HRP20041070A2 - Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1h-imidazol-1-yl)methyl)-4h-carbazol-4-one - Google Patents
Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1h-imidazol-1-yl)methyl)-4h-carbazol-4-one Download PDFInfo
- Publication number
- HRP20041070A2 HRP20041070A2 HR20041070A HRP20041070A HRP20041070A2 HR P20041070 A2 HRP20041070 A2 HR P20041070A2 HR 20041070 A HR20041070 A HR 20041070A HR P20041070 A HRP20041070 A HR P20041070A HR P20041070 A2 HRP20041070 A2 HR P20041070A2
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- tetrahydro
- carbazol
- imidazol
- solvent system
- Prior art date
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- 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 description 27
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 77
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 82
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
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- 238000002360 preparation method Methods 0.000 claims description 19
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- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 6
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- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 229940072018 zofran Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic 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
-
- 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
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37632302P | 2002-04-29 | 2002-04-29 | |
| PCT/US2003/013221 WO2003093281A1 (fr) | 2002-04-29 | 2003-04-29 | Methode de preparation de 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1h-imidazol-1-yl)methyl]-4h-carbazol-4-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20041070A2 true HRP20041070A2 (en) | 2005-02-28 |
Family
ID=29401332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20041070A HRP20041070A2 (en) | 2002-04-29 | 2004-11-16 | Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1h-imidazol-1-yl)methyl)-4h-carbazol-4-one |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US7098345B2 (fr) |
| EP (1) | EP1499623B1 (fr) |
| JP (1) | JP2005529142A (fr) |
| KR (1) | KR20040104654A (fr) |
| CN (1) | CN1665823A (fr) |
| AT (1) | ATE364611T1 (fr) |
| AU (1) | AU2003223764A1 (fr) |
| CA (1) | CA2483566A1 (fr) |
| DE (1) | DE60314400T2 (fr) |
| DK (1) | DK1499623T3 (fr) |
| ES (1) | ES2288606T3 (fr) |
| HR (1) | HRP20041070A2 (fr) |
| IL (1) | IL164904A0 (fr) |
| MX (1) | MXPA04010846A (fr) |
| NO (1) | NO20045192L (fr) |
| PL (1) | PL373191A1 (fr) |
| PT (1) | PT1499623E (fr) |
| WO (1) | WO2003093281A1 (fr) |
| ZA (1) | ZA200408934B (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE01991193T1 (de) * | 2000-10-30 | 2004-07-08 | Teva Pharmaceutical Industries Ltd. | Neue kristall- und solvatformen von ondansetronhydrochlorid und verfahren zu deren herstellung |
| CN1665803A (zh) * | 2002-04-30 | 2005-09-07 | 特瓦药厂有限公司 | 新晶形的昂丹司琼及其制备方法、含有该新晶形的药物组合物以及用其治疗恶心的方法 |
| US20050131045A1 (en) * | 2002-04-30 | 2005-06-16 | Judith Aronhime | Novel crystal forms of ondansetron, processes for their preparation, pharmaceutical, compositions containing the novel forms and methods for treating nausea using them |
| 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 |
| EP1828141A4 (fr) * | 2004-10-26 | 2009-04-01 | Ipca Lab Ltd | Procede monotope de preparation de l'agent antiemetique 1,2,3,9-tetrahydro-9-methyl-3[(2-methyl-1h-imidazole-1-yl)methyl]-4h-carbazol-4-one |
Family Cites Families (22)
| 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 |
| HU193592B (en) | 1984-01-25 | 1987-11-30 | Glaxo Group Ltd | Process for producing tetrahydro-carbazolone derivatives |
| EP0405617A3 (en) | 1985-03-14 | 1992-11-25 | Beecham Group P.L.C. | Medicaments for the treatment of anxiety |
| GB8518741D0 (en) | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Process |
| GB8518742D0 (en) | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Process |
| GB8518743D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Heterocyclic compounds |
| GB8518745D0 (en) | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Heterocyclic compounds |
| US4859662A (en) | 1986-11-28 | 1989-08-22 | Glaxo Group Limited | Tetrahydro-imidazolylmethylcarbazolones and analogs thereof for treating 5-HT function disturbances |
| GB8630071D0 (en) | 1986-12-17 | 1987-01-28 | Glaxo Group Ltd | Medicaments |
| GB8816187D0 (en) * | 1988-07-07 | 1988-08-10 | Glaxo Group Ltd | Medicaments |
| US5344658A (en) | 1989-06-28 | 1994-09-06 | Glaxo Group Limited | Process and composition using ondansetron |
| GB8914804D0 (en) | 1989-06-28 | 1989-08-16 | Glaxo Group Ltd | Process |
| EP0591434A4 (en) | 1991-06-26 | 1994-09-14 | Sepracor Inc | Method and compositions for treating emesis, nausea and other disorders using optically pure r(+) ondansetron |
| CA2106642C (fr) | 1992-10-14 | 2005-08-16 | Peter Bod | Derives de carbazolone et procede d'obtention |
| GB9423588D0 (en) | 1994-11-22 | 1995-01-11 | Glaxo Wellcome Inc | Compositions |
| GB9423511D0 (en) | 1994-11-22 | 1995-01-11 | Glaxo Wellcome Inc | Compositions |
| CN1045437C (zh) | 1994-12-29 | 1999-10-06 | 中国科学院上海有机化学研究所 | 恩丹西酮及其生理盐的合成 |
| DE01991193T1 (de) | 2000-10-30 | 2004-07-08 | Teva Pharmaceutical Industries Ltd. | Neue kristall- und solvatformen von ondansetronhydrochlorid und verfahren zu deren herstellung |
| EP1207160A1 (fr) | 2000-11-20 | 2002-05-22 | Hanmi Pharm. Co., Ltd. | Procédé de préparation de la 1,2,3,9-tétrahydro-9-méthyl-3-((2-méthyl-1H-imidazol-1-yl)-méthyl)-4H-carbazol-4-one |
| SK9892003A3 (en) | 2001-01-11 | 2004-05-04 | Teva Pharma | An improved process for preparing pure ondansetron hydrochloride dihydrate |
| AU2002251329A1 (en) | 2002-04-25 | 2003-11-10 | Generics (Uk) Limited | Novel crystalline forms of celecoxib and other compounds |
| CN1665803A (zh) | 2002-04-30 | 2005-09-07 | 特瓦药厂有限公司 | 新晶形的昂丹司琼及其制备方法、含有该新晶形的药物组合物以及用其治疗恶心的方法 |
-
2003
- 2003-04-29 PT PT03719968T patent/PT1499623E/pt unknown
- 2003-04-29 CA CA002483566A patent/CA2483566A1/fr not_active Abandoned
- 2003-04-29 US US10/425,450 patent/US7098345B2/en not_active Expired - Fee Related
- 2003-04-29 AT AT03719968T patent/ATE364611T1/de not_active IP Right Cessation
- 2003-04-29 PL PL03373191A patent/PL373191A1/xx not_active Application Discontinuation
- 2003-04-29 EP EP03719968A patent/EP1499623B1/fr not_active Expired - Lifetime
- 2003-04-29 CN CN038154684A patent/CN1665823A/zh active Pending
- 2003-04-29 AU AU2003223764A patent/AU2003223764A1/en not_active Abandoned
- 2003-04-29 DE DE60314400T patent/DE60314400T2/de not_active Expired - Fee Related
- 2003-04-29 MX MXPA04010846A patent/MXPA04010846A/es unknown
- 2003-04-29 KR KR10-2004-7017346A patent/KR20040104654A/ko not_active Application Discontinuation
- 2003-04-29 JP JP2004501420A patent/JP2005529142A/ja active Pending
- 2003-04-29 ES ES03719968T patent/ES2288606T3/es not_active Expired - Lifetime
- 2003-04-29 WO PCT/US2003/013221 patent/WO2003093281A1/fr active IP Right Grant
- 2003-04-29 DK DK03719968T patent/DK1499623T3/da active
-
2004
- 2004-10-28 IL IL16490404A patent/IL164904A0/xx unknown
- 2004-11-04 ZA ZA200408934A patent/ZA200408934B/xx unknown
- 2004-11-16 HR HR20041070A patent/HRP20041070A2/hr not_active Application Discontinuation
- 2004-11-26 NO NO20045192A patent/NO20045192L/no not_active Application Discontinuation
-
2006
- 2006-07-07 US US11/482,486 patent/US20060252942A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US7098345B2 (en) | 2006-08-29 |
| AU2003223764A1 (en) | 2003-11-17 |
| ZA200408934B (en) | 2006-07-26 |
| PL373191A1 (en) | 2005-08-22 |
| CA2483566A1 (fr) | 2003-11-13 |
| ES2288606T3 (es) | 2008-01-16 |
| MXPA04010846A (es) | 2005-01-25 |
| US20060252942A1 (en) | 2006-11-09 |
| NO20045192L (no) | 2005-01-28 |
| US20050020655A1 (en) | 2005-01-27 |
| WO2003093281A1 (fr) | 2003-11-13 |
| DE60314400D1 (de) | 2007-07-26 |
| ATE364611T1 (de) | 2007-07-15 |
| JP2005529142A (ja) | 2005-09-29 |
| DE60314400T2 (de) | 2008-02-07 |
| CN1665823A (zh) | 2005-09-07 |
| DK1499623T3 (da) | 2007-10-08 |
| EP1499623B1 (fr) | 2007-06-13 |
| PT1499623E (pt) | 2007-08-10 |
| IL164904A0 (en) | 2005-12-18 |
| KR20040104654A (ko) | 2004-12-10 |
| EP1499623A1 (fr) | 2005-01-26 |
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