AR003472A1 - Un procedimiento para preparar un alcohol terciario, un compuesto derivado de alfa-halo-alquil pirimidina y un compuesto intermediario para preparar 6-(1-bromoetil)-4-cloro-5-fluoropirimidina - Google Patents
Un procedimiento para preparar un alcohol terciario, un compuesto derivado de alfa-halo-alquil pirimidina y un compuesto intermediario para preparar 6-(1-bromoetil)-4-cloro-5-fluoropirimidinaInfo
- Publication number
- AR003472A1 AR003472A1 ARP960103831A AR10383196A AR003472A1 AR 003472 A1 AR003472 A1 AR 003472A1 AR P960103831 A ARP960103831 A AR P960103831A AR 10383196 A AR10383196 A AR 10383196A AR 003472 A1 AR003472 A1 AR 003472A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- formula
- halo
- alkyl
- preparing
- Prior art date
Links
Classifications
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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
- C07D239/24—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
- C07D239/30—Halogen atoms or nitro radicals
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- 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
- C07D239/34—One oxygen atom
-
- 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
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
La presente invención se refiere a un procedimiento para preparar un alcohol terciario de la fórmula (I) o una de sus sales de adición de ácidos ode bases, en la que R es fenilo opcionalmente sustituido por 1 a 3 sustituyentes,se lecionados cada uno independientemente entre halo ytrifluorometilo; R1 es alquilo de C1-C6; y Het es pirimidinilo opcionalmente sustituido por 1 a 3 sustituyentes, seleccionados cada unoindependientemente entre alquilo de C1-C4,alcoxi d e C1-C4, alcosi de C1-C4, halo, oxo, bencilo y benciloxi que comprende la reacción de un compuesto de lafórmula (II), en la que R es como se ha definido anteriormente para un compuesto de fórmula (I), con un compuesto de fórmula(III), en la que R1 yHet son como se han definido anteriormente para un compuesto de fórmula (I) y X es cloro, bromo o yodo, en presencia de cinc, yodo y/o un ácido de Lewis yun disolvente orgánico aprótico; estando seguido dicho procedimiento opcionalmente por la conversión del compuesto de fórmula (I) en una sal deadición de ácidos o de bases del mismo. Además, se refiere al alcohol terciario preparado con dicho procedimiento, a un compuesto derivado de alfa-halo-alquil-pirimidina y a uncom puesto intermediario para preparar 6-(1-bromoetil)-4-cloro -5-fluoropirimidina.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9516121.2A GB9516121D0 (en) | 1995-08-05 | 1995-08-05 | Organometallic addition to ketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR003472A1 true AR003472A1 (es) | 1998-08-05 |
Family
ID=10778850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP960103831A AR003472A1 (es) | 1995-08-05 | 1996-08-01 | Un procedimiento para preparar un alcohol terciario, un compuesto derivado de alfa-halo-alquil pirimidina y un compuesto intermediario para preparar 6-(1-bromoetil)-4-cloro-5-fluoropirimidina |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US6586594B1 (es) |
| EP (1) | EP0871625B1 (es) |
| JP (3) | JP3211965B2 (es) |
| KR (1) | KR100269048B1 (es) |
| CN (1) | CN1076019C (es) |
| AR (1) | AR003472A1 (es) |
| AT (1) | ATE256679T1 (es) |
| AU (1) | AU703337B2 (es) |
| BR (1) | BR9609960A (es) |
| CA (1) | CA2228655C (es) |
| CZ (1) | CZ296975B6 (es) |
| DE (1) | DE69631160T2 (es) |
| DK (1) | DK0871625T3 (es) |
| EG (1) | EG21200A (es) |
| ES (1) | ES2210382T3 (es) |
| GB (1) | GB9516121D0 (es) |
| HU (1) | HU224339B1 (es) |
| IL (2) | IL131521A (es) |
| IN (1) | IN190817B (es) |
| MX (1) | MX9801025A (es) |
| MY (1) | MY123062A (es) |
| NO (1) | NO314938B1 (es) |
| NZ (1) | NZ315651A (es) |
| PE (1) | PE16897A1 (es) |
| PL (1) | PL187227B1 (es) |
| PT (1) | PT871625E (es) |
| RU (1) | RU2156760C2 (es) |
| TR (1) | TR199800170T1 (es) |
| TW (1) | TW442480B (es) |
| WO (1) | WO1997006160A1 (es) |
| ZA (1) | ZA966587B (es) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7193083B2 (en) * | 1996-07-26 | 2007-03-20 | Pfizer, Inc. | Preparation of triazoles by organometallic addition to ketones and intermediates therefor |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| RS51752B (sr) | 2002-07-29 | 2011-12-31 | Rigel Pharmaceuticals | Metode tretiranja i prevencije autoimunih oboljenja jedinjenjima 2,4-pirimidindiamina |
| RS53109B (sr) * | 2003-07-30 | 2014-06-30 | Rigel Pharmaceuticals Inc. | Jedinjenja 2,4 pirimidindiamina za upotrebu u tretmanu ili prevenciji autoimunih bolesti |
| US20060058525A1 (en) * | 2004-09-01 | 2006-03-16 | Rajinder Singh | Synthesis of 2,4-pyrimidinediamine compounds |
| CA2584295C (en) * | 2004-11-24 | 2014-08-26 | Rigel Pharmaceuticals, Inc. | Spiro-2, 4-pyrimidinediamine compounds and their uses |
| EP1828170A4 (en) * | 2004-12-14 | 2009-11-11 | Reddys Lab Ltd Dr | PROCESS FOR PREPARING VORICONAZOLE |
| CA2604551A1 (en) * | 2005-05-03 | 2007-03-08 | Rigel Pharmaceuticals, Inc. | Jak kinase inhibitors and their uses |
| CA2640922A1 (en) * | 2006-02-01 | 2007-11-22 | Medichem, S.A. | Process for preparing voriconazole, new polymorphic form of intermediate thereof, and uses thereof |
| AR061889A1 (es) | 2006-07-13 | 2008-10-01 | Medichem Sa | Proceso mejorado para la preparacion de voriconazol |
| CN1919846B (zh) * | 2006-09-14 | 2013-01-02 | 大道隆达（北京）医药科技发展有限公司 | 伏立康唑及其药用盐、中间体的一种新定向合成制备方法 |
| KR100889937B1 (ko) * | 2007-08-06 | 2009-03-20 | 한미약품 주식회사 | 보리코나졸의 제조방법 |
| GB2452049A (en) * | 2007-08-21 | 2009-02-25 | Alpharma Aps | Process for the preparation of voriconazole |
| WO2009084029A2 (en) * | 2007-12-03 | 2009-07-09 | Neuland Laboratories Ltd | Improved process for the preparation of (2r,3s)-2-(2,4- difluqrophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1h-1,2,4-triazol-1-yl) butan-2-ol |
| CN101575330B (zh) * | 2008-05-05 | 2012-10-31 | 丽珠医药集团股份有限公司 | 伏立康唑广谱抗真菌药物化合物、其组合物及用途 |
| RU2399621C2 (ru) * | 2008-10-14 | 2010-09-20 | Андрей Александрович Иващенко | ЗАМЕЩЕННЫЕ 2-АЛКИЛАМИНО-3-СУЛЬФОНИЛ-ПИРАЗОЛО[1,5-a]ПИРИМИДИНЫ, АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
| RU2393157C1 (ru) * | 2008-10-06 | 2010-06-27 | Андрей Александрович Иващенко | 2-АЛКИЛАМИНО-3-АРИЛСУЛЬФОНИЛ-ПИРАЗОЛО[1,5-а]ПИРИМИДИНЫ, АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
| RU2393158C1 (ru) * | 2008-10-06 | 2010-06-27 | Андрей Александрович Иващенко | ЗАМЕЩЕННЫЕ 3-АРИЛСУЛЬФОНИЛ-ПИРАЗОЛО[1,5-а]ПИРИМИДИНЫ, АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
| US20110312977A1 (en) * | 2009-02-17 | 2011-12-22 | Glenmark Generics Limited | Process for the preparation of voriconazole |
| KR101109215B1 (ko) | 2009-06-17 | 2012-01-30 | 보령제약 주식회사 | 보리코나졸의 신규 중간체 및 이를 이용한 보리코나졸의 제조방법 |
| ES2529562T3 (es) * | 2009-12-30 | 2015-02-23 | Medichem, S.A. | Un derivado de 1-(1H-1,2,4-triazol-1-il)butan-2-ol para uso farmacéutico, y el uso de un derivado de 1-(1H-1,2,4-triazol-1-il)butan-2-ol con forma cristalina sustancialmente indefinida para preparar dicho derivado de 1-(1H-1,2,4-triazol-1-il)butan-2-ol |
| KR100971371B1 (ko) | 2010-02-04 | 2010-07-20 | 동국제약 주식회사 | 신규한 중간체를 이용한 보리코나졸의 제조방법 |
| RU2421456C1 (ru) * | 2010-02-26 | 2011-06-20 | Общество С Ограниченной Ответственностью "Инновационная Фармацевтика" | ЗАМЕЩЕННЫЕ 3-АРИЛСУЛЬФОНИЛ-ПИРАЗОЛО[1,5-a]ПИРИМИДИН-2,6-ДИАМИНЫ, АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-НТ6 РЕЦЕПТОРОВ, СПОСОБЫ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
| EP2545039A1 (en) | 2010-03-10 | 2013-01-16 | Synthon BV | A process for making voriconazole |
| CN101914091B (zh) * | 2010-07-25 | 2015-05-27 | 浙江华海药业股份有限公司 | 一种制备伏立康唑中间体的方法 |
| CN102344441B (zh) * | 2010-07-25 | 2015-05-06 | 浙江华海药业股份有限公司 | 一种制备伏立康唑中间体的工艺改进方法 |
| CA2827379A1 (en) * | 2011-02-21 | 2012-08-30 | Ranbaxy Laboratories Limited | An improved process for the preparation of voriconazole and intermediates thereof |
| PL2720723T3 (pl) | 2011-06-15 | 2018-10-31 | Synthon Bv | Stabilizowana kompozycja worykonazolu |
| CN102516233B (zh) * | 2011-12-09 | 2014-04-09 | 北京联本医药化学技术有限公司 | 生产伏立康唑的方法 |
| GR1007802B (el) * | 2012-01-31 | 2013-01-18 | Φαρματεν Αβεε, | Μεθοδος για την παρασκευη παραγωγου της βρωμοπυρινιδινης |
| ES2615743T3 (es) * | 2012-10-15 | 2017-06-08 | Pfizer Ireland Pharmaceuticals | Procedimiento de preparación de voriconazol y análogos de los mismos |
| KR101435741B1 (ko) | 2013-01-17 | 2014-08-29 | (주) 에프엔지리서치 | 신규한 보리코나졸 중간체 및 이를 이용한 보리코나졸의 제조 방법 |
| CN105503834B (zh) * | 2015-12-23 | 2021-03-05 | 浙江华海药业股份有限公司 | 一种伏立康唑中间体的合成方法 |
| CN106432198B (zh) | 2016-09-08 | 2022-10-21 | 浙江华海药业股份有限公司 | 一种制备伏立康唑拆分中间体的方法 |
| CN106632267B (zh) * | 2016-11-09 | 2019-02-22 | 中国科学院成都生物研究所 | 一种伏立康唑的合成方法 |
| US11312707B2 (en) * | 2016-11-28 | 2022-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of fungal infections |
| CN108276310A (zh) * | 2017-01-06 | 2018-07-13 | 常州齐晖药业有限公司 | 一种伏立康唑拆分剂(r)-10-樟脑磺酸的回收方法 |
| CN108586433A (zh) * | 2017-07-21 | 2018-09-28 | 齐鲁工业大学 | 具有抗菌活性的伏立康唑盐酸盐 |
| CN109705102A (zh) * | 2019-02-19 | 2019-05-03 | 浙江华海立诚药业有限公司 | 伏立康唑及其中间体的制备方法 |
| CN110305113A (zh) * | 2019-07-05 | 2019-10-08 | 镇江市第四人民医院（镇江市妇幼保健院） | 一种伏立康唑杂质b的合成方法 |
| CN112442017A (zh) * | 2019-08-29 | 2021-03-05 | 珠海润都制药股份有限公司 | 一种采用微通道反应器制备伏立康唑消旋体的方法 |
| CN110724130A (zh) * | 2019-11-29 | 2020-01-24 | 怀化学院 | 伏立康唑及其中间体的合成方法 |
| CN111440152B (zh) * | 2020-05-18 | 2022-09-27 | 浙江诚意药业股份有限公司 | 一种伏立康唑的制备方法 |
| CN112079819B (zh) * | 2020-09-24 | 2022-06-17 | 南京易亨制药有限公司 | 一种改进的伏立康唑消旋体制备方法 |
| CN112645935A (zh) * | 2020-12-15 | 2021-04-13 | 植恩生物技术股份有限公司 | 伏立康唑关键中间体的制备方法 |
| CN117069693A (zh) * | 2022-05-16 | 2023-11-17 | 上海济煜医药科技有限公司 | 一类含胺基结构化合物的制备方法及作为抗菌剂的应用 |
| CN115724829A (zh) * | 2022-12-23 | 2023-03-03 | 天津力生制药股份有限公司 | 一种分离真菌药物中间体杂质的液相色谱制备方法 |
| CN116730985A (zh) * | 2023-06-20 | 2023-09-12 | 天津力生制药股份有限公司 | 一锅法制备伏立康唑的合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8305377D0 (en) * | 1983-02-25 | 1983-03-30 | Pfizer Ltd | Antifungal agents |
| GB8307232D0 (en) * | 1983-03-16 | 1983-04-20 | Pfizer Ltd | Antifungal agents |
| GB8819308D0 (en) * | 1988-08-13 | 1988-09-14 | Pfizer Ltd | Triazole antifungal agents |
| GB9002375D0 (en) * | 1990-02-02 | 1990-04-04 | Pfizer Ltd | Triazole antifungal agents |
| EP0665225B1 (en) * | 1994-02-01 | 1996-11-27 | Ube Industries, Ltd. | 4-Phenethylamino pyrimidine derivative, process for preparing the same and agricultural and horticultural chemical for controlling noxious organisms containing the same |
-
1995
- 1995-08-05 GB GBGB9516121.2A patent/GB9516121D0/en active Pending
-
1996
- 1996-07-13 TW TW085108523A patent/TW442480B/zh not_active IP Right Cessation
- 1996-07-26 DK DK96927644T patent/DK0871625T3/da active
- 1996-07-26 NZ NZ315651A patent/NZ315651A/xx unknown
- 1996-07-26 KR KR1019980700842A patent/KR100269048B1/ko not_active Expired - Fee Related
- 1996-07-26 JP JP50809797A patent/JP3211965B2/ja not_active Expired - Lifetime
- 1996-07-26 US US09/011,346 patent/US6586594B1/en not_active Expired - Fee Related
- 1996-07-26 IL IL13152196A patent/IL131521A/en not_active IP Right Cessation
- 1996-07-26 TR TR1998/00170T patent/TR199800170T1/xx unknown
- 1996-07-26 DE DE69631160T patent/DE69631160T2/de not_active Expired - Fee Related
- 1996-07-26 PL PL96324922A patent/PL187227B1/pl not_active IP Right Cessation
- 1996-07-26 AT AT96927644T patent/ATE256679T1/de not_active IP Right Cessation
- 1996-07-26 CZ CZ0032798A patent/CZ296975B6/cs not_active IP Right Cessation
- 1996-07-26 HU HU9802766A patent/HU224339B1/hu not_active IP Right Cessation
- 1996-07-26 MX MX9801025A patent/MX9801025A/es not_active IP Right Cessation
- 1996-07-26 PT PT96927644T patent/PT871625E/pt unknown
- 1996-07-26 IL IL12246296A patent/IL122462A/en not_active IP Right Cessation
- 1996-07-26 CA CA002228655A patent/CA2228655C/en not_active Expired - Fee Related
- 1996-07-26 RU RU98103373/04A patent/RU2156760C2/ru not_active IP Right Cessation
- 1996-07-26 CN CN96196097A patent/CN1076019C/zh not_active Expired - Fee Related
- 1996-07-26 AU AU67403/96A patent/AU703337B2/en not_active Ceased
- 1996-07-26 WO PCT/EP1996/003376 patent/WO1997006160A1/en not_active Ceased
- 1996-07-26 BR BR9609960A patent/BR9609960A/pt not_active IP Right Cessation
- 1996-07-26 EP EP96927644A patent/EP0871625B1/en not_active Expired - Lifetime
- 1996-07-26 ES ES96927644T patent/ES2210382T3/es not_active Expired - Lifetime
- 1996-07-31 IN IN1707DE1996 patent/IN190817B/en unknown
- 1996-08-01 PE PE1996000578A patent/PE16897A1/es not_active Application Discontinuation
- 1996-08-01 AR ARP960103831A patent/AR003472A1/es active IP Right Grant
- 1996-08-02 ZA ZA9606587A patent/ZA966587B/xx unknown
- 1996-08-03 MY MYPI96003196A patent/MY123062A/en unknown
- 1996-08-04 EG EG73196A patent/EG21200A/xx active
-
1998
- 1998-02-02 NO NO19980441A patent/NO314938B1/no not_active IP Right Cessation
-
2000
- 2000-06-21 JP JP2000186089A patent/JP3224532B2/ja not_active Expired - Fee Related
-
2001
- 2001-04-27 JP JP2001131297A patent/JP2001354670A/ja active Pending
-
2003
- 2003-02-19 US US10/368,928 patent/US6946555B2/en not_active Expired - Fee Related
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