7713556B2 (en) 2006-12-08 2010-05-11 Henry Lowe Anti-tumor and anti-inflammatory extracts of plant biomass and their uses
JP2010515685A (ja) * 2007-01-08 2010-05-13 アンドロサイエンス コーポレーション （置換フェニル）−プロペナール部分を伴う化合物、その誘導体、生物学的活性およびその使用
TWI383251B (zh) * 2008-01-16 2013-01-21 Eternal Chemical Co Ltd 感光型聚醯亞胺
KR101074149B1 (ko) * 2009-04-15 2011-10-17 한밭대학교 산학협력단 신규 폴리페놀/폴리페놀 컨쥬게이트 화합물 및 그의 용도
US8907117B2 (en) * 2011-09-08 2014-12-09 Henry Lowe Anti-tumor and anti-inflammatory dicinnamoyl-glycerol esters and their analogues

Also Published As

Publication number Publication date
CY1123161T1 (el) 2021-10-29
ES2810906T3 (es) 2021-03-09
LT2486026T (lt) 2020-09-10
US10052301B2 (en) 2018-08-21
JP5529280B2 (ja) 2014-06-25
US9061993B2 (en) 2015-06-23
EP2486026B1 (en) 2020-06-24
EP2486026A4 (en) 2015-07-01
MX360417B (es) 2018-10-25
SMT202000428T1 (it) 2020-09-10
WO2011041907A1 (en) 2011-04-14
JP2013507327A (ja) 2013-03-04
EP2486026A1 (en) 2012-08-15
HRP20201217T1 (hr) 2020-12-11
HUE051549T2 (hu) 2021-10-28
CN102264713A (zh) 2011-11-30
MY160378A (en) 2017-03-15
PT2486026T (pt) 2020-08-21
US20150246014A1 (en) 2015-09-03
RS60667B1 (sr) 2020-09-30
PL2486026T3 (pl) 2020-11-02
CA2715662A1 (en) 2010-12-14
MX2012004160A (es) 2012-09-07
US20110086912A1 (en) 2011-04-14
DK2486026T3 (da) 2020-08-17
BR112012008204A2 (pt) 2017-07-18
MY187188A (en) 2021-09-09
SI2486026T1 (sl) 2020-10-30

Similar Documents

Publication Publication Date Title
Ashour et al. 1, 2, 3-Triazole-Chalcone hybrids: Synthesis, in vitro cytotoxic activity and mechanistic investigation of apoptosis induction in multiple myeloma RPMI-8226
CA2715662C (en) Phenylpropanoid diglycerides for the treatment of cancer
AU2008205312B2 (en) Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and uses thereof
Nicolov et al. Cocrystal formation of betulinic acid and ascorbic acid: Synthesis, physico-chemical assessment, antioxidant, and antiproliferative activity
Cao et al. Synthesis and biological evaluation of novel pyranochalcone derivatives as a new class of microtubule stabilizing agents
CA2911352A1 (en) Ester derivatives of androgen receptor modulators and methods for their use
An et al. Synthesis, in vitro and in vivo evaluation of new hybrids of millepachine and phenstatin as potent tubulin polymerization inhibitors
CN101485651B (zh) 二氢查尔酮衍生物及其应用
Karimikia et al. Colchicine-like β-acetamidoketones as inhibitors of microtubule polymerization: Design, synthesis and biological evaluation of in vitro anticancer activity
Liu et al. Synthesis of a celastrol derivative as a cancer stem cell inhibitor through regulation of the STAT3 pathway for treatment of ovarian cancer
KR20170129688A (ko) 인돌아세트산의 코어구조를 함유하는 화합물 및 그의 용도
EP1268387B1 (en) Specific salt forms of triphenylethylene derivatives as selective estrogen receptor modulators
HK1164842A (en) Derivatives of di(phenylpropanoid) glycerol for the treatment of cancer
CN101230015B (zh) 含酰胺取代基的取代桂皮酸衍生物及其肿瘤细胞毒性
CN101157711B (zh) 一种具有抗肿瘤活性的化合物及其用途
TWI419687B (zh) 作用於微小管抗癌藥物２’,５’－ｄｉｍｅｔｈｏｘｙｃｈａｌｃｏｎｅ衍生物之合成與活性評估
Wang et al. Synthesis and Application of Hydroquinone with Heptadecatrienyl Side Chain for Inhibition of SARS-CoV-2
Danova Synthesis and biological activities of chalcone derivatives
Nichols Aggie Digital Collections and Scholarshi p
Adegbulugbe Synthesis and Evaluation of Tetramethoxy Stilbenes Related to Combretastatin A-4 as Potential Anticancer Agents
US20130079396A1 (en) Anticancer and Tubulin Polymerisation Inhibition Activity of Benzylidene Indanones and Process of Preparing the Same
Wang et al. Synthesis and Application of Hydroquinone with Heptadecatrienyl Side Chain for Inhibition
WO2025029660A1 (en) Compounds with selectivity for certain cancers
EP3322687B1 (en) 2-benzyl-indanone compounds as anticancer agent and a process for preparation thereof
Nichols The Synthesis And Characterization Of 3-Nitro-2-Styrenyl Benzoic Acid Amide Derivatives As Potential Cancer Chemopreventives

Legal Events

Date Code Title Description
EEER Examination request
W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: N-6-6-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20251204

H13 Ip right lapsed

Free format text: ST27 STATUS EVENT CODE: N-6-6-H10-H13-H100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE AND LATE FEE NOT PAID BY DEADLINE OF NOTICE

Effective date: 20260323