WO2000000469A3 - Alkyl ketones as potent anti-cancer agents - Google Patents

Alkyl ketones as potent anti-cancer agents Download PDF

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Publication number
WO2000000469A3
WO2000000469A3 PCT/US1999/014758 US9914758W WO0000469A3 WO 2000000469 A3 WO2000000469 A3 WO 2000000469A3 US 9914758 W US9914758 W US 9914758W WO 0000469 A3 WO0000469 A3 WO 0000469A3
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WO
WIPO (PCT)
Prior art keywords
cancer agents
potent anti
alkyl ketones
compounds
formula
Prior art date
Application number
PCT/US1999/014758
Other languages
French (fr)
Other versions
WO2000000469A2 (en
Inventor
Fatih M Uckun
Rama K Narla
David A Perry
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Wayne Hughes Inst
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 Wayne Hughes Inst filed Critical Wayne Hughes Inst
Priority to AU48459/99A priority Critical patent/AU754086B2/en
Priority to EP99932068A priority patent/EP1091934A2/en
Priority to CA002336108A priority patent/CA2336108A1/en
Priority to JP2000557230A priority patent/JP2002519341A/en
Publication of WO2000000469A2 publication Critical patent/WO2000000469A2/en
Publication of WO2000000469A3 publication Critical patent/WO2000000469A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
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    • C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
    • C07C233/31—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
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    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
    • C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07C271/18—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 carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
    • 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
    • C07C271/22—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 carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
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    • C07—ORGANIC CHEMISTRY
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    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
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    • C07C2603/00—Systems containing at least three condensed rings
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Abstract

Novel alkyl ketone compounds having potent cytotoxic activity are described as antitumor agents and are particularly effective against leukemia and breast tumor cells. The compounds of the invention have formula (I), wherein R1-R4, X and p have the meanings given in the description.
PCT/US1999/014758 1998-06-29 1999-06-29 Alkyl ketones as potent anti-cancer agents WO2000000469A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU48459/99A AU754086B2 (en) 1998-06-29 1999-06-29 Alkyl ketones as potent anti-cancer agents
EP99932068A EP1091934A2 (en) 1998-06-29 1999-06-29 Alkyl ketones as potent anti-cancer agents
CA002336108A CA2336108A1 (en) 1998-06-29 1999-06-29 Alkyl ketones as potent anti-cancer agents
JP2000557230A JP2002519341A (en) 1998-06-29 1999-06-29 Alkyl ketones as potent anticancer agents

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US9099798P 1998-06-29 1998-06-29
US9736398P 1998-08-21 1998-08-21
US60/090,997 1998-08-21
US60/097,363 1998-08-21

Publications (2)

Publication Number Publication Date
WO2000000469A2 WO2000000469A2 (en) 2000-01-06
WO2000000469A3 true WO2000000469A3 (en) 2000-06-15

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PCT/US1999/014758 WO2000000469A2 (en) 1998-06-29 1999-06-29 Alkyl ketones as potent anti-cancer agents

Country Status (5)

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EP (1) EP1091934A2 (en)
JP (1) JP2002519341A (en)
AU (1) AU754086B2 (en)
CA (1) CA2336108A1 (en)
WO (1) WO2000000469A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002534355A (en) * 1998-06-29 2002-10-15 パーカー ヒューズ インスティテュート Tubulin binding compound (COBRA)
US6258841B1 (en) 1998-06-29 2001-07-10 Parker Hughes Institute Tubulin binding compounds (COBRA)
NO328803B1 (en) * 2000-03-03 2010-05-18 Thia Medica New fatty acid analogues
US6734207B2 (en) 2001-04-20 2004-05-11 Parker Hughes Institute Cytotoxic compounds
AU2003247390A1 (en) 2002-05-22 2003-12-12 Errant Gene Therapeutics, Llc. Histone deacetylase inhibitors based on alphachalcogenmethylcarbonyl compounds
CA2780624A1 (en) 2008-11-11 2010-05-20 Signum Biosciences, Inc. Isoprenyl derivatives useful as agents to modulate inflammation
EP3674297A1 (en) 2013-11-08 2020-07-01 Promentis Pharmaceuticals, Inc. Substituted n-acetyl-l-cysteine derivatives and related compounds

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992018465A1 (en) * 1991-04-15 1992-10-29 Harvard College Compounds for inhibition of protein methylation
JPH05117169A (en) * 1991-10-29 1993-05-14 Mitsubishi Kasei Corp Method for producing chloromethyl ketone
WO1995017512A2 (en) * 1993-12-23 1995-06-29 Cangene Corporation Proteases from streptomyces and use thereof in protein expression systems
WO1998022098A2 (en) * 1996-11-20 1998-05-28 Qlt Phototherapeutics, Inc. Cpp32 inhibitors for regulating apoptosis

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992018465A1 (en) * 1991-04-15 1992-10-29 Harvard College Compounds for inhibition of protein methylation
JPH05117169A (en) * 1991-10-29 1993-05-14 Mitsubishi Kasei Corp Method for producing chloromethyl ketone
WO1995017512A2 (en) * 1993-12-23 1995-06-29 Cangene Corporation Proteases from streptomyces and use thereof in protein expression systems
WO1998022098A2 (en) * 1996-11-20 1998-05-28 Qlt Phototherapeutics, Inc. Cpp32 inhibitors for regulating apoptosis

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
CHEN, PING ET AL.: "A Practical Method for the Preparation of alpha'-Chloroketones of N-Carbamate Protected alpha-Aminoacids", TETRAHEDRON LETTERS, vol. 38, no. 18, 1997, pages 3175 - 3178, XP002120874 *
CHEN, YULONG ET AL.: "Solubilization, Partial Purification, and Affinity Labeling of the Membrane-Bound Isoprenylated Protein Endoprotease", BIOCHEMISTRY, vol. 35, no. 10, 1996, pages 3227 - 3237, XP002120873 *
DATABASE CHEMICAL ABSTRACTS ACS; 17 December 1990 (1990-12-17), INAZU, TOSHIYUKI & YAMANOI, TAKASHI: "Synthetic studies on D-erythro-C18-sphingosine", XP002120876 *
DATABASE CHEMICAL ABSTRACTS ACS; 22 November 1993 (1993-11-22), ANDO, RYOICHI: "Preparation of chloromethyl ketones as inhibitors for serine and thiol protease", XP002120875 *
JIA, ZONGCHAO ET AL.: "Crystal Structures of Recombinant Rat Cathepsin B and a Cathepsin B-Inhibitor Complex", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 270, no. 10, 10 March 1995 (1995-03-10), pages 5527 - 5533, XP002120872 *
NOGUSHI KENKYUSHO JIHO, no. 32, 1989, pages 13 - 26 *

Also Published As

Publication number Publication date
AU4845999A (en) 2000-01-17
WO2000000469A2 (en) 2000-01-06
CA2336108A1 (en) 2000-01-06
JP2002519341A (en) 2002-07-02
AU754086B2 (en) 2002-11-07
EP1091934A2 (en) 2001-04-18

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