TWI280240B - Substituted 8-arylquinoline phosphodiesterase-4 inhibitors - Google Patents

Substituted 8-arylquinoline phosphodiesterase-4 inhibitors Download PDF

Info

Publication number: TWI280240B
Authority: TW; Taiwan
Prior art keywords: alkyl; phenyl; cns; national standard; methyl
Prior art date: 1999-12-22

Application number

TW089127506A

Other languages

English (en)

Chinese (zh)

Inventor

Denis Deschenes

Daniel Dube

Michel Gallant

Yves Girard

Patrick Lacombe

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

2000-12-21

Publication date

2007-05-01

2000-12-21 Application filed by Merck Frosst Canada Ltd filed Critical Merck Frosst Canada Ltd

2007-05-01 Application granted granted Critical

2007-05-01 Publication of TWI280240B publication Critical patent/TWI280240B/zh

Links

239000002587 phosphodiesterase IV inhibitor Substances 0.000 title abstract description 18
125000001424 substituent group Chemical group 0.000 claims abstract description 169
125000003118 aryl group Chemical group 0.000 claims abstract description 144
125000000217 alkyl group Chemical group 0.000 claims description 356
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 171
-1 cyclo-C3-C6 alkyl Chemical group 0.000 claims description 154
150000001875 compounds Chemical class 0.000 claims description 122
125000001072 heteroaryl group Chemical group 0.000 claims description 111
125000003545 alkoxy group Chemical group 0.000 claims description 89
125000004093 cyano group Chemical group *C#N 0.000 claims description 63
229910052736 halogen Inorganic materials 0.000 claims description 63
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 61
150000002367 halogens Chemical class 0.000 claims description 61
150000003839 salts Chemical class 0.000 claims description 58
125000000623 heterocyclic group Chemical group 0.000 claims description 50
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 48
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 47
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 47
150000001412 amines Chemical class 0.000 claims description 38
229920002554 vinyl polymer Polymers 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 22
125000004104 aryloxy group Chemical group 0.000 claims description 21
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125000003277 amino group Chemical group 0.000 claims description 17
230000004054 inflammatory process Effects 0.000 claims description 17
150000002923 oximes Chemical class 0.000 claims description 17
230000000694 effects Effects 0.000 claims description 16
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 15
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
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LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 3
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102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 2
108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
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IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
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239000011593 sulfur Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011030 tanzanite Substances 0.000 description 1
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
125000000101 thioether group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000002103 transcriptional effect Effects 0.000 description 1
230000007704 transition Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Substances C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 1
150000003648 triterpenes Chemical class 0.000 description 1
241000701447 unidentified baculovirus Species 0.000 description 1
239000004474 valine Substances 0.000 description 1
229960003726 vasopressin Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

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- 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
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- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- 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

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

TW089127506A 1999-12-22 2000-12-21 Substituted 8-arylquinoline phosphodiesterase-4 inhibitors TWI280240B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US17152299P	1999-12-22	1999-12-22

Publications (1)

Publication Number	Publication Date
TWI280240B true TWI280240B (en)	2007-05-01

Family

ID=22624050

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW089127506A TWI280240B (en)	1999-12-22	2000-12-21	Substituted 8-arylquinoline phosphodiesterase-4 inhibitors

Country Status (31)

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

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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
US6740666B2 (en) *	2000-12-20	2004-05-25	Merck & Co., Inc.	Substituted 8-arylquinoline phosphodiesterase-4 inhibitors
HRP20030507A2 (en) *	2000-12-20	2005-06-30	Merck & Co. Inc.	Process for making substituted 8-arylquinolinium benzensulfonate
WO2003002118A1 (fr) *	2001-06-27	2003-01-09	Merck Frosst Canada & Co.	Arylquinones inhibiteurs de pde4 a substitution en position 8
WO2003010137A1 (fr) *	2001-07-24	2003-02-06	Merck & Co., Inc.	Preparation de sulfonyl quinoleine
JP2005505570A (ja) *	2001-09-19	2005-02-24	アルタナ　ファルマ　アクチエンゲゼルシャフト	Ｐｄｅ阻害剤及びロイコトリエン受容体拮抗物質の複合薬
EP1487797B1 (fr)	2002-03-18	2009-05-27	Merck Frosst Canada Ltd.	8-arylquinoleine substituee au moyen d'un pont hetero comme inhibiteurs de pde-4
JP2006519874A (ja) *	2003-03-05	2006-08-31	セルジーン・コーポレーション	ジフェニルエチレン化合物およびその使用
WO2005091752A2 (fr) *	2004-03-25	2005-10-06	Synta Pharmaceuticals Corp.	Derives d'acrylonitrile utilises dans le traitement ou la prevention des inflammations et des troubles immunitaires
CA2608158A1 (fr) *	2005-05-19	2006-11-23	Synergenz Bioscience Limited	Methodes et compositions pour evaluation de la fonction et de troubles pulmonaires
ES2443342T3 (es)	2006-07-05	2014-02-19	Takeda Gmbh	Combinación de inhibidor de la HMG-CoA reductasa rosuvastatina con un inhibidor de la fosfodiesterasa 4, tal como roflumilast, roflumilast-N-óxido para el tratamiento de enfermedades pulmonares inflamatorias
CA2657093A1 (fr) *	2006-07-07	2008-01-10	Steven P. Govek	Inhibiteurs de pde4 a base de composes d'heteroaryle bicyclique
EP2076288A2 (fr) *	2006-09-22	2009-07-08	Braincells, Inc.	Combinaison comprenant un inhibiteur de la hmg-coa réductase et un deuxième agent neurogène pour le traitement d'une maladie du system nerveux central et pour augmenter la neurogenèse
CA2676715A1 (fr)	2007-02-12	2008-08-21	Merck & Co., Inc.	Derives de piperazine pour le traitement de la maladie d'alzheimer et des conditions apparentees
EP2291181B9 (fr)	2008-04-18	2013-09-11	University College Dublin National University Of Ireland, Dublin	Utilisation de la captodiamine pour le traitement des symptômes de la dépression
JP6023926B2 (ja)	2010-02-12	2016-11-09	株式会社ＡｓｋＡｔ	認知症治療のための５−ｈｔ４受容体アゴニスト
WO2013024022A1 (fr)	2011-08-12	2013-02-21	INSERM (Institut National de la Santé et de la Recherche Médicale)	Méthodes et compositions pharmaceutiques pour traiter l'hypertension pulmonaire
US20140328893A1 (en)	2011-10-11	2014-11-06	Institut National De La Sante Et De La Recherche Medicale (Inserm)	Nutlin compounds for use in the treatment of pulmonary hypertension
JP2020532551A (ja) *	2017-09-03	2020-11-12	アンジオンバイオメディカコーポレーション	Ｒｈｏ関連コイルドコイルキナーゼ（ＲＯＣＫ）阻害剤としてのビニルヘテロ環

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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
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- 2000-12-20 YU YU47102A patent/YU47102A/sh unknown
- 2000-12-20 CA CA002393749A patent/CA2393749C/fr not_active Expired - Fee Related
- 2000-12-20 HR HR20020545A patent/HRP20020545A2/hr not_active Application Discontinuation
- 2000-12-20 EP EP00986937A patent/EP1244628A1/fr not_active Withdrawn
- 2000-12-20 BR BR0016651-0A patent/BR0016651A/pt not_active IP Right Cessation
- 2000-12-20 HU HU0203896A patent/HUP0203896A3/hu unknown
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- 2000-12-20 WO PCT/CA2000/001559 patent/WO2001046151A1/fr not_active Ceased
- 2000-12-20 DZ DZ003244A patent/DZ3244A1/fr active
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- 2000-12-20 CZ CZ20022171A patent/CZ20022171A3/cs unknown
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- 2000-12-20 GE GE4903A patent/GEP20053626B/en unknown
- 2000-12-21 TW TW089127506A patent/TWI280240B/zh not_active IP Right Cessation
- 2000-12-21 AR ARP000106867A patent/AR029214A1/es not_active Application Discontinuation
- 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
CA2393749C (fr)	2008-06-17
MY134008A (en)	2007-11-30
PE20010989A1 (es)	2001-10-01
DZ3244A1 (fr)	2001-06-28
KR20020082839A (ko)	2002-10-31
NO20023013D0 (no)	2002-06-21
EA200200702A1 (ru)	2003-02-27
EE200200342A (et)	2003-06-16
EA004747B1 (ru)	2004-08-26
CO5261613A1 (es)	2003-03-31
SK8972002A3 (en)	2002-11-06
NZ520258A (en)	2004-05-28
PL355752A1 (en)	2004-05-17
YU47102A (sh)	2005-06-10
IS6413A (is)	2002-06-11
EP1244628A1 (fr)	2002-10-02
CA2393749A1 (fr)	2001-06-28
BG65403B1 (bg)	2008-06-30
BR0016651A (pt)	2002-09-10
CN1221534C (zh)	2005-10-05
MXPA02006329A (es)	2004-05-14
AR029214A1 (es)	2003-06-18
BG106840A (en)	2003-01-31
CZ20022171A3 (cs)	2002-11-13
ZA200204862B (en)	2003-03-17
AU778531B2 (en)	2004-12-09
JP2003531112A (ja)	2003-10-21
HRP20020545A2 (en)	2005-10-31
HUP0203896A2 (hu)	2003-04-28
HK1057560A1 (en)	2004-04-08
HUP0203896A3 (en)	2003-05-28
AU2336201A (en)	2001-07-03
IL150114A0 (en)	2002-12-01
GEP20053626B (en)	2005-10-10
WO2001046151A1 (fr)	2001-06-28
JP3782011B2 (ja)	2006-06-07
UA74815C2 (en)	2006-02-15
CN1434801A (zh)	2003-08-06
NO20023013L (no)	2002-08-22

Legal Events

Date	Code	Title	Description
2017-08-11	MM4A	Annulment or lapse of patent due to non-payment of fees

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