CA2463469A1 - 4-(4-alkoxy-3-hydroxyphenyl)-2-pyrrolidone derivatives as pde-4 inhibitors for the treatment of neurological syndromes - Google Patents

4-(4-alkoxy-3-hydroxyphenyl)-2-pyrrolidone derivatives as pde-4 inhibitors for the treatment of neurological syndromes Download PDF

Info

Publication number
CA2463469A1
CA2463469A1 CA002463469A CA2463469A CA2463469A1 CA 2463469 A1 CA2463469 A1 CA 2463469A1 CA 002463469 A CA002463469 A CA 002463469A CA 2463469 A CA2463469 A CA 2463469A CA 2463469 A1 CA2463469 A1 CA 2463469A1
Authority
CA
Canada
Prior art keywords
alkyl
substituted
halogen
combinations
carbon atoms
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
CA002463469A
Other languages
English (en)
French (fr)
Inventor
Ruiping Liu
Michael De Vivo
Hans-Jurgen Ernst Hess
Allen Hopper
Erik Kuester
Ashok Tehim
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.)
Memory Pharmaceuticals Corp
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 CA2463469A1 publication Critical patent/CA2463469A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • 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
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D409/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/12—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 chain containing hetero atoms as chain links

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Pulmonology (AREA)
  • Virology (AREA)
  • Dermatology (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Psychiatry (AREA)
  • Oncology (AREA)
  • Obesity (AREA)
  • Psychology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Endocrinology (AREA)
  • AIDS & HIV (AREA)
CA002463469A 2001-10-16 2002-10-16 4-(4-alkoxy-3-hydroxyphenyl)-2-pyrrolidone derivatives as pde-4 inhibitors for the treatment of neurological syndromes Abandoned CA2463469A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US32931401P 2001-10-16 2001-10-16
US60/329,314 2001-10-16
PCT/US2002/032834 WO2003032981A1 (en) 2001-10-16 2002-10-16 4-(4-alkoxy-3-hydroxyphenyl)-2-pyrrolidone derivatives as pde-4 inhibitors for the treatment of neurological syndromes

Publications (1)

Publication Number Publication Date
CA2463469A1 true CA2463469A1 (en) 2003-04-24

Family

ID=23284824

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002463469A Abandoned CA2463469A1 (en) 2001-10-16 2002-10-16 4-(4-alkoxy-3-hydroxyphenyl)-2-pyrrolidone derivatives as pde-4 inhibitors for the treatment of neurological syndromes

Country Status (20)

Country Link
US (3) US7235579B2 (enExample)
EP (1) EP1435944B1 (enExample)
JP (2) JP4484515B2 (enExample)
KR (2) KR100951218B1 (enExample)
CN (1) CN1604776A (enExample)
AT (1) ATE444065T1 (enExample)
AU (1) AU2002335015B8 (enExample)
BR (1) BR0213660A (enExample)
CA (1) CA2463469A1 (enExample)
CO (1) CO5570674A2 (enExample)
DE (1) DE60233884D1 (enExample)
ES (1) ES2334650T3 (enExample)
HR (1) HRP20040409A2 (enExample)
IL (1) IL161317A0 (enExample)
MX (1) MXPA04003516A (enExample)
NO (1) NO20042024L (enExample)
NZ (1) NZ532288A (enExample)
RU (2) RU2340600C2 (enExample)
WO (1) WO2003032981A1 (enExample)
ZA (1) ZA200402856B (enExample)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9931318B2 (en) 2003-04-08 2018-04-03 Dart Neuroscience (Cayman) Ltd. Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation
US8153646B2 (en) 2000-08-10 2012-04-10 Dart Neuroscience (Cayman) Ltd. Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation
DE60140074D1 (de) * 2000-12-14 2009-11-12 Burnham Inst Non-apoptotische formen des zelltods und verfahren zur modulation
ES2334650T3 (es) 2001-10-16 2010-03-15 Memory Pharmaceuticals Corporation Derivados de 4(4-alkoxi-3-hidroxifenil)-2-pirrolidona como inhibidores de pde-4 para el tratamiento de sindromes neurologicos.
US20030157053A1 (en) * 2002-02-19 2003-08-21 Sabina Sperandio Modulators of paraptosis and related methods
US7495016B2 (en) 2002-10-21 2009-02-24 Irm Llc Pyrrolidones with anti-HIV activity
ES2211344B1 (es) * 2002-12-26 2005-10-01 Almirall Prodesfarma, S.A. Nuevos derivados de piridazin-3(2h)-ona.
WO2004094375A2 (en) * 2003-04-16 2004-11-04 Memory Pharmaceuticals Corporation 4 - (3,4 - disubstituted phenyl) - pyrrolidin-2-one compounds as phosphodiesterase 4 inhibitors
EP1624873A2 (en) * 2003-04-28 2006-02-15 AB Science Use of tyrosine kinase inhibitors for treating cerebral ischemia
ES2251866B1 (es) * 2004-06-18 2007-06-16 Laboratorios Almirall S.A. Nuevos derivados de piridazin-3(2h)-ona.
ES2251867B1 (es) * 2004-06-21 2007-06-16 Laboratorios Almirall S.A. Nuevos derivados de piridazin-3(2h)-ona.
DOP2005000123A (es) 2004-07-02 2011-07-15 Merck Sharp & Dohme Inhibidores de cetp
WO2006044955A1 (en) * 2004-10-20 2006-04-27 Memory Pharmaceuticals Corporation Phosphodiesterase 4 inhibitors
RU2418793C2 (ru) * 2005-11-15 2011-05-20 Оцука Фармасьютикал Ко., Лтд. Соединение оксазола и фармацевтическая композиция
CA2635262C (en) * 2005-12-30 2011-08-16 Merck & Co., Inc. 1, 3-oxazolidin-2-one derivatives useful as cetp inhibitors
EP2021001B1 (en) * 2006-05-19 2012-12-12 Helicon Therapeutics, Inc. Phosphodiesterase 4 inhibitors for motor rehabilitation
ES2320954B1 (es) * 2007-03-02 2010-03-16 Laboratorio Almirall S.A. Nuevo procedimiento de preparacion de 3-metil-4-fenilisoxazolo (3,4-d)iridazin-7(6h)-ona.
WO2009067607A2 (en) * 2007-11-20 2009-05-28 Memory Pharmaceuticals Corporation Combinations of pde4 inhibitors and antipsychotics for the treatment of psychotic disorders
CN107243007A (zh) 2008-10-16 2017-10-13 约翰斯.霍普金斯大学 改善认知功能的方法和组合物
WO2010075086A2 (en) * 2008-12-15 2010-07-01 Auspex Pharmaceuticals, Inc. Pyrrolidinone inhibitors of pde-4
SI2443089T1 (sl) * 2009-06-18 2014-07-31 Concert Pharmaceuticals, Inc. Devterirani derivati izoindolin-1,3-diona kot inhibitorji pde4 in tnf-alfa
EP3610890A1 (en) 2012-11-14 2020-02-19 The Johns Hopkins University Methods and compositions for treating schizophrenia
KR20150119370A (ko) 2013-02-19 2015-10-23 화이자 인코포레이티드 Cns 장애 및 다른 장애의 치료를 위한 pde4 동종효소의 억제제로서의 아자벤즈이미다졸 화합물
EP2968237A4 (en) 2013-03-15 2016-08-31 Univ Johns Hopkins METHOD AND COMPOSITIONS FOR IMPROVING COGNITIVE FUNCTION
CN105142623A (zh) 2013-03-15 2015-12-09 艾吉因生物股份有限公司 用于改善认知功能的方法和组合物
EP3172210B1 (en) 2014-07-24 2020-01-15 Pfizer Inc Pyrazolopyrimidine compounds
WO2016020786A1 (en) 2014-08-06 2016-02-11 Pfizer Inc. Imidazopyridazine compounds
US10159648B2 (en) 2015-05-22 2018-12-25 Agenebio, Inc. Extended release pharmaceutical compositions of levetiracetam
JP2017141222A (ja) * 2016-02-09 2017-08-17 国立大学法人帯広畜産大学 パーキンソン病に併発した認知障害の治療剤及びそのスクリーニング方法
TWI877358B (zh) * 2020-04-29 2025-03-21 大陸商廣東東陽光藥業股份有限公司 取代的吡咯烷類化合物及其在藥物中的應用
CN112479966B (zh) * 2020-12-11 2022-05-17 南京工业大学 一种咯利普兰的合成方法

Family Cites Families (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4193926A (en) 1974-03-20 1980-03-18 Schering Aktiengesellschaft 4-(Polyalkoxy phenyl)-2-pyrrolidones
DE2413935A1 (de) 1974-03-20 1975-10-16 Schering Ag 4-(polyalkoxy-phenyl)-2-pyrrolidone
DE2834114A1 (de) * 1978-08-01 1980-02-14 Schering Ag Polyalkoxyphenylpyrrolidone iii, verfahren zu ihrer herstellung und ihre verwendung
DE3438839A1 (de) * 1984-10-19 1986-04-24 Schering AG, 1000 Berlin und 4709 Bergkamen Pharmazeutische praeparate
US5128358A (en) * 1988-01-19 1992-07-07 Pfizer Inc. Aryl substituted nitrogen heterocyclic antidepressants
DE3921593A1 (de) 1989-06-28 1991-01-10 Schering Ag Verfahren zur racemattrennung von 4-aryl-2-oxo-pyrrolidin-3-carbonsaeure-ester
GB9009395D0 (en) 1990-04-26 1990-06-20 Orion Yhtymae Oy Cyclic hydroxamic acids and their use
US5935978A (en) 1991-01-28 1999-08-10 Rhone-Poulenc Rorer Limited Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic- or heteroatom-containing linking group
PT100441A (pt) * 1991-05-02 1993-09-30 Smithkline Beecham Corp Pirrolidinonas, seu processo de preparacao, composicoes farmaceuticas que as contem e uso
AU2869092A (en) * 1991-10-11 1993-05-03 Smithkline Beecham Corporation Heterocyclic 3-phenylpyrrolidin-2-ones, their preparation and use for the manufacture of a medicament for inhibiting tumor necrosis factor production
ES2102036T3 (es) 1992-06-15 1997-07-16 Celltech Therapeutics Ltd Derivados con grupo fenilo trisustituido utilizados como inhibidores selectivos de la fosfodiesterasa iv.
US5814651A (en) 1992-12-02 1998-09-29 Pfizer Inc. Catechol diethers as selective PDEIV inhibitors
ATE234270T1 (de) * 1992-12-02 2003-03-15 Pfizer Cathecoldiether als selektive pde iv hemmungsmittel
TW263495B (enExample) 1992-12-23 1995-11-21 Celltech Ltd
US5665754A (en) * 1993-09-20 1997-09-09 Glaxo Wellcome Inc. Substituted pyrrolidines
JPH07300455A (ja) * 1994-03-08 1995-11-14 Mitsubishi Chem Corp ３−フェニルピロリジン誘導体
CA2186371A1 (en) 1994-03-25 1995-10-05 Robert T. Foster Enhancement of the efficacy of dihydropyridines by deuteration
US6334997B1 (en) 1994-03-25 2002-01-01 Isotechnika, Inc. Method of using deuterated calcium channel blockers
PT758233E (pt) * 1994-04-21 2004-04-30 Schering Ag Inibidores pde iv para o tratamento da esclerose multipla
GB9412383D0 (en) 1994-06-21 1994-08-10 Celltech Ltd Chemical compound
DE19601938A1 (de) 1996-01-12 1997-07-17 Schering Ag Neue Phosphodiesteraseinhibitoren
JPH1072415A (ja) 1996-06-26 1998-03-17 Nikken Chem Co Ltd ３−アニリノ−２−シクロアルケノン誘導体
GB9622386D0 (en) 1996-10-28 1997-01-08 Sandoz Ltd Organic compounds
US6235736B1 (en) 1997-06-24 2001-05-22 Nikken Chemicals Co., Ltd. 3-anilino-2-cycloalkenone derivatives
JP3085249B2 (ja) 1997-07-09 2000-09-04 松下電器産業株式会社 ホットプレート
US6403597B1 (en) * 1997-10-28 2002-06-11 Vivus, Inc. Administration of phosphodiesterase inhibitors for the treatment of premature ejaculation
US6258833B1 (en) 1999-12-23 2001-07-10 Icos Corporation Cyclic AMP-specific phosphodiesterase inhibitors
US6372777B1 (en) 1999-12-23 2002-04-16 Icos Corporation Cyclic AMP-specific phosphodiesterase inhibitors
GB0004297D0 (en) 2000-02-23 2000-04-12 Ucb Sa 2-oxo-1 pyrrolidine derivatives process for preparing them and their uses
EP1265861A2 (en) 2000-03-16 2002-12-18 Inflazyme Pharmaceuticals, Ltd. Benzylated pde4 inhibitors
WO2002045749A2 (en) 2000-11-02 2002-06-13 Research Foundation Of City University Of New York Methods for stimulating nervous system regeneration and repair by inhibition phosphodiesterase type 4
US6495154B1 (en) * 2000-11-21 2002-12-17 Vivus Inc. On demand administration of clomipramine and salts thereof to treat premature ejaculation
ES2334650T3 (es) 2001-10-16 2010-03-15 Memory Pharmaceuticals Corporation Derivados de 4(4-alkoxi-3-hidroxifenil)-2-pirrolidona como inhibidores de pde-4 para el tratamiento de sindromes neurologicos.
WO2004094375A2 (en) 2003-04-16 2004-11-04 Memory Pharmaceuticals Corporation 4 - (3,4 - disubstituted phenyl) - pyrrolidin-2-one compounds as phosphodiesterase 4 inhibitors

Also Published As

Publication number Publication date
RU2340600C2 (ru) 2008-12-10
ZA200402856B (en) 2005-01-25
WO2003032981A1 (en) 2003-04-24
CO5570674A2 (es) 2005-10-31
RU2008123376A (ru) 2009-12-27
DE60233884D1 (de) 2009-11-12
EP1435944B1 (en) 2009-09-30
HRP20040409A2 (en) 2005-06-30
CN1604776A (zh) 2005-04-06
AU2002335015B8 (en) 2006-11-30
US20030139406A1 (en) 2003-07-24
KR20050037404A (ko) 2005-04-21
US20050272803A1 (en) 2005-12-08
IL161317A0 (en) 2004-09-27
US7235579B2 (en) 2007-06-26
NZ532288A (en) 2005-12-23
AU2002335015B2 (en) 2006-11-02
KR100951218B1 (ko) 2010-04-05
ES2334650T3 (es) 2010-03-15
JP4484515B2 (ja) 2010-06-16
KR20090080573A (ko) 2009-07-24
RU2004115333A (ru) 2005-10-27
JP2009286797A (ja) 2009-12-10
NO20042024L (no) 2004-05-14
US20090176799A1 (en) 2009-07-09
JP2005508961A (ja) 2005-04-07
MXPA04003516A (es) 2004-07-23
BR0213660A (pt) 2004-08-24
ATE444065T1 (de) 2009-10-15
EP1435944A1 (en) 2004-07-14

Similar Documents

Publication Publication Date Title
US7235579B2 (en) Phosphodiesterase 4 inhibitors
US7696198B2 (en) Phosphodiesterase 4 inhibitors
AU2002335015A1 (en) 4-(4-alkoxy-3-hydroxyphenyl)-2-pyrrolidone derivatives as pde-4 inhibitors for the treatment of neurological syndromes
AU2002313673B2 (en) Trifluoromethylpurines as phosphodiesterase 4 inhibitors
EP1569908B1 (en) Pyridine n-oxide compounds as phosphodiesterase 4 inhibitors
US20100093806A1 (en) Phosphodiesterase 4 inhibitors, including aminoindazole and aminobenzofuran analogs
US7153871B2 (en) Phosphodiesterase 4 inhibitors, including aminoindazole and aminobenzofuran analogs
MXPA05011055A (en) 4 - (3,4 - disubstituted phenyl) - pyrrolidin-2-one compounds as phosphodiesterase 4 inhibitors
NZ547469A (en) 6-Amino-1H-indazole and 4-aminobenzofuran compounds as phosphodiesterase 4 inhibitors

Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued
FZDE Discontinued

Effective date: 20111017