SK6182003A3 - Crystalline and solvated forms of ondansetrone hydrochloride and preparation thereof - Google Patents

Crystalline and solvated forms of ondansetrone hydrochloride and preparation thereof Download PDF

Info

Publication number: SK6182003A3
Authority: SK; Slovakia
Prior art keywords: ondansetron; ondansetron hydrochloride; ethanol; hydrochloride form; anhydrous
Prior art date: 2000-10-30

Application number

SK618-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Rami Lidor-Hadas

Judith Aronhime

Revital Lifshitz

Shlomit Weizel

Valerie Niddam

Valerie Maymon

Original Assignee

Teva Pharma

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.)

2000-10-30

Filing date

2001-10-30

Publication date

2004-03-02

2001-10-30 Application filed by Teva Pharma filed Critical Teva Pharma

2004-03-02 Publication of SK6182003A3 publication Critical patent/SK6182003A3/sk

Links

VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 70
238000002360 preparation method Methods 0.000 title claims description 29
MKBLHFILKIKSQM-UHFFFAOYSA-N 9-methyl-3-[(2-methyl-1h-imidazol-3-ium-3-yl)methyl]-2,3-dihydro-1h-carbazol-4-one;chloride Chemical compound Cl.CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 MKBLHFILKIKSQM-UHFFFAOYSA-N 0.000 claims abstract description 242
238000000034 method Methods 0.000 claims abstract description 87
229960000770 ondansetron hydrochloride Drugs 0.000 claims abstract description 76
150000004677 hydrates Chemical class 0.000 claims abstract description 14
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 165
229960005343 ondansetron Drugs 0.000 claims description 96
FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 claims description 81
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
238000010992 reflux Methods 0.000 claims description 38
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
239000000203 mixture Substances 0.000 claims description 36
150000004683 dihydrates Chemical class 0.000 claims description 27
239000013078 crystal Substances 0.000 claims description 25
239000002245 particle Substances 0.000 claims description 24
239000000725 suspension Substances 0.000 claims description 23
150000004682 monohydrates Chemical class 0.000 claims description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
239000002904 solvent Substances 0.000 claims description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
FELGMEQIXOGIFQ-UHFFFAOYSA-N Ondansetron Chemical compound CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-UHFFFAOYSA-N 0.000 claims description 16
239000007788 liquid Substances 0.000 claims description 13
238000009826 distribution Methods 0.000 claims description 12
238000011282 treatment Methods 0.000 claims description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
238000001914 filtration Methods 0.000 claims description 10
239000000843 powder Substances 0.000 claims description 10
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
206010047700 Vomiting Diseases 0.000 claims description 6
238000002425 crystallisation Methods 0.000 claims description 6
230000008025 crystallization Effects 0.000 claims description 6
238000004090 dissolution Methods 0.000 claims description 6
206010028813 Nausea Diseases 0.000 claims description 5
230000018044 dehydration Effects 0.000 claims description 5
238000006297 dehydration reaction Methods 0.000 claims description 5
239000012452 mother liquor Substances 0.000 claims description 5
230000008693 nausea Effects 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 4
238000001704 evaporation Methods 0.000 claims description 4
230000036571 hydration Effects 0.000 claims description 4
238000006703 hydration reaction Methods 0.000 claims description 4
230000008673 vomiting Effects 0.000 claims description 4
239000008096 xylene Substances 0.000 claims description 4
238000004458 analytical method Methods 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
239000000155 melt Substances 0.000 claims description 3
238000002844 melting Methods 0.000 claims description 3
230000008018 melting Effects 0.000 claims description 3
238000001556 precipitation Methods 0.000 claims description 3
238000002604 ultrasonography Methods 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 2
150000002576 ketones Chemical group 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
238000012545 processing Methods 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 9
238000004519 manufacturing process Methods 0.000 claims 5
239000002253 acid Substances 0.000 claims 2
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical group [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims 2
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical group CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 claims 2
NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 claims 1
238000009413 insulation Methods 0.000 claims 1
239000012453 solvate Substances 0.000 abstract description 2
238000002560 therapeutic procedure Methods 0.000 abstract 1
239000000243 solution Substances 0.000 description 41
239000002585 base Substances 0.000 description 35
239000011541 reaction mixture Substances 0.000 description 33
239000007787 solid Substances 0.000 description 26
239000007790 solid phase Substances 0.000 description 24
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 15
239000002244 precipitate Substances 0.000 description 15
238000003756 stirring Methods 0.000 description 13
238000002441 X-ray diffraction Methods 0.000 description 10
150000001875 compounds Chemical class 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000007789 gas Substances 0.000 description 7
238000000634 powder X-ray diffraction Methods 0.000 description 6
238000001035 drying Methods 0.000 description 5
239000012458 free base Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
208000031649 Postoperative Nausea and Vomiting Diseases 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
235000011148 calcium chloride Nutrition 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
238000002512 chemotherapy Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
238000005259 measurement Methods 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
230000004580 weight loss Effects 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
238000001159 Fisher's combined probability test Methods 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
VRSLTNZJOUZKLX-UHFFFAOYSA-N Ondansetron hydrochloride Chemical compound O.O.Cl.CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 VRSLTNZJOUZKLX-UHFFFAOYSA-N 0.000 description 2
206010066962 Procedural nausea Diseases 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
229940127557 pharmaceutical product Drugs 0.000 description 2
239000011148 porous material Substances 0.000 description 2
238000001959 radiotherapy Methods 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
238000001757 thermogravimetry curve Methods 0.000 description 2
DSXKDTZEIWTHRO-UHFFFAOYSA-N 1,2,3,9-tetrahydrocarbazol-4-one Chemical group N1C2=CC=CC=C2C2=C1CCCC2=O DSXKDTZEIWTHRO-UHFFFAOYSA-N 0.000 description 1
101100011382 Aspergillus niger eglB gene Proteins 0.000 description 1
229910002483 Cu Ka Inorganic materials 0.000 description 1
101100285402 Danio rerio eng1a gene Proteins 0.000 description 1
101150067694 ENG1 gene Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
206010066963 Procedural vomiting Diseases 0.000 description 1
101100172292 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) DSE4 gene Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000007963 capsule composition Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
239000003245 coal Substances 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000004807 desolvation Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000007794 irritation Effects 0.000 description 1
238000007561 laser diffraction method Methods 0.000 description 1
238000002386 leaching Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000003801 milling Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229940100688 oral solution Drugs 0.000 description 1
238000010951 particle size reduction Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000011164 primary particle Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
-1 sachets Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000005549 size reduction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002411 thermogravimetry Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
238000002424 x-ray crystallography Methods 0.000 description 1
229940072018 zofran Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Hospice & Palliative Care (AREA)
Pharmacology & Pharmacy (AREA)
Otolaryngology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Steroid Compounds (AREA)

SK618-2003A 2000-10-30 2001-10-30 Crystalline and solvated forms of ondansetrone hydrochloride and preparation thereof SK6182003A3 (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US24428300P	2000-10-30	2000-10-30
US25381900P	2000-11-29	2000-11-29
US26553901P	2001-01-31	2001-01-31
PCT/US2001/048720 WO2002036558A2 (en)	2000-10-30	2001-10-30	Novel crystal and solvate forms of ondansetron hydrochloride and processes for their preparation

Publications (1)

Publication Number	Publication Date
SK6182003A3 true SK6182003A3 (en)	2004-03-02

Family

ID=27399743

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK618-2003A SK6182003A3 (en)	2000-10-30	2001-10-30	Crystalline and solvated forms of ondansetrone hydrochloride and preparation thereof

Country Status (20)

Country	Link
US (1)	US20020107275A1 (pl)
EP (1)	EP1339707A2 (pl)
JP (1)	JP2004525083A (pl)
KR (1)	KR20030042038A (pl)
CN (1)	CN1498216A (pl)
AU (1)	AU2002230935A1 (pl)
CA (1)	CA2426026A1 (pl)
CZ (1)	CZ20031397A3 (pl)
DE (1)	DE01991193T1 (pl)
ES (1)	ES2204358T1 (pl)
HR (1)	HRP20030432A2 (pl)
HU (1)	HUP0401239A2 (pl)
IL (1)	IL155644A0 (pl)
IS (1)	IS6797A (pl)
MX (1)	MXPA03003761A (pl)
NO (1)	NO20031928L (pl)
PL (1)	PL366150A1 (pl)
SK (1)	SK6182003A3 (pl)
WO (1)	WO2002036558A2 (pl)
YU (1)	YU32003A (pl)

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DE02703115T1 (de) *	2001-01-11	2004-10-21	Teva Pharmaceutical Industries Ltd.	Verbessertes verfahren zur herstellung von reinem ondansetronhydrochlorid-dihydrat
CN1665823A (zh)	2002-04-29	2005-09-07	特瓦药厂有限公司	制备1,2,3,9－四氢－9－甲基－3－[(2－甲基－1h－咪唑－1－基)甲基]－4h－咔唑－4－酮的方法
FI6164U1 (fi) *	2003-01-09	2004-03-15	Synthon Bv	Ondansetronmuotoja
WO2006046253A1 (en) *	2004-10-26	2006-05-04	Ipca Laboratories Limited	A one-pot process for the preparation of antiemetic agent, 1,2,3,9-tetrahydro-9-methyl-3[(2-methyl)-1h-imidazole-1-yl)methyl]-4h-carbazol-4-o
CA2640460C (en) *	2006-01-27	2015-05-26	Eurand, Inc	Drug delivery systems comprising weakly basic selective serotonin 5-ht3 blocking agent and organic acids
BRPI0707325A2 (pt) *	2006-01-27	2011-05-03	Eurand Inc	formulação de dosagem de liberação multiparticulada e método para preparação da mesma
JP2010512333A (ja) *	2006-12-07	2010-04-22	ヘルシンヘルスケアソシエテアノニム	塩酸パロノセトロンの結晶及び非晶質形
US8133506B2 (en)	2008-03-12	2012-03-13	Aptalis Pharmatech, Inc.	Drug delivery systems comprising weakly basic drugs and organic acids
CN102190595A (zh) *	2010-03-17	2011-09-21	上海医药工业研究院	阿戈美拉汀溴化氢水合物及其制备方法
CN102190594A (zh) *	2010-03-17	2011-09-21	上海医药工业研究院	阿戈美拉汀氯化氢水合物及其制备方法
AR099354A1 (es)	2013-11-15	2016-07-20	Akebia Therapeutics Inc	Formas sólidas de ácido {[5-(3-clorofenil)-3-hidroxipiridin-2-carbonil]amino}acético, composiciones, y sus usos

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EP0385517B1 (en) *	1985-03-14	1993-04-14	BEECHAM GROUP plc	Medicaments for the treatment of emesis
GB8518742D0 (en) *	1985-07-24	1985-08-29	Glaxo Group Ltd	Process
GB8518741D0 (en) *	1985-07-24	1985-08-29	Glaxo Group Ltd	Process
GB8630071D0 (en) *	1986-12-17	1987-01-28	Glaxo Group Ltd	Medicaments
GB8816187D0 (en) *	1988-07-07	1988-08-10	Glaxo Group Ltd	Medicaments
US5344658A (en) *	1989-06-28	1994-09-06	Glaxo Group Limited	Process and composition using ondansetron
JPH06508836A (ja) *	1991-06-26	1994-10-06	セプラコア，インコーポレーテッド	光学的に純粋なｒ（＋）オンダンセトロンを使用する嘔吐、吐き気および他の障害の治療のための方法および組成物
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GB9423511D0 (en) *	1994-11-22	1995-01-11	Glaxo Wellcome Inc	Compositions
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CN1045437C (zh) *	1994-12-29	1999-10-06	中国科学院上海有机化学研究所	恩丹西酮及其生理盐的合成
EP1207160A1 (en) *	2000-11-20	2002-05-22	Hanmi Pharm. Co., Ltd.	Process for the preparation of 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1H-imidazol-1-yl)-methyl)-4H-carbazol-4-one
CN1665823A (zh) *	2002-04-29	2005-09-07	特瓦药厂有限公司	制备1,2,3,9－四氢－9－甲基－3－[(2－甲基－1h－咪唑－1－基)甲基]－4h－咔唑－4－酮的方法
PL373192A1 (pl) *	2002-04-30	2005-08-22	Teva Gyogyszergyar Reszvenytarsasag	Nowe krystaliczne postaci ondansetronu, sposoby ich wytwarzania, kompozycje farmaceutyczne zawierające te nowe postaci oraz sposoby ich stosowania doleczenia nudności

2001
- 2001-10-30 CN CNA018183859A patent/CN1498216A/zh active Pending
- 2001-10-30 HR HR20030432A patent/HRP20030432A2/hr not_active Application Discontinuation
- 2001-10-30 ES ES01991193T patent/ES2204358T1/es active Pending
- 2001-10-30 YU YU32003A patent/YU32003A/sh unknown
- 2001-10-30 HU HU0401239A patent/HUP0401239A2/hu unknown
- 2001-10-30 AU AU2002230935A patent/AU2002230935A1/en not_active Abandoned
- 2001-10-30 SK SK618-2003A patent/SK6182003A3/sk not_active Application Discontinuation
- 2001-10-30 DE DE0001339707T patent/DE01991193T1/de active Pending
- 2001-10-30 CA CA002426026A patent/CA2426026A1/en not_active Abandoned
- 2001-10-30 EP EP01991193A patent/EP1339707A2/en not_active Withdrawn
- 2001-10-30 IL IL15564401A patent/IL155644A0/xx unknown
- 2001-10-30 MX MXPA03003761A patent/MXPA03003761A/es unknown
- 2001-10-30 US US10/016,752 patent/US20020107275A1/en not_active Abandoned
- 2001-10-30 JP JP2002539318A patent/JP2004525083A/ja active Pending
- 2001-10-30 CZ CZ20031397A patent/CZ20031397A3/cs unknown
- 2001-10-30 KR KR10-2003-7005876A patent/KR20030042038A/ko not_active Ceased
- 2001-10-30 PL PL01366150A patent/PL366150A1/pl unknown
- 2001-10-30 WO PCT/US2001/048720 patent/WO2002036558A2/en not_active Ceased
2003
- 2003-04-29 IS IS6797A patent/IS6797A/is unknown
- 2003-04-29 NO NO20031928A patent/NO20031928L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
PL366150A1 (pl)	2005-01-24
HRP20030432A2 (en)	2004-06-30
IS6797A (is)	2003-04-29
ES2204358T1 (es)	2004-05-01
NO20031928D0 (no)	2003-04-29
EP1339707A2 (en)	2003-09-03
WO2002036558A3 (en)	2003-02-06
AU2002230935A1 (en)	2002-05-15
CZ20031397A3 (cs)	2003-11-12
MXPA03003761A (es)	2003-07-28
CN1498216A (zh)	2004-05-19
CA2426026A1 (en)	2002-05-10
NO20031928L (no)	2003-06-27
DE01991193T1 (de)	2004-07-08
KR20030042038A (ko)	2003-05-27
YU32003A (sh)	2006-05-25
IL155644A0 (en)	2003-11-23
HUP0401239A2 (hu)	2004-12-28
WO2002036558A2 (en)	2002-05-10
JP2004525083A (ja)	2004-08-19
US20020107275A1 (en)	2002-08-08

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