Claims
- 1. A compound of the formula: ##STR20## or a pharmaceutically acceptable acid addition salt thereof, in which: R.sub.1 is phenyl, halophenyl, dihalophenyl, trihalophenyl, lower alkylphenyl, di-lower alkylphenyl, tri-lower alkylphenyl, lower alkoxyphenyl, di-lower alkoxyphenyl, tri-lower alkoxyphenyl, lower alkyl-di-lower alkoxyphenyl or lower alkoxy-di-lower alkylphenyl;
- R.sub.2 is hydrogen, halo, lower alkyl, lower alkoxy, nitro or trifluoromethyl; ##STR21## R.sub.4 is hydrogen, methyl, ethyl or propyl and R.sub.5 is methyl, ethyl or propyl or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a pyrrolidine, piperidine, N-(lower alkyl)piperazine, morpholine or perhydroazepine ring;
- R.sub.6 is hydrogen or hydroxy;
- m is 0 or 1 when R.sub.6 is hydrogen and 1 when R.sub.6 is hydroxy;
- n is 0 or 1; and
- Z is oxygen or sulfur.
- 2. A compound according to claim 1 in which Z is oxygen.
- 3. A compound according to claim 1 in which Z is sulphur.
- 4. A compound according to claim 2 in which R.sub.4 is hydrogen, methyl, ethyl or propyl and R.sub.5 is methyl, ethyl or propyl.
- 5. A compound according to claim 2 in which ##STR22## is in the 3-position of the benzofuran nucleus; R.sub.1 is dihalophenyl, trihalophenyl, di-lower alkylphenyl, tri-lower alkylphenyl, di-lower alkoxyphenyl, tri-lower alkoxyphenyl, lower alkyl-di-lower alkoxyphenyl or lower alkoxy-di-lower alkylphenyl; R.sub.2 is hydrogen, halo or lower alkyl; --(CH.sub.2).sub.n R.sub.3 is in the 2-position of the benzofuran nucleus; R.sub.3 is ##STR23## R.sub.4 and R.sub.5 are methyl, ethyl, propyl or together with the nitrogen atom to which they are attached form a pyrrolidine, piperidine, N-(lower alkyl)piperazine, morpholine or perhydroazepine ring and R.sub.6 is hydrogen.
- 6. A compound according to claim 2 in which ##STR24## is in the 3-position of the benzofuran nucleus; R.sub.1 is halophenyl, 3,5-dihalophenyl, 3,5-di-lower alkylphenyl, 3,4,5-tri-lower alkylphenyl, 3,5-di-lower alkoxyphenyl or 3,5-di-lower alkyl-4-lower alkoxyphenyl; R.sub.2 is hydrogen or halo; --(CH.sub.2).sub.n R.sub.3 is in the 2-position of the benzofuran nucleus; R.sub.3 is ##STR25## R.sub.4 and R.sub.5 are methyl, ethyl, propyl or together with the nitrogen atom to which they are attached form a pyrrolidine, piperidine, N-(lower alkyl)piperazine, morpholine or perhydroazepine ring and R.sub.6 is hydrogen.
- 7. A compound according to claim 6 in which R.sub.1 is chlorophenyl, 3,5-dimethylphenyl, 3,4,5-trimethylphenyl, 3,5-dimethoxyphenyl or 3,5-dimethyl-4-methoxyphenyl; R.sub.2 is hydrogen or chloro; n is 0; R.sub.3 is ##STR26## R.sub.4 and R.sub.5 are ethyl or together with the nitrogen atom to which they are attached form a pyrrolidine or piperidine ring and m is 0.
- 8. A compound according to claim 7 in which R.sub.4 and R.sub.5 are ethyl.
- 9. A compound according to claim 4 being the compound 2-(4'-chlorobenzoyl)-3-[4'-(2-hydroxy-3-isopropylaminopropoxy)phenyl]benzofuran.
- 10. A compound according to claim 7 being the compound 3-(3',5'-dimethylbenzoyl)-2-[4'-(2-pyrrolidinoethoxy)phenyl]benzofuran.
- 11. A compound according to claim 7 being the compound 3-(3',5'-dimethylbenzoyl)-2-[4'-(2-N-piperidinoethoxy)phenyl]benzofuran.
- 12. A compound according to claim 8 being the compound 2-[4'-(2-diethylaminoethoxy)phenyl]-3-(3',5'-dimethylbenzoyl)benzofuran.
- 13. A compound according to claim 8 being the compound 2-[4'-(2-diethylaminoethoxy)phenyl]-3-(3',4',5'-trimethylbenzoyl)benzofuran.
- 14. A compound according to claim 8 being the compound 5-chloro-2-[4'-(2-diethylaminoethoxy)phenyl]-3-(3',5'-dimethylbenzoyl)benzofuran.
- 15. A compound according to claim 8 being the compound 3-[4'-(2-diethylaminoethoxy)phenyl]-2-(3',5'-dimethylbenzoyl)benzofuran.
- 16. A compound according to claim 8 being the compound 2-[4'-(2-diethylaminoethoxy)phenyl]-3-(3',5'-diethylbenzoyl)benzofuran.
- 17. A compound according to claim 3 being the compound 2-[4'-(2-diethylaminoethoxy)phenyl]-3-(3',5'-dimethylbenzoyl)benzothiophene.
- 18. A compound according to claim 3 being the compound 5-chloro-2-[4'-(2-diethylaminoethoxy)phenyl]-3-(3',5'-dimethylbenzoyl)benzothiophene.
- 19. A compound according to claim 3 being the compound 3-[4'-(2-diethylaminoethoxy)phenyl]-2-(3',5'-dimethylbenzoyl)benzothiophene.
- 20. A pharmaceutical composition having coronary vasodilator activity comprising a pharmaceutical carrier and an effective and nontoxic amount of a compound of claim 1.
- 21. A method of producing coronary vasodilation comprising administering to an animal an effective and nontoxic amount of a compound of claim 1.
- 22. A pharmaceutical composition having anti-anginal activity comprising a pharmaceutical carrier and an effective and nontoxic amount of the compound 2-[4'-(2-diethylaminoethoxy)phenyl]-3-(3',5'-dimethylbenzoyl)benzofuran.
- 23. A method of producing anti-anginal activity comprising administering to an animal an effective and nontoxic amount of the compound 2-[4'-(2-diethylaminoethoxy)phenyl]-3-(3',5'-dimethylbenzoyl)benzofuran.
Parent Case Info
This application is a continuation-in-part of Ser. No. 515,808, filed Oct. 17, 1974, now abandoned, which is a continuation-in-part of Ser. No. 462,008, filed Apr. 18, 1974, now abandoned.
US Referenced Citations (4)
Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
515808 |
Oct 1974 |
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Parent |
462008 |
Apr 1974 |
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