US4062978A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Phenyl butanones
Assignee: Beecham Group PLC
•
Filing: 1975-06-20
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Granted: 1977-12-13
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Expires: 1995-06-20
Abstract
Abstract Anti-inflammatory compositions are prepared which comprise a therapeutically effective amount of a compound of the formula ##STR1## wherein X is CO or CHOH; Y is CO, an oxygen atom or a direct bond; the dotted line represents a double bond which is optionally present when Y is an oxygen atom or a direct bond; R 1 is hydrogen or methyl; R 2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxyl, hydroxyl, acetoxyl, nitro or amino; R 3 is alkyl of 3-8 carbon atoms, cycloalkyl of 3-8 carbon atoms, alkenyl of 3-8 carbon atoms, cycloalkenyl of 5-8 carbon atoms, phenyl or phenyl substituted by 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxyl, ethoxyl, benzyloxyl, hydroxyl, acetoxyl, trifluoromethyl, nitro, amino, acetyl, methylthiol, methylsulphonyl, methylamino and dimethylamino. Compounds of the above formula are novel except that R 1 must be methyl: when R 3 -- Y is a 4-phenyl group, R 2 is hydrogen and X is CO; when R 3 -- Y is a 4-benzyl group and R 2 is hydrogen; and also when R 3 -- Y is a 3-benzoyl group, R 2 is hydrogen and X is CO.
Inventors
- 👤 William Gwyn Cole
- 👤 Alexander Crossan Goudie
- 👤 Carl John Rose
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 11:27
CPC Classifications
C; C07; C07C; C07C49/00; C07C49/76; C07C49/84; C07C205/00; C07C205/45; C07C29/00; C07C29/132; C07C29/136; C07C29/143; C07C45/00; C07C45/45; C07C45/46; C07C45/61; C07C45/62; C07C45/64; C07C45/67; C07C45/68; C07C45/70; C07C45/71; C07C49/20; C07C49/213; C07C49/215; C07C49/217; C07C49/223; C07C49/225; C07C49/227; C07C49/233; C07C49/235; C07C49/24; C07C49/245; C07C49/248; C07C49/255; C07C49/782; C07C49/792; C07C49/794; C07C49/80; C07C49/813; C07C49/82; C07C49/83
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
83 words
A pharmaceutical composition useful for the treatment of inflammation in humans and animals which comprises an anti-inflammatory amount of a compound of the formula ##STR16## wherein X is CO; Y is an oxygen atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms or cycloalkenyl of 5 to 8 carbon atoms, in combination with a pharmaceutically acceptable carrier.
Claim 2
Dependent Claim
83 words
A pharmaceutical composition useful for the treatment of inflammation in humans and animals which comprises an anti-inflammatory amount of a compound of the formula ##STR16## wherein X is CO; Y is an oxygen atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms or cycloalkenyl of 5 to 8 carbon atoms, in combination with a pharmaceutically acceptable carrier.
Claim 3
Dependent Claim
51 words
A composition according to claim 1 wherein the compound is of the formula ##STR17## wherein Y is an oxygen atom; R 1 is hydrogen or methyl; R 2 is hydrogen; the dotted line represents a double bond which may be present or absent; and R 10 is cyclohexenyl, allyl or butenyl.
Claim 4
Dependent Claim
57 words
A compound of the formula ##STR18## wherein X is CO; Y is an oxygen atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms or cycloalkenyl of 5 to 8 carbon atoms.
Claim 5
Dependent Claim
57 words
A compound of the formula ##STR18## wherein X is CO; Y is an oxygen atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms or cycloalkenyl of 5 to 8 carbon atoms.
Claim 6
Dependent Claim
47 words
A compound according to claim 3 of the formula ##STR19## wherein Y is an oxygen atom; R 1 is hydrogen or methyl; R 2 is hydrogen; the dotted line represents a double bond which may be present or absent; and R 10 is cyclohexenly, ally or butenyl.
Claim 7
Dependent Claim
75 words
A pharmaceutical composition useful for the treatment of inflammation in humans and animals which comprises an anti-inflammatory ammount of a compound of the formula ##STR20## wherein X is CO; Y is an oxygen atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms; in combination with a pharmaceutically acceptable carrier.
Claim 8
Dependent Claim
75 words
A pharmaceutical composition useful for the treatment of inflammation in humans and animals which comprises an anti-inflammatory ammount of a compound of the formula ##STR20## wherein X is CO; Y is an oxygen atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms; in combination with a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim
13 words
A composition according to claim 5 wherein R 3 is allyl or butenyl.
Claim 10
Dependent Claim
11 words
A composition according to claim 5 wherein the compound is 4-(p-allyloxyphenyl)-2-butanone.
Claim 11
Dependent Claim
10 words
A composition according to claim 5 in oral administration form.
Claim 12
Dependent Claim
10 words
A composition according to claim 5 in parenteral administration form.
Claim 13
Independent Claim
80 words
A method of treating inflammation in humans and animals which comprises adminstering to a human or animal in need thereof an anti-inflammatory amount of a compound of the formula ##STR21## wherein X is CO; Y is an oxygen atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms; in combination with a pharmaceutically acceptable carrier.
Claim 14
Independent Claim
80 words
A method of treating inflammation in humans and animals which comprises adminstering to a human or animal in need thereof an anti-inflammatory amount of a compound of the formula ##STR21## wherein X is CO; Y is an oxygen atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms; in combination with a pharmaceutically acceptable carrier.
Claim 15
Dependent Claim
13 words
A method according to claim 10 wherein R 3 is allyl or butenyl.
Claim 16
Dependent Claim
11 words
A method according to claim 10 wherein the compound is 4-(p-allyloxyphenyl)-2-butanone.
Claim 17
Dependent Claim
11 words
A method according to claim 10 wherein the administration is oral.
Claim 18
Dependent Claim
11 words
A method according to claim 10 wherein the administration is parenteral.
Claim 19
Dependent Claim
49 words
A compound of the formula ##STR22## wherein X is CO; Y is an oxygem atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms.
Claim 20
Dependent Claim
49 words
A compound of the formula ##STR22## wherein X is CO; Y is an oxygem atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms.
Claim 21
Dependent Claim
13 words
A compound according to claim 15 wherein R 3 is allyl or butenyl.
Claim 22
Dependent Claim
9 words
The compound according to claim 15 which is 4-(p-allyloxyphenyl)-2-butanone.
Claim 23
Independent Claim
88 words
A method of treating inflammation in humans and animals which comprises administering to a human or animal in need thereof an anti-inflammatory amount of a compound of the formula ##STR23## wherein X is CO; Y is an oxygem atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms or cycloalkenyl of 5 to 8 carbon atoms, in combination with a pharmaceutically acceptable carrier.
Claim 24
Independent Claim
88 words
A method of treating inflammation in humans and animals which comprises administering to a human or animal in need thereof an anti-inflammatory amount of a compound of the formula ##STR23## wherein X is CO; Y is an oxygem atom; the dotted line represents a double bond which may be present or absent; R 1 is hydrogen or methyl; R 2 is hydrogen; and R 3 is alkenyl of 3 to 8 carbon atoms or cycloalkenyl of 5 to 8 carbon atoms, in combination with a pharmaceutically acceptable carrier.
Claim 25
Dependent Claim
51 words
A method according to claim 18 wherein the compound is of the formula ##STR24## wherein Y is an oxygen atom; R 1 is hydrogen or methyl; R 2 is hydrogen; the dotted line represents a double bond which may be present or absent; and R 10 is cyclohexenyl, allyl or butenyl.
Claim 26
Dependent Claim
11 words
A method according to claim 18 wherein the administration is oral.
Claim 27
Dependent Claim
11 words
A method according to claim 18 wherein the administration is parenteral.
Claim 28
Dependent Claim
10 words
A composition according to claim 1 in oral administration form.
Claim 29
Dependent Claim
10 words
A composition according to claim 1 in parenteral administration form.
References Cited (Backward Citations)
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Cited
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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) | 1980-12-12 | 1981-06-13 | 1981-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-12 | 1985-06-13 | 1985-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-12 | 1989-06-13 | 1989-12-13 | $7700.00 | Window Closed / Lapsed |