WO1998007716A3 - Heteroarotinoids-anticancer agents with receptor specificity and Tgase activity - Google Patents

Heteroarotinoids-anticancer agents with receptor specificity and Tgase activity Download PDF

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Publication number
WO1998007716A3
WO1998007716A3 PCT/US1997/014720 US9714720W WO9807716A3 WO 1998007716 A3 WO1998007716 A3 WO 1998007716A3 US 9714720 W US9714720 W US 9714720W WO 9807716 A3 WO9807716 A3 WO 9807716A3
Authority
WO
WIPO (PCT)
Prior art keywords
heteroarotinoids
receptor specificity
anticancer agents
activity
tgase activity
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.)
Ceased
Application number
PCT/US1997/014720
Other languages
French (fr)
Other versions
WO1998007716A2 (en
Inventor
Kenneth Darrel Berlin
Shanker Subramanian
Eldon Carl Nelson
Matora May Madler
Manford Kenneth Patterson Jr
Paul Joseph Birckbichler
Doris Mangiaracina Benbrook
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.)
Oklahoma State University
Original Assignee
Oklahoma State University
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 Oklahoma State University filed Critical Oklahoma State University
Priority to AU40805/97A priority Critical patent/AU4080597A/en
Publication of WO1998007716A2 publication Critical patent/WO1998007716A2/en
Publication of WO1998007716A3 publication Critical patent/WO1998007716A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/20—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 hydrogenated in the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/76—Benzo[c]pyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Anticancer compositions having receptor specificity as well as activity in stimulating formation of the enzyme transglutaminase as a marker for anticancer activity. The compositions comprise certain heteroarotinoid structures partially related to trans-retinoic acid through the basic, fused-ring framework.
PCT/US1997/014720 1996-08-23 1997-08-21 Heteroarotinoids-anticancer agents with receptor specificity and tgase activity Ceased WO1998007716A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU40805/97A AU4080597A (en) 1996-08-23 1997-08-21 Heteroarotinoids-anticancer agents with receptor specificity and tgase activity

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2452196P 1996-08-23 1996-08-23
US60/024,521 1996-08-23

Publications (2)

Publication Number Publication Date
WO1998007716A2 WO1998007716A2 (en) 1998-02-26
WO1998007716A3 true WO1998007716A3 (en) 1998-03-26

Family

ID=21821021

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1997/014720 Ceased WO1998007716A2 (en) 1996-08-23 1997-08-21 Heteroarotinoids-anticancer agents with receptor specificity and tgase activity

Country Status (2)

Country Link
AU (1) AU4080597A (en)
WO (1) WO1998007716A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU4719799A (en) * 1998-06-30 2000-01-17 Du Pont Pharmaceuticals Company Substituted quinolin-2(1h)-ones useful as hiv reverse transcriptase inhibitors
WO2000015612A1 (en) * 1998-08-26 2000-03-23 Aventis Pharma Limited Aza-bicycles which modulate the inhibition of cell adhesion
GB9818641D0 (en) * 1998-08-26 1998-10-21 Rh Ne Poulenc Rorer Limited Chemical compounds
US6586460B1 (en) 2001-04-02 2003-07-01 The Board Of Regents For Oklahoma State University Heteroarotinoids containing urea or thiourea linker
CA2962150C (en) * 2014-10-10 2023-07-04 High Force Research Limited Fluorescent synthetic retinoids
US10238655B2 (en) * 2017-01-23 2019-03-26 Arizona Board Of Regents On Behalf Of Arizona State University Dihydroindene and tetrahydronaphthalene compounds
US10238626B2 (en) * 2017-01-23 2019-03-26 Arizona Board Of Regents On Behalf Of Arizona State University Therapeutic compounds
US10231947B2 (en) * 2017-01-23 2019-03-19 Arizona Board Of Regents On Behalf Of Arizona State University Isochroman compounds and methods of use thereof
WO2024137738A1 (en) * 2022-12-22 2024-06-27 The Board Of Regents Of The University Of Oklahoma Combinations of poly (adp-ribose) polymerase (parp) inhibitors and heteroarotinoids and methods of use as cancer treatments

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2390428A1 (en) * 1977-05-04 1978-12-08 Hoffmann La Roche NEW POLYENE COMPOUNDS, THEIR PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS
GB2119801A (en) * 1982-05-12 1983-11-23 Hoffmann La Roche Heterocyclic compounds
EP0130795A2 (en) * 1983-07-05 1985-01-09 Pfizer Inc. Carboxylic acid derivatives useful for inhibiting the degradation of cartilage
WO1985000806A1 (en) * 1983-08-08 1985-02-28 Sri International Benzonorbornenyl, benzopyranyl and benzothiopyranyl retinoic acid analogues
US4826984A (en) * 1984-04-09 1989-05-02 The Board Of Regents For The Oklahoma Agricultural And Mechanical College Acting For And On Behalf Of Oklahoma State University Heteroarotinoid compounds as anticancer agents
US4833254A (en) * 1987-05-11 1989-05-23 The Board Of Regents For The Oklahoma Agricultural And Mechanical Colleges Acting For And On Behalf Of Oklahoma State University Heteroarotinoids as anticancer agents
EP0350846A2 (en) * 1988-07-14 1990-01-17 F. Hoffmann-La Roche Ag Condensed heterocyclic compounds and their use in therapy
EP0405028A1 (en) * 1988-06-29 1991-01-02 Allergan, Inc Thiochroman esters of phenols and terephthalates having retinoid-like activity
US5006550A (en) * 1989-12-29 1991-04-09 Allergan, Inc. Chroman esters of phenols and benzoic acids having retinoid-like activity

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2390428A1 (en) * 1977-05-04 1978-12-08 Hoffmann La Roche NEW POLYENE COMPOUNDS, THEIR PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS
GB2119801A (en) * 1982-05-12 1983-11-23 Hoffmann La Roche Heterocyclic compounds
EP0130795A2 (en) * 1983-07-05 1985-01-09 Pfizer Inc. Carboxylic acid derivatives useful for inhibiting the degradation of cartilage
WO1985000806A1 (en) * 1983-08-08 1985-02-28 Sri International Benzonorbornenyl, benzopyranyl and benzothiopyranyl retinoic acid analogues
US4826984A (en) * 1984-04-09 1989-05-02 The Board Of Regents For The Oklahoma Agricultural And Mechanical College Acting For And On Behalf Of Oklahoma State University Heteroarotinoid compounds as anticancer agents
US4833254A (en) * 1987-05-11 1989-05-23 The Board Of Regents For The Oklahoma Agricultural And Mechanical Colleges Acting For And On Behalf Of Oklahoma State University Heteroarotinoids as anticancer agents
EP0405028A1 (en) * 1988-06-29 1991-01-02 Allergan, Inc Thiochroman esters of phenols and terephthalates having retinoid-like activity
EP0350846A2 (en) * 1988-07-14 1990-01-17 F. Hoffmann-La Roche Ag Condensed heterocyclic compounds and their use in therapy
US5006550A (en) * 1989-12-29 1991-04-09 Allergan, Inc. Chroman esters of phenols and benzoic acids having retinoid-like activity

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HIROYUKI KAGECHIKA ET AL.: "RETINOBENZOIC ACIDS.1.", JOURNAL OF MEDICINAL CHEMISTRY., vol. 31, November 1988 (1988-11-01), WASHINGTON US, pages 2182 - 2192, XP000608417 *

Also Published As

Publication number Publication date
WO1998007716A2 (en) 1998-02-26
AU4080597A (en) 1998-03-06

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