Patent US3689663A successfully refreshed from Google Patents.
US3689663A
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Lowering cholesterol blood levels with flavanoids
Assignee: Merck KGaA
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Filing: 1969-04-02
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Granted: 1972-09-05
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Expires: 1989-04-02
Abstract
Abstract A method of effecting a cholesterol-level-decreasing effect in blood, and also pharmaceutical compositions, are both based on substituted flavanoids of the following formula, as well as their acid addition salts and quaternary ammonium derivatives: WHEREIN R1 and R2 are identical or different and can represent OH; alkoxy of one to 10 carbon atoms and if desired substituted by other moieties; tetrahydropyranyl-(2)-oxy; acyloxy of one to six carbon atoms; NO2; NH2; alkylated NH2 having one to eight carbon atoms; or acylamino of two to six carbon atoms; R3 can represent H; OH; alkyl and alkoxy of one to three carbon atoms; NH2; or Hal; R4 can represent O; H, OH; H, H; or N, NH2; R5 can represent H or R1; Hal can represent Cl; Br; or I; R2 and R5 together can also represent methylene dioxy; ethylene dioxy; or propylene dioxy; and wherein, in the 2,3-position, an additional double bond can be present.
Inventors
- 👤 Josef Kramer
- 👤 Klaus Irmscher
- 👤 Hans-Otto Voge
- 👤 Herbert Halpaap
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 01:56
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/22; C07D311/26; C07D311/28; C07D311/32
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
12 words
A pharmaceutical composition as defined by claim 1, wherein R3 is hydroxy.
Claim 2
Dependent Claim
114 words
A pharmaceutical composition as defined by claim 1, wherein R1 OH; acyloxy of one to six carbon atoms, the acyl portion being derived from a carboxylic acid; alkoxy of one to six carbon atoms; or alkoxy of one to six carbon atoms in the alkoxy chain substituted by carbalkoxy of two to nine carbon atoms or by pyrrolidinocarbonyl; R2 alkoxy of one to six carbon atoms; or, together with R5, methylenedioxy; R3 alkyl of one to three carbon atoms; or alkoxy of one to three carbon atoms; R4 H2 or O; R5 H or OCH3 or, together with R2, methylenedioxy; and wherein the 2,3-position of said compound is optionally connected by a double bond.
Claim 3
Dependent Claim
14 words
A pharmaceutical composition as defined by claim 1, wherein said compound is 6,3'',4''-trimethoxy flavonol.
Claim 4
Dependent Claim
250 words
A process of lowering the level of cholesterol in the blood of mammals, which process comprises administering an effective cholesterol-level-lowering amount of a compound selected from the group consisting of a flavanoid, an acid addition salt thereof, and a quaternary ammonium derivative thereof, said flavanoid having the formula wherein R1 and R2 are each selected from the group consisting of OH; alkoxy of one to 10 carbon atoms; tetrahydropyranyl-(2)-oxy; acyloxy of 1-6 carbon atoms wherein the acyl portion is derived from a hydrocarbon carboxylic acid; NO2; NH2; alkylated NH2 having one to eight carbon atoms; acylamino of two to six carbon atoms wherein the acyl portion is derived from a hydrocarbon carboxylic acid; an alkoxy group of one to 10 carbon atoms in the alkoxy chain substituted by a member of the group consisting of phenyl; amino; alkylated amino of one to nine carbon atoms; pyrrolidino; carboxy; carbalkoxy of two to nine carbon atoms; cyano; carboxamido; dialkylcarboxamido of three to nine carbon atoms; pyrrolidinocarbonyl; and (2-hydroxyethylamino)-carbonyl; R2 together with R5 is selected from the group consisting of methylene dioxy, ethylene dioxy, and propylene dioxy; R3 is selected from the group consisting of H; OH; alkyl of 1-3 carbon atoms; alkoxy of one to three carbon atoms; NH2; Cl; Br; and I; R4 is selected from the group consisting of O; H,OH; H,H; and H, NH2; R5 is selected from the group consisting of H and R1; and wherein the 2,3-position of said flavanoid is optionally connected by a double bond.
Claim 5
Dependent Claim
11 words
A process as defined by claim 5, wherein R3 is hydroxy.
Claim 6
Dependent Claim
111 words
A process as defined by claim 5, wherein R1 OH; acyloxy of one to six carbon atoms, the acyl portion being derived from a carboxylic acid; Alkoxy of one to six carbon atoms; or alkoxy of one to six carbon atoms in the alkoxy chain substituted by carbalkoxy of 2-9 carbon atoms or by pyrrolidinocarbonyl; R2 alkoxy of one to six carbon atoms; or, together with R5, methylenedioxy; R3 alkyl of one to three carbon atoms; or alkoxy of one to three carbon atoms; R4 H2 or O; R5 H or OCH3 or, together with R2, methylenedioxy; and wherein the 2,3-position of said compound is optionally connected by a double bond.
Claim 7
Dependent Claim
11 words
A process as defined by claim 5, wherein R4 is H2.
Claim 8
Dependent Claim
51 words
A process as defined by claim 8, wherein R1 is OH or acyloxy of one to six carbon atoms, the acyl portion being derived from a carboxylic acid; R2 is methoxy; R3 is alkyl or alkoxy of one to three carbon atoms; R4 is H2 or O; and R5 is H.
Claim 9
Dependent Claim
14 words
A process as defined by claim 5, wherein said compound is 6, 3'',4''-trimethoxy flavonol.
References Cited (Backward Citations)
US3453282A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1975-09-05 | 1976-03-06 | 1976-09-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-09-05 | 1980-03-06 | 1980-09-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-09-05 | 1984-03-06 | 1984-09-05 | $7700.00 | Window Closed / Lapsed |