NO328643B1 - Fremgangsmate for fremstilling av 2-(6-substituerte-1,3-dioksan-4-yl) eddiksyrederivater - Google Patents
Fremgangsmate for fremstilling av 2-(6-substituerte-1,3-dioksan-4-yl) eddiksyrederivater Download PDFInfo
- Publication number
- NO328643B1 NO328643B1 NO20043159A NO20043159A NO328643B1 NO 328643 B1 NO328643 B1 NO 328643B1 NO 20043159 A NO20043159 A NO 20043159A NO 20043159 A NO20043159 A NO 20043159A NO 328643 B1 NO328643 B1 NO 328643B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- dioxan
- substituted
- group
- phase transfer
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- -1 2- (6-substituted-1,3-dioxan-4-yl) acetic acid Chemical class 0.000 title abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000001242 acetic acid derivatives Chemical class 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 150000004714 phosphonium salts Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- TXLXWCARAPIXGH-ZJUUUORDSA-N tert-butyl 2-[(4r,6s)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate Chemical compound CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCl)OC(C)(C)O1 TXLXWCARAPIXGH-ZJUUUORDSA-N 0.000 claims description 3
- NGABCYSYENPREI-NEPJUHHUSA-N tert-butyl 2-[(4r,6s)-6-(acetyloxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate Chemical compound CC(=O)OC[C@@H]1C[C@H](CC(=O)OC(C)(C)C)OC(C)(C)O1 NGABCYSYENPREI-NEPJUHHUSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 150000002500 ions Chemical class 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Liquid Crystal Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01000794A EP1323717A1 (en) | 2001-12-27 | 2001-12-27 | Process for the preparation of 2-(6-Substituted-1,3-Dioxane-4-yL) acetic acid derivatives |
| PCT/NL2002/000876 WO2003059901A1 (en) | 2001-12-27 | 2002-12-09 | Process for the preparation of 2-(6-substituted-1,3-dioxane-4-yl) acetic acid derivates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20043159L NO20043159L (no) | 2004-07-23 |
| NO328643B1 true NO328643B1 (no) | 2010-04-19 |
Family
ID=8176121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20043159A NO328643B1 (no) | 2001-12-27 | 2004-07-23 | Fremgangsmate for fremstilling av 2-(6-substituerte-1,3-dioksan-4-yl) eddiksyrederivater |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7718812B2 (ja) |
| EP (2) | EP1323717A1 (ja) |
| JP (2) | JP2005519898A (ja) |
| KR (1) | KR100958367B1 (ja) |
| CN (1) | CN1286830C (ja) |
| AT (1) | ATE319701T1 (ja) |
| AU (1) | AU2002359093B2 (ja) |
| BR (1) | BR0215310A (ja) |
| CA (1) | CA2470647C (ja) |
| CO (1) | CO5590893A2 (ja) |
| DE (1) | DE60209798T2 (ja) |
| HK (1) | HK1069575A1 (ja) |
| HU (1) | HUP0402007A3 (ja) |
| IL (2) | IL162687A0 (ja) |
| IS (1) | IS2407B (ja) |
| MX (1) | MXPA04006306A (ja) |
| NO (1) | NO328643B1 (ja) |
| NZ (1) | NZ533445A (ja) |
| PL (1) | PL207129B1 (ja) |
| RU (1) | RU2301229C2 (ja) |
| UA (1) | UA77467C2 (ja) |
| WO (1) | WO2003059901A1 (ja) |
| ZA (1) | ZA200404482B (ja) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0011120D0 (en) | 2000-05-09 | 2000-06-28 | Avecia Ltd | Process |
| NL1015744C2 (nl) | 2000-07-19 | 2002-01-22 | Dsm Nv | Werkwijze voor de bereiding van 2-(6-gesubstitueerde-1,3-dioxan-4-yl) azijnzuurderivaten. |
| AR034772A1 (es) | 2001-07-13 | 2004-03-17 | Astrazeneca Uk Ltd | Preparacion de los compuestos de aminopirimidina |
| EP1375493A1 (en) | 2002-06-17 | 2004-01-02 | Dsm N.V. | Process for the preparation of an dioxane acetic acid ester |
| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| JP4579821B2 (ja) | 2002-12-16 | 2010-11-10 | アストラゼネカ・ユーケイ・リミテッド | ピリミジン化合物を製造するための方法 |
| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| UY28501A1 (es) * | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
| GB0324791D0 (en) * | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| GB0428328D0 (en) * | 2004-12-24 | 2005-02-02 | Astrazeneca Uk Ltd | Chemical process |
| GB0514078D0 (en) * | 2005-07-08 | 2005-08-17 | Astrazeneca Uk Ltd | Chemical process |
| TW200831469A (en) * | 2006-12-01 | 2008-08-01 | Astrazeneca Uk Ltd | Chemical process |
| GB2482525A (en) | 2010-08-05 | 2012-02-08 | Phoenix Chemicals Ltd | A process for the production of acyloxymethyldioxanylacetic derivatives |
| CN105622566B (zh) * | 2014-11-19 | 2018-07-27 | 上海弈柯莱生物医药科技有限公司 | 一种3,5-二取代羟基-6-取代己酸酯衍生物的制备方法 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB885516A (en) | 1958-01-16 | 1961-12-28 | Arthur Henry Clarkson | Higher fatty acid esters of dextran |
| US3992432A (en) | 1967-04-05 | 1976-11-16 | Continental Oil Company | Phase transfer catalysis of heterogeneous reactions by quaternary salts |
| JPS58164546A (ja) | 1982-03-25 | 1983-09-29 | Sanki Kosan Kk | ｄｌ−マンデル酸ベンジルエステルの製造法 |
| GB9005966D0 (en) | 1990-03-16 | 1990-05-09 | May & Baker Ltd | New compositions of matter |
| JP3097143B2 (ja) | 1991-02-21 | 2000-10-10 | チッソ株式会社 | 生理活性物質合成用光学活性化合物の製造法および光学活性中間体化合物 |
| JP3120292B2 (ja) | 1991-10-18 | 2000-12-25 | イハラケミカル工業株式会社 | 脂肪族カルボン酸ハロメチルエステル類の製造法 |
| WO1993008823A1 (en) | 1991-11-06 | 1993-05-13 | Tanabe Seiyaku Co., Ltd. | Guanidinyl and related cell adhesion modulation compounds |
| US5278313A (en) | 1992-03-27 | 1994-01-11 | E. R. Squibb & Sons, Inc. | Process for the preparation of 1,3-dioxane derivatives useful in the preparation of HMG-COA reductase inhibitors |
| JP3071340B2 (ja) | 1993-06-02 | 2000-07-31 | セントラル硝子株式会社 | ２−クロロ−ピリジンメタノールの製造方法 |
| FR2741620B1 (fr) | 1995-11-28 | 1997-12-26 | Oreal | Procede de preparation de composes a groupement beta-hydroxy -delta-lactone analogues de la (+) compactine et de la (+) mevinoline |
| US6278001B1 (en) | 1995-11-28 | 2001-08-21 | L'oréal | Method for preparing (+) compactin and (+) mevinolin analog compounds having a β-hydroxy-δ-lactone grouping |
| JPH10158199A (ja) | 1996-10-02 | 1998-06-16 | Dai Ichi Seiyaku Co Ltd | カルボン酸化合物のエステル化法 |
| KR100654115B1 (ko) * | 1998-08-05 | 2006-12-05 | 카네카 코포레이션 | 광학 활성 2-[6-(히드록시메틸)-1,3-디옥산-4-일]아세트산유도체의 제조 방법 |
| GB9903472D0 (en) | 1999-02-17 | 1999-04-07 | Zeneca Ltd | Chemical process |
| HU227840B1 (en) | 1999-05-06 | 2012-05-02 | Egis Gyogyszergyar Nyilvanosan M Kod Ruszvunytarsasag | Intermediates of atorvastatin synthesis and process for producing them |
| WO2001072706A1 (en) | 2000-03-28 | 2001-10-04 | Biocon India Limited | Synthesis of [r-(r*,r*)]-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-heptanoic acid hemi calcium salt (atorvastatin) |
| GB0011120D0 (en) | 2000-05-09 | 2000-06-28 | Avecia Ltd | Process |
| NL1015744C2 (nl) | 2000-07-19 | 2002-01-22 | Dsm Nv | Werkwijze voor de bereiding van 2-(6-gesubstitueerde-1,3-dioxan-4-yl) azijnzuurderivaten. |
| AR034772A1 (es) | 2001-07-13 | 2004-03-17 | Astrazeneca Uk Ltd | Preparacion de los compuestos de aminopirimidina |
| BR0215602A (pt) | 2002-02-25 | 2004-12-07 | Biocon Ltd | ésteres de boronato |
| EP1375493A1 (en) | 2002-06-17 | 2004-01-02 | Dsm N.V. | Process for the preparation of an dioxane acetic acid ester |
| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| JP4579821B2 (ja) | 2002-12-16 | 2010-11-10 | アストラゼネカ・ユーケイ・リミテッド | ピリミジン化合物を製造するための方法 |
| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| WO2004113314A1 (en) | 2003-06-23 | 2004-12-29 | Biocon Limited | Novel boronate esters |
| UY28501A1 (es) | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
| GB0321827D0 (en) | 2003-09-18 | 2003-10-15 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0324791D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| JP4266879B2 (ja) | 2004-05-12 | 2009-05-20 | 大阪瓦斯株式会社 | ガス化炉及び複合リサイクル装置 |
| US9626437B2 (en) * | 2004-06-10 | 2017-04-18 | International Business Machines Corporation | Search scheduling and delivery tool for scheduling a search using a search framework profile |
| GB0428328D0 (en) | 2004-12-24 | 2005-02-02 | Astrazeneca Uk Ltd | Chemical process |
-
2001
- 2001-12-27 EP EP01000794A patent/EP1323717A1/en not_active Withdrawn
-
2002
- 2002-09-12 UA UA20040604878A patent/UA77467C2/uk unknown
- 2002-12-09 HU HU0402007A patent/HUP0402007A3/hu unknown
- 2002-12-09 DE DE60209798T patent/DE60209798T2/de not_active Expired - Lifetime
- 2002-12-09 AT AT02793596T patent/ATE319701T1/de not_active IP Right Cessation
- 2002-12-09 BR BR0215310-6A patent/BR0215310A/pt not_active Application Discontinuation
- 2002-12-09 WO PCT/NL2002/000876 patent/WO2003059901A1/en active IP Right Grant
- 2002-12-09 MX MXPA04006306A patent/MXPA04006306A/es active IP Right Grant
- 2002-12-09 JP JP2003560004A patent/JP2005519898A/ja active Pending
- 2002-12-09 AU AU2002359093A patent/AU2002359093B2/en not_active Ceased
- 2002-12-09 IL IL16268702A patent/IL162687A0/xx active IP Right Grant
- 2002-12-09 KR KR1020047010040A patent/KR100958367B1/ko not_active IP Right Cessation
- 2002-12-09 NZ NZ533445A patent/NZ533445A/en not_active IP Right Cessation
- 2002-12-09 US US10/501,250 patent/US7718812B2/en not_active Expired - Lifetime
- 2002-12-09 EP EP02793596A patent/EP1461331B9/en not_active Expired - Lifetime
- 2002-12-09 CN CNB028262018A patent/CN1286830C/zh not_active Expired - Lifetime
- 2002-12-09 RU RU2004118057/04A patent/RU2301229C2/ru not_active IP Right Cessation
- 2002-12-09 CA CA2470647A patent/CA2470647C/en not_active Expired - Fee Related
- 2002-12-09 PL PL370223A patent/PL207129B1/pl not_active IP Right Cessation
-
2004
- 2004-06-07 ZA ZA200404482A patent/ZA200404482B/en unknown
- 2004-06-22 IL IL162687A patent/IL162687A/en not_active IP Right Cessation
- 2004-06-22 IS IS7332A patent/IS2407B/is unknown
- 2004-06-22 CO CO04058284A patent/CO5590893A2/es not_active Application Discontinuation
- 2004-07-23 NO NO20043159A patent/NO328643B1/no not_active IP Right Cessation
-
2005
- 2005-03-10 HK HK05102090A patent/HK1069575A1/xx not_active IP Right Cessation
-
2010
- 2010-02-09 JP JP2010026513A patent/JP2010132690A/ja active Pending
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