JP2009540008A5 - - Google Patents
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- Publication number
- JP2009540008A5 JP2009540008A5 JP2009515575A JP2009515575A JP2009540008A5 JP 2009540008 A5 JP2009540008 A5 JP 2009540008A5 JP 2009515575 A JP2009515575 A JP 2009515575A JP 2009515575 A JP2009515575 A JP 2009515575A JP 2009540008 A5 JP2009540008 A5 JP 2009540008A5
- Authority
- JP
- Japan
- Prior art keywords
- mixture
- methyl
- temperature
- substep
- phenyl
- 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 82
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 39
- 239000000203 mixture Substances 0.000 claims 36
- 238000003756 stirring Methods 0.000 claims 13
- 239000000725 suspension Substances 0.000 claims 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 12
- XVXVAVCOKYEXMZ-ZHACJKMWSA-N (e)-3-[4-[[2-(2-methyl-1h-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enoic acid Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(O)=O)C=C1 XVXVAVCOKYEXMZ-ZHACJKMWSA-N 0.000 claims 11
- CPVSLHQIPGTMLH-UHFFFAOYSA-N 2-(2-methyl-1h-indol-3-yl)ethanamine Chemical compound C1=CC=C2C(CCN)=C(C)NC2=C1 CPVSLHQIPGTMLH-UHFFFAOYSA-N 0.000 claims 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- 239000011541 reaction mixture Substances 0.000 claims 8
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 8
- 239000012279 sodium borohydride Substances 0.000 claims 8
- 239000000243 solution Substances 0.000 claims 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 7
- 238000010438 heat treatment Methods 0.000 claims 6
- 150000002466 imines Chemical class 0.000 claims 6
- 238000001816 cooling Methods 0.000 claims 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 4
- 238000001035 drying Methods 0.000 claims 4
- 239000000706 filtrate Substances 0.000 claims 4
- KVXMLLMZXPRPNG-VOTSOKGWSA-N methyl (e)-3-(4-formylphenyl)prop-2-enoate Chemical compound COC(=O)\C=C\C1=CC=C(C=O)C=C1 KVXMLLMZXPRPNG-VOTSOKGWSA-N 0.000 claims 4
- FPOHNWQLNRZRFC-ZHACJKMWSA-N panobinostat Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(=O)NO)C=C1 FPOHNWQLNRZRFC-ZHACJKMWSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 238000002156 mixing Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- -1 2-methyl-1H-indol-3-yl Chemical group 0.000 claims 2
- XVRIEWDDMODMGA-UHFFFAOYSA-N 5-chloropentan-2-one Chemical compound CC(=O)CCCCl XVRIEWDDMODMGA-UHFFFAOYSA-N 0.000 claims 2
- 239000012065 filter cake Substances 0.000 claims 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 2
- 229940067157 phenylhydrazine Drugs 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 238000010899 nucleation Methods 0.000 claims 1
- 238000010792 warming Methods 0.000 claims 1
- 230000033458 reproduction Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80452706P | 2006-06-12 | 2006-06-12 | |
| US60/804,527 | 2006-06-12 | ||
| US86787806P | 2006-11-30 | 2006-11-30 | |
| US60/867,878 | 2006-11-30 | ||
| PCT/US2007/070564 WO2007146718A2 (en) | 2006-06-12 | 2007-06-07 | Process for making n-hydroxy-3-[4-[[[2-(2-methyl-1h-indol-3-yl)ethyl]amino] methyl]phenyl]-2e-2-propenamide and starting materials therefor |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013222442A Division JP5809223B2 (ja) | 2006-06-12 | 2013-10-25 | Ｎ−ヒドロキシ−３−［４−［［［２−（２−メチル−１ｈ−インドール−３−イル）エチル］アミノ］メチル］フェニル］−２ｅ−２−プロペンアミドの製造方法およびその出発物質 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009540008A JP2009540008A (ja) | 2009-11-19 |
| JP2009540008A5 true JP2009540008A5 (cg-RX-API-DMAC7.html) | 2010-07-15 |
| JP5431926B2 JP5431926B2 (ja) | 2014-03-05 |
Family
ID=38832681
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009515575A Active JP5431926B2 (ja) | 2006-06-12 | 2007-06-07 | Ｎ−ヒドロキシ−３−［４−［［［２−（２−メチル−１ｈ−インドール−３−イル）エチル］アミノ］メチル］フェニル］−２ｅ−２−プロペンアミドの製造方法およびその出発物質 |
| JP2013222442A Active JP5809223B2 (ja) | 2006-06-12 | 2013-10-25 | Ｎ−ヒドロキシ−３−［４−［［［２−（２−メチル−１ｈ−インドール−３−イル）エチル］アミノ］メチル］フェニル］−２ｅ−２−プロペンアミドの製造方法およびその出発物質 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013222442A Active JP5809223B2 (ja) | 2006-06-12 | 2013-10-25 | Ｎ−ヒドロキシ−３−［４−［［［２−（２−メチル−１ｈ−インドール−３−イル）エチル］アミノ］メチル］フェニル］−２ｅ−２−プロペンアミドの製造方法およびその出発物質 |
Country Status (31)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT202000004075A1 (it) | 2020-02-27 | 2021-08-27 | Flamma Spa | Processo per la preparazione di panobinostat |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB146260A (en) | 1918-07-11 | 1921-08-11 | Elektro Osmose Ag | A process for preparing proteids charged with immune substances |
| GB8531612D0 (en) * | 1985-12-23 | 1986-02-05 | Beecham Wuelfing Gmbh & Co Kg | Compounds |
| PE20020354A1 (es) * | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| AU2002237261A1 (en) | 2001-01-09 | 2002-07-24 | Novartis Pharma Gmbh | Rapid method for screening compounds for in vivo activity |
| NZ544689A (en) | 2001-11-06 | 2007-08-31 | Novartis Ag | Cyclooxygenase-2 inhibitor/histone deacetylase inhibitor combination |
| AU2007257882B2 (en) * | 2006-06-12 | 2011-09-08 | Secura Bio Inc. | Process for making salts of N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide |
-
2007
- 2007-06-07 IN IN910DEN2015 patent/IN2015DN00910A/en unknown
- 2007-06-07 WO PCT/US2007/070564 patent/WO2007146718A2/en not_active Ceased
- 2007-06-07 CN CN2011100629486A patent/CN102167678B/zh active Active
- 2007-06-07 US US12/302,572 patent/US20090306405A1/en not_active Abandoned
- 2007-06-07 MX MX2008015898A patent/MX2008015898A/es active IP Right Grant
- 2007-06-07 CA CA2653657A patent/CA2653657C/en active Active
- 2007-06-07 CN CN2012103501544A patent/CN103086944A/zh active Pending
- 2007-06-07 MX MX2012002221A patent/MX366213B/es unknown
- 2007-06-07 KR KR20087030232A patent/KR101493530B1/ko not_active Expired - Fee Related
- 2007-06-07 KR KR1020147026120A patent/KR101540194B1/ko not_active Expired - Fee Related
- 2007-06-07 BR BRPI0712847-9A patent/BRPI0712847A2/pt not_active IP Right Cessation
- 2007-06-07 PL PL07784350T patent/PL2032533T3/pl unknown
- 2007-06-07 AU AU2007257883A patent/AU2007257883B2/en not_active Ceased
- 2007-06-07 CN CN2011100630820A patent/CN102174008A/zh active Pending
- 2007-06-07 EP EP07784350.6A patent/EP2032533B8/en active Active
- 2007-06-07 NZ NZ572707A patent/NZ572707A/en not_active IP Right Cessation
- 2007-06-07 ES ES11179043.2T patent/ES2553255T3/es active Active
- 2007-06-07 ES ES07784350T patent/ES2416286T3/es active Active
- 2007-06-07 PT PT77843506T patent/PT2032533E/pt unknown
- 2007-06-07 DK DK07784350.6T patent/DK2032533T3/da active
- 2007-06-07 RU RU2008151726/04A patent/RU2448090C2/ru active
- 2007-06-07 JP JP2009515575A patent/JP5431926B2/ja active Active
- 2007-06-07 EP EP11179043.2A patent/EP2394991B1/en active Active
- 2007-06-07 CN CNA2007800217257A patent/CN101466674A/zh active Pending
- 2007-06-07 HR HRP20130798TT patent/HRP20130798T1/hr unknown
- 2007-06-08 PE PE2011002097A patent/PE20120221A1/es active IP Right Grant
- 2007-06-08 AR ARP070102498A patent/AR061296A1/es unknown
- 2007-06-08 PE PE2007000720A patent/PE20080851A1/es active IP Right Grant
- 2007-06-11 TW TW096120985A patent/TWI395734B/zh not_active IP Right Cessation
- 2007-06-11 CL CL200701691A patent/CL2007001691A1/es unknown
- 2007-06-12 JO JO2007219A patent/JO2900B1/en active
-
2008
- 2008-11-06 ZA ZA200809490A patent/ZA200809490B/xx unknown
- 2008-11-10 IL IL195211A patent/IL195211A/en active IP Right Grant
- 2008-11-28 MY MYPI20084865A patent/MY147576A/en unknown
- 2008-12-05 TN TNP2008000507A patent/TNSN08507A1/en unknown
- 2008-12-10 GT GT200800282A patent/GT200800282A/es unknown
- 2008-12-12 EC EC2008008978A patent/ECSP088978A/es unknown
- 2008-12-12 MA MA31472A patent/MA30513B1/fr unknown
-
2009
- 2009-01-09 NO NO20090137A patent/NO341870B1/no not_active IP Right Cessation
-
2010
- 2010-09-13 CL CL2010000973A patent/CL2010000973A1/es unknown
-
2011
- 2011-09-23 US US13/243,001 patent/US8536346B2/en active Active
-
2013
- 2013-10-25 JP JP2013222442A patent/JP5809223B2/ja active Active
-
2014
- 2014-07-28 IL IL233836A patent/IL233836A/en active IP Right Grant
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