JP2018535223A5 - - Google Patents
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- Publication number
- JP2018535223A5 JP2018535223A5 JP2018526145A JP2018526145A JP2018535223A5 JP 2018535223 A5 JP2018535223 A5 JP 2018535223A5 JP 2018526145 A JP2018526145 A JP 2018526145A JP 2018526145 A JP2018526145 A JP 2018526145A JP 2018535223 A5 JP2018535223 A5 JP 2018535223A5
- Authority
- JP
- Japan
- Prior art keywords
- crystal
- molar ratio
- bilastin
- acid
- crystals
- 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.)
- Withdrawn
Links
- 239000013078 crystal Substances 0.000 claims 27
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 6
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 5
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 4
- 206010010741 Conjunctivitis Diseases 0.000 claims 4
- 208000026935 allergic disease Diseases 0.000 claims 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000001361 adipic acid Substances 0.000 claims 3
- 235000011037 adipic acid Nutrition 0.000 claims 3
- 235000010233 benzoic acid Nutrition 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 claims 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 208000024780 Urticaria Diseases 0.000 claims 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims 2
- 229940116298 l- malic acid Drugs 0.000 claims 2
- 235000011090 malic acid Nutrition 0.000 claims 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims 2
- 230000007935 neutral effect Effects 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 206010039083 rhinitis Diseases 0.000 claims 2
- 235000010199 sorbic acid Nutrition 0.000 claims 2
- 239000004334 sorbic acid Substances 0.000 claims 2
- 229940075582 sorbic acid Drugs 0.000 claims 2
- 239000001384 succinic acid Substances 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 229960000250 adipic acid Drugs 0.000 claims 1
- 229960004050 aminobenzoic acid Drugs 0.000 claims 1
- 229960004365 benzoic acid Drugs 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960001755 resorcinol Drugs 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000001238 wet grinding Methods 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15382577.3A EP3170817A1 (en) | 2015-11-20 | 2015-11-20 | Co-crystals of benzimidazole compounds |
| EP15382577.3 | 2015-11-20 | ||
| PCT/EP2016/078145 WO2017085258A1 (en) | 2015-11-20 | 2016-11-18 | Co-crystals of benzimidazole compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018535223A JP2018535223A (ja) | 2018-11-29 |
| JP2018535223A5 true JP2018535223A5 (enExample) | 2019-06-27 |
Family
ID=54707731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018526145A Withdrawn JP2018535223A (ja) | 2015-11-20 | 2016-11-18 | ベンズイミダゾール化合物の共結晶 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20180319766A1 (enExample) |
| EP (2) | EP3170817A1 (enExample) |
| JP (1) | JP2018535223A (enExample) |
| CN (1) | CN108290857A (enExample) |
| BR (1) | BR112018010276A2 (enExample) |
| CA (1) | CA3005387A1 (enExample) |
| EA (1) | EA201891168A1 (enExample) |
| ES (1) | ES2745080T3 (enExample) |
| MX (1) | MX2018006252A (enExample) |
| PT (1) | PT3377478T (enExample) |
| WO (1) | WO2017085258A1 (enExample) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2048109B1 (es) | 1992-07-20 | 1994-12-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados piperidicos del bencimidazol. |
| ES2124167B1 (es) | 1996-06-04 | 1999-09-16 | Espanola Prod Quimicos | Nuevos derivados del bencimidazol con actividad antihistaminica. |
| ATE347550T1 (de) * | 2002-04-19 | 2006-12-15 | Faes Farma Sa | Polymorph von 4-(2-(4-(1-(2-ethoxyethyl)-1h- benzimidazol-2-yl)-1-piperidinyl)ethyl)-alpha, alpha-dimethylbenzolessigsäure |
| WO2008054609A2 (en) * | 2006-10-04 | 2008-05-08 | The Regents Of The University Of Michigan | Dissolution and precipitation of cocrystals with ionizable components |
| TWI580442B (zh) * | 2011-10-19 | 2017-05-01 | 傑特大學 | 醫藥毫微懸浮物 |
| CN103351380B (zh) * | 2013-06-30 | 2019-01-22 | 北京万全德众医药生物技术有限公司 | 一种制备比拉斯汀的方法 |
| SK7066Y1 (sk) | 2014-01-29 | 2015-03-03 | Zentiva Ks | Kryštalický dihydrát bilastínu |
| CN103788062A (zh) | 2014-02-17 | 2014-05-14 | 北京博泽德润医药科技开发有限公司 | 一种比拉斯汀晶型及其制备方法 |
-
2015
- 2015-11-20 EP EP15382577.3A patent/EP3170817A1/en not_active Withdrawn
-
2016
- 2016-11-18 ES ES16797941T patent/ES2745080T3/es active Active
- 2016-11-18 MX MX2018006252A patent/MX2018006252A/es unknown
- 2016-11-18 US US15/775,831 patent/US20180319766A1/en not_active Abandoned
- 2016-11-18 CA CA3005387A patent/CA3005387A1/en not_active Abandoned
- 2016-11-18 BR BR112018010276A patent/BR112018010276A2/pt not_active Application Discontinuation
- 2016-11-18 CN CN201680067635.0A patent/CN108290857A/zh active Pending
- 2016-11-18 EA EA201891168A patent/EA201891168A1/ru unknown
- 2016-11-18 EP EP16797941.8A patent/EP3377478B1/en active Active
- 2016-11-18 JP JP2018526145A patent/JP2018535223A/ja not_active Withdrawn
- 2016-11-18 PT PT167979418T patent/PT3377478T/pt unknown
- 2016-11-18 WO PCT/EP2016/078145 patent/WO2017085258A1/en not_active Ceased
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