CA2329422A1 - Pyrrolidines utilises comme inhibiteurs de neuraminidases - Google Patents

Pyrrolidines utilises comme inhibiteurs de neuraminidases Download PDF

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Publication number
CA2329422A1
CA2329422A1 CA002329422A CA2329422A CA2329422A1 CA 2329422 A1 CA2329422 A1 CA 2329422A1 CA 002329422 A CA002329422 A CA 002329422A CA 2329422 A CA2329422 A CA 2329422A CA 2329422 A1 CA2329422 A1 CA 2329422A1
Authority
CA
Canada
Prior art keywords
pyrrolidine
acetamido
carboxylic acid
cis
propen
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.)
Abandoned
Application number
CA002329422A
Other languages
English (en)
Inventor
Clarence J. Maring
Yu-Gui Gu
Hui-Ju Chen
Yuanwei Chen
David A. Degoey
William J. Flosi
Vincent L. Giranda
David J. Grampovnik
Warren M. Kati
Dale J. Kempf
Larry L. Klein
Allan C. Krueger
Zhen Lin
Darold L. Madigan
Keith F. Mcdaniel
Steven W. Muchmore
Hing L. Sham
Kent D. Stewart
Vincent S. Stoll
Minghua Sun
Gary T. Wang
Sheldon Wang
Yibo Xu
Ming C. Yeung
Chen Zhao
April Kennedy
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.)
Abbott Laboratories
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2329422A1 publication Critical patent/CA2329422A1/fr
Abandoned legal-status Critical Current

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    • 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
    • C07D207/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C07D207/327—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—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 no 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
    • C07D207/16—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
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Virology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pulmonology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyrrole Compounds (AREA)

Abstract

L'invention concerne les composés représentés par la formule (I). Ces composés servent à inhiber les neuraminidases dans des micro-organismes pathogènes, en particulier la neuraminidase de la grippe. L'invention concerne également des compositions et des procédés permettant de prévenir et de traiter les maladies causées par des micro-organismes comprenant une neuraminidase, des procédés de préparation de ces composés et des intermédiaires de synthèse utilisés dans ces procédés.
CA002329422A 1998-04-23 1999-04-12 Pyrrolidines utilises comme inhibiteurs de neuraminidases Abandoned CA2329422A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US6522598A 1998-04-23 1998-04-23
US09/065,225 1998-04-23
PCT/US1999/007945 WO1999054299A1 (fr) 1998-04-23 1999-04-12 Pyrrolidines utilises comme inhibiteurs de neuraminidases

Publications (1)

Publication Number Publication Date
CA2329422A1 true CA2329422A1 (fr) 1999-10-28

Family

ID=22061195

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002329422A Abandoned CA2329422A1 (fr) 1998-04-23 1999-04-12 Pyrrolidines utilises comme inhibiteurs de neuraminidases

Country Status (17)

Country Link
EP (1) EP1315698A1 (fr)
JP (1) JP2002512224A (fr)
CN (1) CN1328546A (fr)
AR (1) AR018196A1 (fr)
AU (1) AU3554599A (fr)
BG (1) BG104962A (fr)
BR (1) BR9909870A (fr)
CA (1) CA2329422A1 (fr)
CO (1) CO5011122A1 (fr)
HU (1) HUP0101224A3 (fr)
IL (1) IL138601A0 (fr)
NO (1) NO20005301L (fr)
PL (1) PL343678A1 (fr)
SK (1) SK15092000A3 (fr)
TR (1) TR200003065T2 (fr)
WO (1) WO1999054299A1 (fr)
ZA (1) ZA200005238B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ412898A3 (cs) 1996-06-14 1999-08-11 Biocryst Pharmaceuticals, Inc. Substituované cyklopentanové sloučeniny, použitelné jako inhibitory neuraminidázy
AR016162A1 (es) 1997-12-17 2001-06-20 Biocryst Pharm Inc Compuestos ciclopentano y ciclopenteno sustituidos que son de utilidad como inhibidores de la neuraminidasa y composicion que los contiene.
US6455571B1 (en) * 1998-04-23 2002-09-24 Abbott Laboratories Inhibitors of neuraminidases
AU1520300A (en) 1998-11-05 2000-05-29 Biocryst Pharmaceuticals, Inc. New cyclopentane and cyclopentene compounds and use for detecting influenza virus
WO2001080892A1 (fr) * 2000-04-25 2001-11-01 Sankyo Company, Limited Substances preventives de la grippe
US6518299B1 (en) 2000-10-20 2003-02-11 Biocryst Pharmaceuticals, Inc. Substituted pyrrolidine compounds useful as neuraminidase inhibitors
WO2002081441A1 (fr) * 2001-04-03 2002-10-17 Abbott Laboratories Procede de preparation d'inhibiteurs de pyrrolidine neuraminidase substitue
WO2003037894A1 (fr) * 2001-11-02 2003-05-08 Glaxo Group Limited Derives de heteroaryle acyle pyrrolidine a 4-(5-elements) utiles comme inhibiteurs de vhc
WO2003037895A1 (fr) * 2001-11-02 2003-05-08 Glaxo Group Limited Derives d'heteroaryl acyl pyrrolidine a 4 a 6 chainons utilises comme inhibiteurs de hcv
DE60325498D1 (de) 2002-10-24 2009-02-05 Glaxo Group Ltd 1-acyl-pyrrolidin-derivate für die behandlung von viralen infektionen
CN104402754B (zh) * 2014-11-25 2016-03-02 广东东阳光药业有限公司 作为神经氨酸酶抑制剂的化合物及其在药物中的应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4035961A1 (de) * 1990-11-02 1992-05-07 Thomae Gmbh Dr K Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE69607704T2 (de) * 1995-02-27 2000-12-28 Gilead Sciences Inc Neue selektive inhibitoren viraler oder bakterieller neuraminidasen
CZ412898A3 (cs) * 1996-06-14 1999-08-11 Biocryst Pharmaceuticals, Inc. Substituované cyklopentanové sloučeniny, použitelné jako inhibitory neuraminidázy
ZA988469B (en) * 1997-09-17 1999-03-17 Biocryst Pharm Inc Pyrrolidin-2-one compounds and their use as neuraminidase inhibitors

Also Published As

Publication number Publication date
AR018196A1 (es) 2001-10-31
IL138601A0 (en) 2001-10-31
HUP0101224A3 (en) 2002-12-28
AU3554599A (en) 1999-11-08
CN1328546A (zh) 2001-12-26
EP1315698A1 (fr) 2003-06-04
JP2002512224A (ja) 2002-04-23
BR9909870A (pt) 2000-12-19
BG104962A (bg) 2001-07-31
NO20005301D0 (no) 2000-10-20
ZA200005238B (en) 2001-12-04
NO20005301L (no) 2000-12-08
WO1999054299A1 (fr) 1999-10-28
TR200003065T2 (tr) 2001-02-21
HUP0101224A2 (hu) 2001-08-28
PL343678A1 (en) 2001-08-27
SK15092000A3 (sk) 2001-05-10
CO5011122A1 (es) 2001-02-28

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EEER Examination request
FZDE Discontinued