NO315652B1 - Substituerte benzoltienylpiperaziner, deres anvendelse som medikamenter, fremgangsmåter for fremstilling samt farmasöytiske sammensetningerinneholdende disse - Google Patents
Substituerte benzoltienylpiperaziner, deres anvendelse som medikamenter, fremgangsmåter for fremstilling samt farmasöytiske sammensetningerinneholdende disse Download PDFInfo
- Publication number
- NO315652B1 NO315652B1 NO19961077A NO961077A NO315652B1 NO 315652 B1 NO315652 B1 NO 315652B1 NO 19961077 A NO19961077 A NO 19961077A NO 961077 A NO961077 A NO 961077A NO 315652 B1 NO315652 B1 NO 315652B1
- Authority
- NO
- Norway
- Prior art keywords
- fluorobenzo
- compound
- thien
- hydrogen
- butyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000003814 drug Substances 0.000 title claims description 5
- 229940079593 drug Drugs 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- -1 benzothienylcarbonyl Chemical group 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 11
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 7
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- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
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- 239000012279 sodium borohydride Substances 0.000 claims description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
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- FBEGUWRRFMOUDH-UHFFFAOYSA-N 2-[2-[4-(6-fluoro-1-benzothiophen-3-yl)piperazin-1-yl]ethyl]-3-hydroxy-3h-isoindol-1-one Chemical compound O=C1C2=CC=CC=C2C(O)N1CCN1CCN(C=2C3=CC=C(F)C=C3SC=2)CC1 FBEGUWRRFMOUDH-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
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- MIBQYWIOHFTKHD-UHFFFAOYSA-N adamantane-1-carbonyl chloride Chemical compound C1C(C2)CC3CC2CC1(C(=O)Cl)C3 MIBQYWIOHFTKHD-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
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- 239000003610 charcoal Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
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- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
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- 239000002702 enteric coating Substances 0.000 description 1
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- RWLDAJMGAVDXSH-UHFFFAOYSA-N ethane-1,1,2-tricarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(O)=O RWLDAJMGAVDXSH-UHFFFAOYSA-N 0.000 description 1
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- 239000001530 fumaric acid Substances 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- 150000003951 lactams Chemical class 0.000 description 1
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- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
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- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000017311 musculoskeletal movement, spinal reflex action Effects 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FERZDALKDCSVRX-UHFFFAOYSA-M potassium;carbamate Chemical compound [K+].NC([O-])=O FERZDALKDCSVRX-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000012216 screening Methods 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
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41381895A | 1995-03-17 | 1995-03-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO961077D0 NO961077D0 (no) | 1996-03-15 |
| NO961077L NO961077L (no) | 1996-09-18 |
| NO315652B1 true NO315652B1 (no) | 2003-10-06 |
Family
ID=23638775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19961077A NO315652B1 (no) | 1995-03-17 | 1996-03-15 | Substituerte benzoltienylpiperaziner, deres anvendelse som medikamenter, fremgangsmåter for fremstilling samt farmasöytiske sammensetningerinneholdende disse |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5801176A (xx) |
| EP (1) | EP0732332B1 (xx) |
| JP (1) | JPH093060A (xx) |
| KR (1) | KR100402510B1 (xx) |
| CN (1) | CN1082959C (xx) |
| AT (1) | ATE211137T1 (xx) |
| AU (1) | AU700077B2 (xx) |
| CA (1) | CA2171695A1 (xx) |
| CZ (1) | CZ80496A3 (xx) |
| DE (1) | DE69618050T2 (xx) |
| DK (1) | DK0732332T3 (xx) |
| ES (1) | ES2170177T3 (xx) |
| HU (1) | HUP9600665A3 (xx) |
| IL (1) | IL117519A (xx) |
| NO (1) | NO315652B1 (xx) |
| NZ (1) | NZ286186A (xx) |
| PL (1) | PL182310B1 (xx) |
| PT (1) | PT732332E (xx) |
| RO (1) | RO117453B1 (xx) |
| RU (1) | RU2157371C2 (xx) |
| SG (1) | SG54269A1 (xx) |
| TW (1) | TW328957B (xx) |
| ZA (1) | ZA962075B (xx) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5703083A (en) * | 1996-04-15 | 1997-12-30 | Neurogen Corporation | N-aminoalkyl-1-biphenylenyl-2-carboxamides; new dopamine receptor subtype specific ligands |
| US6642228B1 (en) | 1999-06-24 | 2003-11-04 | Toray Industries, Inc. | α1b-adrenergic receptor antagonists |
| GB0117531D0 (en) * | 2001-02-16 | 2001-09-12 | Aventis Pharm Prod Inc | Novel heterocyclic amide derivatives and their use as dopamine D3 receptor ligands |
| JP4497815B2 (ja) * | 2001-02-16 | 2010-07-07 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | 新規な複素環式アミド誘導体およびドーパミンｄ３受容体リガンドとしてのその使用 |
| JP4497814B2 (ja) * | 2001-02-16 | 2010-07-07 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | 新規複素環式尿素誘導体およびドーパミンｄ３受容体リガンドとしてのそれらの使用 |
| EP1374855A1 (en) * | 2001-03-30 | 2004-01-02 | Takeda Chemical Industries, Ltd. | Medicinal solutions |
| TWI320783B (en) | 2005-04-14 | 2010-02-21 | Otsuka Pharma Co Ltd | Heterocyclic compound |
| TWI329641B (en) | 2005-08-31 | 2010-09-01 | Otsuka Pharma Co Ltd | (benzo[b]thiophen-4-yl)piperazine compounds, pharmaceutical compositions comprising the same, uses of the same and processes for preparing the same |
| CN105985314A (zh) * | 2015-02-05 | 2016-10-05 | 苏州旺山旺水生物医药有限公司 | 布瑞哌唑类似物的制备方法 |
| JPWO2021132311A1 (xx) * | 2019-12-24 | 2021-07-01 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK169601B1 (da) * | 1983-10-17 | 1994-12-19 | Duphar Int Res | Piperazinderivater og farmaceutisk præparat indeholdende et sådant derivat, samt piperazinderivater med mellemproduktanvendelse |
| EP0316723B1 (en) * | 1987-11-20 | 1992-09-30 | Hoechst-Roussel Pharmaceuticals Incorporated | 3-[4(1-Substituted-4-piperazinyl)butyl]-4-thiazolidinones a process for their preparation and their use as medicaments |
| US4780466A (en) * | 1988-03-17 | 1988-10-25 | Hoechst-Roussel Pharmaceuticals, Inc. | Arylpiperazinylalkoxy derivatives of cyclic imides |
| US5776963A (en) * | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
| US4968792A (en) * | 1989-09-25 | 1990-11-06 | American Home Products Corporation | Psychotropic benzisothiazole derivatives |
| US5143923B1 (en) * | 1991-04-29 | 1993-11-02 | Hoechst-Roussel Pharmaceuticals Incorporated | Benzoisothiazole-and benzisoxazole-3-carboxamides |
| GB9202915D0 (en) * | 1992-02-12 | 1992-03-25 | Wellcome Found | Chemical compounds |
| US5240927A (en) * | 1992-05-19 | 1993-08-31 | Hoechst-Roussel Pharmaceuticals Incorporated | Benzo[β]thiophen-3-yl piperazines as antipsychotic agents |
| GB9302622D0 (en) * | 1993-02-10 | 1993-03-24 | Wellcome Found | Heteroaromatic compounds |
| US5395835A (en) * | 1994-03-24 | 1995-03-07 | Warner-Lambert Company | Naphthalamides as central nervous system agents |
| GB9410031D0 (en) * | 1994-05-19 | 1994-07-06 | Merck Sharp & Dohme | Therapeutic agents |
-
1996
- 1996-03-11 EP EP96103772A patent/EP0732332B1/en not_active Expired - Lifetime
- 1996-03-11 ES ES96103772T patent/ES2170177T3/es not_active Expired - Lifetime
- 1996-03-11 AT AT96103772T patent/ATE211137T1/de not_active IP Right Cessation
- 1996-03-11 DK DK96103772T patent/DK0732332T3/da active
- 1996-03-11 DE DE69618050T patent/DE69618050T2/de not_active Expired - Fee Related
- 1996-03-11 PT PT96103772T patent/PT732332E/pt unknown
- 1996-03-12 SG SG1996006846A patent/SG54269A1/en unknown
- 1996-03-13 CA CA002171695A patent/CA2171695A1/en not_active Abandoned
- 1996-03-14 AU AU48113/96A patent/AU700077B2/en not_active Ceased
- 1996-03-14 HU HU9600665A patent/HUP9600665A3/hu unknown
- 1996-03-14 ZA ZA9602075A patent/ZA962075B/xx unknown
- 1996-03-14 PL PL96313251A patent/PL182310B1/pl unknown
- 1996-03-15 NZ NZ286186A patent/NZ286186A/en unknown
- 1996-03-15 JP JP8058707A patent/JPH093060A/ja not_active Abandoned
- 1996-03-15 CZ CZ96804A patent/CZ80496A3/cs unknown
- 1996-03-15 RU RU96104547/04A patent/RU2157371C2/ru not_active IP Right Cessation
- 1996-03-15 RO RO96-00568A patent/RO117453B1/ro unknown
- 1996-03-15 CN CN96103608A patent/CN1082959C/zh not_active Expired - Fee Related
- 1996-03-15 NO NO19961077A patent/NO315652B1/no not_active IP Right Cessation
- 1996-03-16 KR KR1019960007100A patent/KR100402510B1/ko not_active IP Right Cessation
- 1996-03-17 IL IL11751996A patent/IL117519A/xx not_active IP Right Cessation
- 1996-05-15 TW TW085105712A patent/TW328957B/zh active
-
1997
- 1997-06-06 US US08/870,988 patent/US5801176A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1139108A (zh) | 1997-01-01 |
| ATE211137T1 (de) | 2002-01-15 |
| JPH093060A (ja) | 1997-01-07 |
| EP0732332B1 (en) | 2001-12-19 |
| TW328957B (en) | 1998-04-01 |
| AU700077B2 (en) | 1998-12-17 |
| IL117519A0 (en) | 1996-07-23 |
| RU2157371C2 (ru) | 2000-10-10 |
| RO117453B1 (ro) | 2002-03-29 |
| DE69618050D1 (de) | 2002-01-31 |
| DE69618050T2 (de) | 2002-07-11 |
| KR100402510B1 (ko) | 2004-03-18 |
| ES2170177T3 (es) | 2002-08-01 |
| CA2171695A1 (en) | 1996-09-18 |
| CZ80496A3 (en) | 1996-10-16 |
| PT732332E (pt) | 2002-06-28 |
| DK0732332T3 (da) | 2002-04-15 |
| KR960034201A (ko) | 1996-10-22 |
| SG54269A1 (en) | 1998-11-16 |
| IL117519A (en) | 2000-08-31 |
| EP0732332A1 (en) | 1996-09-18 |
| HUP9600665A3 (en) | 1998-08-28 |
| NO961077L (no) | 1996-09-18 |
| NZ286186A (en) | 1997-07-27 |
| AU4811396A (en) | 1996-09-26 |
| ZA962075B (en) | 1997-12-31 |
| CN1082959C (zh) | 2002-04-17 |
| HUP9600665A2 (en) | 1997-10-28 |
| HU9600665D0 (en) | 1996-05-28 |
| NO961077D0 (no) | 1996-03-15 |
| PL182310B1 (pl) | 2001-12-31 |
| PL313251A1 (en) | 1996-09-30 |
| US5801176A (en) | 1998-09-01 |
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