NL194914C - 4H-1-benzopyran-4-onderivaat of zout daarvan, en farmaceutisch preparaat dat dit als actieve stof bevat. - Google Patents
4H-1-benzopyran-4-onderivaat of zout daarvan, en farmaceutisch preparaat dat dit als actieve stof bevat. Download PDFInfo
- Publication number
- NL194914C NL194914C NL8802464A NL8802464A NL194914C NL 194914 C NL194914 C NL 194914C NL 8802464 A NL8802464 A NL 8802464A NL 8802464 A NL8802464 A NL 8802464A NL 194914 C NL194914 C NL 194914C
- Authority
- NL
- Netherlands
- Prior art keywords
- compound
- formula
- reaction
- benzopyran
- group
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 37
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 3
- 239000013543 active substance Substances 0.000 title claims description 4
- 150000004777 chromones Chemical class 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 11
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 235000019359 magnesium stearate Nutrition 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 4
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- VDRKWLBFWNQJEY-UHFFFAOYSA-N 7-(methanesulfonamido)-4-oxo-6-phenoxychromene-3-carboxamide Chemical compound CS(=O)(=O)NC1=CC=2OC=C(C(N)=O)C(=O)C=2C=C1OC1=CC=CC=C1 VDRKWLBFWNQJEY-UHFFFAOYSA-N 0.000 claims description 2
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 229940079832 sodium starch glycolate Drugs 0.000 claims 1
- 229920003109 sodium starch glycolate Polymers 0.000 claims 1
- 239000008109 sodium starch glycolate Substances 0.000 claims 1
- 238000010561 standard procedure Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 23
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 323
- 239000002904 solvent Substances 0.000 description 184
- 238000006243 chemical reaction Methods 0.000 description 174
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 154
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 151
- 239000000203 mixture Substances 0.000 description 127
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 105
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 96
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- -1 sulfonamide compounds Chemical class 0.000 description 88
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- 238000002360 preparation method Methods 0.000 description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 67
- 239000000243 solution Substances 0.000 description 64
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 59
- 230000002829 reductive effect Effects 0.000 description 50
- 239000002585 base Substances 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
- 238000002844 melting Methods 0.000 description 41
- 230000008018 melting Effects 0.000 description 41
- 239000012044 organic layer Substances 0.000 description 40
- 229910052739 hydrogen Inorganic materials 0.000 description 39
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 37
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 35
- 239000013078 crystal Chemical group 0.000 description 35
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 230000002411 adverse Effects 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 30
- 229920006395 saturated elastomer Polymers 0.000 description 29
- 239000003795 chemical substances by application Substances 0.000 description 27
- 239000011780 sodium chloride Substances 0.000 description 27
- 239000003513 alkali Substances 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- 150000001408 amides Chemical class 0.000 description 21
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 13
- 230000002401 inhibitory effect Effects 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 235000011181 potassium carbonates Nutrition 0.000 description 13
- 239000012312 sodium hydride Substances 0.000 description 13
- 229910000104 sodium hydride Inorganic materials 0.000 description 13
- 239000003480 eluent Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000005457 ice water Substances 0.000 description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 150000008282 halocarbons Chemical class 0.000 description 10
- 230000002140 halogenating effect Effects 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- 239000011591 potassium Substances 0.000 description 10
- 229910052700 potassium Inorganic materials 0.000 description 10
- 229960003975 potassium Drugs 0.000 description 10
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 150000003462 sulfoxides Chemical class 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 9
- 150000001340 alkali metals Chemical class 0.000 description 9
- 150000004703 alkoxides Chemical class 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 235000019253 formic acid Nutrition 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- 230000037396 body weight Effects 0.000 description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- 150000004678 hydrides Chemical class 0.000 description 8
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 8
- 229910000105 potassium hydride Inorganic materials 0.000 description 8
- 125000000547 substituted alkyl group Chemical group 0.000 description 8
- 239000002841 Lewis acid Substances 0.000 description 7
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- 239000003054 catalyst Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
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- 239000010410 layer Substances 0.000 description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
- 238000006798 ring closing metathesis reaction Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
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- 230000005764 inhibitory process Effects 0.000 description 5
- 150000007522 mineralic acids Chemical class 0.000 description 5
- CMYTTYZJZGQZMC-UHFFFAOYSA-N n-(4-acetyl-5-hydroxy-2-phenoxyphenyl)methanesulfonamide Chemical compound C1=C(O)C(C(=O)C)=CC(OC=2C=CC=CC=2)=C1NS(C)(=O)=O CMYTTYZJZGQZMC-UHFFFAOYSA-N 0.000 description 5
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- 239000000126 substance Substances 0.000 description 5
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- 229910015900 BF3 Inorganic materials 0.000 description 4
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
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- 239000008101 lactose Substances 0.000 description 4
- WWVPKCKYEBZBBL-UHFFFAOYSA-N n-(4-oxo-6-phenoxy-2,3-dihydrochromen-7-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=2OCCC(=O)C=2C=C1OC1=CC=CC=C1 WWVPKCKYEBZBBL-UHFFFAOYSA-N 0.000 description 4
- KJJUXOQDQJGDTI-UHFFFAOYSA-N n-(4-oxo-6-phenoxychromen-7-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=2OC=CC(=O)C=2C=C1OC1=CC=CC=C1 KJJUXOQDQJGDTI-UHFFFAOYSA-N 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
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- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 3
- BSZROLGDSDRYJH-UHFFFAOYSA-N 3-amino-4-phenoxyphenol Chemical compound NC1=CC(O)=CC=C1OC1=CC=CC=C1 BSZROLGDSDRYJH-UHFFFAOYSA-N 0.000 description 3
- MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 3
- UOGZDMKXQVZVGO-UHFFFAOYSA-N 5-methoxy-2-phenoxyaniline Chemical compound NC1=CC(OC)=CC=C1OC1=CC=CC=C1 UOGZDMKXQVZVGO-UHFFFAOYSA-N 0.000 description 3
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
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- UFDUHSWDBJFAIG-UHFFFAOYSA-N n-(3-methylsulfinyl-4-oxo-6-phenoxychromen-7-yl)methanesulfonamide Chemical compound C1=C2C(=O)C(S(=O)C)=COC2=CC(NS(C)(=O)=O)=C1OC1=CC=CC=C1 UFDUHSWDBJFAIG-UHFFFAOYSA-N 0.000 description 1
- UUTAORFVKHTLIB-UHFFFAOYSA-N n-(3-methylsulfonyl-4-oxo-6-phenoxychromen-7-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=2OC=C(S(C)(=O)=O)C(=O)C=2C=C1OC1=CC=CC=C1 UUTAORFVKHTLIB-UHFFFAOYSA-N 0.000 description 1
- YPJOAPMGRJDGJZ-UHFFFAOYSA-N n-(4-acetyl-5-methoxy-2-phenoxyphenyl)methanesulfonamide Chemical compound C1=C(C(C)=O)C(OC)=CC(NS(C)(=O)=O)=C1OC1=CC=CC=C1 YPJOAPMGRJDGJZ-UHFFFAOYSA-N 0.000 description 1
- JTAVNEZKQIBJTN-UHFFFAOYSA-N n-(4-oxo-6-phenoxy-2,3-dihydrochromen-7-yl)acetamide Chemical compound CC(=O)NC1=CC=2OCCC(=O)C=2C=C1OC1=CC=CC=C1 JTAVNEZKQIBJTN-UHFFFAOYSA-N 0.000 description 1
- FVIIKLZHGKCROV-UHFFFAOYSA-N n-(4-oxo-6-phenoxychromen-7-yl)ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=2OC=CC(=O)C=2C=C1OC1=CC=CC=C1 FVIIKLZHGKCROV-UHFFFAOYSA-N 0.000 description 1
- ARBUOUHQIYFAPN-UHFFFAOYSA-N n-(5-hydroxy-2-phenoxyphenyl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=CC(O)=CC=C1OC1=CC=CC=C1 ARBUOUHQIYFAPN-UHFFFAOYSA-N 0.000 description 1
- HKQJXMJGWKDFTA-UHFFFAOYSA-N n-(5-methoxy-2-phenoxyphenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(OC)=CC=C1OC1=CC=CC=C1 HKQJXMJGWKDFTA-UHFFFAOYSA-N 0.000 description 1
- MTYHYXZUZBZDQJ-UHFFFAOYSA-N n-(6-hydroxy-4-oxochromen-7-yl)methanesulfonamide Chemical compound O1C=CC(=O)C2=C1C=C(NS(=O)(=O)C)C(O)=C2 MTYHYXZUZBZDQJ-UHFFFAOYSA-N 0.000 description 1
- BDPQRRZXBVVCQO-UHFFFAOYSA-N n-[2-(2,4-difluorophenoxy)-5-hydroxyphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(O)=CC=C1OC1=CC=C(F)C=C1F BDPQRRZXBVVCQO-UHFFFAOYSA-N 0.000 description 1
- CJOFPCLZJXOOJW-UHFFFAOYSA-N n-[3-(ethylamino)-4-oxo-6-phenoxychromen-7-yl]methanesulfonamide Chemical compound C1=C2C(=O)C(NCC)=COC2=CC(NS(C)(=O)=O)=C1OC1=CC=CC=C1 CJOFPCLZJXOOJW-UHFFFAOYSA-N 0.000 description 1
- DOOZFLKLBQSDNK-UHFFFAOYSA-N n-[3-cyano-6-(2-fluorophenoxy)-4-oxochromen-7-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=2OC=C(C#N)C(=O)C=2C=C1OC1=CC=CC=C1F DOOZFLKLBQSDNK-UHFFFAOYSA-N 0.000 description 1
- DUQQHNZJVFSERJ-UHFFFAOYSA-N n-[4-acetyl-2-(2,4-difluorophenoxy)-5-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(C(=O)C)=CC(OC=2C(=CC(F)=CC=2)F)=C1NS(C)(=O)=O DUQQHNZJVFSERJ-UHFFFAOYSA-N 0.000 description 1
- YJSLRVBFBSMNOB-UHFFFAOYSA-N n-[5-hydroxy-2-(2-methoxyphenoxy)phenyl]methanesulfonamide Chemical compound COC1=CC=CC=C1OC1=CC=C(O)C=C1NS(C)(=O)=O YJSLRVBFBSMNOB-UHFFFAOYSA-N 0.000 description 1
- HAOPKNXYKDELFS-UHFFFAOYSA-N n-[5-methoxy-2-(3-methylphenoxy)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(OC)=CC=C1OC1=CC=CC(C)=C1 HAOPKNXYKDELFS-UHFFFAOYSA-N 0.000 description 1
- XTPAYVFKDMIUEN-UHFFFAOYSA-N n-[6-(2,4-difluorophenoxy)-4-oxochromen-7-yl]-n-methylsulfonylacetamide Chemical compound CC(=O)N(S(C)(=O)=O)C1=CC=2OC=CC(=O)C=2C=C1OC1=CC=C(F)C=C1F XTPAYVFKDMIUEN-UHFFFAOYSA-N 0.000 description 1
- SYUDVYBKMPRJOU-UHFFFAOYSA-N n-[6-(2-fluorophenoxy)-7-(methanesulfonamido)-4-oxochromen-3-yl]formamide Chemical compound CS(=O)(=O)NC1=CC=2OC=C(NC=O)C(=O)C=2C=C1OC1=CC=CC=C1F SYUDVYBKMPRJOU-UHFFFAOYSA-N 0.000 description 1
- PMJUZBWTGZOOGC-UHFFFAOYSA-N n-[7-(methanesulfonamido)-4-oxo-6-phenoxychromen-3-yl]-n-methylformamide Chemical compound C1=C2C(=O)C(N(C=O)C)=COC2=CC(NS(C)(=O)=O)=C1OC1=CC=CC=C1 PMJUZBWTGZOOGC-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- GXBJNMSTHMBPPE-UHFFFAOYSA-N quinolin-8-ol;hydrochloride Chemical compound Cl.C1=CN=C2C(O)=CC=CC2=C1 GXBJNMSTHMBPPE-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Chemical group 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- WRYRBZBPAFNIMX-UHFFFAOYSA-N sulfanide;triethylazanium Chemical compound S.CCN(CC)CC WRYRBZBPAFNIMX-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 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 1
- FUCBQMFTYFQCOB-UHFFFAOYSA-N trityl perchlorate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCl(=O)(=O)=O)C1=CC=CC=C1 FUCBQMFTYFQCOB-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
-
- 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]
-
- 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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 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 in position 2
-
- 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
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- 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
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
-
- 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
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
- C07D311/54—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 substituted in the carbocyclic ring
-
- 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
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
-
- 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
- C07D405/12—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 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
- C07D409/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP25425187 | 1987-10-08 | ||
JP25425187 | 1987-10-08 | ||
JP11999088 | 1988-05-17 | ||
JP11999088 | 1988-05-17 | ||
JP63250811A JPH0753725B2 (ja) | 1987-10-08 | 1988-10-06 | 4h―1―ベンゾピラン―4―オン誘導体およびその塩、それらの製造法並びにそれらを含有する抗炎症剤 |
JP25081188 | 1988-10-06 |
Publications (3)
Publication Number | Publication Date |
---|---|
NL8802464A NL8802464A (nl) | 1989-05-01 |
NL194914B NL194914B (nl) | 2003-03-03 |
NL194914C true NL194914C (nl) | 2003-07-04 |
Family
ID=27313952
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NL8802464A NL194914C (nl) | 1987-10-08 | 1988-10-07 | 4H-1-benzopyran-4-onderivaat of zout daarvan, en farmaceutisch preparaat dat dit als actieve stof bevat. |
Country Status (16)
Country | Link |
---|---|
US (1) | US4954518A (en, 2012) |
JP (1) | JPH0753725B2 (en, 2012) |
KR (1) | KR910007970B1 (en, 2012) |
AT (1) | AT397088B (en, 2012) |
AU (1) | AU605363B2 (en, 2012) |
BE (1) | BE1002226A5 (en, 2012) |
CA (1) | CA1320959C (en, 2012) |
CH (1) | CH679397A5 (en, 2012) |
DE (1) | DE3834204A1 (en, 2012) |
ES (8) | ES2013801A6 (en, 2012) |
FI (1) | FI98460C (en, 2012) |
FR (1) | FR2621585B1 (en, 2012) |
GB (1) | GB2210879B (en, 2012) |
IT (1) | IT1235048B (en, 2012) |
NL (1) | NL194914C (en, 2012) |
SE (1) | SE468595B (en, 2012) |
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CN101891726B (zh) * | 2005-10-09 | 2012-05-23 | 天津药物研究院 | 艾拉莫德结晶形态及其组合物 |
CN101885717B (zh) * | 2005-10-09 | 2012-05-23 | 天津药物研究院 | 艾拉莫德结晶形态及其组合物 |
CN101885718B (zh) * | 2005-10-09 | 2012-05-23 | 天津药物研究院 | 艾拉莫德结晶形态及其组合物 |
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PL2929880T3 (pl) * | 2013-07-18 | 2017-03-31 | Toyama Chemical Co., Ltd. | Środek terapeutyczny do leczenia choroby, wykazujący hamujący wpływ na czynnik hamujący migrację makrofagów |
CN107021891A (zh) * | 2017-04-24 | 2017-08-08 | 常州佳德医药科技有限公司 | 一种艾拉莫德中间体的制备方法 |
CN106986797B (zh) * | 2017-04-24 | 2018-09-28 | 常州佳德医药科技有限公司 | N-(2-(4-乙酰苯氧基)-5-甲氧基苯基)甲磺酰胺及其制备方法 |
CN111170914B (zh) * | 2018-11-09 | 2021-12-21 | 成都大学 | 硒/硫化磺酰芳胺类化合物及其硒/硫化方法 |
CN109705000A (zh) * | 2019-02-26 | 2019-05-03 | 南京红杉生物科技有限公司 | 艾拉莫德中间体及其合成方法 |
JP7453365B2 (ja) * | 2020-05-29 | 2024-03-19 | 富士フイルム富山化学株式会社 | 高純度のn-(5-メトキシ―2-フェノキシフェニル)メタンスルホンアミド及びその製造方法 |
CN113968836A (zh) * | 2020-07-25 | 2022-01-25 | 华创合成制药股份有限公司 | 一种苯并吡喃衍生物及其在类风湿性关节炎治疗中的应用 |
CN113968838B (zh) * | 2020-07-25 | 2024-04-02 | 华创合成制药股份有限公司 | 一种硫代苯并吡喃类化合物及其在类风湿性关节炎治疗中的应用 |
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-
1988
- 1988-10-06 JP JP63250811A patent/JPH0753725B2/ja not_active Expired - Lifetime
- 1988-10-07 BE BE8801158A patent/BE1002226A5/fr not_active IP Right Cessation
- 1988-10-07 GB GB8823567A patent/GB2210879B/en not_active Expired - Lifetime
- 1988-10-07 NL NL8802464A patent/NL194914C/nl not_active IP Right Cessation
- 1988-10-07 FR FR8813205A patent/FR2621585B1/fr not_active Expired - Lifetime
- 1988-10-07 AU AU23489/88A patent/AU605363B2/en not_active Expired
- 1988-10-07 CH CH3763/88A patent/CH679397A5/de not_active IP Right Cessation
- 1988-10-07 SE SE8803570A patent/SE468595B/sv not_active IP Right Cessation
- 1988-10-07 CA CA000579624A patent/CA1320959C/en not_active Expired - Lifetime
- 1988-10-07 FI FI884626A patent/FI98460C/fi not_active IP Right Cessation
- 1988-10-07 DE DE3834204A patent/DE3834204A1/de active Granted
- 1988-10-07 US US07/255,121 patent/US4954518A/en not_active Expired - Lifetime
- 1988-10-07 ES ES8803062A patent/ES2013801A6/es not_active Expired - Lifetime
- 1988-10-08 KR KR1019880013144A patent/KR910007970B1/ko not_active Expired
- 1988-10-10 AT AT0249588A patent/AT397088B/de not_active IP Right Cessation
- 1988-10-10 IT IT8848441A patent/IT1235048B/it active
-
1989
- 1989-10-13 ES ES8903467A patent/ES2017838A6/es not_active Expired - Lifetime
- 1989-10-13 ES ES8903465A patent/ES2018112A6/es not_active Expired - Lifetime
- 1989-10-13 ES ES8903469A patent/ES2018113A6/es not_active Expired - Lifetime
- 1989-10-13 ES ES8903463A patent/ES2018111A6/es not_active Expired - Lifetime
- 1989-10-13 ES ES8903468A patent/ES2017839A6/es not_active Expired - Lifetime
- 1989-10-13 ES ES8903464A patent/ES2017836A6/es not_active Expired - Lifetime
- 1989-10-13 ES ES8903466A patent/ES2017837A6/es not_active Expired - Lifetime
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