JP2012526045A5 - - Google Patents
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- Publication number
- JP2012526045A5 JP2012526045A5 JP2012507632A JP2012507632A JP2012526045A5 JP 2012526045 A5 JP2012526045 A5 JP 2012526045A5 JP 2012507632 A JP2012507632 A JP 2012507632A JP 2012507632 A JP2012507632 A JP 2012507632A JP 2012526045 A5 JP2012526045 A5 JP 2012526045A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- compound
- aryl
- substituted
- 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
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims 7
- -1 C1-C6 alkyl acetate Chemical compound 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 4
- 239000012320 chlorinating reagent Substances 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 150000003568 thioethers Chemical class 0.000 claims 2
- PTXVSDKCUJCCLC-UHFFFAOYSA-N 1-hydroxyindole Chemical compound C1=CC=C2N(O)C=CC2=C1 PTXVSDKCUJCCLC-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 1
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000012847 fine chemical Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 0 CC1(C)C=CC(N*)=C(C(*)(*)S*)C=C1 Chemical compound CC1(C)C=CC(N*)=C(C(*)(*)S*)C=C1 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09006050A EP2246326A1 (de) | 2009-05-02 | 2009-05-02 | Verfahren zur Herstellung von Oxindolen und ortho-substituierten Anilinen und ihre Verwendung als Zwischenprodukte für Synthesen |
| EP090006050.0 | 2009-05-02 | ||
| PCT/EP2010/002566 WO2010127786A1 (de) | 2009-05-02 | 2010-04-27 | Verfahren zur herstellung von oxindolen und ortho-substituierten anilinen und ihre verwendung als zwischenprodukte für synthesen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012526045A JP2012526045A (ja) | 2012-10-25 |
| JP2012526045A5 true JP2012526045A5 (https=) | 2014-11-27 |
| JP5826167B2 JP5826167B2 (ja) | 2015-12-02 |
Family
ID=41050783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012507632A Active JP5826167B2 (ja) | 2009-05-02 | 2010-04-27 | オキシインドールおよびオルト置換されたアニリンを生成するための方法ならびに合成のための中間生成物としてのそれらの使用 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US8492590B2 (https=) |
| EP (2) | EP2246326A1 (https=) |
| JP (1) | JP5826167B2 (https=) |
| KR (2) | KR101782961B1 (https=) |
| CN (1) | CN102459163B (https=) |
| BR (1) | BRPI1015123B1 (https=) |
| DK (1) | DK2424835T3 (https=) |
| ES (1) | ES2548024T3 (https=) |
| IL (1) | IL216051A (https=) |
| MX (2) | MX2011011547A (https=) |
| TW (1) | TWI547473B (https=) |
| WO (1) | WO2010127786A1 (https=) |
| ZA (1) | ZA201108035B (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008037631A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| WO2012028162A1 (de) * | 2010-09-01 | 2012-03-08 | Bayer Cropscience Ag | Verfahren zur herstellung von oxindolen und ortho-substituierten anilinen und ihre verwendung als zwischenprodukte für synthesen |
| KR102057717B1 (ko) | 2012-09-17 | 2019-12-19 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 유동반응기에서 오르토 치환된 아닐린의 연속 제조방법 |
| EP3049405A4 (en) | 2013-09-26 | 2017-03-08 | Pharmakea Inc. | Autotaxin inhibitor compounds |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3972894A (en) * | 1973-04-27 | 1976-08-03 | The Ohio State University Research Foundation | Synthesis of oxindoles from anilines and β-thio carboxylic esters or amides |
| US4690943A (en) * | 1984-09-19 | 1987-09-01 | Pfizer Inc. | Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds |
| US5663431A (en) * | 1992-01-30 | 1997-09-02 | Sanofi | 1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| FR2708605A1 (fr) | 1993-07-30 | 1995-02-10 | Sanofi Sa | Dérivés du N-sulfonylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| DE19521355A1 (de) | 1995-06-12 | 1996-12-19 | Hoechst Schering Agrevo Gmbh | Sulfonamide, Verfahren zu deren Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| CA2340701C (en) * | 1998-08-20 | 2009-05-26 | Sumitomo Pharmaceuticals Co., Ltd. | Oxindole derivatives as growth hormone releasers |
| US7008940B1 (en) * | 1999-08-20 | 2006-03-07 | Takeda Pharmaceutical Company Limited | Dihydrobenzofuran derivatives, process for the preparing thereof and agents |
| US6906096B2 (en) * | 2002-06-28 | 2005-06-14 | Irm Llc | 4,7-Disubstituted indoles and methods of making |
| RU2006117635A (ru) * | 2003-10-24 | 2007-12-10 | Шеринг Акциенгезельшафт (De) | Производные индолинона и их применение для лечения патологических состояний, таких как злокачественное новообразование |
| WO2005107466A1 (en) * | 2004-05-12 | 2005-11-17 | Bayer Cropscience Gmbh | Plant growth regulation |
| US20080280891A1 (en) | 2006-06-27 | 2008-11-13 | Locus Pharmaceuticals, Inc. | Anti-cancer agents and uses thereof |
| JP4770826B2 (ja) | 2007-11-22 | 2011-09-14 | 大日本印刷株式会社 | ２−オキシインドール誘導体の製造法 |
-
2009
- 2009-05-02 EP EP09006050A patent/EP2246326A1/de not_active Withdrawn
-
2010
- 2010-04-27 DK DK10715721.6T patent/DK2424835T3/en active
- 2010-04-27 MX MX2011011547A patent/MX2011011547A/es active IP Right Grant
- 2010-04-27 CN CN201080030137.1A patent/CN102459163B/zh active Active
- 2010-04-27 EP EP10715721.6A patent/EP2424835B1/de active Active
- 2010-04-27 JP JP2012507632A patent/JP5826167B2/ja active Active
- 2010-04-27 KR KR1020117028793A patent/KR101782961B1/ko active Active
- 2010-04-27 BR BRPI1015123-0A patent/BRPI1015123B1/pt active IP Right Grant
- 2010-04-27 ES ES10715721.6T patent/ES2548024T3/es active Active
- 2010-04-27 WO PCT/EP2010/002566 patent/WO2010127786A1/de not_active Ceased
- 2010-04-27 MX MX2013013279A patent/MX367426B/es unknown
- 2010-04-27 KR KR1020177016800A patent/KR101862230B1/ko active Active
- 2010-04-28 US US12/769,302 patent/US8492590B2/en active Active
- 2010-04-29 TW TW099113608A patent/TWI547473B/zh active
-
2011
- 2011-10-30 IL IL216051A patent/IL216051A/en active IP Right Grant
- 2011-11-02 ZA ZA2011/08035A patent/ZA201108035B/en unknown
-
2013
- 2013-06-12 US US13/915,898 patent/US9242934B2/en active Active
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