HRP20020773A2 - Novel process for preparing (+)-cis-sertraline - Google Patents
Novel process for preparing (+)-cis-sertraline Download PDFInfo
- Publication number
- HRP20020773A2 HRP20020773A2 HR20020773A HRP20020773A HRP20020773A2 HR P20020773 A2 HRP20020773 A2 HR P20020773A2 HR 20020773 A HR20020773 A HR 20020773A HR P20020773 A HRP20020773 A HR P20020773A HR P20020773 A2 HRP20020773 A2 HR P20020773A2
- Authority
- HR
- Croatia
- Prior art keywords
- sertraline
- cis
- base
- palladium
- hydrochloride
- Prior art date
Links
- 229960002073 sertraline Drugs 0.000 title claims description 86
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 86
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 84
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 65
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical class C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 claims description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 52
- 239000002585 base Substances 0.000 claims description 48
- 229960003660 sertraline hydrochloride Drugs 0.000 claims description 44
- 239000000243 solution Substances 0.000 claims description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 229910052763 palladium Inorganic materials 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 23
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 22
- 239000006227 byproduct Substances 0.000 claims description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 20
- 239000003960 organic solvent Substances 0.000 claims description 20
- 239000002244 precipitate Substances 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 230000001376 precipitating effect Effects 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 229910002804 graphite Inorganic materials 0.000 claims description 11
- 239000010439 graphite Substances 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
- 238000001556 precipitation Methods 0.000 claims description 8
- 229910019020 PtO2 Inorganic materials 0.000 claims description 7
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 238000002955 isolation Methods 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 239000003637 basic solution Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- BLFQGGGGFNSJKA-XHXSRVRCSA-N sertraline hydrochloride Chemical compound Cl.C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 BLFQGGGGFNSJKA-XHXSRVRCSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 239000003245 coal Substances 0.000 claims 1
- 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 description 13
- 229960002510 mandelic acid Drugs 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 9
- JGMBHJNMQVKDMW-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C2=CC=CC=C2C(=O)CC1 JGMBHJNMQVKDMW-UHFFFAOYSA-N 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 238000000746 purification Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002262 Schiff base Substances 0.000 description 5
- 150000004753 Schiff bases Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 3
- 238000004296 chiral HPLC Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MIOPJNTWMNEORI-XVKPBYJWSA-N (R)-camphorsulfonic acid Chemical compound C1C[C@]2(CS(O)(=O)=O)C(=O)C[C@H]1C2(C)C MIOPJNTWMNEORI-XVKPBYJWSA-N 0.000 description 1
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 101150084411 crn1 gene Proteins 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229940020965 zoloft Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/86—Separation
- C07C209/88—Separation of optical isomers
-
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18935500P | 2000-03-14 | 2000-03-14 | |
| PCT/US2001/008090 WO2001068566A1 (en) | 2000-03-14 | 2001-03-14 | Novel process for preparing (+)-cis-sertraline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20020773A2 true HRP20020773A2 (en) | 2005-02-28 |
Family
ID=22696967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020773A HRP20020773A2 (en) | 2000-03-14 | 2002-09-25 | Novel process for preparing (+)-cis-sertraline |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US6552227B2 (hu) |
| EP (1) | EP1268369A4 (hu) |
| JP (1) | JP2003527359A (hu) |
| KR (3) | KR20070002101A (hu) |
| CN (1) | CN1232481C (hu) |
| AU (2) | AU2001243634B2 (hu) |
| CA (1) | CA2402656A1 (hu) |
| CZ (1) | CZ20023269A3 (hu) |
| HR (1) | HRP20020773A2 (hu) |
| HU (1) | HUP0300160A3 (hu) |
| IL (1) | IL151691A0 (hu) |
| PL (1) | PL357262A1 (hu) |
| SK (1) | SK14212002A3 (hu) |
| WO (1) | WO2001068566A1 (hu) |
| ZA (1) | ZA200207225B (hu) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6552227B2 (en) * | 2000-03-14 | 2003-04-22 | Teva Pharmaceutical Industries Ltd. | Process for preparing (+)-cis-sertraline |
| EP1401800A1 (en) * | 2001-06-15 | 2004-03-31 | Orion Corporation Fermion | A novel process for the preparation of (is-cis) -4-(3, 4-dichlorophenyl) -1, 2, 3, 4 - tetrahydro-n-methyl-1-naphthalenamine |
| US6723878B2 (en) | 2001-06-15 | 2004-04-20 | Orion Corporation Fermion | Method for preparing sertraline |
| US6897340B2 (en) * | 2002-04-29 | 2005-05-24 | Teva Pharmaceutical Industries Ltd. | Processes for preparation of polymorphic form II of sertraline hydrochloride |
| EP1583734A2 (en) * | 2003-04-14 | 2005-10-12 | Teva Pharmaceutical Industries Limited | Hydrogenation of imine intermediates of sertraline with catalysts |
| CA2537804A1 (en) * | 2003-09-05 | 2005-03-17 | Teva Pharmaceutical Industries Ltd | A recycling process for preparing sertraline |
| US8868772B2 (en) | 2004-04-30 | 2014-10-21 | Echostar Technologies L.L.C. | Apparatus, system, and method for adaptive-rate shifting of streaming content |
| WO2005121074A2 (en) * | 2004-06-09 | 2005-12-22 | Ranbaxy Laboratories Limited | Processes for the preparation of sertraline hydrochloride |
| US7345201B2 (en) * | 2005-02-23 | 2008-03-18 | Teva Pharmaceutical Industries, Ltd. | Processes for preparing sertraline |
| GB0507090D0 (en) * | 2005-04-07 | 2005-05-11 | Sandoz Ag | Process for preparing polymorphic form ll of sertraline hydrochloride |
| WO2007119247A2 (en) * | 2006-04-17 | 2007-10-25 | Unichem Laboratories Limited | Improved manufacturing procedure for the preparation of polymorphic form ii of cis-(1s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthleneamine hydrochloride (sertraline hydrochloride) |
| KR101340270B1 (ko) | 2011-11-10 | 2013-12-10 | 보령제약 주식회사 | (+)-시스-서트랄린의 선택적인 제조방법 |
| CN103524354A (zh) * | 2013-10-23 | 2014-01-22 | 山东鲁药制药有限公司 | 一种盐酸舍曲林的制备方法 |
| CN111763150B (zh) * | 2019-12-27 | 2024-03-08 | 上虞京新药业有限公司 | 一种手性盐酸舍曲林的制备方法 |
Family Cites Families (15)
| 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 |
| 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 |
| HU222341B1 (hu) * | 1996-12-18 | 2003-06-28 | Richter Gedeon Vegyészeti Gyár Rt. | Eljárás sertralin előállítására és az eljárásban alkalmazott intermedier |
| IN191358B (hu) * | 1998-01-16 | 2003-11-29 | Pfizer Prod Inc | |
| JP2002506844A (ja) * | 1998-03-18 | 2002-03-05 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | シクロヘキシリデンアミンのｃｉｓ−選択的接触水素化方法 |
| HU226424B1 (en) * | 1998-05-05 | 2008-12-29 | Egis Gyogyszergyar Nyrt | Process for producing enantiomer mixture for preparation of sertraline |
| JP2000026378A (ja) * | 1998-07-03 | 2000-01-25 | Sumika Fine Chemicals Co Ltd | 塩酸セルトラリンの製法 |
| WO2000025598A1 (en) | 1998-11-03 | 2000-05-11 | Dandy A/S | Sucrose fatty acid esters for use as increased release of active ingredients |
| US6500987B1 (en) | 1998-11-27 | 2002-12-31 | Teva Pharmaceutical Industries Ltd. | Sertraline hydrochloride polymorphs |
| YU32700A (sh) | 1999-06-09 | 2002-03-18 | Pfizer Products Inc. | Postupak za dobijanje sertralina iz hiralnog tetralona |
| US6495721B1 (en) | 1999-08-09 | 2002-12-17 | Teva Pharmaceutical Industries Ltd. | Sertraline hydrochloride Form II and methods for the preparation thereof |
| IN185109B (hu) | 1999-09-01 | 2000-11-18 | Torrent Pharmaceuticals Ltd | |
| SK8872002A3 (en) | 1999-12-21 | 2002-12-03 | Teva Pharma | Novel sertraline hydrochloride polymorphs, processes for preparing them, compositions containing them and methods of using them |
| US6552227B2 (en) * | 2000-03-14 | 2003-04-22 | Teva Pharmaceutical Industries Ltd. | Process for preparing (+)-cis-sertraline |
-
2001
- 2001-03-14 US US09/805,829 patent/US6552227B2/en not_active Expired - Lifetime
- 2001-03-14 SK SK1421-2002A patent/SK14212002A3/sk not_active Application Discontinuation
- 2001-03-14 PL PL01357262A patent/PL357262A1/xx not_active Application Discontinuation
- 2001-03-14 WO PCT/US2001/008090 patent/WO2001068566A1/en active Application Filing
- 2001-03-14 KR KR1020067025010A patent/KR20070002101A/ko not_active Application Discontinuation
- 2001-03-14 JP JP2001567667A patent/JP2003527359A/ja active Pending
- 2001-03-14 AU AU2001243634A patent/AU2001243634B2/en not_active Ceased
- 2001-03-14 CA CA002402656A patent/CA2402656A1/en not_active Abandoned
- 2001-03-14 IL IL15169101A patent/IL151691A0/xx unknown
- 2001-03-14 HU HU0300160A patent/HUP0300160A3/hu unknown
- 2001-03-14 KR KR1020027011986A patent/KR100704590B1/ko not_active IP Right Cessation
- 2001-03-14 AU AU4363401A patent/AU4363401A/xx active Pending
- 2001-03-14 EP EP01916635A patent/EP1268369A4/en not_active Withdrawn
- 2001-03-14 CN CNB018094031A patent/CN1232481C/zh not_active Expired - Fee Related
- 2001-03-14 CZ CZ20023269A patent/CZ20023269A3/cs unknown
- 2001-03-14 KR KR1020067025012A patent/KR20070002102A/ko not_active Application Discontinuation
-
2002
- 2002-09-09 ZA ZA200207225A patent/ZA200207225B/en unknown
- 2002-09-25 HR HR20020773A patent/HRP20020773A2/hr not_active Application Discontinuation
-
2003
- 2003-02-12 US US10/365,795 patent/US6809221B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001068566A1 (en) | 2001-09-20 |
| EP1268369A4 (en) | 2005-09-21 |
| KR20070002102A (ko) | 2007-01-04 |
| US20020019570A1 (en) | 2002-02-14 |
| HUP0300160A2 (hu) | 2003-06-28 |
| PL357262A1 (en) | 2004-07-26 |
| KR20070002101A (ko) | 2007-01-04 |
| US6552227B2 (en) | 2003-04-22 |
| SK14212002A3 (sk) | 2003-07-01 |
| CN1429188A (zh) | 2003-07-09 |
| US20030166970A1 (en) | 2003-09-04 |
| JP2003527359A (ja) | 2003-09-16 |
| KR20020089394A (ko) | 2002-11-29 |
| CZ20023269A3 (cs) | 2003-09-17 |
| AU4363401A (en) | 2001-09-24 |
| EP1268369A1 (en) | 2003-01-02 |
| HUP0300160A3 (en) | 2005-07-28 |
| AU2001243634B2 (en) | 2006-05-25 |
| US6809221B2 (en) | 2004-10-26 |
| KR100704590B1 (ko) | 2007-04-10 |
| CA2402656A1 (en) | 2001-09-20 |
| ZA200207225B (en) | 2003-09-09 |
| IL151691A0 (en) | 2003-04-10 |
| CN1232481C (zh) | 2005-12-21 |
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