CA2527127A1 - Process for the preparation of anhydrous eletriptan hemisulphate - Google Patents
Process for the preparation of anhydrous eletriptan hemisulphate Download PDFInfo
- Publication number
- CA2527127A1 CA2527127A1 CA002527127A CA2527127A CA2527127A1 CA 2527127 A1 CA2527127 A1 CA 2527127A1 CA 002527127 A CA002527127 A CA 002527127A CA 2527127 A CA2527127 A CA 2527127A CA 2527127 A1 CA2527127 A1 CA 2527127A1
- Authority
- CA
- Canada
- Prior art keywords
- volume
- eletriptan
- hours
- theta
- water content
- 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
- 229960002472 eletriptan Drugs 0.000 title claims abstract description 74
- OTLDLQZJRFYOJR-LJQANCHMSA-N eletriptan Chemical compound CN1CCC[C@@H]1CC1=CN=C2[C]1C=C(CCS(=O)(=O)C=1C=CC=CC=1)C=C2 OTLDLQZJRFYOJR-LJQANCHMSA-N 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 115
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 58
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 26
- 235000011149 sulphuric acid Nutrition 0.000 claims description 26
- 239000001117 sulphuric acid Substances 0.000 claims description 26
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 21
- 238000010992 reflux Methods 0.000 claims description 17
- 238000010533 azeotropic distillation Methods 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 13
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 9
- 239000002002 slurry Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 235000019439 ethyl acetate Nutrition 0.000 description 37
- 238000000113 differential scanning calorimetry Methods 0.000 description 29
- 239000000203 mixture Substances 0.000 description 21
- 239000000725 suspension Substances 0.000 description 21
- 238000001914 filtration Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 239000002244 precipitate Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 15
- 238000001816 cooling Methods 0.000 description 11
- 239000012453 solvate Substances 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 230000011514 reflex Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 101710180995 Endonuclease 1 Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001144 powder X-ray diffraction data Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- -1 alkyl acetate Chemical compound 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012776 robust process Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000005406 washing Methods 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0312478.1 | 2003-05-30 | ||
| GBGB0312478.1A GB0312478D0 (en) | 2003-05-30 | 2003-05-30 | Improved process |
| PCT/IB2004/001694 WO2004106327A1 (en) | 2003-05-30 | 2004-05-18 | Process for the preparation of anhydrous eleptritan hemisulphate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2527127A1 true CA2527127A1 (en) | 2004-12-09 |
Family
ID=9959072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002527127A Abandoned CA2527127A1 (en) | 2003-05-30 | 2004-05-18 | Process for the preparation of anhydrous eletriptan hemisulphate |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1633739A1 (pt) |
| JP (1) | JP2006528968A (pt) |
| AR (1) | AR044463A1 (pt) |
| BR (1) | BRPI0410841A (pt) |
| CA (1) | CA2527127A1 (pt) |
| CL (1) | CL2004001132A1 (pt) |
| GB (1) | GB0312478D0 (pt) |
| MX (1) | MXPA05012838A (pt) |
| TW (1) | TWI290923B (pt) |
| WO (1) | WO2004106327A1 (pt) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUT64326A (en) * | 1990-10-15 | 1993-12-28 | Pfizer | Process for production indole derivatives and pharmaceutical preparations containing these compounds |
| GB9417310D0 (en) * | 1994-08-27 | 1994-10-19 | Pfizer Ltd | Therapeutic agents |
| ATE206921T1 (de) * | 1997-07-03 | 2001-11-15 | Pfizer | Eletriptanhemisulfat und kaffein enthaltende pharmazeutische zusammenstellungen |
| GB9922963D0 (en) * | 1999-09-28 | 1999-12-01 | Pfizer Ltd | Polymorphic salt |
-
2003
- 2003-05-30 GB GBGB0312478.1A patent/GB0312478D0/en not_active Ceased
-
2004
- 2004-05-18 MX MXPA05012838A patent/MXPA05012838A/es unknown
- 2004-05-18 WO PCT/IB2004/001694 patent/WO2004106327A1/en active Application Filing
- 2004-05-18 BR BRPI0410841-8A patent/BRPI0410841A/pt not_active IP Right Cessation
- 2004-05-18 CA CA002527127A patent/CA2527127A1/en not_active Abandoned
- 2004-05-18 JP JP2006530682A patent/JP2006528968A/ja active Pending
- 2004-05-18 EP EP04733602A patent/EP1633739A1/en not_active Withdrawn
- 2004-05-19 CL CL200401132A patent/CL2004001132A1/es unknown
- 2004-05-25 TW TW093114789A patent/TWI290923B/zh not_active IP Right Cessation
- 2004-05-28 AR ARP040101864A patent/AR044463A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1633739A1 (en) | 2006-03-15 |
| BRPI0410841A (pt) | 2006-06-27 |
| TW200427683A (en) | 2004-12-16 |
| MXPA05012838A (es) | 2006-02-13 |
| CL2004001132A1 (es) | 2005-03-18 |
| AR044463A1 (es) | 2005-09-14 |
| TWI290923B (en) | 2007-12-11 |
| GB0312478D0 (en) | 2003-07-09 |
| WO2004106327A1 (en) | 2004-12-09 |
| JP2006528968A (ja) | 2006-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |