US4452811A
Expired / Lapsed
US
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Monohalogenated derivatives of 7-hydroxy-coumarin, pharmaceutical compositions containing the same and methods of using said compositions
Assignee: Fidia SpA
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Filing: 1982-02-01
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Granted: 1984-06-05
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Expires: 2002-02-01
Abstract
Abstract A selective process is described for producing monohalogenated derivatives of 7-hydroxy coumarin wherein the halo substituent is at the desired position and the final product is free of other monohalogenated isomers. The resulting products and pharmaceutical compositions containing the same, especially those wherein the halo substituent is at the 8 position, have valuable specific coronary vasodilating activity.
Inventors
- 👤 Francesco Della Valle
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 03:45
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/06; C07D311/08; C07D311/16
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
65 words
A substantially pure compound having the formula: ##STR8## wherein X represents a halogen atom, R 1 is selected from the group consisting of piperidino ethyl, morpholino ethyl, diethylamino ethyl and diethylamine propyl, R 2 is selected from the group consisting of methyl and phenyl, and R 3 is selected from the group consisting of ethoxycarbonyl methyl and ethoxycarbonyl ethyl or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
65 words
A substantially pure compound having the formula: ##STR8## wherein X represents a halogen atom, R 1 is selected from the group consisting of piperidino ethyl, morpholino ethyl, diethylamino ethyl and diethylamine propyl, R 2 is selected from the group consisting of methyl and phenyl, and R 3 is selected from the group consisting of ethoxycarbonyl methyl and ethoxycarbonyl ethyl or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
21 words
The substantially pure compound according to claim 1, wherein X is selected from the group consisting of Br, Cl or I.
Claim 4
Dependent Claim
16 words
The substantially pure compound according to claim 1, 8-monochloro-3(β-diethylaminoethyl)-4-methyl-7-ethoxycarbonylmethoxy coumarin or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
16 words
The substantially pure compound according to claim 1, 8-monobromo-3(β-diethylaminoethyl)-4-methyl-7-ethoxycarbonylmethoxy coumarin or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
17 words
The substantially pure compound according to claim 1, 8-monochloro-3(β-diethylaminoethyl)-4-methyl-7-ethoxycarbonylmethoxy coumarin hydrochloride, which melts at about 219°-220° C.
Claim 7
Dependent Claim
17 words
The substantially pure compound according to claim 1, 8-monobromo-3(β-diethylaminoethyl)-4-methyl-7-ethoxycarbonylmethoxy coumarin hydrochloride, which melts at about 202°-203° C.
Claim 8
Dependent Claim
82 words
A pharmaceutical composition comprising an effective vasodilating amount of a substantially pure 7-hydroxycoumarin compound of the formula: ##STR9## wherein X represents a halogen atom, R 1 is selected from the group consisting of piperidino ethyl, morpholino ethyl, diethylamino ethyl and diethylamino propyl, R 2 is selected from the group consisting of methyl and phenyl, and R 3 is selected from the group consisting of ethoxycarbonyl methyl and ethoxycarbonyl ethyl or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent.
Claim 9
Dependent Claim
82 words
A pharmaceutical composition comprising an effective vasodilating amount of a substantially pure 7-hydroxycoumarin compound of the formula: ##STR9## wherein X represents a halogen atom, R 1 is selected from the group consisting of piperidino ethyl, morpholino ethyl, diethylamino ethyl and diethylamino propyl, R 2 is selected from the group consisting of methyl and phenyl, and R 3 is selected from the group consisting of ethoxycarbonyl methyl and ethoxycarbonyl ethyl or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent.
Claim 10
Dependent Claim
13 words
The pharmaceutical composition according to claim 7, in the form of a tablet.
Claim 11
Dependent Claim
13 words
The pharmaceutical composition according to claim 7, in the form of a dragee.
Claim 12
Dependent Claim
13 words
The pharmaceutical composition according to claim 7, in the form of a capsule.
Claim 13
Dependent Claim
14 words
The pharmaceutical composition according to claim 7, in the form of an injectable solution.
Claim 14
Independent Claim
89 words
A method of treating coronary diseases in mammals caused by the obstruction of blood vessels which comprises administering thereto an effective vasodilating amount of a substantially pure compound having the formula: ##STR10## wherein X represents a halogen atom, R 1 is selected from the group consisting of piperidino ethyl, morpholino ethyl, diethylamino ethyl and diethylamino propyl, R 2 is selected from the group consisting of methyl and phenyl, and R 3 is selected from the group consisting of ethoxycarbonyl methyl and ethoxycarbonyl ethyl or a pharmaceutically acceptable salt thereof.
Claim 15
Independent Claim
89 words
A method of treating coronary diseases in mammals caused by the obstruction of blood vessels which comprises administering thereto an effective vasodilating amount of a substantially pure compound having the formula: ##STR10## wherein X represents a halogen atom, R 1 is selected from the group consisting of piperidino ethyl, morpholino ethyl, diethylamino ethyl and diethylamino propyl, R 2 is selected from the group consisting of methyl and phenyl, and R 3 is selected from the group consisting of ethoxycarbonyl methyl and ethoxycarbonyl ethyl or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
26 words
The method according to claim 12, wherein the active ingredient is administered orally to the human or animal in an amount of about 50-400 mg daily.
Claim 17
Dependent Claim
23 words
The method according to claim 12, wherein the active ingredient is administered intramuscularly or intravenously in an amount of about 20-100 mg daily.
Claim 18
Dependent Claim
11 words
The method according to claim 12, wherein said mammals are animals.
Claim 19
Dependent Claim
11 words
The method according to claim 12, wherein said mammals are canine.
Claim 20
Dependent Claim
11 words
The method according to claim 12, wherein said mammals are human.
Claim 21
Dependent Claim
26 words
The method according to claim 12, wherein said substantially pure compound is administered in an amount sufficient to effectively increase the coronary flux or said mammals.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-06-05 | 1987-12-05 | 1988-06-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-06-05 | 1991-12-05 | 1992-06-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-06-05 | 1995-12-05 | 1996-06-05 | $7700.00 | Window Closed / Lapsed |