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WO2000053581A3 - Composes heterocycliques ayant une activite antitumorale - Google Patents

Composes heterocycliques ayant une activite antitumorale Download PDF

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Publication number
WO2000053581A3
WO2000053581A3 PCT/EP2000/001721 EP0001721W WO0053581A3 WO 2000053581 A3 WO2000053581 A3 WO 2000053581A3 EP 0001721 W EP0001721 W EP 0001721W WO 0053581 A3 WO0053581 A3 WO 0053581A3
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
coorc
heterocyclic compounds
antitumor activity
nrarb
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/EP2000/001721
Other languages
English (en)
Other versions
WO2000053581A2 (fr
Inventor
Ernesto Menta
Marco Conti
Nicoletta Pescalli
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.)
Novuspharma SpA
Original Assignee
Novuspharma SpA
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 Novuspharma SpA filed Critical Novuspharma SpA
Priority to EP00920458A priority Critical patent/EP1173420A2/fr
Priority to AU41033/00A priority patent/AU4103300A/en
Priority to JP2000604021A priority patent/JP2002539114A/ja
Publication of WO2000053581A2 publication Critical patent/WO2000053581A2/fr
Publication of WO2000053581A3 publication Critical patent/WO2000053581A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones
    • 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
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/66—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Pyrrole Compounds (AREA)

Abstract

L'invention concerne des composés de formule générale (I), dans laquelle Y est O, S ou NH; n est 0 ou 1; X est choisi dans le groupe formé de NH-CO-NH, -NH-CO-, NH-SO2-, -NH-, -CO-NH-, -CO-NH-NH-, -NH-NH-CO-, -NH-NH-SO2-, -NH-CO-CO-, -NH-CO-CH2-, -NH-NH-, -NH-NH-CO-NH-, -NH-CO-NH-NH-, -NH-CO-NH-NH-, -CO-, -NH-SO2-NH-, -CO-NH-CO-NH-, -NH-CO-NH-CO-, -NH-CO-NH-SO2-, -NH-C(=NH)-NH-NH-, -NH-NH-C(=NH)-NH-, -CH=CH-, -CO-CH=CH-, -CH=CH-CO-, cyclopropane-1,2-di-yle, -NH-CH(COORC)-; R1 est choisi dans le groupe formé de H, alkyle, -(CH2)p-A, dans lequel p = 0-4 et A =OH, -NRaRb, -COORc, -CONRaRb, -CONH(CH2)q-NRaRb, -CONH(CH2)q-COORc, où q = 1-4, Ra et Rb sont H, alkyle, ou Ra et Rb ainsi que l'atome d'azote sont liés pour former un noyau hétérocyclique à 4-7 éléments; Rc est H, alkyle ou alcali ou un métal alcalino-terreux; R est alkyle, cycloalkyle, arylalkyle, naphtyle, phényle facultativement substitué, un noyau hétérocyclique aromatique ou non aromatique à 5 ou 6 éléments facultativement benzocondensé; R2 est H ou alkyle et le pointillé représente une liaison facultative, que l'on peut utiliser comme médicaments, en particulier comme agents antitumoraux.
PCT/EP2000/001721 1999-03-05 2000-03-01 Composes heterocycliques ayant une activite antitumorale Ceased WO2000053581A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP00920458A EP1173420A2 (fr) 1999-03-05 2000-03-01 Composes heterocycliques ayant une activite antitumorale
AU41033/00A AU4103300A (en) 1999-03-05 2000-03-01 Heterocyclic compounds having antitumor activity
JP2000604021A JP2002539114A (ja) 1999-03-05 2000-03-01 抗腫瘍活性を有する複素環化合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI99A000456 1999-03-05
IT1999MI000456A IT1309593B1 (it) 1999-03-05 1999-03-05 Composti eterociclici ad attivita' antitumorale.

Publications (2)

Publication Number Publication Date
WO2000053581A2 WO2000053581A2 (fr) 2000-09-14
WO2000053581A3 true WO2000053581A3 (fr) 2000-12-21

Family

ID=11382169

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/001721 Ceased WO2000053581A2 (fr) 1999-03-05 2000-03-01 Composes heterocycliques ayant une activite antitumorale

Country Status (5)

Country Link
EP (1) EP1173420A2 (fr)
JP (1) JP2002539114A (fr)
AU (1) AU4103300A (fr)
IT (1) IT1309593B1 (fr)
WO (1) WO2000053581A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101208082A (zh) 2005-06-28 2008-06-25 默克公司 烟酸受体激动剂、含有所述化合物的组合物和治疗方法
WO2017046355A1 (fr) 2015-09-18 2017-03-23 Boehringer Ingelheim International Gmbh Procédé stéréosélectif
CN109651310B (zh) * 2018-12-26 2022-07-22 华南师范大学 一种n-呋喃酮基芳基磺酰肼类衍生物及其制备方法和应用
CN113980004B (zh) * 2021-10-18 2023-07-04 成都大学 一种具有呋喃-2(5h)-酮骨架的化合物及其制备方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3472878A (en) * 1969-01-27 1969-10-14 American Home Prod N-(hydroxyaryl)aconamides
US3496187A (en) * 1967-03-20 1970-02-17 American Home Prod N-(heterocyclyl)aconamides
DE2108926A1 (en) * 1971-02-25 1972-08-31 Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen 3-acyl-4-hydroxy-2-butenoic acid lactone prepn - from an alpha-ketocarboxylic acid and an alpha beta unsatd carbonyl cpd
EP0560389A1 (fr) * 1992-03-13 1993-09-15 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Lactone possédant une activité immunosuppréssive
WO1996040673A1 (fr) * 1995-06-07 1996-12-19 Sugen, Inc. Nouveaux composes de type uree et thiouree
EP0841063A1 (fr) * 1996-03-27 1998-05-13 Toray Industries, Inc. Derives de cetone et usage medicinal
WO1999012917A1 (fr) * 1997-09-05 1999-03-18 Roche Diagnostics Gmbh Derives d'ureido et thioureido de 4-amino-2(5h)-furanones et 4-amino-2(5h)-thiophenones en tant qu'agents anti-tumoraux

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3496187A (en) * 1967-03-20 1970-02-17 American Home Prod N-(heterocyclyl)aconamides
US3472878A (en) * 1969-01-27 1969-10-14 American Home Prod N-(hydroxyaryl)aconamides
DE2108926A1 (en) * 1971-02-25 1972-08-31 Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen 3-acyl-4-hydroxy-2-butenoic acid lactone prepn - from an alpha-ketocarboxylic acid and an alpha beta unsatd carbonyl cpd
EP0560389A1 (fr) * 1992-03-13 1993-09-15 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Lactone possédant une activité immunosuppréssive
WO1996040673A1 (fr) * 1995-06-07 1996-12-19 Sugen, Inc. Nouveaux composes de type uree et thiouree
EP0841063A1 (fr) * 1996-03-27 1998-05-13 Toray Industries, Inc. Derives de cetone et usage medicinal
WO1999012917A1 (fr) * 1997-09-05 1999-03-18 Roche Diagnostics Gmbh Derives d'ureido et thioureido de 4-amino-2(5h)-furanones et 4-amino-2(5h)-thiophenones en tant qu'agents anti-tumoraux

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
HIYAMA T ET AL: "SYNTHESIS OF 4-AMINO-2(5H)-FURANONES THROUGH INTRA- AND INTERMOLECULAR NITRILE ADDITION OF ESTER ENOLATES. CONTRICTION OF CARBON FRAMEWORK OF AN ANTITUMOR ANTIBIOTIC BASIDALIN", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN,JP,JAPAN PUBLICATIONS TRADING CO. TOKYO, vol. 60, no. 6, 1 June 1987 (1987-06-01), pages 2139 - 2150, XP002053923, ISSN: 0009-2673 *
K.-B. WALTER ET AL.: "Stickstoffhaltige Derivate der Tetronsäure", ARCHIV DER PHARMAZIE., vol. 320, 1987, VCH VERLAGSGESELLSCHAFT MBH, WEINHEIM., DE, pages 749 - 755, XP000946110, ISSN: 0365-6233 *
MEULDERMANS W ET AL: "EXCRETION AND BIOTRANFORMATION OF CISAPRIDE IN RATS AFTER ORAL ADMINISTRATION", DRUG METABOLISM AND DISPOSITION,US,WILLIAMS AND WILKINS., BALTIMORE, MD, vol. 16, no. 3, 1 May 1988 (1988-05-01), pages 410 - 419, XP000577692, ISSN: 0090-9556 *
MEULDERMANS W ET AL: "EXCRETION AND BIOTRANSFORMATION OF CISAPRIDE IN DOGS AND HUMANS AFTER ORAL ADMINISTATION", DRUG METABOLISM AND DISPOSITION,US,WILLIAMS AND WILKINS., BALTIMORE, MD, vol. 16, no. 3, 1 May 1988 (1988-05-01), pages 403 - 409, XP000577694, ISSN: 0090-9556 *
R. J. CAPON ET AL.: "Synthesis of the Thermolysis Product of 6beta-Hydroxyaplystatin", JOURNAL OF CHEMICAL RESEARCH (S), 1987, pages 118 - 119, XP000946119 *
T. MOMOSE ET AL.: "2(3H)- and 2(5H)-Furanones. III. An Efficient Synthesis and the Eschenmoser-Mannich Reaction of N-substituted 4-Amino-2(5H)-furanones", HETEROCYCLES., vol. 27, no. 8, 1988, AMSTERDAM NL, pages 1907 - 1923, XP000946112 *
Y. MORISHITA ET AL.: "Regressive Effects of Various Chemopresentive Agents on Azoxymethane-induced Aberrant Crypt Foci in the Rat Colon", JAPANESE JOURNAL OF CANCER RESEARCH, vol. 88, no. 9, 1997, pages 815 - 820, XP000946118 *

Also Published As

Publication number Publication date
WO2000053581A2 (fr) 2000-09-14
JP2002539114A (ja) 2002-11-19
ITMI990456A1 (it) 2000-09-05
AU4103300A (en) 2000-09-28
EP1173420A2 (fr) 2002-01-23
IT1309593B1 (it) 2002-01-24

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