NO314692B1 - Pseudopolymorfe former av 2-[2-[4-(bis(4-fluorfenyl)metyl]-1- piperazinyl]etoksy]eddiksyre dihydroklorid, fremgangsmåter for fremstilling avdisse, samt farmasöytisk preparat av dem - Google Patents

Pseudopolymorfe former av 2-[2-[4-(bis(4-fluorfenyl)metyl]-1- piperazinyl]etoksy]eddiksyre dihydroklorid, fremgangsmåter for fremstilling avdisse, samt farmasöytisk preparat av dem Download PDF

Info

Publication number: NO314692B1
Authority: NO; Norway
Prior art keywords: bis; methyl; piperazinyl; fluorophenyl; ethoxy
Prior art date: 1997-11-26

Application number

NO20002631A

Other languages

English (en)

Norwegian (no)

Other versions

NO20002631L (no

NO20002631D0 (no

Inventor

Monique Berwaer

Guy Bodson

Michel Deleers

Charles Dogimont

Domenico Fanara

Jacques Timmermans

Original Assignee

Ubc Sa

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.)

1997-11-26

Filing date

2000-05-23

Publication date

2003-05-05

2000-05-23 Application filed by Ubc Sa filed Critical Ubc Sa

2000-05-23 Publication of NO20002631L publication Critical patent/NO20002631L/no

2000-05-23 Publication of NO20002631D0 publication Critical patent/NO20002631D0/no

2003-05-05 Publication of NO314692B1 publication Critical patent/NO314692B1/no

Links

125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract description 17
238000000034 method Methods 0.000 title claims abstract description 12
IHTYTYHXCRAMAV-UHFFFAOYSA-N acetic acid;dihydrochloride Chemical compound Cl.Cl.CC(O)=O IHTYTYHXCRAMAV-UHFFFAOYSA-N 0.000 title claims abstract 13
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 title claims abstract 13
239000000825 pharmaceutical preparation Substances 0.000 title claims description 20
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 title abstract 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 19
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 15
239000007787 solid Substances 0.000 claims description 14
239000000546 pharmaceutical excipient Substances 0.000 claims description 11
239000003085 diluting agent Substances 0.000 claims description 8
238000010992 reflux Methods 0.000 claims description 8
239000000969 carrier Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
229920000858 Cyclodextrin Polymers 0.000 claims description 3
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
238000002441 X-ray diffraction Methods 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000004128 high performance liquid chromatography Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 7
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 7
238000004090 dissolution Methods 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
229960002920 sorbitol Drugs 0.000 description 7
238000003860 storage Methods 0.000 description 7
238000001228 spectrum Methods 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 4
239000008188 pellet Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000000634 powder X-ray diffraction Methods 0.000 description 3
238000001757 thermogravimetry curve Methods 0.000 description 3
IBJKCLFDIYBWFC-UHFFFAOYSA-N 2-[2-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]acetamide Chemical compound C1CN(CCOCC(=O)N)CCN1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 IBJKCLFDIYBWFC-UHFFFAOYSA-N 0.000 description 2
BAWMMJAUVBLLEE-UHFFFAOYSA-N 2-[2-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]acetic acid Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 BAWMMJAUVBLLEE-UHFFFAOYSA-N 0.000 description 2
HQWVDUUIOCFXPO-UHFFFAOYSA-N 2-[2-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]acetic acid;dihydrochloride Chemical compound Cl.Cl.C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 HQWVDUUIOCFXPO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000007906 compression Methods 0.000 description 2
230000006835 compression Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229940124531 pharmaceutical excipient Drugs 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
TTXIFFYPVGWLSE-UHFFFAOYSA-N 1-[bis(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCNCC1 TTXIFFYPVGWLSE-UHFFFAOYSA-N 0.000 description 1
KQHRCXCLILUNBX-UHFFFAOYSA-N 2-(2-chloroethoxy)acetamide Chemical compound NC(=O)COCCCl KQHRCXCLILUNBX-UHFFFAOYSA-N 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
229910016523 CuKa Inorganic materials 0.000 description 1
229920003091 Methocel™ Polymers 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000002706 dry binder Substances 0.000 description 1
229950003420 efletirizine Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
238000011002 quantification Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000009790 rate-determining step (RDS) Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pulmonology (AREA)
Neurology (AREA)
Dermatology (AREA)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Ophthalmology & Optometry (AREA)
Otolaryngology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

NO20002631A 1997-11-26 2000-05-23 Pseudopolymorfe former av 2-[2-[4-(bis(4-fluorfenyl)metyl]-1- piperazinyl]etoksy]eddiksyre dihydroklorid, fremgangsmåter for fremstilling avdisse, samt farmasöytisk preparat av dem NO314692B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP97870193A EP0919550A1 (fr)	1997-11-26	1997-11-26	Formes pseudopolymorphiques de l'acide 2-2-4-bis(4-fluorophényl)méthyl -1-pipérazinyl-éthoxy acétique dihydrochloride
PCT/BE1998/000184 WO1999028310A1 (fr)	1997-11-26	1998-11-26	Formes pseudomorphes de dichlorhydrate d'acide 2-[2-[4-[bis (4-fluorophenyl) methyl]-1-piperazinyl] ethoxy]acetique

Publications (3)

Publication Number	Publication Date
NO20002631L NO20002631L (no)	2000-05-23
NO20002631D0 NO20002631D0 (no)	2000-05-23
NO314692B1 true NO314692B1 (no)	2003-05-05

Family

ID=8231072

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20002631A NO314692B1 (no)	1997-11-26	2000-05-23	Pseudopolymorfe former av 2-[2-[4-(bis(4-fluorfenyl)metyl]-1- piperazinyl]etoksy]eddiksyre dihydroklorid, fremgangsmåter for fremstilling avdisse, samt farmasöytisk preparat av dem

Country Status (39)

Country	Link
US (2)	US6262057B1 (fr)
EP (2)	EP0919550A1 (fr)
JP (2)	JP3996348B2 (fr)
KR (1)	KR100557711B1 (fr)
CN (1)	CN100406448C (fr)
AR (1)	AR017676A1 (fr)
AT (1)	ATE203237T1 (fr)
AU (1)	AU735819B2 (fr)
BG (1)	BG64155B1 (fr)
BR (1)	BR9815405A (fr)
CA (1)	CA2310318C (fr)
CO (1)	CO4980892A1 (fr)
CZ (1)	CZ295972B6 (fr)
DE (1)	DE69801163T2 (fr)
DK (1)	DK1034171T3 (fr)
EG (1)	EG23776A (fr)
ES (1)	ES2161552T3 (fr)
GC (1)	GC0000094A (fr)
GR (1)	GR3036702T3 (fr)
HU (1)	HUP0100343A3 (fr)
ID (1)	ID24964A (fr)
IL (1)	IL135544A (fr)
MA (1)	MA26569A1 (fr)
MY (1)	MY119653A (fr)
NO (1)	NO314692B1 (fr)
NZ (1)	NZ504461A (fr)
PE (1)	PE134899A1 (fr)
PL (1)	PL190871B1 (fr)
PT (1)	PT1034171E (fr)
RS (1)	RS49904B (fr)
RU (1)	RU2182575C2 (fr)
SI (1)	SI20325A (fr)
SK (1)	SK283237B6 (fr)
TN (1)	TNSN98214A1 (fr)
TR (1)	TR200001505T2 (fr)
TW (1)	TWI225053B (fr)
UA (1)	UA54568C2 (fr)
WO (1)	WO1999028310A1 (fr)
ZA (1)	ZA9810780B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2002221854A1 (en) *	2000-12-15	2002-06-24	U C B, S.A.	Use of cetirizine or efletirizine for preventing urticaria
EP1414460A1 (fr) *	2001-07-26	2004-05-06	Ucb, S.A.	Procede de fabrication de derives d'acides 2-(2-(4-(bis(4-fluorophenyl)methyl)-piperazine-1-yl)ethoxy)acetiques ou de sels de ces composes et intermediaires correspondants
US20050181032A1 (en) *	2002-06-25	2005-08-18	Acrux Dds Pty Ltd.	Metastable pharmaceutical compositions
JP5160018B2 (ja) *	2002-06-25	2013-03-13	アクルックス・ディ・ディ・エス・プロプライエタリー・リミテッド	非晶質医薬組成物を用いる経皮送達速度調節
US20070185122A1 (en) *	2003-05-28	2007-08-09	Christophe Revirron	Use of efletirizine for treating persistent allergic rhinitis
WO2006050909A1 (fr) *	2004-11-10	2006-05-18	Ucb Farchim Sa	Nouvelles formes du dichlorhydrate d’efletirizine, procédés de synthèse desdites formes et préparations pharmaceutiques les incluant
WO2008155777A2 (fr) *	2007-06-18	2008-12-24	Cadila Healthcare Limited	Procédé de préparation de l'efletrizine
KR101006760B1 (ko) *	2008-07-17	2011-01-11	주식회사 진영테크	모터 순간 정전 복원 장치

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH505116A (it) *	1966-11-21	1971-03-31	Crc Ricerca Chim	Metodo per l'ottenimento di derivati della piperazina
SE409706B (sv) *	1976-05-21	1979-09-03	Astra Pharma Prod	Forfarande for framstellning av n,n-dimetyl-3-(4-bromfenyl)-3-3(3-pyridyl)-allylamin dihydroklorid monohydrat
FI75816C (fi)	1981-02-06	1988-08-08	Ucb Sa	Foerfarande foer framstaellning av terapeutiskt aktiv 2-/4-(difenylmetyl)-1-piperazinyl/-aettiksyror eller dess amid.
UA8337A1 (uk) *	1981-02-06	1996-03-29	Бальтес Ежен	2-[4-(дифенілметіл)-1-піперазиніл]-оцтові кислоти або їх аміди, або їх нетоксичні фармацевтично прийняті солі, що проявляють спазмолітичну і антигістамінну активність
GB8827391D0 (en) *	1988-11-23	1988-12-29	Ucb Sa	Process for preparation of 2-(2-(4-((4-chlorophenyl)phenylmethyl)-1-pipera-zinyl)ethoxy)-acetic acid & its dihydrochloride
GB8827390D0 (en) *	1988-11-23	1988-12-29	Ucb Sa	Process for preparation of 2-(2-(4-((4-chlorophenyl)phenylmethyl)-1-pipera-zinyl)ethoxy)-acetic acid & its dihydrochloride
US5968551A (en) *	1991-12-24	1999-10-19	Purdue Pharma L.P.	Orally administrable opioid formulations having extended duration of effect
TW401300B (en) *	1992-12-25	2000-08-11	Senju Pharma Co	Antiallergic composition for ophthalmic or nasal use
US5625358A (en) *	1993-09-13	1997-04-29	Analog Devices, Inc.	Digital phase-locked loop utilizing a high order sigma-delta modulator
BE1010095A3 (fr) *	1996-04-10	1997-12-02	Ucb Sa	Procede de preparation de l'acide 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl] ethoxy]-acetique et de ses sels.
BE1010094A3 (fr) *	1996-04-10	1997-12-02	Ucb Sa	Nouveaux [2-(1-piperazinyl)ethoxy] methyle substitues.

1997
- 1997-11-26 EP EP97870193A patent/EP0919550A1/fr not_active Withdrawn
1998
- 1998-11-17 MY MYPI98005218A patent/MY119653A/en unknown
- 1998-11-23 PE PE1998001137A patent/PE134899A1/es not_active Application Discontinuation
- 1998-11-24 CO CO98069203A patent/CO4980892A1/es unknown
- 1998-11-25 EG EG147698A patent/EG23776A/xx active
- 1998-11-25 TN TNTNSN98214A patent/TNSN98214A1/fr unknown
- 1998-11-25 ZA ZA9810780A patent/ZA9810780B/xx unknown
- 1998-11-25 AR ARP980105975A patent/AR017676A1/es not_active Application Discontinuation
- 1998-11-25 MA MA25361A patent/MA26569A1/fr unknown
- 1998-11-25 GC GCP199836 patent/GC0000094A/xx active
- 1998-11-26 CA CA002310318A patent/CA2310318C/fr not_active Expired - Fee Related
- 1998-11-26 PT PT80901733T patent/PT1034171E/pt unknown
- 1998-11-26 US US09/555,021 patent/US6262057B1/en not_active Expired - Fee Related
- 1998-11-26 PL PL340724A patent/PL190871B1/pl not_active IP Right Cessation
- 1998-11-26 DK DK98956725T patent/DK1034171T3/da active
- 1998-11-26 ES ES98956725T patent/ES2161552T3/es not_active Expired - Lifetime
- 1998-11-26 JP JP2000523202A patent/JP3996348B2/ja not_active Expired - Fee Related
- 1998-11-26 AT AT98956725T patent/ATE203237T1/de not_active IP Right Cessation
- 1998-11-26 NZ NZ504461A patent/NZ504461A/en unknown
- 1998-11-26 ID IDW20000985A patent/ID24964A/id unknown
- 1998-11-26 DE DE69801163T patent/DE69801163T2/de not_active Expired - Fee Related
- 1998-11-26 HU HU0100343A patent/HUP0100343A3/hu unknown
- 1998-11-26 CN CNB988114909A patent/CN100406448C/zh not_active Expired - Fee Related
- 1998-11-26 RS YUP-316/00A patent/RS49904B/sr unknown
- 1998-11-26 EP EP98956725A patent/EP1034171B1/fr not_active Expired - Lifetime
- 1998-11-26 SK SK594-2000A patent/SK283237B6/sk unknown
- 1998-11-26 WO PCT/BE1998/000184 patent/WO1999028310A1/fr not_active Ceased
- 1998-11-26 CZ CZ20001787A patent/CZ295972B6/cs not_active IP Right Cessation
- 1998-11-26 KR KR1020007005660A patent/KR100557711B1/ko not_active Expired - Fee Related
- 1998-11-26 AU AU13277/99A patent/AU735819B2/en not_active Ceased
- 1998-11-26 UA UA2000063689A patent/UA54568C2/uk unknown
- 1998-11-26 RU RU2000116106/04A patent/RU2182575C2/ru not_active IP Right Cessation
- 1998-11-26 SI SI9820072A patent/SI20325A/sl not_active IP Right Cessation
- 1998-11-26 BR BR9815405-2A patent/BR9815405A/pt not_active Application Discontinuation
- 1998-11-26 TR TR2000/01505T patent/TR200001505T2/xx unknown
- 1998-11-26 IL IL13554498A patent/IL135544A/en not_active IP Right Cessation
1999
- 1999-01-19 TW TW088100770A patent/TWI225053B/zh not_active IP Right Cessation
2000
- 2000-05-11 BG BG104424A patent/BG64155B1/bg unknown
- 2000-05-23 NO NO20002631A patent/NO314692B1/no unknown
2001
- 2001-03-08 US US09/800,665 patent/US6335331B2/en not_active Expired - Fee Related
- 2001-09-26 GR GR20010401559T patent/GR3036702T3/el not_active IP Right Cessation
2007
- 2007-04-18 JP JP2007109494A patent/JP2007224042A/ja active Pending

Also Published As

Publication number	Publication date
MY119653A (en)	2005-06-30
PT1034171E (pt)	2001-11-30
US20010021712A1 (en)	2001-09-13
ES2161552T3 (es)	2001-12-01
PL190871B1 (pl)	2006-02-28
EG23776A (en)	2007-08-08
ZA9810780B (en)	1999-05-31
JP2007224042A (ja)	2007-09-06
SI20325A (sl)	2001-02-28
JP2001524548A (ja)	2001-12-04
IL135544A0 (en)	2001-05-20
RU2182575C2 (ru)	2002-05-20
NO20002631L (no)	2000-05-23
NZ504461A (en)	2001-06-29
CN1279676A (zh)	2001-01-10
PL340724A1 (en)	2001-02-26
ATE203237T1 (de)	2001-08-15
TWI225053B (en)	2004-12-11
DE69801163D1 (en)	2001-08-23
CA2310318C (fr)	2003-10-21
CA2310318A1 (fr)	1999-06-10
EP1034171A1 (fr)	2000-09-13
US6262057B1 (en)	2001-07-17
KR100557711B1 (ko)	2006-03-07
TR200001505T2 (tr)	2000-09-21
BG64155B1 (bg)	2004-02-27
US6335331B2 (en)	2002-01-01
PE134899A1 (es)	2000-01-11
AR017676A1 (es)	2001-09-12
CZ295972B6 (cs)	2005-12-14
TNSN98214A1 (fr)	2005-03-15
JP3996348B2 (ja)	2007-10-24
BG104424A (en)	2001-01-31
HUP0100343A2 (hu)	2001-07-30
EP0919550A1 (fr)	1999-06-02
KR20010032420A (ko)	2001-04-16
NO20002631D0 (no)	2000-05-23
DE69801163T2 (de)	2002-03-28
BR9815405A (pt)	2000-10-10
DK1034171T3 (da)	2001-11-05
SK5942000A3 (en)	2000-10-09
AU735819B2 (en)	2001-07-19
GR3036702T3 (en)	2001-12-31
HUP0100343A3 (en)	2001-09-28
WO1999028310A1 (fr)	1999-06-10
EP1034171B1 (fr)	2001-07-18
SK283237B6 (sk)	2003-04-01
YU31600A (sh)	2002-03-18
RS49904B (sr)	2008-08-07
CO4980892A1 (es)	2000-11-27
CZ20001787A3 (cs)	2000-09-13
IL135544A (en)	2004-02-08
AU1327799A (en)	1999-06-16
MA26569A1 (fr)	2004-12-20
GC0000094A (en)	2005-06-29
ID24964A (id)	2000-08-31
UA54568C2 (uk)	2003-03-17
CN100406448C (zh)	2008-07-30

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