EA001190B1 - Дигидратная соль мезилата 5-(2-(4-(1,2-бензизотиазол-3-ил)-1-пиперазинил)этил)-6-хлор-1,3-дигидро-2(1н)-индол-2-она, фармацевтическая композиция и способ лечения психотического расстройства - Google Patents
Дигидратная соль мезилата 5-(2-(4-(1,2-бензизотиазол-3-ил)-1-пиперазинил)этил)-6-хлор-1,3-дигидро-2(1н)-индол-2-она, фармацевтическая композиция и способ лечения психотического расстройства Download PDFInfo
- Publication number
- EA001190B1 EA001190B1 EA199800912A EA199800912A EA001190B1 EA 001190 B1 EA001190 B1 EA 001190B1 EA 199800912 A EA199800912 A EA 199800912A EA 199800912 A EA199800912 A EA 199800912A EA 001190 B1 EA001190 B1 EA 001190B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- piperazinyl
- dihydro
- psychotic disorder
- benzisothiazol
- ethyl
- Prior art date
Links
- 208000028017 Psychotic disease Diseases 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 14
- UAAKJEVCDBPTQS-UHFFFAOYSA-N methanesulfonic acid;dihydrate Chemical class O.O.CS(O)(=O)=O UAAKJEVCDBPTQS-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000000203 mixture Substances 0.000 title description 8
- 239000013078 crystal Substances 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 7
- 241000124008 Mammalia Species 0.000 claims abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
- 238000007911 parenteral administration Methods 0.000 claims abstract description 6
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 5
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 5
- 208000002193 Pain Diseases 0.000 claims abstract description 5
- 230000036506 anxiety Effects 0.000 claims abstract description 5
- 208000035475 disorder Diseases 0.000 claims abstract description 5
- 239000003937 drug carrier Substances 0.000 claims abstract description 5
- 206010027599 migraine Diseases 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 238000010255 intramuscular injection Methods 0.000 claims abstract description 4
- 239000007927 intramuscular injection Substances 0.000 claims abstract description 4
- -1 dihydrate salt Chemical class 0.000 claims description 23
- GXHMMDRXHUIUMN-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O GXHMMDRXHUIUMN-UHFFFAOYSA-N 0.000 claims 1
- WLQZEFFFIUHSJB-UHFFFAOYSA-N ziprasidone mesylate trihydrate Chemical compound O.O.O.CS(O)(=O)=O.C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 WLQZEFFFIUHSJB-UHFFFAOYSA-N 0.000 description 38
- 229960004487 ziprasidone mesylate Drugs 0.000 description 37
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 19
- 239000000725 suspension Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000002441 X-ray diffraction Methods 0.000 description 10
- 229940098779 methanesulfonic acid Drugs 0.000 description 10
- 150000004683 dihydrates Chemical class 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 239000012458 free base Substances 0.000 description 5
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ZCBZSCBNOOIHFP-UHFFFAOYSA-N ziprasidone hydrochloride hydrate Chemical compound [H+].O.[Cl-].C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 ZCBZSCBNOOIHFP-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229960000607 ziprasidone Drugs 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001000 micrograph Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- LKGCPYOBWLSCTK-UHFFFAOYSA-N methanesulfonic acid;trihydrate Chemical compound O.O.O.CS(O)(=O)=O LKGCPYOBWLSCTK-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000008227 sterile water for injection Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 150000004684 trihydrates Chemical class 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000008012 organic excipient Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1675796P | 1996-05-07 | 1996-05-07 | |
| PCT/IB1997/000393 WO1997042191A1 (en) | 1996-05-07 | 1997-04-10 | Mesylate dihydrate salts of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2(1h)-indol-2-one (=ziprasidone), its preparation and its use as dopamine d2 antagonist |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA199800912A1 EA199800912A1 (ru) | 1999-04-29 |
| EA001190B1 true EA001190B1 (ru) | 2000-12-25 |
Family
ID=21778804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA199800912A EA001190B1 (ru) | 1996-05-07 | 1997-04-10 | Дигидратная соль мезилата 5-(2-(4-(1,2-бензизотиазол-3-ил)-1-пиперазинил)этил)-6-хлор-1,3-дигидро-2(1н)-индол-2-она, фармацевтическая композиция и способ лечения психотического расстройства |
Country Status (40)
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HN1996000101A (es) * | 1996-02-28 | 1997-06-26 | Inc Pfizer | Terapia combinada para la osteoporosis |
| UA57734C2 (uk) | 1996-05-07 | 2003-07-15 | Пфайзер Інк. | Комплекси включення арилгетероциклічних солей |
| IL127497A (en) * | 1997-12-18 | 2002-07-25 | Pfizer Prod Inc | Medicinal products containing piperazinyl-heterocyclic compounds for the treatment of psychiatric disorders |
| US20080113025A1 (en) * | 1998-11-02 | 2008-05-15 | Elan Pharma International Limited | Compositions comprising nanoparticulate naproxen and controlled release hydrocodone |
| NZ551012A (en) * | 2000-06-02 | 2008-04-30 | Pfizer Prod Inc | Use of S-methyl-dihydro-ziprasidone administered via either the oral, parenteral (such as subcutaneous, intravenous, intramuscular, intrasternal and infusion techniques), rectal, intranasal or topical routes in doses ranging from 0.5 to 500 mg per day |
| UY27668A1 (es) | 2002-02-20 | 2003-10-31 | Pfizer Prod Inc | Composición de ziprasidona y controles sintéticos |
| US20040048876A1 (en) * | 2002-02-20 | 2004-03-11 | Pfizer Inc. | Ziprasidone composition and synthetic controls |
| AU2004237951A1 (en) | 2003-05-16 | 2004-11-25 | Pfizer Products Inc. | Therapeutic combinations of atypical antipsychotics with GABA modulators, anticonvulsants or benzodiazapines |
| EP1530570A2 (en) * | 2003-06-03 | 2005-05-18 | Teva Pharmaceutical Industries Limited | CRISTALLINE ZIPRASIDONE HCl AND PROCESSES FOR PREPARATION THEREOF |
| EP1628973A2 (en) | 2003-10-24 | 2006-03-01 | Teva Pharmaceutical Industries Ltd. | Processes for preparation of ziprasidone |
| BRPI0510942A (pt) * | 2004-05-11 | 2007-07-17 | Pfizer Prod Inc | combinação de antipsicóticos atìpicos e antagonistas do receptor 5-ht1b |
| CA2467538C (en) | 2004-05-14 | 2010-08-24 | Apotex Pharmachem Inc. | New amorphous ziprasidone hydrochloride (5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2h-indol-2-one hydrochloride) and processes to produce the same |
| CA2471219A1 (en) | 2004-06-14 | 2005-12-14 | Apotex Pharmachem Inc. | Improved preparation of an anhydrate form of 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2h-indol-2-one hydrochloride (ziprasidone hydrochloride) |
| US7777037B2 (en) * | 2004-10-27 | 2010-08-17 | Dr. Reddy's Laboratories Limited | Ziprasidone process |
| CA2587710C (en) * | 2004-11-16 | 2014-10-21 | Elan Pharma International Ltd. | Injectable nanoparticulate olanzapine formulations |
| CA2591670A1 (en) * | 2005-02-11 | 2006-08-17 | Teva Pharmaceutical Industries Ltd. | Process of preparing ziprasidone mesylate |
| WO2006086779A1 (en) * | 2005-02-11 | 2006-08-17 | Teva Pharmaceutical Industries Ltd. | Amorphous ziprasidone mesylate |
| US20080254114A1 (en) * | 2005-03-03 | 2008-10-16 | Elan Corporation Plc | Controlled Release Compositions Comprising Heterocyclic Amide Derivative Nanoparticles |
| ITMI20050346A1 (it) | 2005-03-07 | 2006-09-08 | Dipharma Spa | Forma solida di ziprasidone cloridrato |
| CA2500667C (en) | 2005-03-11 | 2013-01-15 | Apotex Pharmachem Inc. | Preparation of acid addition salts of ziprasidone and intermediates thereof by solid phase-gas phase reactions |
| WO2006098834A2 (en) * | 2005-03-14 | 2006-09-21 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of ziprasidone mesylate |
| WO2006099452A1 (en) * | 2005-03-14 | 2006-09-21 | Teva Pharmaceutical Industries Ltd. | Anhydrous ziprasidone mesylate and a process for its preparation |
| ITMI20052216A1 (it) * | 2005-11-18 | 2007-05-19 | Dipharma Spa | Procedimento per la preparazione di ziprasidone |
| WO2008143960A1 (en) * | 2007-05-18 | 2008-11-27 | Scidose Llc | Ziprasidone formulations |
| WO2009156889A1 (en) * | 2008-06-25 | 2009-12-30 | Pfizer Inc. | Diaryl compounds and uses thereof |
| JP5893616B2 (ja) * | 2010-10-18 | 2016-03-23 | 大日本住友製薬株式会社 | 注射用徐放性製剤 |
| SI23610A (sl) | 2011-01-13 | 2012-07-31 | Diagen@d@o@o | Nove adicijske soli ziprasidona postopek za njihovo pripravo in njihova uporaba v terapiji |
| US20140206667A1 (en) | 2012-11-14 | 2014-07-24 | Michela Gallagher | Methods and compositions for treating schizophrenia |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX173362B (es) * | 1987-03-02 | 1994-02-23 | Pfizer | Compuestos de piperazinil heterociclicos y procedimiento para su preparacion |
| US4831031A (en) * | 1988-01-22 | 1989-05-16 | Pfizer Inc. | Aryl piperazinyl-(C2 or C4) alkylene heterocyclic compounds having neuroleptic activity |
| US5206366A (en) * | 1992-08-26 | 1993-04-27 | Pfizer Inc. | Process for preparing aryl piperazinyl-heterocyclic compounds |
| US5312925A (en) | 1992-09-01 | 1994-05-17 | Pfizer Inc. | Monohydrate of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one-hydrochloride |
| US5359068A (en) | 1993-06-28 | 1994-10-25 | Pfizer Inc. | Processes and intermediates for the preparation of 5-[2-(4-(benzoisothiazol-3-yl)-piperazin-1-yl)ethyl]-6-chloro-1,3-dihydro-indol-2-one |
| CZ289216B6 (cs) | 1996-05-07 | 2001-12-12 | Pfizer Inc. | Trihydrát methansulfonátu 5-(2-(4-(1,2-benzizothiazol-3-yl)-1-piperazinyl)ethyl)-6-chlor-1,3-dihydro-2H-indol-2-onu, farmaceutická kompozice a léčivo na jeho bázi |
-
1997
- 1997-04-01 TW TW086104173A patent/TW491847B/zh not_active IP Right Cessation
- 1997-04-10 UA UA98115905A patent/UA46840C2/uk unknown
- 1997-04-10 WO PCT/IB1997/000393 patent/WO1997042191A1/en not_active Ceased
- 1997-04-10 AU AU21747/97A patent/AU731267B2/en not_active Ceased
- 1997-04-10 EA EA199800912A patent/EA001190B1/ru not_active IP Right Cessation
- 1997-04-10 DK DK97914520T patent/DK0918772T3/da active
- 1997-04-10 AT AT97914520T patent/ATE278689T1/de not_active IP Right Cessation
- 1997-04-10 TR TR1998/02240T patent/TR199802240T2/xx unknown
- 1997-04-10 DE DE69731094T patent/DE69731094T2/de not_active Expired - Lifetime
- 1997-04-10 NZ NZ332218A patent/NZ332218A/en unknown
- 1997-04-10 CZ CZ19983493A patent/CZ289215B6/cs not_active IP Right Cessation
- 1997-04-10 IL IL12659197A patent/IL126591A/en not_active IP Right Cessation
- 1997-04-10 BR BR9709889A patent/BR9709889A/pt not_active Application Discontinuation
- 1997-04-10 JP JP53967297A patent/JP3494659B2/ja not_active Expired - Lifetime
- 1997-04-10 US US09/180,455 patent/US6245765B1/en not_active Expired - Lifetime
- 1997-04-10 PL PL97329884A patent/PL188330B1/pl unknown
- 1997-04-10 CN CN97194244A patent/CN1091769C/zh not_active Expired - Fee Related
- 1997-04-10 CA CA002252898A patent/CA2252898C/en not_active Expired - Lifetime
- 1997-04-10 PT PT97914520T patent/PT918772E/pt unknown
- 1997-04-10 SI SI9730676T patent/SI0918772T1/xx unknown
- 1997-04-10 SK SK1508-98A patent/SK282837B6/sk not_active IP Right Cessation
- 1997-04-10 ES ES97914520T patent/ES2229342T3/es not_active Expired - Lifetime
- 1997-04-10 KR KR1019980708960A patent/KR100333215B1/ko not_active Expired - Fee Related
- 1997-04-10 EP EP97914520A patent/EP0918772B1/en not_active Expired - Lifetime
- 1997-04-29 CO CO97022872A patent/CO4940466A1/es unknown
- 1997-04-29 GT GT199700052A patent/GT199700052A/es unknown
- 1997-04-30 AP APAP/P/1997/000976A patent/AP765A/en active
- 1997-05-04 EG EG37997A patent/EG24076A/xx active
- 1997-05-05 AR ARP970101856A patent/AR007004A1/es unknown
- 1997-05-05 ID IDP971492A patent/ID16867A/id unknown
- 1997-05-06 MY MYPI97001989A patent/MY119997A/en unknown
- 1997-05-06 ZA ZA973876A patent/ZA973876B/xx unknown
- 1997-05-06 DZ DZ970069A patent/DZ2222A1/fr active
- 1997-05-06 MA MA24595A patent/MA24171A1/fr unknown
- 1997-05-06 TN TNTNSN97074A patent/TNSN97074A1/fr unknown
- 1997-05-07 HR HR970236A patent/HRP970236B1/xx not_active IP Right Cessation
-
1998
- 1998-10-20 IS IS4874A patent/IS2080B/is unknown
- 1998-10-30 OA OA9800206A patent/OA10909A/fr unknown
- 1998-11-03 BG BG102892A patent/BG63544B1/bg unknown
- 1998-11-06 NO NO19985194A patent/NO312514B1/no unknown
Also Published As
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| NZ508304A (en) | Mesylate dihydrate salt of 5-(2-(4-(1,2 benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2(1H)-indol-2-one ( ziprasidone) useful as dopamine D2 antagonist | |
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