WO1998005669A1 - Total synthesis of antitumor acylfulvenes - Google Patents

Total synthesis of antitumor acylfulvenes Download PDF

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Publication number
WO1998005669A1
WO1998005669A1 PCT/US1997/013644 US9713644W WO9805669A1 WO 1998005669 A1 WO1998005669 A1 WO 1998005669A1 US 9713644 W US9713644 W US 9713644W WO 9805669 A1 WO9805669 A1 WO 9805669A1
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WO
WIPO (PCT)
Prior art keywords
formula
compound
yield
steps
group
Prior art date
Application number
PCT/US1997/013644
Other languages
English (en)
French (fr)
Inventor
Trevor C. Mcmorris
Original Assignee
The Regents Of The University Of California
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 The Regents Of The University Of California filed Critical The Regents Of The University Of California
Priority to AT97934366T priority Critical patent/ATE263771T1/de
Priority to DE69728544T priority patent/DE69728544T2/de
Priority to CA002262648A priority patent/CA2262648A1/en
Priority to AU37443/97A priority patent/AU3744397A/en
Priority to US09/242,091 priority patent/US6160184A/en
Priority to EP97934366A priority patent/EP0918776B1/en
Priority to JP50812898A priority patent/JP4267702B2/ja
Publication of WO1998005669A1 publication Critical patent/WO1998005669A1/en
Priority to HK99105109A priority patent/HK1019878A1/xx

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
    • 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
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
    • C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
    • C07C49/737—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system having three rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/94—Spiro compounds containing "free" spiro atoms
    • 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
    • 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
    • Y02P20/582—Recycling of unreacted starting or intermediate materials
PCT/US1997/013644 1996-08-08 1997-08-05 Total synthesis of antitumor acylfulvenes WO1998005669A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
AT97934366T ATE263771T1 (de) 1996-08-08 1997-08-05 Totalsynthese von acylfulvenen mit antitumorwirkung
DE69728544T DE69728544T2 (de) 1996-08-08 1997-08-05 Totalsynthese von acylfulvenen mit antitumorwirkung
CA002262648A CA2262648A1 (en) 1996-08-08 1997-08-05 Total synthesis of antitumor acylfulvenes
AU37443/97A AU3744397A (en) 1996-08-08 1997-08-05 Total synthesis of antitumor acylfulvenes
US09/242,091 US6160184A (en) 1996-08-08 1997-08-05 Total synthesis of antitumor acylfulvenes
EP97934366A EP0918776B1 (en) 1996-08-08 1997-08-05 Total synthesis of antitumor acylfulvenes
JP50812898A JP4267702B2 (ja) 1996-08-08 1997-08-05 抗腫瘍アシルフルベンの全合成
HK99105109A HK1019878A1 (en) 1996-08-08 1999-11-08 Total synthesis of antitumor acylfulvenes.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/689,461 1996-08-08
US08/689,461 US5723632A (en) 1996-08-08 1996-08-08 Total synthesis of antitumor acylfulvenes

Related Parent Applications (2)

Application Number Title Priority Date Filing Date
US08/689,461 Continuation-In-Part US5723632A (en) 1996-08-08 1996-08-08 Total synthesis of antitumor acylfulvenes
US08/689,461 Continuation US5723632A (en) 1996-08-08 1996-08-08 Total synthesis of antitumor acylfulvenes

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US09/242,091 A-371-Of-International US6160184A (en) 1996-08-08 1997-08-05 Total synthesis of antitumor acylfulvenes
US09/679,831 Division US6252093B1 (en) 1996-08-08 2000-10-05 Total synthesis of antitumor acylfulvenes

Publications (1)

Publication Number Publication Date
WO1998005669A1 true WO1998005669A1 (en) 1998-02-12

Family

ID=24768581

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1997/013644 WO1998005669A1 (en) 1996-08-08 1997-08-05 Total synthesis of antitumor acylfulvenes

Country Status (12)

Country Link
US (6) US5723632A (US06252093-20010626-C00021.png)
EP (2) EP0918776B1 (US06252093-20010626-C00021.png)
JP (1) JP4267702B2 (US06252093-20010626-C00021.png)
AT (1) ATE263771T1 (US06252093-20010626-C00021.png)
AU (1) AU3744397A (US06252093-20010626-C00021.png)
CA (1) CA2262648A1 (US06252093-20010626-C00021.png)
DE (1) DE69728544T2 (US06252093-20010626-C00021.png)
DK (1) DK0918776T3 (US06252093-20010626-C00021.png)
ES (1) ES2215234T3 (US06252093-20010626-C00021.png)
HK (1) HK1019878A1 (US06252093-20010626-C00021.png)
PT (1) PT918776E (US06252093-20010626-C00021.png)
WO (1) WO1998005669A1 (US06252093-20010626-C00021.png)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002503714A (ja) * 1998-02-20 2002-02-05 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア 抗腫瘍剤
WO2008044045A1 (en) 2006-10-12 2008-04-17 Astex Therapeutics Limited Pharmaceutical combinations
WO2008044041A1 (en) 2006-10-12 2008-04-17 Astex Therapeutics Limited Pharmaceutical combinations
US7655695B2 (en) 2005-08-03 2010-02-02 The Regents Of The University Of California Illudin analogs useful as anticancer agents
US7713939B2 (en) 1996-07-18 2010-05-11 The Regents Of The University Of California Illudin analogs useful as antitumor agents

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US5723632A (en) * 1996-08-08 1998-03-03 Mgi Pharma, Inc. Total synthesis of antitumor acylfulvenes
US7141603B2 (en) * 1999-02-19 2006-11-28 The Regents Of The University California Antitumor agents
US6635490B1 (en) * 2000-05-25 2003-10-21 Noble Laboratories Procedure for the simultaneous quantitative and qualitative analysis of both flavonoid glycosides and steroidal glycosides
EP1330459B1 (en) * 2000-10-02 2006-08-02 Emory University Triptolide analogs for the treatment of autoimmune and inflammatory disorders
US7015247B2 (en) * 2000-10-12 2006-03-21 Alvin Guttag Ibuprofen-aspirin, hydroxymethylacylfulvene analogs and L-sugar illudin analogs
US6436916B1 (en) 2000-10-12 2002-08-20 Alvin Guttag Ibuprofen-aspirin and hydroxymethylacylfulvene analogs
ATE487744T1 (de) * 2001-06-22 2010-11-15 Borealis Tech Oy Metallocenkatalysatoren mit einer in 4-, 5-, 6- oder 7-stellung mit siloxy oder germyloxy substitutierten indenylgruppe
US7718385B2 (en) * 2003-10-17 2010-05-18 The Johns Hopkins University Bioactivation of alkylating agents for cancer treatment
CA2685726A1 (en) * 2007-05-03 2008-11-13 Emory University Fulvene and fulvalene analogs and their use in treating cancers
GB0715576D0 (en) * 2007-08-09 2007-09-19 Syngenta Ltd Novel herbicides
WO2009089285A2 (en) * 2008-01-07 2009-07-16 Emory University Branched diepoxide compounds for the treatment of inflammatory disorders
US10285955B2 (en) 2014-04-10 2019-05-14 Af Chemicals, Llc Affinity medicant conjugate
US11135182B2 (en) 2014-04-10 2021-10-05 Af Chemicals, Llc Affinity medicant conjugates
JP2017518359A (ja) 2014-04-10 2017-07-06 エイエフ ケミカルス, エルエルシーAf Chemicals, Llc 親和性薬物コンジュゲート
CN104650160A (zh) * 2015-01-13 2015-05-27 济南大学 卡培他滨关键中间体1,2,3-o-三乙酰基-5-脱氧-d-核糖的合成新方法
BR112021006710A2 (pt) 2018-09-04 2021-08-10 Lantern Pharma Inc. composto análogos de iludina, usos dos mesmos e métodos para sintetizar os mesmos
EP3667323A1 (en) 2018-12-11 2020-06-17 Kelner, Michael Methods, compositions and devices for treating cancer with illudofulvenes
US11591295B2 (en) 2019-11-25 2023-02-28 Af Chemicals Llc Affinity illudofulvene conjugates

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WO1991004754A2 (en) * 1989-10-03 1991-04-18 The Regents Of The University Of California Illudin analogs as anti-tumor agents
US5439936A (en) * 1989-10-03 1995-08-08 The Regents Of The University Of California Method of treating certain tumors using illudin analogs

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US5723632A (en) * 1996-08-08 1998-03-03 Mgi Pharma, Inc. Total synthesis of antitumor acylfulvenes
US6025328A (en) 1998-02-20 2000-02-15 The Regents Of The University Of California Antitumor agents

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US5439936A (en) * 1989-10-03 1995-08-08 The Regents Of The University Of California Method of treating certain tumors using illudin analogs
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A. PADWA ET AL.: "Generation and Cycloaddition Behavior of Spirocyclic Carbonyl Ylides. Application to the Synthesis of the Pterosin Family of Sesquiterpenes", JOURNAL OF ORGANIC CHEMISTRY, vol. 61, no. 1, 1996, pages 73 - 81, XP002045801 *
A. PADWA ET AL.: "Synthetic Studies toward Illudins and Ptaquilosin. A Highly Convergent Approach via the Dipolar Cycloaddition of Carbonyl Ylides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 116, no. 6, 1994, pages 2667 - 8, XP002045802 *
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7713939B2 (en) 1996-07-18 2010-05-11 The Regents Of The University Of California Illudin analogs useful as antitumor agents
JP2002503714A (ja) * 1998-02-20 2002-02-05 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア 抗腫瘍剤
US7655695B2 (en) 2005-08-03 2010-02-02 The Regents Of The University Of California Illudin analogs useful as anticancer agents
WO2008044045A1 (en) 2006-10-12 2008-04-17 Astex Therapeutics Limited Pharmaceutical combinations
WO2008044041A1 (en) 2006-10-12 2008-04-17 Astex Therapeutics Limited Pharmaceutical combinations

Also Published As

Publication number Publication date
DE69728544T2 (de) 2004-09-16
US6717017B2 (en) 2004-04-06
US6469184B2 (en) 2002-10-22
US5856580A (en) 1999-01-05
US6252093B1 (en) 2001-06-26
ES2215234T3 (es) 2004-10-01
ATE263771T1 (de) 2004-04-15
US5723632A (en) 1998-03-03
CA2262648A1 (en) 1998-02-12
AU3744397A (en) 1998-02-25
EP1454890A2 (en) 2004-09-08
US20010029303A1 (en) 2001-10-11
EP0918776B1 (en) 2004-04-07
PT918776E (pt) 2004-07-30
HK1019878A1 (en) 2000-03-03
EP0918776A1 (en) 1999-06-02
US20030050495A1 (en) 2003-03-13
JP2000515552A (ja) 2000-11-21
DE69728544D1 (de) 2004-05-13
EP1454890A3 (en) 2004-11-10
JP4267702B2 (ja) 2009-05-27
US6160184A (en) 2000-12-12
EP1454890A8 (en) 2004-11-03
DK0918776T3 (da) 2004-07-12

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