CA2067365A1 - Illudin analogs as anti-tumor agents - Google Patents
Illudin analogs as anti-tumor agentsInfo
- Publication number
- CA2067365A1 CA2067365A1 CA002067365A CA2067365A CA2067365A1 CA 2067365 A1 CA2067365 A1 CA 2067365A1 CA 002067365 A CA002067365 A CA 002067365A CA 2067365 A CA2067365 A CA 2067365A CA 2067365 A1 CA2067365 A1 CA 2067365A1
- Authority
- CA
- Canada
- Prior art keywords
- illudin
- tumor agents
- illudin analogs
- analogs
- analog
- 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
Links
Classifications
-
- 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 method of inhibiting tumor cell growth in a subject is provided comprising contacting the tumor with a therapeutic amount of an illudin S or illudin M analog having structure (I) or (II), wherein the analog is capable of inhibiting tumor cell growth without excessive toxicity to the subject and wherein R1 is an alkyl or hydrogen; R2 is an alkyl; and R3 is an alcohol or ester.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002530543A CA2530543C (en) | 1989-10-03 | 1990-10-02 | Illudin analogs as anti-tumor agents |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US41639589A | 1989-10-03 | 1989-10-03 | |
US416,395 | 1989-10-03 | ||
PCT/US1990/005614 WO1991004754A2 (en) | 1989-10-03 | 1990-10-02 | Illudin analogs as anti-tumor agents |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002530543A Division CA2530543C (en) | 1989-10-03 | 1990-10-02 | Illudin analogs as anti-tumor agents |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2067365A1 true CA2067365A1 (en) | 1991-04-04 |
CA2067365C CA2067365C (en) | 2006-01-31 |
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 After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002530543A Expired - Lifetime CA2530543C (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)
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 |
EP1909783B1 (en) | 2005-08-03 | 2011-10-12 | 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 |
CA3194672A1 (en) | 2014-04-10 | 2015-10-15 | Af Chemicals, Llc | Affinity medicant conjugates |
US10285955B2 (en) | 2014-04-10 | 2019-05-14 | Af Chemicals, Llc | Affinity medicant conjugate |
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 |
WO2020051222A1 (en) * | 2018-09-04 | 2020-03-12 | Lantern Pharma Inc. | Illudin analogs, uses thereof, and methods for synthesizing the same |
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)
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 |
-
1990
- 1990-10-02 ES ES90916968T patent/ES2091249T3/en not_active Expired - Lifetime
- 1990-10-02 CA CA002067365A patent/CA2067365C/en not_active Expired - Lifetime
- 1990-10-02 WO PCT/US1990/005614 patent/WO1991004754A2/en active IP Right Grant
- 1990-10-02 AU AU67295/90A patent/AU6729590A/en not_active Abandoned
- 1990-10-02 JP JP2515522A patent/JPH05503077A/en active Pending
- 1990-10-02 AT AT90916968T patent/ATE141802T1/en not_active IP Right Cessation
- 1990-10-02 DK DK90916968.2T patent/DK0565519T3/en active
- 1990-10-02 IL IL9587590A patent/IL95875A/en not_active IP Right Cessation
- 1990-10-02 DE DE69028320T patent/DE69028320T2/en not_active Expired - Lifetime
- 1990-10-02 CA CA002530543A patent/CA2530543C/en not_active Expired - Lifetime
- 1990-10-02 EP EP90916968A patent/EP0565519B1/en not_active Expired - Lifetime
- 1990-10-31 US US07/606,511 patent/US5439942A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CA2067365C (en) | 2006-01-31 |
EP0565519B1 (en) | 1996-08-28 |
WO1991004754A3 (en) | 1991-12-12 |
DE69028320T2 (en) | 1997-03-06 |
IL95875A0 (en) | 1991-07-18 |
WO1991004754A2 (en) | 1991-04-18 |
JPH05503077A (en) | 1993-05-27 |
IL95875A (en) | 1994-10-21 |
CA2530543A1 (en) | 1991-04-18 |
DK0565519T3 (en) | 1996-09-23 |
AU6729590A (en) | 1991-04-28 |
ES2091249T3 (en) | 1996-11-01 |
EP0565519A1 (en) | 1993-10-20 |
US5439942A (en) | 1995-08-08 |
ATE141802T1 (en) | 1996-09-15 |
CA2530543C (en) | 2008-04-01 |
DE69028320D1 (en) | 1996-10-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NZ331824A (en) | use of an unsaturated fatty alcohol to stabilise a macrolide in a pharmaceutical composition | |
CA2067365A1 (en) | Illudin analogs as anti-tumor agents | |
CA2088909A1 (en) | Enzymic alteration of hair growth | |
CA2155329A1 (en) | Acylfulvene analogues as antitumor agents | |
MY118354A (en) | 1,3-propane diol derivatives as bioactive compounds | |
AU7194691A (en) | Therapeutic use of indole-3-yl-carboxylic acid endo-8- methyl-8-aza-bicyclo(3,2,1)oct-3-yl ester | |
AU626749B2 (en) | Transparent cosmetic composition containing glycerol, soap, and soap crystal growth inhibitor | |
AU5448186A (en) | Cyclopental ``d``pyrimidine derivatives, their preparation and use | |
EP0202394A3 (en) | Pigment composition | |
EP0341707A3 (en) | Phenylethanol ester of ortho-cinnamic acid, its preparation and use as fragrance compound | |
CA2014771A1 (en) | 5,11-dihydro-6h-dipyrido[3,2-b:2'3'-e][1,4]diazepin-6-ones and their use in the prevention or treatment of aids | |
ES8706186A1 (en) | Polymerisable composition. | |
AU6452890A (en) | Trigylcerides containing saturated fatty acids having 20 to 24 carbon atoms useful in lowering blood cholesterol levels | |
CA2128103A1 (en) | Formulation and use of carotenoids in treatment of cancer | |
AU3678689A (en) | Treatment of conditions requiring enhanced oxygen availability to mammalian tissues | |
IL85403A (en) | O-(6-alkoxy-2-t-butyl-pyrimidin-4-yl)-o-methylthionophosphonic acid esters,their preparation and their use as pesticides | |
PL267370A1 (en) | The method of alcohol izoprophyl manufacture and of c-3 alcohols with 4 to 5 carbon atoms | |
IE802418L (en) | ANTIALLERGIC AND ANTIULCER 1-OXO-1H-THIAZOLO (3,2-a)¹PYRIMIDINE-2-CARBOXAMIDES | |
CA2098102A1 (en) | Alteration of rate and character of hair growth | |
GB2137204B (en) | Improvements in or relating to macrolideantibiotics | |
MY102247A (en) | Phosphorylated acylglycosides, their preparation and use | |
ES2004685A6 (en) | Hair cosmetic compsn. | |
ES2000306A6 (en) | Pheromone compsn. for Sparganothis pilleriana | |
EP0319050A3 (en) | Griseolic acid derivatives, their preparation and their use | |
AU99957S (en) | An article of clothing |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |