DE69900007T2 - Paroxetinmethansulfonat - Google Patents
ParoxetinmethansulfonatInfo
- Publication number
- DE69900007T2 DE69900007T2 DE69900007T DE69900007T DE69900007T2 DE 69900007 T2 DE69900007 T2 DE 69900007T2 DE 69900007 T DE69900007 T DE 69900007T DE 69900007 T DE69900007 T DE 69900007T DE 69900007 T2 DE69900007 T2 DE 69900007T2
- Authority
- DE
- Germany
- Prior art keywords
- paroxetine
- solution
- paroxetine methanesulfonate
- solvent
- methanesulfonate
- 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.)
- Revoked
Links
- SHIJTGJXUHTGGZ-RVXRQPKJSA-N (3s,4r)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidin-1-ium;methanesulfonate Chemical compound CS(O)(=O)=O.C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 SHIJTGJXUHTGGZ-RVXRQPKJSA-N 0.000 title claims description 151
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 159
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 106
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 84
- 229960002296 paroxetine Drugs 0.000 claims description 84
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 77
- 239000002904 solvent Substances 0.000 claims description 72
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 51
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- 239000013078 crystal Substances 0.000 claims description 41
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- 230000008025 crystallization Effects 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- -1 organic acid salt Chemical class 0.000 claims description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 31
- 230000008569 process Effects 0.000 claims description 24
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 31
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 6
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- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium;phosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 4
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- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- DHUXGFHEJUYKNX-UHFFFAOYSA-N acetonitrile;methanesulfonic acid Chemical compound CC#N.CS(O)(=O)=O DHUXGFHEJUYKNX-UHFFFAOYSA-N 0.000 description 3
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- 238000004458 analytical method Methods 0.000 description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229960005183 paroxetine hydrochloride Drugs 0.000 description 3
- AEIUZSKXSWGSRU-QXGDPHCHSA-N paroxetine maleate Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AEIUZSKXSWGSRU-QXGDPHCHSA-N 0.000 description 3
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- 125000004122 cyclic group Chemical group 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
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- 235000019359 magnesium stearate Nutrition 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical group CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
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- XHNUMAXRQGMHKZ-CVDCTZTESA-N phenyl (3s,4r)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine-1-carboxylate Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CN(C(=O)OC=2C=CC=CC=2)CC1 XHNUMAXRQGMHKZ-CVDCTZTESA-N 0.000 description 2
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004179 indigotine Substances 0.000 description 1
- 235000012738 indigotine Nutrition 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 238000002356 laser light scattering Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
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- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
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- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- OCAAZRFBJBEVPS-UHFFFAOYSA-N prop-2-enyl carbamate Chemical compound NC(=O)OCC=C OCAAZRFBJBEVPS-UHFFFAOYSA-N 0.000 description 1
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
- 238000001374 small-angle light scattering Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
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- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- WGHIJTFVCGNFTJ-UHFFFAOYSA-N tert-butyl 2-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine-1-carboxylate Chemical compound C1C(COC=2C=C3OCOC3=CC=2)N(C(=O)OC(C)(C)C)CCC1C1=CC=C(F)C=C1 WGHIJTFVCGNFTJ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 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
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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Classifications
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4525—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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)
- Neurology (AREA)
- Neurosurgery (AREA)
- Inorganic Chemistry (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9814316.7A GB9814316D0 (en) | 1998-07-02 | 1998-07-02 | Novel compounds |
| GBGB9821732.6A GB9821732D0 (en) | 1998-10-06 | 1998-10-06 | Novel compound |
| GBGB9902935.7A GB9902935D0 (en) | 1999-02-10 | 1999-02-10 | Novel compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69900007D1 DE69900007D1 (de) | 2000-09-07 |
| DE69900007T2 true DE69900007T2 (de) | 2001-06-07 |
Family
ID=27269380
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69900007T Revoked DE69900007T2 (de) | 1998-07-02 | 1999-04-23 | Paroxetinmethansulfonat |
| DE19918588A Ceased DE19918588A1 (de) | 1998-07-02 | 1999-04-23 | Piperidinverbindung |
| DE69911774T Expired - Fee Related DE69911774T2 (de) | 1998-07-02 | 1999-04-23 | Paroxetinmethansulfonat-acetonitrilsolvat 1:1 |
| DE29907248U Expired - Lifetime DE29907248U1 (de) | 1998-07-02 | 1999-04-23 | Neue Verbindung |
| DE60000003T Revoked DE60000003T2 (de) | 1998-07-02 | 2000-04-10 | Paroxetinmethansulfonat |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19918588A Ceased DE19918588A1 (de) | 1998-07-02 | 1999-04-23 | Piperidinverbindung |
| DE69911774T Expired - Fee Related DE69911774T2 (de) | 1998-07-02 | 1999-04-23 | Paroxetinmethansulfonat-acetonitrilsolvat 1:1 |
| DE29907248U Expired - Lifetime DE29907248U1 (de) | 1998-07-02 | 1999-04-23 | Neue Verbindung |
| DE60000003T Revoked DE60000003T2 (de) | 1998-07-02 | 2000-04-10 | Paroxetinmethansulfonat |
Country Status (34)
| Country | Link |
|---|---|
| US (4) | US6063927A (ref) |
| EP (5) | EP1020463A1 (ref) |
| JP (1) | JP2002519422A (ref) |
| KR (1) | KR20010053336A (ref) |
| CN (1) | CN1127502C (ref) |
| AR (2) | AR011759A1 (ref) |
| AT (4) | ATE251155T1 (ref) |
| AU (4) | AU713131B3 (ref) |
| BE (3) | BE1011664A6 (ref) |
| BR (1) | BR9911682A (ref) |
| CA (1) | CA2269999A1 (ref) |
| CH (1) | CH689805A8 (ref) |
| DE (5) | DE69900007T2 (ref) |
| DK (7) | DK199900176U3 (ref) |
| ES (4) | ES2158778B1 (ref) |
| FI (2) | FI4209U1 (ref) |
| FR (2) | FR2780728B1 (ref) |
| GB (5) | GB2352395B (ref) |
| GR (3) | GR990100140A (ref) |
| HU (1) | HUP0102334A3 (ref) |
| IE (5) | IES20000893A2 (ref) |
| IL (1) | IL140628A (ref) |
| IT (1) | IT1312540B1 (ref) |
| LU (1) | LU90388B1 (ref) |
| NL (4) | NL1011874C1 (ref) |
| NO (1) | NO319030B1 (ref) |
| NZ (1) | NZ509180A (ref) |
| PL (1) | PL345214A1 (ref) |
| PT (4) | PT1089996E (ref) |
| SE (1) | SE9901462A0 (ref) |
| SI (3) | SI1020464T1 (ref) |
| SK (1) | SK20262000A3 (ref) |
| TR (1) | TR200100054T2 (ref) |
| WO (1) | WO2000001694A1 (ref) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5998401A (en) * | 1995-02-28 | 1999-12-07 | Eli Lilly And Company | Naphthyl compounds, intermediates, compositions, and methods |
| AU734548B2 (en) * | 1997-02-27 | 2001-06-14 | Ajinomoto Co., Inc. | Apparatus and method for crystallization |
| EE03970B1 (et) * | 1997-06-10 | 2003-02-17 | Synthon B.V. | 4-fenüülpiperidiinühend, selle valmistamine ja kasutamine ning seda sisaldav ravim |
| CH689805A8 (fr) * | 1998-07-02 | 2000-02-29 | Smithkline Beecham Plc | Méthanesulfonate de paroxétine, procédé pour sa préparation et compositions pharmaceutiques le contenant. |
| US20040028582A1 (en) * | 1999-03-10 | 2004-02-12 | Smithkline Beecham Corporation | Crystallization process for producing fine crystal products |
| USPP12225P2 (en) | 1999-06-01 | 2001-11-27 | Florfis Ag | Geranium plant named ‘Fislamda’ |
| WO2000078290A2 (en) * | 1999-06-22 | 2000-12-28 | Smithkline Beecham P.L.C. | Pharmaceutical composition comprising a salt of paroxetine |
| ES2159260B1 (es) * | 1999-06-22 | 2002-05-01 | Smithkline Beechan Plc | Nueva composicion de metanosulfonato de paroxetina |
| GB0003232D0 (en) * | 2000-02-11 | 2000-04-05 | Smithkline Beecham Plc | Novel composition |
| US6306435B1 (en) | 2000-06-26 | 2001-10-23 | Yung Shin Pharmaceutical Industrial Co. Ltd. | Oral pharmaceutical preparation embedded in an oily matrix and methods of making the same |
| GB0015981D0 (en) * | 2000-06-29 | 2000-08-23 | Glaxo Group Ltd | Novel process for preparing crystalline particles |
| NZ523902A (en) * | 2000-08-28 | 2004-05-28 | Synthon Bv | Paroxetine compositions and processes for making the same |
| DE20100529U1 (de) * | 2001-01-11 | 2001-05-10 | Synthon Bv | Pharmazeutische Tablette umfassend Paroxetinmesylat |
| NL1017421C2 (nl) | 2001-02-21 | 2002-01-15 | Synthon Bv | Werkwijze voor het vervaardigen van paroxetine. |
| EP1412350A1 (en) * | 2001-08-02 | 2004-04-28 | Spurcourt Limited | Paroxetine isethionate salt, process of preparation and use in the treatment of depression |
| AU2003217676B2 (en) | 2002-02-22 | 2009-06-11 | Takeda Pharmaceutical Company Limited | Active agent delivery systems and methods for protecting and administering active agents |
| US20050266082A1 (en) * | 2004-05-26 | 2005-12-01 | Patel Satishkumar A | Preparation of stable paroxetine HC1 ER tablets using a melt granulation process |
| US20060063737A1 (en) * | 2004-08-18 | 2006-03-23 | Holmdahl Lisa K | Liquid paroxetine compositions |
| US20060039975A1 (en) * | 2004-08-20 | 2006-02-23 | Zalman Vilkov | Paroxetine formulations |
| KR100672184B1 (ko) | 2004-09-21 | 2007-01-19 | 주식회사종근당 | 파록세틴의 콜린산 또는 콜린산 유도체 염 |
| MX2007012362A (es) * | 2005-04-07 | 2007-11-07 | Xy Inc | Sistema acondicionador de trayectoria de flujo. |
| WO2007058998A2 (en) * | 2005-11-14 | 2007-05-24 | Auspex Pharmaceuticals, Inc. | Substituted phenylpiperidines with serotoninergic activity and enhanced therapeutic properties |
| WO2007063384A2 (en) * | 2005-12-01 | 2007-06-07 | Pfizer Products Inc. | Pyrimidine derivatives for the treatment of abnormal cell growth |
| US20080033050A1 (en) | 2006-08-04 | 2008-02-07 | Richards Patricia Allison Tewe | Method of treating thermoregulatory disfunction with paroxetine |
| KR20090118110A (ko) * | 2007-03-09 | 2009-11-17 | 노파르티스 아게 | 3-(1ｈ-인돌-3-일)-4-[2-(4-메틸-피페라진-1-일)-퀴나졸린-4-일]-피롤-2,5-디온의 염 |
| US20100249166A1 (en) | 2007-09-19 | 2010-09-30 | Xy, Inc. | Differential evaporation potentiated disinfectant system |
| US8119688B2 (en) * | 2007-09-19 | 2012-02-21 | Xy, Llc | Differential evaporation potentiated disinfectant system |
| FR2926552B1 (fr) * | 2008-01-23 | 2010-03-26 | Biocodex | Procede de preparation de particules de stiripentol ayant une granulometrie definie |
| CN103961333B (zh) * | 2014-05-07 | 2020-02-21 | 浙江华海药业股份有限公司 | 甲磺酸帕罗西汀胶囊及其制备方法 |
| CN104523645A (zh) * | 2014-11-20 | 2015-04-22 | 美吉斯制药（厦门）有限公司 | 甲磺酸帕罗西汀片芯及其包衣片的制备方法 |
| US11111373B2 (en) | 2018-12-05 | 2021-09-07 | Chi Mei Corporation | Polymethacrylate composition and optical device made therefrom, and display apparatus |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE99678C (ref) * | ||||
| GB1422263A (en) * | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
| US4585777A (en) * | 1984-02-07 | 1986-04-29 | A/S Ferrosan | (-)-Trans-4-(4-fluorophenyl)-3-(4-methoxyphenoxy)methylpiperidine for potentiating 5-HT |
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1999
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2001
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