[go: up one dir, main page]

WO2000053581A3 - Heterocyclic compounds having antitumor activity - Google Patents

Heterocyclic compounds having antitumor activity Download PDF

Info

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
French (fr)
Other versions
WO2000053581A2 (en
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/en
Priority to AU41033/00A priority patent/AU4103300A/en
Priority to JP2000604021A priority patent/JP2002539114A/en
Publication of WO2000053581A2 publication Critical patent/WO2000053581A2/en
Publication of WO2000053581A3 publication Critical patent/WO2000053581A3/en
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)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (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

Compounds of general formula (I) in which: Y is O, S or NH; n is 0 or 1; X is selected from the group consisting of -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-, -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-, cyclopropan-1,2-di-yl, -NH-CH(COORC)-; R1 is selected from the group consisting of H, alkyl, -(CH2)p-A, wherein p = 0-4 and A = OH, -NRaRb, -COORc, -CONRaRb, -CONH(CH2)q-NRaRb, -CONH(CH2)q-COORc, wherein q = 1-4, Ra and Rb are H, alkyl, or Ra and Rb together with the nitrogen atom they are linked to form a 4-7 membered heterocyclic ring; Rc is H, alkyl or alkali or alkaline-earth metal; R is alkyl, cycloalkyl, arylalkyl, naphthyl, optionally substituted phenyl, aromatic or non aromatic 5 or 6 membered heterocyclic ring optionally benzofused; R2 is H or alkyl and the dotted line means an optional bond, for use as medicaments, in particular as antitumor agents.
PCT/EP2000/001721 1999-03-05 2000-03-01 Heterocyclic compounds having antitumor activity Ceased WO2000053581A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP00920458A EP1173420A2 (en) 1999-03-05 2000-03-01 Heterocyclic compounds having antitumor activity
AU41033/00A AU4103300A (en) 1999-03-05 2000-03-01 Heterocyclic compounds having antitumor activity
JP2000604021A JP2002539114A (en) 1999-03-05 2000-03-01 Heterocyclic compounds having antitumor activity

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI99A000456 1999-03-05
IT1999MI000456A IT1309593B1 (en) 1999-03-05 1999-03-05 HETEROCYCLIC COMPOUNDS WITH ANTI-TUMOR ACTIVITY.

Publications (2)

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

Family

ID=11382169

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/001721 Ceased WO2000053581A2 (en) 1999-03-05 2000-03-01 Heterocyclic compounds having antitumor activity

Country Status (5)

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

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PE20070097A1 (en) 2005-06-28 2007-03-08 Merck Sharp & Dohme NIACIN RECEPTOR AGONISTS AND COMPOSITIONS CONTAINING SUCH COMPOUNDS
EP3599234B1 (en) 2015-09-18 2021-04-07 Boehringer Ingelheim International GmbH Stereoselective process
CN109651310B (en) * 2018-12-26 2022-07-22 华南师范大学 N-furanone aryl sulfonyl hydrazide derivative and preparation method and application thereof
CN113980004B (en) * 2021-10-18 2023-07-04 成都大学 Compound with furan-2 (5H) -ketone skeleton and preparation method thereof

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 (en) * 1992-03-13 1993-09-15 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Lactone with immunosuppressive activity
WO1996040673A1 (en) * 1995-06-07 1996-12-19 Sugen, Inc. Novel urea- and thiourea-type compounds
EP0841063A1 (en) * 1996-03-27 1998-05-13 Toray Industries, Inc. Ketone derivatives and medicinal use thereof
WO1999012917A1 (en) * 1997-09-05 1999-03-18 Roche Diagnostics Gmbh Ureido and thioureido derivatives of 4-amino-2(5h)-furanones and 4-amino-2(5h)-thiophenones as antitumor agents

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 (en) * 1992-03-13 1993-09-15 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Lactone with immunosuppressive activity
WO1996040673A1 (en) * 1995-06-07 1996-12-19 Sugen, Inc. Novel urea- and thiourea-type compounds
EP0841063A1 (en) * 1996-03-27 1998-05-13 Toray Industries, Inc. Ketone derivatives and medicinal use thereof
WO1999012917A1 (en) * 1997-09-05 1999-03-18 Roche Diagnostics Gmbh Ureido and thioureido derivatives of 4-amino-2(5h)-furanones and 4-amino-2(5h)-thiophenones as antitumor agents

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
IT1309593B1 (en) 2002-01-24
ITMI990456A1 (en) 2000-09-05
WO2000053581A2 (en) 2000-09-14
JP2002539114A (en) 2002-11-19
AU4103300A (en) 2000-09-28
EP1173420A2 (en) 2002-01-23

Similar Documents

Publication Publication Date Title
WO2004014860A3 (en) Fused heterocyclic compounds as peptidase inhibitors
MX9709951A (en) Benzamide derivatives and their use as vasopressin antagonists.
CA2156078A1 (en) New imidazopyridines
IL157179A0 (en) Fused heterocyclic compounds
TW200420542A (en) A compound having TGF β inhibition activity and a medicinal composition containing the same
GB0007405D0 (en) Compounds
GR3034398T3 (en) 2-[1',2',4'-triazol-3'-yloxymethylene]-anilides and their use as pest-control agents
AU5777490A (en) Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides
AU1282495A (en) Anthranilic acid derivative
EP0669324A4 (en) Quinazoline compound.
MXPA02003977A (en) INHIBITORS OF agr;L.
ATE339409T1 (en) TRICYCLIC COMPOUNDS
ZA953981B (en) New azolidinediones as antihyperglycemic agents
AU2267495A (en) Benzamide derivatives as vasopressin antagonists
AU1687199A (en) Nitrogen-containing heterocyclic compounds, their production and use
WO2001034601A3 (en) Imidazopyridine derivatives as phosphodiesterase vii inhibitors
EP1500652A4 (en) Quinazoline derivative and medicine
WO2001012202A3 (en) Use of chemical chelators as reversal agents for drug-induced neuromuscular block
EP1241158A4 (en) Compound having hydroxycarbonyl-halogenoalkyl side chain
WO2000046210A3 (en) New process for preparing pesticidal intermediates
CA2168563A1 (en) Benzopyrans and Pharmaceutical Compositions Containing Them
WO2000053581A3 (en) Heterocyclic compounds having antitumor activity
EP1026162A4 (en) Antirheumatic
MY129094A (en) Condensed polycyclic compounds
WO1994003425A3 (en) Carbostyril derivatives for the treatment of arrhythmia

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

WWE Wipo information: entry into national phase

Ref document number: 2000920458

Country of ref document: EP

ENP Entry into the national phase

Ref country code: JP

Ref document number: 2000 604021

Kind code of ref document: A

Format of ref document f/p: F

WWE Wipo information: entry into national phase

Ref document number: 09926115

Country of ref document: US

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWP Wipo information: published in national office

Ref document number: 2000920458

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 2000920458

Country of ref document: EP

DPE2 Request for preliminary examination filed before expiration of 19th month from priority date (pct application filed from 20040101)