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 PDF

Info

Publication number: SK287145B6
Authority: SK; Slovakia
Prior art keywords: thiazepine; ethyl; hydroxyethoxy; dibenzo; piperazinyl
Prior art date: 1997-08-01

Application number

SK130-2000A

Other languages

English (en)

Slovak (sk)

Other versions

SK1302000A3 (en

Inventor

Evan William Snape

Original Assignee

Astrazeneca Uk Limited

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-08-01

Filing date

1998-07-28

Publication date

2010-01-07

1998-07-28 Application filed by Astrazeneca Uk Limited filed Critical Astrazeneca Uk Limited

2000-06-12 Publication of SK1302000A3 publication Critical patent/SK1302000A3/sk

2010-01-07 Publication of SK287145B6 publication Critical patent/SK287145B6/sk

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)

SK130-2000A 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 SK287145B6 (sk)

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 (fr)	1997-08-01	1998-07-28	Derive de dibenzothiazepine cristallin et utilisation de ce dernier en tant qu'agent antipsychotique

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 (fr)
EP (2)	EP1000043B1 (fr)
JP (2)	JP2001512109A (fr)
KR (1)	KR20010022241A (fr)
CN (1)	CN1125058C (fr)
AT (2)	ATE444959T1 (fr)
AU (1)	AU739255B2 (fr)
BG (1)	BG64796B1 (fr)
BR (1)	BR9811061A (fr)
CA (1)	CA2295792C (fr)
CY (2)	CY2200161T2 (fr)
CZ (1)	CZ299225B6 (fr)
DE (4)	DE69841216D1 (fr)
EE (1)	EE04550B1 (fr)
ES (2)	ES2296575T3 (fr)
GB (2)	GB9716161D0 (fr)
HU (1)	HU228620B1 (fr)
ID (1)	ID24219A (fr)
IL (1)	IL133618A (fr)
MY (1)	MY120999A (fr)
NO (1)	NO20000484L (fr)
NZ (1)	NZ501914A (fr)
PL (1)	PL338384A1 (fr)
PT (2)	PT1000043E (fr)
RU (1)	RU2224754C2 (fr)
SI (2)	SI1000043T1 (fr)
SK (1)	SK287145B6 (fr)
TR (1)	TR200000848T2 (fr)
TW (1)	TW533207B (fr)
WO (1)	WO1999006381A1 (fr)
ZA (1)	ZA986904B (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL164155A0 (en) *	2002-03-20	2005-12-18	Teva Pharma	Crystalline forms of quetiapine hemifumarate
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
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 (fr) *	2004-09-27	2006-04-06	Ranbaxy Laboratories Limited	Formes polymorphiques d'hemifumarate de quetiapine
GB0425729D0 (en) *	2004-11-23	2004-12-22	Pliva Res & Dev Ltd	Heterocyclic compounds
WO2006056772A2 (fr) *	2004-11-23	2006-06-01	Pliva Hrvatska D.O.O.	Composes pharmaceutiques
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
EP1928849A1 (fr) *	2005-09-30	2008-06-11	Fermion Oy	Nouveau procede de cristallisation d'hemifumarate de quetiapine
US8044039B2 (en)	2005-10-28	2011-10-25	Fermion Oy	Quetiapine hemifumarate purification by crystallization
JP2009516705A (ja) *	2005-11-18	2009-04-23	アストラゼネカ・アクチエボラーグ	塩の形態
EP1951693A4 (fr) *	2005-11-18	2012-05-30	Astrazeneca Ab	Formulations solides
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1997
- 1997-08-01 GB GBGB9716161.6A patent/GB9716161D0/en active Pending
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Also Published As

Publication number	Publication date
PL338384A1 (en)	2000-10-23
EP1589008B1 (fr)	2011-01-19
EP1000043A1 (fr)	2000-05-17
HU228620B1 (en)	2013-04-29
TW533207B (en)	2003-05-21
KR20010022241A (ko)	2001-03-15
SI1000043T1 (sl)	2010-01-29
EP1589008A1 (fr)	2005-10-26
PT1000043E (pt)	2009-11-30
ATE444959T1 (de)	2009-10-15
DE69842104D1 (de)	2011-03-03
ES2296568T3 (es)	2011-05-06
HK1029992A1 (en)	2001-04-20
CY2200161T2 (el)	2010-07-28
CN1265101A (zh)	2000-08-30
IL133618A (en)	2004-02-08
IL133618A0 (en)	2001-04-30
NO20000484D0 (no)	2000-01-31
NZ501914A (en)	2001-09-28
HK1081962A1 (en)	2006-05-26
ID24219A (id)	2000-07-13
CY2200162T2 (el)	2010-07-28
JP2001512109A (ja)	2001-08-21
BR9811061A (pt)	2000-09-19
EE200000062A (et)	2000-10-16
SI1589008T1 (sl)	2011-04-29
BG104176A (en)	2000-08-31
AU739255B2 (en)	2001-10-04
EE04550B1 (et)	2005-10-17
HUP0002663A2 (hu)	2001-09-28
CN1125058C (zh)	2003-10-22
AU8549898A (en)	1999-02-22
RU2224754C2 (ru)	2004-02-27
BG64796B1 (bg)	2006-04-28
CA2295792A1 (fr)	1999-02-11
GB9716161D0 (en)	1997-10-08
DE05011169T1 (de)	2008-11-06
JP2009102345A (ja)	2009-05-14
DE69841216D1 (de)	2009-11-19
ES2296575T1 (es)	2008-05-01
GB9814882D0 (en)	1998-09-09
SK1302000A3 (en)	2000-06-12
EP1000043B1 (fr)	2009-10-07
CZ2000341A3 (cs)	2000-05-17
CA2295792C (fr)	2007-04-17
WO1999006381A1 (fr)	1999-02-11
PT1589008E (pt)	2011-03-23
DE98936529T1 (de)	2008-11-20
ES2296568T1 (es)	2008-05-01
ES2296575T3 (es)	2010-02-05
CZ299225B6 (cs)	2008-05-21
MY120999A (en)	2005-12-30
HUP0002663A3 (en)	2001-10-29
NO20000484L (no)	2000-03-16
US6372734B1 (en)	2002-04-16
ZA986904B (en)	1999-02-01
US20020147186A1 (en)	2002-10-10
ATE496037T1 (de)	2011-02-15
TR200000848T2 (tr)	2000-08-21

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JPH07118262A (ja)	1995-05-09	新規１，２−ジチオール−３−チオン誘導体
KR800001545B1 (ko)	1980-12-27	피롤리딘 유도체의 제조방법
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IL27537A (en)	1970-11-30	Basically substituted oximes of 6,11-dihydrodibenzo-(b,e)-oxepinor-thiepin-11-ones and their production
WO2003042161A1 (fr)	2003-05-22	Polymorphes de chlorhydrate de venlafaxine
EP1785411A1 (fr)	2007-05-16	Forme crystalline de proptriptyline hydrochloride
HUT70181A (en)	1995-09-28	Novel arylpiperidine, process for producing thereof and pharmaceutical compositions comprising these compound

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