TWI260315B - Polymorphic forms of sertraline hydrochloride - Google Patents
Polymorphic forms of sertraline hydrochloride Download PDFInfo
- Publication number
- TWI260315B TWI260315B TW089120975A TW89120975A TWI260315B TW I260315 B TWI260315 B TW I260315B TW 089120975 A TW089120975 A TW 089120975A TW 89120975 A TW89120975 A TW 89120975A TW I260315 B TWI260315 B TW I260315B
- Authority
- TW
- Taiwan
- Prior art keywords
- hydrochloride
- solution
- shichalin
- polymorphic form
- polymorphic
- Prior art date
Links
- GLQPTZAAUROJMO-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)benzaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C=O)C=C1 GLQPTZAAUROJMO-UHFFFAOYSA-N 0.000 title abstract 5
- 229960003660 sertraline hydrochloride Drugs 0.000 title abstract 5
- 238000002360 preparation method Methods 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 86
- 239000000243 solution Substances 0.000 claims description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 20
- 239000013078 crystal Substances 0.000 claims description 19
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 18
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 18
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 44
- 239000012453 solvate Substances 0.000 abstract description 36
- 238000010521 absorption reaction Methods 0.000 abstract description 8
- 238000004090 dissolution Methods 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- 238000000634 powder X-ray diffraction Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000000725 suspension Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000001069 Raman spectroscopy Methods 0.000 description 10
- 238000001237 Raman spectrum Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000004847 absorption spectroscopy Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 238000002083 X-ray spectrum Methods 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 206010013663 drug dependence Diseases 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 206010036596 premature ejaculation Diseases 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 208000011117 substance-related disease Diseases 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- 101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910001347 Stellite Inorganic materials 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 1
- 229960005164 acesulfame Drugs 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940125709 anorectic agent Drugs 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- AHICWQREWHDHHF-UHFFFAOYSA-N chromium;cobalt;iron;manganese;methane;molybdenum;nickel;silicon;tungsten Chemical compound C.[Si].[Cr].[Mn].[Fe].[Co].[Ni].[Mo].[W] AHICWQREWHDHHF-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 101150089829 csc-1 gene Proteins 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- BLFQGGGGFNSJKA-XHXSRVRCSA-N sertraline hydrochloride Chemical class Cl.C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 BLFQGGGGFNSJKA-XHXSRVRCSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
- C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99810981 | 1999-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI260315B true TWI260315B (en) | 2006-08-21 |
Family
ID=8243113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089120975A TWI260315B (en) | 1999-10-29 | 2000-10-07 | Polymorphic forms of sertraline hydrochloride |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US6872853B1 (enExample) |
| EP (1) | EP1224160B1 (enExample) |
| JP (1) | JP2003513062A (enExample) |
| CN (1) | CN1384816A (enExample) |
| AR (1) | AR026293A1 (enExample) |
| AT (1) | ATE409684T1 (enExample) |
| AU (1) | AU1386301A (enExample) |
| CA (1) | CA2387135A1 (enExample) |
| DE (1) | DE60040406D1 (enExample) |
| HU (1) | HUP0203559A3 (enExample) |
| IL (2) | IL149050A0 (enExample) |
| MX (1) | MXPA02004255A (enExample) |
| MY (1) | MY141509A (enExample) |
| TR (1) | TR200201146T2 (enExample) |
| TW (1) | TWI260315B (enExample) |
| WO (1) | WO2001032601A1 (enExample) |
| ZA (1) | ZA200203254B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1632472A1 (en) * | 1998-11-27 | 2006-03-08 | Teva Pharmaceutical Industries Ltd | Sertraline hydrochloride polymorphs |
| US6500987B1 (en) * | 1998-11-27 | 2002-12-31 | Teva Pharmaceutical Industries Ltd. | Sertraline hydrochloride polymorphs |
| DE69929462T2 (de) * | 1998-11-27 | 2006-09-07 | Teva Pharmaceutical Industries Ltd. | Sertralin hydrochlorid form |
| US6495721B1 (en) | 1999-08-09 | 2002-12-17 | Teva Pharmaceutical Industries Ltd. | Sertraline hydrochloride Form II and methods for the preparation thereof |
| US7442838B2 (en) * | 1999-10-29 | 2008-10-28 | Ciba Specialty Chemicals Corp. | Polymorphic forms of sertraline hydrochloride |
| US20050119351A1 (en) * | 1999-10-29 | 2005-06-02 | Van Der Schaaf Paul A. | Polymorphic forms of sertraline hydrochloride |
| WO2001045692A1 (en) * | 1999-12-21 | 2001-06-28 | Teva Pharmaceutical Industries Ltd. | Novel sertraline hydrochloride polymorphs, processes for preparing them, compositions containing them and methods of using them |
| EP1772144A3 (en) * | 1999-12-21 | 2007-08-15 | Teva Pharmaceutical Industries Ltd | Novel sertraline hydrochloride polymorphs, processes for preparing them, compositions containing them and methods of using them |
| IN192343B (enExample) * | 2000-05-26 | 2004-04-10 | Ranbaxy Lab Ltd | |
| CA2448279A1 (en) | 2001-05-31 | 2002-12-05 | Orion Corporation Fermion | Process for preparing sertraline hydrochloride polymorphic form ii |
| WO2003093217A1 (en) * | 2002-04-29 | 2003-11-13 | Teva Pharmaceutical Industries Ltd. | Process for preparation of polymorphic form ii of sertraline hydrochloride, pharmaceutical formulations and methods of administration thereof |
| MXPA04011375A (es) * | 2002-06-27 | 2005-02-14 | Interdigital Tech Corp | Controlador de red de radio para intercambio de informacion de equipo. |
| WO2005000786A1 (en) | 2003-05-23 | 2005-01-06 | Transform Pharmaceuticals, Inc. | Sertraline compositions |
| US7893300B2 (en) | 2003-11-04 | 2011-02-22 | Cipla Limited | Process for the preparation of polymorphs of selective serotonin reuptake inhibitor |
| WO2005075467A2 (en) * | 2004-02-06 | 2005-08-18 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of zolmitriptan |
| WO2007008317A2 (en) * | 2005-06-09 | 2007-01-18 | Teva Pharmaceutical Industries Ltd. | Process for preparation of sertraline hydrochloride form i |
| US7518019B2 (en) | 2006-06-01 | 2009-04-14 | Hetero Drugs Limited | Processes for preparing sertraline hydrochloride crystalline forms |
| CA2594198A1 (en) * | 2007-07-20 | 2009-01-20 | Apotex Pharmachem Inc. | A novel process for the preparation of sertraline hydrochloride form ii |
| US9186642B2 (en) | 2010-04-28 | 2015-11-17 | The Procter & Gamble Company | Delivery particle |
| US9993793B2 (en) | 2010-04-28 | 2018-06-12 | The Procter & Gamble Company | Delivery particles |
| CN103458871B (zh) | 2011-04-07 | 2015-05-13 | 宝洁公司 | 具有增强的聚丙烯酸酯微胶囊的沉积的调理剂组合物 |
| WO2012138710A2 (en) | 2011-04-07 | 2012-10-11 | The Procter & Gamble Company | Personal cleansing compositions with increased deposition of polyacrylate microcapsules |
| WO2012138696A2 (en) | 2011-04-07 | 2012-10-11 | The Procter & Gamble Company | Shampoo compositions with increased deposition of polyacrylate microcapsules |
| CN105061217A (zh) * | 2015-06-30 | 2015-11-18 | 徐静 | 枸橼酸舍曲林的2种晶型及其制备方法 |
| CA3194468A1 (en) | 2020-10-16 | 2022-04-21 | Johan Smets | Consumer product compositions comprising a population of encapsulates |
| MX2023004232A (es) | 2020-10-16 | 2023-04-21 | Procter & Gamble | Composiciones de productos de consumo con al menos dos poblaciones de encapsulados. |
| US12486478B2 (en) | 2020-10-16 | 2025-12-02 | The Procter & Gamble Company | Consumer products comprising delivery particles with high core:wall ratios |
| CN112552188B (zh) * | 2020-12-17 | 2023-07-28 | 山西仟源医药集团股份有限公司 | 盐酸舍曲林晶型i的制备方法 |
| CN113588626B (zh) * | 2021-08-24 | 2024-05-24 | 上海师范大学 | 一种苯丙氨酸对映体的拉曼光谱检测方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4536518A (en) | 1979-11-01 | 1985-08-20 | Pfizer Inc. | Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
| US5082970A (en) | 1991-03-06 | 1992-01-21 | Pfizer Inc. | Process for recycling amine isomer |
| GB9114947D0 (en) | 1991-07-11 | 1991-08-28 | Pfizer Ltd | Process for preparing sertraline |
| US5248699A (en) | 1992-08-13 | 1993-09-28 | Pfizer Inc. | Sertraline polymorph |
| US5734083A (en) | 1996-05-17 | 1998-03-31 | Torcan Chemical Ltd. | Sertraline polymorph |
| HU222341B1 (hu) | 1996-12-18 | 2003-06-28 | Richter Gedeon Vegyészeti Gyár Rt. | Eljárás sertralin előállítására és az eljárásban alkalmazott intermedier |
| DE69713353D1 (de) * | 1997-12-11 | 2002-07-18 | Torcan Chemical Ltd | Sertralin-Polymorph mit verbesserter Wasserlöslichkeit |
| CA2323629A1 (en) | 1998-03-18 | 1999-09-23 | Ciba Specialty Chemicals Holding Inc. | Process for the cis-selective catalytic hydrogenation of cyclohexylidenamines |
| JP2000026378A (ja) | 1998-07-03 | 2000-01-25 | Sumika Fine Chemicals Co Ltd | 塩酸セルトラリンの製法 |
| DE69929462T2 (de) | 1998-11-27 | 2006-09-07 | Teva Pharmaceutical Industries Ltd. | Sertralin hydrochlorid form |
| US6500987B1 (en) | 1998-11-27 | 2002-12-31 | Teva Pharmaceutical Industries Ltd. | Sertraline hydrochloride polymorphs |
| US6495721B1 (en) | 1999-08-09 | 2002-12-17 | Teva Pharmaceutical Industries Ltd. | Sertraline hydrochloride Form II and methods for the preparation thereof |
| WO2001045692A1 (en) | 1999-12-21 | 2001-06-28 | Teva Pharmaceutical Industries Ltd. | Novel sertraline hydrochloride polymorphs, processes for preparing them, compositions containing them and methods of using them |
-
2000
- 2000-10-07 TW TW089120975A patent/TWI260315B/zh not_active IP Right Cessation
- 2000-10-20 MY MYPI20004969A patent/MY141509A/en unknown
- 2000-10-23 JP JP2001534755A patent/JP2003513062A/ja not_active Withdrawn
- 2000-10-23 CN CN00815052A patent/CN1384816A/zh active Pending
- 2000-10-23 HU HU0203559A patent/HUP0203559A3/hu unknown
- 2000-10-23 DE DE60040406T patent/DE60040406D1/de not_active Expired - Fee Related
- 2000-10-23 US US10/111,947 patent/US6872853B1/en not_active Expired - Fee Related
- 2000-10-23 EP EP00975896A patent/EP1224160B1/en not_active Expired - Lifetime
- 2000-10-23 IL IL14905000A patent/IL149050A0/xx active IP Right Grant
- 2000-10-23 AU AU13863/01A patent/AU1386301A/en not_active Abandoned
- 2000-10-23 WO PCT/EP2000/010416 patent/WO2001032601A1/en not_active Ceased
- 2000-10-23 AT AT00975896T patent/ATE409684T1/de not_active IP Right Cessation
- 2000-10-23 CA CA002387135A patent/CA2387135A1/en not_active Abandoned
- 2000-10-23 MX MXPA02004255A patent/MXPA02004255A/es active IP Right Grant
- 2000-10-23 TR TR2002/01146T patent/TR200201146T2/xx unknown
- 2000-10-27 AR ARP000105711A patent/AR026293A1/es not_active Application Discontinuation
-
2002
- 2002-04-09 IL IL149050A patent/IL149050A/en not_active IP Right Cessation
- 2002-04-24 ZA ZA200203254A patent/ZA200203254B/xx unknown
-
2003
- 2003-12-15 US US10/736,195 patent/US6939992B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE409684T1 (de) | 2008-10-15 |
| MY141509A (en) | 2010-05-14 |
| ZA200203254B (en) | 2003-07-22 |
| AU1386301A (en) | 2001-05-14 |
| IL149050A0 (en) | 2002-11-10 |
| MXPA02004255A (es) | 2002-10-17 |
| EP1224160A1 (en) | 2002-07-24 |
| US20040132828A1 (en) | 2004-07-08 |
| CN1384816A (zh) | 2002-12-11 |
| HUP0203559A2 (hu) | 2003-03-28 |
| AR026293A1 (es) | 2003-02-05 |
| US6939992B2 (en) | 2005-09-06 |
| WO2001032601A1 (en) | 2001-05-10 |
| US6872853B1 (en) | 2005-03-29 |
| JP2003513062A (ja) | 2003-04-08 |
| DE60040406D1 (de) | 2008-11-13 |
| EP1224160B1 (en) | 2008-10-01 |
| IL149050A (en) | 2007-03-08 |
| HUP0203559A3 (en) | 2008-01-28 |
| TR200201146T2 (tr) | 2004-12-21 |
| CA2387135A1 (en) | 2001-05-10 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |