JP2013529687A5 - - Google Patents
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- JP2013529687A5 JP2013529687A5 JP2013518575A JP2013518575A JP2013529687A5 JP 2013529687 A5 JP2013529687 A5 JP 2013529687A5 JP 2013518575 A JP2013518575 A JP 2013518575A JP 2013518575 A JP2013518575 A JP 2013518575A JP 2013529687 A5 JP2013529687 A5 JP 2013529687A5
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- JP
- Japan
- Prior art keywords
- compound
- formula
- item
- solvent
- aryl
- 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.)
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- 238000000034 method Methods 0.000 claims description 105
- 150000001875 compounds Chemical class 0.000 claims description 101
- 239000002904 solvent Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 20
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 16
- 239000012458 free base Substances 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 16
- 150000002430 hydrocarbons Chemical class 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 230000001476 alcoholic effect Effects 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 206010003246 arthritis Diseases 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 208000026278 immune system disease Diseases 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 239000011343 solid material Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000009286 beneficial effect Effects 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 0 CCC(C(*)=C1)C(N2C*(*)COCC2)=CC(OC)=C1NC(NC1)=CC(NC(C=CC(C)(C)C=C2)=C2C(N*)=O)=C(C(F)(F)F)C1(C)*=C Chemical compound CCC(C(*)=C1)C(N2C*(*)COCC2)=CC(OC)=C1NC(NC1)=CC(NC(C=CC(C)(C)C=C2)=C2C(N*)=O)=C(C(F)(F)F)C1(C)*=C 0.000 description 2
- DZADIHSSWKMGIZ-UHFFFAOYSA-N CNC(c1cc(F)ccc1Nc1c(C(F)(F)F)cnc(Nc(ccc(N2CCOCC2)c2)c2OC)c1)=O Chemical compound CNC(c1cc(F)ccc1Nc1c(C(F)(F)F)cnc(Nc(ccc(N2CCOCC2)c2)c2OC)c1)=O DZADIHSSWKMGIZ-UHFFFAOYSA-N 0.000 description 2
- IGUBBWJDMLCRIK-UHFFFAOYSA-N CNC(c1ccccc1Nc1cc(Nc(ccc(N2CCOCC2)c2)c2OC)ncc1C(F)(F)F)=O Chemical compound CNC(c1ccccc1Nc1cc(Nc(ccc(N2CCOCC2)c2)c2OC)ncc1C(F)(F)F)=O IGUBBWJDMLCRIK-UHFFFAOYSA-N 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35994210P | 2010-06-30 | 2010-06-30 | |
| US61/359,942 | 2010-06-30 | ||
| PCT/US2011/042169 WO2012012139A1 (en) | 2010-06-30 | 2011-06-28 | Synthesis and use of kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013529687A JP2013529687A (ja) | 2013-07-22 |
| JP2013529687A5 true JP2013529687A5 (enExample) | 2014-08-14 |
| JP5923499B2 JP5923499B2 (ja) | 2016-05-24 |
Family
ID=45497129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013518575A Expired - Fee Related JP5923499B2 (ja) | 2010-06-30 | 2011-06-28 | キナーゼインヒビターの合成および使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9505719B2 (enExample) |
| EP (1) | EP2588476A4 (enExample) |
| JP (1) | JP5923499B2 (enExample) |
| CN (1) | CN103168037A (enExample) |
| AU (1) | AU2011280031B2 (enExample) |
| CA (1) | CA2803005A1 (enExample) |
| MX (1) | MX343894B (enExample) |
| NZ (1) | NZ604801A (enExample) |
| WO (1) | WO2012012139A1 (enExample) |
| ZA (1) | ZA201300012B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012110774A1 (en) | 2011-02-17 | 2012-08-23 | Cancer Therapeutics Crc Pty Limited | Selective fak inhibitors |
| DK2675793T3 (en) | 2011-02-17 | 2018-11-12 | Cancer Therapeutics Crc Pty Ltd | FAK INHIBITORS |
| WO2019117813A1 (en) * | 2017-12-15 | 2019-06-20 | National University Of Singapore | Focal adhesion kinase targeted therapeutics for the treatment of glaucoma and fibrosis |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656182A (en) * | 1983-12-06 | 1987-04-07 | Warner-Lambert Company | Substituted trans-1,2-diaminocyclohexyl amide compounds |
| US20040006005A1 (en) | 2002-07-02 | 2004-01-08 | Sanjay Bhanot | Use of integrin-linked kinase inhibitors for treating insulin resistance, hyperglycemia and diabetes |
| GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
| GB0004887D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| DE60137069D1 (de) | 2000-10-11 | 2009-01-29 | Cephalon Inc | Arzneizusammensetzungen enthaltend modafinilverbindungen |
| TW200409629A (en) * | 2002-06-27 | 2004-06-16 | Bristol Myers Squibb Co | 2,4-disubstituted-pyridine N-oxides useful as HIV reverse transcriptase inhibitors |
| US20080119515A1 (en) | 2003-03-10 | 2008-05-22 | M Arshad Siddiqui | Heterocyclic Kinase Inhibitors: Methods of Use and Synthesis |
| GT200500310A (es) | 2004-11-19 | 2006-06-19 | Compuestos organicos | |
| BRPI0607811B8 (pt) | 2005-02-18 | 2021-05-25 | Janssen R & D Ireland | derivados de óxido de pirimidina de 2-(4-cianofenilamino) inibidores de hiv, composição farmacêutica compreendendo os mesmos, processo para preparar a referida composição e uso |
| EP1959926A1 (en) | 2005-10-25 | 2008-08-27 | Abbott Laboratories | Formulation comprising a drug of low water solubility and method of use thereof |
| EP2012753A2 (en) * | 2006-04-28 | 2009-01-14 | Schering Corporation | Process for the precipitation and isolation of 6,6-dimethyl-3-aza-bicyclo [3.1.0]hexane-amide compounds by controlled precipitation and pharmaceutical formulations containing same |
| CN101495095B (zh) * | 2006-04-28 | 2013-05-29 | 默沙东公司 | 通过受控的沉淀来沉淀和分离6,6-二甲基-3-氮杂-双环[3.1.0]己烷-酰胺化合物的方法和含有其的药学制剂 |
| JP2009544617A (ja) | 2006-07-21 | 2009-12-17 | ノバルティス アクチエンゲゼルシャフト | ベンゾイミダゾリルピリジルエーテルの製剤 |
| ES2485040T3 (es) * | 2007-03-16 | 2014-08-12 | The Scripps Research Institute | Inhibidores de cinasa de adhesión focal |
| WO2009100176A2 (en) | 2008-02-07 | 2009-08-13 | Abbott Laboratories | Pharmaceutical dosage form for oral administration of tyrosine kinase inhibitor |
| WO2009105498A1 (en) * | 2008-02-19 | 2009-08-27 | Smithkline Beecham Corporation | Anilinopyridines as inhibitors of fak |
| MX2010014057A (es) * | 2008-06-17 | 2011-03-21 | Astrazeneca Ab | Compuestos de piridina. |
| WO2011019943A1 (en) | 2009-08-12 | 2011-02-17 | Poniard Pharmaceuticals, Inc. | Method of promoting apoptosis and inhibiting metastasis |
| WO2011133668A2 (en) | 2010-04-20 | 2011-10-27 | President And Fellows Of Harvard College | Methods and compositions for the treatment of cancer |
-
2011
- 2011-06-28 AU AU2011280031A patent/AU2011280031B2/en not_active Ceased
- 2011-06-28 MX MX2012014986A patent/MX343894B/es active IP Right Grant
- 2011-06-28 EP EP11810100.5A patent/EP2588476A4/en not_active Withdrawn
- 2011-06-28 CA CA2803005A patent/CA2803005A1/en not_active Abandoned
- 2011-06-28 NZ NZ60480111A patent/NZ604801A/en not_active IP Right Cessation
- 2011-06-28 CN CN2011800421749A patent/CN103168037A/zh active Pending
- 2011-06-28 JP JP2013518575A patent/JP5923499B2/ja not_active Expired - Fee Related
- 2011-06-28 WO PCT/US2011/042169 patent/WO2012012139A1/en not_active Ceased
-
2013
- 2013-01-02 ZA ZA2013/00012A patent/ZA201300012B/en unknown
- 2013-08-07 US US13/961,517 patent/US9505719B2/en not_active Expired - Fee Related
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