ZA200303641B - Benzofuran and benzothiophene derivatives as selective COX-2 inhibitors. - Google Patents
Benzofuran and benzothiophene derivatives as selective COX-2 inhibitors. Download PDFInfo
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- ZA200303641B ZA200303641B ZA200303641A ZA200303641A ZA200303641B ZA 200303641 B ZA200303641 B ZA 200303641B ZA 200303641 A ZA200303641 A ZA 200303641A ZA 200303641 A ZA200303641 A ZA 200303641A ZA 200303641 B ZA200303641 B ZA 200303641B
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- South Africa
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- compound
- alkyl
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- acid
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title description 12
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title description 7
- 229940111134 coxibs Drugs 0.000 title description 3
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- -1 individual isomers Substances 0.000 claims description 45
- 201000010099 disease Diseases 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- 229940002612 prodrug Drugs 0.000 claims description 8
- 239000000651 prodrug Substances 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 4
- 206010036600 Premature labour Diseases 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 208000026440 premature labor Diseases 0.000 claims description 4
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- 208000008035 Back Pain Diseases 0.000 claims description 3
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- 206010043255 Tendonitis Diseases 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 231100000869 headache Toxicity 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 201000004595 synovitis Diseases 0.000 claims description 3
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- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- MVWPDJHXDFYOBO-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfanyl-6-methylsulfonyl-1-benzothiophene-2-carbonitrile Chemical compound N#CC=1SC2=CC(S(=O)(=O)C)=CC=C2C=1SC1=CC=CC=C1Cl MVWPDJHXDFYOBO-UHFFFAOYSA-N 0.000 claims 1
- QLQJYIFVJNQHDY-UHFFFAOYSA-N 3-(2-fluorophenyl)sulfanyl-6-methylsulfonyl-1-benzothiophene-2-carbonitrile Chemical compound N#CC=1SC2=CC(S(=O)(=O)C)=CC=C2C=1SC1=CC=CC=C1F QLQJYIFVJNQHDY-UHFFFAOYSA-N 0.000 claims 1
- XPOSOACFOVKIOF-UHFFFAOYSA-N 3-(4-chloro-2-fluorophenoxy)-6-methylsulfonyl-1-benzothiophene-2-carbonitrile Chemical compound N#CC=1SC2=CC(S(=O)(=O)C)=CC=C2C=1OC1=CC=C(Cl)C=C1F XPOSOACFOVKIOF-UHFFFAOYSA-N 0.000 claims 1
- WXEANUYPVQMIDM-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfanyl-6-methylsulfonyl-1-benzothiophene-2-carbonitrile Chemical compound N#CC=1SC2=CC(S(=O)(=O)C)=CC=C2C=1SC1=CC=C(F)C=C1 WXEANUYPVQMIDM-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- CUPOOAWTRIURFT-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical compound N#CC1=CC=CS1 CUPOOAWTRIURFT-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 125000005843 halogen group Chemical group 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 150000003180 prostaglandins Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 9
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 125000003884 phenylalkyl group Chemical group 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 4
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
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- 125000000524 functional group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 150000003457 sulfones Chemical class 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 208000006673 asthma Diseases 0.000 description 3
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
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- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 229940124639 Selective inhibitor Drugs 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- 125000002947 alkylene group Chemical group 0.000 description 2
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- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 230000005764 inhibitory process Effects 0.000 description 2
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- MUEWUNUBHRREED-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-methylsulfanylbenzene Chemical compound COC(OC)C1=CC=C(SC)C=C1 MUEWUNUBHRREED-UHFFFAOYSA-N 0.000 description 1
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical class C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 1
- QJAQZEIHRUYKGS-UHFFFAOYSA-N 1-benzothiophene;2h-tetrazole Chemical compound C1=NN=NN1.C1=CC=C2SC=CC2=C1 QJAQZEIHRUYKGS-UHFFFAOYSA-N 0.000 description 1
- AMMPLVWPWSYRDR-UHFFFAOYSA-N 1-methylbicyclo[2.2.2]oct-2-ene-4-carboxylic acid Chemical compound C1CC2(C(O)=O)CCC1(C)C=C2 AMMPLVWPWSYRDR-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
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Classifications
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- 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Psychiatry (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Immunology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25128300P | 2000-12-05 | 2000-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200303641B true ZA200303641B (en) | 2004-08-12 |
Family
ID=22951260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200303641A ZA200303641B (en) | 2000-12-05 | 2003-05-12 | Benzofuran and benzothiophene derivatives as selective COX-2 inhibitors. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6433005B1 (enExample) |
| EP (1) | EP1347963B1 (enExample) |
| JP (1) | JP4212892B2 (enExample) |
| KR (1) | KR20030070054A (enExample) |
| CN (1) | CN1273460C (enExample) |
| AR (1) | AR035719A1 (enExample) |
| AT (1) | ATE274507T1 (enExample) |
| AU (2) | AU2002224890B2 (enExample) |
| BR (1) | BR0115963A (enExample) |
| CA (1) | CA2437048A1 (enExample) |
| DE (1) | DE60105195T2 (enExample) |
| ES (1) | ES2225641T3 (enExample) |
| MX (1) | MXPA03004398A (enExample) |
| PT (1) | PT1347963E (enExample) |
| WO (1) | WO2002046178A2 (enExample) |
| ZA (1) | ZA200303641B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999051587A1 (en) * | 1998-04-01 | 1999-10-14 | Ono Pharmaceutical Co., Ltd. | Fused thiophene derivatives and drugs containing the same as the active ingredient |
| JP2001261674A (ja) * | 2000-03-22 | 2001-09-26 | Mitsui Chemicals Inc | ベンゾチオフェン誘導体およびそれを有効成分として含有する核内レセプター作動薬 |
| AU5878001A (en) * | 2000-05-18 | 2001-11-26 | Daiichi Pharmaceutical Co., Ltd. | Novel benzothiophene derivatives |
| AU2001268051A1 (en) * | 2000-06-28 | 2002-01-08 | Eli Lilly And Company | Spla2 inhibitors |
| US7071220B2 (en) * | 2000-09-18 | 2006-07-04 | Toa Eiyo Ltd. | N-substituted benzothiophenesulfonamide derivatives |
| WO2005033112A2 (en) * | 2003-10-02 | 2005-04-14 | Cephalon, Inc. | Substituted indole derivatives |
| ATE555091T1 (de) | 2006-02-03 | 2012-05-15 | Bionomics Ltd | Substituierte benzofurane, benzothiophene, benzoselenophene und indole und ihre verwendung als tubulinpolymerisationsinhibitoren |
| WO2008055808A1 (en) | 2006-11-09 | 2008-05-15 | F. Hoffmann-La Roche Ag | Indole and benzofuran 2-carboxamide derivatives |
| AU2011202542A1 (en) | 2010-07-14 | 2012-02-02 | Indian Institute Of Science | Benzothiophene carboxamide compounds, composition and applications thereof |
| CN103819371B (zh) * | 2012-11-16 | 2016-05-04 | 中国科学院大连化学物理研究所 | 一种对甲砜基苯甲醛的合成方法 |
| CN103058988B (zh) * | 2012-12-31 | 2015-09-02 | 中国人民大学 | 苯并噻吩及其衍生物及其制备方法与应用 |
| CN110903225B (zh) * | 2019-12-11 | 2021-11-09 | 苏州开元民生科技股份有限公司 | 一种对甲砜基苯甲醛的合成方法 |
| CN114456136B (zh) * | 2022-01-27 | 2024-06-07 | 广西中医药大学 | 双靶点非甾体抗炎化合物及其制备方法与用途 |
| KR102542698B1 (ko) * | 2022-04-05 | 2023-06-14 | 주식회사 베노바이오 | 신규한 벤조사이오펜 유도체 및 bet 억제제로서의 용도 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3331854A (en) * | 1964-12-14 | 1967-07-18 | American Cyanamid Co | Novel furan and thiophene compounds |
| US4663347A (en) | 1983-10-31 | 1987-05-05 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid esters useful as inhibitors of leukotriene biosynthesis |
| US4745127A (en) * | 1983-10-31 | 1988-05-17 | Merck Frosst Canada, Inc. | Benzyl esters of benzofuran-2-carboxylic acids useful as inhibitors of leukotriene biosynthesis |
| US4822803A (en) | 1983-10-31 | 1989-04-18 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid hydrazides useful as inhibitors of leukotriene biosynthesis |
| US4933351A (en) | 1983-10-31 | 1990-06-12 | Merck Frosst Canada, Inc. | Benzofuran 2-carbox amides useful as inhibitors of leukoriene biosynthesis |
| DE3342624A1 (de) | 1983-11-25 | 1984-03-29 | Heinfried Dr. 4019 Monheim Grote | Benzaronderivate, verfahren zu ihrer herstellung und diese derivate enthaltende arzneimittel |
| US4621091A (en) | 1984-10-09 | 1986-11-04 | Merck & Co., Inc. | 3-hydroxybenzo[b]thiophene-2-sulfide derivatives compositions, and method of use therefor |
| US5208253A (en) * | 1992-02-24 | 1993-05-04 | Warner-Lambert Company | 3-alkyloxy-, aryloxy-, or arylalkyloxy-benzo(b) thiophene-2-carboxamides as inhibitors of cell adhesion |
| WO1995002406A2 (en) | 1993-07-15 | 1995-01-26 | Warner-Lambert Company | Use of benzothiophenes and benzofurans for the treatment of inflammatory bowel disease and inflammation assay method |
| US5426113A (en) | 1994-04-08 | 1995-06-20 | Warner-Lambert Company | Method of preventing ulcer formation caused by nonsteroidal antiinflammatory drugs employing tetrazol-benzothiophene carboxamide compounds |
| US5521213A (en) * | 1994-08-29 | 1996-05-28 | Merck Frosst Canada, Inc. | Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2 |
| CN1211921A (zh) * | 1996-02-22 | 1999-03-24 | 伊莱利利公司 | 苯并噻吩、含有它们的制剂及其制备方法 |
| US5731342A (en) | 1996-02-22 | 1998-03-24 | Eli Lilly And Company | Benzothiophenes, formulations containing same, and methods |
-
2001
- 2001-11-26 KR KR10-2003-7007600A patent/KR20030070054A/ko not_active Abandoned
- 2001-11-26 MX MXPA03004398A patent/MXPA03004398A/es active IP Right Grant
- 2001-11-26 PT PT01994723T patent/PT1347963E/pt unknown
- 2001-11-26 DE DE60105195T patent/DE60105195T2/de not_active Expired - Fee Related
- 2001-11-26 AT AT01994723T patent/ATE274507T1/de not_active IP Right Cessation
- 2001-11-26 CA CA002437048A patent/CA2437048A1/en not_active Abandoned
- 2001-11-26 WO PCT/EP2001/013716 patent/WO2002046178A2/en not_active Ceased
- 2001-11-26 AU AU2002224890A patent/AU2002224890B2/en not_active Ceased
- 2001-11-26 BR BR0115963-1A patent/BR0115963A/pt not_active IP Right Cessation
- 2001-11-26 ES ES01994723T patent/ES2225641T3/es not_active Expired - Lifetime
- 2001-11-26 JP JP2002547917A patent/JP4212892B2/ja not_active Expired - Fee Related
- 2001-11-26 CN CNB01820077XA patent/CN1273460C/zh not_active Expired - Fee Related
- 2001-11-26 AU AU2489002A patent/AU2489002A/xx active Pending
- 2001-11-26 EP EP01994723A patent/EP1347963B1/en not_active Expired - Lifetime
- 2001-12-03 US US10/006,349 patent/US6433005B1/en not_active Expired - Fee Related
- 2001-12-03 AR ARP010105603A patent/AR035719A1/es not_active Application Discontinuation
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2003
- 2003-05-12 ZA ZA200303641A patent/ZA200303641B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20020107280A1 (en) | 2002-08-08 |
| EP1347963B1 (en) | 2004-08-25 |
| WO2002046178A2 (en) | 2002-06-13 |
| CN1479736A (zh) | 2004-03-03 |
| EP1347963A2 (en) | 2003-10-01 |
| US6433005B1 (en) | 2002-08-13 |
| AR035719A1 (es) | 2004-07-07 |
| AU2489002A (en) | 2002-06-18 |
| DE60105195D1 (de) | 2004-09-30 |
| BR0115963A (pt) | 2003-10-28 |
| CA2437048A1 (en) | 2002-06-13 |
| ATE274507T1 (de) | 2004-09-15 |
| CN1273460C (zh) | 2006-09-06 |
| JP4212892B2 (ja) | 2009-01-21 |
| JP2004517088A (ja) | 2004-06-10 |
| PT1347963E (pt) | 2004-12-31 |
| WO2002046178A3 (en) | 2002-10-10 |
| ES2225641T3 (es) | 2005-03-16 |
| KR20030070054A (ko) | 2003-08-27 |
| DE60105195T2 (de) | 2005-09-08 |
| MXPA03004398A (es) | 2003-09-05 |
| AU2002224890B2 (en) | 2007-03-22 |
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