JP2013526573A5 - - Google Patents
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- Publication number
- JP2013526573A5 JP2013526573A5 JP2013511294A JP2013511294A JP2013526573A5 JP 2013526573 A5 JP2013526573 A5 JP 2013526573A5 JP 2013511294 A JP2013511294 A JP 2013511294A JP 2013511294 A JP2013511294 A JP 2013511294A JP 2013526573 A5 JP2013526573 A5 JP 2013526573A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- complex
- dichloromethane
- butanol
- 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
Links
- 238000000034 method Methods 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 30
- 239000002253 acid Substances 0.000 claims 15
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 9
- 239000002904 solvent Substances 0.000 claims 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 7
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- -1 EGDE Chemical compound 0.000 claims 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 6
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 6
- 229940011051 isopropyl acetate Drugs 0.000 claims 6
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 6
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000007844 bleaching agent Substances 0.000 claims 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims 3
- 229940043279 diisopropylamine Drugs 0.000 claims 3
- 238000001035 drying Methods 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- 239000008096 xylene Substances 0.000 claims 3
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 239000007854 depigmenting agent Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- NTEUNCALHORCCY-UHFFFAOYSA-N n,n-diethylethanamine;toluene Chemical compound CCN(CC)CC.CC1=CC=CC=C1 NTEUNCALHORCCY-UHFFFAOYSA-N 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 238000007670 refining Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- AEULIVPVIDOLIN-UHFFFAOYSA-N CC(C)C[n](c(ccc(Nc1ncccn1)c1)c1c1c2CN3)c1c(CCc1n[n](C)cc1-1)c-1c2C3=O Chemical compound CC(C)C[n](c(ccc(Nc1ncccn1)c1)c1c1c2CN3)c1c(CCc1n[n](C)cc1-1)c-1c2C3=O AEULIVPVIDOLIN-UHFFFAOYSA-N 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34583110P | 2010-05-18 | 2010-05-18 | |
| US61/345,831 | 2010-05-18 | ||
| PCT/US2011/036814 WO2011146488A1 (en) | 2010-05-18 | 2011-05-17 | Method for purifying a fused pyrrolocarbazole derivative |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015205469A Division JP2016074668A (ja) | 2010-05-18 | 2015-10-19 | 溶融ピロロカルバゾール誘導体を精製するための方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013526573A JP2013526573A (ja) | 2013-06-24 |
| JP2013526573A5 true JP2013526573A5 (enExample) | 2014-07-03 |
| JP5828594B2 JP5828594B2 (ja) | 2015-12-09 |
Family
ID=44168420
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013511294A Active JP5828594B2 (ja) | 2010-05-18 | 2011-05-17 | 溶融ピロロカルバゾール誘導体を精製するための方法 |
| JP2015205469A Pending JP2016074668A (ja) | 2010-05-18 | 2015-10-19 | 溶融ピロロカルバゾール誘導体を精製するための方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015205469A Pending JP2016074668A (ja) | 2010-05-18 | 2015-10-19 | 溶融ピロロカルバゾール誘導体を精製するための方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8884014B2 (enExample) |
| EP (1) | EP2571885B1 (enExample) |
| JP (2) | JP5828594B2 (enExample) |
| KR (1) | KR101815332B1 (enExample) |
| CN (1) | CN102958934B (enExample) |
| AU (1) | AU2011256264B2 (enExample) |
| BR (1) | BR112012029374B1 (enExample) |
| CA (1) | CA2799517C (enExample) |
| CL (1) | CL2012003208A1 (enExample) |
| EA (1) | EA021869B1 (enExample) |
| ES (1) | ES2530015T3 (enExample) |
| IL (2) | IL223016A0 (enExample) |
| MX (1) | MX2012013304A (enExample) |
| MY (1) | MY156830A (enExample) |
| NZ (1) | NZ604135A (enExample) |
| PH (1) | PH12012502250A1 (enExample) |
| SG (2) | SG185645A1 (enExample) |
| UA (1) | UA108498C2 (enExample) |
| WO (1) | WO2011146488A1 (enExample) |
| ZA (1) | ZA201209305B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR074374A1 (es) | 2008-11-19 | 2011-01-12 | Cephalon Inc | Formas de un compuesto de pirrolocarbazol fusionado, composiciones que las comprenden y su uso en el tratamiento de la angiogénesis y los tumores sólidos. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR200401316T4 (tr) * | 2000-09-29 | 2004-07-21 | Eli Lilly And Company | Proliferatif hastalıkları tedavi etmek için yöntemler ve bileşikler |
| US7169802B2 (en) * | 2003-12-23 | 2007-01-30 | Cephalon, Inc. | Fused pyrrolocarbazoles |
| JP2006241579A (ja) | 2005-03-07 | 2006-09-14 | Nippon Paint Co Ltd | 化成処理剤及び表面処理金属 |
| AR074374A1 (es) | 2008-11-19 | 2011-01-12 | Cephalon Inc | Formas de un compuesto de pirrolocarbazol fusionado, composiciones que las comprenden y su uso en el tratamiento de la angiogénesis y los tumores sólidos. |
-
2011
- 2011-05-17 JP JP2013511294A patent/JP5828594B2/ja active Active
- 2011-05-17 MX MX2012013304A patent/MX2012013304A/es active IP Right Grant
- 2011-05-17 KR KR1020127032917A patent/KR101815332B1/ko active Active
- 2011-05-17 AU AU2011256264A patent/AU2011256264B2/en active Active
- 2011-05-17 CA CA2799517A patent/CA2799517C/en active Active
- 2011-05-17 NZ NZ604135A patent/NZ604135A/en unknown
- 2011-05-17 SG SG2012084851A patent/SG185645A1/en unknown
- 2011-05-17 BR BR112012029374-5A patent/BR112012029374B1/pt active IP Right Grant
- 2011-05-17 PH PH1/2012/502250A patent/PH12012502250A1/en unknown
- 2011-05-17 MY MYPI2012004977A patent/MY156830A/en unknown
- 2011-05-17 CN CN201180024787.XA patent/CN102958934B/zh active Active
- 2011-05-17 SG SG10201503541WA patent/SG10201503541WA/en unknown
- 2011-05-17 UA UAA201214484A patent/UA108498C2/ru unknown
- 2011-05-17 EP EP11721691.1A patent/EP2571885B1/en active Active
- 2011-05-17 EA EA201291269A patent/EA021869B1/ru not_active IP Right Cessation
- 2011-05-17 ES ES11721691.1T patent/ES2530015T3/es active Active
- 2011-05-17 WO PCT/US2011/036814 patent/WO2011146488A1/en not_active Ceased
-
2012
- 2012-11-13 IL IL223016A patent/IL223016A0/en active IP Right Grant
- 2012-11-16 CL CL2012003208A patent/CL2012003208A1/es unknown
- 2012-11-16 US US13/678,886 patent/US8884014B2/en active Active
- 2012-12-07 ZA ZA2012/09305A patent/ZA201209305B/en unknown
-
2015
- 2015-10-19 JP JP2015205469A patent/JP2016074668A/ja active Pending
- 2015-10-22 IL IL242221A patent/IL242221B/en active IP Right Grant
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