NO311027B1 - Alkylaminobenzotiazol og -benzoksazolderivater - Google Patents
Alkylaminobenzotiazol og -benzoksazolderivater Download PDFInfo
- Publication number
- NO311027B1 NO311027B1 NO19985227A NO985227A NO311027B1 NO 311027 B1 NO311027 B1 NO 311027B1 NO 19985227 A NO19985227 A NO 19985227A NO 985227 A NO985227 A NO 985227A NO 311027 B1 NO311027 B1 NO 311027B1
- Authority
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- Norway
- Prior art keywords
- formula
- compound
- compounds
- alkyl
- dopamine
- Prior art date
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- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 129
- 239000000203 mixture Substances 0.000 claims description 60
- 239000002904 solvent Substances 0.000 claims description 41
- 102000003962 Dopamine D4 receptors Human genes 0.000 claims description 37
- 108090000357 Dopamine D4 receptors Proteins 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 19
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 239000012442 inert solvent Substances 0.000 claims description 13
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- 238000011282 treatment Methods 0.000 claims description 10
- 230000003042 antagnostic effect Effects 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
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- 239000004480 active ingredient Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
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- 210000000056 organ Anatomy 0.000 claims description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 239000012620 biological material Substances 0.000 claims description 4
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
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- FHWYOFCYSFHXDS-UHFFFAOYSA-N n-[2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl]-1,3-benzothiazol-2-amine Chemical compound C1=CC(Cl)=CC=C1N1CCN(CCNC=2SC3=CC=CC=C3N=2)CC1 FHWYOFCYSFHXDS-UHFFFAOYSA-N 0.000 description 1
- SQQQAJILYVEUFG-UHFFFAOYSA-N n-[2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl]-7-methoxy-1,3-benzothiazol-2-amine;hydrochloride Chemical compound Cl.S1C=2C(OC)=CC=CC=2N=C1NCCN(CC1)CCN1C1=CC=C(Cl)C=C1 SQQQAJILYVEUFG-UHFFFAOYSA-N 0.000 description 1
- NHYYKVOAPGFKHL-UHFFFAOYSA-N n-[3-(4-phenylpiperazin-1-yl)propyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NCCCN(CC1)CCN1C1=CC=CC=C1 NHYYKVOAPGFKHL-UHFFFAOYSA-N 0.000 description 1
- AJYSDQBKCRYQNF-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenyl)piperazin-1-yl]propyl]-6-methoxy-1,3-benzothiazol-2-amine;dihydrochloride Chemical compound Cl.Cl.S1C2=CC(OC)=CC=C2N=C1NCCCN(CC1)CCN1C1=CC=C(Cl)C(Cl)=C1 AJYSDQBKCRYQNF-UHFFFAOYSA-N 0.000 description 1
- ODJJJYLWJQCPDH-UHFFFAOYSA-N n-[3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propyl]-1,3-benzothiazol-2-amine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CCCNC=3SC4=CC=CC=C4N=3)CC2)=C1 ODJJJYLWJQCPDH-UHFFFAOYSA-N 0.000 description 1
- LUABFORHKKFGEL-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenyl)piperazin-1-yl]butyl]-6-methyl-1,3-benzothiazol-2-amine Chemical compound S1C2=CC(C)=CC=C2N=C1NCCCCN(CC1)CCN1C1=CC=C(Cl)C(Cl)=C1 LUABFORHKKFGEL-UHFFFAOYSA-N 0.000 description 1
- HVQAGCYLLHLDAE-UHFFFAOYSA-N n-[4-[4-(4-methoxyphenyl)piperazin-1-yl]butyl]-1,3-benzothiazol-2-amine Chemical compound C1=CC(OC)=CC=C1N1CCN(CCCCNC=2SC3=CC=CC=C3N=2)CC1 HVQAGCYLLHLDAE-UHFFFAOYSA-N 0.000 description 1
- AZCNTPSPOFJQJA-UHFFFAOYSA-N n-[5-[4-(3,4-dichlorophenyl)piperazin-1-yl]pentyl]-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1CCN(CCCCCNC=2SC3=CC=CC=C3N=2)CC1 AZCNTPSPOFJQJA-UHFFFAOYSA-N 0.000 description 1
- OTISWVDIFYXZDC-WLHGVMLRSA-N n-benzyl-n-[5-[4-(3,4-dichlorophenyl)piperazin-1-yl]pentyl]-1,3-benzothiazol-2-amine;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1=C(Cl)C(Cl)=CC=C1N1CCN(CCCCCN(CC=2C=CC=CC=2)C=2SC3=CC=CC=C3N=2)CC1 OTISWVDIFYXZDC-WLHGVMLRSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229940054010 other antipsychotics in atc Drugs 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 208000022821 personality disease Diseases 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 206010036067 polydipsia Diseases 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000000698 schizophrenic effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 208000012201 sexual and gender identity disease Diseases 0.000 description 1
- 230000009329 sexual behaviour Effects 0.000 description 1
- 208000015891 sexual disease Diseases 0.000 description 1
- 238000003567 signal transduction assay Methods 0.000 description 1
- 238000002603 single-photon emission computed tomography Methods 0.000 description 1
- 230000007958 sleep Effects 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 229950001675 spiperone Drugs 0.000 description 1
- 239000004544 spot-on Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96201282 | 1996-05-10 | ||
| PCT/EP1997/002505 WO1997043271A1 (en) | 1996-05-10 | 1997-05-02 | Alkylaminobenzothiazole and -benzoxazole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO985227D0 NO985227D0 (no) | 1998-11-09 |
| NO985227L NO985227L (no) | 1999-01-11 |
| NO311027B1 true NO311027B1 (no) | 2001-10-01 |
Family
ID=8223970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19985227A NO311027B1 (no) | 1996-05-10 | 1998-11-09 | Alkylaminobenzotiazol og -benzoksazolderivater |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US6103725A (id) |
| EP (2) | EP0912533B1 (id) |
| JP (1) | JP3237759B2 (id) |
| KR (1) | KR100330699B1 (id) |
| CN (1) | CN1074766C (id) |
| AR (1) | AR007079A1 (id) |
| AT (2) | ATE277917T1 (id) |
| AU (1) | AU710175B2 (id) |
| BG (1) | BG64097B1 (id) |
| BR (1) | BR9709065A (id) |
| CA (1) | CA2253453C (id) |
| CZ (1) | CZ295639B6 (id) |
| DE (2) | DE69737217T2 (id) |
| EA (1) | EA001360B1 (id) |
| EE (1) | EE03563B1 (id) |
| ES (2) | ES2230605T3 (id) |
| HK (2) | HK1057044A1 (id) |
| HU (1) | HUP9902993A3 (id) |
| ID (1) | ID16889A (id) |
| IL (1) | IL126968A0 (id) |
| MY (1) | MY117852A (id) |
| NO (1) | NO311027B1 (id) |
| NZ (1) | NZ332309A (id) |
| PL (1) | PL190721B1 (id) |
| SK (1) | SK282919B6 (id) |
| TR (1) | TR199802253T2 (id) |
| TW (1) | TW593290B (id) |
| WO (1) | WO1997043271A1 (id) |
| ZA (1) | ZA974053B (id) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1293804B1 (it) | 1997-08-01 | 1999-03-10 | Recordati Chem Pharm | Diarilalchilpiperazine attive sulle basse vie urinarie |
| US6281216B1 (en) * | 1998-02-09 | 2001-08-28 | Duphar International Research B.V. | 2-aminoquinoline derivatives having d4-agonistic activity |
| EP0982030A3 (en) | 1998-08-17 | 2000-05-10 | Pfizer Products Inc. | 2,7-substituted octahydro-pyrrolo 1,2-a]pyrazine derivatives as 5ht 1a ligands |
| EP1117663A2 (en) * | 1998-09-30 | 2001-07-25 | Neurogen Corporation | 2-piperazino alkylamino benzoazole derivatives: dopamine receptor subtype specific ligands |
| US6284759B1 (en) * | 1998-09-30 | 2001-09-04 | Neurogen Corporation | 2-piperazinoalkylaminobenzo-azole derivatives: dopamine receptor subtype specific ligands |
| US6107313A (en) * | 1998-10-02 | 2000-08-22 | Combichem, Inc. | Dopamine receptor antagonists |
| AU5569800A (en) * | 1999-06-30 | 2001-01-31 | Santen Pharmaceutical Co. Ltd. | Brain sigma-1 receptor-binding ligand |
| AU2001249679A1 (en) | 2000-03-31 | 2001-10-15 | Ortho-Mcneil Pharmaceutical, Inc. | Phenyl-substituted imidazopyridines |
| US6436939B2 (en) | 2000-03-31 | 2002-08-20 | Ortho-Mcneil Pharmaceutical, Inc. | Method for using 2-aryloxyalkylaminobenzoxazoles and 2-aryloxyalkylaminobenzothiazoles as H3 antagonists |
| GB0203299D0 (en) * | 2002-02-12 | 2002-03-27 | Glaxo Group Ltd | Novel compounds |
| CA2497827A1 (en) * | 2002-09-06 | 2004-03-18 | Janssen Pharmaceutica, N.V. | (1h-benzoimidazol-2-yl)-(piperazinyl)-methanone derivatives and related compounds as histamine h4-receptor antagonists for the treatment of inflammatory and allergic disorders |
| EP2610234A1 (en) * | 2004-02-24 | 2013-07-03 | The General Hospital Corporation | Catalytic radiofluorination |
| US8257680B1 (en) | 2004-02-24 | 2012-09-04 | The General Hospital Corporation | Catalytic radiofluorination |
| US9017724B2 (en) | 2004-02-24 | 2015-04-28 | The General Hospital Corporation | Catalytic radiofluorination |
| FR2877005A1 (fr) * | 2004-10-22 | 2006-04-28 | Bioprojet Soc Civ Ile | Nouveaux derives d'arylpiperazine |
| US7731940B2 (en) | 2006-01-25 | 2010-06-08 | The Regents Of The University Of California | Compositions and methods related to serotonin 5-HT1A receptors |
| EP2268647B1 (en) | 2008-03-21 | 2017-01-25 | The General Hospital Corporation | Compounds and compositions for the detection and treatment of alzheimer's disease and related disorders |
| CN109843293A (zh) * | 2016-08-26 | 2019-06-04 | 百时美施贵宝公司 | 吲哚胺2,3-双加氧酶的抑制剂及其使用方法 |
| PT109740B (pt) | 2016-11-14 | 2020-07-30 | Hovione Farmaciencia Sa | Processo para a preparação de brometo de umeclidínio |
| KR20210091865A (ko) * | 2020-01-14 | 2021-07-23 | 서울대학교산학협력단 | 혈관생성 저해 효과를 가지는 n-페닐벤조티아졸-2-아민 화합물 및 그를 포함하는 약제학적 조성물 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0187162B1 (en) * | 1984-05-22 | 1989-11-02 | Sumitomo Chemical Company, Limited | Novel radioactive iodospiroperidol and process for its preparation |
| EP0287909B1 (en) * | 1987-04-08 | 1992-09-02 | Salutar, Inc. | Amyloidosis and alzheimer's disease diagnostic assay and reagents therefor |
| US4929618A (en) * | 1988-03-25 | 1990-05-29 | Ube Industries, Ltd. | Piperdine and piperazine derivatives, and antihistaminic pharmaceutical compositions containing the same |
| FR2656609B1 (fr) * | 1989-12-28 | 1992-03-27 | Synthelabo | Derives de 2-aminopyrimidine-4-carboxamide, leur preparation et leur application en therapeutique. |
| US5731438A (en) * | 1996-08-01 | 1998-03-24 | Isis Pharmaceuticals, Inc. | N-(aminoalkyl)-and/or N-(amidoalkyl)-dinitrogen heterocycles |
-
1997
- 1997-05-01 TW TW086105767A patent/TW593290B/zh not_active IP Right Cessation
- 1997-05-02 DE DE69737217T patent/DE69737217T2/de not_active Expired - Lifetime
- 1997-05-02 KR KR1019980707914A patent/KR100330699B1/ko not_active IP Right Cessation
- 1997-05-02 PL PL97329849A patent/PL190721B1/pl not_active IP Right Cessation
- 1997-05-02 CA CA002253453A patent/CA2253453C/en not_active Expired - Fee Related
- 1997-05-02 DE DE69730962T patent/DE69730962T2/de not_active Expired - Lifetime
- 1997-05-02 BR BR9709065A patent/BR9709065A/pt not_active IP Right Cessation
- 1997-05-02 TR TR1998/02253T patent/TR199802253T2/xx unknown
- 1997-05-02 WO PCT/EP1997/002505 patent/WO1997043271A1/en active IP Right Grant
- 1997-05-02 ES ES97923913T patent/ES2230605T3/es not_active Expired - Lifetime
- 1997-05-02 ES ES03075959T patent/ES2279923T3/es not_active Expired - Lifetime
- 1997-05-02 AU AU29560/97A patent/AU710175B2/en not_active Ceased
- 1997-05-02 EP EP97923913A patent/EP0912533B1/en not_active Expired - Lifetime
- 1997-05-02 US US09/180,369 patent/US6103725A/en not_active Expired - Lifetime
- 1997-05-02 EA EA199801000A patent/EA001360B1/ru not_active IP Right Cessation
- 1997-05-02 CZ CZ19983553A patent/CZ295639B6/cs not_active IP Right Cessation
- 1997-05-02 AT AT97923913T patent/ATE277917T1/de not_active IP Right Cessation
- 1997-05-02 AT AT03075959T patent/ATE350373T1/de not_active IP Right Cessation
- 1997-05-02 HU HU9902993A patent/HUP9902993A3/hu unknown
- 1997-05-02 IL IL12696897A patent/IL126968A0/xx not_active IP Right Cessation
- 1997-05-02 NZ NZ332309A patent/NZ332309A/xx unknown
- 1997-05-02 SK SK1532-98A patent/SK282919B6/sk not_active IP Right Cessation
- 1997-05-02 EE EE9800378A patent/EE03563B1/xx not_active IP Right Cessation
- 1997-05-02 JP JP54053597A patent/JP3237759B2/ja not_active Expired - Lifetime
- 1997-05-02 CN CN97194515A patent/CN1074766C/zh not_active Expired - Lifetime
- 1997-05-02 EP EP03075959A patent/EP1325917B1/en not_active Expired - Lifetime
- 1997-05-07 MY MYPI97002022A patent/MY117852A/en unknown
- 1997-05-09 AR ARP970101955A patent/AR007079A1/es active IP Right Grant
- 1997-05-09 ZA ZA974053A patent/ZA974053B/xx unknown
- 1997-05-09 ID IDP971546A patent/ID16889A/id unknown
-
1998
- 1998-10-07 BG BG102819A patent/BG64097B1/bg unknown
- 1998-11-09 NO NO19985227A patent/NO311027B1/no unknown
-
1999
- 1999-08-16 HK HK03109371A patent/HK1057044A1/xx not_active IP Right Cessation
- 1999-08-16 HK HK99103545A patent/HK1018457A1/xx not_active IP Right Cessation
-
2000
- 2000-06-27 US US09/604,427 patent/US6224849B1/en not_active Expired - Lifetime
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