WO1995000501A3 - Phenyl heterocycles as cyclooxygenase-2 inhibitors - Google Patents

Phenyl heterocycles as cyclooxygenase-2 inhibitors

Info

Publication number
WO1995000501A3
WO1995000501A3 PCT/CA1994/000318 CA9400318W WO9500501A3 WO 1995000501 A3 WO1995000501 A3 WO 1995000501A3 CA 9400318 W CA9400318 W CA 9400318W WO 9500501 A3 WO9500501 A3 WO 9500501A3
Authority
WO
WIPO (PCT)
Prior art keywords
cyclooxygenase
inhibitors
phenyl heterocycles
formula
treatment
Prior art date
Application number
PCT/CA1994/000318
Other languages
French (fr)
Other versions
WO1995000501B1 (en
WO1995000501A2 (en
Inventor
Yves Ducharme
Jacques Yves Gauthier
Petpiboon Prasit
Yves Leblanc
Zhaoyin Wang
Serge Leger
Michel Therien
Original Assignee
Merck Frosst Canada Inc
Yves Ducharme
Jacques Yves Gauthier
Petpiboon Prasit
Yves Leblanc
Zhaoyin Wang
Serge Leger
Michel Therien
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26767192&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1995000501(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to KR1019950705562A priority Critical patent/KR100215358B1/en
Priority to AU69674/94A priority patent/AU6967494A/en
Priority to DE69410092T priority patent/DE69410092T2/en
Priority to SI9430145T priority patent/SI0705254T1/en
Priority to DK94918259T priority patent/DK0705254T3/en
Priority to PL94312196A priority patent/PL178203B1/en
Priority to HU9503319A priority patent/HU227913B1/en
Priority to EP94918259A priority patent/EP0705254B1/en
Priority to RO95-02214A priority patent/RO115354B1/en
Priority to SK1502-95A priority patent/SK284114B6/en
Priority to JP7502268A priority patent/JP2977137B2/en
Priority to NZ267386A priority patent/NZ267386A/en
Priority to BR9406979A priority patent/BR9406979A/en
Priority to UA95125420A priority patent/UA48939C2/en
Priority to RU96100763/04A priority patent/RU2131423C1/en
Application filed by Merck Frosst Canada Inc, Yves Ducharme, Jacques Yves Gauthier, Petpiboon Prasit, Yves Leblanc, Zhaoyin Wang, Serge Leger, Michel Therien filed Critical Merck Frosst Canada Inc
Publication of WO1995000501A2 publication Critical patent/WO1995000501A2/en
Publication of WO1995000501A3 publication Critical patent/WO1995000501A3/en
Publication of WO1995000501B1 publication Critical patent/WO1995000501B1/en
Priority to FI956119A priority patent/FI112222B/en
Priority to BG100247A priority patent/BG63161B1/en
Priority to NO955256A priority patent/NO307253B1/en
Priority to FI20012510A priority patent/FI114913B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other 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
    • 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
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • 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
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • 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
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
    • A61P25/28—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
    • 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
    • A61P31/12—Antivirals
    • 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
    • A61P35/00—Antineoplastic 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
    • C07C311/46—Y being a hydrogen or a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
    • C07C311/49—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/26—Radicals substituted by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/58—One oxygen atom, e.g. butenolide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Abstract

The invention encompasses the novel compound of formula (I) useful in the treatment of cyclooxygenase-2 mediated diseases. The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of formula (I).
PCT/CA1994/000318 1993-06-24 1994-06-09 Phenyl heterocycles as cyclooxygenase-2 inhibitors WO1995000501A2 (en)

Priority Applications (19)

Application Number Priority Date Filing Date Title
AU69674/94A AU6967494A (en) 1993-06-24 1994-06-09 Phenyl heterocycles as cyclooxygenase-2 inhibitors
NZ267386A NZ267386A (en) 1993-06-24 1994-06-09 Phenyl substituted heterocycles, preparation and pharmaceutical compositions thereof
JP7502268A JP2977137B2 (en) 1993-06-24 1994-06-09 Phenyl heterocycle as cyclooxygenase-2 inhibitor
SI9430145T SI0705254T1 (en) 1993-06-24 1994-06-09 Phenyl heterocycles as cyclooxygenase-2 inhibitors
DK94918259T DK0705254T3 (en) 1993-06-24 1994-06-09 Phenyl heterocyclic compounds as cyclooxygenase-2 inhibitors
PL94312196A PL178203B1 (en) 1993-06-24 1994-06-09 Heterocyclic phenyl compounds as inhibitors of cyclooxygenase-2
HU9503319A HU227913B1 (en) 1993-06-24 1994-06-09 Phenyl heterocycles as cyclooxygenase-2 inhibitors
EP94918259A EP0705254B1 (en) 1993-06-24 1994-06-09 Phenyl heterocycles as cyclooxygenase-2 inhibitors
RO95-02214A RO115354B1 (en) 1993-06-24 1994-06-09 Phenyl-heterocyclic compounds, processes for preparing said compounds and preparation intermediate, pharmaceutical composition and method for treating an inflamatory disease
BR9406979A BR9406979A (en) 1993-06-24 1994-06-09 Compound, pharmaceutical composition for treating an inflammatory disease susceptible to treatment with a non-steroidal anti-inflammatory agent processes for treating an inflammatory disease and for preparing a pharmaceutically acceptable salt compound use of a non-steroidal anti-inflammatory pharmaceutical composition compound
DE69410092T DE69410092T2 (en) 1993-06-24 1994-06-09 PHENYL HETEROCYCLEN AS CYCLOOXYGENASE-2 INHIBITORS
KR1019950705562A KR100215358B1 (en) 1993-06-24 1994-06-09 Phenyl heterocycles as cyclooxygenase-2 inhibitors
SK1502-95A SK284114B6 (en) 1993-06-24 1994-06-09 Phenyl heterocycles as cyclooxygenase-2 inhibitors
UA95125420A UA48939C2 (en) 1993-06-24 1994-06-09 Disubstituted furanons, methods for synthesis, pharmaceutical composition, method for treating inflammatory disease, intermediate substances
RU96100763/04A RU2131423C1 (en) 1993-06-24 1994-06-09 Disubstituted furanones, thiazoles and pentenones as inhibitors of cyclooxygenase, method of their synthesis, pharmaceutical composition and method of patient treatment
FI956119A FI112222B (en) 1993-06-24 1995-12-19 A process for the preparation of novel therapeutically useful furanone derivatives
BG100247A BG63161B1 (en) 1993-06-24 1995-12-21 Phenylheterocyclic compounds as inhibitors of cyclooxygenase-2
NO955256A NO307253B1 (en) 1993-06-24 1995-12-22 Phenyl heterocycles as cyclooxygenase-2 inhibitors
FI20012510A FI114913B (en) 1993-06-24 2001-12-19 Process for the preparation of therapeutically useful furanone derivatives and a starting material useful in the process

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US8219693A 1993-06-24 1993-06-24
US082,196 1993-06-24
US179,467 1994-01-10
US08/179,467 US5474995A (en) 1993-06-24 1994-01-10 Phenyl heterocycles as cox-2 inhibitors

Publications (3)

Publication Number Publication Date
WO1995000501A2 WO1995000501A2 (en) 1995-01-05
WO1995000501A3 true WO1995000501A3 (en) 1995-04-13
WO1995000501B1 WO1995000501B1 (en) 1995-05-26

Family

ID=26767192

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA1994/000318 WO1995000501A2 (en) 1993-06-24 1994-06-09 Phenyl heterocycles as cyclooxygenase-2 inhibitors

Country Status (36)

Country Link
US (5) US5474995A (en)
EP (4) EP0822190A1 (en)
JP (1) JP2977137B2 (en)
KR (1) KR100215358B1 (en)
CN (2) CN1058008C (en)
AT (1) ATE165825T1 (en)
AU (1) AU6967494A (en)
BG (1) BG63161B1 (en)
BR (1) BR9406979A (en)
CA (5) CA2278241C (en)
CY (1) CY2098B1 (en)
CZ (1) CZ288175B6 (en)
DE (1) DE69410092T2 (en)
DK (1) DK0705254T3 (en)
ES (1) ES2115237T3 (en)
FI (2) FI112222B (en)
HK (1) HK1027474A1 (en)
HR (1) HRP940373A2 (en)
HU (1) HU227913B1 (en)
IL (3) IL110031A (en)
LV (1) LV12209B (en)
MX (1) MX9404749A (en)
NO (1) NO307253B1 (en)
NZ (1) NZ267386A (en)
PL (1) PL178203B1 (en)
RO (1) RO115354B1 (en)
RU (1) RU2131423C1 (en)
SA (1) SA94150039B1 (en)
SG (1) SG52703A1 (en)
SI (1) SI0705254T1 (en)
SK (1) SK284114B6 (en)
TW (1) TW326042B (en)
UA (1) UA48939C2 (en)
WO (1) WO1995000501A2 (en)
YU (1) YU49053B (en)
ZA (1) ZA944501B (en)

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DK0679157T3 (en) * 1993-01-15 1998-07-27 Searle & Co Novel 3,4-diarylthiophenes and analogs thereof for use as anti-inflammatory agents
GB9420616D0 (en) * 1994-10-12 1994-11-30 Merck Sharp & Dohme Method, compositions and use
US6090834A (en) * 1993-05-21 2000-07-18 G.D. Searle & Co. Substituted oxazoles for the treatment of inflammation
US5840746A (en) * 1993-06-24 1998-11-24 Merck Frosst Canada, Inc. Use of inhibitors of cyclooxygenase in the treatment of neurodegenerative diseases
US5474995A (en) * 1993-06-24 1995-12-12 Merck Frosst Canada, Inc. Phenyl heterocycles as cox-2 inhibitors
GB9602877D0 (en) * 1996-02-13 1996-04-10 Merck Frosst Canada Inc 3,4-Diaryl-2-hydroxy-2,5- dihydrofurans as prodrugs to cox-2 inhibitors
EP0739340A1 (en) * 1994-01-10 1996-10-30 Merck Frosst Canada Inc. Phenyl heterocycles as cox-2 inhibitors
JPH10504542A (en) * 1994-07-27 1998-05-06 ジー．ディー．サール アンド カンパニー Substituted thiazole compounds for treating inflammation
US6613789B2 (en) 1994-07-28 2003-09-02 G. D. Searle & Co. Heterocyclo-substituted imidazoles for the treatment of inflammation
US6426360B1 (en) * 1994-07-28 2002-07-30 G D Searle & Co. 4,5-substituted imidazolyl compounds for the treatment of inflammation
US5620999A (en) * 1994-07-28 1997-04-15 Weier; Richard M. Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation
US5616601A (en) * 1994-07-28 1997-04-01 Gd Searle & Co 1,2-aryl and heteroaryl substituted imidazolyl compounds for the treatment of inflammation
US6239172B1 (en) * 1997-04-10 2001-05-29 Nitrosystems, Inc. Formulations for treating disease and methods of using same
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