JP2015516959A5 - - Google Patents
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- JP2015516959A5 JP2015516959A5 JP2015503828A JP2015503828A JP2015516959A5 JP 2015516959 A5 JP2015516959 A5 JP 2015516959A5 JP 2015503828 A JP2015503828 A JP 2015503828A JP 2015503828 A JP2015503828 A JP 2015503828A JP 2015516959 A5 JP2015516959 A5 JP 2015516959A5
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- JP
- Japan
- Prior art keywords
- formula
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- group
- compound
- 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.)
- Granted
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- 238000000034 method Methods 0.000 claims description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- NTBIYBAYFBNTCD-UHFFFAOYSA-N dibenzoyl 2,3-dihydroxybutanedioate Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C(O)C(O)C(=O)OC(=O)C1=CC=CC=C1 NTBIYBAYFBNTCD-UHFFFAOYSA-N 0.000 claims description 5
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- -1 R 2 is H Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12162852 | 2012-04-02 | ||
| EP12162852.3 | 2012-04-02 | ||
| PCT/EP2013/056638 WO2013149926A1 (en) | 2012-04-02 | 2013-03-28 | Process for the manufacturing of ccr3 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015516959A JP2015516959A (ja) | 2015-06-18 |
| JP2015516959A5 true JP2015516959A5 (enExample) | 2016-05-26 |
| JP6255550B2 JP6255550B2 (ja) | 2018-01-10 |
Family
ID=47998462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015503828A Active JP6255550B2 (ja) | 2012-04-02 | 2013-03-28 | Ｃｃｒ３阻害薬の製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8680280B2 (enExample) |
| EP (1) | EP2834229B1 (enExample) |
| JP (1) | JP6255550B2 (enExample) |
| AR (1) | AR090566A1 (enExample) |
| DK (1) | DK2834229T3 (enExample) |
| ES (1) | ES2641862T3 (enExample) |
| TW (1) | TW201400474A (enExample) |
| UY (1) | UY34719A (enExample) |
| WO (1) | WO2013149926A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8278302B2 (en) | 2009-04-08 | 2012-10-02 | Boehringer Ingelheim International Gmbh | Substituted piperidines as CCR3 antagonists |
| UA109290C2 (uk) | 2010-10-07 | 2015-08-10 | Спільні кристали і солі інгібіторів ccr3 | |
| AR090566A1 (es) | 2012-04-02 | 2014-11-19 | Boehringer Ingelheim Int | Proceso para la produccion de inhibidores de crr |
| US10213421B2 (en) | 2012-04-04 | 2019-02-26 | Alkahest, Inc. | Pharmaceutical formulations comprising CCR3 antagonists |
| NZ757769A (en) | 2017-04-05 | 2025-10-31 | Alkahest Inc | Methods and compositions for treating retina-associated disease using ccr3-inhibitors |
| WO2018187503A1 (en) | 2017-04-05 | 2018-10-11 | Alkahest, Inc. | Methods and compositions for treating aging-associated impairments using ccr3-inhibitors |
| AU2019271122A1 (en) | 2018-05-15 | 2020-11-12 | Alkahest, Inc. | Treatment of aging-associated disease with modulators of leukotriene A4 hydrolase |
| US11957671B2 (en) | 2021-11-01 | 2024-04-16 | Alkahest, Inc. | Benzodioxane modulators of leukotriene A4 hydrolase (LTA4H) for prevention and treatment of aging-associated diseases |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7907121L (sv) | 1979-08-27 | 1981-02-28 | Astra Laekemedel Ab | Ftalimidinderivat |
| JP2807577B2 (ja) | 1990-06-15 | 1998-10-08 | エーザイ株式会社 | 環状アミド誘導体 |
| JPH08134041A (ja) * | 1994-11-10 | 1996-05-28 | Fuji Photo Film Co Ltd | ピラゾールアミド類の製造方法 |
| EP1047675A1 (en) | 1998-01-21 | 2000-11-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US6140349A (en) | 1998-02-02 | 2000-10-31 | Merck & Co., Inc. | Cyclic amine modulators of chemokine receptor activity |
| JP2002501898A (ja) | 1998-02-02 | 2002-01-22 | メルク エンド カムパニー インコーポレーテッド | ケモカイン受容体活性の環状アミン調節剤 |
| ES2324224T3 (es) | 2004-02-05 | 2009-08-03 | Schering Corporation | Derivados de piperidina que se pueden utilizar como antagonistas ccr3. |
| JP2006137718A (ja) | 2004-11-12 | 2006-06-01 | Astellas Pharma Inc | インドール若しくはインダゾール誘導体 |
| WO2006083390A2 (en) | 2004-12-07 | 2006-08-10 | Children's Hospital Medical Center | Eotaxin-3 in eosinophilic esophagitis |
| DOP2006000051A (es) * | 2005-02-24 | 2006-08-31 | Lilly Co Eli | Inhibidores de vegf-r2 y métodos |
| EP2059515A2 (en) | 2006-04-12 | 2009-05-20 | Pfizer Limited | Pyrrolidine derivatives as modulators of chemokine ccr5 receptors |
| GB0701992D0 (en) | 2007-02-02 | 2007-03-14 | 7Tm Pharma As | Grehlin Receptor Modulators |
| US8008092B2 (en) | 2007-10-09 | 2011-08-30 | University Of Kentucky Research Foundation | CCR3 inhibition for ocular angiogenesis and macular degeneration |
| TW201000446A (en) | 2008-05-30 | 2010-01-01 | Astrazeneca Ab | New compounds useful in pain therapy |
| US8278302B2 (en) | 2009-04-08 | 2012-10-02 | Boehringer Ingelheim International Gmbh | Substituted piperidines as CCR3 antagonists |
| UA109290C2 (uk) | 2010-10-07 | 2015-08-10 | Спільні кристали і солі інгібіторів ccr3 | |
| AR090566A1 (es) | 2012-04-02 | 2014-11-19 | Boehringer Ingelheim Int | Proceso para la produccion de inhibidores de crr |
| US20130261153A1 (en) | 2012-04-03 | 2013-10-03 | Boehringer Ingelheim International Gmbh | Use of ccr3-inhibitors |
| US10213421B2 (en) | 2012-04-04 | 2019-02-26 | Alkahest, Inc. | Pharmaceutical formulations comprising CCR3 antagonists |
-
2013
- 2013-03-27 AR ARP130101059A patent/AR090566A1/es unknown
- 2013-03-27 US US13/851,547 patent/US8680280B2/en active Active
- 2013-03-28 JP JP2015503828A patent/JP6255550B2/ja active Active
- 2013-03-28 DK DK13712567.0T patent/DK2834229T3/da active
- 2013-03-28 EP EP13712567.0A patent/EP2834229B1/en active Active
- 2013-03-28 WO PCT/EP2013/056638 patent/WO2013149926A1/en not_active Ceased
- 2013-03-28 ES ES13712567.0T patent/ES2641862T3/es active Active
- 2013-04-01 TW TW102111742A patent/TW201400474A/zh unknown
- 2013-04-02 UY UY0001034719A patent/UY34719A/es unknown
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