Title:
NEW BICYCLIC DERIVATIVES OF PYRIDINES, THEIR PREPARATION, OBTAINED NEW INTERMEDIATES, THEIR USE AS DRUG AND PHARMACEUTICAL COMPOSITION CONTAINING THEM
Document Type and Number:
Japanese Patent JP3535534
Kind Code:
B2
Abstract:
PURPOSE: To obtain new bicyclic derivs. of pyridines useful as antagonists to angiotensin II receptors.
CONSTITUTION: The bicyclic derivs. of pyridines are compds. of formula I [where one of A and B is N and the other is C; the dotted line makes the pyridinyl ring satd. or unsatd.; R is a 1-6C alkyl, 3-7C cycloalkyl or the like; R1 to R4 are each -(CH2)m1-S(O)m2-X-R14 (m1 is 0-4; m2 is 0-2; and X-R14 is amino, a 1-6C alkyl, phenyl or the like), H, a halogen, OH, 1-6C alkyl, aryl or the like; and Y is -Y1-B-Y2 (Y1 is a 5- or 6-membered monocyclic aryl, an 8- to 10-membered synthetic ring; B is a single bond, -CO-, -NH-CO- or the like; and Y2 is Y1, H, cyano or the like)], e.g. 2-butyl-3-[(2'-1H-tetrazol-5-yl)(1,1'- biphenyl)-4-yl-methyl]pyrazolo[1,5-a]pyridine-4-carboxylic acid. The compds. of the formula I are obtd. by allowing compds. of formula II [where R'1 to R'4 are (protected) R1 to R4] to react with compds. of formula III [where R' and Y' are (protected) R and Y].
More Like This:
| WO/2003/020729 | 4-THIOXO-4,7-DIHYDRO-THIENO[2,3-b]PYRIDINE-5-CARBOXAMIDES AS ANT IVIRAL AGENTS |
| WO/2005/009971 | QUINOLONE DERIVATIVE OR SALT THEREOF |
| WO/2018/159852 | CURCUMIN-CONTAINING MEDICINAL PREPARATION |
Inventors:
Corbier, Alain
Fortin, Michel
Guillaume, Jacques
Haesslein, Jean-luc
Vevert, Jean-paul
Fortin, Michel
Guillaume, Jacques
Haesslein, Jean-luc
Vevert, Jean-paul
Application Number:
JP3241093A
Publication Date:
June 07, 2004
Filing Date:
January 29, 1993
Export Citation:
Assignee:
Roussel, Uclaf
International Classes:
A61P9/10; A61P9/12; A61P11/06; A61P13/12; A61P15/00; A61P25/28; A61P27/06; A61P43/00; A61K31/435; C07D471/04; C07F3/06; (IPC1-7): C07D471/04; A61K31/435; A61P9/10; A61P11/06; A61P13/12; A61P15/00; A61P25/28; A61P27/06
Other References:
Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔｓ，１０２：１４９２６２
Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔｓ，１１２：７７０９７
Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔｓ，１１５：７１４７８
Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔｓ，８１：１３６１０５
Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔｓ，８６：５４６９
Ｅｌｌｉ Ｓ． Ｈａｎｄ， ｅｔ ａｌ．，Ｉｍｉｄａｚｏ［１，２−ａ］ｐｙｒｉｄｉｎｅｓ−Ｎｏｖｅｌ ｓｕｂｓｔｉｔｕｔｉｏｎ ｒｅａｃｔｉｏｎｓ．，Ｊ． Ｏｒｇ．Ｃｈｅｍ．，Ｖｏｌ．４１， Ｎｏ．２２，ｐ．３５４９−３５５６
Ｉｃｈｒｏ Ｙｏｋｏｅ， ｅｔ ａｌ．，１，３−ｄｉｐｏｌａｒ ｃｙｃｌｏａｄｄｉｔｉｏｎ ｒｅａｃｔｉｏｎ ｏｆ ｃｈｒｏｍｏｎｅｓ ａｎｄ ｃｏｕｍａｒｉｎ ｗｉｔｈ ｐｙｒｉｄｉｎｉｕｍ ｙｌｉｄｅｓ．，Ｈｅｔｅｒｏｃｙｌｅｓ，Ｖｏｌ．２３， Ｎｏ．６，ｐ．１３９５−１３９８
Ｋａｔｓｕｙａ Ａｗａｎｏ， ｅｔ ａｌ．，Ｓｙｎｔｈｅｓｉｓ ｏｆ ３−Ｓｕｂｓｔｉｔｕｔｅｄ ｐｙｒａｚｏｌｏ［１，５−ａ］ｐｙｒｉｄｉｎｅ ｄｅｒｉｖａｔｉｖｅｓ ｗｉｔｈ ｉｎｈｉｂｉｔｏｒｙ ａｃｔｉｖｉｔｙ ｏｎ・・・，Ｃｈｅｍ． Ｐｈａｒｍ． Ｂｕｌｌ．，Ｖｏｌ． ３４，ｐ．２８２８−２８３２
Ｋａｔｓｕｙａ Ａｗａｎｏ， ｅｔ ａｌ．，Ｓｙｎｔｈｅｓｉｓ ｏｆ ３−Ｓｕｂｓｔｉｔｕｔｅｄ ｐｙｒａｚｏｌｏ［１，５−ａ］ｐｙｒｉｄｉｎｅ ｄｅｒｉｖａｔｉｖｅｓ ｗｉｔｈ ｉｎｈｉｂｉｔｏｒｙ ａｃｔｉｖｉｔｙ ｏｎ・・・，Ｃｈｅｍ． Ｐｈａｒｍ． Ｂｕｌｌ．，Ｖｏｌ． ３４，ｐ．２８３３−２８３９
Ｋｌａｕｓ Ｂｕｒｇｅｒ， ｅｔ ａｌ．，Ｓｙｎｔｈｅｓｉｓ，ｐ．１９９−２０３
Ｍ． Ｋｏｍｕｒｏ， ｅｔ ａｌ．，Ｉｄｅｎｔｉｆｉｃａｔｉｏｎ ｏｆ ｕｒｉｎａｒｙ ｍｅｔａｂｏｌｉｔｅｓ ｏｆ ２−ｍｅｔｈｙｌ−３−（１，４，５，６−ｔｅｔｒａｈｙｄｒｏｎｉｃｏｔｉｎｏｙｌ）ｐｙｒａｚｏｌｏ［１，５−ａ］・・・，Ａｒｚｎｅｉｍ．−Ｆｏｒｓｃｈ． ／Ｄｒｕｇ ｒｅｓ．，Ｖｏｌ．４２， Ｎｏ．１，ｐ．４８−５５
Ｓａｍｕｅｌ Ｄａｎｉｓｈｅｆｓｋｙ， ｅｔ ａｌ．，Ｓｅｌｅｃｔｉｖｅ ｃａｒｂｏｎ−ｃａｒｂｏｎ ｂｏｎｄ ｆｏｒｍａｔｉｏｎ ｖｉａ ｔｒａｎｓｉｔｉｏｎ ｍｅｔａｌ ｃａｔａｌｙｓｉｓ．３．，Ｊ． Ｏｒｇ． Ｃｈｅｍ．，Ｖｏｌ．４２， Ｎｏ．１０，ｐ．１８２１−１８２３
Ｓｉｍｏｎａ Ｐｏｄｅｒｇａｊｓ， ｅｔ ａｌ．，Ａ ｎｅｗ ｓｙｎｔｈｅｓｉｓ ｏｆ ｆｕｓｅｄ ｉｍｉｄａｚｏｌｅｓ： ｔｈｅ ｓｙｎｔｈｅｓｉｓ ｏｆ ３−ａｃｙｌ−ｓｕｂｓｔｉｔｕｔｅｄ ｉｍｉｄａｚｏ［１，２−ｘ］ａｚｉｎｅｓ．，Ｓｙｎｔｈｅｓｉｓ，ｐ．２６３−２６５
Ｙａｓｕｙｏｓｈｉ Ｍｉｋｉ， ｅｔ ａｌ．，Ａｃｉｄ−ｃａｔａｌｙｚｅｄ ｒｅａｃｔｉｏｎｓ ｏｆ ３−（ｈｙｄｒｏｘｙｍｅｔｈｙｌ）− ａｎｄ ３−（１− ｈｙｄｒｏｘｙｍｅｔｈｙｌ）− ａｎｄ ３−（１− ｈｙｄｒｏｘｙｍｅｔｈｙｌ）ｐｙｒａｚｏｌｏ［１，５−ａ］Ｐｙｒｉｄｉｎｅｓ，Ｊ． Ｈｅｔｅｒｏｃｙｃｌ． Ｃｈｅｍ．，Ｖｏｌ．２６，ｐ．１７３９−１７４５
Ｙｏｓｈｉｏ Ｎａｇａｔｓｕ， ｅｔ ａｌ．，Ｓｙｎｔｈｅｉｓ ｏｆ ｃａｒｂｏｎ−１４ ａｎｄ ｄｅｕｔｅｒｉｕｍ ｌａｂｅｌｅｄ ３−ｉｓｏｂｕｔｙｒｙｌ−２−ｉｓｏｐｒｏｐｙｌｐｙｒａｚｏｌｏ［１，５−ａ］ｐｙｒｉｄｉｎｅ．，Ｊｏｕｒｎａｌ ｏｆ ｌａｂｅｌｅｄ ｃｏｍｐｏｕｎｄｓ ａｎｄ ｒａｄｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｖｏｌ．２２， Ｎｏ．７，ｐ．７３５−７４３
Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔｓ，１１２：７７０９７
Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔｓ，１１５：７１４７８
Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔｓ，８１：１３６１０５
Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔｓ，８６：５４６９
Ｅｌｌｉ Ｓ． Ｈａｎｄ， ｅｔ ａｌ．，Ｉｍｉｄａｚｏ［１，２−ａ］ｐｙｒｉｄｉｎｅｓ−Ｎｏｖｅｌ ｓｕｂｓｔｉｔｕｔｉｏｎ ｒｅａｃｔｉｏｎｓ．，Ｊ． Ｏｒｇ．Ｃｈｅｍ．，Ｖｏｌ．４１， Ｎｏ．２２，ｐ．３５４９−３５５６
Ｉｃｈｒｏ Ｙｏｋｏｅ， ｅｔ ａｌ．，１，３−ｄｉｐｏｌａｒ ｃｙｃｌｏａｄｄｉｔｉｏｎ ｒｅａｃｔｉｏｎ ｏｆ ｃｈｒｏｍｏｎｅｓ ａｎｄ ｃｏｕｍａｒｉｎ ｗｉｔｈ ｐｙｒｉｄｉｎｉｕｍ ｙｌｉｄｅｓ．，Ｈｅｔｅｒｏｃｙｌｅｓ，Ｖｏｌ．２３， Ｎｏ．６，ｐ．１３９５−１３９８
Ｋａｔｓｕｙａ Ａｗａｎｏ， ｅｔ ａｌ．，Ｓｙｎｔｈｅｓｉｓ ｏｆ ３−Ｓｕｂｓｔｉｔｕｔｅｄ ｐｙｒａｚｏｌｏ［１，５−ａ］ｐｙｒｉｄｉｎｅ ｄｅｒｉｖａｔｉｖｅｓ ｗｉｔｈ ｉｎｈｉｂｉｔｏｒｙ ａｃｔｉｖｉｔｙ ｏｎ・・・，Ｃｈｅｍ． Ｐｈａｒｍ． Ｂｕｌｌ．，Ｖｏｌ． ３４，ｐ．２８２８−２８３２
Ｋａｔｓｕｙａ Ａｗａｎｏ， ｅｔ ａｌ．，Ｓｙｎｔｈｅｓｉｓ ｏｆ ３−Ｓｕｂｓｔｉｔｕｔｅｄ ｐｙｒａｚｏｌｏ［１，５−ａ］ｐｙｒｉｄｉｎｅ ｄｅｒｉｖａｔｉｖｅｓ ｗｉｔｈ ｉｎｈｉｂｉｔｏｒｙ ａｃｔｉｖｉｔｙ ｏｎ・・・，Ｃｈｅｍ． Ｐｈａｒｍ． Ｂｕｌｌ．，Ｖｏｌ． ３４，ｐ．２８３３−２８３９
Ｋｌａｕｓ Ｂｕｒｇｅｒ， ｅｔ ａｌ．，Ｓｙｎｔｈｅｓｉｓ，ｐ．１９９−２０３
Ｍ． Ｋｏｍｕｒｏ， ｅｔ ａｌ．，Ｉｄｅｎｔｉｆｉｃａｔｉｏｎ ｏｆ ｕｒｉｎａｒｙ ｍｅｔａｂｏｌｉｔｅｓ ｏｆ ２−ｍｅｔｈｙｌ−３−（１，４，５，６−ｔｅｔｒａｈｙｄｒｏｎｉｃｏｔｉｎｏｙｌ）ｐｙｒａｚｏｌｏ［１，５−ａ］・・・，Ａｒｚｎｅｉｍ．−Ｆｏｒｓｃｈ． ／Ｄｒｕｇ ｒｅｓ．，Ｖｏｌ．４２， Ｎｏ．１，ｐ．４８−５５
Ｓａｍｕｅｌ Ｄａｎｉｓｈｅｆｓｋｙ， ｅｔ ａｌ．，Ｓｅｌｅｃｔｉｖｅ ｃａｒｂｏｎ−ｃａｒｂｏｎ ｂｏｎｄ ｆｏｒｍａｔｉｏｎ ｖｉａ ｔｒａｎｓｉｔｉｏｎ ｍｅｔａｌ ｃａｔａｌｙｓｉｓ．３．，Ｊ． Ｏｒｇ． Ｃｈｅｍ．，Ｖｏｌ．４２， Ｎｏ．１０，ｐ．１８２１−１８２３
Ｓｉｍｏｎａ Ｐｏｄｅｒｇａｊｓ， ｅｔ ａｌ．，Ａ ｎｅｗ ｓｙｎｔｈｅｓｉｓ ｏｆ ｆｕｓｅｄ ｉｍｉｄａｚｏｌｅｓ： ｔｈｅ ｓｙｎｔｈｅｓｉｓ ｏｆ ３−ａｃｙｌ−ｓｕｂｓｔｉｔｕｔｅｄ ｉｍｉｄａｚｏ［１，２−ｘ］ａｚｉｎｅｓ．，Ｓｙｎｔｈｅｓｉｓ，ｐ．２６３−２６５
Ｙａｓｕｙｏｓｈｉ Ｍｉｋｉ， ｅｔ ａｌ．，Ａｃｉｄ−ｃａｔａｌｙｚｅｄ ｒｅａｃｔｉｏｎｓ ｏｆ ３−（ｈｙｄｒｏｘｙｍｅｔｈｙｌ）− ａｎｄ ３−（１− ｈｙｄｒｏｘｙｍｅｔｈｙｌ）− ａｎｄ ３−（１− ｈｙｄｒｏｘｙｍｅｔｈｙｌ）ｐｙｒａｚｏｌｏ［１，５−ａ］Ｐｙｒｉｄｉｎｅｓ，Ｊ． Ｈｅｔｅｒｏｃｙｃｌ． Ｃｈｅｍ．，Ｖｏｌ．２６，ｐ．１７３９−１７４５
Ｙｏｓｈｉｏ Ｎａｇａｔｓｕ， ｅｔ ａｌ．，Ｓｙｎｔｈｅｉｓ ｏｆ ｃａｒｂｏｎ−１４ ａｎｄ ｄｅｕｔｅｒｉｕｍ ｌａｂｅｌｅｄ ３−ｉｓｏｂｕｔｙｒｙｌ−２−ｉｓｏｐｒｏｐｙｌｐｙｒａｚｏｌｏ［１，５−ａ］ｐｙｒｉｄｉｎｅ．，Ｊｏｕｒｎａｌ ｏｆ ｌａｂｅｌｅｄ ｃｏｍｐｏｕｎｄｓ ａｎｄ ｒａｄｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｖｏｌ．２２， Ｎｏ．７，ｐ．７３５−７４３
Attorney, Agent or Firm:
倉内 基弘 （外１名）