SK283237B6 - Pseudopolymorfné formy dihydrochloridu kyseliny 2-[2-[4-[bis(4-fluórfenyl)metyl]-1-piperazinyl]etoxy]octovej, spôsob ich prípravy a farmaceutické kompozície s ich obsahom - Google Patents
Pseudopolymorfné formy dihydrochloridu kyseliny 2-[2-[4-[bis(4-fluórfenyl)metyl]-1-piperazinyl]etoxy]octovej, spôsob ich prípravy a farmaceutické kompozície s ich obsahom Download PDFInfo
- Publication number
- SK283237B6 SK283237B6 SK594-2000A SK5942000A SK283237B6 SK 283237 B6 SK283237 B6 SK 283237B6 SK 5942000 A SK5942000 A SK 5942000A SK 283237 B6 SK283237 B6 SK 283237B6
- Authority
- SK
- Slovakia
- Prior art keywords
- methyl
- piperazinyl
- fluorophenyl
- bis
- ethoxy
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 24
- 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 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- 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 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 22
- 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 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 238000002441 X-ray diffraction Methods 0.000 claims 2
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 229950003420 efletirizine Drugs 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 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 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 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
- 238000004090 dissolution Methods 0.000 description 8
- 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
- 229960002920 sorbitol Drugs 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 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 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
- 239000008187 granular material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000001757 thermogravimetry curve Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003993 interaction Effects 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940124531 pharmaceutical excipient Drugs 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
- 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
- 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
- 206010010744 Conjunctivitis allergic Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 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
- 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
- 239000011260 aqueous acid Substances 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229960001803 cetirizine Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000008640 diphenylmethylpiperazines Chemical class 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000002706 dry binder Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base 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
- 229960001340 histamine Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000010972 statistical evaluation Methods 0.000 description 1
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- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 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
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 |
|---|---|
| SK5942000A3 SK5942000A3 (en) | 2000-10-09 |
| SK283237B6 true SK283237B6 (sk) | 2003-04-01 |
Family
ID=8231072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK594-2000A SK283237B6 (sk) | 1997-11-26 | 1998-11-26 | Pseudopolymorfné formy dihydrochloridu kyseliny 2-[2-[4-[bis(4-fluórfenyl)metyl]-1-piperazinyl]etoxy]octovej, spôsob ich prípravy a farmaceutické kompozície s ich obsahom |
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
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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
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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
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2007
- 2007-04-18 JP JP2007109494A patent/JP2007224042A/ja active Pending
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