JP4267702B2 - 抗腫瘍アシルフルベンの全合成 - Google Patents

抗腫瘍アシルフルベンの全合成 Download PDF

Info

Publication number
JP4267702B2
JP4267702B2 JP50812898A JP50812898A JP4267702B2 JP 4267702 B2 JP4267702 B2 JP 4267702B2 JP 50812898 A JP50812898 A JP 50812898A JP 50812898 A JP50812898 A JP 50812898A JP 4267702 B2 JP4267702 B2 JP 4267702B2
Authority
JP
Japan
Prior art keywords
compound
formula
alkyl
group
solution
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
JP50812898A
Other languages
English (en)
Japanese (ja)
Other versions
JP2000515552A (ja
Inventor
シー． マクモーリス，トレバー
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.)
THE REGENTS OF THE UNIVERSITY OF CARIFORNIA
Original Assignee
THE REGENTS OF THE UNIVERSITY OF CARIFORNIA
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 CARIFORNIA filed Critical THE REGENTS OF THE UNIVERSITY OF CARIFORNIA
Publication of JP2000515552A publication Critical patent/JP2000515552A/ja
Application granted granted Critical
Publication of JP4267702B2 publication Critical patent/JP4267702B2/ja
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Images

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
JP50812898A 1996-08-08 1997-08-05 抗腫瘍アシルフルベンの全合成 Expired - Fee Related JP4267702B2 (ja)

Applications Claiming Priority (3)

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
PCT/US1997/013644 WO1998005669A1 (en) 1996-08-08 1997-08-05 Total synthesis of antitumor acylfulvenes

Publications (2)

Publication Number Publication Date
JP2000515552A JP2000515552A (ja) 2000-11-21
JP4267702B2 true JP4267702B2 (ja) 2009-05-27

Family

ID=24768581

Family Applications (1)

Application Number Title Priority Date Filing Date
JP50812898A Expired - Fee Related JP4267702B2 (ja) 1996-08-08 1997-08-05 抗腫瘍アシルフルベンの全合成

Country Status (12)

Country Link
US (6) US5723632A (US06252093-20010626-C00030.png)
EP (2) EP0918776B1 (US06252093-20010626-C00030.png)
JP (1) JP4267702B2 (US06252093-20010626-C00030.png)
AT (1) ATE263771T1 (US06252093-20010626-C00030.png)
AU (1) AU3744397A (US06252093-20010626-C00030.png)
CA (1) CA2262648A1 (US06252093-20010626-C00030.png)
DE (1) DE69728544T2 (US06252093-20010626-C00030.png)
DK (1) DK0918776T3 (US06252093-20010626-C00030.png)
ES (1) ES2215234T3 (US06252093-20010626-C00030.png)
HK (1) HK1019878A1 (US06252093-20010626-C00030.png)
PT (1) PT918776E (US06252093-20010626-C00030.png)
WO (1) WO1998005669A1 (US06252093-20010626-C00030.png)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5932553A (en) * 1996-07-18 1999-08-03 The Regents Of The University Of California Illudin analogs useful as antitumor agents
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
US6025328A (en) * 1998-02-20 2000-02-15 The Regents Of The University Of 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
ATE469907T1 (de) * 2000-10-02 2010-06-15 Univ Emory Triptolid-analoga zur behandlung von autoimmunkranheiten und entzündungen
US6436916B1 (en) 2000-10-12 2002-08-20 Alvin Guttag Ibuprofen-aspirin and hydroxymethylacylfulvene analogs
US7015247B2 (en) * 2000-10-12 2006-03-21 Alvin Guttag Ibuprofen-aspirin, hydroxymethylacylfulvene analogs and L-sugar illudin analogs
DE60238256D1 (de) * 2001-06-22 2010-12-23 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
WO2007019308A2 (en) * 2005-08-03 2007-02-15 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
US8916552B2 (en) 2006-10-12 2014-12-23 Astex Therapeutics Limited Pharmaceutical combinations
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
US11135182B2 (en) 2014-04-10 2021-10-05 Af Chemicals, Llc Affinity medicant conjugates
US10285955B2 (en) 2014-04-10 2019-05-14 Af Chemicals, Llc Affinity medicant conjugate
CN106458922A (zh) 2014-04-10 2017-02-22 Af化学药品有限责任公司 亲和药物共轭物
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
EP3846791A4 (en) * 2018-09-04 2022-06-08 Lantern Pharma Inc. ILLUDIN ANALOGUES, THEIR USES AND PROCEDURES FOR THEIR SYNTHESIS
US11160807B1 (en) 2018-12-11 2021-11-02 Af Chemicals, Llc Methods, compositions and devices for treating cancer with illudofulvenes
US11591295B2 (en) 2019-11-25 2023-02-28 Af Chemicals Llc Affinity illudofulvene conjugates

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4559157A (en) * 1983-04-21 1985-12-17 Creative Products Resource Associates, Ltd. Cosmetic applicator useful for skin moisturizing
LU84979A1 (fr) * 1983-08-30 1985-04-24 Oreal Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux
US4612302A (en) * 1983-11-14 1986-09-16 Brigham And Women's Hospital Clinical use of somatostatin analogues
US4684620A (en) * 1984-09-04 1987-08-04 Gibson-Stephens Neuropharmaceuticals, Inc. Cyclic polypeptides having mu-receptor specificity
JPS62234040A (ja) * 1986-04-02 1987-10-14 Kyowa Hakko Kogyo Co Ltd Ｄｃ１０４３物質
US4853371A (en) * 1986-06-17 1989-08-01 The Administrators Of The Tulane Educational Fund Therapeutic somatostatin analogs
US4820508A (en) * 1987-06-23 1989-04-11 Neutrogena Corporation Skin protective composition
US4992478A (en) * 1988-04-04 1991-02-12 Warner-Lambert Company Antiinflammatory skin moisturizing composition and method of preparing same
US4938949A (en) * 1988-09-12 1990-07-03 University Of New York Treatment of damaged bone marrow and dosage units therefor
US5439936A (en) * 1989-10-03 1995-08-08 The Regents Of The University Of California Method of treating certain tumors using illudin analogs
DE69028320T2 (de) * 1989-10-03 1997-03-06 Univ California Illudin-analoge, verwendet als antitumormittel
GB9017024D0 (en) * 1990-08-03 1990-09-19 Erba Carlo Spa New linker for bioactive agents
SI9400195B (sl) * 1993-04-27 2003-10-31 Smithkline Beecham Corporation Antagonisti endotelinskih receptorjev
US5708163A (en) * 1994-03-15 1998-01-13 Sloan-Kettering Institute Of Cancer Research Synthesis of the breast tumor-associated antigen defined by monoclonalantibody MBRL and uses thereof
US6303120B1 (en) * 1994-03-15 2001-10-16 Memorial Sloan-Kettering Institute For Cancer Research Synthesis of glycoconjugates of the lewis y epitope and uses thereof
US5932553A (en) * 1996-07-18 1999-08-03 The Regents Of The University Of California Illudin analogs useful as antitumor agents
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

Also Published As

Publication number Publication date
HK1019878A1 (en) 2000-03-03
US6717017B2 (en) 2004-04-06
EP0918776A1 (en) 1999-06-02
US20030050495A1 (en) 2003-03-13
EP1454890A2 (en) 2004-09-08
AU3744397A (en) 1998-02-25
ATE263771T1 (de) 2004-04-15
US5856580A (en) 1999-01-05
CA2262648A1 (en) 1998-02-12
ES2215234T3 (es) 2004-10-01
DE69728544T2 (de) 2004-09-16
US20010029303A1 (en) 2001-10-11
WO1998005669A1 (en) 1998-02-12
EP1454890A3 (en) 2004-11-10
US5723632A (en) 1998-03-03
PT918776E (pt) 2004-07-30
JP2000515552A (ja) 2000-11-21
EP0918776B1 (en) 2004-04-07
US6252093B1 (en) 2001-06-26
DE69728544D1 (de) 2004-05-13
EP1454890A8 (en) 2004-11-03
US6160184A (en) 2000-12-12
US6469184B2 (en) 2002-10-22
DK0918776T3 (da) 2004-07-12

Similar Documents

Publication Publication Date Title
JP4267702B2 (ja) 抗腫瘍アシルフルベンの全合成
JPH0257548B2 (US06252093-20010626-C00030.png)
JP4372843B2 (ja) 坑腫瘍剤として有用なイルジン類似体
JP2699765B2 (ja) 含フッ素ビタミンｄ３類縁体およびこれらを有効成分とする医薬組成物
US11168064B2 (en) Synthesis of thapsigargin, nortrilobolide, and analogs thereof
CH638483A5 (de) 2,2-difluor-6a-carba-pgi2-verbindungen.
Ando et al. Studies on the Synthesis of Sesquiterpene Lactones, 16. The Syntheses of 11β, 13-Dihydrokauniolide, Estafiatin, Isodehydrocostuslactone, 2-Oxodesoxyligustrin, Arborescin, 1, 10-Epiarborescin, 11β, 13-Dihydroludartin, 8-Deoxy-11β, 13-dihydrorupicolin B, 8-Deoxyrupicolin B, 3, 4-Epiludartin, Ludartin, Kauniolide, Dehydroleucodin, and Leucodin
Demuth et al. Photocycloadditions of 2‐(trimethylsilyloxy)‐1, 3‐butadiene to 2‐cycloalkenones. Access to the basic pentalenolactone skeleton
Arai et al. An enantioconvergent route to carbocyclic nucleosides (–)-aristeromycin and (–)-neplanocin a via the asymmetric Diels–Alder reaction
EP0180399B1 (en) Anti-tumor 4-hydroxy-2-cyclopentenones
WO2014094511A1 (zh) 一种制备曲前列尼尔的中间体、其制备方法以及通过其制备曲前列尼尔的方法
JPS6296438A (ja) ４―ヒドロキシ―２―シクロペンテノン類及び薬剤組成物
WO1996034862A1 (en) Total synthesis of taxol and analogues thereof
RU2317992C2 (ru) Новые промежуточные соединения для синтеза производных витамина d
US4239689A (en) Total synthesis of the utero-evacuant substance d,l-zoapatanol
JPH10251183A (ja) ビタミンｄ誘導体のａ環部分の合成に有用な合成中間体、その製造方法およびその使用方法
Aav Synthesis of 9, 11-secosterols intermediates
JP3883263B2 (ja) マクロカルパル類の不斉合成方法
Kim et al. A novel synthetic route to 11-deoxyanthracycline AB synthons
US5113014A (en) Processes for preparing prostaglandins
Michelet et al. Synthesis of natural products and biologically active compounds via allylpalladium and related derivatives
WO1988003526A1 (en) New process for manufacturing optically active carbocycline intermediates
PT97483A (pt) Processo para a preparacao de biciclo{7.3.1}tridec-4-eno-2,6-diinos com actividade citotoxica e de composicoes farmaceuticas que os contem
JPH04305548A (ja) ハロゲノアリルアルコール誘導体
JPH01268684A (ja) アセチレン性、トリイン環状カーボネート

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20040609

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20080122

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20080421

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20080602

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20080709

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20080826

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20081125

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20090120

A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20090219

R150 Certificate of patent or registration of utility model

Free format text: JAPANESE INTERMEDIATE CODE: R150

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20120227

Year of fee payment: 3

LAPS Cancellation because of no payment of annual fees