ES2204932T3 - Moduladores serotonergicos. - Google Patents
Moduladores serotonergicos.Info
- Publication number
- ES2204932T3 ES2204932T3 ES95306253T ES95306253T ES2204932T3 ES 2204932 T3 ES2204932 T3 ES 2204932T3 ES 95306253 T ES95306253 T ES 95306253T ES 95306253 T ES95306253 T ES 95306253T ES 2204932 T3 ES2204932 T3 ES 2204932T3
- Authority
- ES
- Spain
- Prior art keywords
- hydrogen
- alkyl
- optionally substituted
- indole
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000000862 serotonergic effect Effects 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 239000001257 hydrogen Substances 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 14
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 150000002148 esters Chemical group 0.000 abstract description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 4
- ZITFWUUYPONCCK-UHFFFAOYSA-N 1,2,3,4,5,6-hexachlorocyclohexane;naphthalen-1-yl n-methylcarbamate Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl.C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 ZITFWUUYPONCCK-UHFFFAOYSA-N 0.000 abstract 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical group [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 25
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 239000007787 solid Substances 0.000 description 20
- -1 with inorganic acids Chemical class 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ONYNOPPOVKYGRS-UHFFFAOYSA-N 6-methyl-1h-indole Chemical compound CC1=CC=C2C=CNC2=C1 ONYNOPPOVKYGRS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PNWRVMPHOHSCJK-UHFFFAOYSA-N 3-(1-chloroethyl)-1h-benzimidazol-2-one Chemical compound C1=CC=C2NC(=O)N(C(Cl)C)C2=C1 PNWRVMPHOHSCJK-UHFFFAOYSA-N 0.000 description 3
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical compound N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YPKDMMCPRSIWAO-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3,3-dimethylindol-2-one Chemical compound C1=CC=C2C(C)(C)C(=O)N(CCO)C2=C1 YPKDMMCPRSIWAO-UHFFFAOYSA-N 0.000 description 2
- WRMZOPANDOHWJU-UHFFFAOYSA-N 1h-indol-6-ylmethanol Chemical compound OCC1=CC=C2C=CNC2=C1 WRMZOPANDOHWJU-UHFFFAOYSA-N 0.000 description 2
- RPROHCOBMVQVIV-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CCNC2 RPROHCOBMVQVIV-UHFFFAOYSA-N 0.000 description 2
- XJYQPQDGMMMFKP-UHFFFAOYSA-N 2-(2-oxo-1,3-benzothiazol-3-yl)ethyl methanesulfonate Chemical compound C1=CC=C2SC(=O)N(CCOS(=O)(=O)C)C2=C1 XJYQPQDGMMMFKP-UHFFFAOYSA-N 0.000 description 2
- XUEZJCGJEFCVSJ-UHFFFAOYSA-N 2-(2-oxo-1,3-benzoxazol-3-yl)ethyl methanesulfonate Chemical compound C1=CC=C2OC(=O)N(CCOS(=O)(=O)C)C2=C1 XUEZJCGJEFCVSJ-UHFFFAOYSA-N 0.000 description 2
- MPVLZNCQMXSBFM-UHFFFAOYSA-N 3,3-dimethyl-1-[2-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)ethyl]indol-2-one Chemical compound C12=CC=CC=C2C(C)(C)C(=O)N1CCN1CC(NC=2C3=CC=CC=2)=C3CC1 MPVLZNCQMXSBFM-UHFFFAOYSA-N 0.000 description 2
- SFTJKCPNRHYWEO-UHFFFAOYSA-N 3-(2-chloroethyl)-1h-benzimidazol-2-one Chemical compound C1=CC=C2NC(=O)N(CCCl)C2=C1 SFTJKCPNRHYWEO-UHFFFAOYSA-N 0.000 description 2
- IYIUFYCBSLRAAL-UHFFFAOYSA-N 3-[2-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)ethyl]-1h-benzimidazol-2-one Chemical compound N1C2=CC=CC=C2C(CC2)=C1CN2CCN1C2=CC=CC=C2NC1=O IYIUFYCBSLRAAL-UHFFFAOYSA-N 0.000 description 2
- DGCRRYPJCXBLSC-UHFFFAOYSA-N 4-(1-chloroethyl)benzimidazol-2-one Chemical compound CC(Cl)C1=CC=CC2=NC(=O)N=C12 DGCRRYPJCXBLSC-UHFFFAOYSA-N 0.000 description 2
- WFOAZAKVBMIMKT-UHFFFAOYSA-N 6-fluoro-2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole Chemical compound C1NCCC2=C1C(C=CC=C1F)=C1N2 WFOAZAKVBMIMKT-UHFFFAOYSA-N 0.000 description 2
- LZERQSJGPXFAKB-UHFFFAOYSA-N 6-methyl-1h-indole-3-carbaldehyde Chemical compound CC1=CC=C2C(C=O)=CNC2=C1 LZERQSJGPXFAKB-UHFFFAOYSA-N 0.000 description 2
- WZOXNYYEBXHSGC-UHFFFAOYSA-N 7-fluoro-2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole Chemical compound C1NCCC2=C1C1=CC=C(F)C=C1N2 WZOXNYYEBXHSGC-UHFFFAOYSA-N 0.000 description 2
- MNWNSXZHWSTXTC-UHFFFAOYSA-N 8-fluoro-2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole Chemical compound C1CNCC2=C1NC1=CC=C(F)C=C12 MNWNSXZHWSTXTC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
- LPIJOZBIVDCQTE-UHFFFAOYSA-N tetrahydroharman Chemical compound N1C2=CC=CC=C2C2=C1C(C)NCC2 LPIJOZBIVDCQTE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- PENWGQNPFRRVQI-UHFFFAOYSA-N (2-fluorophenyl)hydrazine Chemical compound NNC1=CC=CC=C1F PENWGQNPFRRVQI-UHFFFAOYSA-N 0.000 description 1
- YDMMOMJBRGJMJS-UHFFFAOYSA-N (2-methyl-1H-indol-6-yl) formate Chemical compound C(=O)OC1=CC=C2C=C(NC2=C1)C YDMMOMJBRGJMJS-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- SKVGLOFWEJFQKU-UHFFFAOYSA-N (3-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(F)=C1 SKVGLOFWEJFQKU-UHFFFAOYSA-N 0.000 description 1
- FEKUXLUOKFSMRO-UHFFFAOYSA-N (4-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(F)C=C1 FEKUXLUOKFSMRO-UHFFFAOYSA-N 0.000 description 1
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Anesthesiology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Otolaryngology (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Optical Integrated Circuits (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9418326A GB9418326D0 (en) | 1994-09-12 | 1994-09-12 | Pharmaceutical compounds |
| GB9418326 | 1994-09-12 | ||
| GBGB9511166.2A GB9511166D0 (en) | 1995-06-02 | 1995-06-02 | Pharmaceutical compounds |
| GB9511166 | 1995-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2204932T3 true ES2204932T3 (es) | 2004-05-01 |
Family
ID=26305611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES95306253T Expired - Lifetime ES2204932T3 (es) | 1994-09-12 | 1995-09-07 | Moduladores serotonergicos. |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0705832B1 (OSRAM) |
| JP (1) | JPH0881464A (OSRAM) |
| KR (1) | KR960010635A (OSRAM) |
| CN (1) | CN1045602C (OSRAM) |
| AT (1) | ATE247114T1 (OSRAM) |
| AU (1) | AU698580B2 (OSRAM) |
| CA (1) | CA2157998A1 (OSRAM) |
| CZ (1) | CZ286565B6 (OSRAM) |
| DE (1) | DE69531476T2 (OSRAM) |
| ES (1) | ES2204932T3 (OSRAM) |
| FI (1) | FI954243A7 (OSRAM) |
| HU (1) | HU219491B (OSRAM) |
| IL (1) | IL115236A (OSRAM) |
| IN (1) | IN179550B (OSRAM) |
| MY (1) | MY132009A (OSRAM) |
| NO (1) | NO305174B1 (OSRAM) |
| NZ (1) | NZ272961A (OSRAM) |
| PE (1) | PE41796A1 (OSRAM) |
| PH (1) | PH31631A (OSRAM) |
| PL (1) | PL310373A1 (OSRAM) |
| RU (1) | RU2146256C1 (OSRAM) |
| TR (1) | TR199501114A2 (OSRAM) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2308362A (en) * | 1995-12-19 | 1997-06-25 | Lilly Industries Ltd | Pharmaceutical indole derivatives |
| EP0905136A1 (en) * | 1997-09-08 | 1999-03-31 | Janssen Pharmaceutica N.V. | Tetrahydro gamma-carbolines |
| UA70334C2 (en) * | 1998-10-06 | 2004-10-15 | Janssen Pharmaceutica N V Jans | BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS |
| UA74826C2 (en) * | 2000-05-17 | 2006-02-15 | Ortho Mcneil Pharm Inc | ?-carboline derivatives as phosphodiesterase inhibitors |
| CA2415815A1 (en) * | 2000-07-06 | 2002-01-17 | Nigel H. Greig | Tetrahydrobenzothiazole analogues as neuroprotective agents |
| DE10040016A1 (de) * | 2000-08-16 | 2002-02-28 | Boehringer Ingelheim Pharma | Neue beta-Amyloid Inhibitoren, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| MXPA03002370A (es) * | 2000-09-19 | 2003-10-15 | Boehringer Ingelheim Pharma | Nuevos derivados bencimidazolona n,n'-disustituidos con afinidad en los receptores de serotonina y dopamina. |
| US6586435B2 (en) | 2000-09-19 | 2003-07-01 | Boehringer Ingelheim Pharma Kg | Benzimidazolone derivatives displaying affinity at the serotonin and dopamine receptors |
| ATE341538T1 (de) * | 2000-09-19 | 2006-10-15 | Boehringer Ingelheim Pharma | Benzimidazolonderivate mit affinität zu serotonin-und dopaminrezeptoren |
| US7183410B2 (en) | 2001-08-02 | 2007-02-27 | Bidachem S.P.A. | Stable polymorph of flibanserin |
| ATE306486T1 (de) * | 2001-08-08 | 2005-10-15 | Pharmacia & Upjohn Co Llc | Therapeutische 1h-pyrido(4,3-b)indole |
| US10675280B2 (en) | 2001-10-20 | 2020-06-09 | Sprout Pharmaceuticals, Inc. | Treating sexual desire disorders with flibanserin |
| UA78974C2 (en) | 2001-10-20 | 2007-05-10 | Boehringer Ingelheim Pharma | Use of flibanserin for treating disorders of sexual desire |
| RU2232578C1 (ru) * | 2003-04-10 | 2004-07-20 | Ахапкина Валентина Ивановна | Вещество, обладающее антидепрессивной активностью |
| US8227476B2 (en) | 2005-08-03 | 2012-07-24 | Sprout Pharmaceuticals, Inc. | Use of flibanserin in the treatment of obesity |
| EP1945214A1 (en) | 2005-10-29 | 2008-07-23 | Boehringer Ingelheim International GmbH | Benzimidazolone derivatives for the treatment of premenstrual and other female sexual disorders |
| ES2336719T3 (es) | 2006-06-30 | 2010-04-15 | Boehringer Ingelheim International Gmbh | Flibanserina para el tratamiento de la incontinencia urinaria y las enfermedades relacionadas. |
| CL2007002214A1 (es) | 2006-08-14 | 2008-03-07 | Boehringer Ingelheim Int | Composicion farmaceutica en la forma de comprimido, donde al menos la longitud del comprimido en el estado anterior de la aplicacion es al menos 7/12 del diametro pilorico del paciente y despues de ingerirlo en estado alimentado, la longitud del comp |
| JP5793828B2 (ja) | 2006-08-14 | 2015-10-14 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | フリバンセリンの製剤及びその製造方法 |
| AR062321A1 (es) | 2006-08-25 | 2008-10-29 | Boehringer Ingelheim Int | Sistema de liberacion controlada y metodo para fabricarlo |
| PE20091188A1 (es) | 2007-09-12 | 2009-08-31 | Boehringer Ingelheim Int | Compuesto 1-[2-(4-(3-trifluorometil-fenil)piperazin-1-il)etil]-2,3-dihidro-1h-benzimidazol-2-ona (flibanserina), sus sales de adicion y composiciones farmaceuticas que los contienen |
| WO2010137349A1 (ja) * | 2009-05-29 | 2010-12-02 | 住友化学株式会社 | 神経栄養因子の活性が関与する疾患の治療または予防剤 |
| BR122023020677A2 (pt) | 2015-10-01 | 2023-12-12 | Olema Pharmaceuticals, Inc. | Compostos de tetra-hidro-1h-pirido[3,4-b]indol, composições compreendendo os referidos compostos e usos dos mesmos |
| WO2021007146A1 (en) | 2019-07-07 | 2021-01-14 | Olema Pharmaceuticals, Inc. | Regimens of estrogen receptor antagonists |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4035369A (en) | 1975-10-08 | 1977-07-12 | Janssen Pharmaceutica N.V. | 1-Benzazolylalkyl-4-substituted-piperidines |
| IL69132A (en) * | 1982-07-14 | 1986-02-28 | Roussel Uclaf | Benzo-and naphtho-thiopyranopyrimidinones,their preparation and pharmaceutical compositions containing them |
| US4636563A (en) * | 1985-09-16 | 1987-01-13 | American Home Products Corporation | Antipsychotic γ-carbolines |
| FR2661177A1 (fr) * | 1990-04-23 | 1991-10-25 | Rhone Poulenc Sante | Derives du naphtosultame antagonistes de la serotonine, leur preparation et les medicaments les contenant. |
-
1995
- 1995-09-07 EP EP95306253A patent/EP0705832B1/en not_active Expired - Lifetime
- 1995-09-07 AT AT95306253T patent/ATE247114T1/de not_active IP Right Cessation
- 1995-09-07 DE DE69531476T patent/DE69531476T2/de not_active Expired - Fee Related
- 1995-09-07 ES ES95306253T patent/ES2204932T3/es not_active Expired - Lifetime
- 1995-09-08 MY MYPI95002675A patent/MY132009A/en unknown
- 1995-09-08 NZ NZ272961A patent/NZ272961A/en unknown
- 1995-09-08 PH PH51266A patent/PH31631A/en unknown
- 1995-09-08 HU HU9502631A patent/HU219491B/hu not_active IP Right Cessation
- 1995-09-08 AU AU30497/95A patent/AU698580B2/en not_active Ceased
- 1995-09-08 CZ CZ19952322A patent/CZ286565B6/cs not_active IP Right Cessation
- 1995-09-11 KR KR1019950029475A patent/KR960010635A/ko not_active Ceased
- 1995-09-11 PL PL95310373A patent/PL310373A1/xx unknown
- 1995-09-11 FI FI954243A patent/FI954243A7/fi unknown
- 1995-09-11 CN CN95117133A patent/CN1045602C/zh not_active Expired - Fee Related
- 1995-09-11 RU RU95115522A patent/RU2146256C1/ru active
- 1995-09-11 NO NO953575A patent/NO305174B1/no not_active IP Right Cessation
- 1995-09-11 IN IN1079CA1995 patent/IN179550B/en unknown
- 1995-09-11 JP JP7231873A patent/JPH0881464A/ja active Pending
- 1995-09-11 IL IL115236A patent/IL115236A/en not_active IP Right Cessation
- 1995-09-11 CA CA002157998A patent/CA2157998A1/en not_active Abandoned
- 1995-09-12 TR TR95/01114A patent/TR199501114A2/xx unknown
- 1995-09-12 PE PE1995278830A patent/PE41796A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CZ286565B6 (cs) | 2000-05-17 |
| EP0705832B1 (en) | 2003-08-13 |
| AU3049795A (en) | 1996-03-28 |
| EP0705832A1 (en) | 1996-04-10 |
| FI954243A7 (fi) | 1996-03-13 |
| TR199501114A2 (tr) | 1996-10-21 |
| AU698580B2 (en) | 1998-11-05 |
| NZ272961A (en) | 1998-02-26 |
| NO953575D0 (no) | 1995-09-11 |
| DE69531476T2 (de) | 2004-06-09 |
| CZ232295A3 (en) | 1996-03-13 |
| CA2157998A1 (en) | 1996-03-13 |
| HU219491B (hu) | 2001-04-28 |
| DE69531476D1 (de) | 2003-09-18 |
| RU2146256C1 (ru) | 2000-03-10 |
| IL115236A0 (en) | 1995-12-31 |
| CN1129219A (zh) | 1996-08-21 |
| NO953575L (no) | 1996-03-13 |
| PH31631A (en) | 1999-01-12 |
| MY132009A (en) | 2007-09-28 |
| CN1045602C (zh) | 1999-10-13 |
| HUT72593A (en) | 1996-05-28 |
| PL310373A1 (en) | 1996-03-18 |
| KR960010635A (ko) | 1996-04-20 |
| NO305174B1 (no) | 1999-04-12 |
| IL115236A (en) | 1998-06-15 |
| PE41796A1 (es) | 1996-10-21 |
| ATE247114T1 (de) | 2003-08-15 |
| JPH0881464A (ja) | 1996-03-26 |
| IN179550B (OSRAM) | 1997-10-18 |
| HU9502631D0 (en) | 1995-11-28 |
| FI954243A0 (fi) | 1995-09-11 |
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