BG64155B1 - Псевдополиморфни форми на 2-[2-[4-[бис(4-флуорофенил) метил]-1-пиперазинил]етокси]оцетна киселина дихидрохлорид - Google Patents
Псевдополиморфни форми на 2-[2-[4-[бис(4-флуорофенил) метил]-1-пиперазинил]етокси]оцетна киселина дихидрохлорид Download PDFInfo
- Publication number
- BG64155B1 BG64155B1 BG104424A BG10442400A BG64155B1 BG 64155 B1 BG64155 B1 BG 64155B1 BG 104424 A BG104424 A BG 104424A BG 10442400 A BG10442400 A BG 10442400A BG 64155 B1 BG64155 B1 BG 64155B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- methyl
- bis
- piperazinyl
- fluorophenyl
- ethoxy
- Prior art date
Links
- 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 title claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 21
- 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 15
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- 238000002441 X-ray diffraction Methods 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 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
- 238000010992 reflux Methods 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
- 238000013268 sustained release Methods 0.000 claims description 2
- 239000012730 sustained-release form Substances 0.000 claims description 2
- PDARKJJJMSJCNT-UHFFFAOYSA-N 2-[2-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]acetic acid;hydrate;dihydrochloride Chemical compound O.Cl.Cl.C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 PDARKJJJMSJCNT-UHFFFAOYSA-N 0.000 claims 4
- RDESAOZCEHZSHZ-UHFFFAOYSA-N acetic acid hydrate dihydrochloride Chemical compound O.Cl.Cl.C(C)(=O)O RDESAOZCEHZSHZ-UHFFFAOYSA-N 0.000 claims 2
- XINMLYUZZQEWHG-UHFFFAOYSA-N Cl.Cl.FC1=C(C=CC=C1)C(N1CCN(CC1)CCOCC(=O)O)C1=C(C=CC=C1)F Chemical compound Cl.Cl.FC1=C(C=CC=C1)C(N1CCN(CC1)CCOCC(=O)O)C1=C(C=CC=C1)F XINMLYUZZQEWHG-UHFFFAOYSA-N 0.000 abstract 1
- XDFMPAGQNFJOQE-UHFFFAOYSA-N O.Cl.Cl.FC1=CC=C(C=C1)C(C1=CC=C(C=C1)F)C1N(CCNC1)CCOCC(=O)O Chemical compound O.Cl.Cl.FC1=CC=C(C=C1)C(C1=CC=C(C=C1)F)C1N(CCNC1)CCOCC(=O)O XDFMPAGQNFJOQE-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000004090 dissolution Methods 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
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- 238000004458 analytical method Methods 0.000 description 7
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- 239000000843 powder Substances 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229950003420 efletirizine Drugs 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
- 229960002920 sorbitol Drugs 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 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 3
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 3
- 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
- 238000011002 quantification Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000001757 thermogravimetry curve Methods 0.000 description 3
- KFSCLHCSYZAFHU-UHFFFAOYSA-N 2-[2-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]acetamide;dihydrochloride Chemical compound Cl.Cl.C1CN(CCOCC(=O)N)CCN1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 KFSCLHCSYZAFHU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 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
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 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
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 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
- 229940124531 pharmaceutical excipient Drugs 0.000 description 2
- 239000012071 phase 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
- 238000012360 testing method Methods 0.000 description 2
- -1 1- [bis (4-fluorophenyl) methyl] piperazinyl Chemical group 0.000 description 1
- KQHRCXCLILUNBX-UHFFFAOYSA-N 2-(2-chloroethoxy)acetamide Chemical compound NC(=O)COCCCl KQHRCXCLILUNBX-UHFFFAOYSA-N 0.000 description 1
- 229910002016 Aerosil® 200 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
- 229920003084 Avicel® PH-102 Polymers 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
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- 229920003091 Methocel™ Polymers 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- DSFVQIUBODXRLL-UHFFFAOYSA-N acetamide;dihydrochloride Chemical compound Cl.Cl.CC(N)=O DSFVQIUBODXRLL-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 229960001803 cetirizine Drugs 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
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- 230000003111 delayed effect Effects 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 150000008640 diphenylmethylpiperazines Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
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- 239000002706 dry binder Substances 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
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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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97870193A EP0919550A1 (en) | 1997-11-26 | 1997-11-26 | Pseudopolymorphic forms of 2-2-4-bis(4-fluorophenyl)methyl-1-piperazinyl-ethoxy acetic acid dihydrochloride |
| PCT/BE1998/000184 WO1999028310A1 (en) | 1997-11-26 | 1998-11-26 | Pseudopolymorphic forms of 2-[2-[4-[bis (4-fluorophenyl) methyl]-1-piperazinyl] ethoxy]acetic acid dihydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG104424A BG104424A (en) | 2001-01-31 |
| BG64155B1 true BG64155B1 (bg) | 2004-02-27 |
Family
ID=8231072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG104424A BG64155B1 (bg) | 1997-11-26 | 2000-05-11 | Псевдополиморфни форми на 2-[2-[4-[бис(4-флуорофенил) метил]-1-пиперазинил]етокси]оцетна киселина дихидрохлорид |
Country Status (39)
| Country | Link |
|---|---|
| US (2) | US6262057B1 (cs) |
| EP (2) | EP0919550A1 (cs) |
| JP (2) | JP3996348B2 (cs) |
| KR (1) | KR100557711B1 (cs) |
| CN (1) | CN100406448C (cs) |
| AR (1) | AR017676A1 (cs) |
| AT (1) | ATE203237T1 (cs) |
| AU (1) | AU735819B2 (cs) |
| BG (1) | BG64155B1 (cs) |
| BR (1) | BR9815405A (cs) |
| CA (1) | CA2310318C (cs) |
| CO (1) | CO4980892A1 (cs) |
| CZ (1) | CZ295972B6 (cs) |
| DE (1) | DE69801163T2 (cs) |
| DK (1) | DK1034171T3 (cs) |
| EG (1) | EG23776A (cs) |
| ES (1) | ES2161552T3 (cs) |
| GC (1) | GC0000094A (cs) |
| GR (1) | GR3036702T3 (cs) |
| HU (1) | HUP0100343A3 (cs) |
| ID (1) | ID24964A (cs) |
| IL (1) | IL135544A (cs) |
| MA (1) | MA26569A1 (cs) |
| MY (1) | MY119653A (cs) |
| NO (1) | NO314692B1 (cs) |
| NZ (1) | NZ504461A (cs) |
| PE (1) | PE134899A1 (cs) |
| PL (1) | PL190871B1 (cs) |
| PT (1) | PT1034171E (cs) |
| RS (1) | RS49904B (cs) |
| RU (1) | RU2182575C2 (cs) |
| SI (1) | SI20325A (cs) |
| SK (1) | SK283237B6 (cs) |
| TN (1) | TNSN98214A1 (cs) |
| TR (1) | TR200001505T2 (cs) |
| TW (1) | TWI225053B (cs) |
| UA (1) | UA54568C2 (cs) |
| WO (1) | WO1999028310A1 (cs) |
| ZA (1) | ZA9810780B (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002047689A2 (en) * | 2000-12-15 | 2002-06-20 | Ucb, S.A. | Use of cetirizine or efletirizine for preventing urticaria |
| EP1414460A1 (en) * | 2001-07-26 | 2004-05-06 | Ucb, S.A. | Process for the preparation of 2-(2-(4-(bis(4-fluorophenyl)methyl)-piperazin-1-yl)ethoxy)acetic acid derivatives or corresponding salt forms thereof and intermediates therefor |
| US20050181032A1 (en) * | 2002-06-25 | 2005-08-18 | Acrux Dds Pty Ltd. | Metastable pharmaceutical compositions |
| EP2266533A3 (en) * | 2002-06-25 | 2011-12-14 | Acrux DDS Pty Ltd | Transdermal delivery rate control using amorphous pharmaceutical compositions |
| JP2007500197A (ja) * | 2003-05-28 | 2007-01-11 | ユセベ ファルシム ソシエテ アノニム | 持続性アレルギー性鼻炎の治療のためのエフレチリジンの使用 |
| WO2006050909A1 (en) * | 2004-11-10 | 2006-05-18 | Ucb Farchim Sa | Novel forms of efletirizine dihydrochloride, processes for making them and pharmaceutical compositions including them |
| WO2008155777A2 (en) * | 2007-06-18 | 2008-12-24 | Cadila Healthcare Limited | Process for preparing efletrizine |
| KR101006760B1 (ko) * | 2008-07-17 | 2011-01-11 | 주식회사 진영테크 | 모터 순간 정전 복원 장치 |
Family Cites Families (11)
| 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 |
| NO155805C (no) * | 1981-02-06 | 1987-06-10 | Ucb Sa | Analogifremgangsmaate for fremstilling av terapeutisk virksomme 2-(4-(difenylmethyl)-1-piperazinyl)-eddiksyrer og deres amider og ikke-toksiske salter. |
| JPS57149282A (en) * | 1981-02-06 | 1982-09-14 | Ucb Sa | 2-(4-(diphenylmethyl)-1-piperazinyl)acetic acid and their derivatives as medicine |
| 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 |
| 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 |
| 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/en 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 AR ARP980105975A patent/AR017676A1/es not_active Application Discontinuation
- 1998-11-25 MA MA25361A patent/MA26569A1/fr unknown
- 1998-11-25 EG EG147698A patent/EG23776A/xx active
- 1998-11-25 ZA ZA9810780A patent/ZA9810780B/xx unknown
- 1998-11-25 GC GCP199836 patent/GC0000094A/xx active
- 1998-11-25 TN TNTNSN98214A patent/TNSN98214A1/fr unknown
- 1998-11-26 CA CA002310318A patent/CA2310318C/en not_active Expired - Fee Related
- 1998-11-26 AU AU13277/99A patent/AU735819B2/en not_active Ceased
- 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 SI SI9820072A patent/SI20325A/sl not_active IP Right Cessation
- 1998-11-26 ID IDW20000985A patent/ID24964A/id unknown
- 1998-11-26 DK DK98956725T patent/DK1034171T3/da active
- 1998-11-26 CZ CZ20001787A patent/CZ295972B6/cs not_active IP Right Cessation
- 1998-11-26 UA UA2000063689A patent/UA54568C2/uk unknown
- 1998-11-26 ES ES98956725T patent/ES2161552T3/es not_active Expired - Lifetime
- 1998-11-26 WO PCT/BE1998/000184 patent/WO1999028310A1/en active IP Right Grant
- 1998-11-26 NZ NZ504461A patent/NZ504461A/en unknown
- 1998-11-26 DE DE69801163T patent/DE69801163T2/de not_active Expired - Fee Related
- 1998-11-26 TR TR2000/01505T patent/TR200001505T2/xx unknown
- 1998-11-26 HU HU0100343A patent/HUP0100343A3/hu unknown
- 1998-11-26 RS YUP-316/00A patent/RS49904B/sr unknown
- 1998-11-26 CN CNB988114909A patent/CN100406448C/zh not_active Expired - Fee Related
- 1998-11-26 AT AT98956725T patent/ATE203237T1/de not_active IP Right Cessation
- 1998-11-26 RU RU2000116106/04A patent/RU2182575C2/ru not_active IP Right Cessation
- 1998-11-26 KR KR1020007005660A patent/KR100557711B1/ko not_active Expired - Fee Related
- 1998-11-26 SK SK594-2000A patent/SK283237B6/sk unknown
- 1998-11-26 JP JP2000523202A patent/JP3996348B2/ja not_active Expired - Fee Related
- 1998-11-26 EP EP98956725A patent/EP1034171B1/en not_active Expired - Lifetime
- 1998-11-26 IL IL13554498A patent/IL135544A/en not_active IP Right Cessation
- 1998-11-26 BR BR9815405-2A patent/BR9815405A/pt not_active Application Discontinuation
-
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
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