JP2011523659A5 - - Google Patents
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- Publication number
- JP2011523659A5 JP2011523659A5 JP2011512196A JP2011512196A JP2011523659A5 JP 2011523659 A5 JP2011523659 A5 JP 2011523659A5 JP 2011512196 A JP2011512196 A JP 2011512196A JP 2011512196 A JP2011512196 A JP 2011512196A JP 2011523659 A5 JP2011523659 A5 JP 2011523659A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- solvent
- base
- levocetirizine
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 9
- 239000002904 solvent Substances 0.000 claims 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 8
- ZKLPARSLTMPFCP-OAQYLSRUSA-N 2-[2-[4-[(R)-(4-chlorophenyl)-phenylmethyl]-1-piperazinyl]ethoxy]acetic acid Chemical compound C1CN(CCOCC(=O)O)CCN1[C@@H](C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-OAQYLSRUSA-N 0.000 claims 7
- 229960001508 levocetirizine Drugs 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 4
- 239000003223 protective agent Substances 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- -1 dimethoxytrityl Chemical group 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- MHXJETVNZPUVEN-UHFFFAOYSA-N 2-(2-chloroethoxy)acetic acid Chemical class OC(=O)COCCCl MHXJETVNZPUVEN-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 2
- 239000012351 deprotecting agent Substances 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- LOSXTWDYAWERDB-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-2,3-dimethoxybenzene Chemical compound COC1=CC=CC(C(Cl)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1OC LOSXTWDYAWERDB-UHFFFAOYSA-N 0.000 claims 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims 1
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 claims 1
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 claims 1
- KQHRCXCLILUNBX-UHFFFAOYSA-N 2-(2-chloroethoxy)acetamide Chemical group NC(=O)COCCCl KQHRCXCLILUNBX-UHFFFAOYSA-N 0.000 claims 1
- GQFCLJZQECVTDO-UHFFFAOYSA-N 2-(2-chloroethoxy)acetonitrile Chemical compound ClCCOCC#N GQFCLJZQECVTDO-UHFFFAOYSA-N 0.000 claims 1
- VIEULUYYQGUMIF-UHFFFAOYSA-N 2-chloroethyl ethaneperoxoate Chemical compound CC(=O)OOCCCl VIEULUYYQGUMIF-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims 1
- 229940073608 benzyl chloride Drugs 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004799 bromophenyl group Chemical group 0.000 claims 1
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 claims 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical group CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- QARBMVPHQWIHKH-KHWXYDKHSA-N methanesulfonyl chloride Chemical group C[35S](Cl)(=O)=O QARBMVPHQWIHKH-KHWXYDKHSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- MMEIYVXPSXIGET-UHFFFAOYSA-N n-benzyl-4-chloroaniline Chemical compound C1=CC(Cl)=CC=C1NCC1=CC=CC=C1 MMEIYVXPSXIGET-UHFFFAOYSA-N 0.000 claims 1
- BQIABQCJXBELMT-UHFFFAOYSA-N o-(4-chlorophenyl) chloromethanethioate Chemical compound ClC(=S)OC1=CC=C(Cl)C=C1 BQIABQCJXBELMT-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical class NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 0 *c1ccc(CN(CCOP)CCOP)cc1 Chemical compound *c1ccc(CN(CCOP)CCOP)cc1 0.000 description 4
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1173/MUM/2008 | 2008-06-02 | ||
| IN1173MU2008 | 2008-06-02 | ||
| PCT/GB2009/001385 WO2009147389A2 (en) | 2008-06-02 | 2009-06-02 | Processes for the synthesis of levocetirizine and intermediates for use therein |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011523659A JP2011523659A (ja) | 2011-08-18 |
| JP2011523659A5 true JP2011523659A5 (OSRAM) | 2012-07-19 |
Family
ID=41009315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011512196A Pending JP2011523659A (ja) | 2008-06-02 | 2009-06-02 | レボセチリジンの合成方法及びそれに使用する中間体 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8350031B2 (OSRAM) |
| EP (1) | EP2307392A2 (OSRAM) |
| JP (1) | JP2011523659A (OSRAM) |
| KR (1) | KR20110022635A (OSRAM) |
| CN (1) | CN102046612A (OSRAM) |
| AU (1) | AU2009254959B2 (OSRAM) |
| CA (1) | CA2724887A1 (OSRAM) |
| NZ (1) | NZ589492A (OSRAM) |
| WO (1) | WO2009147389A2 (OSRAM) |
| ZA (1) | ZA201008223B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2307392A2 (en) | 2008-06-02 | 2011-04-13 | Cipla Limited | Processes for the synthesis of levocetirizine and intermediates for use therein |
| CN103044356A (zh) * | 2011-10-13 | 2013-04-17 | 湖南九典制药有限公司 | 合成左西替利嗪的新方法及其关键中间体 |
| CN110988163B (zh) * | 2019-11-29 | 2022-04-19 | 重庆华邦胜凯制药有限公司 | 一种hplc法分离测定盐酸左西替利嗪及其基因毒性杂质e的方法 |
| 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 (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2792398A (en) * | 1954-12-03 | 1957-05-14 | Miles Lab | Piperazine derivatives |
| US3790606A (en) * | 1970-09-30 | 1974-02-05 | Diamond Shamrock Corp | Alkoxylated mannich compositions and derivatives thereof |
| NL7306771A (OSRAM) * | 1972-06-02 | 1973-12-04 | ||
| 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. |
| US4656182A (en) | 1983-12-06 | 1987-04-07 | Warner-Lambert Company | Substituted trans-1,2-diaminocyclohexyl amide compounds |
| 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 |
| GB9305282D0 (en) * | 1993-03-15 | 1993-05-05 | Ucb Sa | Enantiomers of 1-(4-chlorophenyl)phenylmethyl)-4-(4-methylphenyl)sulphonyl)piperazine |
| JP4416198B2 (ja) * | 1997-12-19 | 2010-02-17 | 武田薬品工業株式会社 | アニリド誘導体、その製造法および用途 |
| WO2000044723A1 (en) * | 1999-01-27 | 2000-08-03 | American Cyanamid Company | Alkynyl containing hydroxamic acid derivatives, their preparation and their use as matrix metalloproteinase (mmp) inhibitors/tnf-alpha converting enzyme (tace) inhibitors |
| AR035312A1 (es) * | 1999-01-27 | 2004-05-12 | Wyeth Corp | Compuestos de acido hidroxamico que contienen alquinilo como inhibidores de metaloproteinasa de matriz/tace, composicion farmaceutica que los comprenden y el uso de los mismos para la manufactura de un medicamento |
| US6762180B1 (en) * | 1999-10-13 | 2004-07-13 | Boehringer Ingelheim Pharma Kg | Substituted indolines which inhibit receptor tyrosine kinases |
| JP4044740B2 (ja) * | 2001-05-31 | 2008-02-06 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
| HU227074B1 (en) * | 2005-12-08 | 2010-06-28 | Egis Gyogyszergyar Nyrt | An optically active carbamic acid derivative, method for producing the same and use as a pharmaceutical intermediate |
| EP2307392A2 (en) | 2008-06-02 | 2011-04-13 | Cipla Limited | Processes for the synthesis of levocetirizine and intermediates for use therein |
-
2009
- 2009-06-02 EP EP09757761A patent/EP2307392A2/en not_active Withdrawn
- 2009-06-02 KR KR1020107029404A patent/KR20110022635A/ko not_active Ceased
- 2009-06-02 CA CA2724887A patent/CA2724887A1/en not_active Abandoned
- 2009-06-02 WO PCT/GB2009/001385 patent/WO2009147389A2/en not_active Ceased
- 2009-06-02 AU AU2009254959A patent/AU2009254959B2/en not_active Ceased
- 2009-06-02 NZ NZ589492A patent/NZ589492A/en not_active IP Right Cessation
- 2009-06-02 CN CN2009801206348A patent/CN102046612A/zh active Pending
- 2009-06-02 US US12/993,011 patent/US8350031B2/en not_active Expired - Fee Related
- 2009-06-02 JP JP2011512196A patent/JP2011523659A/ja active Pending
-
2010
- 2010-11-17 ZA ZA2010/08223A patent/ZA201008223B/en unknown
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