CA2393749C - Substituted 8-arylquinoline phosphodiesterase-4 inhibitors - Google Patents

Substituted 8-arylquinoline phosphodiesterase-4 inhibitors Download PDF

Info

Publication number: CA2393749C
Authority: CA; Canada
Prior art keywords: c6alkyl; phenyl; methylsulfonyl; aryl; alkyl
Prior art date: 1999-12-22
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.): Expired - Fee Related

Application number

CA002393749A

Other languages

English (en)

French (fr)

Other versions

CA2393749A1 (en

Inventor

Denis Deschenes

Daniel Dube

Michel Gallant

Yves Girard

Patrick Lacombe

Dwight Macdonald

Anthony Mastracchio

Helene Perrier

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.)

Merck Canada Inc

Original Assignee

Merck Frosst Canada Ltd

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.)

1999-12-22

Filing date

2000-12-20

Publication date

2008-06-17

2000-12-20 Application filed by Merck Frosst Canada Ltd filed Critical Merck Frosst Canada Ltd

2001-06-28 Publication of CA2393749A1 publication Critical patent/CA2393749A1/en

2008-06-17 Application granted granted Critical

2008-06-17 Publication of CA2393749C publication Critical patent/CA2393749C/en

2020-12-20 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Classifications

- 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
- C07D401/10—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 carbon chain containing aromatic rings
- 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
- A61P11/16—Central respiratory analeptics
- 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
- A61P17/04—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
- 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
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
- 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
- C07D401/14—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 three or more hetero rings
- 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
- C07D409/10—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 aromatic rings
- 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
- C07D413/10—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 carbon chain containing aromatic rings
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- 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
- C07D417/10—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 aromatic rings
- 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
- 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
- C07D417/14—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 three or more hetero rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Dermatology (AREA)
Diabetes (AREA)
Biomedical Technology (AREA)
Heart & Thoracic Surgery (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pain & Pain Management (AREA)
Neurology (AREA)
Urology & Nephrology (AREA)
Neurosurgery (AREA)
Cardiology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA002393749A 1999-12-22 2000-12-20 Substituted 8-arylquinoline phosphodiesterase-4 inhibitors Expired - Fee Related CA2393749C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US17152299P	1999-12-22	1999-12-22
US60/171,522		1999-12-22
PCT/CA2000/001559 WO2001046151A1 (en)	1999-12-22	2000-12-20	Substituted 8-arylquinoline phosphodiesterase-4 inhibitors

Publications (2)

Publication Number	Publication Date
CA2393749A1 CA2393749A1 (en)	2001-06-28
CA2393749C true CA2393749C (en)	2008-06-17

Family

ID=22624050

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002393749A Expired - Fee Related CA2393749C (en)	1999-12-22	2000-12-20	Substituted 8-arylquinoline phosphodiesterase-4 inhibitors

Country Status (31)

Country	Link
EP (1)	EP1244628A1 (es)
JP (1)	JP3782011B2 (es)
KR (1)	KR20020082839A (es)
CN (1)	CN1221534C (es)
AR (1)	AR029214A1 (es)
AU (1)	AU778531B2 (es)
BG (1)	BG65403B1 (es)
BR (1)	BR0016651A (es)
CA (1)	CA2393749C (es)
CO (1)	CO5261613A1 (es)
CZ (1)	CZ20022171A3 (es)
DZ (1)	DZ3244A1 (es)
EA (1)	EA004747B1 (es)
EE (1)	EE200200342A (es)
GE (1)	GEP20053626B (es)
HR (1)	HRP20020545A2 (es)
HU (1)	HUP0203896A3 (es)
IL (1)	IL150114A0 (es)
IS (1)	IS6413A (es)
MX (1)	MXPA02006329A (es)
MY (1)	MY134008A (es)
NO (1)	NO20023013L (es)
NZ (1)	NZ520258A (es)
PE (1)	PE20010989A1 (es)
PL (1)	PL355752A1 (es)
SK (1)	SK8972002A3 (es)
TW (1)	TWI280240B (es)
UA (1)	UA74815C2 (es)
WO (1)	WO2001046151A1 (es)
YU (1)	YU47102A (es)
ZA (1)	ZA200204862B (es)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10110772A1 (de) *	2001-03-07	2002-09-12	Boehringer Ingelheim Pharma	Neue Arzneimittelkompositionen auf der Basis von Anticholinergika und PDE-IV-Inhibitoren
US7776315B2 (en)	2000-10-31	2010-08-17	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Pharmaceutical compositions based on anticholinergics and additional active ingredients
NZ526143A (en) *	2000-12-20	2004-05-28	Merck & Co Inc	Process for making substituted 8-arylquinolinium benzenesulfonate
US6740666B2 (en) *	2000-12-20	2004-05-25	Merck & Co., Inc.	Substituted 8-arylquinoline phosphodiesterase-4 inhibitors
ES2242036T3 (es)	2001-06-27	2005-11-01	MERCK FROSST CANADA & CO.	Inhibidores pde4 de arilquinolina 8-sustituida.
US7009055B2 (en) *	2001-07-24	2006-03-07	Merck & Co., Inc.	Preparation of Sulfonyl quinoline
WO2003024488A2 (en) *	2001-09-19	2003-03-27	Altana Pharma Ag	Combination of a pde inhibitor and a leukotriene receptor antagonist
US7144896B2 (en)	2002-03-18	2006-12-05	Merck Frosst Canada Ltd.	Hetero-bridge substituted 8-arylquinoline pde4 inhibitors
MXPA05009434A (es) *	2003-03-05	2005-11-23	Celgene Corp	Compuestos de difeniletileno y usos de los mismos.
CA2560895A1 (en) *	2004-03-25	2005-10-06	Synta Pharmaceuticals Corp.	Acrylonitrile derivatives for inflammation and immune-related uses
EP1888776A4 (en) *	2005-05-19	2009-07-29	Synergenz Bioscience Ltd	METHODS AND COMPOSITIONS FOR ASSESSING FUNCTION AND PULMONARY DISORDERS
CN102772411A (zh)	2006-07-05	2012-11-14	奈科明有限责任公司	用于治疗炎症性肺部疾病的HMG-CoA还原酶抑制剂与磷酸二酯酶4抑制剂的组合
CA2657093A1 (en) *	2006-07-07	2008-01-10	Steven P. Govek	Bicyclic heteroaryl inhibitors of pde4
EP2076288A2 (en) *	2006-09-22	2009-07-08	Braincells, Inc.	Combination comprising an hmg-coa reductase inhibitor and a second neurogenic agent for treating a nervous system disorder and increasing neurogenesis
CA2676715A1 (en)	2007-02-12	2008-08-21	Merck & Co., Inc.	Piperazine derivatives for treatment of ad and related conditions
WO2009128057A2 (en)	2008-04-18	2009-10-22	UNIVERSITY COLLEGE DUBLIN, NATIONAL UNIVERSITY OF IRELAND, DUBLIN et al	Psycho-pharmaceuticals
EP2533780B1 (en)	2010-02-12	2017-08-23	AskAt Inc.	5-ht4 receptor agonists for the treatment of dementia
US20140271680A1 (en)	2011-08-12	2014-09-18	Universite Paris-Est Creteil Val De Marne	Methods and pharmaceutical compositions for treatment of pulmonary hypertension
WO2013054153A1 (en)	2011-10-11	2013-04-18	INSERM (Institut National de la Santé et de la Recherche Médicale)	Nutlin compounds for use in he treatment of pulmonary hypertension
EP3676262A4 (en) *	2017-09-03	2021-03-31	Angion Biomedica Corp.	VINYLHETEROCYCLENE AS RHO-ASSOCIATED COILED COIL KINASE (ROCK) INHIBITORS

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9226830D0 (en) *	1992-12-23	1993-02-17	Celltech Ltd	Chemical compounds
US5455252A (en) *	1993-03-31	1995-10-03	Syntex (U.S.A.) Inc.	Optionally substituted 6,8-quinolines
US6245774B1 (en) *	1994-06-21	2001-06-12	Celltech Therapeutics Limited	Tri-substituted phenyl or pyridine derivatives
JPH11209350A (ja) *	1998-01-26	1999-08-03	Eisai Co Ltd	含窒素複素環誘導体およびその医薬

2000
- 2000-12-19 MY MYPI20005965A patent/MY134008A/en unknown
- 2000-12-20 CN CNB00818951XA patent/CN1221534C/zh not_active Expired - Fee Related
- 2000-12-20 JP JP2001547062A patent/JP3782011B2/ja not_active Expired - Fee Related
- 2000-12-20 EE EEP200200342A patent/EE200200342A/xx unknown
- 2000-12-20 CZ CZ20022171A patent/CZ20022171A3/cs unknown
- 2000-12-20 SK SK897-2002A patent/SK8972002A3/sk not_active Application Discontinuation
- 2000-12-20 HR HR20020545A patent/HRP20020545A2/hr not_active Application Discontinuation
- 2000-12-20 BR BR0016651-0A patent/BR0016651A/pt not_active IP Right Cessation
- 2000-12-20 WO PCT/CA2000/001559 patent/WO2001046151A1/en not_active Ceased
- 2000-12-20 HU HU0203896A patent/HUP0203896A3/hu unknown
- 2000-12-20 YU YU47102A patent/YU47102A/sh unknown
- 2000-12-20 GE GE4903A patent/GEP20053626B/en unknown
- 2000-12-20 DZ DZ003244A patent/DZ3244A1/fr active
- 2000-12-20 PL PL00355752A patent/PL355752A1/xx not_active IP Right Cessation
- 2000-12-20 MX MXPA02006329A patent/MXPA02006329A/es not_active Application Discontinuation
- 2000-12-20 CO CO00096650A patent/CO5261613A1/es not_active Application Discontinuation
- 2000-12-20 IL IL15011400A patent/IL150114A0/xx unknown
- 2000-12-20 KR KR1020027008079A patent/KR20020082839A/ko not_active Ceased
- 2000-12-20 NZ NZ520258A patent/NZ520258A/en unknown
- 2000-12-20 CA CA002393749A patent/CA2393749C/en not_active Expired - Fee Related
- 2000-12-20 EA EA200200702A patent/EA004747B1/ru not_active IP Right Cessation
- 2000-12-20 AU AU23362/01A patent/AU778531B2/en not_active Ceased
- 2000-12-20 EP EP00986937A patent/EP1244628A1/en not_active Withdrawn
- 2000-12-20 UA UA2002076108A patent/UA74815C2/uk unknown
- 2000-12-21 AR ARP000106867A patent/AR029214A1/es not_active Application Discontinuation
- 2000-12-21 TW TW089127506A patent/TWI280240B/zh not_active IP Right Cessation
- 2000-12-22 PE PE2000001396A patent/PE20010989A1/es not_active Application Discontinuation
2002
- 2002-06-11 IS IS6413A patent/IS6413A/is unknown
- 2002-06-18 ZA ZA200204862A patent/ZA200204862B/en unknown
- 2002-06-19 BG BG106840A patent/BG65403B1/bg unknown
- 2002-06-21 NO NO20023013A patent/NO20023013L/no unknown

Also Published As

Publication number	Publication date
UA74815C2 (en)	2006-02-15
KR20020082839A (ko)	2002-10-31
WO2001046151A1 (en)	2001-06-28
NO20023013D0 (no)	2002-06-21
AU2336201A (en)	2001-07-03
NO20023013L (no)	2002-08-22
AR029214A1 (es)	2003-06-18
BG106840A (en)	2003-01-31
HUP0203896A2 (hu)	2003-04-28
JP3782011B2 (ja)	2006-06-07
HUP0203896A3 (en)	2003-05-28
YU47102A (sh)	2005-06-10
TWI280240B (en)	2007-05-01
BG65403B1 (bg)	2008-06-30
GEP20053626B (en)	2005-10-10
EA004747B1 (ru)	2004-08-26
EE200200342A (et)	2003-06-16
EP1244628A1 (en)	2002-10-02
HK1057560A1 (en)	2004-04-08
DZ3244A1 (fr)	2001-06-28
AU778531B2 (en)	2004-12-09
IL150114A0 (en)	2002-12-01
MY134008A (en)	2007-11-30
SK8972002A3 (en)	2002-11-06
EA200200702A1 (ru)	2003-02-27
NZ520258A (en)	2004-05-28
CA2393749A1 (en)	2001-06-28
PL355752A1 (en)	2004-05-17
BR0016651A (pt)	2002-09-10
CZ20022171A3 (cs)	2002-11-13
ZA200204862B (en)	2003-03-17
CO5261613A1 (es)	2003-03-31
CN1434801A (zh)	2003-08-06
PE20010989A1 (es)	2001-10-01
HRP20020545A2 (en)	2005-10-31
IS6413A (is)	2002-06-11
MXPA02006329A (es)	2004-05-14
CN1221534C (zh)	2005-10-05
JP2003531112A (ja)	2003-10-21

Publication	Publication Date	Title
CA2393749C (en)	2008-06-17	Substituted 8-arylquinoline phosphodiesterase-4 inhibitors
US6410563B1 (en)	2002-06-25	Substituted 8-arylquinoline phosphodiesterase-4 inhibitors
CA2456817C (en)	2010-11-30	Alkyne-aryl-naphthyridin-4 (1h)-one derivatives as type iv phosphodiesterase inhibitor
AU2001297603B2 (en)	2006-02-16	Substituted 8-arylquinoline phosphodiesterase-4 inhibitors
US20060004056A1 (en)	2006-01-05	Di-aryl-substituted-ethan pyridone pde4 inhibitors
CA2403423C (en)	2010-05-25	Tri-aryl-substituted-ethane pde4 inhibitors
EP1404330B1 (en)	2005-06-01	Substituted 8-arylquinoline pde4 inhibitors
AU2001297603A1 (en)	2003-03-13	Substituted 8-arylquinoline phosphodiesterase-4 inhibitors
AU2002344885A1 (en)	2003-05-15	Substituted 8-arylquinoline PDE4 Inhibitors
US20060223850A1 (en)	2006-10-05	8-(3-Biaryl)phenylquinoline phosphodiesterase-4 inhibitors

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