IL133618A - Crystalline dibenzothiazepine derivatives, processes for their preparation, pharmaceutical compositions containing them and use thereof as antipsychotic agents - Google Patents
Crystalline dibenzothiazepine derivatives, processes for their preparation, pharmaceutical compositions containing them and use thereof as antipsychotic agentsInfo
- Publication number
- IL133618A IL133618A IL13361898A IL13361898A IL133618A IL 133618 A IL133618 A IL 133618A IL 13361898 A IL13361898 A IL 13361898A IL 13361898 A IL13361898 A IL 13361898A IL 133618 A IL133618 A IL 133618A
- Authority
- IL
- Israel
- Prior art keywords
- dibenzo
- thiazepine
- hydroxyethoxy
- piperazinyl
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 35
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 10
- 239000000164 antipsychotic agent Substances 0.000 title description 3
- 150000008509 dibenzothiazepines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 claims description 72
- 150000003839 salts Chemical class 0.000 claims description 36
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 25
- 239000003849 aromatic solvent Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 13
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 12
- 230000003247 decreasing effect Effects 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 8
- 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
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000012071 phase Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 239000001530 fumaric acid Substances 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 3
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 3
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- -1 hydroxyethoxy Chemical group 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base 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
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 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
- 230000015572 biosynthetic process Effects 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
- 239000012258 stirred mixture Substances 0.000 description 3
- 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
- 241000282412 Homo Species 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 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
- 230000008901 benefit Effects 0.000 description 2
- 239000002775 capsule Substances 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
- 239000002552 dosage form Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 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
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 235000015096 spirit Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- QPPOMEOQNLTFRU-UHFFFAOYSA-N 1,4-thiazepine Chemical compound S1C=CC=NC=C1 QPPOMEOQNLTFRU-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
- 229920002261 Corn starch Polymers 0.000 description 1
- 208000012661 Dyskinesia Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010034010 Parkinsonism Diseases 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
- 241000700159 Rattus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000001090 anti-dopaminergic effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229940088623 biologically active substance Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 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
- 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
- 238000005007 materials handling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 238000010992 reflux Methods 0.000 description 1
- 201000000980 schizophrenia Diseases 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
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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
- 150000004912 thiazepines Chemical class 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
- 239000003981 vehicle Substances 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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 |
|---|---|
| IL133618A0 IL133618A0 (en) | 2001-04-30 |
| IL133618A true IL133618A (en) | 2004-02-08 |
Family
ID=10816746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13361898A IL133618A (en) | 1997-08-01 | 1998-07-28 | Crystalline dibenzothiazepine derivatives, processes for their preparation, pharmaceutical compositions containing them and use thereof as antipsychotic agents |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US6372734B1 (bg) |
| EP (2) | EP1589008B1 (bg) |
| JP (2) | JP2001512109A (bg) |
| KR (1) | KR20010022241A (bg) |
| CN (1) | CN1125058C (bg) |
| AT (2) | ATE444959T1 (bg) |
| AU (1) | AU739255B2 (bg) |
| BG (1) | BG64796B1 (bg) |
| BR (1) | BR9811061A (bg) |
| CA (1) | CA2295792C (bg) |
| CY (2) | CY2200162T2 (bg) |
| CZ (1) | CZ299225B6 (bg) |
| DE (4) | DE05011169T1 (bg) |
| EE (1) | EE04550B1 (bg) |
| ES (2) | ES2296568T3 (bg) |
| GB (2) | GB9716161D0 (bg) |
| HK (2) | HK1029992A1 (bg) |
| HU (1) | HU228620B1 (bg) |
| ID (1) | ID24219A (bg) |
| IL (1) | IL133618A (bg) |
| MY (1) | MY120999A (bg) |
| NO (1) | NO20000484L (bg) |
| NZ (1) | NZ501914A (bg) |
| PL (1) | PL338384A1 (bg) |
| PT (2) | PT1589008E (bg) |
| RU (1) | RU2224754C2 (bg) |
| SI (2) | SI1589008T1 (bg) |
| SK (1) | SK287145B6 (bg) |
| TR (1) | TR200000848T2 (bg) |
| TW (1) | TW533207B (bg) |
| WO (1) | WO1999006381A1 (bg) |
| ZA (1) | ZA986904B (bg) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2479668A1 (en) * | 2002-03-20 | 2003-10-02 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of quetiapine hemifumarate |
| CA2516646A1 (en) | 2003-02-22 | 2004-09-10 | Teva Pharmaceutical Industries Ltd. | Synthesis of quetiapine and pharmaceutically acceptable salts thereof |
| TR200503401T1 (tr) * | 2003-03-03 | 2008-03-21 | Hetero Drugs Limited | Kuetiapin (Quetiapine) Fumarat'ın yeni polimorfları |
| AU2003242982A1 (en) * | 2003-04-07 | 2004-11-01 | 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. |
| WO2006113425A1 (en) | 2005-04-14 | 2006-10-26 | Teva Pharmaceutical Industries Ltd. | Process for preparing quetiapine fumarate |
| 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 |
| EP1948628A1 (en) * | 2005-10-28 | 2008-07-30 | Fermion Oy | Quetiapine hemifumarate purification by crystallization |
| JP2009516706A (ja) * | 2005-11-18 | 2009-04-23 | アストラゼネカ・アクチエボラーグ | 結晶形 |
| JP2009516708A (ja) * | 2005-11-18 | 2009-04-23 | アストラゼネカ・アクチエボラーグ | 液体製剤 |
| US8389510B2 (en) * | 2005-11-18 | 2013-03-05 | Astrazeneca Ab | Crystalline forms |
| EP1951693A4 (en) * | 2005-11-18 | 2012-05-30 | Astrazeneca Ab | SOLID FORMULATIONS |
| US20090069291A1 (en) * | 2005-11-18 | 2009-03-12 | Astrazeneca Ab | Salt Forms |
| 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 |
| WO2008066620A2 (en) * | 2006-10-20 | 2008-06-05 | Concert Pharmaceuticals Inc. | Dibenzothiazepine derivatives |
| ES2352299T3 (es) | 2007-02-14 | 2011-02-17 | Laboratorios Lesvi, S.L. | Composiciones farmacéuticas que contienen fumarato de quetiapina. |
| JP2009529062A (ja) * | 2007-03-29 | 2009-08-13 | 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 | フマル酸クエチアピンを調製するための改良法 |
| WO2009004480A2 (en) * | 2007-05-07 | 2009-01-08 | Actavis Group Ptc Ehf | Quetiapine salts and their polymorphs |
| US20090082334A1 (en) * | 2007-09-25 | 2009-03-26 | Protia, Llc | Deuterium-enriched quetiapine |
| WO2009071631A2 (en) * | 2007-12-05 | 2009-06-11 | Janssen Pharmaceutica Nv | Dibenzoazepine and dibenzooxazepine trpa1 agonists |
| EP2262486B1 (en) | 2008-08-01 | 2013-01-02 | KRKA, Tovarna Zdravil, D.D., Novo Mesto | Quetiapine composition |
| US20100069356A1 (en) * | 2008-09-17 | 2010-03-18 | Auspex Pharmaceuticals, Inc. | Dibenzothiazepine modulators of dopamine, alpha adrenergic, and serotonin receptors |
| EP2403841A1 (en) | 2009-03-04 | 2012-01-11 | Ranbaxy Laboratories Limited | Process for the preparation of quetiapine fumarate |
| EP2742152B1 (en) | 2011-08-12 | 2017-04-12 | Qiagen GmbH | Method for isolating nucleic acids |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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