US4024273A
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US
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Coronary vasodilator and anti-anginal compositions comprising substituted benzofurans and benzothiophenes and methods of producing coronary vasodilation and anti-anginal activity
Assignee: GlaxoSmithKline LLC
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Filing: 1975-11-17
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Granted: 1977-05-17
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Expires: 1995-11-17
Abstract
Abstract The compounds of this invention are substituted benzofurans and benzothiophenes having pharmacological activity. In particular, these compounds have coronary vasodilator activity and are useful in the treatment of angina pectoris.
Inventors
- 👤 L. Martin Brenner
- 👤 John M. Petta
- 👤 Stephen T. Ross
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 09:31
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/78; C07D307/79; C07D307/80; C07D333/00; C07D333/50; C07D333/52; C07D333/54; C07D333/56
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
112 words
A pharmaceutical composition having coronary vasodilator activity comprising a pharmaceutical carrier and, in an amount to produce said activity, a compound of the formula: ##STR7## or a pharmaceutically acceptable acid addition salt thereof, in which: R 1 is hydrogen, halo, trifluoromethyl, nitro, lower alkyl or lower alkoxy; R 2 and R 3 are hydrogen, lower alkyl or lower alkoxy; R 4 is hydrogen or straight chain lower alkyl; R 5 is straight chain lower alkyl; R 6 is phenyl, lower alkylphenyl, di-lower alkylphenyl, tri-lower alkylphenyl, lower alkoxyphenyl, di-lower alkoxyphenyl, tri-lower alkoxyphenyl, halophenyl, dihalophenyl, trihalophenyl, trifluoromethylphenyl, benzyl, halobenzyl, lower alkylbenzyl, lower alkoxybenzyl or trifluoromethylbenzyl; n is 2 to 4; and Z is sulfur.
Claim 2
Dependent Claim
112 words
A pharmaceutical composition having coronary vasodilator activity comprising a pharmaceutical carrier and, in an amount to produce said activity, a compound of the formula: ##STR7## or a pharmaceutically acceptable acid addition salt thereof, in which: R 1 is hydrogen, halo, trifluoromethyl, nitro, lower alkyl or lower alkoxy; R 2 and R 3 are hydrogen, lower alkyl or lower alkoxy; R 4 is hydrogen or straight chain lower alkyl; R 5 is straight chain lower alkyl; R 6 is phenyl, lower alkylphenyl, di-lower alkylphenyl, tri-lower alkylphenyl, lower alkoxyphenyl, di-lower alkoxyphenyl, tri-lower alkoxyphenyl, halophenyl, dihalophenyl, trihalophenyl, trifluoromethylphenyl, benzyl, halobenzyl, lower alkylbenzyl, lower alkoxybenzyl or trifluoromethylbenzyl; n is 2 to 4; and Z is sulfur.
Claim 3
Independent Claim
113 words
A method of producing coronary vasodilation comprising administering to an animal in need of said effect an effective amount of a compound of the formula: ##STR8## or a pharmaceutically acceptable acid addition salt thereof, in which: R 1 is hydrogen, halo, trifluoromethyl, nitro, lower alkyl or lower alkoxy; R 2 and R 3 are hydrogen, lower alkyl or lower alkoxy; R 4 is hydrogen or straight chain lower alkyl; R 5 is straight chain lower alkyl; R 6 is phenyl, lower alkylphenyl, di-lower alkylphenyl, tri-lower alkylphenyl, lower alkoxyphenyl, di-lower alkoxyphenyl, tri-lower alkoxyphenyl, halophenyl, dihalophenyl, trihalophenyl, trifluoromethylphenyl, benzyl, halobenzyl, lower alkylbenzyl, lower alkoxybenzyl or trifluoromethylbenzyl; n is 2 to 4; and Z is sulfur.
Claim 4
Independent Claim
113 words
A method of producing coronary vasodilation comprising administering to an animal in need of said effect an effective amount of a compound of the formula: ##STR8## or a pharmaceutically acceptable acid addition salt thereof, in which: R 1 is hydrogen, halo, trifluoromethyl, nitro, lower alkyl or lower alkoxy; R 2 and R 3 are hydrogen, lower alkyl or lower alkoxy; R 4 is hydrogen or straight chain lower alkyl; R 5 is straight chain lower alkyl; R 6 is phenyl, lower alkylphenyl, di-lower alkylphenyl, tri-lower alkylphenyl, lower alkoxyphenyl, di-lower alkoxyphenyl, tri-lower alkoxyphenyl, halophenyl, dihalophenyl, trihalophenyl, trifluoromethylphenyl, benzyl, halobenzyl, lower alkylbenzyl, lower alkoxybenzyl or trifluoromethylbenzyl; n is 2 to 4; and Z is sulfur.
Claim 5
Dependent Claim
19 words
A pharmaceutical composition having antianginal activity comprising a pharmaceutical carrier and, in an amount to produce said activity, 3-[4-(3-diethylaminopropoxy)benzoyl]-2-phenylbenzofuran.
Claim 6
Dependent Claim
19 words
A pharmaceutical composition having antianginal activity comprising a pharmaceutical carrier and, in an amount to produce said activity, 3-[4-(3-diethylaminopropoxy)benzoyl]-2-phenylbenzofuran.
Claim 7
Dependent Claim
19 words
A pharmaceutical composition having anti-anginal activity comprising a pharmaceutical carrier and, in an amount to produce said activity, 3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-tolyl)benzofuran.
Claim 8
Dependent Claim
19 words
A pharmaceutical composition having anti-anginal activity comprising a pharmaceutical carrier and, in an amount to produce said activity, 3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-tolyl)benzofuran.
Claim 9
Dependent Claim
19 words
A pharmaceutical composition having anti-anginal activity comprising a pharmaceutical carrier and, in an amount to produce said activity, 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-phenylbenzofuran.
Claim 10
Dependent Claim
19 words
A pharmaceutical composition having anti-anginal activity comprising a pharmaceutical carrier and, in an amount to produce said activity, 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-phenylbenzofuran.
Claim 11
Dependent Claim
19 words
A pharmaceutical composition having anti-anginal activity comprising a pharmaceutical carrier and, in an amount to produce said activity, 3-(4-chlorophenyl)-2-[4-(3-diethylaminopropoxy)benzoyl]benzofuran.
Claim 12
Dependent Claim
19 words
A pharmaceutical composition having anti-anginal activity comprising a pharmaceutical carrier and, in an amount to produce said activity, 3-(4-chlorophenyl)-2-[4-(3-diethylaminopropoxy)benzoyl]benzofuran.
Claim 13
Independent Claim
21 words
A method of producing anti-anginal activity comprising administering to an animal in need of said activity an effective amount of 3-[4-(3-diethylaminopropoxy)benzoyl]-2-phenylbenzofuran.
Claim 14
Independent Claim
21 words
A method of producing anti-anginal activity comprising administering to an animal in need of said activity an effective amount of 3-[4-(3-diethylaminopropoxy)benzoyl]-2-phenylbenzofuran.
Claim 15
Independent Claim
21 words
A method of producing anti-anginal activity comprising administering to an animal in need of said activity an effective amount of 3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-tolyl)benzofuran.
Claim 16
Independent Claim
21 words
A method of producing anti-anginal activity comprising administering to an animal in need of said activity an effective amount of 3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-tolyl)benzofuran.
Claim 17
Independent Claim
21 words
A method of producing anti-anginal activity comprising administering to an animal in need of said activity an effective amount of 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-phenylbenzofuran.
Claim 18
Independent Claim
21 words
A method of producing anti-anginal activity comprising administering to an animal in need of said activity an effective amount of 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-phenylbenzofuran.
Claim 19
Independent Claim
21 words
A method of producing anti-anginal activity comprising administering to an animal in need of said activity an effective amount of 3-(4-chlorophenyl)-2-[4-(3-diethylaminopropoxy)benzoyl]benzofuran.
Claim 20
Independent Claim
21 words
A method of producing anti-anginal activity comprising administering to an animal in need of said activity an effective amount of 3-(4-chlorophenyl)-2-[4-(3-diethylaminopropoxy)benzoyl]benzofuran.
Claim 21
Dependent Claim
100 words
A pharmaceutical composition having coronary vasodilator activity comprising a pharmaceutical carrier and, in an amount to produce said activity, a compound of the formula: ##STR9## or a pharmaceutically acceptable acid addition salt thereof, in which the aminoalkoxy side chain is in the para position of the benzoyl ring; R 1 is hydrogen or halo in the 5-position; R 2 and R 3 are hydrogen; R 4 and R 5 are ethyl, n-propyl or n-butyl; R 6 is tolyl, chlorophenyl, bromophenyl, methoxyphenyl, trifluoromethylphenyl, dimethylphenyl, dichlorophenyl, dimethoxyphenyl, trimethoxyphenyl, chlorobenzyl or trifluoromethylbenzyl; n is 2 to 4 and Z is oxygen or sulfur.
Claim 22
Dependent Claim
100 words
A pharmaceutical composition having coronary vasodilator activity comprising a pharmaceutical carrier and, in an amount to produce said activity, a compound of the formula: ##STR9## or a pharmaceutically acceptable acid addition salt thereof, in which the aminoalkoxy side chain is in the para position of the benzoyl ring; R 1 is hydrogen or halo in the 5-position; R 2 and R 3 are hydrogen; R 4 and R 5 are ethyl, n-propyl or n-butyl; R 6 is tolyl, chlorophenyl, bromophenyl, methoxyphenyl, trifluoromethylphenyl, dimethylphenyl, dichlorophenyl, dimethoxyphenyl, trimethoxyphenyl, chlorobenzyl or trifluoromethylbenzyl; n is 2 to 4 and Z is oxygen or sulfur.
Claim 23
Independent Claim
101 words
A method of producing coronary vasodilation comprising administering to an animal in need of said effect an effective amount of a compound of the formula: ##STR10## or a pharmaceutically acceptable acid addition salt thereof, in which the aminoalkoxy side chain is in the para position of the benzoyl ring; R 1 is hydrogen or halo in the 5-position; R 2 and R 3 are hydrogen; R 4 and R 5 are ethyl, n-propyl or n-butyl; R 6 is tolyl, chlorophenyl, bromophenyl, methoxyphenyl, trifluoromethylphenyl, dimethylphenyl, dichlorophenyl, dimethoxyphenyl, trimethoxyphenyl, chlorobenzyl or trifluoromethylbenzyl; n is 2 to 4 and Z is oxygen or sulfur.
Claim 24
Independent Claim
101 words
A method of producing coronary vasodilation comprising administering to an animal in need of said effect an effective amount of a compound of the formula: ##STR10## or a pharmaceutically acceptable acid addition salt thereof, in which the aminoalkoxy side chain is in the para position of the benzoyl ring; R 1 is hydrogen or halo in the 5-position; R 2 and R 3 are hydrogen; R 4 and R 5 are ethyl, n-propyl or n-butyl; R 6 is tolyl, chlorophenyl, bromophenyl, methoxyphenyl, trifluoromethylphenyl, dimethylphenyl, dichlorophenyl, dimethoxyphenyl, trimethoxyphenyl, chlorobenzyl or trifluoromethylbenzyl; n is 2 to 4 and Z is oxygen or sulfur.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-05-16 | 1980-11-15 | 1981-05-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-16 | 1984-11-15 | 1985-05-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-16 | 1988-11-15 | 1989-05-17 | $7700.00 | Window Closed / Lapsed |