CA2692955A1 - Nouveau procede de preparation de zopiclone et de ses polymorphes - Google Patents
Nouveau procede de preparation de zopiclone et de ses polymorphes Download PDFInfo
- Publication number
- CA2692955A1 CA2692955A1 CA 2692955 CA2692955A CA2692955A1 CA 2692955 A1 CA2692955 A1 CA 2692955A1 CA 2692955 CA2692955 CA 2692955 CA 2692955 A CA2692955 A CA 2692955A CA 2692955 A1 CA2692955 A1 CA 2692955A1
- Authority
- CA
- Canada
- Prior art keywords
- zopiclone
- crystalline
- theta
- solid
- filtering
- 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
- GBBSUAFBMRNDJC-MRXNPFEDSA-N (5R)-zopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-MRXNPFEDSA-N 0.000 title claims abstract description 99
- 229960000820 zopiclone Drugs 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000007787 solid Substances 0.000 claims abstract description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 23
- 238000001914 filtration Methods 0.000 claims abstract description 16
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 239000002002 slurry Substances 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 8
- 239000012044 organic layer Substances 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 230000001376 precipitating effect Effects 0.000 claims abstract 2
- 238000002329 infrared spectrum Methods 0.000 claims description 8
- 238000000862 absorption spectrum Methods 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000932 sedative agent Substances 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 10
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 239000003960 organic solvent Substances 0.000 description 4
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 229940088679 drug related substance Drugs 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000004683 dihydrates Chemical group 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- -1 more preferably Chemical compound 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- FBAIGEMWTOSCRU-UHFFFAOYSA-N 4-methylpiperazine-1-carbonyl chloride Chemical compound CN1CCN(C(Cl)=O)CC1 FBAIGEMWTOSCRU-UHFFFAOYSA-N 0.000 description 1
- FUUXOEKDNNWZTR-UHFFFAOYSA-N 6-(5-chloropyridin-2-yl)-7-hydroxy-7h-pyrrolo[3,4-b]pyrazin-5-one Chemical compound O=C1C2=NC=CN=C2C(O)N1C1=CC=C(Cl)C=N1 FUUXOEKDNNWZTR-UHFFFAOYSA-N 0.000 description 1
- KAZMCIGKULUUMR-UHFFFAOYSA-N 6-methylpyridazin-3-amine Chemical compound CC1=CC=C(N)N=N1 KAZMCIGKULUUMR-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000005554 hypnotics and sedatives Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Anesthesiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2423/MUM/2007 | 2007-12-11 | ||
| IN2423MU2007 | 2007-12-11 | ||
| PCT/IN2008/000829 WO2009087667A2 (fr) | 2007-12-11 | 2008-12-10 | Nouveau procédé de préparation de zopiclone et de ses polymorphes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2692955A1 true CA2692955A1 (fr) | 2009-07-16 |
Family
ID=40602189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2692955 Abandoned CA2692955A1 (fr) | 2007-12-11 | 2008-12-10 | Nouveau procede de preparation de zopiclone et de ses polymorphes |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20100190797A1 (fr) |
| JP (1) | JP2011506427A (fr) |
| KR (1) | KR20100101051A (fr) |
| AU (1) | AU2008346110A1 (fr) |
| CA (1) | CA2692955A1 (fr) |
| WO (1) | WO2009087667A2 (fr) |
| ZA (1) | ZA200909211B (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2772168C (fr) * | 2009-08-27 | 2019-01-08 | Glaxosmithkline Llc | Formes anhydrates d'un derive de pyridine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA04285A (fr) * | 1972-01-07 | 1979-12-31 | Rhone Poulenc Sa | Nouveaux dérivés de la pyrrolo (3,4-b) pyrazine et leur préparation. |
| US7476737B2 (en) * | 2005-09-05 | 2009-01-13 | Dr. Reddy's Laboratories Limited | Eszopiclone process |
| US7786304B2 (en) * | 2006-11-06 | 2010-08-31 | Centaur Pharmaceutical Pvt. Ltd. | Process for the preparation of eszopiclone |
-
2008
- 2008-12-10 AU AU2008346110A patent/AU2008346110A1/en not_active Abandoned
- 2008-12-10 KR KR1020097027213A patent/KR20100101051A/ko not_active Withdrawn
- 2008-12-10 CA CA 2692955 patent/CA2692955A1/fr not_active Abandoned
- 2008-12-10 US US12/664,949 patent/US20100190797A1/en not_active Abandoned
- 2008-12-10 WO PCT/IN2008/000829 patent/WO2009087667A2/fr not_active Ceased
- 2008-12-10 JP JP2010537602A patent/JP2011506427A/ja active Pending
-
2009
- 2009-12-23 ZA ZA200909211A patent/ZA200909211B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2008346110A1 (en) | 2009-07-16 |
| WO2009087667A3 (fr) | 2009-10-15 |
| WO2009087667A2 (fr) | 2009-07-16 |
| ZA200909211B (en) | 2010-09-29 |
| JP2011506427A (ja) | 2011-03-03 |
| KR20100101051A (ko) | 2010-09-16 |
| US20100190797A1 (en) | 2010-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |