PH25982A - A process for the preparation of 2-(2-((4-chlorophenyl) phenyl-methyl)-1-piperazinyl) ethoxy) acetic acid and its dihydrochloride - Google Patents
A process for the preparation of 2-(2-((4-chlorophenyl) phenyl-methyl)-1-piperazinyl) ethoxy) acetic acid and its dihydrochloride Download PDFInfo
- Publication number
- PH25982A PH25982A PH39570A PH39570A PH25982A PH 25982 A PH25982 A PH 25982A PH 39570 A PH39570 A PH 39570A PH 39570 A PH39570 A PH 39570A PH 25982 A PH25982 A PH 25982A
- Authority
- PH
- Philippines
- Prior art keywords
- chlorophenyl
- phenylmethyl
- formula
- piperazinyl
- dihydrochloride
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 2-(2-((4-chlorophenyl) phenyl-methyl)-1-piperazinyl) ethoxy Chemical group 0.000 title description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 2
- WPYUCWSMVJJWFI-UHFFFAOYSA-N 2-ethoxyacetonitrile Chemical compound CCOCC#N WPYUCWSMVJJWFI-UHFFFAOYSA-N 0.000 claims 1
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 claims 1
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 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 9
- 238000003756 stirring Methods 0.000 description 9
- 239000002609 medium Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- GQFCLJZQECVTDO-UHFFFAOYSA-N 2-(2-chloroethoxy)acetonitrile Chemical compound ClCCOCC#N GQFCLJZQECVTDO-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229960001803 cetirizine Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- SBAKHIDRFYZRKO-UHFFFAOYSA-N 2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetonitrile Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCN(CCOCC#N)CC1 SBAKHIDRFYZRKO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- PGLIUCLTXOYQMV-UHFFFAOYSA-N Cetirizine hydrochloride Chemical compound Cl.Cl.C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 PGLIUCLTXOYQMV-UHFFFAOYSA-N 0.000 description 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 208000002205 allergic conjunctivitis Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 208000024998 atopic conjunctivitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- RDFIZBYHUOHTQI-UHFFFAOYSA-N methyl 2-(2-chloroethoxy)acetate Chemical compound COC(=O)COCCCl RDFIZBYHUOHTQI-UHFFFAOYSA-N 0.000 description 1
- BYCHNMFDSQCCDD-UHFFFAOYSA-N methyl 2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetate Chemical compound C1CN(CCOCC(=O)OC)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 BYCHNMFDSQCCDD-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888827391A GB8827391D0 (en) | 1988-11-23 | 1988-11-23 | Process for preparation of 2-(2-(4-((4-chlorophenyl)phenylmethyl)-1-pipera-zinyl)ethoxy)-acetic acid & its dihydrochloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH25982A true PH25982A (en) | 1992-01-13 |
Family
ID=10647347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH39570A PH25982A (en) | 1988-11-23 | 1989-11-23 | A process for the preparation of 2-(2-((4-chlorophenyl) phenyl-methyl)-1-piperazinyl) ethoxy) acetic acid and its dihydrochloride |
Country Status (16)
| Country | Link |
|---|---|
| KR (1) | KR970009728B1 (de) |
| AT (1) | AT398971B (de) |
| CA (1) | CA1317300C (de) |
| CY (1) | CY1671A (de) |
| DK (1) | DK174543B1 (de) |
| ES (1) | ES2021907A6 (de) |
| FI (1) | FI91862C (de) |
| GB (2) | GB8827391D0 (de) |
| GR (1) | GR1000553B (de) |
| HK (1) | HK95892A (de) |
| HU (1) | HU205094B (de) |
| NO (1) | NO172342C (de) |
| PH (1) | PH25982A (de) |
| PL (1) | PL161379B1 (de) |
| PT (1) | PT92364B (de) |
| SG (1) | SG89492G (de) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU703690B2 (en) * | 1992-09-24 | 1999-04-01 | Sepracor, Inc. | Methods for treating allergic disorders using optically pure (+)cetirizine |
| EP0885611A3 (de) * | 1992-09-24 | 1999-01-07 | Sepracor, Inc. | Verfahren und Zusammensetzungen zur Behandlung von allergischen Krankheiten unter Verwendung von optisch reinen (+) Cetirizin |
| EP0950412A3 (de) * | 1992-09-24 | 2001-05-16 | Sepracor, Inc. | Zusammensetzungen zur Behandlung von allergischen Krankheiten unter Verwendung von (-) Cetirizin |
| GB9305282D0 (en) * | 1993-03-15 | 1993-05-05 | Ucb Sa | Enantiomers of 1-(4-chlorophenyl)phenylmethyl)-4-(4-methylphenyl)sulphonyl)piperazine |
| US6469009B1 (en) | 1996-04-08 | 2002-10-22 | Ucb, S.A. | Pharmaceutical compositions for the treatment of rhinitis |
| BE1010094A3 (fr) * | 1996-04-10 | 1997-12-02 | Ucb Sa | Nouveaux [2-(1-piperazinyl)ethoxy] methyle substitues. |
| 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. |
| EP1020443B1 (de) | 1997-06-04 | 2003-09-10 | Azwell Inc. | Verfahren zur herstellung von piperazinsulfonamid-derivaten und ihren salzen |
| EP0919550A1 (de) * | 1997-11-26 | 1999-06-02 | Ucb, S.A. | Pseudopolymorphische Formen der 2-2-4-Bis(4-fluorophenyl)methyl-1-piperazinyl-ethoxyessigsäure Dihydrochloride |
| IL124195A (en) * | 1998-04-23 | 2000-08-31 | Chemagis Ltd | Process for the preparation of esters of 2-¬4-¬4-chlorophenyl¾phenylmethyl¾-1-piperazinyl¬ethoxy¾acetic acid |
| GR990100135A (el) * | 1999-04-22 | 2000-12-29 | Genepharm �.�. | Μεθοδος παρασκευης του 2-(2-[4-[4-χλωροφαινυλο)(φαινυλο)μεθυλο]πιπεραζινο]αιθοξυ) οξικου οξεος και του διυδροχλωρικου αλατος αυτου |
| JP2002249487A (ja) | 2001-02-22 | 2002-09-06 | Sumitomo Chem Co Ltd | ４−（ｔｅｒｔ−ブトキシカルボニル）ピペラジン誘導体、その光学活性な酸付加塩、それらの製造法、およびそれらを用いる光学活性な１−［（置換フェニル）フェニルメチル］ピペラジンの製造法。 |
| US6977301B1 (en) | 2001-05-29 | 2005-12-20 | Ucb, S.A. | Process for preparing (S) and (R)—2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide |
| US7199241B1 (en) | 2001-05-29 | 2007-04-03 | Ucb, S.A. | Process for preparing (S) and (R)-2-[4-(4-chlorobenzhydryl)piperazin-1-yl]-ethoxyacetamide |
| AU2004205494B2 (en) | 2003-01-23 | 2009-04-30 | Ucb Farchim Sa | Piperazine derivatives and their use as synthesis intermediates |
| KR100503443B1 (ko) | 2004-02-02 | 2005-07-22 | 한림제약(주) | 광학적으로 활성인 세티리진 또는 그의 염의 제조방법 |
| ES2326689T3 (es) * | 2005-03-03 | 2009-10-16 | Ucb Farchim, S.A. | Sales de piroglutamato y su uso en la resolucion optica de intermedios para la sintesis de dextrocetirizana y levocetirizana. |
| HU227325B1 (en) * | 2005-12-08 | 2011-03-28 | Egis Gyogyszergyar Nyrt | Process for the production of an intermediate of (dextro- and levo)- cetirizine |
| US8049011B2 (en) | 2007-03-12 | 2011-11-01 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Process for the preparation of levocetirizine and intermediates thereof |
| SI22489A (sl) * | 2007-03-12 | 2008-10-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nov postopek za pripravo levocetirizina in njegovih intermediatov |
| EP2167479B1 (de) | 2007-06-15 | 2013-09-11 | Symed Labs Limited | Verfahren zur herstellung von weitgehend optisch reinen levorotatorischen und dextrorotatorischen enantiomeren von cetirizin mittels neuer zwischenprodukte |
| WO2009062036A2 (en) * | 2007-11-09 | 2009-05-14 | Dr. Reddy's Laboratories Ltd. | Processes for preparing levocetirizine and pharmaceutically acceptable salts thereof |
| PL2062881T3 (pl) | 2007-11-21 | 2011-07-29 | Synthon Bv | Sposób wytwarzania N-(difenylometylo)piperazyn |
| US7989623B2 (en) | 2007-11-21 | 2011-08-02 | Synthon Bv | Process for making n-(diphenylmethyl)piperazines |
| AU2009254959B2 (en) | 2008-06-02 | 2014-01-30 | Cipla Limited | Processes for the synthesis of levocetirizine and intermediates for use therein |
| EP2297122B1 (de) * | 2008-06-11 | 2014-05-21 | KRKA, tovarna zdravil, d.d., Novo mesto | Neues verfahren zur herstellung von levocetirizin und zwischenprodukten davon |
| KR100998067B1 (ko) | 2008-09-08 | 2010-12-03 | 주식회사 삼오제약 | 비스(1-[(4-클로로페닐)페닐메틸]피페라진)-2,3-디벤조일 타르타르산 신규 중간체 염 및 이를 이용한 광학 활성적으로 순수한 1-[(4-클로로페닐)페닐메틸]피페라진을 분리하는 분리방법 |
| WO2010046908A2 (en) | 2008-09-17 | 2010-04-29 | Calyx Chemicals And Pharmaceuticals Pvt. Ltd. | Novel water based process for the preparation of substituted diphenylmethyl piperazines |
| WO2010107404A1 (en) | 2009-03-16 | 2010-09-23 | Mahmut Bilgic | Stable pharmaceutical combinations |
| TR201007652A2 (tr) | 2010-09-20 | 2012-04-24 | Bi̇lgi̇ç Mahmut | Sinerjik etki. |
| TR201009398A2 (tr) | 2010-11-11 | 2012-05-21 | Bi̇lgi̇ç Mahmut | Fiziksel özellikleri geliştirilmiş tablet formülasyonları |
| WO2012101475A1 (en) | 2011-01-27 | 2012-08-02 | Jubilant Life Sciences Limited | An improved process for the preparation of antihistaminic drugs via a novel carbamate intermediate |
| CN103044355A (zh) * | 2011-10-13 | 2013-04-17 | 湖南九典制药有限公司 | 合成左西替利嗪的关键中间体及其制备方法 |
| KR101418404B1 (ko) | 2012-01-06 | 2014-07-10 | 한미약품 주식회사 | 레보세티리진 또는 이의 약학적으로 허용가능한 염 및 몬테루카스트 또는 이의 약학적으로 허용가능한 염을 함유하는 안정한 경구투여용 약학 제제 |
| KR102226833B1 (ko) | 2013-06-28 | 2021-03-12 | 한미약품 주식회사 | 레보세티리진 및 몬테루카스트를 포함하는 안정성이 개선된 복합 과립 제형 |
| CN104045607B (zh) * | 2014-05-21 | 2016-04-13 | 丽珠医药集团股份有限公司 | 一种盐酸西替利嗪的纯化方法 |
| CN105924409B (zh) * | 2016-05-12 | 2019-01-08 | 浙江永宁药业股份有限公司 | 一种(r)-1-((2-氯苯基)-(苯基)-甲基)-哌嗪的拆分方法 |
| CN111205247B (zh) * | 2020-04-22 | 2020-08-14 | 湖南九典宏阳制药有限公司 | 左旋西替利嗪的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
-
1988
- 1988-11-23 GB GB888827391A patent/GB8827391D0/en active Pending
-
1989
- 1989-09-29 CA CA000614709A patent/CA1317300C/en not_active Expired - Fee Related
- 1989-11-20 GR GR890100770A patent/GR1000553B/el not_active IP Right Cessation
- 1989-11-21 GB GB8926243A patent/GB2225321B/en not_active Expired - Lifetime
- 1989-11-21 PT PT92364A patent/PT92364B/pt not_active IP Right Cessation
- 1989-11-22 FI FI895564A patent/FI91862C/fi not_active IP Right Cessation
- 1989-11-22 DK DK198905867A patent/DK174543B1/da not_active IP Right Cessation
- 1989-11-22 NO NO894651A patent/NO172342C/no not_active IP Right Cessation
- 1989-11-22 ES ES8903975A patent/ES2021907A6/es not_active Expired - Lifetime
- 1989-11-22 PL PL1989282410A patent/PL161379B1/pl unknown
- 1989-11-22 HU HU896131A patent/HU205094B/hu not_active IP Right Cessation
- 1989-11-22 AT AT0266589A patent/AT398971B/de not_active IP Right Cessation
- 1989-11-23 KR KR1019890017040A patent/KR970009728B1/ko not_active IP Right Cessation
- 1989-11-23 PH PH39570A patent/PH25982A/en unknown
-
1992
- 1992-09-05 SG SG894/92A patent/SG89492G/en unknown
- 1992-12-03 HK HK958/92A patent/HK95892A/xx not_active IP Right Cessation
-
1993
- 1993-05-14 CY CY1671A patent/CY1671A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR900007825A (ko) | 1990-06-02 |
| GR890100770A (en) | 1990-12-31 |
| DK174543B1 (da) | 2003-05-19 |
| NO894651D0 (no) | 1989-11-22 |
| FI895564A0 (fi) | 1989-11-22 |
| GR1000553B (el) | 1992-08-26 |
| FI91862B (fi) | 1994-05-13 |
| HK95892A (en) | 1992-12-11 |
| HU205094B (en) | 1992-03-30 |
| HUT53627A (en) | 1990-11-28 |
| SG89492G (en) | 1992-12-04 |
| GB2225321B (en) | 1992-04-08 |
| CA1317300C (en) | 1993-05-04 |
| GB8827391D0 (en) | 1988-12-29 |
| KR970009728B1 (ko) | 1997-06-17 |
| NO172342B (no) | 1993-03-29 |
| CY1671A (en) | 1993-05-14 |
| ATA266589A (de) | 1994-07-15 |
| PL161379B1 (pl) | 1993-06-30 |
| DK586789A (da) | 1990-05-24 |
| AT398971B (de) | 1995-02-27 |
| ES2021907A6 (es) | 1991-11-16 |
| DK586789D0 (da) | 1989-11-22 |
| PT92364A (pt) | 1990-05-31 |
| GB2225321A (en) | 1990-05-30 |
| FI91862C (fi) | 1994-08-25 |
| PT92364B (pt) | 1995-07-18 |
| HU896131D0 (en) | 1990-02-28 |
| NO172342C (no) | 1993-07-07 |
| GB8926243D0 (en) | 1990-01-10 |
| NO894651L (no) | 1990-05-25 |
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