WO2008048117A3 - Synthesis of 5,6-dimethyl-9-oxo-9h-xanthen-4-yl- acetic acid (dmxaa) - Google Patents

Synthesis of 5,6-dimethyl-9-oxo-9h-xanthen-4-yl- acetic acid (dmxaa) Download PDF

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Publication number
WO2008048117A3
WO2008048117A3 PCT/NZ2007/000307 NZ2007000307W WO2008048117A3 WO 2008048117 A3 WO2008048117 A3 WO 2008048117A3 NZ 2007000307 W NZ2007000307 W NZ 2007000307W WO 2008048117 A3 WO2008048117 A3 WO 2008048117A3
Authority
WO
WIPO (PCT)
Prior art keywords
dmxaa
xanthen
oxo
acetic acid
dimethyl
Prior art date
Application number
PCT/NZ2007/000307
Other languages
French (fr)
Other versions
WO2008048117A2 (en
Inventor
William Alexander Denny
Shangjin Yang
Original Assignee
Auckland Uniservices Ltd
William Alexander Denny
Shangjin Yang
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 Auckland Uniservices Ltd, William Alexander Denny, Shangjin Yang filed Critical Auckland Uniservices Ltd
Publication of WO2008048117A2 publication Critical patent/WO2008048117A2/en
Publication of WO2008048117A3 publication Critical patent/WO2008048117A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/84—Xanthenes 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 in position 9
    • C07D311/86—Oxygen atoms, e.g. xanthones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic

Abstract

The present invention provides an improved synthesis of 9-oxo-9H-xanthen-4-yl-acetic acids, and in particular 5,6-dimethyl-9-oxo-9H-xanthen-4-yl-acetic acid (also known as 5,6-dimethylxanthenone-4-acetic acid and DMXAA and ASA404) from certain substituted benzoic acids. DMXAA is an antivascular agent used in the treatment of cancer.
PCT/NZ2007/000307 2006-10-17 2007-10-17 Synthesis of 5,6-dimethyl-9-oxo-9h-xanthen-4-yl- acetic acid (dmxaa) WO2008048117A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NZ550578 2006-10-17
NZ55057806 2006-10-17

Publications (2)

Publication Number Publication Date
WO2008048117A2 WO2008048117A2 (en) 2008-04-24
WO2008048117A3 true WO2008048117A3 (en) 2008-06-19

Family

ID=39314478

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NZ2007/000307 WO2008048117A2 (en) 2006-10-17 2007-10-17 Synthesis of 5,6-dimethyl-9-oxo-9h-xanthen-4-yl- acetic acid (dmxaa)

Country Status (1)

Country Link
WO (1) WO2008048117A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018083635A2 (en) 2016-11-04 2018-05-11 Auckland Uniservices Limited Tricyclic heterocyclic derivatives and uses thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0278176B1 (en) * 1986-12-23 1994-03-09 Warner-Lambert Company Compounds having antitumour and antibacterial properties

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0278176B1 (en) * 1986-12-23 1994-03-09 Warner-Lambert Company Compounds having antitumour and antibacterial properties

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ATWELL G.J. ET AL.: "Potential Antitumor Agents. 60. Relationships between Structure and in Vivo Colon 38 Activity for 5-Substituted 9-Oxoxanthene-4-acetic Acids", JOURNAL OF MEDICINAL CHEMISTRY, vol. 33, 1990, pages 1375 - 1379, XP001152568, DOI: doi:10.1021/jm00167a015 *
FUTAMI H. ET AL.: "Cytokine Induction and Therapeutic Synergy with Interleukin-2 Against Murine Renal and Colon Cancers by Xanthenone-4-Acetic Acid Derivatives", JOURNAL OF IMMUNOTHERAPY, vol. 12, no. 4, 1992, pages 247 - 255, XP002964496 *
REWCASTLE G.W. ET AL.: "Potential Antitumor Agents. 58. Synthesis and Structure-Activity Relationships of Substituted Xanthenone-4-acetic Acids Active against the Colon 38 Tumor in Vivo", JOURNAL OF MEDICINAL CHEMISTRY, vol. 32, 1989, pages 793 - 799 *
REWCASTLE G.W. ET AL.: "Potential Antitumor Agents. 61. Structure-Activity Relationships for in Vivo Colon 38 Activity among Disubstituted 9-Oxo-9-H-xanthene-4-acetic Acids", JOURNAL OF MEDICINAL CHEMISTRY, vol. 34, 1991, pages 217 - 222, XP008123695, DOI: doi:10.1021/jm00105a034 *

Also Published As

Publication number Publication date
WO2008048117A2 (en) 2008-04-24

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