US4276430A
Expired / Lapsed
US
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Analgesic and anti-inflammatory compounds and compositions containing same
Assignee: Procter and Gamble Co
•
Filing: 1979-07-26
•
Granted: 1981-06-30
•
Expires: 1999-07-26
Abstract
Abstract Dihydroxybenzoic acid derivatives and compositions containing same are useful for topical application to the skin as well as for systemic administration. The compounds are especially effective for providing an analgesic, anti-pyretic, and anti-inflammatory effect.
Inventors
- 👤 Herbert H. Reller
- 👤 Herbert C. Kretschmar
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 02:16
CPC Classifications
A; A61; A61Q; A61Q19/00; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/33; A61K8/37
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
57 words
A compound of the formula ##STR4## wherein R 1 is an alkyl group having from 1 to 4 carbon atoms, Y is O, R 2 is an alkyl group having from 6 to 8 carbon atoms or benzyl and X is COR 3 where R 3 is an alkyl group having from 1 to 4 carbon atoms.
Claim 2
Dependent Claim
57 words
A compound of the formula ##STR4## wherein R 1 is an alkyl group having from 1 to 4 carbon atoms, Y is O, R 2 is an alkyl group having from 6 to 8 carbon atoms or benzyl and X is COR 3 where R 3 is an alkyl group having from 1 to 4 carbon atoms.
Claim 3
Dependent Claim
10 words
The compound of claim 1 wherein R 2 is benzyl.
Claim 4
Dependent Claim
19 words
The compound of claim 1 wherein R 2 is an alkyl group having from 6 to 8 carbon atoms.
Claim 5
Dependent Claim
12 words
The compound of claim 3 wherein R 2 is a hexyl group.
Claim 6
Dependent Claim
15 words
The compound of claim 1 wherein R 1 and R 3 are tertiary butyl groups.
Claim 7
Dependent Claim
14 words
The compound of claim 1 wherein R 1 and R 3 are methyl groups.
Claim 8
Dependent Claim
2 words
Benzyl 2,5-diacetoxybenzoate.
Claim 9
Dependent Claim
2 words
Benzyl 2,5-diacetoxybenzoate.
Claim 10
Dependent Claim
2 words
Hexyl 2,5-diacetoxybenzoate.
Claim 11
Dependent Claim
2 words
Hexyl 2,5-diacetoxybenzoate.
Claim 12
Dependent Claim
83 words
A composition to provide an analgesic effect and alleviate inflammation comprising: (a) an effective amount of a 2,5-dihydroxybenzoic acid derivative of the formula ##STR5## wherein R 1 is an alkyl group having from 1 to 4 carbon atoms; Y is O, R 2 is an alkyl group having from 6 to 8 carbon atoms or benzyl and X is COR 3 wherein R 3 is an alkyl group having from 1 to 4 carbon atoms; and (b) the balance a pharmaceutically acceptable carrier.
Claim 13
Dependent Claim
83 words
A composition to provide an analgesic effect and alleviate inflammation comprising: (a) an effective amount of a 2,5-dihydroxybenzoic acid derivative of the formula ##STR5## wherein R 1 is an alkyl group having from 1 to 4 carbon atoms; Y is O, R 2 is an alkyl group having from 6 to 8 carbon atoms or benzyl and X is COR 3 wherein R 3 is an alkyl group having from 1 to 4 carbon atoms; and (b) the balance a pharmaceutically acceptable carrier.
Claim 14
Dependent Claim
10 words
The composition of claim 9 wherein R 2 is benzyl.
Claim 15
Dependent Claim
19 words
The composition of claim 9 wherein R 2 is an alkyl group having from 6 to 8 carbon atoms.
Claim 16
Dependent Claim
12 words
The composition of claim 11 wherein R 2 is a hexyl group.
Claim 17
Dependent Claim
15 words
The composition of claim 9 wherein R 1 and R 3 are tertiary butyl groups.
Claim 18
Dependent Claim
14 words
The composition of claim 9 wherein R 1 and R 3 are methyl groups.
Claim 19
Dependent Claim
13 words
The composition of claim 9 wherein the dihydroxybenzoic acid derivative is benzyl 2,5-diacetoxybenzoate.
Claim 20
Dependent Claim
13 words
The composition of claim 9 wherein the dihydroxybenzoic acid derivative is hexyl 2,5-diacetoxybenzoate.
Claim 21
Dependent Claim
23 words
The composition of claim 9 for topical application to skin wherein the dihydroxybenzoic acid derivative represents from 0.001% to 10% of the composition.
Claim 22
Dependent Claim
30 words
The composition of claim 17 in the form of a lotion comprising: (a) the dihydroxybenzoic acid derivative; (b) from 1% to 25% of an emollient; and (c) the balance water.
Claim 23
Dependent Claim
14 words
The composition of claim 18 further comprising from 1% to 10% of an emulsifier.
Claim 24
Dependent Claim
30 words
The composition of claim 17 in the form of a cream comprising: (a) the dihydroxybenzoic acid derivative; (b) from 5% to 50% of an emollient; and (c) the balance water.
Claim 25
Dependent Claim
14 words
The composition of claim 20 further comprising from 3% to 50% of an emulsifier.
Claim 26
Dependent Claim
24 words
The composition of claim 17 in the form of a solution comprising: (a) the dihydroxybenzoic acid derivative; and (b) the balance an organic solvent.
Claim 27
Dependent Claim
40 words
The composition of claim 17 in the form of a gel comprising: (a) the dihydroxybenzoic acid derivative; (b) from 5% to 75% of an organic solvent; (c) from 0.5% to 20% of a thickening agent; and (d) the balance water.
Claim 28
Dependent Claim
26 words
The composition of claim 17 in the form of a solid comprising: (a) the dihydroxybenzoic acid derivative; and (b) from 50% to 98% of an emollient.
Claim 29
Dependent Claim
30 words
The composition of claim 9 for oral administration in unit dosage form comprising from about 15 mg to about 1 g of dihydroxybenzoic acid derivative and a pharmaceutically acceptable carrier.
Claim 30
Dependent Claim
26 words
The composition of claim 9 for parenteral administration comprising from about 0.5 mg to about 200 mg of dihydroxybenzoic acid derivative and a pharmaceutically acceptable carrier.
Claim 31
Independent Claim
82 words
A method for topically providing an analgesic effect and alleviating inflammation comprising applying to the epidermal area so affected an effective amount of a dihydroxybenzoic acid derivative of the formula ##STR6## wherein R 1 is an alkyl group having from 1 to 4 carbon atoms, Y is O, R 2 is an alkyl group having from 6 to 8 carbon atoms or benzyl and X is COR 3 wherein R 3 is an alkyl group having from 1 to 4 carbon atoms.
Claim 32
Independent Claim
82 words
A method for topically providing an analgesic effect and alleviating inflammation comprising applying to the epidermal area so affected an effective amount of a dihydroxybenzoic acid derivative of the formula ##STR6## wherein R 1 is an alkyl group having from 1 to 4 carbon atoms, Y is O, R 2 is an alkyl group having from 6 to 8 carbon atoms or benzyl and X is COR 3 wherein R 3 is an alkyl group having from 1 to 4 carbon atoms.
Claim 33
Dependent Claim
25 words
The method of claim 27 wherein from 0.01 μg to 500 μg of the dihydroxybenzoic acid derivative is applied per square centimeter of epidermal area.
Claim 34
Dependent Claim
13 words
The method of claim 28 wherein the dihydroxybenzoic acid derivative is benzyl 2,5-diacetoxybenzoate.
Claim 35
Dependent Claim
13 words
The method of claim 28 wherein the dihydroxybenzoic acid derivative is hexyl 2,5-diacetoxybenzoate.
Claim 36
Dependent Claim
23 words
The method of claim 27 wherein the dihydroxybenzoic acid derivative is applied to the skin in the presence of a pharmaceutically acceptable carrier.
Claim 37
Dependent Claim
29 words
The method of claim 31 wherein inflammation of skin is treated with from 0.01 μg to 50 μg of the dihydroxybenzoic acid derivative per square centimeter of epidermal area.
Claim 38
Dependent Claim
33 words
The method of claim 31 wherein inflammation of muscles, tendons, bursa or joints is treated with from 0.1 μg to 500 μg of the dihydroxybenzoic acid derivative per square centimeter of epidermal area.
Claim 39
Independent Claim
82 words
A method for providing an analgesic effect and alleviating inflammation comprising systemically administering to the affected person a safe and effective amount of a dihydroxybenzoic acid derivative of the formula ##STR7## wherein R 1 is an alkyl group having from 1 to 4 carbon atoms, Y is O, R 2 is an alkyl group having from 6 to 8 carbon atoms or benzyl and X is COR 3 wherein R 3 is an alkyl group having from 1 to 4 carbon atoms.
Claim 40
Independent Claim
82 words
A method for providing an analgesic effect and alleviating inflammation comprising systemically administering to the affected person a safe and effective amount of a dihydroxybenzoic acid derivative of the formula ##STR7## wherein R 1 is an alkyl group having from 1 to 4 carbon atoms, Y is O, R 2 is an alkyl group having from 6 to 8 carbon atoms or benzyl and X is COR 3 wherein R 3 is an alkyl group having from 1 to 4 carbon atoms.
Claim 41
Dependent Claim
24 words
The method of claim 34 wherein from about 0.05 g to about 50 g per day of the dihydroxybenzoic acid derivative is administered orally.
Claim 42
Dependent Claim
13 words
The method of claim 35 wherein the dihydroxybenzoic acid derivative is benzyl 2,5-diacetoxybenzoate.
Claim 43
Dependent Claim
13 words
The method of claim 35 wherein the dihydroxybenzoic acid derivative is hexyl 2,5-diacetoxybenzoate.
Claim 44
Dependent Claim
24 words
The method of claim 34 wherein from about 0.5 mg to about 200 mg per day of the dihydroxybenzoic acid derivative is administered parenterally.
Claim 45
Dependent Claim
13 words
The method of claim 38 wherein the 2,5-dihydroxybenzoic acid derivative is benzyl 2,5-diacetoxybenzoate.
References Cited (Backward Citations)
GB1220447A
Cited
GB1393326A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-06-29 | 1984-12-29 | 1985-06-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-29 | 1988-12-29 | 1989-06-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-29 | 1992-12-29 | 1993-06-30 | $7700.00 | Window Closed / Lapsed |