AU2002335015B8 - 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
AU2002335015B8
AU2002335015B8 AU2002335015A AU2002335015A AU2002335015B8 AU 2002335015 B8 AU2002335015 B8 AU 2002335015B8 AU 2002335015 A AU2002335015 A AU 2002335015A AU 2002335015 A AU2002335015 A AU 2002335015A AU 2002335015 B8 AU2002335015 B8 AU 2002335015B8
Authority
AU
Australia
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.)
Ceased
Application number
AU2002335015A
Other languages
English (en)
Other versions
AU2002335015B2 (en
AU2002335015A1 (en
Inventor
Michael De Vivo
Hans-Jurgen Ernst Hess
Allen Hopper
Erik Keuster
Ruiping Liu
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
Memory Pharmaceuticals Corp
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 Memory Pharmaceuticals Corp filed Critical Memory Pharmaceuticals Corp
Publication of AU2002335015A1 publication Critical patent/AU2002335015A1/en
Application granted granted Critical
Publication of AU2002335015B2 publication Critical patent/AU2002335015B2/en
Publication of AU2002335015B8 publication Critical patent/AU2002335015B8/en
Anticipated expiration legal-status Critical
Ceased 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)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Pulmonology (AREA)
  • Dermatology (AREA)
  • Virology (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Urology & Nephrology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Psychiatry (AREA)
  • Rheumatology (AREA)
  • Molecular Biology (AREA)
  • Obesity (AREA)
  • Psychology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Communicable Diseases (AREA)
  • Cardiology (AREA)
  • Endocrinology (AREA)
  • AIDS & HIV (AREA)
  • Vascular Medicine (AREA)
  • Ophthalmology & Optometry (AREA)
AU2002335015A 2001-10-16 2002-10-16 4-(4-alkoxy-3-hydroxyphenyl)-2-pyrrolidone derivatives as pde-4 inhibitors for the treatment of neurological syndromes Ceased AU2002335015B8 (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 (3)

Publication Number Publication Date
AU2002335015A1 AU2002335015A1 (en) 2003-07-03
AU2002335015B2 AU2002335015B2 (en) 2006-11-02
AU2002335015B8 true AU2002335015B8 (en) 2006-11-30

Family

ID=23284824

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2002335015A Ceased AU2002335015B8 (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 (OSRAM)
EP (1) EP1435944B1 (OSRAM)
JP (2) JP4484515B2 (OSRAM)
KR (2) KR20090080573A (OSRAM)
CN (1) CN1604776A (OSRAM)
AT (1) ATE444065T1 (OSRAM)
AU (1) AU2002335015B8 (OSRAM)
BR (1) BR0213660A (OSRAM)
CA (1) CA2463469A1 (OSRAM)
CO (1) CO5570674A2 (OSRAM)
DE (1) DE60233884D1 (OSRAM)
ES (1) ES2334650T3 (OSRAM)
HR (1) HRP20040409A2 (OSRAM)
IL (1) IL161317A0 (OSRAM)
MX (1) MXPA04003516A (OSRAM)
NO (1) NO20042024L (OSRAM)
NZ (1) NZ532288A (OSRAM)
RU (2) RU2340600C2 (OSRAM)
WO (1) WO2003032981A1 (OSRAM)
ZA (1) ZA200402856B (OSRAM)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8153646B2 (en) 2000-08-10 2012-04-10 Dart Neuroscience (Cayman) Ltd. Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation
US9931318B2 (en) 2003-04-08 2018-04-03 Dart Neuroscience (Cayman) Ltd. Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation
WO2002054066A2 (en) * 2000-12-14 2002-07-11 The Burnham Institute Non-apoptotic forms of cell death and methods of modulation
CA2463469A1 (en) 2001-10-16 2003-04-24 Memory Pharmaceuticals Corporation 4-(4-alkoxy-3-hydroxyphenyl)-2-pyrrolidone derivatives as pde-4 inhibitors for the treatment of neurological syndromes
US20030157053A1 (en) * 2002-02-19 2003-08-21 Sabina Sperandio Modulators of paraptosis and related methods
WO2004037784A2 (en) 2002-10-21 2004-05-06 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.
JP2006523710A (ja) * 2003-04-16 2006-10-19 メモリー・ファーマシューティカルズ・コーポレイション ホスホジエステラーゼ４インヒビター
US20070191267A1 (en) * 2003-04-28 2007-08-16 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
CN101166737A (zh) * 2004-10-20 2008-04-23 记忆药物公司 磷酸二酯酶4抑制剂
AU2006316079B2 (en) * 2005-11-15 2012-03-29 Otsuka Pharmaceutical Co., Ltd. Oxazole compound and pharmaceutical composition
WO2007079186A2 (en) * 2005-12-30 2007-07-12 Merck & Co., Inc. 1, 3-oxazolidin-2-one derivatives useful as cetp inhibitors
JP2009537568A (ja) * 2006-05-19 2009-10-29 ヘリコン セラピューティクス，インコーポレイテッド 認知および運動のリハビリテーションのためのホスホジエステラーゼ４インヒビター
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
EP3260118B1 (en) 2008-10-16 2021-03-24 The Johns Hopkins University Methods and compositions for improving cognitive function
WO2010075086A2 (en) * 2008-12-15 2010-07-01 Auspex Pharmaceuticals, Inc. Pyrrolidinone inhibitors of pde-4
EA021019B1 (ru) 2009-06-18 2015-03-31 Концерт Фармасьютикалс, Инк. Дейтерированные производные изоиндолин-1,3-диона
WO2014078568A1 (en) 2012-11-14 2014-05-22 The Johns Hopkins University Methods and compositions for treating schizophrenia
AP2015008663A0 (en) 2013-02-19 2015-08-31 Pfizer Azabenzimidazole compounds as inhibitors of PDE4 isozymes for the treatment of cns and other disorders
EP2968220B1 (en) 2013-03-15 2021-05-05 Agenebio, Inc. Methods and compositions for improving cognitive function
WO2014144663A1 (en) 2013-03-15 2014-09-18 The Johns Hopkins University Methods and compositions for improving cognitive function
EP3172210B1 (en) 2014-07-24 2020-01-15 Pfizer Inc Pyrazolopyrimidine compounds
SG11201700243YA (en) 2014-08-06 2017-02-27 Pfizer Imidazopyridazine compounds
NZ738682A (en) 2015-05-22 2022-01-28 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

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012495A (en) * 1974-03-20 1977-03-15 Schering Aktiengesellschaft 4-(Polyalkoxyphenyl)-2-pyrrolidones
US4219551A (en) * 1978-08-01 1980-08-26 Schering Aktiengesellschaft Aminoalkoxyphenylpyrrolidone antihypertonic agents and use thereof
WO1992019594A1 (en) * 1991-05-02 1992-11-12 Smithkline Beecham Corporation Pyrrolidinones
WO1993007141A1 (en) * 1991-10-11 1993-04-15 Smithkline Beecham Corporation Heterocyclic 3-phenylpyrrolidin-2-ones, their preparation and use for the manufacture of a medicament for inhibiting tumor necrosis factor production
WO1995028926A1 (en) * 1994-04-21 1995-11-02 Schering Aktiengesellschaft Pde iv inhibitors for treating multiple sclerosis

Family Cites Families (29)

* 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
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
ATE150447T1 (de) 1992-06-15 1997-04-15 Celltech Therapeutics Ltd Trisubstituierte phenylderivate als selektive phosphodiesterase iv inhibitoren
US5814651A (en) 1992-12-02 1998-09-29 Pfizer Inc. Catechol diethers as selective PDEIV inhibitors
BR9307570A (pt) * 1992-12-02 1999-05-25 Pfizer Diéteres de catecol como inibidores seletivos de pdeiv
TW263495B (OSRAM) 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
US6334997B1 (en) 1994-03-25 2002-01-01 Isotechnika, Inc. Method of using deuterated calcium channel blockers
CN1087725C (zh) 1994-03-25 2002-07-17 同位素技术有限公司 用氘代方法增强药物效果
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
CA2295106C (en) 1997-06-24 2007-03-13 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
WO2001068600A2 (en) 2000-03-16 2001-09-20 Inflazyme Pharmaceuticals Limited Benzylated pde4 inhibitors
JP2004532809A (ja) 2000-11-02 2004-10-28 リサーチ ファウンデーション オブ シティ ユニバーシティ オブ ニューヨーク ホスホジエステラーゼ４型を阻害することによって、神経系の再生および修復を刺激するための方法
US6495154B1 (en) * 2000-11-21 2002-12-17 Vivus Inc. On demand administration of clomipramine and salts thereof to treat premature ejaculation
CA2463469A1 (en) 2001-10-16 2003-04-24 Memory Pharmaceuticals Corporation 4-(4-alkoxy-3-hydroxyphenyl)-2-pyrrolidone derivatives as pde-4 inhibitors for the treatment of neurological syndromes
JP2006523710A (ja) 2003-04-16 2006-10-19 メモリー・ファーマシューティカルズ・コーポレイション ホスホジエステラーゼ４インヒビター

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012495A (en) * 1974-03-20 1977-03-15 Schering Aktiengesellschaft 4-(Polyalkoxyphenyl)-2-pyrrolidones
US4219551A (en) * 1978-08-01 1980-08-26 Schering Aktiengesellschaft Aminoalkoxyphenylpyrrolidone antihypertonic agents and use thereof
WO1992019594A1 (en) * 1991-05-02 1992-11-12 Smithkline Beecham Corporation Pyrrolidinones
WO1993007141A1 (en) * 1991-10-11 1993-04-15 Smithkline Beecham Corporation Heterocyclic 3-phenylpyrrolidin-2-ones, their preparation and use for the manufacture of a medicament for inhibiting tumor necrosis factor production
WO1995028926A1 (en) * 1994-04-21 1995-11-02 Schering Aktiengesellschaft Pde iv inhibitors for treating multiple sclerosis

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts abstract accession no.125:151278 (Journal of Chromatography Vol.737(2) (1996) pp 333-337) *
Journal of Medicinal Chemistry Vol.32(7) (1989) pp 1450-1457 *

Also Published As

Publication number Publication date
ATE444065T1 (de) 2009-10-15
RU2004115333A (ru) 2005-10-27
NO20042024L (no) 2004-05-14
ZA200402856B (en) 2005-01-25
MXPA04003516A (es) 2004-07-23
EP1435944B1 (en) 2009-09-30
US20050272803A1 (en) 2005-12-08
US20090176799A1 (en) 2009-07-09
WO2003032981A1 (en) 2003-04-24
NZ532288A (en) 2005-12-23
BR0213660A (pt) 2004-08-24
ES2334650T3 (es) 2010-03-15
CA2463469A1 (en) 2003-04-24
JP4484515B2 (ja) 2010-06-16
AU2002335015B2 (en) 2006-11-02
CN1604776A (zh) 2005-04-06
US20030139406A1 (en) 2003-07-24
CO5570674A2 (es) 2005-10-31
US7235579B2 (en) 2007-06-26
EP1435944A1 (en) 2004-07-14
JP2009286797A (ja) 2009-12-10
IL161317A0 (en) 2004-09-27
KR100951218B1 (ko) 2010-04-05
DE60233884D1 (de) 2009-11-12
JP2005508961A (ja) 2005-04-07
KR20090080573A (ko) 2009-07-24
RU2340600C2 (ru) 2008-12-10
HRP20040409A2 (en) 2005-06-30
KR20050037404A (ko) 2005-04-21
RU2008123376A (ru) 2009-12-27

Similar Documents

Publication Publication Date Title
AU2002335015B2 (en) 4-(4-alkoxy-3-hydroxyphenyl)-2-pyrrolidone derivatives as pde-4 inhibitors for the treatment of neurological syndromes
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
EP1692109B1 (en) Phosphodiesterase 4 inhibitors, including n-substituted diarylamine analogs
US7700631B2 (en) Phosphodiesterase 4 inhibitors
AU2010200233A1 (en) 6-amino-1H-indazole and 4-aminobenzofuran compounds as phosphodiesterase 4 inhibitors
US7153871B2 (en) Phosphodiesterase 4 inhibitors, including aminoindazole and aminobenzofuran analogs
US20060135535A1 (en) Phosphodiesterase 4 inhibitors
MXPA05011055A (en) 4 - (3,4 - disubstituted phenyl) - pyrrolidin-2-one compounds as phosphodiesterase 4 inhibitors

Legal Events

Date Code Title Description
MK13 Application withdrawn section 141(2)/reg 8.3(2) - pct appl. non-entering nat. phase, withdrawn by applicant
TH Corrigenda

Free format text: IN VOL 20, NO 42, PAGE(S) 4176 UNDER THE HEADING APPLICATIONS ACCEPTED - NAME INDEX UNDER THE NAME MEMORY PHARMACEUTICALS CORPORATION, APPLICATION NO. 2002335015, UNDER INID (72), CORRECT THE CO-INVENTOR NAME TO KEUSTER, ERIK

FGA Letters patent sealed or granted (standard patent)
MK14 Patent ceased section 143(a) (annual fees not paid) or expired