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CA2270301A1 - Hydroxyindoles, their use as inhibitors of phosphodiesterase 4, and processes for their preparation - Google Patents

Hydroxyindoles, their use as inhibitors of phosphodiesterase 4, and processes for their preparation Download PDF

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Publication number
CA2270301A1
CA2270301A1 CA002270301A CA2270301A CA2270301A1 CA 2270301 A1 CA2270301 A1 CA 2270301A1 CA 002270301 A CA002270301 A CA 002270301A CA 2270301 A CA2270301 A CA 2270301A CA 2270301 A1 CA2270301 A1 CA 2270301A1
Authority
CA
Canada
Prior art keywords
phosphodiesterase
inhibitors
processes
preparation
hydroxyindoles
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.)
Granted
Application number
CA002270301A
Other languages
French (fr)
Other versions
CA2270301C (en
Inventor
Norbert Hofgen
Ute Egerland
Hildegard Poppe
Degenhard Marx
Istvan Szelenyi
Thomas Kronbach
Emmanuel E. Polymeropoulos
Sabine Heer
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.)
Elbion GmbH
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 CA2270301A1 publication Critical patent/CA2270301A1/en
Application granted granted Critical
Publication of CA2270301C publication Critical patent/CA2270301C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—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
    • C07D209/24—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 with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—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
    • C07D209/22—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 with an aralkyl radical attached to the ring nitrogen atom
    • 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

Landscapes

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

Abstract

The invention relates to new hydroxyindoles of the Formula, (see formula 1) their use as inhibitors of phosphodiesterase 4 and processes for their preparation.
CA002270301A 1998-04-28 1999-04-28 Hydroxyindoles, their use as inhibitors of phosphodiesterase 4, and processes for their preparation Expired - Fee Related CA2270301C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19818964.8 1998-04-28
DE19818964A DE19818964A1 (en) 1998-04-28 1998-04-28 New hydroxy-indole derivatives useful in treatment of degenerative joint disease, viral and parasitic infections, bronchial, dermatological, neurodegenerative and prostate disorders, etc.

Publications (2)

Publication Number Publication Date
CA2270301A1 true CA2270301A1 (en) 1999-10-28
CA2270301C CA2270301C (en) 2006-08-22

Family

ID=7866051

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002270301A Expired - Fee Related CA2270301C (en) 1998-04-28 1999-04-28 Hydroxyindoles, their use as inhibitors of phosphodiesterase 4, and processes for their preparation

Country Status (5)

Country Link
CN (1) CN1321981C (en)
CA (1) CA2270301C (en)
DE (1) DE19818964A1 (en)
RU (1) RU2217422C2 (en)
ZA (1) ZA200005540B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7947705B2 (en) * 2003-04-24 2011-05-24 Biotie Therapies Gmbh 7-azaindoles and the use thereof as therapeutic agents

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19962300A1 (en) * 1999-12-23 2001-06-28 Asta Medica Ag New N-benzylindolyl glyoxylic acid derivatives are useful as antitumor agents
US6903104B2 (en) 2001-12-06 2005-06-07 National Health Research Institutes Indol-3-YL-2-oxoacetamide compounds and methods of use thereof
HRP20050201A2 (en) * 2002-08-01 2005-04-30 Elbion Ag Method for producing highly pure hydroxy indolyl glyoxylic acid amideslyoxylic acid amides
DE10241407A1 (en) * 2002-09-06 2004-03-18 Elbion Ag Treatment of non-allergic rhinitis with selective phosphodiesterase 4 inhibitors
DE10253426B4 (en) * 2002-11-15 2005-09-22 Elbion Ag Novel hydroxyindoles, their use as inhibitors of phosphodiesterase 4 and methods for their preparation
DE10318609A1 (en) * 2003-04-24 2004-11-11 Elbion Ag 5-hydroxyindoles with N-oxide groups and their use as therapeutic agents
TW200738677A (en) * 2005-06-27 2007-10-16 Elbion Ag Nitro-substituted hydroxyindoles, their use as inhibitors of phosphodiesterase 4, and processes for preparing them
AU2007206016A1 (en) 2006-01-13 2007-07-26 Wyeth Sulfonyl substituted 1H-indoles as ligands for the 5-hydroxytryptamine receptors

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5192770A (en) * 1990-12-07 1993-03-09 Syntex (U.S.A.) Inc. Serotonergic alpha-oxoacetamides
DK0672031T3 (en) * 1992-12-02 2003-06-10 Pfizer Catechol dieters as selective PDE IV inhibitors
US5424329A (en) * 1993-08-18 1995-06-13 Warner-Lambert Company Indole-2-carboxamides as inhibitors of cell adhesion
US5502072A (en) * 1993-11-26 1996-03-26 Pfizer Inc. Substituted oxindoles
US5489586A (en) * 1994-03-07 1996-02-06 Warner-Lambert Company Method for treating inflammatory disease in humans
DE19511916A1 (en) * 1994-08-03 1996-02-08 Asta Medica Ag New N-benzylindole and benzopyrazole derivatives with anti-asthmatic, anti-allergic, anti-inflammatory and immunomodulating effects
US5728844A (en) * 1995-08-29 1998-03-17 Celgene Corporation Immunotherapeutic agents
TW429148B (en) * 1995-10-27 2001-04-11 Pfizer Pharmaceutical agents for the treatment of acute and chronic inflammatory diseases
EP2223920A3 (en) * 1996-06-19 2011-09-28 Aventis Pharma Limited Substituted azabicyclic compounds
CA2259927A1 (en) * 1996-07-12 1998-01-22 Leukosite, Inc. Chemokine receptor antagonists and methods of use therefor
AU717430B2 (en) * 1996-08-26 2000-03-23 Genetics Institute, Llc Inhibitors of phospholipase enzymes
DE19636150A1 (en) * 1996-09-06 1998-03-12 Asta Medica Ag N-substituted indole-3-glyoxylamides with antiasthmatic, antiallergic and immunosuppressive / immunomodulating effects

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7947705B2 (en) * 2003-04-24 2011-05-24 Biotie Therapies Gmbh 7-azaindoles and the use thereof as therapeutic agents

Also Published As

Publication number Publication date
CA2270301C (en) 2006-08-22
ZA200005540B (en) 2001-03-27
HK1066804A1 (en) 2005-04-01
CN1699342A (en) 2005-11-23
RU2217422C2 (en) 2003-11-27
CN1321981C (en) 2007-06-20
DE19818964A1 (en) 1999-11-04

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