ZA200404080B - Crystalline venlafaxine base and novel polymorphs of venlafaxine hydrochloride, processes for preparing thereof - Google Patents
Crystalline venlafaxine base and novel polymorphs of venlafaxine hydrochloride, processes for preparing thereof Download PDFInfo
- Publication number
- ZA200404080B ZA200404080B ZA200404080A ZA200404080A ZA200404080B ZA 200404080 B ZA200404080 B ZA 200404080B ZA 200404080 A ZA200404080 A ZA 200404080A ZA 200404080 A ZA200404080 A ZA 200404080A ZA 200404080 B ZA200404080 B ZA 200404080B
- Authority
- ZA
- South Africa
- Prior art keywords
- venlafaxine
- venlafaxine hydrochloride
- hydrochloride
- base
- preparing
- Prior art date
Links
- QYRYFNHXARDNFZ-UHFFFAOYSA-N venlafaxine hydrochloride Chemical compound [H+].[Cl-].C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 QYRYFNHXARDNFZ-UHFFFAOYSA-N 0.000 title claims description 112
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 title claims description 72
- 229960004688 venlafaxine Drugs 0.000 title claims description 71
- 238000000034 method Methods 0.000 title claims description 42
- 229960002416 venlafaxine hydrochloride Drugs 0.000 title description 88
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 65
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 30
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000012456 homogeneous solution Substances 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 239000002585 base Substances 0.000 description 33
- 238000002360 preparation method Methods 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000013078 crystal Substances 0.000 description 23
- 238000001035 drying Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000012453 solvate Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 18
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 12
- 229940093499 ethyl acetate Drugs 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 239000000725 suspension Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000012296 anti-solvent Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 230000001376 precipitating effect Effects 0.000 description 4
- SUQHIQRIIBKNOR-UHFFFAOYSA-N N,N-didesmethylvenlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN)C1(O)CCCCC1 SUQHIQRIIBKNOR-UHFFFAOYSA-N 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- NTKXIDDUCSFBBF-UHFFFAOYSA-N 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(CN)C1(O)CCCCC1 NTKXIDDUCSFBBF-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- 102100025490 Slit homolog 1 protein Human genes 0.000 description 1
- 101710123186 Slit homolog 1 protein Proteins 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
- C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
- C07C217/70—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/000,428 US20020183553A1 (en) | 2000-10-19 | 2001-11-30 | Crystalline venlafaxine base and novel polymorphs of venlafaxine hydrochloride, processes for preparing thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200404080B true ZA200404080B (en) | 2007-12-27 |
Family
ID=21691493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200404080A ZA200404080B (en) | 2001-11-30 | 2002-11-20 | Crystalline venlafaxine base and novel polymorphs of venlafaxine hydrochloride, processes for preparing thereof |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US20020183553A1 (xx) |
| EP (1) | EP1474379A4 (xx) |
| JP (1) | JP2005511668A (xx) |
| KR (1) | KR20040068163A (xx) |
| CN (2) | CN1617848A (xx) |
| AU (1) | AU2002365874A1 (xx) |
| CA (1) | CA2468728A1 (xx) |
| HR (1) | HRP20040565A2 (xx) |
| HU (1) | HUP0700037A2 (xx) |
| IL (1) | IL162171A0 (xx) |
| IS (1) | IS7289A (xx) |
| MX (1) | MXPA04005193A (xx) |
| NO (1) | NO20042732L (xx) |
| PL (1) | PL374273A1 (xx) |
| WO (1) | WO2003048082A2 (xx) |
| ZA (1) | ZA200404080B (xx) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1620420A (zh) * | 2000-10-19 | 2005-05-25 | 特瓦制药工业有限公司 | 结晶文拉法辛碱和新的文拉法辛盐酸盐多晶型物及其制备方法 |
| CA2426393C (en) * | 2000-10-31 | 2012-05-29 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of venlafaxine hydrochloride |
| UA77234C2 (en) * | 2001-12-05 | 2006-11-15 | Wyeth Corp | Monohydrate of venlafaxine hydrochloride and methods for its preparation (variants) |
| CA2467593A1 (en) * | 2001-12-05 | 2003-06-19 | Wyeth | Novel crystalline polymorph of venlafaxine hydrochloride and methods for the preparation thereof |
| AU2003226748A1 (en) * | 2002-03-28 | 2003-10-13 | Synthon B.V. | Compositions of venlafaxine base |
| DE10359154A1 (de) * | 2003-12-16 | 2005-07-28 | Krka Tovarna Zdravil, D.D. | Verfahren zur Herstellung von Venlafaxin und Venlafaxinhydrochlorid der Form I |
| WO2007047972A2 (en) * | 2005-10-19 | 2007-04-26 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of highly pure 1-[2-dimethylamino-(4-methoxyphenyl) ethyl]cyclohexanol hydrochloride |
| SI1954669T1 (sl) * | 2005-12-01 | 2016-01-29 | Auspex Pharmaceuticals, Inc. | Substituirani fenetilamini s serotoninergično in / ali noradrenalinsko aktivnostjo |
| DK2125698T3 (en) * | 2007-03-15 | 2016-11-07 | Auspex Pharmaceuticals Inc | Deuterated d9-VENLAFAXINE |
| CN101279926A (zh) * | 2008-05-22 | 2008-10-08 | 杭州盛美医药科技开发有限公司 | 盐酸文拉法辛晶型FormⅠ的制备方法 |
| BR112015005894B1 (pt) | 2012-09-18 | 2022-03-29 | Auspex Pharmaceuticals, Inc | Composto, composição farmacêutica, método para tratar um distúrbio mediado por vmat2 e formulação farmacêutica de liberação prolongada |
| TWI665190B (zh) | 2013-11-15 | 2019-07-11 | 阿克比治療有限公司 | ｛［５－（３－氯苯基）－３－羥基吡啶－２－羰基］胺基｝乙酸之固體型式，其組合物及用途 |
| CN114796209A (zh) | 2015-03-06 | 2022-07-29 | 奥斯拜客斯制药有限公司 | 氘代丁苯那嗪或包含氘代丁苯那嗪的组合物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL63968A (en) * | 1980-10-01 | 1985-10-31 | Glaxo Group Ltd | Form 2 ranitidine hydrochloride,its preparation and pharmaceutical compositions containing it |
| US4535186A (en) * | 1983-04-19 | 1985-08-13 | American Home Products Corporation | 2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives |
| US4611078A (en) * | 1983-10-26 | 1986-09-09 | American Home Products Corporation | Substituted phenylacetonitriles |
| US6197828B1 (en) * | 1998-12-01 | 2001-03-06 | Sepracor, Inc. | Derivatives of (+)-venlafaxine and methods of preparing and using the same |
| CN1620420A (zh) * | 2000-10-19 | 2005-05-25 | 特瓦制药工业有限公司 | 结晶文拉法辛碱和新的文拉法辛盐酸盐多晶型物及其制备方法 |
| CA2426393C (en) | 2000-10-31 | 2012-05-29 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of venlafaxine hydrochloride |
| AU2001235970A1 (en) | 2000-12-07 | 2002-06-18 | Dr. Reddy's Research Foundation | Novel crystalline polymorphic forms of venlafaxine hydrochloride and a process for their preparation |
| DE60136263D1 (de) * | 2001-04-10 | 2008-12-04 | Alembic Ltd | Zwischenprodukt zur Herstellung von 1-Ä2-Dimethylamino-1-(4-methoxyphenyl)-ethylÜ-cyclohexanol |
| CA2467593A1 (en) * | 2001-12-05 | 2003-06-19 | Wyeth | Novel crystalline polymorph of venlafaxine hydrochloride and methods for the preparation thereof |
| WO2003050074A1 (en) * | 2001-12-13 | 2003-06-19 | Cadila Healthcare Limited | Manufacture of venlafaxine hydrochloride and crystalline polymorphs thereof |
-
2001
- 2001-11-30 US US10/000,428 patent/US20020183553A1/en not_active Abandoned
-
2002
- 2002-11-20 PL PL02374273A patent/PL374273A1/xx not_active Application Discontinuation
- 2002-11-20 WO PCT/US2002/037268 patent/WO2003048082A2/en active Search and Examination
- 2002-11-20 KR KR10-2004-7008012A patent/KR20040068163A/ko not_active Application Discontinuation
- 2002-11-20 ZA ZA200404080A patent/ZA200404080B/en unknown
- 2002-11-20 JP JP2003549277A patent/JP2005511668A/ja active Pending
- 2002-11-20 CN CNA028276485A patent/CN1617848A/zh active Pending
- 2002-11-20 CA CA002468728A patent/CA2468728A1/en not_active Abandoned
- 2002-11-20 EP EP02791279A patent/EP1474379A4/en not_active Withdrawn
- 2002-11-20 CN CNA2007101970607A patent/CN101219962A/zh active Pending
- 2002-11-20 HU HU0700037A patent/HUP0700037A2/hu unknown
- 2002-11-20 MX MXPA04005193A patent/MXPA04005193A/es active IP Right Grant
- 2002-11-20 AU AU2002365874A patent/AU2002365874A1/en not_active Abandoned
- 2002-11-20 IL IL16217102A patent/IL162171A0/xx unknown
-
2004
- 2004-05-27 IS IS7289A patent/IS7289A/is unknown
- 2004-06-08 US US10/863,958 patent/US20040220278A1/en not_active Abandoned
- 2004-06-17 HR HR20040565A patent/HRP20040565A2/xx not_active Application Discontinuation
- 2004-06-29 NO NO20042732A patent/NO20042732L/no not_active Application Discontinuation
- 2004-10-07 US US10/961,337 patent/US6924393B2/en not_active Expired - Fee Related
-
2008
- 2008-03-13 US US12/075,875 patent/US20080167498A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1474379A2 (en) | 2004-11-10 |
| KR20040068163A (ko) | 2004-07-30 |
| NO20042732L (no) | 2004-06-29 |
| HRP20040565A2 (en) | 2005-08-31 |
| US6924393B2 (en) | 2005-08-02 |
| CN1617848A (zh) | 2005-05-18 |
| IS7289A (is) | 2004-05-27 |
| US20040220278A1 (en) | 2004-11-04 |
| EP1474379A4 (en) | 2006-06-07 |
| WO2003048082A2 (en) | 2003-06-12 |
| IL162171A0 (en) | 2005-11-20 |
| US20020183553A1 (en) | 2002-12-05 |
| HUP0700037A2 (en) | 2007-05-02 |
| JP2005511668A (ja) | 2005-04-28 |
| US20050049304A1 (en) | 2005-03-03 |
| AU2002365874A1 (en) | 2003-06-17 |
| WO2003048082A3 (en) | 2004-08-26 |
| CN101219962A (zh) | 2008-07-16 |
| CA2468728A1 (en) | 2003-06-12 |
| MXPA04005193A (es) | 2005-02-22 |
| PL374273A1 (en) | 2005-10-03 |
| US20080167498A1 (en) | 2008-07-10 |
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