PH26516A - Novel dibenzothiazepine antipsychotic - Google Patents
Novel dibenzothiazepine antipsychotic Download PDFInfo
- Publication number
- PH26516A PH26516A PH35028A PH35028A PH26516A PH 26516 A PH26516 A PH 26516A PH 35028 A PH35028 A PH 35028A PH 35028 A PH35028 A PH 35028A PH 26516 A PH26516 A PH 26516A
- Authority
- PH
- Philippines
- Prior art keywords
- compound
- formula
- salt
- acid
- antipsychotic
- Prior art date
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- 230000000561 anti-psychotic effect Effects 0.000 title description 12
- YAZBBWJDISBOAL-UHFFFAOYSA-N benzo[d][1,2]benzothiazepine Chemical compound S1N=CC2=CC=CC=C2C2=CC=CC=C12 YAZBBWJDISBOAL-UHFFFAOYSA-N 0.000 title 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940054010 other antipsychotics in atc Drugs 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- FWULFEHVLSQUBD-UHFFFAOYSA-N phenyl n-(2-phenylsulfanylphenyl)carbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=CC=CC=C1SC1=CC=CC=C1 FWULFEHVLSQUBD-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
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- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000000698 schizophrenic effect Effects 0.000 description 1
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- 238000012453 sprague-dawley rat model Methods 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
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- 230000001256 tonic effect Effects 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D281/16—[b, f]-condensed
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868607684A GB8607684D0 (en) | 1986-03-27 | 1986-03-27 | Thiazepine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26516A true PH26516A (en) | 1992-08-07 |
Family
ID=10595359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH35028A PH26516A (en) | 1986-03-27 | 1987-03-16 | Novel dibenzothiazepine antipsychotic |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4879288A (fr) |
| EP (1) | EP0240228B1 (fr) |
| JP (1) | JPH064606B2 (fr) |
| KR (1) | KR900001868B1 (fr) |
| AR (1) | AR242198A1 (fr) |
| AT (1) | ATE58132T1 (fr) |
| AU (1) | AU593336B2 (fr) |
| BG (1) | BG61365B2 (fr) |
| CA (1) | CA1288428C (fr) |
| CY (2) | CY1706A (fr) |
| DD (1) | DD259403A5 (fr) |
| DE (3) | DE10075017I1 (fr) |
| DK (1) | DK174618B1 (fr) |
| ES (1) | ES2019379T4 (fr) |
| FI (1) | FI86059C (fr) |
| GB (2) | GB8607684D0 (fr) |
| GR (1) | GR3001061T3 (fr) |
| HK (1) | HK85393A (fr) |
| HU (1) | HU201062B (fr) |
| IE (1) | IE59864B1 (fr) |
| IL (1) | IL81923A (fr) |
| LU (1) | LU90593I2 (fr) |
| MW (1) | MW2087A1 (fr) |
| NL (1) | NL980022I2 (fr) |
| NO (2) | NO168771C (fr) |
| NZ (1) | NZ219788A (fr) |
| PH (1) | PH26516A (fr) |
| PT (1) | PT84569B (fr) |
| ZA (1) | ZA871940B (fr) |
| ZM (1) | ZM2987A1 (fr) |
| ZW (1) | ZW5787A1 (fr) |
Families Citing this family (150)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8705574D0 (en) * | 1987-03-10 | 1987-04-15 | Ici Plc | Preparation of thiazepine compound |
| DE3827447A1 (de) * | 1988-08-12 | 1990-04-26 | Basf Ag | Polyazofarbstoffe und deren zwischenprodukte |
| US5312819A (en) * | 1990-08-20 | 1994-05-17 | Sandoz Ltd. | Pharmaceutical compositions comprising clozapine and a radical scavenger |
| GB9109557D0 (en) * | 1991-05-02 | 1991-06-26 | Wellcome Found | Chemical compounds |
| US5240927A (en) * | 1992-05-19 | 1993-08-31 | Hoechst-Roussel Pharmaceuticals Incorporated | Benzo[β]thiophen-3-yl piperazines as antipsychotic agents |
| JP2000507544A (ja) * | 1996-03-25 | 2000-06-20 | イーライ・リリー・アンド・カンパニー | 痛みの治療方法 |
| US5948437A (en) * | 1996-05-23 | 1999-09-07 | Zeneca Limited | Pharmaceutical compositions using thiazepine |
| GB9611328D0 (en) * | 1996-05-31 | 1996-08-07 | Zeneca Ltd | Pharmaceutical compositions |
| GB9716161D0 (en) * | 1997-08-01 | 1997-10-08 | Zeneca Ltd | Process |
| GB9922271D0 (en) * | 1999-09-21 | 1999-11-17 | Zeneca Ltd | Formulation |
| SE0003126D0 (sv) * | 2000-09-05 | 2000-09-05 | Astrazeneca Ab | Method of treatment |
| DE60125062T2 (de) * | 2000-12-20 | 2007-05-31 | Astrazeneca Ab | Quetiapin zur Behandlung der Dyskinesie in nicht-psychotischen Patienten |
| ES2284830T3 (es) | 2001-02-06 | 2007-11-16 | Astrazeneca Ab | Uso de quetiapina para el tratamiento de la cocaina. |
| EP1795199A3 (fr) * | 2001-02-06 | 2007-07-25 | AstraZeneca AB | Quétiapine pour traiter la dépendance à une substance ou l'abus d'une substance |
| US20040023951A1 (en) * | 2001-06-18 | 2004-02-05 | Bymaster Franklin Porter | Combination therapy for treatment of psychoses |
| SE0102855D0 (sv) * | 2001-08-27 | 2001-08-27 | Astrazeneca Ab | Method of treatment |
| PT1458888E (pt) * | 2001-12-10 | 2011-06-01 | Novartis Ag | Métodos para tratar a psicose e a esquizofrenia baseados em polimorfismos no gene do cntf |
| IL163666A0 (en) | 2002-02-22 | 2005-12-18 | New River Pharmaceuticals Inc | Active agent delivery systems and methods for protecting and administering active agents |
| JP4414237B2 (ja) * | 2002-03-20 | 2010-02-10 | テバ ファーマシューティカル インダストリーズ リミティド | ケチアピンヘミフマレートの結晶形 |
| KR100707050B1 (ko) | 2002-11-28 | 2007-04-13 | 에스케이 주식회사 | 10H-디벤조[b,f][1,4]티아제핀-11-온의 제조방법 |
| SI1583542T1 (sl) * | 2003-01-14 | 2008-12-31 | Gilead Sciences Inc | Sestavki in postopki za kombinacijsko antivirusnoterapijo |
| EP1495008A1 (fr) * | 2003-02-22 | 2005-01-12 | Teva Pharmaceutical Industries Limited | Synthese de la quetiapine et sels acceptables d'un point de vue pharmaceutique de celle-ci |
| TR200503401T1 (tr) * | 2003-03-03 | 2008-03-21 | Hetero Drugs Limited | Kuetiapin (Quetiapine) Fumarat'ın yeni polimorfları |
| US7053115B2 (en) * | 2003-04-07 | 2006-05-30 | Hetero Drugs Limited | Crystalline form of dorzolamide hydrochloride |
| EP1633400A2 (fr) * | 2003-05-16 | 2006-03-15 | Pfizer Products Inc. | Combinaisons therapeutiques d'antipsychotiques atypiques avec des modulateurs de l'acide 4-aminobutanoique et/ou des medicaments anticonvulsivants |
| MXPA05013869A (es) * | 2003-07-02 | 2006-02-28 | Astrazeneca Ab | Metabolito de quetiapina. |
| US20090093460A1 (en) * | 2003-07-02 | 2009-04-09 | Astrazeneca Ab | Compositions |
| US20090093461A1 (en) * | 2003-07-02 | 2009-04-09 | Astrazeneca Ab | Methods of Treating Anxiety and Mood Disorders |
| US20060217365A1 (en) * | 2003-07-02 | 2006-09-28 | Astrazeneca Ab | Method of treating mood disorders |
| US20060217367A1 (en) * | 2004-07-01 | 2006-09-28 | Astrazeneca Ab | Method of treating anxiety disorders |
| US20060252743A1 (en) * | 2005-01-07 | 2006-11-09 | Astrazeneca Ab | Method of treating sleep disorders |
| US20060217366A1 (en) * | 2003-07-02 | 2006-09-28 | Astrazeneca Ab | Method of treating schizophrenia and other disorders |
| US20070117789A1 (en) * | 2005-11-18 | 2007-05-24 | Astrazeneca Ab | Method of treatment |
| US20060229292A1 (en) * | 2005-01-07 | 2006-10-12 | Astrazeneca Ab | Method of treating childhood disorders |
| ES2223294B2 (es) * | 2003-08-08 | 2005-10-01 | Vita Cientifica, S.L. | Procedimiento de preparacion de un compuesto farmaceuticamente activo. |
| US20050080072A1 (en) * | 2003-09-01 | 2005-04-14 | Orchid Chemicals & Pharmaceuticals Ltd. | Process for the preparation of a thiazepine derivative |
| EP1664009B1 (fr) | 2003-09-23 | 2011-01-19 | Fermion Oy | Procede de preparation de quetiapine |
| EP1689367A1 (fr) * | 2003-10-21 | 2006-08-16 | Actavis Group HF | Preparations pharmaceutiques contenant de la quetiapine |
| GB0326148D0 (en) | 2003-11-10 | 2003-12-17 | Lilly Co Eli | Morpholine derivatives |
| WO2005063254A2 (fr) | 2003-12-22 | 2005-07-14 | Acadia Pharmaceuticals Inc. | Analogues de diaryl[a,d]cycloheptene amino substitues utilises comme agonistes muscariniques, et procedes de traitement de troubles neuropsychiatriques |
| US20050171088A1 (en) * | 2004-01-30 | 2005-08-04 | Astrazeneca Ab | Treatment of psychoses with dibenzothiazepine antipsychotic |
| US20050233010A1 (en) * | 2004-04-19 | 2005-10-20 | Satow Philip M | Lithium combinations, and uses related thereto |
| MXPA06013163A (es) * | 2004-05-11 | 2007-02-13 | Pfizer Prod Inc | Combinacion de antipsicoticos atipicos y antagonistas del receptor 5-ht1b. |
| MY147767A (en) * | 2004-06-16 | 2013-01-31 | Janssen Pharmaceutica Nv | Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders |
| AR049646A1 (es) * | 2004-06-16 | 2006-08-23 | Janssen Pharmaceutica Nv | Derivados de sulfamato y sulfamida utiles para el tratamiento de la epilepsia y trastornos relacionados |
| KR101038389B1 (ko) * | 2004-06-23 | 2011-06-01 | 에스케이바이오팜 주식회사 | 11-(4-[2-(2-히드록시에톡시)에틸]-1-피페라지닐)-디벤조[b,f][1,4]티아제핀의 제조방법 |
| TW200616608A (en) * | 2004-07-09 | 2006-06-01 | Forest Laboratories | Memantine as adjunctive treatment to atypical antipsychotics in schizophrenia patients |
| MX2007002309A (es) * | 2004-08-24 | 2007-10-08 | Johnson & Johnson | Novedosos derivados de heteroarilsulfamida benzofusionados utiles como agentes anticonvulsivos. |
| WO2006027789A1 (fr) * | 2004-09-08 | 2006-03-16 | Jubilant Organosys Limited | Procede de production de 11-[4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl]dibenzo[b,f][1,4]thiazepine et d'un sel acceptable sur le plan pharmaceutique associe |
| US20060063927A1 (en) * | 2004-09-22 | 2006-03-23 | Olga Etlin | Processes for preparing quetiapine and salts thereof |
| WO2006035293A1 (fr) * | 2004-09-27 | 2006-04-06 | Ranbaxy Laboratories Limited | Formes polymorphiques d'hemifumarate de quetiapine |
| WO2006056772A2 (fr) * | 2004-11-23 | 2006-06-01 | Pliva Hrvatska D.O.O. | Composes pharmaceutiques |
| EP1838325A1 (fr) * | 2005-01-07 | 2007-10-03 | AstraZeneca AB | Nouvelle utilisation de 11-piperazine-1-yldibenzo [b,f][1,4]thiazepine ou de son sel pharmaceutiquement acceptable et compositions pharmaceutiques orales |
| EP1841751A1 (fr) * | 2005-01-24 | 2007-10-10 | IPCA Laboratories Limited | SYNTHÈSE INDUSTRIELLE DE LA 11-[4- (2-(2-HYDROXYÉTHOXY)ÉTHYL)-1-PIPÉRAZINYL]DIBENZO[b,f]-1[1, 4]THIAZÉPINE |
| BRPI0606932A2 (pt) * | 2005-01-26 | 2009-07-28 | Elan Pharma Int Ltd | formulação, forma de dosagem, e, uso de uma quantidade terapeuticamente efetiva de uma formulação |
| ES2234447B1 (es) * | 2005-03-07 | 2006-03-01 | Union Quimico-Farmaceutica S.A. | Procedimiento para la obtencion de un derivado de 11-(4-sustituido-1-piperazinil)dibenzo(b,f)(1,4)tiazepina. |
| EP1863485A2 (fr) * | 2005-03-18 | 2007-12-12 | Abbott Laboratories | Ligand du recepteur nicotinique neuronal alpha7 et compositions antipsychotiques |
| US7488821B2 (en) * | 2005-04-04 | 2009-02-10 | Divi's Laboratories Limited | Polymorph of Quetiapine fumarate and a process for its preparation |
| US7687622B2 (en) * | 2005-04-14 | 2010-03-30 | Teva Pharmaceutical Industries, Ltd | Process for preparing quetiapine fumarate |
| US8048876B2 (en) | 2005-04-21 | 2011-11-01 | Medichem S.A. | Process for preparing quetiapine and quetiapine fumarate |
| CA2605447A1 (fr) * | 2005-04-22 | 2006-11-02 | Wyeth | Nouvelles combinaisons therapeutiques pour le traitement ou la prevention de troubles psychotiques |
| MX2007014613A (es) * | 2005-05-20 | 2008-04-02 | Johnson & Johnson | Procedimiento para la preparacion de derivados de sulfamida. |
| US20070072840A1 (en) * | 2005-05-30 | 2007-03-29 | Pandya Bhargav | Polymorphic forms of quetiapine |
| TWI471145B (zh) * | 2005-06-13 | 2015-02-01 | Bristol Myers Squibb & Gilead Sciences Llc | 單一式藥學劑量型 |
| TWI375560B (en) * | 2005-06-13 | 2012-11-01 | Gilead Sciences Inc | Composition comprising dry granulated emtricitabine and tenofovir df and method for making the same |
| WO2007004234A1 (fr) * | 2005-07-04 | 2007-01-11 | Usv Limited | PROCÉDÉ DE PRÉPARATION DU FUMARATE DE 2-[2-(4-DIBENZO[b,f][L,4]THIAZÉPIN-11-YL-1-PIPÉRAZINYL)ÉTHOXY]ÉTHANOL |
| GB0516603D0 (en) * | 2005-08-12 | 2005-09-21 | Sandoz Ag | Processes for the preparation of organic compounds useful as serotonin receptor antagonists |
| WO2007036599A1 (fr) | 2005-09-30 | 2007-04-05 | Fermion Oy | Nouveau procede de cristallisation d'hemifumarate de quetiapine |
| AU2006311577B2 (en) | 2005-11-09 | 2013-02-07 | Zalicus Inc. | Methods, compositions, and kits for the treatment of medical conditions |
| WO2009151393A1 (fr) * | 2008-06-14 | 2009-12-17 | Astrazeneca Ab | Nouveaux dérivés de la 11-pipérazin-l-yldibenzo[b,f][l,4]thiazépine pour traiter au moins un syndrome ou un état associé à la schizophrénie et autres troubles psychotiques |
| TW200735878A (en) * | 2005-11-18 | 2007-10-01 | Astrazeneca Ab | Pharmaceutical compositions |
| US8389510B2 (en) * | 2005-11-18 | 2013-03-05 | Astrazeneca Ab | Crystalline forms |
| WO2009151392A1 (fr) * | 2008-06-14 | 2009-12-17 | Astrazeneca Ab | Nouveaux dérivés de 11-pipérazine-1-yldibenzo [b,f] [1,4] thiazépine pour traiter au moins un syndrome ou un état associé à la schizophrénie ou autres troubles psychotiques |
| US8497298B2 (en) * | 2005-12-19 | 2013-07-30 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocycle sulfamide derivatives for lowering lipids and lowering blood glucose levels |
| US20070155824A1 (en) * | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives for disease modification / epileptogenesis |
| US20070155823A1 (en) * | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives as neuroprotective agents |
| US8691867B2 (en) * | 2005-12-19 | 2014-04-08 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of substance abuse and addiction |
| US8716231B2 (en) | 2005-12-19 | 2014-05-06 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of pain |
| US20070155827A1 (en) * | 2005-12-19 | 2007-07-05 | Smith-Swintosky Virginia L | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of depression |
| US8937096B2 (en) | 2005-12-19 | 2015-01-20 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocyle sulfamide derivatives for the treatment of mania and bipolar disorder |
| AR058389A1 (es) * | 2005-12-19 | 2008-01-30 | Janssen Pharmaceutica Nv | Uso de derivados heterociclicos benzo-fusionados de sulfamida para el tratamiento de la obesidad |
| US20100178333A1 (en) * | 2006-01-25 | 2010-07-15 | Astron Research Limited | Sustained release dosage form of phenothiazine derivatives containing channelizer |
| US20070191460A1 (en) * | 2006-02-15 | 2007-08-16 | Smith-Swintosky Virginia L | Use of Benzo-Heteroaryl Sulfamide Derivatives for the Treatment of Disease Modification / Epileptogenesis |
| US20070191451A1 (en) * | 2006-02-15 | 2007-08-16 | Smith-Swintosky Virginia L | Use of benzo-heteroaryl sulfamide derivatives as neuroprotective agents |
| US20070191450A1 (en) * | 2006-02-15 | 2007-08-16 | Smith-Swintosky Virginia L | Use of Benzo-Heteroaryl Sulfamide Derivatives for the Treatment of Mania and Bipolar Disorder |
| US20070191474A1 (en) * | 2006-02-15 | 2007-08-16 | Smith-Swintosky Virginia L | Use of benzo-fused heterocyle sulfamide derivatives for the treatment of migraine |
| WO2007102074A2 (fr) * | 2006-03-07 | 2007-09-13 | Cadila Healthcare Limited | Sels de quetiapine |
| WO2007137167A2 (fr) * | 2006-05-19 | 2007-11-29 | Janssen Pharmaceutica N.V. | Thérapie combinée pour le traitement de l'épilepsie et de troubles apparentés |
| ATE523602T1 (de) | 2006-06-12 | 2011-09-15 | Hadasit Med Res Service | Mit durch antipsychotika induzierten extrapyramidalen symptomen assoziierte rgs2- genotypen |
| US20080004260A1 (en) * | 2006-06-29 | 2008-01-03 | Transcept Pharmaceuticals, Inc. | Compositions of 5-HT3 antagonists and dopamine D2 antagonists for treatment of dopamine-associated chronic conditions |
| CZ300451B6 (cs) * | 2006-07-03 | 2009-05-20 | Farmak, A. S. | Zpusob prípravy solí 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]ethanolu (quetiapinu) a jejich cištení |
| WO2008047340A1 (fr) * | 2006-10-19 | 2008-04-24 | Mor Research Applications Ltd. | Thérapies combinées d'antipsychotiques et de tétracyclines dans le traitement de troubles psychiatriques |
| WO2008066620A2 (fr) * | 2006-10-20 | 2008-06-05 | Concert Pharmaceuticals Inc. | Dérivés de dibenzodiazépine |
| CN101610774B (zh) * | 2006-11-03 | 2012-04-04 | 萨斯喀彻温大学 | 治疗脱髓鞘疾病的方法 |
| PT103884A (pt) | 2006-11-17 | 2008-05-19 | Astrazeneca Ab | Composições de libertação prolongada e métodos para a sua preparação |
| HUE032743T2 (en) | 2006-11-22 | 2017-10-30 | Clinical Res Ass Llc | A method for treating Down syndrome, fragilis X syndrome and autism |
| CN101616585A (zh) * | 2006-12-20 | 2009-12-30 | 阿斯利康(瑞典)有限公司 | 化合物及其用途 |
| JP2010531292A (ja) * | 2006-12-20 | 2010-09-24 | アストラゼネカ・アクチエボラーグ | 化合物及びその使用 |
| WO2008110337A2 (fr) | 2007-03-09 | 2008-09-18 | Synthon B.V. | Composition pharmaceutique de fumarate de quétiapine |
| CN100569761C (zh) * | 2007-04-18 | 2009-12-16 | 湖南洞庭药业股份有限公司 | 制备药物纯富马酸喹硫平的生产方法 |
| WO2009004480A2 (fr) * | 2007-05-07 | 2009-01-08 | Actavis Group Ptc Ehf | Sels de quétiapine et leurs polymorphes |
| HU230144B1 (hu) * | 2007-06-12 | 2015-09-28 | Richter Gedeon Nyrt. | Eljárás quetiapin előállítására |
| US20090082334A1 (en) * | 2007-09-25 | 2009-03-26 | Protia, Llc | Deuterium-enriched quetiapine |
| US20090220593A1 (en) * | 2008-01-29 | 2009-09-03 | Gulati Inder | Extended release dosage forms of quetiapine |
| CA2711395A1 (fr) * | 2008-01-31 | 2009-08-06 | Fermion Oy | Procede de preparation de quetiapine |
| CA2716080C (fr) | 2008-02-20 | 2016-12-13 | Targia Pharmaceuticals | Compositions pharmaceutiques actives sur le snc et methodes d'utilisation |
| US20090247617A1 (en) * | 2008-03-26 | 2009-10-01 | Abdel-Magid Ahmed F | Process for the preparation of benzo-fused heteroaryl sulfamates |
| US20090264408A1 (en) * | 2008-04-17 | 2009-10-22 | Gulati Inder | Extended release dosage forms of quetiapine |
| WO2009128058A1 (fr) | 2008-04-18 | 2009-10-22 | UNIVERSITY COLLEGE DUBLIN, NATIONAL UNIVERSITY OF IRELAND, DUBLIN et al | Produits psycho-pharmaceutiques |
| KR20110019781A (ko) | 2008-06-20 | 2011-02-28 | 아스트라제네카 아베 | 디벤조티아제핀 유도체 및 그의 용도 |
| AU2009271362B2 (en) | 2008-06-23 | 2014-03-13 | Janssen Pharmaceutica Nv | Crystalline form of (2s)-(-)-N-(6-chloro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-sulfamide |
| WO2009156889A1 (fr) * | 2008-06-25 | 2009-12-30 | Pfizer Inc. | Composés diaryle et leurs utilisations |
| WO2010001413A2 (fr) * | 2008-07-01 | 2010-01-07 | Lupin Limited | Compositions pharmaceutiques à libération prolongée comportant la quétiapine |
| US8815939B2 (en) * | 2008-07-22 | 2014-08-26 | Janssen Pharmaceutica Nv | Substituted sulfamide derivatives |
| EP2299983A4 (fr) * | 2008-07-24 | 2012-10-10 | Handa Pharmaceuticals Llc | Formulation antipsychotique atypique stabilisée |
| EA018638B1 (ru) * | 2008-08-01 | 2013-09-30 | Крка, Товарна Здравил, Д. Д., Ново Место | Композиция кветиапина |
| EP2153834A3 (fr) | 2008-08-07 | 2010-02-24 | Farmaprojects, S.A. | Compositions pharmaceutiques à libération prolongée comportant des sels de quétiapine |
| DE102008046650A1 (de) * | 2008-09-10 | 2010-03-11 | Tiefenbacher Pharmachemikalien Alfred E. Tiefenbacher Gmbh & Co. Kg | Quetiapin enthaltende Retardtablette |
| JP2012502915A (ja) | 2008-09-15 | 2012-02-02 | バイオビスタ インコーポレイテッド | てんかんを治療する組成物及び方法 |
| EP2373319B1 (fr) * | 2009-01-05 | 2013-07-31 | Torrent Pharmaceuticals Limited | Composition pharmaceutique à libération prolongée à base de quétiapine et son procédé de préparation |
| WO2010089259A2 (fr) | 2009-02-04 | 2010-08-12 | Woerwag R&D Gmbh | Composition à libération prolongée contenant de la quétiapine |
| JP2012519683A (ja) | 2009-03-04 | 2012-08-30 | ランバクシー ラボラトリーズ リミテッド | フマル酸クエチアピンの調製方法 |
| EP2233130A1 (fr) | 2009-03-23 | 2010-09-29 | Genepharm (Europe) Trading Limited | Composition orale à libération prolongée d'un agent antipsychotique |
| US20100298397A1 (en) * | 2009-05-19 | 2010-11-25 | Singh Nikhilesh N | Method of treatment of obsessive compulsive disorder with ondansetron |
| US8252801B1 (en) | 2009-06-03 | 2012-08-28 | Abbott Laboratories | Treatment of schizophrenia and related disorders |
| CA2785846C (fr) | 2009-12-31 | 2015-07-07 | Kempharm, Inc. | Conjugues d'acides amines de quetiapine, procede de fabrication et d'utilisation de ceux-ci |
| SI2544536T1 (sl) * | 2010-03-11 | 2019-03-29 | Kempharm, Inc. | Maščobno kislinski konjugati kvetiapina proces za njih izdelavo in uporabo |
| HRP20240109T1 (hr) | 2010-08-23 | 2024-03-29 | Alkermes Pharma Ireland Limited | Postupci za liječenje povećanja tjelesne težine induciranog antipsihoticima |
| TR201008261A1 (tr) | 2010-10-08 | 2012-04-24 | Sanovel İlaç San. Ve Ti̇c. A.Ş. | Kontrollü salım gerçekleştiren ketiapin formülasyonları |
| US8741888B2 (en) | 2010-11-09 | 2014-06-03 | Carl A. Forest | Sleep aid composition and method |
| JP5916746B2 (ja) | 2010-11-15 | 2016-05-11 | エージンバイオ, インコーポレイテッド | 認知障害を処置するためのピリダジン誘導体、組成物、および方法 |
| TR201104977A1 (tr) | 2011-05-23 | 2012-12-21 | Sanovel İlaç Sanayi̇ Ve Ti̇caret Anoni̇m Şi̇rketi̇ | Kontrollü salım gerçekleştiren kaplamaya sahip ketiapin formülasyonu. |
| WO2013074048A2 (fr) | 2011-08-08 | 2013-05-23 | Mahmut Bilgic | Formes pharmaceutiques de type comprimés comprenant un fumarate de quétiapine |
| CN102391208A (zh) * | 2011-10-25 | 2012-03-28 | 湖南洞庭药业股份有限公司 | 富马酸喹硫平的新晶形i及其制备方法 |
| WO2013095312A1 (fr) | 2011-12-19 | 2013-06-27 | Mahmut Bilgic | Formulations comprenant du fumarate de quétiapine |
| WO2013100879A1 (fr) | 2011-12-27 | 2013-07-04 | Mahmut Bilgic | Compositions pharmaceutiques contenant de la quétiapine |
| US20150018362A1 (en) | 2012-02-27 | 2015-01-15 | Biovista, Inc. | Compositions and methods for treating mitochondrial diseases |
| JP6440625B2 (ja) | 2012-11-14 | 2018-12-19 | ザ・ジョンズ・ホプキンス・ユニバーシティー | 精神分裂病を処置するための方法および組成物 |
| EP2848244A1 (fr) | 2013-09-16 | 2015-03-18 | Yildiz Özsoy Erginer | Formulations de comprimé à libération prolongée de la quétiapine |
| AU2014368961B2 (en) | 2013-12-20 | 2019-10-17 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| CN104016945B (zh) * | 2014-05-27 | 2016-06-29 | 渭南畅通药化科技有限公司 | 一种半富马酸喹硫平的制备方法 |
| EP3310785B1 (fr) | 2015-06-19 | 2024-11-20 | Agenebio, Inc. | Dérivés de benzodiazépine, compositions et méthodes de traitement de la déficience cognitive |
| US20180170941A1 (en) | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| US11505555B2 (en) | 2016-12-19 | 2022-11-22 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| MX2020013927A (es) | 2018-06-19 | 2021-03-02 | Agenebio Inc | Derivados de benzodiazepina, composiciones y metodos para tratar el deterioro cognitivo. |
| WO2020025579A1 (fr) | 2018-07-31 | 2020-02-06 | Medichem, S.A. | Forme posologique solide de fumarate de quétiapine |
| EP4213817A1 (fr) | 2020-09-21 | 2023-07-26 | Sun Pharmaceutical Industries Limited | Composition pharmaceutique multiparticulaire de quétiapine |
| CN113698363A (zh) * | 2021-09-15 | 2021-11-26 | 苏州敬业医药化工有限公司 | 一种11-哌嗪-二苯并[b,f][1,4]硫氮杂卓盐酸盐的纯化方法 |
| WO2024039886A1 (fr) | 2022-08-19 | 2024-02-22 | Agenebio, Inc. | Dérivés de benzoazépine, compositions et méthodes de traitement de déficience cognitive |
| WO2025172499A1 (fr) | 2024-02-15 | 2025-08-21 | Itf Research Pharma, S.L.U | Formulations liquides de quétiapine |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3389139A (en) * | 1963-06-14 | 1968-06-18 | Wander Ag Dr A | 6-homopiperazino and piperazinomorphanthridines |
| FR127F (fr) * | 1964-03-27 | |||
| FR90378E (fr) * | 1965-03-26 | 1968-02-14 | ||
| US3539573A (en) * | 1967-03-22 | 1970-11-10 | Jean Schmutz | 11-basic substituted dibenzodiazepines and dibenzothiazepines |
| CH539044A (de) * | 1967-10-06 | 1973-08-31 | Gnii Orch Poluproduktov I Kras | Verfahren zur Herstellung quaternärer Ammoniumsalze von 1,3-Bis-(aminomethyl)-imidazolidonen |
| US3928356A (en) * | 1967-10-06 | 1975-12-23 | Fujisawa Pharmaceutical Co | 10-{8 4-({107 -Hydroxy alkyl)-1-piperazimyl{9 -dibenzo (h,f) oxofins and thiepins and acetyl esters thereof |
| GB1262509A (en) * | 1969-06-20 | 1972-02-02 | Science Union & Cie | New tricyclic derivatives and process for their preparation |
| CA918659A (en) * | 1969-07-31 | 1973-01-09 | Yoshitomi Pharmaceutical Industries | 11-(4-substituted-1-piperazinyl)-dibenzo (b,f) (1,4) thiazepines |
| BE787249A (fr) * | 1971-08-05 | 1973-02-05 | Squibb & Sons Inc | Derives amino d'acides pyrazolopyridine carboxyliques, leurs esters et les sels de ces composes, ainsi que leurs procedes de preparation |
| BE792426A (fr) * | 1971-12-09 | 1973-06-07 | Wander Ag Dr A | Nouveaux derives de la dibenzo(b,f)(1,4)thiazepine, leur preparation etleur application comme medicaments |
| US3962248A (en) * | 1972-04-04 | 1976-06-08 | Sandoz, Inc. | Process for making 11-piperazino-diazepines, oxazepines, thiazepines and azepines |
| CH569731A5 (fr) * | 1972-04-04 | 1975-11-28 | Wander Ag Dr A | |
| CH624682A5 (fr) * | 1976-11-10 | 1981-08-14 | Sandoz Ag | |
| US4096261A (en) * | 1977-02-23 | 1978-06-20 | Abbott Laboratories | Dibenzodiazepines |
| US4097597A (en) * | 1977-02-23 | 1978-06-27 | Abbott Laboratories | Dibenzo b,e! 1,4!diazepines |
-
1986
- 1986-03-27 GB GB868607684A patent/GB8607684D0/en active Pending
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1987
- 1987-03-16 IE IE70087A patent/IE59864B1/en not_active IP Right Cessation
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- 1987-03-16 PH PH35028A patent/PH26516A/en unknown
- 1987-03-17 ZA ZA871940A patent/ZA871940B/xx unknown
- 1987-03-17 DD DD87300862A patent/DD259403A5/de unknown
- 1987-03-18 IL IL81923A patent/IL81923A/xx not_active IP Right Cessation
- 1987-03-19 MW MW20/87A patent/MW2087A1/xx unknown
- 1987-03-20 AU AU70459/87A patent/AU593336B2/en not_active Expired
- 1987-03-20 US US07/028,473 patent/US4879288A/en not_active Expired - Lifetime
- 1987-03-24 EP EP87302539A patent/EP0240228B1/fr not_active Expired - Lifetime
- 1987-03-24 DE DE2000175017 patent/DE10075017I1/de active Pending
- 1987-03-24 AT AT87302539T patent/ATE58132T1/de active
- 1987-03-24 ZW ZW57/87A patent/ZW5787A1/xx unknown
- 1987-03-24 DE DE2000175016 patent/DE10075016I2/de active Active
- 1987-03-24 DE DE8787302539T patent/DE3765969D1/de not_active Expired - Lifetime
- 1987-03-24 ZM ZM29/87A patent/ZM2987A1/xx unknown
- 1987-03-24 ES ES87302539.9T patent/ES2019379T4/es not_active Expired - Lifetime
- 1987-03-24 GB GB878706949A patent/GB8706949D0/en active Pending
- 1987-03-26 NO NO871267A patent/NO168771C/no not_active IP Right Cessation
- 1987-03-26 PT PT84569A patent/PT84569B/pt unknown
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- 1987-03-27 HU HU871342A patent/HU201062B/hu unknown
- 1987-03-27 KR KR1019870002852A patent/KR900001868B1/ko not_active Expired
- 1987-03-27 DK DK198701585A patent/DK174618B1/da not_active IP Right Cessation
- 1987-03-27 AR AR87307138A patent/AR242198A1/es active
- 1987-03-27 CA CA000533171A patent/CA1288428C/fr not_active Expired - Lifetime
- 1987-03-27 JP JP62071962A patent/JPH064606B2/ja not_active Expired - Lifetime
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1990
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1993
- 1993-08-19 HK HK853/93A patent/HK85393A/en not_active IP Right Cessation
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- 1994-01-14 CY CY170694A patent/CY1706A/xx unknown
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