SK7599A3 - Chroman derivatives and pharmaceutical composition containing the same - Google Patents
Chroman derivatives and pharmaceutical composition containing the same Download PDFInfo
- Publication number
- SK7599A3 SK7599A3 SK75-99A SK7599A SK7599A3 SK 7599 A3 SK7599 A3 SK 7599A3 SK 7599 A SK7599 A SK 7599A SK 7599 A3 SK7599 A3 SK 7599A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- alkyl
- optionally substituted
- carbon atoms
- hydroxyl
- Prior art date
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- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title claims abstract 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 72
- 125000005843 halogen group Chemical group 0.000 claims abstract description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 24
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 24
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 19
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 8
- -1 cyano, formyl Chemical group 0.000 claims description 324
- 150000001875 compounds Chemical class 0.000 claims description 309
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 181
- 125000004432 carbon atom Chemical group C* 0.000 claims description 120
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 117
- 125000000217 alkyl group Chemical group 0.000 claims description 105
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 45
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 39
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 22
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 10
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 206010019280 Heart failures Diseases 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 9
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 9
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 8
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 5
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000004849 alkoxymethyl group Chemical group 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 115
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 111
- 239000002904 solvent Substances 0.000 description 97
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 90
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 59
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 238000000034 method Methods 0.000 description 23
- 150000001843 chromanes Chemical class 0.000 description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 19
- 239000003814 drug Substances 0.000 description 17
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 150000002431 hydrogen Chemical group 0.000 description 14
- 239000012442 inert solvent Substances 0.000 description 14
- 150000003462 sulfoxides Chemical class 0.000 description 14
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 13
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 13
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
- 239000004210 ether based solvent Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000003849 aromatic solvent Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 9
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 210000002216 heart Anatomy 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000013543 active substance Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000005456 alcohol based solvent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- WEYDYKHFODVPIK-UHFFFAOYSA-N (4-methoxyphenyl)methylurea Chemical compound COC1=CC=C(CNC(N)=O)C=C1 WEYDYKHFODVPIK-UHFFFAOYSA-N 0.000 description 5
- 125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- RYOCWONLFFPYMN-UHFFFAOYSA-N tert-butylthiourea Chemical compound CC(C)(C)NC(N)=S RYOCWONLFFPYMN-UHFFFAOYSA-N 0.000 description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 4
- 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 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 210000004165 myocardium Anatomy 0.000 description 4
- SQKIZTPMVWJSLG-UHFFFAOYSA-N n-(2,2-dimethyl-5-nitro-1a,7b-dihydrooxireno[2,3-c]chromen-6-yl)-2-phenylacetamide Chemical compound C1=C2C3OC3C(C)(C)OC2=CC([N+]([O-])=O)=C1NC(=O)CC1=CC=CC=C1 SQKIZTPMVWJSLG-UHFFFAOYSA-N 0.000 description 4
- QKLSFAVXZOMRGP-UHFFFAOYSA-N n-(2,2-dimethyl-5-nitro-1a,7b-dihydrooxireno[2,3-c]chromen-6-yl)benzamide Chemical compound C1=C2C3OC3C(C)(C)OC2=CC([N+]([O-])=O)=C1NC(=O)C1=CC=CC=C1 QKLSFAVXZOMRGP-UHFFFAOYSA-N 0.000 description 4
- ZGROZVHFENRYAI-UHFFFAOYSA-N n-(2,2-dimethyl-7-nitrochromen-6-yl)benzamide Chemical compound C1=C2C=CC(C)(C)OC2=CC([N+]([O-])=O)=C1NC(=O)C1=CC=CC=C1 ZGROZVHFENRYAI-UHFFFAOYSA-N 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
- JSPQBFOFUCKECH-UHFFFAOYSA-N (3-amino-2,2-dimethyl-7-nitrochromen-6-yl)-(4-hydroxyphenyl)methanone Chemical compound OC1=CC=C(C(=O)C=2C(=CC3=C(C=C(C(O3)(C)C)N)C=2)[N+](=O)[O-])C=C1 JSPQBFOFUCKECH-UHFFFAOYSA-N 0.000 description 3
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 210000001367 artery Anatomy 0.000 description 3
- 150000001562 benzopyrans Chemical class 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 3
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- ASDUTYZHLDZCEG-UHFFFAOYSA-N naphthalen-1-ylmethylthiourea Chemical compound C1=CC=C2C(CNC(=S)N)=CC=CC2=C1 ASDUTYZHLDZCEG-UHFFFAOYSA-N 0.000 description 1
- FVSUYFWWFUVGRG-UHFFFAOYSA-N naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)N)=CC=CC2=C1 FVSUYFWWFUVGRG-UHFFFAOYSA-N 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- KIYXXKTUEPCNLC-UHFFFAOYSA-N pentylthiourea Chemical compound CCCCCNC(N)=S KIYXXKTUEPCNLC-UHFFFAOYSA-N 0.000 description 1
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- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- 230000033764 rhythmic process Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
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- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical class C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
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- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- JLEHSYHLHLHPAL-UHFFFAOYSA-N tert-butylurea Chemical compound CC(C)(C)NC(N)=O JLEHSYHLHLHPAL-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- BKEOXUSOEGMVTL-UHFFFAOYSA-N trimethyl-$l^{3}-bromane Chemical compound CBr(C)C BKEOXUSOEGMVTL-UHFFFAOYSA-N 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
-
- 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
- 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
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
-
- 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
- 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
- C07D409/12—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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19781996 | 1996-07-26 | ||
| PCT/JP1997/002583 WO1998004542A1 (en) | 1996-07-26 | 1997-07-25 | Chroman derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK7599A3 true SK7599A3 (en) | 1999-07-12 |
Family
ID=16380875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK75-99A SK7599A3 (en) | 1996-07-26 | 1997-07-25 | Chroman derivatives and pharmaceutical composition containing the same |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6066631A (xx) |
| EP (1) | EP0934296B1 (xx) |
| KR (1) | KR20000023843A (xx) |
| CN (1) | CN1226243A (xx) |
| AT (1) | ATE242230T1 (xx) |
| AU (1) | AU713573B2 (xx) |
| CA (1) | CA2261143A1 (xx) |
| CZ (1) | CZ24499A3 (xx) |
| DE (1) | DE69722644T2 (xx) |
| HU (1) | HUP9902456A3 (xx) |
| IL (1) | IL128170A0 (xx) |
| LT (1) | LT4578B (xx) |
| NO (1) | NO990265L (xx) |
| NZ (1) | NZ333870A (xx) |
| SK (1) | SK7599A3 (xx) |
| TW (1) | TW491844B (xx) |
| WO (1) | WO1998004542A1 (xx) |
| ZA (1) | ZA976654B (xx) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998004542A1 (en) * | 1996-07-26 | 1998-02-05 | Nissan Chemical Industries, Ltd. | Chroman derivatives |
| DE19730989A1 (de) * | 1997-07-18 | 1999-01-21 | Merck Patent Gmbh | Piperazin-Derivate |
| CA2334412A1 (en) * | 1998-06-03 | 1999-12-09 | Nissan Chemical Industries, Ltd. | Indan derivatives |
| ATE311378T1 (de) | 1999-09-17 | 2005-12-15 | Nissan Chemical Ind Ltd | Benzopyran derivate |
| GB0315950D0 (en) | 2003-06-11 | 2003-08-13 | Xention Discovery Ltd | Compounds |
| WO2005037830A1 (en) | 2003-10-10 | 2005-04-28 | Wyeth | Piperidinylchromen-6-ylsulfonamide compounds as 5-hydroxytryptamine-6 ligands |
| TWI346112B (en) | 2004-02-25 | 2011-08-01 | Nissan Chemical Ind Ltd | Benzopyran compound |
| GB0412986D0 (en) | 2004-06-10 | 2004-07-14 | Xention Discovery Ltd | Compounds |
| US7576212B2 (en) | 2004-12-09 | 2009-08-18 | Xention Limited | Thieno[2,3-B] pyridines as potassium channel inhibitors |
| GB0525164D0 (en) | 2005-12-09 | 2006-01-18 | Xention Discovery Ltd | Compounds |
| GB0815782D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815784D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815781D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB201105659D0 (en) | 2011-04-01 | 2011-05-18 | Xention Ltd | Compounds |
| NO3175985T3 (xx) | 2011-07-01 | 2018-04-28 | ||
| WO2013112932A1 (en) | 2012-01-27 | 2013-08-01 | Gilead Sciences, Inc. | Combination therapies using late sodium ion channel blockers and potassium ion channel blockers |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1495526A (en) * | 1974-05-31 | 1977-12-21 | Beecham Group Ltd | Chroman derivatives |
| JPS5657786A (en) * | 1979-09-28 | 1981-05-20 | Beecham Group Ltd | Chromanol derivative* its manufacture and medicinal composition containing it |
| DE3064286D1 (en) * | 1979-09-28 | 1983-08-25 | Beecham Group Plc | Chromanol derivatives, a process for their preparation and a pharmaceutical composition comprising them |
| JPS5657785A (en) * | 1979-09-28 | 1981-05-20 | Beecham Group Ltd | Chromanol derivative* its manufacture and medicinal composition containing it |
| ZM7682A1 (en) * | 1981-09-25 | 1983-05-23 | Beecham Group Plc | Active compounds |
| DE3364145D1 (de) * | 1982-04-08 | 1986-07-24 | Beecham Group Plc | Antihypertensive benzopyranols |
| EP0093535B1 (en) * | 1982-04-28 | 1986-12-30 | Beecham Group Plc | Novel chromenes and chromans |
| GB8324547D0 (en) | 1983-09-14 | 1983-10-19 | Beecham Group Plc | Compounds |
| JP2876712B2 (ja) * | 1989-07-17 | 1999-03-31 | 日産化学工業株式会社 | 光学活性ピラノベンゾオキサジアゾール誘導体 |
| US5097037A (en) * | 1989-07-17 | 1992-03-17 | Nissan Chemical Industries, Ltd. | Process for the optical resolution of pyranobenzoxadiazole compounds |
| ES2113374T3 (es) | 1990-03-21 | 1998-05-01 | Res Corp Technologies Inc | Catalizadores quirales y reacciones de epoxidacion catalizadas por los mismos. |
| JPH05301878A (ja) * | 1991-08-30 | 1993-11-16 | Nissan Chem Ind Ltd | 不斉エポキシ化反応 |
| US5352814A (en) * | 1991-08-30 | 1994-10-04 | Nissan Chemical Industries, Ltd. | Asymmetric epoxidation reaction |
| JP3323292B2 (ja) | 1993-07-07 | 2002-09-09 | 日本無線株式会社 | レーダ画像真位置計測装置 |
| JP2734457B2 (ja) * | 1994-02-23 | 1998-03-30 | 日産化学工業株式会社 | 不斉エポキシ化反応 |
| ES2156880T3 (es) * | 1994-02-23 | 2001-08-01 | Nissan Chemical Ind Ltd | Procedimiento de epoxidacion asimetrica utilizando complejos de manganeso opticamente activos. |
| WO1997023209A1 (fr) * | 1995-12-25 | 1997-07-03 | Nissan Chemical Industries, Ltd. | Agent therapeutique contre l'insuffisance cardiaque |
| WO1998004542A1 (en) * | 1996-07-26 | 1998-02-05 | Nissan Chemical Industries, Ltd. | Chroman derivatives |
-
1997
- 1997-07-25 WO PCT/JP1997/002583 patent/WO1998004542A1/en not_active Application Discontinuation
- 1997-07-25 IL IL12817097A patent/IL128170A0/xx unknown
- 1997-07-25 AU AU36349/97A patent/AU713573B2/en not_active Ceased
- 1997-07-25 EP EP97933023A patent/EP0934296B1/en not_active Expired - Lifetime
- 1997-07-25 CZ CZ99244A patent/CZ24499A3/cs unknown
- 1997-07-25 DE DE69722644T patent/DE69722644T2/de not_active Expired - Fee Related
- 1997-07-25 CN CN97196736A patent/CN1226243A/zh active Pending
- 1997-07-25 AT AT97933023T patent/ATE242230T1/de not_active IP Right Cessation
- 1997-07-25 NZ NZ333870A patent/NZ333870A/xx unknown
- 1997-07-25 ZA ZA9706654A patent/ZA976654B/xx unknown
- 1997-07-25 CA CA002261143A patent/CA2261143A1/en not_active Abandoned
- 1997-07-25 TW TW086110615A patent/TW491844B/zh active
- 1997-07-25 SK SK75-99A patent/SK7599A3/sk unknown
- 1997-07-25 HU HU9902456A patent/HUP9902456A3/hu unknown
-
1999
- 1999-01-18 KR KR1019997000359A patent/KR20000023843A/ko not_active Application Discontinuation
- 1999-01-19 US US09/232,645 patent/US6066631A/en not_active Expired - Fee Related
- 1999-01-21 NO NO990265A patent/NO990265L/no not_active Application Discontinuation
- 1999-02-23 LT LT99-017A patent/LT4578B/lt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US6066631A (en) | 2000-05-23 |
| EP0934296B1 (en) | 2003-06-04 |
| ZA976654B (en) | 1998-02-10 |
| CN1226243A (zh) | 1999-08-18 |
| AU3634997A (en) | 1998-02-20 |
| ATE242230T1 (de) | 2003-06-15 |
| CA2261143A1 (en) | 1998-02-05 |
| NO990265D0 (no) | 1999-01-21 |
| DE69722644D1 (de) | 2003-07-10 |
| WO1998004542A1 (en) | 1998-02-05 |
| NO990265L (no) | 1999-03-25 |
| AU713573B2 (en) | 1999-12-02 |
| EP0934296A1 (en) | 1999-08-11 |
| IL128170A0 (en) | 1999-11-30 |
| TW491844B (en) | 2002-06-21 |
| NZ333870A (en) | 2000-08-25 |
| HUP9902456A3 (en) | 2002-04-29 |
| LT99017A (en) | 1999-07-26 |
| DE69722644T2 (de) | 2004-05-06 |
| CZ24499A3 (cs) | 1999-05-12 |
| KR20000023843A (ko) | 2000-04-25 |
| LT4578B (lt) | 1999-11-25 |
| HUP9902456A2 (hu) | 2001-05-28 |
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