JP2007509991A5 - - Google Patents
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- Publication number
- JP2007509991A5 JP2007509991A5 JP2006538556A JP2006538556A JP2007509991A5 JP 2007509991 A5 JP2007509991 A5 JP 2007509991A5 JP 2006538556 A JP2006538556 A JP 2006538556A JP 2006538556 A JP2006538556 A JP 2006538556A JP 2007509991 A5 JP2007509991 A5 JP 2007509991A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- aliphatic
- alkyl
- independently
- 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 24
- 150000001875 compounds Chemical class 0.000 claims 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229910052725 zinc Inorganic materials 0.000 claims 3
- 239000011701 zinc Substances 0.000 claims 3
- 230000010933 acylation Effects 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 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 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229910052792 caesium Inorganic materials 0.000 claims 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 0 *C(c1c(C(O)O)[n]c(*)c1*)=* Chemical compound *C(c1c(C(O)O)[n]c(*)c1*)=* 0.000 description 6
- RIRARCHMRDHZAR-RNFRBKRXSA-N C[C@H]1[C@H](C)CCC1 Chemical compound C[C@H]1[C@H](C)CCC1 RIRARCHMRDHZAR-RNFRBKRXSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51528303P | 2003-10-28 | 2003-10-28 | |
| US60/515,283 | 2003-10-28 | ||
| PCT/US2004/037985 WO2005042484A1 (en) | 2003-10-28 | 2004-10-28 | Preparation of 4,5-dialkyl-3-acyl-pyrrole-2-carboxylic acid derivatives by fischer-fink type synthesis and subsequent acylation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011131818A Division JP2011231117A (ja) | 2003-10-28 | 2011-06-14 | Ｆｉｓｃｈｅｒ−ｆｉｎｋ型合成および続くアシル化による４，５−ジアルキル−３−アシル−ピロール−２−カルボン酸誘導体の製造 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007509991A JP2007509991A (ja) | 2007-04-19 |
| JP2007509991A5 true JP2007509991A5 (enExample) | 2009-06-25 |
| JP4942485B2 JP4942485B2 (ja) | 2012-05-30 |
Family
ID=34549387
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006538556A Expired - Fee Related JP4942485B2 (ja) | 2003-10-28 | 2004-10-28 | Ｆｉｓｃｈｅｒ−ｆｉｎｋ型合成および続くアシル化による４，５−ジアルキル−３−アシル−ピロール−２−カルボン酸誘導体の製造 |
| JP2011131818A Pending JP2011231117A (ja) | 2003-10-28 | 2011-06-14 | Ｆｉｓｃｈｅｒ−ｆｉｎｋ型合成および続くアシル化による４，５−ジアルキル−３−アシル−ピロール−２−カルボン酸誘導体の製造 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011131818A Pending JP2011231117A (ja) | 2003-10-28 | 2011-06-14 | Ｆｉｓｃｈｅｒ−ｆｉｎｋ型合成および続くアシル化による４，５−ジアルキル−３−アシル−ピロール−２−カルボン酸誘導体の製造 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US7250520B2 (enExample) |
| EP (1) | EP1678134B1 (enExample) |
| JP (2) | JP4942485B2 (enExample) |
| KR (1) | KR20060122872A (enExample) |
| CN (1) | CN1894211A (enExample) |
| AT (1) | ATE442355T1 (enExample) |
| AU (1) | AU2004285972A1 (enExample) |
| DE (1) | DE602004023105D1 (enExample) |
| ES (1) | ES2330944T3 (enExample) |
| IL (1) | IL175253A0 (enExample) |
| WO (1) | WO2005042484A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA79749C2 (en) | 1996-10-18 | 2007-07-25 | Vertex Pharma | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| TWI359147B (en) | 2003-09-05 | 2012-03-01 | Vertex Pharma | Inhibitors of serine proteases, particularly hcv n |
| US8399615B2 (en) | 2005-08-19 | 2013-03-19 | Vertex Pharmaceuticals Incorporated | Processes and intermediates |
| AR055395A1 (es) | 2005-08-26 | 2007-08-22 | Vertex Pharma | Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c |
| US7964624B1 (en) | 2005-08-26 | 2011-06-21 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
| AU2007217355B2 (en) | 2006-02-27 | 2012-06-21 | Vertex Pharmaceuticals Incorporated | Co-crystals comprising VX-950 and pharmaceutical compositions comprising the same |
| EP2194039A1 (en) | 2006-03-16 | 2010-06-09 | Vertex Pharmceuticals Incorporated | Process for preparing optically enriched compounds |
| CA2679312A1 (en) | 2007-02-27 | 2008-09-04 | Vertex Pharmaceuticals Incorporated | Co-crystals and pharmaceutical compositions comprising the same |
| CN101903392A (zh) | 2007-02-27 | 2010-12-01 | 弗特克斯药品有限公司 | 丝氨酸蛋白酶的抑制剂 |
| WO2009032198A1 (en) | 2007-08-30 | 2009-03-12 | Vertex Pharmaceuticals Incorporated | Co-crystals and pharmaceutical compositions comprising the same |
| EP2489346A1 (en) | 2011-01-26 | 2012-08-22 | NanotecMARIN GmbH | Food supplement and injectable material for prophylaxis and therapy of osteoporosis and other bone diseases |
| JP2015053226A (ja) | 2013-09-09 | 2015-03-19 | タイコエレクトロニクスジャパン合同会社 | 電気コネクタの端子、及び電気コネクタ |
| US10207974B1 (en) | 2017-12-05 | 2019-02-19 | Chevron Phillips Chemical Company Lp | Synthesis of gamma dicarbonyl and pyrrole compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2481369C (en) | 2002-04-11 | 2012-07-10 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hepatitis c virus ns3 - ns4 protease |
| TW200510391A (en) * | 2003-04-11 | 2005-03-16 | Vertex Pharma | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
-
2004
- 2004-10-28 AT AT04796917T patent/ATE442355T1/de not_active IP Right Cessation
- 2004-10-28 AU AU2004285972A patent/AU2004285972A1/en not_active Abandoned
- 2004-10-28 JP JP2006538556A patent/JP4942485B2/ja not_active Expired - Fee Related
- 2004-10-28 EP EP04796917A patent/EP1678134B1/en not_active Expired - Lifetime
- 2004-10-28 KR KR1020067010241A patent/KR20060122872A/ko not_active Abandoned
- 2004-10-28 DE DE602004023105T patent/DE602004023105D1/de not_active Expired - Lifetime
- 2004-10-28 ES ES04796917T patent/ES2330944T3/es not_active Expired - Lifetime
- 2004-10-28 CN CNA2004800377619A patent/CN1894211A/zh active Pending
- 2004-10-28 WO PCT/US2004/037985 patent/WO2005042484A1/en not_active Ceased
- 2004-10-28 US US10/978,301 patent/US7250520B2/en not_active Expired - Fee Related
-
2006
- 2006-04-27 IL IL175253A patent/IL175253A0/en unknown
-
2007
- 2007-06-13 US US11/762,274 patent/US20080167480A1/en not_active Abandoned
-
2011
- 2011-06-14 JP JP2011131818A patent/JP2011231117A/ja active Pending
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