ZA200502159B - Process for the manufacture of valsartan. - Google Patents
Process for the manufacture of valsartan. Download PDFInfo
- Publication number
- ZA200502159B ZA200502159B ZA200502159A ZA200502159A ZA200502159B ZA 200502159 B ZA200502159 B ZA 200502159B ZA 200502159 A ZA200502159 A ZA 200502159A ZA 200502159 A ZA200502159 A ZA 200502159A ZA 200502159 B ZA200502159 B ZA 200502159B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compound
- salt
- protecting group
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000004072 C09CA03 - Valsartan Substances 0.000 title description 3
- 229960004699 valsartan Drugs 0.000 title description 3
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- 238000006268 reductive amination reaction Methods 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- -1 carboxy - Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 7
- 239000003638 chemical reducing agent Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 101100422638 Caenorhabditis elegans syx-4 gene Proteins 0.000 claims 1
- 240000000233 Melia azedarach Species 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000000852 hydrogen donor Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 229940125364 angiotensin receptor blocker Drugs 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000003536 tetrazoles Chemical group 0.000 description 6
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- IJIBRSFAXRFPPN-UHFFFAOYSA-N 5-bromo-2-methoxybenzaldehyde Chemical compound COC1=CC=C(Br)C=C1C=O IJIBRSFAXRFPPN-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 239000002083 C09CA01 - Losartan Substances 0.000 description 1
- 239000002080 C09CA02 - Eprosartan Substances 0.000 description 1
- 239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
- 239000002081 C09CA05 - Tasosartan Substances 0.000 description 1
- 239000002053 C09CA06 - Candesartan Substances 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 239000005480 Olmesartan Substances 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical group C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- LNENVNGQOUBOIX-UHFFFAOYSA-N azidosilane Chemical compound [SiH3]N=[N+]=[N-] LNENVNGQOUBOIX-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960000932 candesartan Drugs 0.000 description 1
- SGZAIDDFHDDFJU-UHFFFAOYSA-N candesartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SGZAIDDFHDDFJU-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229960004563 eprosartan Drugs 0.000 description 1
- OROAFUQRIXKEMV-LDADJPATSA-N eprosartan Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 OROAFUQRIXKEMV-LDADJPATSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229960002198 irbesartan Drugs 0.000 description 1
- YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
- 229960004773 losartan Drugs 0.000 description 1
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VTRAEEWXHOVJFV-UHFFFAOYSA-N olmesartan Chemical compound CCCC1=NC(C(C)(C)O)=C(C(O)=O)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 VTRAEEWXHOVJFV-UHFFFAOYSA-N 0.000 description 1
- 229960005117 olmesartan Drugs 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960000651 tasosartan Drugs 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0222056.4A GB0222056D0 (en) | 2002-09-23 | 2002-09-23 | Process for the manufacture of organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200502159B true ZA200502159B (en) | 2005-09-21 |
Family
ID=9944606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200502159A ZA200502159B (en) | 2002-09-23 | 2005-03-15 | Process for the manufacture of valsartan. |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US20060069268A1 (enExample) |
| EP (2) | EP1878729A1 (enExample) |
| JP (2) | JP4787498B2 (enExample) |
| KR (2) | KR20050057529A (enExample) |
| CN (2) | CN100357279C (enExample) |
| AR (1) | AR041360A1 (enExample) |
| AU (1) | AU2003270241B2 (enExample) |
| BR (1) | BR0314132A (enExample) |
| CA (1) | CA2502629A1 (enExample) |
| CY (1) | CY1107878T1 (enExample) |
| DE (1) | DE60317690T2 (enExample) |
| DK (1) | DK1546122T3 (enExample) |
| EC (2) | ECSP055695A (enExample) |
| ES (1) | ES2295623T3 (enExample) |
| GB (1) | GB0222056D0 (enExample) |
| IL (1) | IL167426A (enExample) |
| MX (1) | MXPA05003140A (enExample) |
| MY (1) | MY138618A (enExample) |
| NO (2) | NO20051970L (enExample) |
| NZ (2) | NZ538927A (enExample) |
| PE (2) | PE20050088A1 (enExample) |
| PL (1) | PL374862A1 (enExample) |
| PT (1) | PT1546122E (enExample) |
| RU (2) | RU2348619C2 (enExample) |
| SG (1) | SG155049A1 (enExample) |
| SI (1) | SI1546122T1 (enExample) |
| TW (2) | TWI329106B (enExample) |
| WO (1) | WO2004026847A1 (enExample) |
| ZA (1) | ZA200502159B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040242661A1 (en) * | 2003-03-17 | 2004-12-02 | Igor Rukhman | Polymorphs of valsartan |
| US7199144B2 (en) | 2003-04-21 | 2007-04-03 | Teva Pharmaceuticals Industries, Ltd. | Process for the preparation of valsartan and intermediates thereof |
| TW200505879A (en) | 2003-04-21 | 2005-02-16 | Teva Pharma | Process for the preparation of valsartan |
| EP1556363A2 (en) * | 2003-04-21 | 2005-07-27 | Teva Pharmaceutical Industries Limited | Process for the preparation of valsartan and intermediates thereof |
| GB0316546D0 (en) | 2003-07-15 | 2003-08-20 | Novartis Ag | Process for the manufacture of organic compounds |
| GB0402262D0 (en) * | 2004-02-02 | 2004-03-10 | Novartis Ag | Process for the manufacture of organic compounds |
| EP1661891A1 (en) * | 2004-11-30 | 2006-05-31 | KRKA, D.D., Novo Mesto | A process for the synthesis of valsartan |
| GB0514206D0 (en) | 2005-07-11 | 2005-08-17 | Novartis Ag | Organic compounds |
| ES2288376B1 (es) * | 2005-10-20 | 2008-11-01 | Inke, S.A. | Procedimiento para la obtencion de intermedios utiles en la obtencion de un compuesto farmaceuticamente activo. |
| WO2007057919A2 (en) * | 2005-10-25 | 2007-05-24 | Alembic Limited | An improved process for preparation of (s)-n-(1-carboxy-2-methyl-prop-1-yl)-n-pentanoyl-n-[2'-(1h-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine |
| EP2057132A2 (en) * | 2006-07-03 | 2009-05-13 | Aurobindo Pharma Limited | Process for the preparation of the angiotensin ii antagonist valsartan |
| ES2315141B1 (es) * | 2006-11-23 | 2009-12-22 | Quimica Sintetica, S.A | Procedimiento para la preparacion de cardesartan cilexetilo en forma cristalina. |
| CN101200455B (zh) * | 2007-09-29 | 2010-08-18 | 泰兴市江神化工有限公司 | 沙坦类治疗高血压药物主环5-(4'-甲酰基联苯-2-基)-1h-四氮唑的制备方法 |
| US7943794B2 (en) * | 2008-02-13 | 2011-05-17 | Ranbaxy Laboratories Limited | Processes for the preparation of intermediates of valsartan |
| KR101012135B1 (ko) * | 2008-12-18 | 2011-02-07 | 주식회사 대희화학 | 발사르탄 메틸 에스테르의 제조방법 |
| EP2316821A1 (en) | 2009-10-27 | 2011-05-04 | Novartis AG | Process for the manufacture of organic compounds |
| AR082435A1 (es) * | 2010-08-03 | 2012-12-05 | Novartis Ag | Valsartan altamente cristalino |
| CN102351804B (zh) * | 2011-09-30 | 2013-07-31 | 浙江新赛科药业有限公司 | 一种缬沙坦消旋体的回收方法 |
| CN103554047A (zh) * | 2013-10-11 | 2014-02-05 | 镇江市高等专科学校 | 制备缬沙坦的方法 |
| CN103923028B (zh) * | 2014-05-04 | 2017-05-24 | 青岛雪洁助剂有限公司 | 一种缬沙坦甲酯的制备方法 |
| CN104072433A (zh) * | 2014-07-16 | 2014-10-01 | 南京正大天晴制药有限公司 | 一种缬沙坦的水解杂质化合物及其制备方法、检测方法和用途 |
| CN104151199A (zh) * | 2014-08-13 | 2014-11-19 | 苏州卫生职业技术学院 | 一种缬沙坦的合成方法 |
| CN104844476B (zh) * | 2015-04-03 | 2016-08-24 | 李凌 | 一种医药中间体联苯类化合物的合成方法 |
| CN112014479A (zh) * | 2019-05-28 | 2020-12-01 | 珠海润都制药股份有限公司 | 一种缬沙坦中正戊酰氯的检测方法 |
| CN116655498B (zh) * | 2023-05-24 | 2025-01-28 | 江苏阿尔法集团福瑞药业(宿迁)有限公司 | 一种沙库巴曲中间体的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820843A (en) * | 1987-05-22 | 1989-04-11 | E. I. Du Pont De Nemours And Company | Tetrazole intermediates to antihypertensive compounds |
| IL97219A (en) * | 1990-02-19 | 1995-12-08 | Ciba Geigy Ag | Biphenyl substituted aliphatic amino compounds process for their preparation and pharmaceutical compositions containing them |
| US5260325A (en) * | 1991-08-19 | 1993-11-09 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking tertiary amides |
| EP0550313A1 (fr) * | 1991-12-30 | 1993-07-07 | Synthelabo | Nouveaux dérivés de 2-(tétrazol-5-yl)-(1,1'-biphényle), leur préparation et leur utilisation comme intermédiaires de synthèse |
| FR2688503B1 (fr) * | 1992-03-16 | 1994-05-06 | Synthelabo | Procede de preparation de derives de 2-(tetrazol-5-yl)-[1,1'-biphenyle]. |
| US5284957A (en) * | 1992-09-03 | 1994-02-08 | Eli Lilly And Company | Excitatory amino acid receptor antagonists |
| JPH08165292A (ja) * | 1993-10-07 | 1996-06-25 | Techno Res Kk | アデニン誘導体、その製造法及び用途 |
| US5412102A (en) * | 1994-05-27 | 1995-05-02 | Syntex (U.S.A.) Inc. | Processes for preparing 1-butyl-2-[2'-(2H-tetrazol-5-yl) biphenyl-4-ylmethyl]-1H-indole-3-carboxylic acid |
| US5468867A (en) * | 1994-05-27 | 1995-11-21 | Syntex (U.S.A.) Inc. | Process for preparing1-butyl-2-[2'-(2H-tetrazol-5-yl)biphenyl-4-ylmethyl1-1H-indole-3-carboxylic acid |
| DK0782996T3 (da) * | 1994-09-20 | 1999-09-20 | Wakunaga Seiyaku Kk | Fremgangsmåde til fremstilling af N-biphenylmethylthiadiazolinderivat eller salt deraf og mellemprodukt til fremstilling af |
| CA2223783A1 (en) * | 1995-06-07 | 1996-12-19 | Michel Bernatchez | Process for preparation of biphenyl derivatives |
| US6071931A (en) * | 1995-10-06 | 2000-06-06 | Novartis Ag | AT1 -receptor antagonists for preventing and treating postischemic renal failure and for protecting ischemic kidneys |
| CN1137887C (zh) * | 2000-04-07 | 2004-02-11 | 常州四药制药有限公司 | 一种合成缬沙坦的改进方法 |
| US20030207930A1 (en) * | 2000-07-19 | 2003-11-06 | Erwin Marti | Valsartan salts |
| JP4537678B2 (ja) * | 2003-09-04 | 2010-09-01 | 住友化学株式会社 | ２’−（１ｈ−テトラゾール−５−イル）ビフェニル−４−カルボアルデヒド結晶およびその製造方法 |
| GB0402262D0 (en) * | 2004-02-02 | 2004-03-10 | Novartis Ag | Process for the manufacture of organic compounds |
-
2002
- 2002-09-23 GB GBGB0222056.4A patent/GB0222056D0/en not_active Ceased
-
2003
- 2003-09-22 CN CNB038245140A patent/CN100357279C/zh not_active Expired - Fee Related
- 2003-09-22 MX MXPA05003140A patent/MXPA05003140A/es active IP Right Grant
- 2003-09-22 WO PCT/EP2003/010543 patent/WO2004026847A1/en not_active Ceased
- 2003-09-22 EP EP07113176A patent/EP1878729A1/en not_active Withdrawn
- 2003-09-22 RU RU2005112444/04A patent/RU2348619C2/ru not_active IP Right Cessation
- 2003-09-22 JP JP2004537146A patent/JP4787498B2/ja not_active Expired - Fee Related
- 2003-09-22 NZ NZ538927A patent/NZ538927A/en not_active IP Right Cessation
- 2003-09-22 TW TW092126088A patent/TWI329106B/zh not_active IP Right Cessation
- 2003-09-22 CN CN2007101692527A patent/CN101153027B/zh not_active Expired - Fee Related
- 2003-09-22 NZ NZ566863A patent/NZ566863A/en not_active IP Right Cessation
- 2003-09-22 PL PL03374862A patent/PL374862A1/xx not_active Application Discontinuation
- 2003-09-22 KR KR1020057004873A patent/KR20050057529A/ko not_active Ceased
- 2003-09-22 EP EP03750599A patent/EP1546122B8/en not_active Revoked
- 2003-09-22 BR BR0314132-2A patent/BR0314132A/pt not_active IP Right Cessation
- 2003-09-22 DK DK03750599T patent/DK1546122T3/da active
- 2003-09-22 DE DE60317690T patent/DE60317690T2/de not_active Expired - Lifetime
- 2003-09-22 TW TW098146486A patent/TWI338003B/zh not_active IP Right Cessation
- 2003-09-22 PT PT03750599T patent/PT1546122E/pt unknown
- 2003-09-22 KR KR1020117002725A patent/KR20110015703A/ko not_active Ceased
- 2003-09-22 ES ES03750599T patent/ES2295623T3/es not_active Expired - Lifetime
- 2003-09-22 AU AU2003270241A patent/AU2003270241B2/en not_active Ceased
- 2003-09-22 MY MYPI20033603A patent/MY138618A/en unknown
- 2003-09-22 RU RU2008133680/04A patent/RU2412173C2/ru not_active IP Right Cessation
- 2003-09-22 CA CA002502629A patent/CA2502629A1/en not_active Abandoned
- 2003-09-22 SG SG200702272-6A patent/SG155049A1/en unknown
- 2003-09-22 SI SI200331125T patent/SI1546122T1/sl unknown
- 2003-09-22 US US10/528,323 patent/US20060069268A1/en not_active Abandoned
- 2003-09-23 PE PE2003000976A patent/PE20050088A1/es not_active Application Discontinuation
- 2003-09-23 AR ARP030103458A patent/AR041360A1/es unknown
- 2003-09-23 PE PE2008001800A patent/PE20091387A1/es not_active Application Discontinuation
-
2005
- 2005-03-14 IL IL167426A patent/IL167426A/en not_active IP Right Cessation
- 2005-03-15 ZA ZA200502159A patent/ZA200502159B/en unknown
- 2005-03-21 EC EC2005005695A patent/ECSP055695A/es unknown
- 2005-04-22 NO NO20051970A patent/NO20051970L/no not_active Application Discontinuation
-
2008
- 2008-02-04 CY CY20081100145T patent/CY1107878T1/el unknown
- 2008-12-23 US US12/317,426 patent/US20090111995A1/en not_active Abandoned
-
2010
- 2010-02-11 EC EC2010005695A patent/ECSP105695A/es unknown
- 2010-06-15 US US12/815,704 patent/US20100249429A1/en not_active Abandoned
- 2010-08-02 JP JP2010173583A patent/JP2010254709A/ja active Pending
-
2011
- 2011-06-15 NO NO20110856A patent/NO20110856L/no not_active Application Discontinuation
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