CN1496350A - 制备纯二水合昂丹司琼盐酸盐的改进方法 - Google Patents
制备纯二水合昂丹司琼盐酸盐的改进方法 Download PDFInfo
- Publication number
- CN1496350A CN1496350A CNA028062019A CN02806201A CN1496350A CN 1496350 A CN1496350 A CN 1496350A CN A028062019 A CNA028062019 A CN A028062019A CN 02806201 A CN02806201 A CN 02806201A CN 1496350 A CN1496350 A CN 1496350A
- Authority
- CN
- China
- Prior art keywords
- ondansetron
- methyl
- hydrochloride dihydrate
- solution
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229960005343 ondansetron Drugs 0.000 title claims abstract description 83
- FELGMEQIXOGIFQ-UHFFFAOYSA-N Ondansetron Chemical compound CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 78
- FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 claims abstract description 41
- 238000001953 recrystallisation Methods 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 37
- -1 dimethylamino-methyl-carbazole ketone Chemical class 0.000 claims description 36
- 238000001556 precipitation Methods 0.000 claims description 28
- 239000003513 alkali Substances 0.000 claims description 25
- 238000002425 crystallisation Methods 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 12
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 claims description 11
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical class CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 9
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 9
- 229920002866 paraformaldehyde Polymers 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 239000012670 alkaline solution Substances 0.000 claims description 5
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000021962 pH elevation Effects 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- VHXLDRBDRZYEQE-UHFFFAOYSA-N 3-(dimethylamino)-2-methylcarbazol-1-one Chemical compound C1=CC=C2C3=CC(N(C)C)=C(C)C(=O)C3=NC2=C1 VHXLDRBDRZYEQE-UHFFFAOYSA-N 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- VOOZDTJWSBLXAN-UHFFFAOYSA-N N,N,1-trimethyl-9H-carbazol-2-amine Chemical compound CN(C)C1=C(C=2NC3=CC=CC=C3C2C=C1)C VOOZDTJWSBLXAN-UHFFFAOYSA-N 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 230000003474 anti-emetic effect Effects 0.000 description 2
- 239000002111 antiemetic agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 1
- 102100024954 5-hydroxytryptamine receptor 3A Human genes 0.000 description 1
- 101710138027 5-hydroxytryptamine receptor 3A Proteins 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010062519 Poor quality sleep Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002460 anti-migrenic effect Effects 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Otolaryngology (AREA)
- Anesthesiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26105201P | 2001-01-11 | 2001-01-11 | |
| US60/261,052 | 2001-01-11 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2006101667179A Division CN101045704A (zh) | 2001-01-11 | 2002-01-11 | 制备纯二水合昂丹司琼盐酸盐的改进方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1496350A true CN1496350A (zh) | 2004-05-12 |
Family
ID=22991757
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2006101667179A Pending CN101045704A (zh) | 2001-01-11 | 2002-01-11 | 制备纯二水合昂丹司琼盐酸盐的改进方法 |
| CNA028062019A Pending CN1496350A (zh) | 2001-01-11 | 2002-01-11 | 制备纯二水合昂丹司琼盐酸盐的改进方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2006101667179A Pending CN101045704A (zh) | 2001-01-11 | 2002-01-11 | 制备纯二水合昂丹司琼盐酸盐的改进方法 |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP1355881A4 (is) |
| JP (1) | JP2004526692A (is) |
| KR (3) | KR20060113792A (is) |
| CN (2) | CN101045704A (is) |
| AU (1) | AU2002236753B2 (is) |
| CA (1) | CA2433720A1 (is) |
| CZ (1) | CZ20032090A3 (is) |
| DE (1) | DE02703115T1 (is) |
| ES (1) | ES2219201T1 (is) |
| HR (1) | HRP20030631A2 (is) |
| HU (1) | HUP0400767A2 (is) |
| IL (1) | IL156835A0 (is) |
| IS (1) | IS6869A (is) |
| MX (1) | MXPA03006215A (is) |
| NO (1) | NO20033147L (is) |
| PL (1) | PL368837A1 (is) |
| SK (1) | SK9892003A3 (is) |
| TR (1) | TR200401460T3 (is) |
| WO (1) | WO2002055492A2 (is) |
| YU (1) | YU56103A (is) |
| ZA (1) | ZA200305338B (is) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7098345B2 (en) | 2002-04-29 | 2006-08-29 | TEVA Gyógyszergyár Zárkörüen Müködö Részvénytársaság | Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-YL)methyl]-4H-carbazol-4-one |
| HU225885B1 (en) * | 2002-10-17 | 2007-11-28 | Richter Gedeon Nyrt | Process for producing ondansetron hydrochlorid dihydrate of high purity |
| FI6164U1 (fi) * | 2003-01-09 | 2004-03-15 | Synthon Bv | Ondansetronmuotoja |
| GB2398071B (en) * | 2003-01-24 | 2006-06-07 | Synthon Bv | Process for making ondansetron and intermediate thereof |
| US7696356B2 (en) | 2004-08-17 | 2010-04-13 | Taro Pharmaceutical Industries Limited | Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one and ondansetron therefrom |
| US7547791B2 (en) * | 2004-10-26 | 2009-06-16 | Ipca Laboratories Ltd. | One-pot process for the preparation of antiemetic agent, 1,2,3,9-tetrahydro-9-methyl-3[(2-methyl)-1H-imidazole-1-yl)methyl]-4H-carbazol-4-O |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4695578A (en) * | 1984-01-25 | 1987-09-22 | Glaxo Group Limited | 1,2,3,9-tetrahydro-3-imidazol-1-ylmethyl-4H-carbazol-4-ones, composition containing them, and method of using them to treat neuronal 5HT function disturbances |
| GB8630071D0 (en) * | 1986-12-17 | 1987-01-28 | Glaxo Group Ltd | Medicaments |
| CN1498216A (zh) * | 2000-10-30 | 2004-05-19 | ������ҩ��ҵ����˾ | 新的奥丹西隆盐酸盐晶体和溶剂化物及其制备方法 |
-
2002
- 2002-01-11 KR KR1020067020069A patent/KR20060113792A/ko not_active Application Discontinuation
- 2002-01-11 DE DE02703115T patent/DE02703115T1/de active Pending
- 2002-01-11 KR KR10-2003-7009221A patent/KR20030068583A/ko active IP Right Grant
- 2002-01-11 ES ES02703115T patent/ES2219201T1/es active Pending
- 2002-01-11 AU AU2002236753A patent/AU2002236753B2/en not_active Expired - Fee Related
- 2002-01-11 MX MXPA03006215A patent/MXPA03006215A/es unknown
- 2002-01-11 CZ CZ20032090A patent/CZ20032090A3/cs unknown
- 2002-01-11 CN CNA2006101667179A patent/CN101045704A/zh active Pending
- 2002-01-11 ZA ZA200305338A patent/ZA200305338B/xx unknown
- 2002-01-11 PL PL02368837A patent/PL368837A1/xx not_active Application Discontinuation
- 2002-01-11 IL IL15683502A patent/IL156835A0/xx unknown
- 2002-01-11 YU YU56103A patent/YU56103A/sh unknown
- 2002-01-11 JP JP2002556165A patent/JP2004526692A/ja active Pending
- 2002-01-11 HU HU0400767A patent/HUP0400767A2/hu unknown
- 2002-01-11 KR KR1020077010146A patent/KR20070054749A/ko not_active Application Discontinuation
- 2002-01-11 TR TR2004/01460T patent/TR200401460T3/xx unknown
- 2002-01-11 CN CNA028062019A patent/CN1496350A/zh active Pending
- 2002-01-11 SK SK989-2003A patent/SK9892003A3/sk not_active Application Discontinuation
- 2002-01-11 CA CA002433720A patent/CA2433720A1/en not_active Abandoned
- 2002-01-11 WO PCT/US2002/000853 patent/WO2002055492A2/en active Application Filing
- 2002-01-11 EP EP02703115A patent/EP1355881A4/en not_active Withdrawn
-
2003
- 2003-07-08 IS IS6869A patent/IS6869A/is unknown
- 2003-07-09 NO NO20033147A patent/NO20033147L/no not_active Application Discontinuation
- 2003-08-06 HR HR20030631A patent/HRP20030631A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004526692A (ja) | 2004-09-02 |
| TR200401460T3 (is) | 2004-08-23 |
| SK9892003A3 (en) | 2004-05-04 |
| CZ20032090A3 (cs) | 2004-08-18 |
| EP1355881A2 (en) | 2003-10-29 |
| MXPA03006215A (es) | 2005-02-17 |
| KR20070054749A (ko) | 2007-05-29 |
| IS6869A (is) | 2003-07-08 |
| DE02703115T1 (de) | 2004-10-21 |
| KR20060113792A (ko) | 2006-11-02 |
| CN101045704A (zh) | 2007-10-03 |
| YU56103A (sh) | 2006-05-25 |
| KR20030068583A (ko) | 2003-08-21 |
| HRP20030631A2 (en) | 2005-06-30 |
| NO20033147D0 (no) | 2003-07-09 |
| ZA200305338B (en) | 2004-07-12 |
| PL368837A1 (en) | 2005-04-04 |
| WO2002055492A2 (en) | 2002-07-18 |
| HUP0400767A2 (hu) | 2004-07-28 |
| WO2002055492A3 (en) | 2003-02-13 |
| IL156835A0 (en) | 2004-02-08 |
| CA2433720A1 (en) | 2002-07-18 |
| ES2219201T1 (es) | 2004-12-01 |
| AU2002236753B2 (en) | 2007-06-28 |
| NO20033147L (no) | 2003-09-02 |
| EP1355881A4 (en) | 2004-03-31 |
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