NZ502669A - 5-alkyl-2-arylaminophenylacetic acids and use for treating cyclooxygenase-2 dependent disorders - Google Patents
5-alkyl-2-arylaminophenylacetic acids and use for treating cyclooxygenase-2 dependent disordersInfo
- Publication number
- NZ502669A NZ502669A NZ502669A NZ50266998A NZ502669A NZ 502669 A NZ502669 A NZ 502669A NZ 502669 A NZ502669 A NZ 502669A NZ 50266998 A NZ50266998 A NZ 50266998A NZ 502669 A NZ502669 A NZ 502669A
- Authority
- NZ
- New Zealand
- Prior art keywords
- ethyl
- methyl
- compound
- phenylacetic acid
- fluoro
- Prior art date
Links
- 108010037462 Cyclooxygenase 2 Proteins 0.000 title claims description 40
- 239000002253 acid Substances 0.000 title claims description 25
- 230000001419 dependent effect Effects 0.000 title claims description 8
- 102000010907 Cyclooxygenase 2 Human genes 0.000 title claims 6
- 150000007513 acids Chemical class 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 39
- -1 chloro, methyl Chemical group 0.000 claims abstract description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 241000124008 Mammalia Species 0.000 claims abstract description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 19
- 206010061218 Inflammation Diseases 0.000 claims abstract description 6
- 208000002193 Pain Diseases 0.000 claims abstract description 6
- 230000004054 inflammatory process Effects 0.000 claims abstract description 6
- 230000036407 pain Effects 0.000 claims abstract description 6
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims abstract description 4
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 4
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 39
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 33
- 241001070944 Mimosa Species 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 22
- 230000000694 effects Effects 0.000 claims description 19
- 230000002401 inhibitory effect Effects 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 18
- 230000002829 reductive effect Effects 0.000 claims description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 14
- 229940002612 prodrug Drugs 0.000 claims description 14
- 239000000651 prodrug Substances 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 229960003424 phenylacetic acid Drugs 0.000 claims description 8
- 239000003279 phenylacetic acid Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 6
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 6
- 229940049953 phenylacetate Drugs 0.000 claims description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 5
- 239000012346 acetyl chloride Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- ZEXGDYFACFXQPF-UHFFFAOYSA-N robenacoxib Chemical compound OC(=O)CC1=CC(CC)=CC=C1NC1=C(F)C(F)=CC(F)=C1F ZEXGDYFACFXQPF-UHFFFAOYSA-N 0.000 claims description 4
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 3
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 claims description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- ZRIKWKVMCZQPLV-UHFFFAOYSA-N 2-[2-[2,4-dichloro-6-(trifluoromethyl)anilino]-5-methylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(Cl)C=C(Cl)C=C1C(F)(F)F ZRIKWKVMCZQPLV-UHFFFAOYSA-N 0.000 claims description 2
- ZUGPVDPUDBNEBJ-UHFFFAOYSA-N 2-[2-[2-fluoro-6-(trifluoromethyl)anilino]-5-methylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1C(F)(F)F ZUGPVDPUDBNEBJ-UHFFFAOYSA-N 0.000 claims description 2
- DZTYHNMGAJRMOV-UHFFFAOYSA-N 5-ethyl-1-(2,3,5,6-tetrafluorophenyl)-3h-indol-2-one Chemical compound O=C1CC2=CC(CC)=CC=C2N1C1=C(F)C(F)=CC(F)=C1F DZTYHNMGAJRMOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
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- 239000012065 filter cake Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- LUNFHOZKXHTOLG-UHFFFAOYSA-N hydroxylumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=C(O)C=C1Cl LUNFHOZKXHTOLG-UHFFFAOYSA-N 0.000 claims description 2
- 230000002452 interceptive effect Effects 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000002633 protecting effect Effects 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims 12
- ZDDWMWKQAQNCBL-UHFFFAOYSA-N 2-[2-(2,6-dichloroanilino)-5-methylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(Cl)C=CC=C1Cl ZDDWMWKQAQNCBL-UHFFFAOYSA-N 0.000 claims 2
- NZQRBJYQPQLKPB-UHFFFAOYSA-N 2-[2-(2,4-dichloro-6-fluoroanilino)-5-ethylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(CC)=CC=C1NC1=C(F)C=C(Cl)C=C1Cl NZQRBJYQPQLKPB-UHFFFAOYSA-N 0.000 claims 1
- SXFRVOKANDUVRZ-UHFFFAOYSA-N 2-[2-(2,4-dichloro-6-fluoroanilino)-5-methylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=C(Cl)C=C1Cl SXFRVOKANDUVRZ-UHFFFAOYSA-N 0.000 claims 1
- OKGJGFZQNSWNSS-UHFFFAOYSA-N 2-[2-(2,4-dichloro-6-methylanilino)-5-ethylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(CC)=CC=C1NC1=C(C)C=C(Cl)C=C1Cl OKGJGFZQNSWNSS-UHFFFAOYSA-N 0.000 claims 1
- AOPXCXXMJQKVHW-UHFFFAOYSA-N 2-[2-(2,4-dichloro-6-methylanilino)-5-methylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(C)C=C(Cl)C=C1Cl AOPXCXXMJQKVHW-UHFFFAOYSA-N 0.000 claims 1
- HYMMXWQBWRXAMG-UHFFFAOYSA-N 2-[2-(2,4-difluoro-6-methylanilino)-5-ethylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(CC)=CC=C1NC1=C(C)C=C(F)C=C1F HYMMXWQBWRXAMG-UHFFFAOYSA-N 0.000 claims 1
- WNTCSUFHVADDOL-UHFFFAOYSA-N 2-[2-(2,6-dichloro-4-methylanilino)-5-methylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(Cl)C=C(C)C=C1Cl WNTCSUFHVADDOL-UHFFFAOYSA-N 0.000 claims 1
- ZQWAHOFWNMJMKC-UHFFFAOYSA-N 2-[2-(2-chloro-4-fluoro-6-methylanilino)-5-ethylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(CC)=CC=C1NC1=C(C)C=C(F)C=C1Cl ZQWAHOFWNMJMKC-UHFFFAOYSA-N 0.000 claims 1
- KWHODPWZIFFVQM-UHFFFAOYSA-N 2-[2-(2-chloro-4-fluoro-6-methylanilino)-5-methylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(C)C=C(F)C=C1Cl KWHODPWZIFFVQM-UHFFFAOYSA-N 0.000 claims 1
- LUWAPCYWGRXGEB-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylanilino)-5-ethylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(CC)=CC=C1NC1=C(C)C=CC=C1Cl LUWAPCYWGRXGEB-UHFFFAOYSA-N 0.000 claims 1
- WSKJPVJRMSBMPJ-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylanilino)-5-methylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(C)C=CC=C1Cl WSKJPVJRMSBMPJ-UHFFFAOYSA-N 0.000 claims 1
- HWWCFWSHRQUXFB-UHFFFAOYSA-N 2-[2-(4-chloro-2-fluoro-6-methylanilino)-5-ethylphenyl]acetic acid Chemical compound OC(=O)CC1=CC(CC)=CC=C1NC1=C(C)C=C(Cl)C=C1F HWWCFWSHRQUXFB-UHFFFAOYSA-N 0.000 claims 1
- WDEMBAUGAMYMMT-UHFFFAOYSA-N 2-[2-(4-ethoxy-2,3,5,6-tetrafluoroanilino)-5-ethylphenyl]acetic acid Chemical compound FC1=C(F)C(OCC)=C(F)C(F)=C1NC1=CC=C(CC)C=C1CC(O)=O WDEMBAUGAMYMMT-UHFFFAOYSA-N 0.000 claims 1
- WDXWPGLYTIZLSZ-UHFFFAOYSA-N 2-[2-[2-(2,4-dichloro-6-fluoroanilino)-5-ethylphenyl]acetyl]oxyacetic acid Chemical compound OC(=O)COC(=O)CC1=CC(CC)=CC=C1NC1=C(F)C=C(Cl)C=C1Cl WDXWPGLYTIZLSZ-UHFFFAOYSA-N 0.000 claims 1
- UUEUIZRCYTZMJH-UHFFFAOYSA-N 2-[2-[2-(2,4-dichloro-6-fluoroanilino)-5-methylphenyl]acetyl]oxyacetic acid Chemical compound OC(=O)COC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=C(Cl)C=C1Cl UUEUIZRCYTZMJH-UHFFFAOYSA-N 0.000 claims 1
- OITDWKXFRXJVDA-UHFFFAOYSA-N 2-[2-[2-(2,6-dichloroanilino)-5-ethylphenyl]acetyl]oxyacetic acid Chemical compound OC(=O)COC(=O)CC1=CC(CC)=CC=C1NC1=C(Cl)C=CC=C1Cl OITDWKXFRXJVDA-UHFFFAOYSA-N 0.000 claims 1
- UYLIYQNZCZXIDC-UHFFFAOYSA-N 2-[2-[2-(2,6-dichloroanilino)-5-methylphenyl]acetyl]oxyacetic acid Chemical compound OC(=O)COC(=O)CC1=CC(C)=CC=C1NC1=C(Cl)C=CC=C1Cl UYLIYQNZCZXIDC-UHFFFAOYSA-N 0.000 claims 1
- DTSPZYBNFBSBLW-UHFFFAOYSA-N 2-[2-[2-(2-chloro-4,6-difluoroanilino)-5-ethylphenyl]acetyl]oxyacetic acid Chemical compound OC(=O)COC(=O)CC1=CC(CC)=CC=C1NC1=C(F)C=C(F)C=C1Cl DTSPZYBNFBSBLW-UHFFFAOYSA-N 0.000 claims 1
- VGAHRGNPVGXMHY-UHFFFAOYSA-N 2-[2-[2-(2-chloro-6-fluoroanilino)-5-ethylphenyl]acetyl]oxyacetic acid Chemical compound OC(=O)COC(=O)CC1=CC(CC)=CC=C1NC1=C(F)C=CC=C1Cl VGAHRGNPVGXMHY-UHFFFAOYSA-N 0.000 claims 1
- JPTMQIRJKRBLMA-UHFFFAOYSA-N 2-[2-[2-(2-chloro-6-fluoroanilino)-5-methylphenyl]acetyl]oxyacetic acid Chemical compound OC(=O)COC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl JPTMQIRJKRBLMA-UHFFFAOYSA-N 0.000 claims 1
- BOVUNBOCYOGFGL-UHFFFAOYSA-N 2-[2-[2-(2-chloro-6-methylanilino)-5-ethylphenyl]acetyl]oxyacetic acid Chemical compound OC(=O)COC(=O)CC1=CC(CC)=CC=C1NC1=C(C)C=CC=C1Cl BOVUNBOCYOGFGL-UHFFFAOYSA-N 0.000 claims 1
- RFWVHOOJVWPKGN-UHFFFAOYSA-N 2-[2-[5-ethyl-2-(2,3,5,6-tetrafluoroanilino)phenyl]acetyl]oxyacetic acid Chemical compound OC(=O)COC(=O)CC1=CC(CC)=CC=C1NC1=C(F)C(F)=CC(F)=C1F RFWVHOOJVWPKGN-UHFFFAOYSA-N 0.000 claims 1
- IFXLBMAYBHSJDL-UHFFFAOYSA-N 2-[5-methyl-2-(2,3,5,6-tetrafluoroanilino)phenyl]acetic acid Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C(F)=CC(F)=C1F IFXLBMAYBHSJDL-UHFFFAOYSA-N 0.000 claims 1
- GBFRRPGESIQPLC-UHFFFAOYSA-N 4-nitrooxybutyl 2-[5-ethyl-2-(2,3,5,6-tetrafluoroanilino)phenyl]acetate Chemical compound [O-][N+](=O)OCCCCOC(=O)CC1=CC(CC)=CC=C1NC1=C(F)C(F)=CC(F)=C1F GBFRRPGESIQPLC-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000004817 gas chromatography Methods 0.000 claims 1
- KHPKQFYUPIUARC-UHFFFAOYSA-N lumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl KHPKQFYUPIUARC-UHFFFAOYSA-N 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- HZOREEUASZHZBI-UHFFFAOYSA-N sodium;2-phenylacetic acid Chemical compound [Na+].OC(=O)CC1=CC=CC=C1 HZOREEUASZHZBI-UHFFFAOYSA-N 0.000 claims 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000003491 tear gas Substances 0.000 description 1
- RWWNQEOPUOCKGR-UHFFFAOYSA-N tetraethyltin Chemical compound CC[Sn](CC)(CC)CC RWWNQEOPUOCKGR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/42—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5780397P | 1997-08-28 | 1997-08-28 | |
| US6983797P | 1997-08-28 | 1997-08-28 | |
| PCT/EP1998/005414 WO1999011605A1 (en) | 1997-08-28 | 1998-08-26 | Certain 5-alkyl-2-arylaminophenylacetic acids and derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ502669A true NZ502669A (en) | 2002-02-01 |
Family
ID=26736901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ502669A NZ502669A (en) | 1997-08-28 | 1998-08-26 | 5-alkyl-2-arylaminophenylacetic acids and use for treating cyclooxygenase-2 dependent disorders |
Country Status (34)
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| CN120004366B (zh) * | 2025-04-18 | 2025-07-25 | 浙江九安检测科技有限公司 | 一种二噁英前处理过程中有机试剂的回收方法 |
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| DE3445011A1 (de) | 1983-12-13 | 1985-06-13 | Ciba-Geigy Ag, Basel | Neues anilinderivat, verfahren zu seiner herstellung und seine verwendung |
| GR900100380A (el) * | 1989-05-20 | 1991-10-10 | Fisons Plc | Μέ?οδος παρασκευής αντι-φλεγμονωδών παραγώγων αμινοφενόλης. |
| IT1256345B (it) | 1992-08-20 | 1995-12-01 | Esteri nitrici di derivati dell'acido 2-(2,6-di-alo-fenilammino) fenilacetico e procedimento per la loro preparazione | |
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1998
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| PSEA | Patent sealed | ||
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Owner name: NOVARTIS TIERGESUNDHEIT AG, CH Effective date: 20150515 |
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| EXPY | Patent expired |