NO300685B1 - Fremgangsmåte for fremstilling av arylpiperazinyl-heterocykliske forbindelser - Google Patents
Fremgangsmåte for fremstilling av arylpiperazinyl-heterocykliske forbindelser Download PDFInfo
- Publication number
- NO300685B1 NO300685B1 NO931656A NO931656A NO300685B1 NO 300685 B1 NO300685 B1 NO 300685B1 NO 931656 A NO931656 A NO 931656A NO 931656 A NO931656 A NO 931656A NO 300685 B1 NO300685 B1 NO 300685B1
- Authority
- NO
- Norway
- Prior art keywords
- neutralizing agent
- compound
- approx
- formula
- piperazine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 32
- 238000002360 preparation method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 14
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 238000005859 coupling reaction Methods 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 238000010168 coupling process Methods 0.000 claims abstract description 8
- 230000008878 coupling Effects 0.000 claims abstract description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 4
- 230000000694 effects Effects 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- -1 6-hydroxy-8-quinolyl Chemical group 0.000 claims description 35
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 230000003472 neutralizing effect Effects 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
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- 239000000758 substrate Substances 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 6
- 125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000004885 piperazines Chemical class 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 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 claims description 3
- 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 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 231100000241 scar Toxicity 0.000 claims 1
- 150000008648 triflates Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 19
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- DOQLJTKEUIJSKK-UHFFFAOYSA-N 3-piperazin-1-yl-1,2-benzothiazole;hydrochloride Chemical compound Cl.C1CNCCN1C1=NSC2=CC=CC=C12 DOQLJTKEUIJSKK-UHFFFAOYSA-N 0.000 description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZDFQBFVFCPABKQ-UHFFFAOYSA-N 3-piperazin-1-yl-1,2-benzoxazole Chemical class C1CNCCN1C1=NOC2=CC=CC=C12 ZDFQBFVFCPABKQ-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
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- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
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- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
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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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Management, Administration, Business Operations System, And Electronic Commerce (AREA)
- Eye Examination Apparatus (AREA)
- Lubricants (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/936,179 US5206366A (en) | 1992-08-26 | 1992-08-26 | Process for preparing aryl piperazinyl-heterocyclic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO931656D0 NO931656D0 (no) | 1993-05-06 |
| NO931656L NO931656L (no) | 1994-02-28 |
| NO300685B1 true NO300685B1 (no) | 1997-07-07 |
Family
ID=25468285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO931656A NO300685B1 (no) | 1992-08-26 | 1993-05-06 | Fremgangsmåte for fremstilling av arylpiperazinyl-heterocykliske forbindelser |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5206366A (zh) |
| EP (2) | EP0584903B1 (zh) |
| JP (1) | JP2742370B2 (zh) |
| KR (1) | KR0123441B1 (zh) |
| CN (1) | CN1033089C (zh) |
| AT (2) | ATE206422T1 (zh) |
| AU (1) | AU642836B1 (zh) |
| BR (1) | BR9302065A (zh) |
| CZ (1) | CZ281893B6 (zh) |
| DE (2) | DE69333597T2 (zh) |
| DK (2) | DK1029861T3 (zh) |
| EG (1) | EG20214A (zh) |
| ES (2) | ES2161703T3 (zh) |
| FI (1) | FI111641B (zh) |
| HU (1) | HU223312B1 (zh) |
| IL (1) | IL105622A (zh) |
| MX (1) | MX9302813A (zh) |
| MY (1) | MY109731A (zh) |
| NO (1) | NO300685B1 (zh) |
| NZ (1) | NZ247539A (zh) |
| PL (1) | PL173840B1 (zh) |
| PT (2) | PT584903E (zh) |
| RU (1) | RU2061695C1 (zh) |
| SI (1) | SI9300287A (zh) |
| SK (1) | SK280584B6 (zh) |
| YU (1) | YU48964B (zh) |
| ZA (1) | ZA936225B (zh) |
Families Citing this family (46)
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|---|---|---|---|---|
| US5338846A (en) * | 1992-08-26 | 1994-08-16 | Pfizer Inc. | Process for preparing aryl piperazinyl-heterocyclic compounds with a piperazine salt |
| US5206366A (en) * | 1992-08-26 | 1993-04-27 | Pfizer Inc. | Process for preparing aryl piperazinyl-heterocyclic compounds |
| 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 |
| WO1996039397A1 (en) * | 1995-06-06 | 1996-12-12 | Hoechst Marion Roussel, Inc. | Benzisoxazole and indazole derivatives as antipsychotic agents |
| KR100333214B1 (ko) * | 1996-05-07 | 2002-06-20 | 디. 제이. 우드, 스피겔 알렌 제이 | 5-(2-(4-(1,2-벤즈이소티아졸-3-일)-1-피페라지닐)에틸)-6-클로로-1,3-디하이드로-2(1에이치)인돌-2-온(지프라시돈)의메실레이트트리하이드레이트염,이의제조방법및도파민디2길항물질로서의이의용도 |
| TW491847B (en) | 1996-05-07 | 2002-06-21 | Pfizer | Mesylate dihydrate salts of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2h-indol-2-one |
| US5945421A (en) * | 1997-08-11 | 1999-08-31 | Warner-Lambert Company | Dopamine D4 receptor antagonists |
| US6040448A (en) * | 1997-10-24 | 2000-03-21 | Neurogen Corporation | Certain 1-(2-naphthyl) and 1-(2-azanaphthyl)-4-(1-phenylmethyl) piperazines, dopamine receptor subtype specific ligands |
| IL127497A (en) * | 1997-12-18 | 2002-07-25 | Pfizer Prod Inc | Medicinal products containing piperazinyl-heterocyclic compounds for the treatment of psychiatric disorders |
| NZ506217A (en) * | 1998-03-06 | 2002-05-31 | Astra Ab | Compound for treatment of tuberculosis and other mycobacterial diseases |
| US6150366A (en) * | 1998-06-15 | 2000-11-21 | Pfizer Inc. | Ziprasidone formulations |
| US6660858B2 (en) | 2001-03-28 | 2003-12-09 | Lion Bioscience Ag | 2-aminobenzoxazole derivatives and combinatorial libraries thereof |
| 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 |
| AP2005003250A0 (en) * | 2002-09-17 | 2005-03-31 | Warner Lambert Co | Heterocyclic substituted piperazines for the treatment of schizophrenia. |
| EP1556378B1 (en) * | 2002-10-24 | 2008-01-09 | Pfizer Products Inc. | Acyl derivatives of 5-(2-(4-(1,2 benzisothiazole-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2h-indol-2-one having neuroleptic activity |
| MXPA05004273A (es) * | 2002-11-08 | 2005-10-18 | Warner Lambert Co | Derivados de fenilalquil y piridilalquil piperazina. |
| WO2004050655A1 (en) * | 2002-12-04 | 2004-06-17 | Dr. Reddy's Laboratories Limited | Polymorphic forms of ziprasidone and its hydrochloride |
| AU2003300814A1 (en) | 2002-12-04 | 2004-06-23 | Dr. Reddy's Laboratories Inc. | Polymorphic forms of ziprasidone and its hydrochloride |
| CN1255105C (zh) * | 2002-12-17 | 2006-05-10 | 上海医药工业研究院 | 齐拉西酮及其盐的水溶性包合物及其制备方法 |
| US20050143396A1 (en) * | 2003-04-11 | 2005-06-30 | Hertero Drugs Limited | Novel crystalline forms of ziprasidone hydrochloride |
| KR20060015750A (ko) * | 2003-06-03 | 2006-02-20 | 테바 파마슈티컬 인더스트리즈 리미티드 | 지프라시돈 ＨＣｌ의 다형 형태 및 그 제조 방법 |
| US20050049295A1 (en) * | 2003-06-12 | 2005-03-03 | Dr. Reddy's Laboratories Limited | Process for the preparation of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1piperazinyl) ethyl)-6-chloro-1, 3-dihydro-2h-indol-2-one hydrochloride (ziprasidone hydrochloride) and its intermediate |
| US7160888B2 (en) * | 2003-08-22 | 2007-01-09 | Warner Lambert Company Llc | [1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia |
| EP1628973A2 (en) | 2003-10-24 | 2006-03-01 | Teva Pharmaceutical Industries Ltd. | Processes for preparation of ziprasidone |
| US20050197347A1 (en) * | 2003-12-18 | 2005-09-08 | Judith Aronhime | Polymorphic form B2 of ziprasidone base |
| PT1720867E (pt) * | 2004-02-27 | 2010-01-28 | Ranbaxy Lab Ltd | Processo para a preparação de ziprasidona |
| ITMI20040944A1 (it) * | 2004-05-11 | 2004-08-11 | Dinamite Dipharma S P A In For | Polimorfo di ziprasidone cloridrato e procedimento per la sua preparazione |
| 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) |
| US7728136B2 (en) | 2004-06-18 | 2010-06-01 | Lupin Limited | Method for the preparation of aryl piperazinyl-heterocyclic compounds |
| US9044503B2 (en) * | 2004-08-27 | 2015-06-02 | University Of Kentucky Research Foundation | Amyloid peptide inactivating enzyme to treat alzheimer's disease peripherally |
| ES2250000B1 (es) * | 2004-09-29 | 2007-06-01 | Medichem, S.A. | Procedimiento para la preparacion de ziprasidona. |
| ES2250001B1 (es) * | 2004-09-29 | 2007-06-01 | Medichem, S.A. | Proceso para la purificacion de ziprasidona. |
| US7777037B2 (en) * | 2004-10-27 | 2010-08-17 | Dr. Reddy's Laboratories Limited | Ziprasidone process |
| EP1863806A1 (en) * | 2005-02-11 | 2007-12-12 | Teva Pharmaceutical Industries Ltd | Amorphous ziprasidone mesylate |
| US20060270685A1 (en) * | 2005-03-14 | 2006-11-30 | Judith Aronhime | Anhydrous ziprasidone mesylate and a process for its preparation |
| WO2006098834A2 (en) * | 2005-03-14 | 2006-09-21 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of ziprasidone mesylate |
| CN101189237A (zh) * | 2005-04-01 | 2008-05-28 | 沃尼尔·朗伯有限责任公司 | 用于治疗精神分裂症的四氢－吡啶并氮杂䓬－8－酮和相关化合物 |
| HU230479B1 (hu) * | 2006-05-02 | 2016-07-28 | Richter Gedeon Nyrt. | Eljárás 5-{2-[4-(1,2-benzizotiazol-3-il)-1-piperazinil]-etil}-6-klór-1,3-dihidro-2H-indol-2-on (Ziprasidon) előállítására |
| HUP0600868A3 (en) * | 2006-11-24 | 2009-03-30 | Richter Gedeon Nyrt | 5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-6-chloro-1,3-dihydro-2h-indol-2-one hydrogen bromide polimorphs and process for their preparation |
| US8410268B2 (en) * | 2008-03-11 | 2013-04-02 | Alkem Laboratories Limited | Process for the preparation of ziprasidone |
| JP2013526542A (ja) | 2010-05-12 | 2013-06-24 | アッヴィ・インコーポレイテッド | キナーゼのインダゾール阻害薬 |
| PL391810A1 (pl) | 2010-07-14 | 2012-01-16 | Zakłady Farmaceutyczne POLPHARMA Spółka Akcyjna | Nowe sole ziprasidonu oraz sposoby ich otrzymywania |
| WO2012020424A1 (en) | 2010-08-12 | 2012-02-16 | Arch Pharmalabs Limited | A short process for the preparation of ziprasidone and intermediates thereof |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4610988A (en) * | 1982-04-09 | 1986-09-09 | Hoechst-Roussel Pharmaceuticals Inc. | 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-(substituted)piperazines useful for alleviating pain |
| FR2536749A1 (fr) * | 1982-11-25 | 1984-06-01 | Cerm Cent Europ Rech Mauvernay | (amino-2 ethyl)-6 benzoxazolinones substituees, leur preparation et leurs applications en therapeutique |
| 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 |
| US4883795A (en) * | 1988-01-22 | 1989-11-28 | Pfizer Inc. | Piperazinyl-heterocyclic compounds |
| 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 |
-
1992
- 1992-08-26 US US07/936,179 patent/US5206366A/en not_active Expired - Lifetime
-
1993
- 1993-05-03 NZ NZ247539A patent/NZ247539A/xx not_active IP Right Cessation
- 1993-05-04 HU HU9301291A patent/HU223312B1/hu not_active IP Right Cessation
- 1993-05-04 FI FI932012A patent/FI111641B/fi active Protection Beyond IP Right Term
- 1993-05-05 AU AU38403/93A patent/AU642836B1/en not_active Ceased
- 1993-05-06 NO NO931656A patent/NO300685B1/no unknown
- 1993-05-06 IL IL105622A patent/IL105622A/en not_active IP Right Cessation
- 1993-05-07 ES ES93303576T patent/ES2161703T3/es not_active Expired - Lifetime
- 1993-05-07 PT PT93303576T patent/PT584903E/pt unknown
- 1993-05-07 DK DK00201940T patent/DK1029861T3/da active
- 1993-05-07 AT AT93303576T patent/ATE206422T1/de not_active IP Right Cessation
- 1993-05-07 DE DE69333597T patent/DE69333597T2/de not_active Expired - Lifetime
- 1993-05-07 DK DK93303576T patent/DK0584903T3/da active
- 1993-05-07 AT AT00201940T patent/ATE273976T1/de active
- 1993-05-07 ES ES00201940T patent/ES2225015T3/es not_active Expired - Lifetime
- 1993-05-07 EP EP93303576A patent/EP0584903B1/en not_active Expired - Lifetime
- 1993-05-07 EP EP00201940A patent/EP1029861B1/en not_active Expired - Lifetime
- 1993-05-07 PT PT00201940T patent/PT1029861E/pt unknown
- 1993-05-07 MY MYPI93000857A patent/MY109731A/en unknown
- 1993-05-07 DE DE69330853T patent/DE69330853T2/de not_active Expired - Fee Related
- 1993-05-12 CZ CZ93877A patent/CZ281893B6/cs not_active IP Right Cessation
- 1993-05-13 EG EG27793A patent/EG20214A/xx active
- 1993-05-13 MX MX9302813A patent/MX9302813A/es not_active IP Right Cessation
- 1993-05-14 SK SK485-93A patent/SK280584B6/sk not_active IP Right Cessation
- 1993-05-19 PL PL93299002A patent/PL173840B1/pl not_active IP Right Cessation
- 1993-05-26 BR BR9302065A patent/BR9302065A/pt not_active Application Discontinuation
- 1993-05-28 RU RU9393028444A patent/RU2061695C1/ru not_active IP Right Cessation
- 1993-05-28 SI SI9300287A patent/SI9300287A/sl not_active IP Right Cessation
- 1993-06-04 CN CN93106669A patent/CN1033089C/zh not_active Expired - Fee Related
- 1993-07-20 KR KR1019930013678A patent/KR0123441B1/ko not_active IP Right Cessation
- 1993-08-13 JP JP5201542A patent/JP2742370B2/ja not_active Expired - Lifetime
- 1993-08-25 YU YU56593A patent/YU48964B/sh unknown
- 1993-08-25 ZA ZA936225A patent/ZA936225B/xx unknown
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