SK287145B6 - Farmaceutická kompozícia obsahujúca kryštalický 11-(4-(2-(2- hydroxyetoxy)etyl)-1-piperazinyl)dibenzo[b,f][1,4]tiazepín, spôsob čistenia tohto tiazepínu, spôsob prípravy kryštalického 11-(4-(2-(2-hydroxyetoxy)etyl)-1- piperazinyl)dibenzo[b,f][1,4]tiazepínu a jeho použitie - Google Patents
Farmaceutická kompozícia obsahujúca kryštalický 11-(4-(2-(2- hydroxyetoxy)etyl)-1-piperazinyl)dibenzo[b,f][1,4]tiazepín, spôsob čistenia tohto tiazepínu, spôsob prípravy kryštalického 11-(4-(2-(2-hydroxyetoxy)etyl)-1- piperazinyl)dibenzo[b,f][1,4]tiazepínu a jeho použitie Download PDFInfo
- Publication number
- SK287145B6 SK287145B6 SK130-2000A SK1302000A SK287145B6 SK 287145 B6 SK287145 B6 SK 287145B6 SK 1302000 A SK1302000 A SK 1302000A SK 287145 B6 SK287145 B6 SK 287145B6
- Authority
- SK
- Slovakia
- Prior art keywords
- thiazepine
- ethyl
- hydroxyethoxy
- dibenzo
- piperazinyl
- Prior art date
Links
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 32
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims description 16
- 150000004912 thiazepines Chemical class 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 239000003849 aromatic solvent Substances 0.000 claims abstract description 18
- 238000002425 crystallisation Methods 0.000 claims abstract description 8
- 230000008025 crystallization Effects 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 7
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 5
- 239000003085 diluting agent Substances 0.000 claims abstract description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 13
- -1 z-butyl acetate Natural products 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 7
- 239000012071 phase Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000012265 solid product Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000001530 fumaric acid 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
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000037396 body weight Effects 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
- 239000013078 crystal Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 3
- 201000000980 schizophrenia Diseases 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 3
- QPPOMEOQNLTFRU-UHFFFAOYSA-N 1,4-thiazepine Chemical compound S1C=CC=NC=C1 QPPOMEOQNLTFRU-UHFFFAOYSA-N 0.000 description 2
- VRHJBWUIWQOFLF-WLHGVMLRSA-N 2-[2-(4-benzo[b][1,4]benzothiazepin-6-ylpiperazin-1-yl)ethoxy]ethanol;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 VRHJBWUIWQOFLF-WLHGVMLRSA-N 0.000 description 2
- 229920002785 Croscarmellose sodium Polymers 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 208000012661 Dyskinesia Diseases 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229960001681 croscarmellose sodium Drugs 0.000 description 2
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 239000011928 denatured alcohol Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 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 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- BOCDFJFSOVIHBY-UHFFFAOYSA-N 2-[2-(4-benzo[b][1,4]benzothiazepin-7-ylpiperazin-1-yl)ethoxy]ethanol Chemical compound C1CN(CCOCCO)CCN1C1=CC=CC2=C1C=NC1=CC=CC=C1S2 BOCDFJFSOVIHBY-UHFFFAOYSA-N 0.000 description 1
- RSEHHYMPNZWTGQ-UHFFFAOYSA-N 3-piperazin-4-ium-1-ylpropanoate Chemical compound OC(=O)CCN1CCNCC1 RSEHHYMPNZWTGQ-UHFFFAOYSA-N 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 230000001090 anti-dopaminergic effect Effects 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- VKHYKHAWFZNIKB-UHFFFAOYSA-N benzo[b][1,4]benzothiazepine Chemical compound C1=NC2=CC=CC=C2SC2=CC=CC=C21 VKHYKHAWFZNIKB-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229940088623 biologically active substance Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000011363 dried mixture Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 208000010118 dystonia Diseases 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 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
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003557 neuropsychological effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9716161.6A GB9716161D0 (en) | 1997-08-01 | 1997-08-01 | Process |
| PCT/GB1998/002260 WO1999006381A1 (en) | 1997-08-01 | 1998-07-28 | A crystalline dibenzothiazepine derivative and its use as an antipsychotic agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK1302000A3 SK1302000A3 (en) | 2000-06-12 |
| SK287145B6 true SK287145B6 (sk) | 2010-01-07 |
Family
ID=10816746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK130-2000A SK287145B6 (sk) | 1997-08-01 | 1998-07-28 | Farmaceutická kompozícia obsahujúca kryštalický 11-(4-(2-(2- hydroxyetoxy)etyl)-1-piperazinyl)dibenzo[b,f][1,4]tiazepín, spôsob čistenia tohto tiazepínu, spôsob prípravy kryštalického 11-(4-(2-(2-hydroxyetoxy)etyl)-1- piperazinyl)dibenzo[b,f][1,4]tiazepínu a jeho použitie |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US6372734B1 (cs) |
| EP (2) | EP1589008B1 (cs) |
| JP (2) | JP2001512109A (cs) |
| KR (1) | KR20010022241A (cs) |
| CN (1) | CN1125058C (cs) |
| AT (2) | ATE496037T1 (cs) |
| AU (1) | AU739255B2 (cs) |
| BG (1) | BG64796B1 (cs) |
| BR (1) | BR9811061A (cs) |
| CA (1) | CA2295792C (cs) |
| CY (2) | CY2200161T2 (cs) |
| CZ (1) | CZ299225B6 (cs) |
| DE (4) | DE69841216D1 (cs) |
| EE (1) | EE04550B1 (cs) |
| ES (2) | ES2296568T3 (cs) |
| GB (2) | GB9716161D0 (cs) |
| HU (1) | HU228620B1 (cs) |
| ID (1) | ID24219A (cs) |
| IL (1) | IL133618A (cs) |
| MY (1) | MY120999A (cs) |
| NO (1) | NO20000484L (cs) |
| NZ (1) | NZ501914A (cs) |
| PL (1) | PL338384A1 (cs) |
| PT (2) | PT1000043E (cs) |
| RU (1) | RU2224754C2 (cs) |
| SI (2) | SI1589008T1 (cs) |
| SK (1) | SK287145B6 (cs) |
| TR (1) | TR200000848T2 (cs) |
| TW (1) | TW533207B (cs) |
| WO (1) | WO1999006381A1 (cs) |
| ZA (1) | ZA986904B (cs) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2000141A1 (en) * | 2002-03-20 | 2008-12-10 | Teva Pharmaceutical Industries Ltd. | Methods for preparing crystalline quetiapine hemifumarate |
| EP1495008A1 (en) | 2003-02-22 | 2005-01-12 | Teva Pharmaceutical Industries Limited | Synthesis of quetiapine and pharmaceutically acceptable salts thereof |
| WO2004078735A1 (en) * | 2003-03-03 | 2004-09-16 | Hetero Drugs Limited | Novel polymorphs of quetiapine fumarate |
| WO2004089957A1 (en) | 2003-04-07 | 2004-10-21 | Hetero Drugs Limited | A novel crystalline form of dorzolamide hydrochloride |
| ES2223294B2 (es) | 2003-08-08 | 2005-10-01 | Vita Cientifica, S.L. | Procedimiento de preparacion de un compuesto farmaceuticamente activo. |
| US20060081361A1 (en) * | 2004-09-13 | 2006-04-20 | Gabbey Lawrence W | Oil cooler with integral filter |
| WO2006035293A1 (en) * | 2004-09-27 | 2006-04-06 | Ranbaxy Laboratories Limited | Polymorphic forms of quetiapine hemifumarate |
| GB0425729D0 (en) * | 2004-11-23 | 2004-12-22 | Pliva Res & Dev Ltd | Heterocyclic compounds |
| WO2006056772A2 (en) * | 2004-11-23 | 2006-06-01 | Pliva Hrvatska D.O.O. | Salts of quetiapine |
| 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. |
| JP2008502707A (ja) * | 2005-04-14 | 2008-01-31 | 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 | クエチアピンフマレートの調製方法 |
| US20070072840A1 (en) * | 2005-05-30 | 2007-03-29 | Pandya Bhargav | Polymorphic forms of quetiapine |
| WO2007036599A1 (en) | 2005-09-30 | 2007-04-05 | Fermion Oy | New crystallization process of quetiapine hemifumarate |
| WO2007048870A1 (en) * | 2005-10-28 | 2007-05-03 | Fermion Oy | Quetiapine hemifumarate purification by crystallization |
| US8389510B2 (en) * | 2005-11-18 | 2013-03-05 | Astrazeneca Ab | Crystalline forms |
| WO2007062338A2 (en) * | 2005-11-18 | 2007-05-31 | Astrazeneca Ab | Solid formulations |
| EP1951258A4 (en) * | 2005-11-18 | 2013-01-02 | Astrazeneca Ab | LIQUID FORMULATIONS |
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| ATE480227T1 (de) | 2007-02-14 | 2010-09-15 | Lesvi Laboratorios Sl | Pharmazeutische zusammensetzungen mit quetiapinfumarat |
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| EA018638B1 (ru) | 2008-08-01 | 2013-09-30 | Крка, Товарна Здравил, Д. Д., Ново Место | Композиция кветиапина |
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| 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 |
| GB8607684D0 (en) * | 1986-03-27 | 1986-04-30 | Ici America Inc | Thiazepine compounds |
| GB8705574D0 (en) * | 1987-03-10 | 1987-04-15 | Ici Plc | Preparation of thiazepine compound |
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1997
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| Date | Code | Title | Description |
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| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20160728 |