US4198519A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Anti-inflammatory compounds
Assignee: Beecham Group PLC
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Filing: 1978-10-18
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Granted: 1980-04-15
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Expires: 1998-10-18
Abstract
Abstract 4-(Thien-2-oyl- and thien-3-oylphenyl)pentan-2-ones and 4-(thien-2-oyl- and thien-3-oylphenyl)butan-2-ones, the corresponding pentan-2-ols and butan-2-ols, and esters of the latter alkanols are anti-inflammatory agents. The compounds, of which 4-[4-(2-thienoyl)phenyl]pentan-2-one is a representative embodiment, can be prepared by acylation of the corresponding 4-phenylpentan-2-one, 4-phenylbutan-2-one, or an ester of the corresponding pentan-2-ol or butan-2-ol, with a thienylcarboxylic acid, or by acylation of a 4-(4-carboxyphenyl)pentan-2-one, 4-(4-carboxyphenyl)butan-2-one or an ester of the corresponding pentan-2-ol or butan-2-ol with thiophene, optionally in either case with subsequent reduction of the resultant alkanone and with optional esterification of the resultant alkanol.
Inventors
- 👤 Alexander C. Goudie
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 15:32
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/22; C07C; C07C45/00; C07C45/45
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
123 words
A compound of the formula: ##STR7## wherein A is --CHRCH 2 -- or --CR═CH-- in which R is hydrogen or methyl and B is CO, CHOH or CHOCOR 1 wherein R 1 is phenyl, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by phenyl, or phenyl, alkyl of 1 to 4 carbon atoms, or alkyl of 1 to 4 carbon atoms substituted by phenyl, said phenyl, alkyl or phenyl substituted alkyl being substituted by a member selected from the group consisting of hydroxyl, acetoxyl, methoxyl, acetamido, amino or a nontoxic salt thereof, alkylamino of 1 to 4 carbon atoms in the alky moiety, dialkylamino of 1 to 4 carbon atoms in each alkyl moiety and carboxyl.
Claim 2
Dependent Claim
123 words
A compound of the formula: ##STR7## wherein A is --CHRCH 2 -- or --CR═CH-- in which R is hydrogen or methyl and B is CO, CHOH or CHOCOR 1 wherein R 1 is phenyl, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by phenyl, or phenyl, alkyl of 1 to 4 carbon atoms, or alkyl of 1 to 4 carbon atoms substituted by phenyl, said phenyl, alkyl or phenyl substituted alkyl being substituted by a member selected from the group consisting of hydroxyl, acetoxyl, methoxyl, acetamido, amino or a nontoxic salt thereof, alkylamino of 1 to 4 carbon atoms in the alky moiety, dialkylamino of 1 to 4 carbon atoms in each alkyl moiety and carboxyl.
Claim 3
Dependent Claim
43 words
A compound according to claim 1 which has the formula: ##STR8## wherein A is --CHRCH 2 -- or --CR═CH-- in which R is hydrogen or methyl and B is CO, CHOH or CHOCOR" where R" is alkyl of 1 to 4 carbon atoms.
Claim 4
Dependent Claim
12 words
A compound according to claim 1 wherein B is CO or CHOH.
Claim 5
Dependent Claim
14 words
A compound according to claim 1 wherein A is --CHCH 3 CH 2 --.
Claim 6
Dependent Claim
28 words
A compound according to claim 1 which has the formula: ##STR9## wherein B is CO, CHOH or CHOCOR" wherein R" is alkyl of 1 to 4 carbon atoms.
Claim 7
Dependent Claim
12 words
A compound according to claim 5 wherein B is CO or CHOH.
Claim 8
Dependent Claim
10 words
A compound according to claim 4 wherein B is CO.
Claim 9
Dependent Claim
19 words
A compound according to claim 1 which has a chiral centre which is in R--, S-- or RS-- form.
Claim 10
Dependent Claim
27 words
A compound according to claim 1 in which R is methyl wherein the chiral carbon atom α- to the phenyl ring is in the S-- or SR--form.
Claim 11
Dependent Claim
9 words
The compound according to claim 1 which is 4-[4'-(2-thienoyl)-phenyl]-pentan-2-one.
Claim 12
Dependent Claim
9 words
The compound according to claim 1 which is 4-[4'-(2'-thienoyl)-phenyl]-butan-2-one.
Claim 13
Dependent Claim
9 words
The compound according to claim 1 which is 4-[4'-(3'-thienoyl)-phenyl]-butan-2-one.
Claim 14
Dependent Claim
9 words
The compound according to claim 1 which is S-4-[4'-(2'-thienoyl)-phenyl]-pentan-2-one.
Claim 15
Dependent Claim
9 words
The compound according to claim 1 which is R-4-[4'-(2-thienoyl)-phenyl]-pentan-2-one.
Claim 16
Dependent Claim
19 words
The compound according to claim 1 which has a chiral center and is in the form of the R-isomer.
Claim 17
Dependent Claim
19 words
The compound according to claim 1 which has a chiral center and is in the form of the S-isomer.
Claim 18
Dependent Claim
17 words
A mixture of R and S-isomers of a compound according to claim 1 having a chiral center.
Claim 19
Dependent Claim
29 words
A compound according to claim 1 wherein R 1 is alkyl of 1 to 4 carbon atoms, phenyl, benzyl, phenylethyl, acetoxymethyl, methoxymethyl, hydroxymethyl, aminomethyl, 2-acetoxyphenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl or 3,4,5-trimethoxyphenyl.
Claim 20
Dependent Claim
25 words
A compound according to claim 1 wherein R 1 is methyl, ethyl, n-propyl, phenyl, benzyl, phenylethyl, acetoxymethyl, methoxymethyl, hydroxymethyl, aminomethyl, 2-acetoxyphenyl, 4-methoxyphenyl, 3,4,-dimethoxyphenyl or 3,4,5-trimethoxyphenyl.
Claim 21
Dependent Claim
23 words
A compound according to claim 1 wherein B is CO, CHOH or CHOCOR" wherein R" is alkyl of 1 to 4 carbon atoms.
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) | 1983-04-15 | 1983-10-15 | 1984-04-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-04-15 | 1987-10-15 | 1988-04-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-04-15 | 1991-10-15 | 1992-04-15 | $7700.00 | Window Closed / Lapsed |