CA2530543A1 - Illudin analogs as anti-tumor agents - Google Patents

Illudin analogs as anti-tumor agents Download PDF

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Publication number
CA2530543A1
CA2530543A1 CA002530543A CA2530543A CA2530543A1 CA 2530543 A1 CA2530543 A1 CA 2530543A1 CA 002530543 A CA002530543 A CA 002530543A CA 2530543 A CA2530543 A CA 2530543A CA 2530543 A1 CA2530543 A1 CA 2530543A1
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CA
Canada
Prior art keywords
tumor agents
illudin analogs
illudin
analogs
methyl
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.)
Granted
Application number
CA002530543A
Other languages
French (fr)
Other versions
CA2530543C (en
Inventor
Michael J. Kelner
Trevor C. Mcmorris
Raymond Taetle
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.)
University of California
Original Assignee
The Regents Of The University Of California
Michael J. Kelner
Trevor C. Mcmorris
Raymond Taetle
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, Michael J. Kelner, Trevor C. Mcmorris, Raymond Taetle filed Critical The Regents Of The University Of California
Publication of CA2530543A1 publication Critical patent/CA2530543A1/en
Application granted granted Critical
Publication of CA2530543C publication Critical patent/CA2530543C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • 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
    • A61K31/12—Ketones
    • 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
    • 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
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • 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
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • 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
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • 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
    • C07C45/65—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 by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • 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
    • C07C45/67—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 by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—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 by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • 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
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
    • C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
    • 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
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic 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
    • 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
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic 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
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • 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

Abstract

A compound having the structure wherein R = methyl or hydroxyl; and R1, R2 and R3 = methyl or alkyl.

A compound having the structure
CA002530543A 1989-10-03 1990-10-02 Illudin analogs as anti-tumor agents Expired - Lifetime CA2530543C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US41639589A 1989-10-03 1989-10-03
US416,395 1989-10-03
CA002067365A CA2067365C (en) 1989-10-03 1990-10-02 Illudin analogs as anti-tumor agents

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA002067365A Division CA2067365C (en) 1989-10-03 1990-10-02 Illudin analogs as anti-tumor agents

Publications (2)

Publication Number Publication Date
CA2530543A1 true CA2530543A1 (en) 1991-04-18
CA2530543C CA2530543C (en) 2008-04-01

Family

ID=23649800

Family Applications (2)

Application Number Title Priority Date Filing Date
CA002067365A Expired - Lifetime CA2067365C (en) 1989-10-03 1990-10-02 Illudin analogs as anti-tumor agents
CA002530543A Expired - Lifetime CA2530543C (en) 1989-10-03 1990-10-02 Illudin analogs as anti-tumor agents

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CA002067365A Expired - Lifetime CA2067365C (en) 1989-10-03 1990-10-02 Illudin analogs as anti-tumor agents

Country Status (11)

Country Link
US (1) US5439942A (en)
EP (1) EP0565519B1 (en)
JP (1) JPH05503077A (en)
AT (1) ATE141802T1 (en)
AU (1) AU6729590A (en)
CA (2) CA2067365C (en)
DE (1) DE69028320T2 (en)
DK (1) DK0565519T3 (en)
ES (1) ES2091249T3 (en)
IL (1) IL95875A (en)
WO (1) WO1991004754A2 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5439936A (en) * 1989-10-03 1995-08-08 The Regents Of The University Of California Method of treating certain tumors using illudin analogs
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
US7655695B2 (en) 2005-08-03 2010-02-02 The Regents Of The University Of California Illudin analogs useful as anticancer agents
US20080065083A1 (en) * 2006-09-07 2008-03-13 Csaba Truckai Bone treatment systems and methods
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
CA2944699C (en) 2014-04-10 2023-05-23 Af Chemicals, Llc Affinity medicant conjugates
CN106083953A (en) * 2016-06-15 2016-11-09 成都医学院 A kind of from fiddlehead, extract former pteroside and the method preparing high purity raw pteroside
JP2021536492A (en) * 2018-09-04 2021-12-27 ランタン ファーマ インコーポレイテッド Illudin analogs, their use, and how to synthesize them
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 (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62234040A (en) * 1986-04-02 1987-10-14 Kyowa Hakko Kogyo Co Ltd Substance dc1043 and production thereof

Also Published As

Publication number Publication date
CA2530543C (en) 2008-04-01
ATE141802T1 (en) 1996-09-15
US5439942A (en) 1995-08-08
IL95875A (en) 1994-10-21
JPH05503077A (en) 1993-05-27
CA2067365A1 (en) 1991-04-04
DK0565519T3 (en) 1996-09-23
ES2091249T3 (en) 1996-11-01
WO1991004754A3 (en) 1991-12-12
CA2067365C (en) 2006-01-31
EP0565519B1 (en) 1996-08-28
DE69028320T2 (en) 1997-03-06
AU6729590A (en) 1991-04-28
DE69028320D1 (en) 1996-10-02
IL95875A0 (en) 1991-07-18
EP0565519A1 (en) 1993-10-20
WO1991004754A2 (en) 1991-04-18

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