CA2004154A1 - 3,5-di-tertiaire-butyl-4-hydroxyphenol-1,3,4-thiadiazoles et oxadiazoles et 3,5-di-tertiaire-butyl-4-hydroxyphenyl 1,2,4-thiadiazoles, oxadiazoles et triazoles agissant comme agents anti-inflammatoires - Google Patents

3,5-di-tertiaire-butyl-4-hydroxyphenol-1,3,4-thiadiazoles et oxadiazoles et 3,5-di-tertiaire-butyl-4-hydroxyphenyl 1,2,4-thiadiazoles, oxadiazoles et triazoles agissant comme agents anti-inflammatoires

Info

Publication number: CA2004154A1
Authority: CA; Canada
Prior art keywords: oxadiazoles; tertiary; butyl; hydroxyphenyl; thiadiazoles
Prior art date: 1988-11-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

CA2004154A

Other languages

English (en)

Other versions

CA2004154C (fr

Inventor

David T. Connor

Catherine R. Kostlan

Michael D. Mullican

Michael W. Wilson

Daniel L. Flynn

Gary P. Shrum

Paul C. Unangst

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.)

Warner Lambert Co LLC

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.)

1988-11-29

Filing date

1989-11-29

Publication date

1990-05-29

1989-11-29 Application filed by Individual filed Critical Individual

1990-05-29 Publication of CA2004154A1 publication Critical patent/CA2004154A1/fr

1997-10-07 Application granted granted Critical

1997-10-07 Publication of CA2004154C publication Critical patent/CA2004154C/fr

2009-11-29 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000004866 oxadiazoles Chemical class 0.000 title abstract 3
RQJGLXIQGUVWKQ-UHFFFAOYSA-N 2,6-ditert-butyl-4-(1,2,4-thiadiazol-3-yl)phenol Chemical class C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C1=NSC=N1 RQJGLXIQGUVWKQ-UHFFFAOYSA-N 0.000 title 1
OCXXMSBMIVRGHO-UHFFFAOYSA-N 2,6-ditert-butyl-4-(1,3,4-thiadiazol-2-yl)phenol Chemical class CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C=2SC=NN=2)=C1 OCXXMSBMIVRGHO-UHFFFAOYSA-N 0.000 title 1
229940121363 anti-inflammatory agent Drugs 0.000 title 1
239000002260 anti-inflammatory agent Substances 0.000 title 1
150000003852 triazoles Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 abstract 2
150000000178 1,2,4-triazoles Chemical class 0.000 abstract 1
-1 3,5-di-tertiary-butyl-4-hydroxyphenyl Chemical group 0.000 abstract 1
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 abstract 1
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 abstract 1
206010061218 Inflammation Diseases 0.000 abstract 1
208000002193 Pain Diseases 0.000 abstract 1
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 abstract 1
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 abstract 1
206010037660 Pyrexia Diseases 0.000 abstract 1
238000007792 addition Methods 0.000 abstract 1
206010003246 arthritis Diseases 0.000 abstract 1
230000004054 inflammatory process Effects 0.000 abstract 1
239000003112 inhibitor Substances 0.000 abstract 1
230000005764 inhibitory process Effects 0.000 abstract 1
238000000034 method Methods 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- 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
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/13—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Plural Heterocyclic Compounds (AREA)

CA002004154A 1988-11-29 1989-11-29 3,5-di-tertiaire-butyl-4-hydroxyphenol-1,3,4-thiadiazoles et oxadiazoles et 3,5-di-tertiaire-butyl-4-hydroxyphenyl 1,2,4-thiadiazoles, oxadiazoles et triazoles agissant comme agents anti-inflammatoires Expired - Fee Related CA2004154C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US27717188A	1988-11-29	1988-11-29
US277,171		1988-11-29
US42681489A	1989-10-30	1989-10-30
US426,814		1989-10-30

Publications (2)

Publication Number	Publication Date
CA2004154A1 true CA2004154A1 (fr)	1990-05-29
CA2004154C CA2004154C (fr)	1997-10-07

Family

ID=26958349

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002004154A Expired - Fee Related CA2004154C (fr)	1988-11-29	1989-11-29	3,5-di-tertiaire-butyl-4-hydroxyphenol-1,3,4-thiadiazoles et oxadiazoles et 3,5-di-tertiaire-butyl-4-hydroxyphenyl 1,2,4-thiadiazoles, oxadiazoles et triazoles agissant comme agents anti-inflammatoires

Country Status (16)

Country	Link
EP (1)	EP0371438B1 (fr)
JP (1)	JP2821208B2 (fr)
KR (1)	KR970004914B1 (fr)
AT (1)	ATE127116T1 (fr)
AU (1)	AU631385B2 (fr)
CA (1)	CA2004154C (fr)
DE (1)	DE68924044T2 (fr)
DK (1)	DK599789A (fr)
ES (1)	ES2075845T3 (fr)
FI (1)	FI93954C (fr)
GR (1)	GR3017688T3 (fr)
IE (1)	IE68850B1 (fr)
NO (1)	NO178623C (fr)
NZ (1)	NZ231534A (fr)
PH (1)	PH27025A (fr)
PT (1)	PT92451B (fr)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5102897A (en) *	1990-03-27	1992-04-07	Warner-Lambert Company	3,5-ditertiarybutyl-4-hydroxyphenyl, 1,3,4-thiadiazoles and oxadiazoles linked by carbon, oxygen, and sulfur residues
US5143929A (en) *	1991-05-09	1992-09-01	Warner-Lambert Company	2-substituted thiazolidinone, oxazolidinone, and imidazolidinone derivatives of fenamates as antiinflammatory agents
US5114958A (en) *	1991-05-09	1992-05-19	Warner-Lambert Company	1,2,4-oxadiazole and 1,2,4-thiadiazole derivatives of fenamates as antiinflammatory agents
DK0595546T3 (da) *	1992-10-28	1996-04-15	Shionogi & Co	Benzylidenderivater
FI951367A7 (fi) *	1994-03-28	1995-09-29	Japan Energy Corp	Puriinijohdannaiset ja tulehdustautien tukahduttajat (suppressantit)
EP0722729A3 (fr) *	1995-01-23	1997-11-26	Eli Lilly And Company	Rhodanines aryl-substituées pour le traitement de la sclérose multiple
AU9802198A (en) *	1997-10-21	1999-05-10	Pharmacia & Upjohn Company	Antiinflammatory thiadiazolyl ureas which act as lfa-1 and mac-1 inhibitors
US6730700B2 (en)	1998-12-02	2004-05-04	Renovis, Inc.	3,4,5,-trisubstituted aryl nitrone compounds and pharmaceutical compositions containing the same
UA66401C2 (en)	1998-12-02	2004-05-17	Sentor Pharmaceuticals Inc	3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical composition containing the same
US6492527B1 (en) *	1999-10-13	2002-12-10	Fmc Corporation	Process to prepare aryltriazolinones and novel intermediates thereto
EP1440968A1 (fr) *	1999-10-13	2004-07-28	Fmc Corporation	Procédé de preparation d'aryltriazolinones et de leurs nouveaux intermediaires
SE0301232D0 (sv) *	2003-04-25	2003-04-25	Astrazeneca Ab	Novel use
WO2006103345A1 (fr) *	2005-04-01	2006-10-05	Galderma Research & Development	Inhibiteurs de la tyrosinase et leur utilisation pour traiter les desordres hyperpigmentaires
FR2883745A1 (fr) *	2005-04-01	2006-10-06	Galderma Res & Dev	Nouveaux inhibiteurs de la tyrosinase et leur utilisation en medecine humaine ainsi qu'en cosmetique
FR2883875A1 (fr) *	2005-04-01	2006-10-06	Galderma Res & Dev	Nouveaux inhibiteurs de la tyrosinase, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique
WO2006103119A2 (fr) *	2005-04-01	2006-10-05	Galderma Research & Development	Nouveaux inhibiteurs de la tyrosinase, leur procede de preparation et leur utilisation dans des medicaments administrables aux hommes et aussi dans les cosmetiques
DE102008038220A1 (de) *	2008-08-18	2010-02-25	Merck Patent Gmbh	Oxadiazolderivate
WO2011028651A1 (fr) *	2009-09-01	2011-03-10	The United States Of America, As Represented By The Secretary, Department Of Health And Human Services	Inhibiteurs de la 15-lipoxygénase-1 humaine
US8580805B2 (en) *	2010-08-31	2013-11-12	Hubert Maehr	Pyrimidine carboxamide derivatives
CN103102348B (zh)	2011-11-14	2016-06-08	上海交通大学	噁二唑类化合物及其制备方法、药物组合物及其用途
CL2012003253A1 (es) *	2012-11-22	2013-01-11	Univ Concepcion	Compuestos derivados de 1,3,4-tiadiazol alquilamidas y de chalconas, antagonistas del receptor trpv-1; uso de los compuestos para tratar el dolor cronico.
GB201810092D0 (en)	2018-06-20	2018-08-08	Ctxt Pty Ltd	Compounds
GB201810581D0 (en)	2018-06-28	2018-08-15	Ctxt Pty Ltd	Compounds
WO2020254946A1 (fr)	2019-06-18	2020-12-24	Pfizer Inc.	Dérivés de benzisoxazole sulfonamide

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2215949B1 (fr) *	1973-02-01	1976-07-02	Delalande Sa
US4212970A (en) *	1977-11-28	1980-07-15	Fuji Photo Film Co., Ltd.	2-Halomethyl-5-vinyl-1,3,4-oxadiazole compounds
JPS58150576A (ja) *	1982-03-03	1983-09-07	Sumitomo Chem Co Ltd	新規な１，２，４−オキサジアゾ−ル誘導体
DE3302120A1 (de) *	1983-01-22	1984-07-26	Bayer Ag, 5090 Leverkusen	(+)-antipode des (e)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ens
PT83152B (pt) *	1985-08-09	1989-03-30	Lilly Co Eli	Processo para a preparacao de compostos di-t-butilfenoicos
US4743606A (en) *	1986-03-25	1988-05-10	Boehringer Ingelheim Pharmaceuticals, Inc.	3-[2-(3',5'-di-t-butyl-4'-hydroxyphenyl)ethenyl]pyridine having anti-inflammatory and anti-arthritic properties
US4758578A (en) *	1987-01-29	1988-07-19	Hoechst Roussel Pharmaceuticals, Inc.	Arylthiadiazolylsulfonamides, pharmaceutical compositions and use
JPH03501731A (ja) *	1987-12-31	1991-04-18	スミスクライン・ベックマン・コーポレイション	４‐アラルキル‐５‐置換‐１，２，４‐トリアゾール‐５‐チオール類

1989
- 1989-11-27 NZ NZ231534A patent/NZ231534A/en unknown
- 1989-11-27 FI FI895669A patent/FI93954C/fi not_active IP Right Cessation
- 1989-11-28 IE IE378589A patent/IE68850B1/en not_active IP Right Cessation
- 1989-11-28 KR KR1019890017310A patent/KR970004914B1/ko not_active Expired - Fee Related
- 1989-11-28 EP EP89121896A patent/EP0371438B1/fr not_active Expired - Lifetime
- 1989-11-28 PH PH39605A patent/PH27025A/en unknown
- 1989-11-28 DK DK599789A patent/DK599789A/da not_active Application Discontinuation
- 1989-11-28 AT AT89121896T patent/ATE127116T1/de not_active IP Right Cessation
- 1989-11-28 ES ES89121896T patent/ES2075845T3/es not_active Expired - Lifetime
- 1989-11-28 DE DE68924044T patent/DE68924044T2/de not_active Expired - Fee Related
- 1989-11-28 JP JP1306789A patent/JP2821208B2/ja not_active Expired - Fee Related
- 1989-11-28 AU AU45625/89A patent/AU631385B2/en not_active Ceased
- 1989-11-28 NO NO894742A patent/NO178623C/no unknown
- 1989-11-29 CA CA002004154A patent/CA2004154C/fr not_active Expired - Fee Related
- 1989-11-29 PT PT92451A patent/PT92451B/pt not_active IP Right Cessation
1995
- 1995-10-11 GR GR950402793T patent/GR3017688T3/el unknown

Also Published As

Publication number	Publication date
AU4562589A (en)	1990-06-21
IE68850B1 (en)	1996-07-24
DE68924044D1 (de)	1995-10-05
NO894742L (no)	1990-05-30
EP0371438B1 (fr)	1995-08-30
IE893785L (en)	1990-05-29
DE68924044T2 (de)	1996-02-15
AU631385B2 (en)	1992-11-26
FI93954C (fi)	1995-06-26
GR3017688T3 (en)	1996-01-31
JP2821208B2 (ja)	1998-11-05
NZ231534A (en)	1992-02-25
PH27025A (en)	1993-02-01
NO178623B (no)	1996-01-22
DK599789A (da)	1990-05-30
JPH02270865A (ja)	1990-11-05
EP0371438A3 (fr)	1991-03-27
ES2075845T3 (es)	1995-10-16
KR970004914B1 (ko)	1997-04-08
PT92451A (pt)	1990-05-31
NO178623C (no)	1996-05-02
KR900007818A (ko)	1990-06-02
DK599789D0 (da)	1989-11-28
FI93954B (fi)	1995-03-15
FI895669A0 (fi)	1989-11-27
PT92451B (pt)	1995-07-18
NO894742D0 (no)	1989-11-28
CA2004154C (fr)	1997-10-07
EP0371438A2 (fr)	1990-06-06
ATE127116T1 (de)	1995-09-15

Legal Events

Date	Code	Title	Description
1996-01-29	EEER	Examination request
2005-11-29	MKLA	Lapsed

Publication	Publication Date	Title
CA2004154A1 (fr)	1990-05-29	3,5-di-tertiaire-butyl-4-hydroxyphenol-1,3,4-thiadiazoles et oxadiazoles et 3,5-di-tertiaire-butyl-4-hydroxyphenyl 1,2,4-thiadiazoles, oxadiazoles et triazoles agissant comme agents anti-inflammatoires
IE940525L (en)	1989-11-25	Known and selected novel arylmethylenyl derivatives of¹thiazolidinones, imidazolidinones and oxazolidinones useful¹as antiallergy agents and antiinflammatory agents
GR3023537T3 (en)	1997-08-29	Inhibition of thrombin.
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