Patent US4512368A successfully refreshed from Google Patents.
Patent US4011333A successfully refreshed from Google Patents.
US4011333A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Substituted thiophenecarboxylic acid and esters as hypolipidemic agents
Assignee: Richardson Vicks Inc
•
Filing: 1975-06-16
•
Granted: 1977-03-08
•
Expires: 1995-06-16
Abstract
Abstract Substituted thiophenecarboxylic acid and esters and pharmaceutically acceptable salts thereof of the following general structure are useful as hypolipidemic agents: ##STR1## wherein Y is selected from oxygen and divalent sulfur; R is selected from a straight or branched saturated hydrocarbon chain of from 10 to 20 carbon atoms and a straight or branched unsaturated hydrocarbon chain containing from 10 to 20 carbon atoms and from 1 to 4 double bonds; R 1 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 6 carbon atoms, benzyl, phenethyl, alkane-poly-yl containing from 3 to 6 carbon atoms, and 1,2,3,4,5,6-cyclohexanehexayl; X is an integer of from 1 to 6 with the proviso that when R 1 is alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to from 2 to 6, and when R 1 is other than alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to 1.
Inventors
- 👤 Roger Alan Parker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 10:20
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/38; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
186 words
A method of reducing the lipid concentration in the blood of a patient in need thereof which comprises orally or parenterally administering to said patient a blood lipid lowering effective amount of a compound of the formula: ##STR9## wherein Y is selected from the group consisting of oxygen and divalent sulfur; R is selected from the group consisting of a straight or branched saturated hydrocarbon chain containing from 10 to 20 carbon atoms and a straight or branched unsaturated hydrocarbon chain containing from 10 to 20 carbon atoms and from 1 to 4 double bonds; R 1 is selected from the group consisting of hydrogen, a straight or branched lower alkyl group of from 1 to 6 carbon atoms, benzyl, phenethyl, alkane-poly-yl containing from 3 to 6 carbon atoms and from 2 to 6 univalent bonds, and 1,2,3,4,5,6-cyclohexanehexayl; X is an integer of from 1 to 6 with the proviso that when R 1 is alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to from 2 to 6, and when R 1 is other than alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to 1; or pharmaceutically acceptable salts thereof.
Claim 2
Independent Claim
186 words
A method of reducing the lipid concentration in the blood of a patient in need thereof which comprises orally or parenterally administering to said patient a blood lipid lowering effective amount of a compound of the formula: ##STR9## wherein Y is selected from the group consisting of oxygen and divalent sulfur; R is selected from the group consisting of a straight or branched saturated hydrocarbon chain containing from 10 to 20 carbon atoms and a straight or branched unsaturated hydrocarbon chain containing from 10 to 20 carbon atoms and from 1 to 4 double bonds; R 1 is selected from the group consisting of hydrogen, a straight or branched lower alkyl group of from 1 to 6 carbon atoms, benzyl, phenethyl, alkane-poly-yl containing from 3 to 6 carbon atoms and from 2 to 6 univalent bonds, and 1,2,3,4,5,6-cyclohexanehexayl; X is an integer of from 1 to 6 with the proviso that when R 1 is alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to from 2 to 6, and when R 1 is other than alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to 1; or pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
56 words
The method of claim 1 wherein the compound is of the formula: ##STR10## wherein R and Y have the meanings defined in claim 1; R 2 is selected from the group consisting of hydrogen, a straight or branched lower alkyl group of from 1 to 6 carbon atoms, benzyl and phenethyl; or pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
60 words
The method of claim 1 wherein the compound is of the formula: ##STR11## wherein R and Y have the meanings defined in claim 1; R 3 is selected from the group consisting of alkane-poly-yl containing from 3 to 6 carbon atoms and from 2 to 6 univalent bonds and 1,2,3,4,5,6-cyclohexanehexayl; and q is an integer of from 2 to 6.
Claim 5
Independent Claim
127 words
A method of reducing the lipid concentration in the blood of a patient in need thereof which comprises orally or parenterally administering to said patient a blood lipid lowering effective amount of a compound of the formula: ##STR12## wherein Y is selected from the group consisting of oxygen and divalent sulfur; R is selected from the group consisting of a straight or branched saturated hydrocarbon chain containing from 10 to 20 carbon atoms and a straight or branched unsaturated hydrocarbon chain containing from 10 to 20 carbon atoms and from 1 to 4 double bonds; R 2 is selected from the group consisting of hydrogen, a straight or branched lower alkyl group of from 1 to 6 carbon atoms, benzyl and phenethyl; or pharmaceutically acceptable salts thereof.
Claim 6
Independent Claim
127 words
A method of reducing the lipid concentration in the blood of a patient in need thereof which comprises orally or parenterally administering to said patient a blood lipid lowering effective amount of a compound of the formula: ##STR12## wherein Y is selected from the group consisting of oxygen and divalent sulfur; R is selected from the group consisting of a straight or branched saturated hydrocarbon chain containing from 10 to 20 carbon atoms and a straight or branched unsaturated hydrocarbon chain containing from 10 to 20 carbon atoms and from 1 to 4 double bonds; R 2 is selected from the group consisting of hydrogen, a straight or branched lower alkyl group of from 1 to 6 carbon atoms, benzyl and phenethyl; or pharmaceutically acceptable salts thereof.
Claim 7
Dependent Claim
22 words
The method of claim 4 wherein R represents a straight or branched saturated hydrocarbon chain containing from 10 to 20 carbon atoms.
Claim 8
Dependent Claim
16 words
The method of claim 5 wherein the compound is 5-(tetradecyloxy)-2-thiophenecarboxylic acid or pharmaceutically acceptable salts thereof.
Claim 9
Dependent Claim
16 words
The method of claim 5 wherein the compound is 5-(tetradecylthio)-2-thiophenecarboxylic acid or pharmaceutically acceptable salts thereof.
Claim 10
Dependent Claim
13 words
The method of claim 5 wherein the compound is 5-(tetradecyloxy)-2-thiophenecarboxylic acid benzyl ester.
Claim 11
Dependent Claim
13 words
The method of claim 5 wherein the compound is 5-(tetradecylthio)-2-thiophenecarboxylic acid benzyl ester.
Claim 12
Dependent Claim
29 words
The method of claim 4 wherein R is a straight or branched unsaturated hydrocarbon chain containing from 10 to 20 carbon atoms and from 1 to 4 double bonds.
Claim 13
Dependent Claim
177 words
A pharmaceutical composition in unit dosage form containing from about 50 milligrams to 1 gram of a compound of the formula: ##STR13## wherein Y is selected from the group consisting of oxygen and divalent sulfur; R is selected from the group consisting of a straight or branched saturated hydrocarbon chain containing from 10 to 20 carbon atoms and a straight or branched unsaturated hydrocarbon chain containing from 10 to 20 carbon atoms and from 1 to 4 double bonds; R 1 is selected from the group consisting of hydrogen, a straight or branched lower alkyl group of from 1 to 6 carbon atoms, benzyl, phenethyl, alkane-poly-yl containing from 3 to 6 carbon atoms and from 2 to 6 univalent bonds, and 1,2,3,4,5,6-cyclohexanehexayl; X is an integer of from 1 to 6 with the proviso that when R 1 is alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to from 2 to 6 and when R 1 is other than alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to 1; or pharmaceutically acceptable salts; and a significant amount of a pharmaceutical carrier.
Claim 14
Dependent Claim
177 words
A pharmaceutical composition in unit dosage form containing from about 50 milligrams to 1 gram of a compound of the formula: ##STR13## wherein Y is selected from the group consisting of oxygen and divalent sulfur; R is selected from the group consisting of a straight or branched saturated hydrocarbon chain containing from 10 to 20 carbon atoms and a straight or branched unsaturated hydrocarbon chain containing from 10 to 20 carbon atoms and from 1 to 4 double bonds; R 1 is selected from the group consisting of hydrogen, a straight or branched lower alkyl group of from 1 to 6 carbon atoms, benzyl, phenethyl, alkane-poly-yl containing from 3 to 6 carbon atoms and from 2 to 6 univalent bonds, and 1,2,3,4,5,6-cyclohexanehexayl; X is an integer of from 1 to 6 with the proviso that when R 1 is alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to from 2 to 6 and when R 1 is other than alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to 1; or pharmaceutically acceptable salts; and a significant amount of a pharmaceutical carrier.
Claim 15
Dependent Claim
9 words
The composition of claim 11 wherein Y is oxygen.
Claim 16
Dependent Claim
9 words
The composition of claim 11 wherein Y is sulfur.
Claim 17
Dependent Claim
56 words
The composition of claim 11 wherein the compound is of the formula: ##STR14## wherein Y and R have the meanings defined in claim 11; R 2 is selected from the group consisting of hydrogen, a straight or branched lower alkyl group of from 1 to 6 carbon atoms, benzyl and phenethyl; or pharmaceutically acceptable salts thereof.
Claim 18
Dependent Claim
60 words
The composition of claim 11 wherein the compound is of the formula: ##STR15## wherein Y and R have the meanings defined in claim 11; R 3 is selected from the group consisting of alkane-poly-yl containing from 3 to 6 carbon atoms and from 2 to 6 univalent bonds and 1,2,3,4,5,6-cyclohexanehexayl; and q is an integer of from 2 to 6.
Claim 19
Dependent Claim
118 words
A pharmaceutical composition in unit dosage form containing from 50 milligrams to 1 gram of a compound of the formula: ##STR16## wherein Y is selected from the group consisting of oxygen and divalent sulfur; R is selected from the group consisting of a straight or branched saturated hydrocarbon chain containing from 10 to 20 carbon atoms and a straight or branched unsaturated hydrocarbon chain containing from 10 to 20 carbon atoms and from 1 to 4 double bonds; R 2 is selected from the group consisting of hydrogen, a straight or branched lower alkyl group of from 1 to 6 carbon atoms, benzyl and phenethyl; or pharmaceutically acceptable salts thereof; and a significant amount of a pharmaceutical carrier.
Claim 20
Dependent Claim
118 words
A pharmaceutical composition in unit dosage form containing from 50 milligrams to 1 gram of a compound of the formula: ##STR16## wherein Y is selected from the group consisting of oxygen and divalent sulfur; R is selected from the group consisting of a straight or branched saturated hydrocarbon chain containing from 10 to 20 carbon atoms and a straight or branched unsaturated hydrocarbon chain containing from 10 to 20 carbon atoms and from 1 to 4 double bonds; R 2 is selected from the group consisting of hydrogen, a straight or branched lower alkyl group of from 1 to 6 carbon atoms, benzyl and phenethyl; or pharmaceutically acceptable salts thereof; and a significant amount of a pharmaceutical carrier.
Claim 21
Dependent Claim
16 words
The composition of claim 16 wherein the compound is 5-tetradecyloxy)-2-thiophenecarboxylic acid or pharmaceutically acceptable salts thereof.
Claim 22
Dependent Claim
13 words
The composition of claim 16 wherein the compound is 5-tetradecyloxy)-2-thiophenecarboxylic acid benzyl ester.
Claim 23
Dependent Claim
11 words
The composition of claim 16 wherein the compound is 5-(tetradecylthio)-2-thiophenecarboxylic acid.
Claim 24
Dependent Claim
13 words
The composition of claim 16 wherein the compound is 5-(tetradecylthio)-2-thiophenecarboxylic acid benzyl ester.
References Cited (Backward Citations)
US2462697A
Cited
US3360527A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-07 | 1980-09-06 | 1981-03-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-07 | 1984-09-06 | 1985-03-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-07 | 1988-09-06 | 1989-03-08 | $7700.00 | Window Closed / Lapsed |