CA1317300C - Procede pour la preparation d'acide 2-(2-¬4-¬(4-chlorophenyl)phenylmethyl|-1-piperazinyl| ethoxy) acetique et de son dichlorhydrate - Google Patents
Procede pour la preparation d'acide 2-(2-¬4-¬(4-chlorophenyl)phenylmethyl|-1-piperazinyl| ethoxy) acetique et de son dichlorhydrateInfo
- Publication number
- CA1317300C CA1317300C CA000614709A CA614709A CA1317300C CA 1317300 C CA1317300 C CA 1317300C CA 000614709 A CA000614709 A CA 000614709A CA 614709 A CA614709 A CA 614709A CA 1317300 C CA1317300 C CA 1317300C
- Authority
- CA
- Canada
- Prior art keywords
- chlorophenyl
- phenylmethyl
- piperazinyl
- ethoxy
- dihydrochloride
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 title description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 title description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 14
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 title description 9
- 239000002253 acid Substances 0.000 claims abstract description 23
- 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 claims abstract description 10
- 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 claims abstract description 7
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 13
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 3
- 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 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 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
- 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
- 230000015572 biosynthetic process Effects 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical group C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 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 4
- 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
- 150000003839 salts Chemical class 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 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
- 239000002904 solvent Substances 0.000 description 3
- GQFCLJZQECVTDO-UHFFFAOYSA-N 2-(2-chloroethoxy)acetonitrile Chemical compound ClCCOCC#N GQFCLJZQECVTDO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-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
- -1 alkali metal salt Chemical class 0.000 description 2
- 229960001803 cetirizine Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- WPYUCWSMVJJWFI-UHFFFAOYSA-N 2-ethoxyacetonitrile Chemical compound CCOCC#N WPYUCWSMVJJWFI-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 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
- 208000003251 Pruritus Diseases 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000003513 alkali Substances 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
- 230000000172 allergic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- GEAXLHPORCRESC-UHFFFAOYSA-N chlorocyclohexatriene Chemical class ClC1=CC=C=C[CH]1 GEAXLHPORCRESC-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 1
- 229960002195 perazine Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance 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
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 (2)
| 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 |
| GB8827391 | 1988-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1317300C true CA1317300C (fr) | 1993-05-04 |
Family
ID=10647347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000614709A Expired - Fee Related CA1317300C (fr) | 1988-11-23 | 1989-09-29 | Procede pour la preparation d'acide 2-(2-¬4-¬(4-chlorophenyl)phenylmethyl|-1-piperazinyl| ethoxy) acetique et de son dichlorhydrate |
Country Status (16)
| Country | Link |
|---|---|
| KR (1) | KR970009728B1 (fr) |
| AT (1) | AT398971B (fr) |
| CA (1) | CA1317300C (fr) |
| CY (1) | CY1671A (fr) |
| DK (1) | DK174543B1 (fr) |
| ES (1) | ES2021907A6 (fr) |
| FI (1) | FI91862C (fr) |
| GB (2) | GB8827391D0 (fr) |
| GR (1) | GR1000553B (fr) |
| HK (1) | HK95892A (fr) |
| HU (1) | HU205094B (fr) |
| NO (1) | NO172342C (fr) |
| PH (1) | PH25982A (fr) |
| PL (1) | PL161379B1 (fr) |
| PT (1) | PT92364B (fr) |
| SG (1) | SG89492G (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1072661C (zh) * | 1996-04-10 | 2001-10-10 | Ucb公司 | 新的取代[2－(1－哌嗪基)乙氧基]甲基化合物 |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2128556T3 (es) * | 1992-09-24 | 1999-05-16 | Sepracor Inc | Tratamiento transdermico de la urticaria usando (+)-cetirizina opticamente pura. |
| AU703690B2 (en) * | 1992-09-24 | 1999-04-01 | Sepracor, Inc. | Methods for treating allergic disorders using optically pure (+)cetirizine |
| ES2122042T3 (es) * | 1992-09-24 | 1998-12-16 | Sepracor Inc | Tratamiento de rinitis alergica y asma que emplea (-)cetirizina. |
| 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 |
| 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. |
| JP3476475B2 (ja) | 1997-06-04 | 2003-12-10 | 株式会社アズウェル | ピペラジンスルホンアミド誘導体およびその塩の製造方法 |
| EP0919550A1 (fr) * | 1997-11-26 | 1999-06-02 | Ucb, S.A. | Formes pseudopolymorphiques de l'acide 2-2-4-bis(4-fluorophényl)méthyl -1-pipérazinyl-éthoxy acétique 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 |
| US7381821B2 (en) | 2003-01-23 | 2008-06-03 | Ucb, S.A. | 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 |
| AU2006222298B2 (en) * | 2005-03-03 | 2011-02-24 | Ucb Farchim Sa | Pyroglutamate salts and their use in the optical resolution of intermediates for the synthesis of dextrocetirizine and levocetirizine |
| 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 |
| WO2008152650A1 (fr) | 2007-06-15 | 2008-12-18 | Symed Labs Limited | Procédé de préparation d'énantiomères lévogyres et dextrogyres sensiblement optiquement purs de cétirizine à l'aide de nouveaux intermédiaires |
| WO2009062036A2 (fr) * | 2007-11-09 | 2009-05-14 | Dr. Reddy's Laboratories Ltd. | Procédés de préparation de lévocétirizine et de ses sels pharmaceutiquement acceptables |
| US7989623B2 (en) | 2007-11-21 | 2011-08-02 | Synthon Bv | Process for making n-(diphenylmethyl)piperazines |
| ES2361343T3 (es) | 2007-11-21 | 2011-06-16 | Synthon B.V. | Procedimiento para obtener n-(difenilmetil)piperazinas. |
| WO2009147389A2 (fr) | 2008-06-02 | 2009-12-10 | Cipla Limited | Procédés de synthèse de lévocétirizine et intermédiaires pour une utilisation dans ceux-ci |
| WO2009150147A1 (fr) * | 2008-06-11 | 2009-12-17 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nouveau procédé pour la préparation de la lévocétirizine et de ses intermédiaires |
| 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 (fr) | 2008-09-17 | 2010-04-29 | Calyx Chemicals And Pharmaceuticals Pvt. Ltd. | Nouveau procédé aqueux pour la synthèse de diphénylméthylpipérazines substituées |
| WO2010107404A1 (fr) | 2009-03-16 | 2010-09-23 | Mahmut Bilgic | Combinaisons pharmaceutiques stables |
| 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 (fr) | 2011-01-27 | 2012-08-02 | Jubilant Life Sciences Limited | Procédé de préparation amélioré d'antihistaminiques faisant appel à un nouvel intermédiaire carbamate |
| 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/fr not_active Expired - Fee Related
- 1989-11-20 GR GR890100770A patent/GR1000553B/el not_active IP Right Cessation
- 1989-11-21 PT PT92364A patent/PT92364B/pt not_active IP Right Cessation
- 1989-11-21 GB GB8926243A patent/GB2225321B/en not_active Expired - Lifetime
- 1989-11-22 DK DK198905867A patent/DK174543B1/da not_active IP Right Cessation
- 1989-11-22 ES ES8903975A patent/ES2021907A6/es not_active Expired - Lifetime
- 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
- 1989-11-22 NO NO894651A patent/NO172342C/no not_active IP Right Cessation
- 1989-11-22 PL PL1989282410A patent/PL161379B1/pl unknown
- 1989-11-22 FI FI895564A patent/FI91862C/fi not_active IP Right Cessation
- 1989-11-23 PH PH39570A patent/PH25982A/en unknown
- 1989-11-23 KR KR1019890017040A patent/KR970009728B1/ko not_active Expired - Fee Related
-
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/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1072661C (zh) * | 1996-04-10 | 2001-10-10 | Ucb公司 | 新的取代[2－(1－哌嗪基)乙氧基]甲基化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| FI91862C (fi) | 1994-08-25 |
| GB2225321A (en) | 1990-05-30 |
| PT92364B (pt) | 1995-07-18 |
| GB2225321B (en) | 1992-04-08 |
| ATA266589A (de) | 1994-07-15 |
| AT398971B (de) | 1995-02-27 |
| KR900007825A (ko) | 1990-06-02 |
| HUT53627A (en) | 1990-11-28 |
| NO894651D0 (no) | 1989-11-22 |
| HK95892A (en) | 1992-12-11 |
| GB8926243D0 (en) | 1990-01-10 |
| DK586789D0 (da) | 1989-11-22 |
| FI91862B (fi) | 1994-05-13 |
| NO172342C (no) | 1993-07-07 |
| ES2021907A6 (es) | 1991-11-16 |
| HU205094B (en) | 1992-03-30 |
| NO894651L (no) | 1990-05-25 |
| NO172342B (no) | 1993-03-29 |
| FI895564A0 (fi) | 1989-11-22 |
| GR890100770A (en) | 1990-12-31 |
| KR970009728B1 (ko) | 1997-06-17 |
| CY1671A (en) | 1993-05-14 |
| PL161379B1 (pl) | 1993-06-30 |
| DK174543B1 (da) | 2003-05-19 |
| HU896131D0 (en) | 1990-02-28 |
| GB8827391D0 (en) | 1988-12-29 |
| SG89492G (en) | 1992-12-04 |
| DK586789A (da) | 1990-05-24 |
| PH25982A (en) | 1992-01-13 |
| PT92364A (pt) | 1990-05-31 |
| GR1000553B (el) | 1992-08-26 |
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