NO327363B1 - Fremgangsmate for fremstilling av organiske forbindelser - Google Patents
Fremgangsmate for fremstilling av organiske forbindelser Download PDFInfo
- Publication number
- NO327363B1 NO327363B1 NO20043586A NO20043586A NO327363B1 NO 327363 B1 NO327363 B1 NO 327363B1 NO 20043586 A NO20043586 A NO 20043586A NO 20043586 A NO20043586 A NO 20043586A NO 327363 B1 NO327363 B1 NO 327363B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- optionally substituted
- aralkyl
- cycloalkyl
- heteroaralkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 34
- 150000002894 organic compounds Chemical class 0.000 title 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims 11
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 239000002585 base Substances 0.000 claims 8
- -1 silyl enol ether Chemical class 0.000 claims 8
- 150000002148 esters Chemical class 0.000 claims 7
- 239000002808 molecular sieve Substances 0.000 claims 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 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 claims 5
- 239000002253 acid Substances 0.000 claims 5
- 229910052783 alkali metal Inorganic materials 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 239000003638 chemical reducing agent Substances 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000004470 heterocyclooxy group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- SSVSTIGWSOEKDK-UHFFFAOYSA-N methoxyborane Chemical compound BOC SSVSTIGWSOEKDK-UHFFFAOYSA-N 0.000 claims 5
- 239000002798 polar solvent Substances 0.000 claims 5
- 229910052708 sodium Inorganic materials 0.000 claims 5
- 239000011734 sodium Substances 0.000 claims 5
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 150000001299 aldehydes Chemical class 0.000 claims 3
- 239000011575 calcium Substances 0.000 claims 3
- 229910052791 calcium Inorganic materials 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 230000003301 hydrolyzing effect Effects 0.000 claims 3
- 239000012442 inert solvent Substances 0.000 claims 3
- 229910052744 lithium Inorganic materials 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 229910052700 potassium Chemical group 0.000 claims 3
- 239000011591 potassium Chemical group 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 claims 2
- 159000000007 calcium salts Chemical class 0.000 claims 2
- 150000002596 lactones Chemical class 0.000 claims 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 claims 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000012448 Lithium borohydride Substances 0.000 claims 1
- YTIITRMGDQULGC-UHFFFAOYSA-N [Ti+6] Chemical compound [Ti+6] YTIITRMGDQULGC-UHFFFAOYSA-N 0.000 claims 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims 1
- 239000001110 calcium chloride Substances 0.000 claims 1
- 229910001628 calcium chloride Inorganic materials 0.000 claims 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- FESAXEDIWWXCNG-UHFFFAOYSA-N diethyl(methoxy)borane Chemical compound CCB(CC)OC FESAXEDIWWXCNG-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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)
- Quinoline Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35231602P | 2002-01-28 | 2002-01-28 | |
| US38318802P | 2002-05-24 | 2002-05-24 | |
| PCT/EP2003/000804 WO2003064382A2 (en) | 2002-01-28 | 2003-01-27 | Process for the manufacture of organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20043586L NO20043586L (no) | 2004-10-07 |
| NO327363B1 true NO327363B1 (no) | 2009-06-15 |
Family
ID=27669055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20043586A NO327363B1 (no) | 2002-01-28 | 2004-08-27 | Fremgangsmate for fremstilling av organiske forbindelser |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US6835838B2 (https=) |
| EP (1) | EP1472227B1 (https=) |
| JP (1) | JP2005516064A (https=) |
| KR (2) | KR20100091267A (https=) |
| CN (2) | CN1625550A (https=) |
| AU (4) | AU2003239294B2 (https=) |
| BR (1) | BR0307236A (https=) |
| CA (1) | CA2472340A1 (https=) |
| CO (1) | CO5601045A2 (https=) |
| EC (1) | ECSP045202A (https=) |
| IL (1) | IL162817A0 (https=) |
| MX (1) | MXPA04007308A (https=) |
| NO (1) | NO327363B1 (https=) |
| NZ (3) | NZ554367A (https=) |
| PL (1) | PL371383A1 (https=) |
| RU (1) | RU2360903C2 (https=) |
| SG (2) | SG157225A1 (https=) |
| WO (1) | WO2003064382A2 (https=) |
| ZA (1) | ZA200405239B (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL159741A0 (en) | 2001-07-13 | 2004-06-20 | Astrazeneca Uk Ltd | Preparation of aminopyrimidine compounds |
| EP1466905B1 (en) * | 2001-11-14 | 2011-05-18 | Nissan Chemical Industries, Ltd. | Process for producing optically active oxoheptenoic acid ester |
| AU2003226971B2 (en) * | 2002-01-31 | 2006-11-30 | Novartis Ag | Process for the manufacture of HMG-CoA reductase inhibitors |
| US7339062B2 (en) * | 2002-09-20 | 2008-03-04 | Nissan Chemical Industries, Ltd. | Method for producing a 3,5-dihydroxy-6-heptenoate |
| DE202004021379U1 (de) * | 2003-02-12 | 2008-02-21 | Ciba Specialty Chemicals Holding Inc. | Kristalline Formen von Pitivastatin Calcium |
| US7851624B2 (en) * | 2003-12-24 | 2010-12-14 | Teva Pharamaceutical Industries Ltd. | Triol form of rosuvastatin and synthesis of rosuvastatin |
| TWI328006B (en) * | 2003-12-26 | 2010-08-01 | Nissan Chemical Ind Ltd | Crystal form of quinoline compound and process for its production |
| CN1763015B (zh) * | 2004-10-22 | 2011-06-22 | 四川抗菌素工业研究所有限公司 | 一种罗舒伐他汀及其药用盐的制备方法及中间体 |
| 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 |
| US8455640B2 (en) * | 2006-05-03 | 2013-06-04 | Msn Laboratories Limited | Process for statins and its pharmaceutically acceptable salts thereof |
| US8404841B2 (en) * | 2006-10-09 | 2013-03-26 | Msn Laboratories Limited | Process for the preparation of statins and their pharmaceutically acceptable salts thereof |
| TW200831469A (en) * | 2006-12-01 | 2008-08-01 | Astrazeneca Uk Ltd | Chemical process |
| US8487105B2 (en) * | 2009-01-19 | 2013-07-16 | Msn Laboratories Limited | Process for preparing pitavastatin, intermediates and pharmaceuctically acceptable salts thereof |
| RU2425034C1 (ru) * | 2010-01-11 | 2011-07-27 | Государственное образовательное учреждение высшего профессионального образования "Кубанский государственный технологический университет" (ГОУ ВПО "КубГТУ") | Способ получения производных (e)-4-(6,7-диметокси-2-метил-3-хинолил)-3-бутен-2-она |
| WO2011086584A2 (en) | 2010-01-18 | 2011-07-21 | Msn Laboratories Limited | Improved process for the preparation of amide intermediates and their use thereof |
| EP2423195A1 (en) | 2010-07-26 | 2012-02-29 | LEK Pharmaceuticals d.d. | Process for the preparation of key intermediates for the synthesis of statins or pharmaceutically acceptable salts thereof |
| WO2012025939A1 (en) * | 2010-08-25 | 2012-03-01 | Cadila Healthcare Limited | Pitavastatin calcium and process for its preparation |
| EP3178812A1 (en) * | 2010-11-12 | 2017-06-14 | Hetero Research Foundation | Novel polymorphs of pitavastatin calcium |
| WO2012140490A2 (en) | 2011-04-11 | 2012-10-18 | Aurobindo Pharma Limited | Process for preparing quinoline derivative |
| CN103755568B (zh) * | 2013-12-10 | 2015-10-28 | 江西科技师范大学 | IeodomycinA和B立体选择性合成方法 |
| CN107949556B (zh) | 2015-08-05 | 2021-12-07 | 株式会社Api | 生产匹伐他汀钙的方法 |
| CN108976168B (zh) * | 2017-06-02 | 2020-09-25 | 浙江京新药业股份有限公司 | 一种匹伐他汀半钙盐晶型及其制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4906624A (en) * | 1987-09-08 | 1990-03-06 | Warner-Lambert Company | 6-(((Substituted)pyridin-3-yl)alkyl)-and alkenyl)-tetrahydro-4-hydroxypyran-2-one inhibitors of cholesterol biosynthesis |
| NZ230121A (en) * | 1988-08-29 | 1993-08-26 | Squibb & Sons Inc | Pyridine and quinoline terminal groups for hmg-coenzyme a reductase inhibitors and pharmaceutical compositions for lowering blood serum cholesterol levels |
| JP3528186B2 (ja) | 1991-06-24 | 2004-05-17 | 日産化学工業株式会社 | 光学活性キノリンメバロン酸のジアステレオマー塩 |
| JP2648897B2 (ja) * | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | ピリミジン誘導体 |
| JP3130342B2 (ja) * | 1991-10-04 | 2001-01-31 | 日産化学工業株式会社 | 動脈硬化性血管内膜肥厚抑制薬 |
| JP3554036B2 (ja) * | 1994-09-06 | 2004-08-11 | 宇部興産株式会社 | 光学活性な７−置換キノリル−３，５−ジヒドロキシ−ヘプト−６−エン酸エステル誘導体の製造方法 |
| EP1466905B1 (en) * | 2001-11-14 | 2011-05-18 | Nissan Chemical Industries, Ltd. | Process for producing optically active oxoheptenoic acid ester |
| ES2385623T3 (es) * | 2007-02-08 | 2012-07-27 | Aurobindo Pharma Limited | Un procedimiento mejorado para la preparación de rosuvastatina cálcica |
-
2003
- 2003-01-24 US US10/350,615 patent/US6835838B2/en not_active Expired - Lifetime
- 2003-01-27 BR BR0307236-3A patent/BR0307236A/pt not_active Application Discontinuation
- 2003-01-27 RU RU2004126448/04A patent/RU2360903C2/ru not_active IP Right Cessation
- 2003-01-27 NZ NZ554367A patent/NZ554367A/en not_active IP Right Cessation
- 2003-01-27 AU AU2003239294A patent/AU2003239294B2/en not_active Ceased
- 2003-01-27 SG SG200605092-6A patent/SG157225A1/en unknown
- 2003-01-27 CA CA002472340A patent/CA2472340A1/en not_active Abandoned
- 2003-01-27 NZ NZ534136A patent/NZ534136A/en not_active IP Right Cessation
- 2003-01-27 CN CNA038028778A patent/CN1625550A/zh active Pending
- 2003-01-27 IL IL16281703A patent/IL162817A0/xx unknown
- 2003-01-27 EP EP03734696.2A patent/EP1472227B1/en not_active Expired - Lifetime
- 2003-01-27 PL PL03371383A patent/PL371383A1/xx unknown
- 2003-01-27 KR KR1020107017248A patent/KR20100091267A/ko not_active Ceased
- 2003-01-27 JP JP2003564005A patent/JP2005516064A/ja active Pending
- 2003-01-27 NZ NZ554366A patent/NZ554366A/en not_active IP Right Cessation
- 2003-01-27 WO PCT/EP2003/000804 patent/WO2003064382A2/en not_active Ceased
- 2003-01-27 SG SG200605094-2A patent/SG161742A1/en unknown
- 2003-01-27 MX MXPA04007308A patent/MXPA04007308A/es active IP Right Grant
- 2003-01-27 CN CNB200510005170XA patent/CN100378081C/zh not_active Expired - Lifetime
- 2003-01-27 KR KR10-2004-7011572A patent/KR20040077883A/ko not_active Ceased
-
2004
- 2004-07-01 ZA ZA2004/05239A patent/ZA200405239B/en unknown
- 2004-07-14 US US10/891,357 patent/US7572917B2/en not_active Expired - Fee Related
- 2004-07-22 EC EC2004005202A patent/ECSP045202A/es unknown
- 2004-08-06 CO CO04076720A patent/CO5601045A2/es not_active Application Discontinuation
- 2004-08-27 NO NO20043586A patent/NO327363B1/no not_active IP Right Cessation
-
2006
- 2006-10-03 AU AU2006225206A patent/AU2006225206B2/en not_active Ceased
- 2006-10-03 AU AU2006225205A patent/AU2006225205B2/en not_active Ceased
-
2009
- 2009-07-02 US US12/497,001 patent/US20090299065A1/en not_active Abandoned
- 2009-08-12 AU AU2009208129A patent/AU2009208129A1/en not_active Abandoned
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