ES2225641T3 - Derivados de benzofurano y benzotiofeno como inhibidores de cox-2 selectivos. - Google Patents
Derivados de benzofurano y benzotiofeno como inhibidores de cox-2 selectivos.Info
- Publication number
- ES2225641T3 ES2225641T3 ES01994723T ES01994723T ES2225641T3 ES 2225641 T3 ES2225641 T3 ES 2225641T3 ES 01994723 T ES01994723 T ES 01994723T ES 01994723 T ES01994723 T ES 01994723T ES 2225641 T3 ES2225641 T3 ES 2225641T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- hydrogen
- phenyl
- compound according
- formula
- Prior art date
- 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.)
- Expired - Lifetime
Links
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical class C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title description 11
- 229940111134 coxibs Drugs 0.000 title description 4
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 112
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 78
- -1 cyano, hydroxy Chemical group 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 22
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 150000003462 sulfoxides Chemical group 0.000 claims abstract description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 5
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 7
- 238000000034 method Methods 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 19
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 208000002193 Pain Diseases 0.000 claims description 7
- 230000036407 pain Effects 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 4
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 3
- QGZOTCAOWVKIKJ-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)sulfanyl-6-methylsulfonyl-1-benzothiophene-2-carbonitrile Chemical compound N#CC=1SC2=CC(S(=O)(=O)C)=CC=C2C=1SC1=CC=C(Cl)C=C1Cl QGZOTCAOWVKIKJ-UHFFFAOYSA-N 0.000 claims description 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 description 2
- 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 description 2
- 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 description 2
- VCXFSUIHWSMGJO-UHFFFAOYSA-N 3-(4-ethoxyphenoxy)-6-methylsulfonyl-1-benzothiophene-2-carbonitrile Chemical compound C1=CC(OCC)=CC=C1OC1=C(C#N)SC2=CC(S(C)(=O)=O)=CC=C12 VCXFSUIHWSMGJO-UHFFFAOYSA-N 0.000 claims description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
- 208000025978 Athletic injury Diseases 0.000 claims description 2
- 208000008035 Back Pain Diseases 0.000 claims description 2
- 206010006811 Bursitis Diseases 0.000 claims description 2
- 201000005569 Gout Diseases 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims description 2
- 201000002481 Myositis Diseases 0.000 claims description 2
- 229940124639 Selective inhibitor Drugs 0.000 claims description 2
- 208000000491 Tendinopathy Diseases 0.000 claims description 2
- 206010043255 Tendonitis Diseases 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 231100000869 headache Toxicity 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 201000004595 synovitis Diseases 0.000 claims description 2
- 201000004415 tendinitis Diseases 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 206010036595 Premature delivery Diseases 0.000 claims 2
- 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
- 208000010040 Sprains and Strains Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- 239000002253 acid Substances 0.000 description 28
- 241000700159 Rattus Species 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 125000005843 halogen group Chemical group 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 229910001868 water Inorganic materials 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 230000003110 anti-inflammatory effect Effects 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000001727 in vivo Methods 0.000 description 10
- 150000003180 prostaglandins Chemical class 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 6
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-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
- 239000003981 vehicle Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 5
- 239000000679 carrageenan Substances 0.000 description 5
- 235000010418 carrageenan Nutrition 0.000 description 5
- 229940113118 carrageenan Drugs 0.000 description 5
- 229920001525 carrageenan Polymers 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 5
- 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
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
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- 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 3
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- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 3
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- MUEWUNUBHRREED-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-methylsulfanylbenzene Chemical compound COC(OC)C1=CC=C(SC)C=C1 MUEWUNUBHRREED-UHFFFAOYSA-N 0.000 description 2
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 2
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- 238000000844 transformation Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000001755 vocal effect Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- 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
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- 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
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
- A61P19/08—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
-
- 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
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25128300P | 2000-12-05 | 2000-12-05 | |
| US251283P | 2000-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2225641T3 true ES2225641T3 (es) | 2005-03-16 |
Family
ID=22951260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01994723T Expired - Lifetime ES2225641T3 (es) | 2000-12-05 | 2001-11-26 | Derivados de benzofurano y benzotiofeno como inhibidores de cox-2 selectivos. |
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
-
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 |
| ZA200303641B (en) | 2004-08-12 |
| 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 |
| KR20030070054A (ko) | 2003-08-27 |
| DE60105195T2 (de) | 2005-09-08 |
| MXPA03004398A (es) | 2003-09-05 |
| AU2002224890B2 (en) | 2007-03-22 |
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