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
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- 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)
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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 |
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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 |
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NO19983244A NO310512B1 (no) | 1997-07-18 | 1998-07-14 | 5H-Tiazolo [3,2-a] pyrimidinderivater |
Country Status (33)
Country | Link |
---|---|
US (1) | US5958931A (de) |
EP (1) | EP0891978B1 (de) |
JP (1) | JP3100573B2 (de) |
KR (1) | KR100296837B1 (de) |
CN (1) | CN1102596C (de) |
AR (1) | AR016129A1 (de) |
AT (1) | ATE214704T1 (de) |
AU (1) | AU738207B2 (de) |
BR (1) | BR9802482A (de) |
CA (1) | CA2243234C (de) |
CO (1) | CO5210884A1 (de) |
CZ (1) | CZ288944B6 (de) |
DE (1) | DE69804273T2 (de) |
DK (1) | DK0891978T3 (de) |
ES (1) | ES2172840T3 (de) |
HK (1) | HK1018439A1 (de) |
HR (1) | HRP980398B1 (de) |
HU (1) | HUP9801587A3 (de) |
ID (1) | ID21824A (de) |
IL (1) | IL125358A (de) |
MA (1) | MA26520A1 (de) |
NO (1) | NO310512B1 (de) |
NZ (1) | NZ330988A (de) |
PE (1) | PE97499A1 (de) |
PL (1) | PL190218B1 (de) |
PT (1) | PT891978E (de) |
RU (1) | RU2197493C2 (de) |
SI (1) | SI0891978T1 (de) |
TR (1) | TR199801367A3 (de) |
TW (1) | TW523518B (de) |
UY (1) | UY25095A1 (de) |
YU (1) | YU29798A (de) |
ZA (1) | ZA986250B (de) |
Families Citing this family (32)
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EP1074549B1 (de) * | 1999-08-06 | 2003-11-19 | F. Hoffmann-La Roche Ag | Tetrahydro-benzo(d)azepine und deren Verwendung als metabotrope Glutamatrezeptor-Antagonisten |
BR0206844A (pt) * | 2001-01-31 | 2005-07-12 | Synaptic Pharma Corp | Uso de antagonistas do receptor gal3 para o tratamento de depressão e/ou ansiedade e compostos usados em tais métodos |
WO2002102807A1 (fr) * | 2001-06-14 | 2002-12-27 | Banyu Pharmaceutical Co., Ltd. | Nouveaux derives d'isoxazolopyridone et leur utilisation |
US7329662B2 (en) | 2003-10-03 | 2008-02-12 | Hoffmann-La Roche Inc. | Pyrazolo-pyridine |
KR100847160B1 (ko) * | 2004-06-21 | 2008-07-17 | 에프. 호프만-라 로슈 아게 | 피라졸로 피리미딘 유도체 |
CN100528876C (zh) * | 2004-06-21 | 2009-08-19 | 弗·哈夫曼-拉罗切有限公司 | 吡唑并嘧啶衍生物 |
ES2365406T3 (es) | 2005-02-11 | 2011-10-04 | F. Hoffmann-La Roche Ag | Derivados de pirazolo-pirimidina como antagonistas de mglur2. |
EP1863818B1 (de) | 2005-03-23 | 2010-03-10 | F.Hoffmann-La Roche Ag | Acetylenylpyrazolopyrimidinderivate als mglur2-antagonsten |
ES2340321T3 (es) | 2005-09-27 | 2010-06-01 | F.Hoffmann-La Roche Ag | Oxadiazolilpirazolo-pirimidinas, como antagonistas de mglur2. |
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 |
JP5433579B2 (ja) * | 2007-09-14 | 2014-03-05 | 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. | 1,3−二置換−4−フェニル−1h−ピリジン−2−オン |
RS51660B (en) * | 2007-09-14 | 2011-10-31 | Ortho-Mcneil-Janssen Pharmaceuticals Inc. | 1`, 3`-DISUPSTITUATED-4-PHENYL-3,4,5,6-TETRAHYDRO-2H, 1`H- [1,4`] BIPYRIDINYL-2`-ONE |
TW200922566A (en) | 2007-09-14 | 2009-06-01 | Ortho Mcneil Janssen Pharm | 1,3 disubstituted 4-(aryl-X-phenyl)-1H-pyridin-2-ones |
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 |
RU2510396C2 (ru) | 2008-09-02 | 2014-03-27 | Янссен Фармасьютикалз, Инк. | 3-азабицикло[3.1.0]гексильные производные в качестве модуляторов метаботропных глутаматных рецепторов |
US8697689B2 (en) | 2008-10-16 | 2014-04-15 | Janssen Pharmaceuticals, Inc. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
RU2512283C2 (ru) | 2008-11-28 | 2014-04-10 | Янссен Фармасьютикалз, Инк. | Производные индола и бензоксазина в качестве модуляторов метаботропных глутаматных рецепторов |
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 |
MY153912A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 1, 2, 4,-triazolo[4,3-a[pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
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 |
WO2012062759A1 (en) | 2010-11-08 | 2012-05-18 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
CA2814996C (en) | 2010-11-08 | 2019-10-01 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
CN103261195B (zh) | 2010-11-08 | 2015-09-02 | 杨森制药公司 | 1,2,4-***并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
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 |
JP6419800B2 (ja) | 2013-10-11 | 2018-11-07 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | Nmda受容体活性の調節因子としてのチアゾロピリミジノン |
KR102502485B1 (ko) | 2014-01-21 | 2023-02-21 | 얀센 파마슈티카 엔.브이. | 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도 |
UA121965C2 (uk) | 2014-01-21 | 2020-08-25 | Янссен Фармацевтика Нв | Комбінації, які містять позитивні алостеричні модулятори або ортостеричні агоністи метаботропного глутаматергічного рецептора 2 підтипу, та їх застосування |
MX2019011785A (es) * | 2017-03-31 | 2019-11-18 | Basf Se | Proceso para preparar compuestos de 2,3-dihidrotiazolo[3,2-a]pirim idin-4-io quirales. |
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Publication number | Priority date | Publication date | Assignee | Title |
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US3660418A (en) * | 1970-03-16 | 1972-05-02 | Sandoz Ag | Certain 2 3 5 6-tetrahydroimidazo(2 1-b)thiazoles |
EP0524055A1 (de) * | 1991-07-19 | 1993-01-20 | Synthelabo | Imidazo(2,1-b)benzothiazolderivate, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung |
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 |
WO1998006724A1 (fr) * | 1996-08-09 | 1998-02-19 | Yamanouchi Pharmaceutical Co., Ltd. | Agonistes du recepteur du glutamate metabotropique |
-
1998
- 1998-07-11 EP EP98112915A patent/EP0891978B1/de not_active Expired - Lifetime
- 1998-07-11 AT AT98112915T patent/ATE214704T1/de not_active IP Right Cessation
- 1998-07-11 ES ES98112915T patent/ES2172840T3/es not_active Expired - Lifetime
- 1998-07-11 DK DK98112915T patent/DK0891978T3/da active
- 1998-07-11 DE DE69804273T patent/DE69804273T2/de not_active Expired - Fee Related
- 1998-07-11 PT PT98112915T patent/PT891978E/pt unknown
- 1998-07-11 SI SI9830130T patent/SI0891978T1/xx unknown
- 1998-07-14 MA MA25167A patent/MA26520A1/fr unknown
- 1998-07-14 ZA ZA986250A patent/ZA986250B/xx unknown
- 1998-07-14 ID IDP981000A patent/ID21824A/id unknown
- 1998-07-14 NZ NZ330988A patent/NZ330988A/xx unknown
- 1998-07-14 TR TR1998/01367A patent/TR199801367A3/tr unknown
- 1998-07-14 US US09/115,191 patent/US5958931A/en not_active Expired - Fee Related
- 1998-07-14 NO NO19983244A patent/NO310512B1/no not_active IP Right Cessation
- 1998-07-15 PE PE1998000625A patent/PE97499A1/es not_active Application Discontinuation
- 1998-07-15 HU HU9801587A patent/HUP9801587A3/hu unknown
- 1998-07-15 JP JP10199363A patent/JP3100573B2/ja not_active Expired - Fee Related
- 1998-07-15 CN CN98116063A patent/CN1102596C/zh not_active Expired - Fee Related
- 1998-07-15 IL IL12535898A patent/IL125358A/en not_active IP Right Cessation
- 1998-07-15 YU YU29798A patent/YU29798A/sh unknown
- 1998-07-15 CA CA002243234A patent/CA2243234C/en 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 KR KR1019980028788A patent/KR100296837B1/ko not_active IP Right Cessation
- 1998-07-16 AR ARP980103469A patent/AR016129A1/es not_active Application Discontinuation
- 1998-07-16 CZ CZ19982239A patent/CZ288944B6/cs not_active IP Right Cessation
- 1998-07-16 PL PL98327532A patent/PL190218B1/pl unknown
- 1998-07-16 HR HR980398A patent/HRP980398B1/xx not_active IP Right Cessation
- 1998-07-16 UY UY25095A patent/UY25095A1/es unknown
- 1998-07-17 RU RU98114683/04A patent/RU2197493C2/ru not_active IP Right Cessation
- 1998-07-17 AU AU77302/98A patent/AU738207B2/en not_active Ceased
- 1998-07-21 TW TW087111834A patent/TW523518B/zh not_active IP Right Cessation
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1999
- 1999-07-14 HK HK99103032A patent/HK1018439A1/xx not_active IP Right Cessation
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