Claims
- 1. A compound selected from the group consisting of a compound of the formula ##STR156## wherein R.sub.b is n-butyl or butenyl, one of Z.sub.1, Z.sub.2 and Z.sub.3 is sulfur and the other two are .dbd.CH--, R.sub.1b and R.sub.2b are individually selected from the group consisting of hydrogen; halogen; --OH, --SH; alkoxy, alkyl and alkylthio of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms, carbocyclic aryl, carbocyclic aralkyl and carbocyclic aralkenyl with up to 6 alkyl and alkenyl carbon atoms, all the alkyl, alkenyl, alkynyl, alkylthio, aryl, aralkyl and aralkenyl unsubstituted or substituted with at least one member of the group consisting of halogen, --OH, --SH, alkoxy and alkylthio of 1 to 4 carbon atoms, acyl and acyloxy; carboxy and carboxy esterified with alkyl of 1 to 4 carbon atoms, Y.sub.1b is phenyl, B.sub.b is a single bond or ##STR157## and when B.sub.b is a single bond or ##STR158## Y.sub.2b is phenyl unsubstituted or substituted with carboxy, esterified carboxy tetrazolyl, tetrazolyl-methyl or tetrazolyl-carbamoyl, --SO.sub.2 --X.sub.b --R.sub.14b, X.sub.b is selected from the group consisting of a single bond, --NH--, --CO-- and ##STR159## and R.sub.14b is selected from the group consisting of methyl, ethyl, vinyl, allyl, pyridylmethyl, pyridylethyl, pyridyl, phenyl and benzyl and when B.sub.b is a single bond, Y.sub.2b is cyano or free carboxy, salified or carboxy esterified with alkyl of 1 to 4 carbon atoms with the proviso that at least one of R.sub.1b and R.sub.2b is --OH and their non-toxic pharmaceutically acceptable salts with acid and base.
- 2. A compound of claim 1 selected from the group consisting of 1,1-dimethylethyl 2-butyl-1-[2'-carboxy-(1,1'-biphenyl)-4-yl)-methyl]-6-hydroxy-1H-thienyl-(2,3-d)-imidazol-5-carboxylate and its addition salts.
- 3. A compound of claim 1 selected from the group consisting of 2-butyl-[(2'-carboxy-(1,1'-biphenyl)-4-yl)-methyl]-6-hydroxy-1H-thien-(2,3-d)-imidazole-5-carboxylic acid, 1,1-dimethylethyl 2-butyl-1-[(2'-(methoxycarbonyl)-(1,1'-biphenyl)-4-yl)-methyl]-1H-thieno-(4,5-b)-imidazole-6-carboxylate, 1,1-dimethylethyl 2-butyl-6-hydroxy-1-[(2'-(methoxycarbonyl)-(1,1'-biphenyl)-4-yl]-methyl-1H-thieno(4,5-b)-imidazole-5-carboxylate and 2-butyl-1-[)2'-carbonyl-1,1'-biphenyl)-4-yl)-methyl]-1H-thieno-(2,3-d)-imidazole-5-carboxylic acid.
- 4. Antagonistic angiotensin II receptor compositions comprising an antagonistically angiotensin II effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.
- 5. A composition of claim 4 selected from the group consisting of 1,1-dimethylethyl 2-butyl-1-[(2'-carboxyphenyl-)1,1'-biphenyl)-4-yl)-methyl]-6-hydroxy-1H-thienyl-(2,3-d)-imidazol-5-carboxylate and its addition salts.
- 6. A method of inducing angiotensin II receptor antagonistic activity in warm-blooded animals comprising administering to warm-blooded animals an amount of at least one compound of claim 1 sufficient to induce angiotensin II receptor antagonistic activity.
- 7. A method of claim 6 wherein the compound is selected from the group consisting of 1,1-dimethyl 2-butyl-1-[(2'-carboxy-(1,1'-biphenyl)-4-yl)-methyl]-6-hydroxy-1H-thienyl-(2,3d)-imidazol-5-carboxylate and its addition salts.
- 8. A method of claim 6 wherein the compound is selected from the group consisting of 2-butyl-[(2'-carboxy-(1,1'-biphenyl)-4-yl)-methyl]-6-hydroxy-1H-thien-(2,3-d)-imidazole-5-carboxylic acid, 1,1-dimethylethyl 2-butyl-1-[(2'-(methoxycarbonyl)-(1,1'-biphenyl)-4-yl)-methyl]-1H-thieno-(4,5-b)-imidazole-6-carboxylate, 1,1-dimethylethyl 2-butyl-6-hydroxy-1-[(2'-(methoxycarbonyl)-(1,1'-biphenyl)-4-yl]-methyl-1H-thieno(4,5-b)-imidazole-5-carboxylate and 2-butyl-1-[(2'-carbonyl-1,1'-biphenyl)-4-yl)-methyl]-1H-thieno-(2,3-d)-imidazole-5-carboxylic acid.
Priority Claims (2)
Number |
Date |
Country |
Kind |
90 67136 |
Jun 1990 |
FRX |
|
91 03032 |
Mar 1991 |
FRX |
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PRIOR APPLICATION
This application is a division of U.S. patent application Ser. No. 074,106, filed Jun. 9, 1993, now U.S. Pat. No. 5,389,634, which is a division of U.S. patent application Ser. No. 712,247, filed Jun. 7, 1991, now U.S. Pat. No. 5,338,756.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
5338756 |
Fortin et al. |
Aug 1994 |
|
5389634 |
Fortin et al. |
Feb 1995 |
|
Foreign Referenced Citations (2)
Number |
Date |
Country |
0483683 |
May 1992 |
EPX |
0518033 |
Dec 1992 |
EPX |
Divisions (2)
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Number |
Date |
Country |
Parent |
74106 |
Jun 1993 |
|
Parent |
712247 |
Jun 1991 |
|