NO328946B1 - Fremgangsmate for fremstilling av dioksan eddiksyreestere - Google Patents
Fremgangsmate for fremstilling av dioksan eddiksyreestere Download PDFInfo
- Publication number
- NO328946B1 NO328946B1 NO20045491A NO20045491A NO328946B1 NO 328946 B1 NO328946 B1 NO 328946B1 NO 20045491 A NO20045491 A NO 20045491A NO 20045491 A NO20045491 A NO 20045491A NO 328946 B1 NO328946 B1 NO 328946B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- acid chloride
- group
- ester
- alcohol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- QMHVBFCNECLXNF-UHFFFAOYSA-N acetic acid;1,4-dioxane Chemical class CC(O)=O.C1COCCO1 QMHVBFCNECLXNF-UHFFFAOYSA-N 0.000 title 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims abstract description 26
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000002148 esters Chemical class 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- 239000012442 inert solvent Substances 0.000 claims abstract description 3
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical group ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000003513 alkali Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- -1 sulphonic acid quaternary ammonium Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000012776 robust process Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 238000005406 washing Methods 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)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02100715A EP1375493A1 (en) | 2002-06-17 | 2002-06-17 | Process for the preparation of an dioxane acetic acid ester |
| PCT/NL2003/000435 WO2003106447A1 (en) | 2002-06-17 | 2003-06-12 | Process for the preparation of dioxane acetic acid esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20045491L NO20045491L (no) | 2005-01-14 |
| NO328946B1 true NO328946B1 (no) | 2010-06-28 |
Family
ID=29716908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20045491A NO328946B1 (no) | 2002-06-17 | 2004-12-16 | Fremgangsmate for fremstilling av dioksan eddiksyreestere |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7442811B2 (el) |
| EP (2) | EP1375493A1 (el) |
| JP (1) | JP4632784B2 (el) |
| KR (1) | KR101008920B1 (el) |
| CN (2) | CN1662520B (el) |
| AT (1) | ATE348825T1 (el) |
| AU (1) | AU2003277230B2 (el) |
| BR (1) | BR0311884A (el) |
| CA (1) | CA2490205C (el) |
| CY (1) | CY1107344T1 (el) |
| DE (1) | DE60310559T2 (el) |
| DK (1) | DK1515962T3 (el) |
| EG (1) | EG24561A (el) |
| ES (1) | ES2278174T3 (el) |
| HK (1) | HK1073303A1 (el) |
| IL (1) | IL165767A0 (el) |
| IS (1) | IS2477B (el) |
| MX (1) | MXPA04012651A (el) |
| NO (1) | NO328946B1 (el) |
| NZ (1) | NZ537260A (el) |
| PL (1) | PL207130B1 (el) |
| PT (1) | PT1515962E (el) |
| RU (1) | RU2315761C2 (el) |
| SI (1) | SI1515962T1 (el) |
| UA (1) | UA79970C2 (el) |
| WO (1) | WO2003106447A1 (el) |
| ZA (1) | ZA200409986B (el) |
Families Citing this family (16)
| 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. |
| ATE349431T1 (de) | 2001-07-13 | 2007-01-15 | Astrazeneca Uk Ltd | Herstellung von aminopyrimidinverbindungen |
| EP1323717A1 (en) | 2001-12-27 | 2003-07-02 | Dsm N.V. | Process for the preparation of 2-(6-Substituted-1,3-Dioxane-4-yL) acetic acid derivatives |
| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| WO2004054986A2 (en) | 2002-12-16 | 2004-07-01 | Astrazeneca Uk Limited | Process for the preparation of pyrimidine compounds |
| 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 |
| CN105198856B (zh) * | 2014-06-27 | 2017-10-13 | 上海弈柯莱生物医药科技有限公司 | 一种2‑(6‑取代1,3‑二噁烷‑4‑基)乙酸衍生物的制备方法 |
| RU2596623C1 (ru) * | 2015-07-20 | 2016-09-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Уфимский государственный нефтяной технический университет" | Способ получения 1,4-диоксанкарбоксилатов |
| CN111675689B (zh) * | 2020-06-16 | 2021-08-24 | 浙江工业大学 | 一种瑞舒伐他汀中间体的化学合成方法 |
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 |
| US3325466A (en) * | 1961-01-11 | 1967-06-13 | American Cyanamid Co | Tertiary butyl group as a carboxyl protecting group in the synthesis of peptides |
| 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 |
| EP0604483A1 (en) | 1991-09-20 | 1994-07-06 | Zeneca Limited | Process for the preparation of enantiomerically pure 4-hydroxytetrahydro-2-pyranone derivatives |
| 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 |
| US5795749A (en) | 1995-04-05 | 1998-08-18 | The Scripps Research Institution | Use of 2-deoxyribose-5-phosphate aldolase to prepare 2-deoxyfucose, analogues and derivatives |
| GB9523924D0 (en) | 1995-11-23 | 1996-01-24 | Zeneca Ltd | Production of optically active 2-substituted tetrahydropyran-4-ones |
| 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 |
| CA2329893A1 (en) | 1998-04-30 | 1999-11-11 | Kaneka Corporation | Process for producing 6-cyanomethyl-1,3-dioxane-4-acetic acid derivatives |
| EP1619191B1 (en) | 1998-08-05 | 2010-10-27 | Kaneka Corporation | Process for producing optically active 2-[6-(hydroxymethyl)-1,3-dioxan-4-yl] acetic acid derivatives |
| JP4440476B2 (ja) * | 1998-12-10 | 2010-03-24 | 株式会社カネカ | シンバスタチンの製造方法 |
| 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 |
| KR20010072175A (ko) * | 1999-06-04 | 2001-07-31 | 후루타 타케시 | 5-히드록시-3-옥소펜탄산 유도체 제조방법 |
| AU2000254249A1 (en) | 2000-03-28 | 2001-10-08 | Biocon India Limited | Synthesis of (r-(r*,r*))-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1- |
| 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. |
| ATE349431T1 (de) | 2001-07-13 | 2007-01-15 | Astrazeneca Uk Ltd | Herstellung von aminopyrimidinverbindungen |
| EP1323717A1 (en) | 2001-12-27 | 2003-07-02 | Dsm N.V. | Process for the preparation of 2-(6-Substituted-1,3-Dioxane-4-yL) acetic acid derivatives |
| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| WO2004054986A2 (en) | 2002-12-16 | 2004-07-01 | Astrazeneca Uk Limited | Process for the preparation of pyrimidine compounds |
| 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 |
| TWI276043B (en) | 2004-09-09 | 2007-03-11 | Seiko Epson Corp | Display apparatus |
| GB0428328D0 (en) | 2004-12-24 | 2005-02-02 | Astrazeneca Uk Ltd | Chemical process |
-
2002
- 2002-06-17 EP EP02100715A patent/EP1375493A1/en not_active Withdrawn
-
2003
- 2003-06-12 DE DE60310559T patent/DE60310559T2/de not_active Expired - Lifetime
- 2003-06-12 WO PCT/NL2003/000435 patent/WO2003106447A1/en active IP Right Grant
- 2003-06-12 MX MXPA04012651A patent/MXPA04012651A/es active IP Right Grant
- 2003-06-12 EP EP03741639A patent/EP1515962B1/en not_active Expired - Lifetime
- 2003-06-12 CA CA2490205A patent/CA2490205C/en not_active Expired - Fee Related
- 2003-06-12 KR KR1020047020617A patent/KR101008920B1/ko not_active IP Right Cessation
- 2003-06-12 ES ES03741639T patent/ES2278174T3/es not_active Expired - Lifetime
- 2003-06-12 PL PL375077A patent/PL207130B1/pl not_active IP Right Cessation
- 2003-06-12 RU RU2004139042/04A patent/RU2315761C2/ru not_active IP Right Cessation
- 2003-06-12 AU AU2003277230A patent/AU2003277230B2/en not_active Ceased
- 2003-06-12 PT PT03741639T patent/PT1515962E/pt unknown
- 2003-06-12 CN CN038140373A patent/CN1662520B/zh not_active Expired - Lifetime
- 2003-06-12 DK DK03741639T patent/DK1515962T3/da active
- 2003-06-12 JP JP2004513279A patent/JP4632784B2/ja not_active Expired - Fee Related
- 2003-06-12 NZ NZ537260A patent/NZ537260A/en not_active IP Right Cessation
- 2003-06-12 CN CN2010101725560A patent/CN101812045B/zh not_active Expired - Lifetime
- 2003-06-12 SI SI200330658T patent/SI1515962T1/sl unknown
- 2003-06-12 US US10/518,164 patent/US7442811B2/en not_active Expired - Fee Related
- 2003-06-12 BR BR0311884-3A patent/BR0311884A/pt not_active IP Right Cessation
- 2003-06-12 AT AT03741639T patent/ATE348825T1/de active
- 2003-12-06 UA UAA200500156A patent/UA79970C2/uk unknown
-
2004
- 2004-12-09 ZA ZA200409986A patent/ZA200409986B/xx unknown
- 2004-12-14 IL IL16576704A patent/IL165767A0/xx not_active IP Right Cessation
- 2004-12-15 EG EGNA2004000143 patent/EG24561A/xx active
- 2004-12-16 NO NO20045491A patent/NO328946B1/no not_active IP Right Cessation
- 2004-12-28 IS IS7617A patent/IS2477B/is unknown
-
2005
- 2005-07-13 HK HK05105964A patent/HK1073303A1/xx not_active IP Right Cessation
-
2007
- 2007-02-16 CY CY20071100215T patent/CY1107344T1/el unknown
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