OA11912A - Substituted benzopyran analogs for the treatment of inflammation. - Google Patents
Substituted benzopyran analogs for the treatment of inflammation. Download PDFInfo
- Publication number
- OA11912A OA11912A OA00100098A OA00100098A OA11912A OA 11912 A OA11912 A OA 11912A OA 00100098 A OA00100098 A OA 00100098A OA 00100098 A OA00100098 A OA 00100098A OA 11912 A OA11912 A OA 11912A
- Authority
- OA
- OAPI
- Prior art keywords
- chloro
- benzopyran
- trifluoromethyl
- carboxylic acid
- alkyl
- Prior art date
Links
- 150000001562 benzopyrans Chemical class 0.000 title abstract description 5
- 238000011282 treatment Methods 0.000 title description 22
- 206010061218 Inflammation Diseases 0.000 title description 15
- 230000004054 inflammatory process Effects 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 203
- 230000001404 mediated effect Effects 0.000 claims abstract description 9
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims abstract description 8
- -1 carboxyl,aminocarbonyl Chemical group 0.000 claims description 644
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 164
- 238000000034 method Methods 0.000 claims description 156
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 88
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- 125000005843 halogen group Chemical group 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 44
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 41
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 208000035475 disorder Diseases 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 206010028980 Neoplasm Diseases 0.000 claims description 18
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 18
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 17
- 125000006413 ring segment Chemical group 0.000 claims description 17
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 13
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims description 7
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 7
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 7
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 208000002193 Pain Diseases 0.000 claims description 5
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 5
- 230000036407 pain Effects 0.000 claims description 5
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 5
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
- VIUDHZOBRHLGGI-UHFFFAOYSA-N 2-(trifluoromethyl)quinoline-3-carboxylic acid Chemical compound C1=CC=C2N=C(C(F)(F)F)C(C(=O)O)=CC2=C1 VIUDHZOBRHLGGI-UHFFFAOYSA-N 0.000 claims description 4
- USUXAIZKXRKACF-UHFFFAOYSA-N 6-chloro-7-(4-chlorophenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=C1OC1=CC=C(Cl)C=C1 USUXAIZKXRKACF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- WTDNHPVKFJKCLA-UHFFFAOYSA-N 6-chloro-7-(2,6-dimethylphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound CC1=CC=CC(C)=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)C(C(F)(F)F)O2 WTDNHPVKFJKCLA-UHFFFAOYSA-N 0.000 claims description 3
- JDAKFOAMRMTLPB-UHFFFAOYSA-N 6-chloro-7-(3-chlorophenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=C1OC1=CC=CC(Cl)=C1 JDAKFOAMRMTLPB-UHFFFAOYSA-N 0.000 claims description 3
- WGFWSWGWXBNCCZ-UHFFFAOYSA-N 6-chloro-7-(4-methoxyphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1OC(C(=C1)Cl)=CC2=C1C=C(C(O)=O)C(C(F)(F)F)O2 WGFWSWGWXBNCCZ-UHFFFAOYSA-N 0.000 claims description 3
- MESQNZFBUFUYBU-UHFFFAOYSA-N 6-chloro-7-ethenyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=C(C=C)C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 MESQNZFBUFUYBU-UHFFFAOYSA-N 0.000 claims description 3
- DKGUYSCXMLJEMN-UHFFFAOYSA-N 6-chloro-7-ethynyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=C(C#C)C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 DKGUYSCXMLJEMN-UHFFFAOYSA-N 0.000 claims description 3
- FXBHKVGCDPQUFU-UHFFFAOYSA-N 6-chloro-7-iodo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=C(I)C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 FXBHKVGCDPQUFU-UHFFFAOYSA-N 0.000 claims description 3
- YAVXJECQZADRQE-UHFFFAOYSA-N 6-chloro-7-phenoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=C1OC1=CC=CC=C1 YAVXJECQZADRQE-UHFFFAOYSA-N 0.000 claims description 3
- DFSPHBGGYCORBV-UHFFFAOYSA-N 6-chloro-7-phenylsulfanyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=C1SC1=CC=CC=C1 DFSPHBGGYCORBV-UHFFFAOYSA-N 0.000 claims description 3
- SKSJXANOWLGXJF-UHFFFAOYSA-N 7-(2-bromo-4-chlorophenoxy)-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=C1OC1=CC=C(Cl)C=C1Br SKSJXANOWLGXJF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- OFUNDCRIGSMJCI-UHFFFAOYSA-N 6-chloro-7-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=C(OCC(F)(F)F)C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 OFUNDCRIGSMJCI-UHFFFAOYSA-N 0.000 claims description 2
- RSKVDELBMNBSTP-UHFFFAOYSA-N 6-chloro-7-(3,4-difluorophenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=C1OC1=CC=C(F)C(F)=C1 RSKVDELBMNBSTP-UHFFFAOYSA-N 0.000 claims description 2
- MIKORCPETDAVNW-UHFFFAOYSA-N 7-(3-carboxyphenoxy)-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=C1OC1=CC=CC(C(O)=O)=C1 MIKORCPETDAVNW-UHFFFAOYSA-N 0.000 claims description 2
- SPFFNYADAUWUJR-UHFFFAOYSA-N 7-phenoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=C1OC1=CC=CC=C1 SPFFNYADAUWUJR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- XPSHZEIXHOTEFE-UHFFFAOYSA-N 7-(4-carboxy-2-chlorophenoxy)-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=C1OC1=CC=C(C(O)=O)C=C1Cl XPSHZEIXHOTEFE-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 abstract description 2
- 102000010907 Cyclooxygenase 2 Human genes 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 253
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 207
- 238000005481 NMR spectroscopy Methods 0.000 description 172
- 239000002253 acid Substances 0.000 description 163
- 239000007787 solid Substances 0.000 description 149
- 239000000243 solution Substances 0.000 description 139
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 127
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 111
- 150000003254 radicals Chemical class 0.000 description 107
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 93
- 229940093499 ethyl acetate Drugs 0.000 description 87
- 229910001868 water Inorganic materials 0.000 description 86
- 235000019439 ethyl acetate Nutrition 0.000 description 83
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 80
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 238000006243 chemical reaction Methods 0.000 description 71
- 150000002148 esters Chemical class 0.000 description 70
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- 229960004132 diethyl ether Drugs 0.000 description 56
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 53
- 125000004432 carbon atom Chemical group C* 0.000 description 49
- DEBZQUFVQZPPLC-UHFFFAOYSA-N 2h-chromene-3-carboxylic acid Chemical compound C1=CC=C2OCC(C(=O)O)=CC2=C1 DEBZQUFVQZPPLC-UHFFFAOYSA-N 0.000 description 43
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 41
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- 235000011121 sodium hydroxide Nutrition 0.000 description 37
- 238000005160 1H NMR spectroscopy Methods 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 36
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- 239000000725 suspension Substances 0.000 description 28
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- 238000003756 stirring Methods 0.000 description 27
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
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- NDCFBPDNHOZORS-UHFFFAOYSA-N 1,2-dihydroquinoline-3-carboxylic acid Chemical compound C1=CC=C2NCC(C(=O)O)=CC2=C1 NDCFBPDNHOZORS-UHFFFAOYSA-N 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
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- 238000004587 chromatography analysis Methods 0.000 description 9
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- 230000008025 crystallization Effects 0.000 description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- 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
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- 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
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- 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
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/175,584 US6077850A (en) | 1997-04-21 | 1998-10-20 | Substituted benzopyran analogs for the treatment of inflammation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11912A true OA11912A (en) | 2006-04-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA00100098A OA11912A (en) | 1998-10-20 | 1999-10-15 | Substituted benzopyran analogs for the treatment of inflammation. |
Country Status (33)
| Country | Link |
|---|---|
| US (4) | US6077850A (fr) |
| EP (1) | EP1123285A1 (fr) |
| JP (1) | JP2002527512A (fr) |
| KR (1) | KR20010086438A (fr) |
| CN (1) | CN1150181C (fr) |
| AP (1) | AP2001002143A0 (fr) |
| AR (1) | AR024839A1 (fr) |
| AU (1) | AU767655C (fr) |
| BG (1) | BG105513A (fr) |
| BR (1) | BR9914696A (fr) |
| CA (1) | CA2347910A1 (fr) |
| CU (1) | CU23029A3 (fr) |
| CZ (1) | CZ20011424A3 (fr) |
| EA (1) | EA005599B1 (fr) |
| EE (1) | EE200100227A (fr) |
| GE (1) | GEP20033027B (fr) |
| HK (1) | HK1040397B (fr) |
| HR (1) | HRP20010288A2 (fr) |
| HU (1) | HUP0104316A3 (fr) |
| ID (1) | ID30062A (fr) |
| IL (1) | IL142667A0 (fr) |
| IS (1) | IS5921A (fr) |
| MY (1) | MY138238A (fr) |
| NO (1) | NO20011940L (fr) |
| NZ (1) | NZ511593A (fr) |
| OA (1) | OA11912A (fr) |
| PL (1) | PL347384A1 (fr) |
| SK (1) | SK5412001A3 (fr) |
| TR (1) | TR200101969T2 (fr) |
| TW (1) | TWI250979B (fr) |
| UA (1) | UA75328C2 (fr) |
| WO (1) | WO2000023433A1 (fr) |
| ZA (1) | ZA200103200B (fr) |
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| KR100485642B1 (ko) * | 1996-03-18 | 2005-09-30 | 에자이 가부시키가이샤 | 축합고리함유카르복실산유도체 |
| US6077850A (en) * | 1997-04-21 | 2000-06-20 | G.D. Searle & Co. | Substituted benzopyran analogs for the treatment of inflammation |
| US20040072889A1 (en) * | 1997-04-21 | 2004-04-15 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an alkylating-type antineoplastic agent as a combination therapy in the treatment of neoplasia |
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| US6833373B1 (en) | 1998-12-23 | 2004-12-21 | G.D. Searle & Co. | Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| US20040053900A1 (en) * | 1998-12-23 | 2004-03-18 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an aromatase inhibitor as a combination therapy |
| US20030013739A1 (en) * | 1998-12-23 | 2003-01-16 | Pharmacia Corporation | Methods of using a combination of cyclooxygenase-2 selective inhibitors and thalidomide for the treatment of neoplasia |
| US20030119895A1 (en) * | 1998-12-23 | 2003-06-26 | Pharmacia Corporation | Methods using a combination of a 3-heteroaryl-2-indolinone and a cyclooxygenase-2 inhibitor for the treatment of neoplasia |
| US20020103141A1 (en) * | 1998-12-23 | 2002-08-01 | Mckearn John P. | Antiangiogenic combination therapy for the treatment of cancer |
| US20040122011A1 (en) * | 1998-12-23 | 2004-06-24 | Pharmacia Corporation | Method of using a COX-2 inhibitor and a TACE inhibitors as a combination therapy |
| US20030203956A1 (en) * | 1998-12-23 | 2003-10-30 | Masterrer Jaime L. | Method of using a cyclooxygenase-2 inhibitor and one or more ornithine decarboxylase inhibitors as a combination therapy in the treatment of neoplasia |
| IL136025A0 (en) * | 1999-05-14 | 2001-05-20 | Pfizer Prod Inc | Combination therapy for the treatment of migraine |
| CO5190664A1 (es) | 1999-06-30 | 2002-08-29 | Pfizer Prod Inc | Terapia de combinacion para el tratamiento de migrana administracion de un receptor 5ht, cafeina y un inhibidor de ciclooxigenasa-2 |
| PT1274700E (pt) * | 2000-01-03 | 2005-02-28 | Pharmacia Corp | Di-hidrobenzopiranos di-hidrobenzotiopiranos e tetra-hidroquinolinas para o tratamento de afeccoes mediadas por cox-2 |
| US6716829B2 (en) | 2000-07-27 | 2004-04-06 | Pharmacia Corporation | Aldosterone antagonist and cyclooxygenase-2 inhibitor combination therapy to prevent or treat inflammation-related cardiovascular disorders |
| CN1199950C (zh) * | 2000-08-09 | 2005-05-04 | 霍夫曼-拉罗奇有限公司 | 作为抗炎剂的喹啉衍生物 |
| EP1365753A2 (fr) * | 2001-02-02 | 2003-12-03 | Pharmacia Corporation | Combinaisons d'uroguanyline et d'inhibiteur de cyclooxygenase-2 pour l'inhibition du cancer de l'intestin |
| US20050143360A1 (en) * | 2001-02-02 | 2005-06-30 | Joel Krasnow | Method of using a cyclooxygenase-2 inhibitor and sex steroids as a combination therapy for the treatment and prevention of dismenorrhea |
| US7012098B2 (en) * | 2001-03-23 | 2006-03-14 | Pharmacia Corporation | Inhibitors of inducible nitric oxide synthase for chemoprevention and treatment of cancers |
| WO2002078625A2 (fr) * | 2001-03-28 | 2002-10-10 | Pharmacia Corporation | Combinaisons therapeutiques pour signes cardiovasculaires et inflammatoires |
| DE10121252A1 (de) * | 2001-04-30 | 2002-11-07 | Christos C Zouboulis | Behandlung der Akne |
| US20030153801A1 (en) * | 2001-05-29 | 2003-08-14 | Pharmacia Corporation | Compositions of cyclooxygenase-2 selective inhibitors and radiation for inhibition or prevention of cardiovascular disease |
| DE10129320A1 (de) * | 2001-06-19 | 2003-04-10 | Norbert Mueller | Verwendung von COX-2 Inhibitoren zur Behandlung von Schizophrenie, wahnhaften Störungen, affektiven Störungen oder Ticstörungen |
| US20060167074A1 (en) * | 2001-06-19 | 2006-07-27 | Norbert Muller | Methods and compositions for the treatment of psychiatric disorders |
| US20040067992A1 (en) * | 2001-08-10 | 2004-04-08 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and a carbonic anhydrase inhibitor for the treatment of neoplasia |
| US20030100594A1 (en) * | 2001-08-10 | 2003-05-29 | Pharmacia Corporation | Carbonic anhydrase inhibitor |
| US20050101563A1 (en) * | 2001-08-14 | 2005-05-12 | Pharmacia Corporation | Method and compositions for the treatment and prevention of pain and inflammation |
| US20030114416A1 (en) * | 2001-08-14 | 2003-06-19 | Pharmacia Corporation | Method and compositions for the treatment and prevention of pain and inflammation with a cyclooxygenase-2 selective inhibitor and chondroitin sulfate |
| AR038957A1 (es) * | 2001-08-15 | 2005-02-02 | Pharmacia Corp | Terapia de combinacion para el tratamiento del cancer |
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| TW200403072A (en) * | 2002-01-23 | 2004-03-01 | Upjohn Co | Combination therapy for the treatment of bacterial infections |
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| BR0309259A (pt) * | 2002-04-18 | 2005-02-09 | Pharmacia Corp | Terapia combinada para o tratamento de doença de parkinson com inibidores de ciclooxigenase-2 (cox 2) |
| GB0209257D0 (en) * | 2002-04-23 | 2002-06-05 | Novartis Ag | Organic compounds |
| WO2004004833A1 (fr) * | 2002-07-02 | 2004-01-15 | Pharmacia Corporation | Utilisation d'inhibiteurs selectifs de cyclooxygenase-2 et d'agents thrombolitiques pour le traitement ou la prevention d'un evenement d'occlusion vasculaire |
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| DE60332387D1 (de) | 2002-12-13 | 2010-06-10 | Warner Lambert Co | Alpha-2-delta-ligand zur behandlung vonsymptomen der unteren harnwege |
| AU2003297397A1 (en) * | 2002-12-19 | 2004-07-14 | Pharmacia Corp | Methods and compositions for the treatment of herpes virus infections using cyclooxygenase-2 selective inhibitors or cyclooxygenase-2 inhibitors in combination with antiviral agents |
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| US20050026902A1 (en) * | 2003-01-31 | 2005-02-03 | Timothy Maziasz | Methods and compositions for the treatment or prevention of human immunodeficiency virus and related conditions using cyclooxygenase-2 selective inhibitors and antiviral agents |
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