JP2013526498A5 - - Google Patents
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- JP2013526498A5 JP2013526498A5 JP2013509511A JP2013509511A JP2013526498A5 JP 2013526498 A5 JP2013526498 A5 JP 2013526498A5 JP 2013509511 A JP2013509511 A JP 2013509511A JP 2013509511 A JP2013509511 A JP 2013509511A JP 2013526498 A5 JP2013526498 A5 JP 2013526498A5
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- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- preparing
- alkyl
- 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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- 150000003839 salts Chemical class 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001340 alkali metals Chemical group 0.000 claims description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- -1 alkaline earth metal sulfite Chemical class 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 4
- 235000010265 sodium sulphite Nutrition 0.000 claims description 4
- QDPQGFCZJZJQQC-UHFFFAOYSA-M sodium;sulfuric acid;nitrite Chemical group [Na+].[O-]N=O.OS(O)(=O)=O QDPQGFCZJZJQQC-UHFFFAOYSA-M 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 17
- 238000004519 manufacturing process Methods 0.000 claims 11
- 239000011541 reaction mixture Substances 0.000 claims 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 239000002518 antifoaming agent Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- FUHHVNLQKJNWNW-UHFFFAOYSA-M sodium hydrogen sulfate sulfurothioic O-acid Chemical compound [Na+].OS(O)(=O)=O.OS([O-])(=O)=S FUHHVNLQKJNWNW-UHFFFAOYSA-M 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OSFQSHJZDRIDCY-UHFFFAOYSA-N 7-fluoro-1,3-dihydroindol-2-one;7-fluoro-3-methylsulfanyl-1,3-dihydroindol-2-one Chemical compound FC1=CC=CC2=C1NC(=O)C2.C1=CC=C(F)C2=C1C(SC)C(=O)N2 OSFQSHJZDRIDCY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite group Chemical group N(=O)[O-] IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 229940001474 sodium thiosulfate Drugs 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33294910P | 2010-05-10 | 2010-05-10 | |
| US61/332,949 | 2010-05-10 | ||
| EP10162381 | 2010-05-10 | ||
| EP10162381.7 | 2010-05-10 | ||
| PCT/EP2011/057276 WO2011141364A1 (de) | 2010-05-10 | 2011-05-06 | Verfahren zur herstellung von substituierten 1,3-dihydro-2h-indol-2-onen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013526498A JP2013526498A (ja) | 2013-06-24 |
| JP2013526498A5 true JP2013526498A5 (enExample) | 2015-09-17 |
| JP5815679B2 JP5815679B2 (ja) | 2015-11-17 |
Family
ID=42537445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013509511A Active JP5815679B2 (ja) | 2010-05-10 | 2011-05-06 | 置換された１，３−ジヒドロ−２ｈ−インドール−２−オンの調製方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8563749B2 (enExample) |
| EP (1) | EP2569283B1 (enExample) |
| JP (1) | JP5815679B2 (enExample) |
| KR (1) | KR101783471B1 (enExample) |
| CN (1) | CN102985406B (enExample) |
| BR (1) | BR112012028767B1 (enExample) |
| DK (1) | DK2569283T3 (enExample) |
| ES (1) | ES2523226T3 (enExample) |
| IL (1) | IL222929A (enExample) |
| MX (1) | MX2012012959A (enExample) |
| TW (1) | TWI499583B (enExample) |
| WO (1) | WO2011141364A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3643210A1 (de) | 2018-10-25 | 2020-04-29 | Jura Elektroapparate AG | Verfahren zum erzeugen eines kaffeegetränks in einem kaffeeautomaten |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160032A (en) * | 1973-11-21 | 1979-07-03 | Sandoz, Inc. | Oxindoles as sleep-inducers |
| US4503073A (en) * | 1981-01-07 | 1985-03-05 | A. H. Robins Company, Incorporated | 2-Amino-3-(alkylthiobenzoyl)-phenylacetic acids |
| FI80270C (fi) * | 1984-09-19 | 1990-05-10 | Pfizer | Foerfarande foer framstaellning av analgetiska och anti-inflammatoriska 1,3-diacyl-2-oxoindol-foereningar och mellanprodukter. |
| US5076835A (en) * | 1990-05-31 | 1991-12-31 | America Cyanamid Company | Aryloxyspiroalkylindolinone herbicides |
| US5124347A (en) * | 1991-07-31 | 1992-06-23 | Warner-Lambert Co. | 3-5-ditertiarybutylphenyl-4-hydroxymethylidene derivatives of 1,3-dihydro-2H-indole-2-ones as antiinflammatory agents |
| FR2708605A1 (fr) * | 1993-07-30 | 1995-02-10 | Sanofi Sa | Dérivés du N-sulfonylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
-
2011
- 2011-05-06 MX MX2012012959A patent/MX2012012959A/es active IP Right Grant
- 2011-05-06 KR KR1020127031887A patent/KR101783471B1/ko active Active
- 2011-05-06 BR BR112012028767-2A patent/BR112012028767B1/pt active IP Right Grant
- 2011-05-06 ES ES11717663.6T patent/ES2523226T3/es active Active
- 2011-05-06 DK DK11717663.6T patent/DK2569283T3/en active
- 2011-05-06 TW TW100115968A patent/TWI499583B/zh active
- 2011-05-06 CN CN201180034200.3A patent/CN102985406B/zh active Active
- 2011-05-06 JP JP2013509511A patent/JP5815679B2/ja active Active
- 2011-05-06 EP EP11717663.6A patent/EP2569283B1/de active Active
- 2011-05-06 WO PCT/EP2011/057276 patent/WO2011141364A1/de not_active Ceased
- 2011-05-09 US US13/103,673 patent/US8563749B2/en active Active
-
2012
- 2012-11-08 IL IL222929A patent/IL222929A/en active IP Right Grant
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