JP2006520345A5 - - Google Patents
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- JP2006520345A5 JP2006520345A5 JP2006504568A JP2006504568A JP2006520345A5 JP 2006520345 A5 JP2006520345 A5 JP 2006520345A5 JP 2006504568 A JP2006504568 A JP 2006504568A JP 2006504568 A JP2006504568 A JP 2006504568A JP 2006520345 A5 JP2006520345 A5 JP 2006520345A5
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- JP
- Japan
- Prior art keywords
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- 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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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims 2
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 claims 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims 2
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 claims 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000003983 crown ethers Chemical class 0.000 claims 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 1
- IRMGVPILCPGYNQ-UHFFFAOYSA-M dimethyl-di(tetradecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCC IRMGVPILCPGYNQ-UHFFFAOYSA-M 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 239000003444 phase transfer catalyst Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 1
- 239000006104 solid solution Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 claims 1
- JBNCFFDGYDZEEN-UHFFFAOYSA-N N#CCC(Nc1ccc(C(F)(F)F)cc1)=O Chemical compound N#CCC(Nc1ccc(C(F)(F)F)cc1)=O JBNCFFDGYDZEEN-UHFFFAOYSA-N 0.000 description 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10311763A DE10311763A1 (de) | 2003-03-18 | 2003-03-18 | Verfahren zur Herstellung von 2-Cyan-3-hydroxy-N-(phenyl)but-2-enamiden |
| PCT/EP2004/002311 WO2004083165A1 (de) | 2003-03-18 | 2004-03-06 | Verfahren zur hertellung von 2-cyan-3-hydroxy-n-(phenyl)but-2-enamiden |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006520345A JP2006520345A (ja) | 2006-09-07 |
| JP2006520345A5 true JP2006520345A5 (enExample) | 2007-04-12 |
| JP4546952B2 JP4546952B2 (ja) | 2010-09-22 |
Family
ID=32945937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006504568A Expired - Lifetime JP4546952B2 (ja) | 2003-03-18 | 2004-03-06 | ２−シアノ−３−ヒドロキシ−ｎ−（フェニル）ブタ−２−エンアミドの製法 |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1606246B1 (enExample) |
| JP (1) | JP4546952B2 (enExample) |
| KR (1) | KR101072237B1 (enExample) |
| CN (1) | CN100361967C (enExample) |
| AR (1) | AR043624A1 (enExample) |
| AT (1) | ATE468323T1 (enExample) |
| AU (1) | AU2004222139B2 (enExample) |
| CA (1) | CA2519209C (enExample) |
| CY (1) | CY1110722T1 (enExample) |
| DE (2) | DE10311763A1 (enExample) |
| DK (1) | DK1606246T3 (enExample) |
| ES (1) | ES2346215T3 (enExample) |
| IL (1) | IL170934A (enExample) |
| MX (1) | MXPA05009764A (enExample) |
| PL (1) | PL1606246T3 (enExample) |
| PT (1) | PT1606246E (enExample) |
| RU (1) | RU2330838C2 (enExample) |
| SI (1) | SI1606246T1 (enExample) |
| TW (1) | TW200503995A (enExample) |
| WO (1) | WO2004083165A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009147624A2 (en) * | 2008-06-05 | 2009-12-10 | Alembic Limited | A process for preparing teriflunomide |
| IN2014DN07162A (enExample) * | 2012-01-28 | 2015-04-24 | Optmed Inc | |
| CN104995166A (zh) * | 2013-01-29 | 2015-10-21 | Opt迈德有限公司 | 改进的1,1-二取代的乙烯方法 |
| CN104693070A (zh) * | 2013-12-10 | 2015-06-10 | 深圳翰宇药业股份有限公司 | 一种特立氟胺的合成方法 |
| CN105272882B (zh) * | 2014-07-23 | 2019-05-31 | 欣凯医药化工中间体（上海）有限公司 | 一种环保简便制备泰瑞米特的方法 |
| CN116924937A (zh) * | 2022-04-02 | 2023-10-24 | 江苏康缘药业股份有限公司 | 2-氰基-3-羟基-2-丁烯-(4-三氟甲基-苯基)酰胺制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8619432D0 (en) * | 1986-08-08 | 1986-09-17 | Lilly Industries Ltd | Pharmaceutical compounds |
| US5700823A (en) * | 1994-01-07 | 1997-12-23 | Sugen, Inc. | Treatment of platelet derived growth factor related disorders such as cancers |
| US5519042A (en) * | 1994-01-13 | 1996-05-21 | Hoechst Aktiengesellschaft | Method of treating hyperproliferative vascular disease |
| DE19636974A1 (de) * | 1996-09-12 | 1998-03-19 | Hoechst Ag | 2-Cyano-3,5-dihydroxy-hex-2-en- carbonsäureamidderivate |
| AU2001236361A1 (en) * | 2000-10-20 | 2002-05-06 | Parker Hughes Institute | Treatment of asthma with lfm analogues |
-
2003
- 2003-03-18 DE DE10311763A patent/DE10311763A1/de not_active Withdrawn
-
2004
- 2004-03-06 DE DE502004011176T patent/DE502004011176D1/de not_active Expired - Lifetime
- 2004-03-06 RU RU2005132162/04A patent/RU2330838C2/ru active
- 2004-03-06 PL PL04718192T patent/PL1606246T3/pl unknown
- 2004-03-06 SI SI200431463T patent/SI1606246T1/sl unknown
- 2004-03-06 AU AU2004222139A patent/AU2004222139B2/en not_active Expired
- 2004-03-06 MX MXPA05009764A patent/MXPA05009764A/es active IP Right Grant
- 2004-03-06 ES ES04718192T patent/ES2346215T3/es not_active Expired - Lifetime
- 2004-03-06 CN CNB2004800058365A patent/CN100361967C/zh not_active Expired - Lifetime
- 2004-03-06 WO PCT/EP2004/002311 patent/WO2004083165A1/de not_active Ceased
- 2004-03-06 AT AT04718192T patent/ATE468323T1/de active
- 2004-03-06 KR KR1020057017413A patent/KR101072237B1/ko not_active Expired - Lifetime
- 2004-03-06 CA CA2519209A patent/CA2519209C/en not_active Expired - Fee Related
- 2004-03-06 PT PT04718192T patent/PT1606246E/pt unknown
- 2004-03-06 DK DK04718192.0T patent/DK1606246T3/da active
- 2004-03-06 JP JP2006504568A patent/JP4546952B2/ja not_active Expired - Lifetime
- 2004-03-06 EP EP04718192A patent/EP1606246B1/de not_active Expired - Lifetime
- 2004-03-16 TW TW093106897A patent/TW200503995A/zh unknown
- 2004-03-16 AR ARP040100868A patent/AR043624A1/es unknown
-
2005
- 2005-09-18 IL IL170934A patent/IL170934A/en active IP Right Grant
-
2010
- 2010-08-03 CY CY20101100723T patent/CY1110722T1/el unknown
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