NO310512B1 - 5H-Tiazolo [3,2-a] pyrimidinderivater - Google Patents
5H-Tiazolo [3,2-a] pyrimidinderivater Download PDFInfo
- Publication number
- NO310512B1 NO310512B1 NO19983244A NO983244A NO310512B1 NO 310512 B1 NO310512 B1 NO 310512B1 NO 19983244 A NO19983244 A NO 19983244A NO 983244 A NO983244 A NO 983244A NO 310512 B1 NO310512 B1 NO 310512B1
- Authority
- NO
- Norway
- Prior art keywords
- dichlorophenyl
- thiazolo
- dimethylaminoethyl
- denotes
- methyl
- Prior art date
Links
- CDUYCVWBLGEWSY-UHFFFAOYSA-N 5h-[1,3]thiazolo[3,2-a]pyrimidine Chemical class C1C=CN=C2SC=CN12 CDUYCVWBLGEWSY-UHFFFAOYSA-N 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- -1 nine faiths Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- NMPVEAUIHMEAQP-UHFFFAOYSA-N 2-Bromoacetaldehyde Chemical compound BrCC=O NMPVEAUIHMEAQP-UHFFFAOYSA-N 0.000 claims description 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 6
- 208000012902 Nervous system disease Diseases 0.000 claims description 6
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- 206010034010 Parkinsonism Diseases 0.000 claims description 6
- 230000001684 chronic effect Effects 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
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- GBPBWQGPBSYBOV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-(2,6-dichlorophenyl)-5-(2-methoxyphenyl)-7-methyl-5h-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate Chemical compound COC1=CC=CC=C1C1C(C(=O)OCCN(C)C)=C(C)N=C2SC(C=3C(=CC=CC=3Cl)Cl)=CN21 GBPBWQGPBSYBOV-UHFFFAOYSA-N 0.000 claims 1
- VNUCNKCATYSOBV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-(2,6-dichlorophenyl)-7-ethyl-5-(2-methoxyphenyl)-5h-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate Chemical compound S1C2=NC(CC)=C(C(=O)OCCN(C)C)C(C=3C(=CC=CC=3)OC)N2C=C1C1=C(Cl)C=CC=C1Cl VNUCNKCATYSOBV-UHFFFAOYSA-N 0.000 claims 1
- KTYIETCDDNNOLD-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-(2,6-dichlorophenyl)-7-methyl-5-(2-propan-2-yloxyphenyl)-5h-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate Chemical compound CC(C)OC1=CC=CC=C1C1C(C(=O)OCCN(C)C)=C(C)N=C2SC(C=3C(=CC=CC=3Cl)Cl)=CN21 KTYIETCDDNNOLD-UHFFFAOYSA-N 0.000 claims 1
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- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims 1
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- LWFQGLZKTGSAQC-UHFFFAOYSA-N 2-(dimethylamino)ethyl 3-oxobutanoate Chemical compound CN(C)CCOC(=O)CC(C)=O LWFQGLZKTGSAQC-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- 108010010914 Metabotropic glutamate receptors Proteins 0.000 description 7
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- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Public Health (AREA)
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- Psychiatry (AREA)
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- Rheumatology (AREA)
- Anesthesiology (AREA)
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- Endocrinology (AREA)
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- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97112324 | 1997-07-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO983244D0 NO983244D0 (no) | 1998-07-14 |
| NO983244L NO983244L (no) | 1999-01-19 |
| NO310512B1 true NO310512B1 (no) | 2001-07-16 |
Family
ID=8227080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19983244A NO310512B1 (no) | 1997-07-18 | 1998-07-14 | 5H-Tiazolo [3,2-a] pyrimidinderivater |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US5958931A (fr) |
| EP (1) | EP0891978B1 (fr) |
| JP (1) | JP3100573B2 (fr) |
| KR (1) | KR100296837B1 (fr) |
| CN (1) | CN1102596C (fr) |
| AR (1) | AR016129A1 (fr) |
| AT (1) | ATE214704T1 (fr) |
| AU (1) | AU738207B2 (fr) |
| BR (1) | BR9802482A (fr) |
| CA (1) | CA2243234C (fr) |
| CO (1) | CO5210884A1 (fr) |
| CZ (1) | CZ288944B6 (fr) |
| DE (1) | DE69804273T2 (fr) |
| DK (1) | DK0891978T3 (fr) |
| ES (1) | ES2172840T3 (fr) |
| HK (1) | HK1018439A1 (fr) |
| HR (1) | HRP980398B1 (fr) |
| HU (1) | HUP9801587A3 (fr) |
| ID (1) | ID21824A (fr) |
| IL (1) | IL125358A (fr) |
| MA (1) | MA26520A1 (fr) |
| NO (1) | NO310512B1 (fr) |
| NZ (1) | NZ330988A (fr) |
| PE (1) | PE97499A1 (fr) |
| PL (1) | PL190218B1 (fr) |
| PT (1) | PT891978E (fr) |
| RU (1) | RU2197493C2 (fr) |
| SI (1) | SI0891978T1 (fr) |
| TR (1) | TR199801367A2 (fr) |
| TW (1) | TW523518B (fr) |
| UY (1) | UY25095A1 (fr) |
| YU (1) | YU29798A (fr) |
| ZA (1) | ZA986250B (fr) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1074549B1 (fr) * | 1999-08-06 | 2003-11-19 | F. Hoffmann-La Roche Ag | Tétrahydro-benzo(d)azépines et leurs utilisations en tant qu'antagonistes du récepteur de glutamate métabotropique |
| HUP0401858A3 (en) * | 2001-01-31 | 2009-06-29 | Lundbeck & Co As H | Gal3 receptor antagonist pyrimidine and indolone-derivatives and their use for preparation of pharmaceutical compositions suitable for the treatment of depression and/or anxiety |
| JPWO2002102807A1 (ja) * | 2001-06-14 | 2004-09-30 | 萬有製薬株式会社 | 新規イソキサゾロピリドン誘導体及びその用途 |
| US7329662B2 (en) * | 2003-10-03 | 2008-02-12 | Hoffmann-La Roche Inc. | Pyrazolo-pyridine |
| JP4608542B2 (ja) * | 2004-06-21 | 2011-01-12 | エフ．ホフマン−ラ ロシュ アーゲー | ピラゾロピリミジン誘導体 |
| KR100847160B1 (ko) * | 2004-06-21 | 2008-07-17 | 에프. 호프만-라 로슈 아게 | 피라졸로 피리미딘 유도체 |
| EP1851225B1 (fr) | 2005-02-11 | 2011-06-15 | F. Hoffmann-La Roche AG | Derives de pyrazolopyrimidine en tant qu'antagonistes de mglur2 |
| BRPI0609719B8 (pt) | 2005-03-23 | 2021-05-25 | Hoffmann La Roche | derivados de acetilenil-pirazol-pirimidina como antagonistas de mgbur2 |
| BRPI0616571A2 (pt) | 2005-09-27 | 2011-06-21 | Hoffmann La Roche | oxadiazolil pirazol-piridiminas como antagonistas de mglur2, processo para sua preparação, composição farmacêutica que os contém e uso dos mesmo |
| TWI417095B (zh) | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | １，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途 |
| TW200845978A (en) * | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| CN101801951B (zh) | 2007-09-14 | 2013-11-13 | 杨森制药有限公司 | 1’,3’-二取代的-4-苯基-3,4,5,6-四氢-2h,1’h-[1,4’]二吡啶-2’-酮 |
| AU2008297877C1 (en) * | 2007-09-14 | 2013-11-07 | Addex Pharma S.A. | 1,3-disubstituted-4-phenyl-1 H-pyridin-2-ones |
| EP2200985B1 (fr) | 2007-09-14 | 2011-07-13 | Ortho-McNeil-Janssen Pharmaceuticals, Inc. | 4-(aryl-x-phényl)-1h-pyridine-2-ones 1,3-disubstituées |
| CN101861316B (zh) * | 2007-11-14 | 2013-08-21 | 奥梅-杨森制药有限公司 | 咪唑并[1,2-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| ES2439291T3 (es) | 2008-09-02 | 2014-01-22 | Janssen Pharmaceuticals, Inc. | Derivados de 3-azabiciclo[3.1.0]hexilo como moduladores de receptores de glutamato metabotrópicos |
| JP5656848B2 (ja) | 2008-10-16 | 2015-01-21 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | 代謝型グルタミン酸受容体モジュレーターとしてのインドールおよびベンゾモルホリンの誘導体 |
| US8691813B2 (en) | 2008-11-28 | 2014-04-08 | Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| CN101503414B (zh) * | 2009-03-04 | 2013-10-30 | 沈阳药科大学 | 噻唑并[3,2-b]-1,2,4-三嗪衍生物及其应用 |
| MX2011011962A (es) | 2009-05-12 | 2012-02-28 | Janssen Pharmaceuticals Inc | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostericos positivos de receptores de glutamato metabotropico (mglur2). |
| ME01573B (me) | 2009-05-12 | 2014-09-20 | Addex Pharma Sa | DERIVATI 1,2,4-TRIAZOLO[4,3-a]PIRIDINA I NJIHOVA UPOTREBA U TRETMANU ILI PREVENCIJI NEUROLOŠKIH I PSIHIJATRIJSKIH POREMEĆAJA |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| US9271967B2 (en) | 2010-11-08 | 2016-03-01 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| AU2011328195B2 (en) | 2010-11-08 | 2015-04-02 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| JP5852666B2 (ja) | 2010-11-08 | 2016-02-03 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | １，２，４−トリアゾロ［４，３−ａ］ピリジン誘導体およびｍＧｌｕＲ２受容体のポジティブアロステリックモジュレーターとしてのそれらの使用 |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| PT3055315T (pt) | 2013-10-11 | 2018-10-25 | Hoffmann La Roche | Tiazolopirimidonas enquanto moduladores da atividade do recetor nmda |
| PL3096790T3 (pl) | 2014-01-21 | 2020-01-31 | Janssen Pharmaceutica, N.V. | Kombinacje zawierające pozytywne modulatory allosteryczne lub agonistów ortosterycznych metabotropowego receptora glutaminergicznego podtypu 2 i ich zastosowanie |
| KR20200036063A (ko) | 2014-01-21 | 2020-04-06 | 얀센 파마슈티카 엔.브이. | 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도 |
| AU2018241628B2 (en) * | 2017-03-31 | 2022-03-17 | Basf Se | Pyrimidinium compounds and their mixtures for combating animal pests |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3660418A (en) * | 1970-03-16 | 1972-05-02 | Sandoz Ag | Certain 2 3 5 6-tetrahydroimidazo(2 1-b)thiazoles |
| EP0524055A1 (fr) * | 1991-07-19 | 1993-01-20 | Synthelabo | Dérivés d'imidazo[2,1-b]benzothiazole-3-acétamide, leur préparation et leur application en thérapeutique |
| PL182285B1 (pl) * | 1994-08-12 | 2001-12-31 | Lilly Co Eli | Syntetyczne aminokwasy oraz ich estry i srodki farmaceutyczne je zawierajace PL PL PL PL PL PL PL |
| GB9609976D0 (en) * | 1996-05-13 | 1996-07-17 | Lilly Industries Ltd | Pharmaceutical compounds |
| AU3783497A (en) * | 1996-08-09 | 1998-03-06 | Yamanouchi Pharmaceutical Co., Ltd. | Metabotropic glutamate receptor agonists |
-
1998
- 1998-07-11 SI SI9830130T patent/SI0891978T1/xx unknown
- 1998-07-11 EP EP98112915A patent/EP0891978B1/fr not_active Expired - Lifetime
- 1998-07-11 DK DK98112915T patent/DK0891978T3/da active
- 1998-07-11 PT PT98112915T patent/PT891978E/pt unknown
- 1998-07-11 ES ES98112915T patent/ES2172840T3/es not_active Expired - Lifetime
- 1998-07-11 AT AT98112915T patent/ATE214704T1/de not_active IP Right Cessation
- 1998-07-11 DE DE69804273T patent/DE69804273T2/de not_active Expired - Fee Related
- 1998-07-14 US US09/115,191 patent/US5958931A/en not_active Expired - Fee Related
- 1998-07-14 ZA ZA986250A patent/ZA986250B/xx unknown
- 1998-07-14 NZ NZ330988A patent/NZ330988A/xx unknown
- 1998-07-14 MA MA25167A patent/MA26520A1/fr unknown
- 1998-07-14 ID IDP981000A patent/ID21824A/id unknown
- 1998-07-14 TR TR1998/01367A patent/TR199801367A2/xx unknown
- 1998-07-14 NO NO19983244A patent/NO310512B1/no not_active IP Right Cessation
- 1998-07-15 YU YU29798A patent/YU29798A/sh unknown
- 1998-07-15 CA CA002243234A patent/CA2243234C/fr not_active Expired - Fee Related
- 1998-07-15 HU HU9801587A patent/HUP9801587A3/hu unknown
- 1998-07-15 IL IL12535898A patent/IL125358A/en not_active IP Right Cessation
- 1998-07-15 CN CN98116063A patent/CN1102596C/zh not_active Expired - Fee Related
- 1998-07-15 PE PE1998000625A patent/PE97499A1/es not_active Application Discontinuation
- 1998-07-15 JP JP10199363A patent/JP3100573B2/ja not_active Expired - Fee Related
- 1998-07-16 BR BR9802482-5A patent/BR9802482A/pt not_active Application Discontinuation
- 1998-07-16 CO CO98040510A patent/CO5210884A1/es not_active Application Discontinuation
- 1998-07-16 PL PL98327532A patent/PL190218B1/pl unknown
- 1998-07-16 AR ARP980103469A patent/AR016129A1/es not_active Application Discontinuation
- 1998-07-16 UY UY25095A patent/UY25095A1/es unknown
- 1998-07-16 KR KR1019980028788A patent/KR100296837B1/ko not_active IP Right Cessation
- 1998-07-16 HR HR980398A patent/HRP980398B1/xx not_active IP Right Cessation
- 1998-07-16 CZ CZ19982239A patent/CZ288944B6/cs not_active IP Right Cessation
- 1998-07-17 AU AU77302/98A patent/AU738207B2/en not_active Ceased
- 1998-07-17 RU RU98114683/04A patent/RU2197493C2/ru not_active IP Right Cessation
- 1998-07-21 TW TW087111834A patent/TW523518B/zh not_active IP Right Cessation
-
1999
- 1999-07-14 HK HK99103032A patent/HK1018439A1/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
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| MM1K | Lapsed by not paying the annual fees |