CA2180651A1 - Phenyl heterocycles as cox-2 inhibitors - Google Patents

Phenyl heterocycles as cox-2 inhibitors

Info

Publication number: CA2180651A1
Authority: CA; Canada
Prior art keywords: phenyl; furanone; methylsulfonyl; pharmaceutically acceptable; so2me
Prior art date: 1994-01-10
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.): Abandoned

Application number

CA002180651A

Other languages

English (en)

French (fr)

Inventor

Yves Ducharme

Jacques Yves Gauthier

Petpiboon Prasit

Yves Leblanc

Zhaoyin Wang

Serge Leger

Michel Therien

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 Frosst Canada and Co

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.)

1994-01-10

Filing date

1994-12-19

Publication date

1995-07-13

1994-01-10 Priority claimed from US08/179,467 external-priority patent/US5474995A/en

1994-12-19 Application filed by Individual filed Critical Individual

1995-07-13 Publication of CA2180651A1 publication Critical patent/CA2180651A1/en

Status Abandoned legal-status Critical Current

Links

229940111134 coxibs Drugs 0.000 title claims 2
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims abstract description 43
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
201000010099 disease Diseases 0.000 claims abstract description 20
230000001404 mediated effect Effects 0.000 claims abstract description 18
239000008194 pharmaceutical composition Substances 0.000 claims abstract 5
238000000034 method Methods 0.000 claims description 49
102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims description 25
108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 20
231100000252 nontoxic Toxicity 0.000 claims description 15
230000003000 nontoxic effect Effects 0.000 claims description 15
239000003814 drug Substances 0.000 claims description 9
102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 claims description 8
108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 claims description 8
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 8
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 8
239000013543 active substance Substances 0.000 claims description 6
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 5
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 5
230000003637 steroidlike Effects 0.000 claims description 5
RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims 5
208000027866 inflammatory disease Diseases 0.000 claims 4
230000003110 anti-inflammatory effect Effects 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
AXEQBWLOHGSVAY-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-4-[4-(trifluoromethyl)phenyl]-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(=CC=2)C(F)(F)F)C(=O)OC1 AXEQBWLOHGSVAY-UHFFFAOYSA-N 0.000 claims 1
CVLFUMMNMNBFTN-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-4-naphthalen-2-yl-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C3C=CC=CC3=CC=2)C(=O)OC1 CVLFUMMNMNBFTN-UHFFFAOYSA-N 0.000 claims 1
PTQHWLGWYIZMPG-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-4-quinolin-7-yl-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C3N=CC=CC3=CC=2)C(=O)OC1 PTQHWLGWYIZMPG-UHFFFAOYSA-N 0.000 claims 1
WIQUDZWQAGMVCZ-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC1 WIQUDZWQAGMVCZ-UHFFFAOYSA-N 0.000 claims 1
LORWTWIEUJJMCM-UHFFFAOYSA-N 4-(2,4-difluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC(F)=CC=2)F)C(=O)OC1 LORWTWIEUJJMCM-UHFFFAOYSA-N 0.000 claims 1
ARCSOGMAFZFYCW-UHFFFAOYSA-N 4-(2,5-difluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC=C(F)C=2)F)C(=O)OC1 ARCSOGMAFZFYCW-UHFFFAOYSA-N 0.000 claims 1
WMFRRLNDIBTRFS-UHFFFAOYSA-N 4-(2,6-dichlorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC=CC=2Cl)Cl)C(=O)OC1 WMFRRLNDIBTRFS-UHFFFAOYSA-N 0.000 claims 1
MBASHDZRFLLCIV-UHFFFAOYSA-N 4-(2,6-difluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC=CC=2F)F)C(=O)OC1 MBASHDZRFLLCIV-UHFFFAOYSA-N 0.000 claims 1
LEQFUZZMGBGNLQ-UHFFFAOYSA-N 4-(2-bromo-4-chlorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC(Cl)=CC=2)Br)C(=O)OC1 LEQFUZZMGBGNLQ-UHFFFAOYSA-N 0.000 claims 1
HZJOTAJACQZHEM-UHFFFAOYSA-N 4-(2-bromo-4-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC(F)=CC=2)Br)C(=O)OC1 HZJOTAJACQZHEM-UHFFFAOYSA-N 0.000 claims 1
NYXCNJHNJVUQGE-UHFFFAOYSA-N 4-(2-chloro-6-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC=CC=2F)Cl)C(=O)OC1 NYXCNJHNJVUQGE-UHFFFAOYSA-N 0.000 claims 1
FPGNJXJYBXKRBP-UHFFFAOYSA-N 4-(2-chlorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)C(=O)OC1 FPGNJXJYBXKRBP-UHFFFAOYSA-N 0.000 claims 1
RHCSULRRWTXBKR-UHFFFAOYSA-N 4-(2-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC=CC=2)F)C(=O)OC1 RHCSULRRWTXBKR-UHFFFAOYSA-N 0.000 claims 1
BTDBERSXBWFFFV-UHFFFAOYSA-N 4-(3,4-dibromophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(Br)C(Br)=CC=2)C(=O)OC1 BTDBERSXBWFFFV-UHFFFAOYSA-N 0.000 claims 1
ZGXGYHUSQXJPID-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(Cl)C(Cl)=CC=2)C(=O)OC1 ZGXGYHUSQXJPID-UHFFFAOYSA-N 0.000 claims 1
INRQTVDUZFESAO-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C(F)=CC=2)C(=O)OC1 INRQTVDUZFESAO-UHFFFAOYSA-N 0.000 claims 1
HYYVKBRPWKEEDA-UHFFFAOYSA-N 4-(3,5-difluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C=C(F)C=2)C(=O)OC1 HYYVKBRPWKEEDA-UHFFFAOYSA-N 0.000 claims 1
LRJMZDORYWOBDJ-UHFFFAOYSA-N 4-(3-bromo-4-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(Br)C(F)=CC=2)C(=O)OC1 LRJMZDORYWOBDJ-UHFFFAOYSA-N 0.000 claims 1
CKPIJHKGXVWGJT-UHFFFAOYSA-N 4-(3-bromo-4-methoxyphenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=C(Br)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)COC1=O CKPIJHKGXVWGJT-UHFFFAOYSA-N 0.000 claims 1
FMUHIKZFYFQQDB-UHFFFAOYSA-N 4-(3-bromo-4-methylphenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=C(Br)C(C)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)COC1=O FMUHIKZFYFQQDB-UHFFFAOYSA-N 0.000 claims 1
GOXAQESCHCROMJ-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(Cl)C(F)=CC=2)C(=O)OC1 GOXAQESCHCROMJ-UHFFFAOYSA-N 0.000 claims 1
ABWDZOORJGAOPO-UHFFFAOYSA-N 4-(3-chloro-4-methoxyphenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)COC1=O ABWDZOORJGAOPO-UHFFFAOYSA-N 0.000 claims 1
RZAMGHPKLSEGAD-UHFFFAOYSA-N 4-(3-chlorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(Cl)C=CC=2)C(=O)OC1 RZAMGHPKLSEGAD-UHFFFAOYSA-N 0.000 claims 1
MISOJLQZKVLGMN-UHFFFAOYSA-N 4-(3-fluoro-4-methoxyphenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)COC1=O MISOJLQZKVLGMN-UHFFFAOYSA-N 0.000 claims 1
KZNGNTKISMAXAG-UHFFFAOYSA-N 4-(3-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C=CC=2)C(=O)OC1 KZNGNTKISMAXAG-UHFFFAOYSA-N 0.000 claims 1
GLINWVYVGCKZPP-UHFFFAOYSA-N 4-(4-bromo-2-chlorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC(Br)=CC=2)Cl)C(=O)OC1 GLINWVYVGCKZPP-UHFFFAOYSA-N 0.000 claims 1
DKFBOFPVCWDYHN-UHFFFAOYSA-N 4-(4-bromo-2-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC(Br)=CC=2)F)C(=O)OC1 DKFBOFPVCWDYHN-UHFFFAOYSA-N 0.000 claims 1
ZOZVHIIYFMNPMN-UHFFFAOYSA-N 4-(4-bromo-3-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C(Br)=CC=2)C(=O)OC1 ZOZVHIIYFMNPMN-UHFFFAOYSA-N 0.000 claims 1
SFHMGRIAFWNSKU-UHFFFAOYSA-N 4-(4-bromophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Br)=CC=2)C(=O)OC1 SFHMGRIAFWNSKU-UHFFFAOYSA-N 0.000 claims 1
CDPWDFXNZHNECF-UHFFFAOYSA-N 4-(4-chloro-2-fluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC(Cl)=CC=2)F)C(=O)OC1 CDPWDFXNZHNECF-UHFFFAOYSA-N 0.000 claims 1
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WCNUKLPROMYSTR-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)COC1=O WCNUKLPROMYSTR-UHFFFAOYSA-N 0.000 claims 1
DTWFXKJRKRRIPH-UHFFFAOYSA-N 4-(4-methylsulfanylphenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)COC1=O DTWFXKJRKRRIPH-UHFFFAOYSA-N 0.000 claims 1
LQDZIMSKYUVVHN-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenyl)-5-oxo-2h-furan-3-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=C(Cl)C(Cl)=CC=2)C(=O)OC1 LQDZIMSKYUVVHN-UHFFFAOYSA-N 0.000 claims 1
KNXSHYYXBCTDAC-UHFFFAOYSA-N 4-[4-(3,4-difluorophenyl)-5-oxo-2h-furan-3-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=C(F)C(F)=CC=2)C(=O)OC1 KNXSHYYXBCTDAC-UHFFFAOYSA-N 0.000 claims 1
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LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)

CA002180651A 1994-01-10 1994-12-19 Phenyl heterocycles as cox-2 inhibitors Abandoned CA2180651A1 (en)

Applications Claiming Priority (2)

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

Publications (1)

Publication Number	Publication Date
CA2180651A1 true CA2180651A1 (en)	1995-07-13

Family

ID=22656713

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002180651A Abandoned CA2180651A1 (en)	1994-01-10	1994-12-19	Phenyl heterocycles as cox-2 inhibitors

Country Status (12)

Country	Link
EP (1)	EP0739340A1 (fi)
JP (1)	JP2788677B2 (fi)
CN (1)	CN1143365A (fi)
AU (1)	AU1269495A (fi)
BG (1)	BG63082B1 (fi)
BR (1)	BR9408478A (fi)
CA (1)	CA2180651A1 (fi)
FI (1)	FI108792B (fi)
HU (1)	HUT74986A (fi)
NO (1)	NO960393L (fi)
SG (1)	SG43841A1 (fi)
WO (1)	WO1995018799A1 (fi)

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AU775030B2 (en) *	1996-05-17	2004-07-15	Merck Frosst Company	Compositions for a once a day treatment of cyclooxygenase-2 mediated diseases
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GB9615867D0 (en) *	1996-07-03	1996-09-11	Merck & Co Inc	Process of preparing phenyl heterocycles useful as cox-2 inhibitors
US5939069A (en) *	1996-08-23	1999-08-17	University Of Florida	Materials and methods for detection and treatment of immune system dysfunctions
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US6887893B1 (en)	1997-12-24	2005-05-03	Sankyo Company, Limited	Methods and compositions for treatment and prevention of tumors, tumor-related disorders and cachexia
SA99191255B1 (ar)	1998-11-30	2006-11-25	جي دي سيرل اند كو	مركبات سيليكوكسيب celecoxib
CA2398995C (en)	2000-02-04	2014-09-23	Children's Hospital Research Foundation	Lipid hydrolysis therapy for atherosclerosis and related diseases
US6465509B2 (en) *	2000-06-30	2002-10-15	Merck Frosst Canada & Co.	Pyrones as inhibitors of cyclooxygenase-2
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PT3072978T (pt)	2002-05-09	2018-10-15	Brigham & Womens Hospital Inc	1l1rl-1 como um marcador de doença cardiovascular
WO2004002409A2 (en)	2002-06-27	2004-01-08	Nitromed, Inc.	Cyclooxygenase-2 selective inhibitors, compositions and methods of use
HUE027546T2 (en)	2003-08-29	2016-10-28	Brigham & Womens Hospital Inc	Hydantoin derivatives as cell necrosis inhibitors
KR20050051729A (ko) *	2003-11-28	2005-06-02	일양약품주식회사	사이클로 옥시게나제-2 억제제인 페닐 헤테로사이클의제조방법
DE102004027912A1 (de)	2004-06-09	2005-12-29	Grünenthal GmbH	Substituierte Cyclopenten-Verbindungen
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CN102317786A (zh)	2007-04-18	2012-01-11	特提斯生物科学公司	糖尿病相关性生物学标记物及其使用方法
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1994
- 1994-12-19 EP EP95903727A patent/EP0739340A1/en not_active Withdrawn
- 1994-12-19 BR BR9408478A patent/BR9408478A/pt not_active Application Discontinuation
- 1994-12-19 WO PCT/CA1994/000688 patent/WO1995018799A1/en not_active Ceased
- 1994-12-19 AU AU12694/95A patent/AU1269495A/en not_active Abandoned
- 1994-12-19 SG SG1996002006A patent/SG43841A1/en unknown
- 1994-12-19 CN CN94195045A patent/CN1143365A/zh active Pending
- 1994-12-19 CA CA002180651A patent/CA2180651A1/en not_active Abandoned
- 1994-12-19 HU HU9601875A patent/HUT74986A/hu not_active Application Discontinuation
- 1994-12-19 JP JP7518234A patent/JP2788677B2/ja not_active Expired - Fee Related
1996
- 1996-01-30 NO NO960393A patent/NO960393L/no not_active Application Discontinuation
- 1996-02-12 BG BG100350A patent/BG63082B1/bg unknown
- 1996-07-09 FI FI962800A patent/FI108792B/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
NO960393L (no)	1996-07-09
BR9408478A (pt)	1997-08-26
JP2788677B2 (ja)	1998-08-20
WO1995018799A1 (en)	1995-07-13
EP0739340A1 (en)	1996-10-30
JPH09506631A (ja)	1997-06-30
BG63082B1 (bg)	2001-03-30
BG100350A (bg)	1996-12-31
HUT74986A (en)	1997-03-28
AU1269495A (en)	1995-08-01
FI962800L (fi)	1996-09-06
HU9601875D0 (en)	1996-09-30
SG43841A1 (en)	1997-11-14
CN1143365A (zh)	1997-02-19
FI962800A0 (fi)	1996-07-09
FI108792B (fi)	2002-03-28
NO960393D0 (no)	1996-01-30

Publication	Publication Date	Title
CA2180651A1 (en)	1995-07-13	Phenyl heterocycles as cox-2 inhibitors
US6239173B1 (en)	2001-05-29	3-phenyl-4-(4(methylsulfonyl)phenyl)-2-(5H)-furanone as a cox-2 inhibitor
EP0778834B1 (en)	2000-01-26	Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2
HK1027474B (en)	2001-01-12	Phenyl heterocycles as cyclooxygenase-2 inhibitors
CA2206978A1 (en)	1996-06-27	Diaryl-2-(5h)-furanones as cox-2 inhibitors
AU706518B2 (en)	1999-06-17	Bisarylcyclobutene derivates as cyclooxygenase inhibitors
WO1997028121A1 (en)	1997-08-07	Alkylated styrenes as prodrugs to cox-2 inhibitors
JP3490406B2 (ja)	2004-01-26	シクロオキシゲナーゼ−２阻害剤としてのフェニルヘテロ環
CA2244140C (en)	2006-03-21	Alkylated styrenes as prodrugs to cox-2 inhibitors
HK1027344A (en)	2001-01-12	Phenyl heterocycles as cyclooxygenase-2 inhibitors
HK1027470A (en)	2001-01-12	Phenyl heterocycles as cyclooxygenase-2 inhibitors
HK1033311A (en)	2001-08-24	Phenyl heterocycles as cyclooxygenase-2 inhibitors

Legal Events

Date	Code	Title	Description
2001-12-13	EEER	Examination request
2006-12-19	FZDE	Discontinued