CA2433720A1 - An improved process for preparing pure ondansetron hydrochloride dihydrate - Google Patents
An improved process for preparing pure ondansetron hydrochloride dihydrate Download PDFInfo
- Publication number
- CA2433720A1 CA2433720A1 CA002433720A CA2433720A CA2433720A1 CA 2433720 A1 CA2433720 A1 CA 2433720A1 CA 002433720 A CA002433720 A CA 002433720A CA 2433720 A CA2433720 A CA 2433720A CA 2433720 A1 CA2433720 A1 CA 2433720A1
- Authority
- CA
- Canada
- Prior art keywords
- process according
- solution
- ondansetron
- methyl
- carbazolone
- 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.)
- Abandoned
Links
- 229960005343 ondansetron Drugs 0.000 title claims abstract description 55
- 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 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 62
- 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 36
- 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 claims abstract description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 41
- 239000002244 precipitate Substances 0.000 claims description 29
- MKBLHFILKIKSQM-UHFFFAOYSA-N 9-methyl-3-[(2-methyl-1h-imidazol-3-ium-3-yl)methyl]-2,3-dihydro-1h-carbazol-4-one;chloride Chemical compound Cl.CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 MKBLHFILKIKSQM-UHFFFAOYSA-N 0.000 claims description 23
- 229960000770 ondansetron hydrochloride Drugs 0.000 claims description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- XSLBAHVOKAHAJM-UHFFFAOYSA-N 2-methylcarbazol-1-one Chemical compound C1=CC=C2C3=CC=C(C)C(=O)C3=NC2=C1 XSLBAHVOKAHAJM-UHFFFAOYSA-N 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 11
- 230000008025 crystallization Effects 0.000 claims description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 10
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 claims description 9
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 claims description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 9
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 8
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 8
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 8
- 229920002866 paraformaldehyde Polymers 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- AGQJDIDJKSFVTC-UHFFFAOYSA-N 9-methyl-3-methylidene-1,2-dihydrocarbazol-4-one Chemical compound C12=CC=CC=C2N(C)C2=C1C(=O)C(=C)CC2 AGQJDIDJKSFVTC-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 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
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KOYOTMNMRPZRKM-UHFFFAOYSA-N 3-amino-2,4,5-trimethylcarbazol-1-one Chemical compound C1=CC(C)=C2C3=C(C)C(N)=C(C)C(=O)C3=NC2=C1 KOYOTMNMRPZRKM-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000002460 anti-migrenic effect Effects 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000012970 cakes Nutrition 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
- 239000013078 crystal Substances 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000021463 dry cake Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000009877 rendering Methods 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
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Otolaryngology (AREA)
- Anesthesiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26105201P | 2001-01-11 | 2001-01-11 | |
| US60/261,052 | 2001-01-11 | ||
| PCT/US2002/000853 WO2002055492A2 (en) | 2001-01-11 | 2002-01-11 | An improved process for preparing pure ondansetron hydrochloride dihydrate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2433720A1 true CA2433720A1 (en) | 2002-07-18 |
Family
ID=22991757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002433720A Abandoned CA2433720A1 (en) | 2001-01-11 | 2002-01-11 | An improved process for preparing pure ondansetron hydrochloride dihydrate |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP1355881A4 (cs) |
| JP (1) | JP2004526692A (cs) |
| KR (3) | KR20070054749A (cs) |
| CN (2) | CN1496350A (cs) |
| AU (1) | AU2002236753B2 (cs) |
| CA (1) | CA2433720A1 (cs) |
| CZ (1) | CZ20032090A3 (cs) |
| DE (1) | DE02703115T1 (cs) |
| ES (1) | ES2219201T1 (cs) |
| HR (1) | HRP20030631A2 (cs) |
| HU (1) | HUP0400767A2 (cs) |
| IL (1) | IL156835A0 (cs) |
| IS (1) | IS6869A (cs) |
| MX (1) | MXPA03006215A (cs) |
| NO (1) | NO20033147L (cs) |
| PL (1) | PL368837A1 (cs) |
| SK (1) | SK9892003A3 (cs) |
| TR (1) | TR200401460T3 (cs) |
| WO (1) | WO2002055492A2 (cs) |
| YU (1) | YU56103A (cs) |
| ZA (1) | ZA200305338B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2483566A1 (en) | 2002-04-29 | 2003-11-13 | Biogal Gyogyszergyar Rt. | 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 |
| WO2006046253A1 (en) * | 2004-10-26 | 2006-05-04 | Ipca Laboratories Limited | A 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 |
| SK6182003A3 (en) * | 2000-10-30 | 2004-03-02 | Teva Pharma | Crystalline and solvated forms of ondansetrone hydrochloride and preparation thereof |
-
2002
- 2002-01-11 SK SK989-2003A patent/SK9892003A3/sk not_active Application Discontinuation
- 2002-01-11 CN CNA028062019A patent/CN1496350A/zh active Pending
- 2002-01-11 YU YU56103A patent/YU56103A/sh unknown
- 2002-01-11 TR TR2004/01460T patent/TR200401460T3/xx unknown
- 2002-01-11 ZA ZA200305338A patent/ZA200305338B/xx unknown
- 2002-01-11 HR HR20030631A patent/HRP20030631A2/hr not_active Application Discontinuation
- 2002-01-11 CN CNA2006101667179A patent/CN101045704A/zh active Pending
- 2002-01-11 IL IL15683502A patent/IL156835A0/xx unknown
- 2002-01-11 DE DE02703115T patent/DE02703115T1/de active Pending
- 2002-01-11 CZ CZ20032090A patent/CZ20032090A3/cs unknown
- 2002-01-11 AU AU2002236753A patent/AU2002236753B2/en not_active Expired - Fee Related
- 2002-01-11 HU HU0400767A patent/HUP0400767A2/hu unknown
- 2002-01-11 WO PCT/US2002/000853 patent/WO2002055492A2/en not_active Ceased
- 2002-01-11 KR KR1020077010146A patent/KR20070054749A/ko not_active Ceased
- 2002-01-11 ES ES02703115T patent/ES2219201T1/es active Pending
- 2002-01-11 JP JP2002556165A patent/JP2004526692A/ja active Pending
- 2002-01-11 MX MXPA03006215A patent/MXPA03006215A/es unknown
- 2002-01-11 PL PL02368837A patent/PL368837A1/xx not_active Application Discontinuation
- 2002-01-11 EP EP02703115A patent/EP1355881A4/en not_active Withdrawn
- 2002-01-11 KR KR10-2003-7009221A patent/KR20030068583A/ko not_active Abandoned
- 2002-01-11 CA CA002433720A patent/CA2433720A1/en not_active Abandoned
- 2002-01-11 KR KR1020067020069A patent/KR20060113792A/ko not_active Ceased
-
2003
- 2003-07-08 IS IS6869A patent/IS6869A/is unknown
- 2003-07-09 NO NO20033147A patent/NO20033147L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| YU56103A (sh) | 2006-05-25 |
| WO2002055492A3 (en) | 2003-02-13 |
| ZA200305338B (en) | 2004-07-12 |
| EP1355881A2 (en) | 2003-10-29 |
| ES2219201T1 (es) | 2004-12-01 |
| IS6869A (is) | 2003-07-08 |
| AU2002236753B2 (en) | 2007-06-28 |
| TR200401460T3 (cs) | 2004-08-23 |
| EP1355881A4 (en) | 2004-03-31 |
| HUP0400767A2 (hu) | 2004-07-28 |
| CN101045704A (zh) | 2007-10-03 |
| SK9892003A3 (en) | 2004-05-04 |
| CN1496350A (zh) | 2004-05-12 |
| KR20030068583A (ko) | 2003-08-21 |
| KR20070054749A (ko) | 2007-05-29 |
| JP2004526692A (ja) | 2004-09-02 |
| IL156835A0 (en) | 2004-02-08 |
| PL368837A1 (en) | 2005-04-04 |
| CZ20032090A3 (cs) | 2004-08-18 |
| KR20060113792A (ko) | 2006-11-02 |
| WO2002055492A2 (en) | 2002-07-18 |
| NO20033147L (no) | 2003-09-02 |
| MXPA03006215A (es) | 2005-02-17 |
| NO20033147D0 (no) | 2003-07-09 |
| HRP20030631A2 (en) | 2005-06-30 |
| DE02703115T1 (de) | 2004-10-21 |
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