CA2383751C - Intermediates for the production of quinolone carboxylic acid derivatives - Google Patents
Intermediates for the production of quinolone carboxylic acid derivatives Download PDFInfo
- Publication number
- CA2383751C CA2383751C CA2383751A CA2383751A CA2383751C CA 2383751 C CA2383751 C CA 2383751C CA 2383751 A CA2383751 A CA 2383751A CA 2383751 A CA2383751 A CA 2383751A CA 2383751 C CA2383751 C CA 2383751C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- process according
- carboxylic acid
- aminomethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 239000000543 intermediate Substances 0.000 title abstract description 6
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- -1 t-butyloxycarbonyl Chemical group 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- UEOGQXKQVBYIDZ-UHFFFAOYSA-N methanesulfonate;(4-methoxyiminopyrrolidin-1-ium-3-yl)methanamine Chemical compound CS([O-])(=O)=O.CS([O-])(=O)=O.CON=C1C[NH2+]CC1CN.CON=C1C[NH2+]CC1CN UEOGQXKQVBYIDZ-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 3
- SNLMOXFUCILIPL-UHFFFAOYSA-N 1,8-naphthyridine-2-carboxylic acid Chemical class C1=CC=NC2=NC(C(=O)O)=CC=C21 SNLMOXFUCILIPL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 229940088679 drug related substance Drugs 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- KVERQKOZMUXLTL-UHFFFAOYSA-N methanesulfonic acid trihydrate Chemical compound O.O.O.CS(O)(=O)=O.CS(O)(=O)=O KVERQKOZMUXLTL-UHFFFAOYSA-N 0.000 description 2
- 229940072132 quinolone antibacterials Drugs 0.000 description 2
- ZEEYWNLTALRSIE-UHFFFAOYSA-N 1-(aminomethyl)pyrrolidin-3-one Chemical compound NCN1CCC(=O)C1 ZEEYWNLTALRSIE-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OXNZWNNMJBOZQO-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C12=NC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 OXNZWNNMJBOZQO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9920919.9 | 1999-09-03 | ||
| GBGB9920919.9A GB9920919D0 (en) | 1999-09-03 | 1999-09-03 | Novel compound |
| PCT/GB2000/003358 WO2001017961A2 (en) | 1999-09-03 | 2000-09-01 | Intermediates for the production of naphthyridine-3-carboxylic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2383751A1 CA2383751A1 (en) | 2001-03-15 |
| CA2383751C true CA2383751C (en) | 2010-06-29 |
Family
ID=10860355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2383751A Expired - Lifetime CA2383751C (en) | 1999-09-03 | 2000-09-01 | Intermediates for the production of quinolone carboxylic acid derivatives |
Country Status (30)
| Country | Link |
|---|---|
| US (3) | US6703512B1 (enExample) |
| EP (1) | EP1212321B1 (enExample) |
| JP (1) | JP4208463B2 (enExample) |
| KR (1) | KR100705363B1 (enExample) |
| CN (1) | CN1255402C (enExample) |
| AR (1) | AR029452A1 (enExample) |
| AT (1) | ATE270671T1 (enExample) |
| AU (1) | AU773698B2 (enExample) |
| BR (1) | BRPI0013750B8 (enExample) |
| CA (1) | CA2383751C (enExample) |
| CO (1) | CO5180620A1 (enExample) |
| CZ (1) | CZ2002759A3 (enExample) |
| DE (1) | DE60012028T2 (enExample) |
| DK (1) | DK1212321T3 (enExample) |
| ES (1) | ES2223570T3 (enExample) |
| GB (1) | GB9920919D0 (enExample) |
| HK (1) | HK1046908B (enExample) |
| HU (1) | HU229391B1 (enExample) |
| IL (2) | IL148441A0 (enExample) |
| MX (1) | MXPA02002356A (enExample) |
| MY (1) | MY126789A (enExample) |
| NO (1) | NO322501B1 (enExample) |
| NZ (1) | NZ517601A (enExample) |
| PL (1) | PL206491B1 (enExample) |
| PT (1) | PT1212321E (enExample) |
| SI (1) | SI1212321T1 (enExample) |
| TR (1) | TR200200548T2 (enExample) |
| TW (1) | TWI264435B (enExample) |
| WO (1) | WO2001017961A2 (enExample) |
| ZA (1) | ZA200201779B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2281817C (en) * | 1999-06-29 | 2008-07-29 | Smithkline Beecham Corporation | Methods of use of fluoroquinolone compounds against maxillary sinus pathogenic bacteria |
| GB9920917D0 (en) | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel process |
| GB9920919D0 (en) * | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel compound |
| ATE410225T1 (de) | 2001-08-02 | 2008-10-15 | Lg Life Sciences Ltd | Verfahren zur herstellung von amino-geschützten 4-aminomethylene-pyrrolidin-3-on-derivaten, gemifloxacin und deren salze |
| KR100517638B1 (ko) | 2002-04-08 | 2005-09-28 | 주식회사 엘지생명과학 | 게미플록사신 산염의 새로운 제조방법 |
| JP4563804B2 (ja) * | 2002-07-17 | 2010-10-13 | チバ ホールディング インコーポレーテッド | キナクリドン顔料を製造するための酸化法 |
| KR100653334B1 (ko) * | 2003-03-07 | 2006-12-04 | 주식회사 엘지생명과학 | 4-아미노메틸-3-알콕시이미노피롤리딘 메탄설폰산염의 신규한 제조 방법 |
| US8822934B2 (en) * | 2006-11-03 | 2014-09-02 | Accuray Incorporated | Collimator changer |
| CN104693088B (zh) * | 2013-12-06 | 2018-01-05 | 常州市勇毅生物药业有限公司 | 一种吉米沙星侧链的制备方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57134482A (en) | 1981-02-13 | 1982-08-19 | Dainippon Pharmaceut Co Ltd | 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8- naphthyridine-3-carboxylic acid-3/2 hydrate and its preparation |
| IN162769B (enExample) | 1984-11-13 | 1988-07-09 | Kyorin Seiyaku Kk | |
| NZ222047A (en) | 1986-10-08 | 1991-01-29 | Bristol Myers Co | Quinoline - or naphthyridine - carboxylic acid anti-bacterial agents |
| JPH01100165A (ja) | 1987-10-13 | 1989-04-18 | Shionogi & Co Ltd | オキシムまたはヒドロキシアミン誘導体系抗菌剤 |
| US4920120A (en) | 1988-01-25 | 1990-04-24 | Warner-Lambert Company | Antibacterial agents |
| JPH0356479A (ja) | 1989-07-24 | 1991-03-12 | Takeshi Yokota | 水溶性キノロン誘導体のｐ‐トルエンスルホン酸塩 |
| HU219403B (hu) | 1989-08-16 | 2001-04-28 | Pfizer Inc. | Azabiciklo-csoporttal helyettesített kinolon- és naftiridon-karbonsavak és eljárás ezek előállítására |
| US5137892A (en) | 1990-12-12 | 1992-08-11 | Abbott Laboratories | Quinoline, naphthyridine and pyridobenzoxazine derivatives |
| US5276041A (en) | 1991-11-08 | 1994-01-04 | Kaken Pharmaceutical Co., Ltd. | Oxime derivatives |
| JPH0673056A (ja) | 1992-08-26 | 1994-03-15 | Kaken Pharmaceut Co Ltd | キノリンカルボン酸誘導体およびその塩 |
| US5776944A (en) | 1994-06-16 | 1998-07-07 | Lg Chemical Ltd. | 7-(4-aminomethyl-3-methyloxyiminopyrroplidin-1-yl)-1-cyclopropyl-6-flu oro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid and the process for the preparation thereof |
| DK0688772T3 (da) | 1994-06-16 | 1999-11-01 | Lg Chemical Ltd | Quinolincarboxylsyrederivater med 7-(4-aminomethyl-3-oxim)-pyrrolidinsubstituenter og fremgangsmåde til deres fremstilling |
| JP3449658B2 (ja) | 1994-12-21 | 2003-09-22 | 杏林製薬株式会社 | 安定性に優れた８−アルコキシキノロンカルボン酸水和物並びにその製造方法 |
| CA2223404C (en) | 1995-06-06 | 2001-01-16 | Thomas A. Morris | Novel crystal form of anhydrous 7-(¬1.alpha., 5.alpha., 6.alpha.|-6-amino-3-azabicyclo¬3.1.0|hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, methanesulfonic acid salt |
| EP0843661B1 (en) | 1995-08-11 | 2002-03-27 | Pfizer Inc. | (1s,2s)-1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-1-propanolmethanesulfonate trihydrate |
| JP4316013B2 (ja) | 1996-03-29 | 2009-08-19 | スミスクライン・ビーチャム・コーポレイション | エプロサルタン二水和物ならびにその製法および処方 |
| MA24500A1 (fr) * | 1997-03-21 | 1998-10-01 | Lg Life Sciences Ltd | Derive du sel d'acide carboxylique de naphthyridine . |
| KR100286874B1 (ko) | 1998-03-04 | 2001-04-16 | 성재갑 | 보호된 4-아미노메틸-피롤리딘-3-온의 제조방법 |
| ATE249432T1 (de) | 1998-05-29 | 2003-09-15 | Upjohn Co | 3-((1'-n-methylamino)ethyl-n-benzyl)pyrrolidin- monomethanesulfonat |
| GB9820405D0 (en) | 1998-09-18 | 1998-11-11 | Smithkline Beecham Plc | Process |
| WO2001000209A1 (en) | 1999-06-29 | 2001-01-04 | Smithkline Beecham Corporation | Methods of use of fluoroquinolone compounds against bacteria |
| WO2001015695A1 (en) | 1999-09-01 | 2001-03-08 | Smithkline Beecham Corporation | Methods of use of fluoroquinolone compounds against bacteria |
| GB9920919D0 (en) * | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel compound |
| GB9920917D0 (en) | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel process |
| EP1242079A4 (en) | 1999-09-22 | 2003-01-22 | Smithkline Beecham | Methods of anti-bacterial use of fluoroquinolonic compounds |
| KR20010091379A (ko) | 2000-03-15 | 2001-10-23 | 성재갑 | 7-(4-아미노메틸-3-옥심)피롤리딘 치환체를 갖는 퀴놀린카르복실산 유도체의 신규 제조방법 |
| KR20020018560A (ko) | 2000-09-01 | 2002-03-08 | 성재갑 | 3-아미노메틸-4-ｚ-메톡시이미노피롤리딘의 신규 제조방법 |
-
1999
- 1999-09-03 GB GBGB9920919.9A patent/GB9920919D0/en not_active Ceased
-
2000
- 2000-09-01 AU AU68573/00A patent/AU773698B2/en not_active Ceased
- 2000-09-01 IL IL14844100A patent/IL148441A0/xx active IP Right Grant
- 2000-09-01 TR TR2002/00548T patent/TR200200548T2/xx unknown
- 2000-09-01 PL PL354725A patent/PL206491B1/pl not_active IP Right Cessation
- 2000-09-01 AR ARP000104596A patent/AR029452A1/es active IP Right Grant
- 2000-09-01 DK DK00956706T patent/DK1212321T3/da active
- 2000-09-01 JP JP2001521708A patent/JP4208463B2/ja not_active Expired - Fee Related
- 2000-09-01 MY MYPI20004053 patent/MY126789A/en unknown
- 2000-09-01 EP EP00956706A patent/EP1212321B1/en not_active Expired - Lifetime
- 2000-09-01 HU HU0202733A patent/HU229391B1/hu not_active IP Right Cessation
- 2000-09-01 DE DE60012028T patent/DE60012028T2/de not_active Expired - Lifetime
- 2000-09-01 AT AT00956706T patent/ATE270671T1/de active
- 2000-09-01 BR BRPI0013750A patent/BRPI0013750B8/pt not_active IP Right Cessation
- 2000-09-01 CZ CZ2002759A patent/CZ2002759A3/cs unknown
- 2000-09-01 KR KR1020027002876A patent/KR100705363B1/ko not_active Expired - Lifetime
- 2000-09-01 CO CO00065923A patent/CO5180620A1/es active IP Right Grant
- 2000-09-01 MX MXPA02002356A patent/MXPA02002356A/es active IP Right Grant
- 2000-09-01 WO PCT/GB2000/003358 patent/WO2001017961A2/en not_active Ceased
- 2000-09-01 US US10/088,149 patent/US6703512B1/en not_active Expired - Lifetime
- 2000-09-01 ES ES00956706T patent/ES2223570T3/es not_active Expired - Lifetime
- 2000-09-01 CN CNB008123292A patent/CN1255402C/zh not_active Expired - Lifetime
- 2000-09-01 PT PT00956706T patent/PT1212321E/pt unknown
- 2000-09-01 SI SI200030481T patent/SI1212321T1/xx unknown
- 2000-09-01 HK HK02108460.2A patent/HK1046908B/en not_active IP Right Cessation
- 2000-09-01 NZ NZ517601A patent/NZ517601A/en not_active IP Right Cessation
- 2000-09-01 CA CA2383751A patent/CA2383751C/en not_active Expired - Lifetime
- 2000-09-29 TW TW089120154A patent/TWI264435B/zh not_active IP Right Cessation
-
2002
- 2002-02-28 IL IL148441A patent/IL148441A/en unknown
- 2002-03-01 NO NO20021043A patent/NO322501B1/no not_active IP Right Cessation
- 2002-03-04 ZA ZA200201779A patent/ZA200201779B/xx unknown
-
2003
- 2003-12-23 US US10/742,797 patent/US6803467B2/en not_active Expired - Lifetime
-
2004
- 2004-09-08 US US10/935,357 patent/US20050033064A1/en not_active Abandoned
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