CA2901581C - Cyclohexenone compositions and process for making thereof - Google Patents

Cyclohexenone compositions and process for making thereof Download PDF

Info

Publication number
CA2901581C
CA2901581C CA2901581A CA2901581A CA2901581C CA 2901581 C CA2901581 C CA 2901581C CA 2901581 A CA2901581 A CA 2901581A CA 2901581 A CA2901581 A CA 2901581A CA 2901581 C CA2901581 C CA 2901581C
Authority
CA
Canada
Prior art keywords
compound
aryl
nr5r6
independently
formula
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
CA2901581A
Other languages
English (en)
French (fr)
Other versions
CA2901581A1 (en
Inventor
Sheng-Yung Liu
Wu-Che Wen
Chih-Ming Chen
Hsiu-Yi CHENG
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.)
Golden Biotechnology Corp
Original Assignee
Golden Biotechnology Corp
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 Golden Biotechnology Corp filed Critical Golden Biotechnology Corp
Publication of CA2901581A1 publication Critical patent/CA2901581A1/en
Application granted granted Critical
Publication of CA2901581C publication Critical patent/CA2901581C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07C403/02—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 containing only carbon and hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA2901581A 2013-02-20 2014-02-20 Cyclohexenone compositions and process for making thereof Expired - Fee Related CA2901581C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361767212P 2013-02-20 2013-02-20
US61/767,212 2013-02-20
PCT/US2014/017284 WO2014130618A1 (en) 2013-02-20 2014-02-20 Cyclohexenone compositions and process for making thereof

Publications (2)

Publication Number Publication Date
CA2901581A1 CA2901581A1 (en) 2014-08-28
CA2901581C true CA2901581C (en) 2020-07-14

Family

ID=51391788

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2901581A Expired - Fee Related CA2901581C (en) 2013-02-20 2014-02-20 Cyclohexenone compositions and process for making thereof

Country Status (9)

Country Link
US (2) US9365481B2 (enExample)
EP (1) EP2958883B1 (enExample)
JP (2) JP6706018B2 (enExample)
CN (1) CN105263893A (enExample)
CA (1) CA2901581C (enExample)
ES (1) ES2713181T3 (enExample)
HK (1) HK1220174A1 (enExample)
TW (1) TWI612026B (enExample)
WO (1) WO2014130618A1 (enExample)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI612026B (zh) * 2013-02-20 2018-01-21 國鼎生物科技股份有限公司 環己烯酮組成物及其製造方法
WO2016037566A1 (en) * 2014-09-09 2016-03-17 Ching-Feng Weng Use of antroqiononol for treating obesity, and process for preparation of antroquinonol
US20160237012A1 (en) * 2015-02-17 2016-08-18 Golden Biotechnology Corporation Anticancer agents and process of making thereof
AU2017219871B2 (en) * 2016-02-17 2020-09-03 Golden Biotechnology Corporation Compositions and methods for treating liver cancer
TW201831436A (zh) * 2017-02-24 2018-09-01 郭盈妤 分離自牛樟芝的化合物及其用途
AU2018247249B2 (en) 2017-12-20 2023-10-19 Golden Biotechnology Corporation Therapeutic compositions for treating pancreatic cancer
US11406605B2 (en) 2017-12-20 2022-08-09 Golden Biotechnology Corporation Therapeutic compositions for treating pancreatic cancer
CN111018686B (zh) * 2019-11-19 2020-09-22 南通大学 6-苄亚基-2-芳基乙炔基环己烯酮衍生物及其制备方法和医药用途
JP7781425B2 (ja) 2020-05-08 2025-12-08 ゴールデン バイオテクノロジー コーポレーション Ｒｎａウイルス性疾患を処置するための方法および組成物
TW202532056A (zh) * 2024-01-31 2025-08-16 國鼎生物科技股份有限公司 用於治療肝癌的治療組合物

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200829234A (en) * 2007-01-08 2008-07-16 Golden Biotechnology Corp Antrodia camphorata isophorone extract
CN101417934B (zh) * 2007-10-24 2012-04-18 国鼎生物科技股份有限公司 分离自牛樟芝萃取物的化合物
TWI389699B (zh) * 2009-02-13 2013-03-21 高雄醫學大學 用於誘導細胞凋亡之樟芝子實體乙醇萃取物及其製備方法
TW201109013A (en) * 2009-09-09 2011-03-16 Golden Biotechnology Corp Cyclohexenone chemical compounds of Antrodia cinnamomea for suppressing the growth of the Lymphoma tumor cell
TW201109023A (en) * 2009-09-09 2011-03-16 Golden Biotechnology Corp Cyclohexenone compound of Antrodia cinnomomea that suppresses growth of tumor cell of colorectal cancer
TWI394566B (zh) * 2009-09-09 2013-05-01 國鼎生物科技股份有限公司 Used to inhibit the growth of ovarian cancer tumor cells of the cattle camphor cyclohexene ketone compounds
US8309611B2 (en) * 2010-09-20 2012-11-13 Golden Biotechnology Corporation Methods and compositions for treating lung cancer
TWI444189B (zh) * 2011-05-31 2014-07-11 財團法人台灣基督長老教會馬偕紀念社會事業基金會馬偕紀念醫院 羊毛甾醇－８，２４－二烯－３β，１５α，２１－三醇抑制腫瘤細胞生長之用途
EP2717865A4 (en) * 2011-06-10 2014-11-12 Golden Biotechnology Corp METHOD AND COMPOSITIONS FOR TREATING BRAIN CANCER
TWI612026B (zh) * 2013-02-20 2018-01-21 國鼎生物科技股份有限公司 環己烯酮組成物及其製造方法

Also Published As

Publication number Publication date
US9365481B2 (en) 2016-06-14
US20160251308A1 (en) 2016-09-01
JP2019142854A (ja) 2019-08-29
HK1220174A1 (zh) 2017-04-28
JP2016513122A (ja) 2016-05-12
CA2901581A1 (en) 2014-08-28
EP2958883B1 (en) 2019-01-30
WO2014130618A1 (en) 2014-08-28
TWI612026B (zh) 2018-01-21
US20150018567A1 (en) 2015-01-15
TW201500330A (zh) 2015-01-01
CN105263893A (zh) 2016-01-20
JP6706018B2 (ja) 2020-06-03
ES2713181T3 (es) 2019-05-20
EP2958883A1 (en) 2015-12-30
EP2958883A4 (en) 2016-08-17

Similar Documents

Publication Publication Date Title
CN115490697B (zh) 一种手性氮杂螺[4,5]-癸胺的不对称合成方法
EP2958883B1 (en) Cyclohexenone compositions and process for making thereof
JP6511613B2 (ja) ハリコンドリンＢの大環状Ｃ１−ケト類似体の製造のための合成方法及び該方法に有用な中間体、例えば−ＳＯ２−（ｐ−トリル）基を含有する中間体
RS62515B1 (sr) Prekursor leka – derivat aminokiselina
CN112321514B (zh) 一种手性巴比妥酸类化合物及其制备方法
CN113292574B (zh) 一类手性多环的托品烷化合物及其制备方法和用途
CN105801591B (zh) 一种五环吡咯类生物碱及其制备方法
Takasu et al. Auto-tandem catalysis: facile synthesis of substituted alkylidenecyclohexanones by domino (4+ 2) cycloaddition–elimination reaction
Wiese Total synthesis of the antiviral natural products Cleistocaltone A and B
Myeong et al. Stereoselective allylation reactions of acyclic and chiral α-amino-β-hydroxy aldehydes 3: Total synthesis of (+)-1-epi-castanospermine
US6723853B2 (en) Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins
AU2017283772B2 (en) Process for producing lamivudine and emtricitabine
CA3023114C (en) Process for producing lamivudine and emtricitabine
Aguirre Kohnen Synthesis of 3-aminocyclobutenones via [2+ 2] cycloaddition of ynamides and ketenes
WO2016133940A1 (en) Anticancer agents and process of making thereof
Xu et al. Synthesis of novel heptaplatin derivatives and evaluation of their ability to inhibit proliferation of cancer cell lines
Weaver Frisky Dienes & Hot Electrophiles: Development of synthetic methods to access key structural features of tetrapetalone A
Fan Studies toward the Total Synthesis of Biselides & Radical Fluorination of Aliphatic Compounds
van Maarseveen et al. Transformations of the tetracyclic skeleton of eudistomins by neighboring‐group participation in the Mitsunobu reaction
KR20050003080A (ko) 3,4-디히드로퀴나졸린 유도체 및 그의 제조 방법
Xu Towards the total synthesis of nakadomarin A
Zhang Part I. Novel C (2) Symmetric Lewis Acid Catalysts Based Upon a Camphor Lactam Template for Catalytic Asymmetric Cycloaddition Reactions. Part II. The Total Synthesis of (+)-Laurenyne Employing a Template Driven S (N) 2'Cyclization and a Retro-Claisen Rearrangement
Njoya Contraction-expansion protocols
Wang SYNTHETIC, CHEMICAL AND BIOLOGICAL STUDIES OF FR901464 ANALOGUES
KR20050062940A (ko) 디이소프로필((1-((2-아미노-6-할로-9ｈ-퓨린-9-일)메틸)사이클로프로필)옥시)-메틸포스포네이트의 새로운 제조방법

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20190219

MKLA Lapsed

Effective date: 20220823

MKLA Lapsed

Effective date: 20210222