Patent US4124724A successfully refreshed from Google Patents.
US4124724A
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Crystalline caffeic acid derivatives and compositions and method for treating snakebite
Assignee: Individual
•
Filing: 1976-11-29
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Granted: 1978-11-07
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Expires: 1996-11-29
Abstract
Abstract Novel crystalline products of manufacture are represented by the formula: ##STR1## wherein R 1 and R 2 are selected from the group consisting of hydroxyl and the caffeoyl group, with the limitation that only one of R 1 and R 2 can be hydroxyl, and the pharmaceutically acceptable salts of the indicated compounds. The compounds are useful as anti-venom agents for hemolytic snake venoms. Pharmaceutical preparations containing the above compounds, or the compound commonly known as caffeic acid wherein both R 1 and R 2 are hydroxyl, are provided for treatment of snakebite victims, as well as the method of using those preparations in such treatment.
Inventors
- 👤 John W. Agoro
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 23:27
CPC Classifications
C; C07; C07C; C07C59/00; C07C59/40; C07C59/42; C07C59/52
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
48 words
A crystalline product of manufacture of the formula: ##STR5## wherein R 1 and R 2 are selected from the group consisting of hydroxyl and the caffeoyl group, with the limitation that only one of R 1 and R 2 can be hydroxyl, and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
48 words
A crystalline product of manufacture of the formula: ##STR5## wherein R 1 and R 2 are selected from the group consisting of hydroxyl and the caffeoyl group, with the limitation that only one of R 1 and R 2 can be hydroxyl, and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
18 words
A crystalline product in accordance with claim 1 of the formula: ##STR6## and the pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
18 words
A crystalline product in accordance with claim 1 of the formula: ##STR7## and the pharmaceutically acceptable salts thereof.
Claim 5
Dependent Claim
24 words
A crystalline product in accordance with claim 1. that is a mixture of compounds of the formula: ##STR8## and the pharmaceutically acceptable salts thereof.
Claim 6
Dependent Claim
18 words
A crystalline product in accordance with claim 1 of the formula: ##STR9## and the pharmaceutically acceptable salts thereof.
Claim 7
Dependent Claim
27 words
A crystalline product of manufacture consisting of a member selected from the group consisting of caffeoyl caffeic acid, decomp. 135°-140° C., and the pharmaceutically acceptable salts thereof.
Claim 8
Dependent Claim
27 words
A crystalline product of manufacture consisting of a member selected from the group consisting of caffeoyl caffeic acid, decomp. 135°-140° C., and the pharmaceutically acceptable salts thereof.
Claim 9
Dependent Claim
23 words
A crystalline product of manufacture consisting of a member selected from the group consisting of 3-hydroxy-4-(3',4-dihydroxycinnamoyl)-cinnamic acid and the pharmaceutically acceptable salts thereof.
Claim 10
Dependent Claim
23 words
A crystalline product of manufacture consisting of a member selected from the group consisting of 3-hydroxy-4-(3',4-dihydroxycinnamoyl)-cinnamic acid and the pharmaceutically acceptable salts thereof.
Claim 11
Dependent Claim
23 words
A crystalline product of manufacture consisting of a member selected from the group consisting of 4-hydroxy-3-(3',4'-dihydroxycinnamoyl)-cinnamic acid and the pharmaceutically acceptable salts thereof.
Claim 12
Dependent Claim
23 words
A crystalline product of manufacture consisting of a member selected from the group consisting of 4-hydroxy-3-(3',4'-dihydroxycinnamoyl)-cinnamic acid and the pharmaceutically acceptable salts thereof.
Claim 13
Dependent Claim
23 words
A crystalline product of manufacture consisting of a member selected from the group consisting of 3,4-di-(3',4'-dihydroxycinnamoyl)-cinnamic acid and the pharmaceutically acceptable salts thereof.
Claim 14
Dependent Claim
23 words
A crystalline product of manufacture consisting of a member selected from the group consisting of 3,4-di-(3',4'-dihydroxycinnamoyl)-cinnamic acid and the pharmaceutically acceptable salts thereof.
Claim 15
Dependent Claim
90 words
A pharmaceutical preparation suitable for oral or parenteral use comprising a therapeutically effective amount of anti-snake venom drug selected from the group consisting of a crystalline product of manufacture of the formula: ##STR10## wherein R 1 and R 2 are the same or different members of the group consisting of hydroxyl and the caffeoyl group, with the limitation that only one of R 1 and R 2 can be hydroxyl, a mixture of said products, and pharmaceutically acceptable salts of said products, together with a pharmaceutically acceptable carrier or diluent.
Claim 16
Dependent Claim
90 words
A pharmaceutical preparation suitable for oral or parenteral use comprising a therapeutically effective amount of anti-snake venom drug selected from the group consisting of a crystalline product of manufacture of the formula: ##STR10## wherein R 1 and R 2 are the same or different members of the group consisting of hydroxyl and the caffeoyl group, with the limitation that only one of R 1 and R 2 can be hydroxyl, a mixture of said products, and pharmaceutically acceptable salts of said products, together with a pharmaceutically acceptable carrier or diluent.
Claim 17
Dependent Claim
12 words
A pharmaceutical preparation in accordance with claim 10 compounded for oral use.
Claim 18
Dependent Claim
12 words
A pharmaceutical preparation in accordance with claim 10 compounded for parenteral use.
Claim 19
Dependent Claim
23 words
A pharmaceutical preparation in accordance with claim 10 wherein said crystalline product of manufacture is 3-hydroxy-4-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim
23 words
A pharmaceutical preparation in accordance with claim 10 wherein said crystalline product of manufacture is 4-hydroxy-3-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
23 words
A pharmaceutical preparation in accordance with claim 10 wherein said crystalline product of manufacture is 3,4-di-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof.
Claim 22
Dependent Claim
22 words
A pharmaceutical preparation in accordance with claim 10 wherein said crystalline product is caffeoyl caffeic acid or a pharmaceutically acceptable salt thereof.
Claim 23
Dependent Claim
39 words
A pharmaceutical preparation suitable for oral or parenteral administration to a mammalian snakebite victim comprising from about 0.03 to about 3.5 mg. of 3,4-dihydroxycinnamic acid or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier or diluent.
Claim 24
Dependent Claim
39 words
A pharmaceutical preparation suitable for oral or parenteral administration to a mammalian snakebite victim comprising from about 0.03 to about 3.5 mg. of 3,4-dihydroxycinnamic acid or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier or diluent.
Claim 25
Dependent Claim
28 words
A pharmaceutical preparation in accordance with claim 17 wherein the trans isomer of 3,4-dihydroxy cinnamic acid is present in a dosage of from 0.03 to about 3.5 mg.
Claim 26
Independent Claim
72 words
A method of inhibiting the hemolytic action of snake venom comprising administering to a mammalian snakebite patient a therapeutically effective amount of anti-snake venom drug selected from the group consisting of a crystalline product of manufacture of the formula: ##STR11## wherein R 1 and R 2 are the same or different members of the group consisting of hydroxyl and the caffeoyl group, a mixture of said products, and pharmaceutically acceptable salts thereof.
Claim 27
Independent Claim
72 words
A method of inhibiting the hemolytic action of snake venom comprising administering to a mammalian snakebite patient a therapeutically effective amount of anti-snake venom drug selected from the group consisting of a crystalline product of manufacture of the formula: ##STR11## wherein R 1 and R 2 are the same or different members of the group consisting of hydroxyl and the caffeoyl group, a mixture of said products, and pharmaceutically acceptable salts thereof.
Claim 28
Dependent Claim
19 words
The method of claim 19 wherein said anti-snake venom drug is 3-hydroxy-4-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof.
Claim 29
Dependent Claim
19 words
The method of claim 19 wherein said anti-snake venom drug is 4-hydroxy-3-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof.
Claim 30
Dependent Claim
19 words
The method of claim 19 wherein said anti-snake venom drug is 3,4-di-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof.
Claim 31
Dependent Claim
19 words
The method of claim 19 wherein said anti-snake venom drug is caffeic acid or a pharmaceutically acceptable salt thereof.
Claim 32
Dependent Claim
37 words
The method of claim 13 comprising treating said snake-bite patient with a total of from 0.03 to 3.5 mg. of caffeic acid or a pharmaceutically acceptable salt thereof and thereafter discontinuing treatment for at least one month.
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) | 1981-11-06 | 1982-05-08 | 1982-11-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-11-06 | 1986-05-08 | 1986-11-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-11-06 | 1990-05-08 | 1990-11-07 | $7700.00 | Window Closed / Lapsed |