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US4465679A Expired / Lapsed US ⏱️ 0.0 years remaining

1,2-Diaza-3-one compounds, their use in treating hypertension and pharmaceutical compositions thereof

Assignee: USV Pharmaceutical Corp
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Filing: 1983-01-31
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Granted: 1984-08-14
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Expires: 2003-01-31
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Abstract

Abstract Compounds of the formula ##STR1## and their pharmaceutically-acceptable salts, wherein the substituents are as defined herein, having antihypertensive activity.

Inventors

  • 👤 Fu-chih Huang
  • 👤 Howard Jones
  • 👤 Wan-kit Chan

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 09:20
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/02; C07K5/022; C07K5/0222; A; A61; A61K; A61K38/00

Claims Analysis

Total Claims: 37
Claim 1
Independent Claim 287 words
A compound of the formula and its pharmaceutically-acceptable acid addition salts, wherein X is a saturated chain of 1 to 5 carbon atoms; A and A' are independently hydroxy, alkoxy, phenoxy, or hydroxyamino; R 1 , R 2 , R 3 , R 4 , R 6 and R 7 are independently hydrogen, alkyl, alkenyl, alkynyl, phenyl, phenylalkyl, fused cycloalkyl-phenyl, fused phenyl-cycloalkyl, fused cycloalkylphenyl-alkyl, fused phenyl-cycloalkyl-alkyl, phenoxyalkyl, phenylalkyloxyalkyl, cycloalkyl, or cycloalkyl-alkyl, and R 4 can in addition be keto-oxygen or, when X contains at least 2 carbon atoms, R 4 can be a phenyl ring fused to 2 consecutive atoms of X or a cycloalkyl ring fused to X; and R 5 can be hydrogen, alkyl, alkenyl, alkynyl, alkanoyl, benzoyl, phenyl-alkanoyl, carbamoyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, phenyl, phenylalkyl, polyphenyl, fused cycloalkyl-phenyl, fused phenyl-cycloalkyl, fused phenyl-cyclo-alkyl-alkyl, or fused cycloalkyl-phenyl-alkyl; wherein the alkyl, alkoxy, alkenoxy, alkenyl, and alkynyl groups can carry one or more substituents selected from the group consisting of hydroxy, alkanoyloxy, benzoyloxy, phenylalkanoyl, carbamoyl, phenyl, alkoxy, phenoxy, amino, mono- or dialkylamino, alkanoylamino, benzoylamino, mercapto, mercaptoalkyl, and alkylthio; the cycloalkyl rings can carry one or more substituents selected from the group consisting of alkyl, hydroxy, alkylamino, and nitro; and the phenyl rings can carry one or more substituents selected from the group consisting of carboxylic acid, cyano, carboxy-lower alkoxy, alkyl, hydroxy, alkoxy, hydroxyalkyl, halo, trifluoroalkyl, mercapto, alkylthio, mercaptoalkyl, amino, alkylamino, aminoalkyl, nitro, methylenedioxy, and sulfamyl; wherein the alkyl groups and moieties contain 1 to 9 carbon atoms; the alkenyl and alkynyl groups and moieties contain 2 to 9 carbon atoms; the polycycloalkyl groups have up to 20 carbon atoms; and the cycloalkyl groups and the cycloalkyl portions of substituents containing cycloalkyl groups contain 3 to 9 carbon atoms.
Claim 2
Dependent Claim 287 words
A compound of the formula and its pharmaceutically-acceptable acid addition salts, wherein X is a saturated chain of 1 to 5 carbon atoms; A and A' are independently hydroxy, alkoxy, phenoxy, or hydroxyamino; R 1 , R 2 , R 3 , R 4 , R 6 and R 7 are independently hydrogen, alkyl, alkenyl, alkynyl, phenyl, phenylalkyl, fused cycloalkyl-phenyl, fused phenyl-cycloalkyl, fused cycloalkylphenyl-alkyl, fused phenyl-cycloalkyl-alkyl, phenoxyalkyl, phenylalkyloxyalkyl, cycloalkyl, or cycloalkyl-alkyl, and R 4 can in addition be keto-oxygen or, when X contains at least 2 carbon atoms, R 4 can be a phenyl ring fused to 2 consecutive atoms of X or a cycloalkyl ring fused to X; and R 5 can be hydrogen, alkyl, alkenyl, alkynyl, alkanoyl, benzoyl, phenyl-alkanoyl, carbamoyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, phenyl, phenylalkyl, polyphenyl, fused cycloalkyl-phenyl, fused phenyl-cycloalkyl, fused phenyl-cyclo-alkyl-alkyl, or fused cycloalkyl-phenyl-alkyl; wherein the alkyl, alkoxy, alkenoxy, alkenyl, and alkynyl groups can carry one or more substituents selected from the group consisting of hydroxy, alkanoyloxy, benzoyloxy, phenylalkanoyl, carbamoyl, phenyl, alkoxy, phenoxy, amino, mono- or dialkylamino, alkanoylamino, benzoylamino, mercapto, mercaptoalkyl, and alkylthio; the cycloalkyl rings can carry one or more substituents selected from the group consisting of alkyl, hydroxy, alkylamino, and nitro; and the phenyl rings can carry one or more substituents selected from the group consisting of carboxylic acid, cyano, carboxy-lower alkoxy, alkyl, hydroxy, alkoxy, hydroxyalkyl, halo, trifluoroalkyl, mercapto, alkylthio, mercaptoalkyl, amino, alkylamino, aminoalkyl, nitro, methylenedioxy, and sulfamyl; wherein the alkyl groups and moieties contain 1 to 9 carbon atoms; the alkenyl and alkynyl groups and moieties contain 2 to 9 carbon atoms; the polycycloalkyl groups have up to 20 carbon atoms; and the cycloalkyl groups and the cycloalkyl portions of substituents containing cycloalkyl groups contain 3 to 9 carbon atoms.
Claim 3
Dependent Claim 12 words
A compound or salt of claim 1 having an (S,S,S) structural configuration.
Claim 4
Dependent Claim 82 words
A compound of the formula: ##STR27## wherein X represents a chain of from 1 to 5 unsubstituted methylene groups; R 1 represents an alkyl group containing 1 to 6 carbon atoms, phenyl, phenylalkyl wherein the alkyl group contains from 1 to 6 carbon atoms, or alkylamine wherein the alkyl group contains from 1 to 6 carbon atoms; and R 5 represents hydrogen, alkyl containing 1 to 6 carbon atoms, phenyl, or phenylalkyl wherein the alkyl group contains 1 to 6 carbon atoms.
Claim 5
Dependent Claim 82 words
A compound of the formula: ##STR27## wherein X represents a chain of from 1 to 5 unsubstituted methylene groups; R 1 represents an alkyl group containing 1 to 6 carbon atoms, phenyl, phenylalkyl wherein the alkyl group contains from 1 to 6 carbon atoms, or alkylamine wherein the alkyl group contains from 1 to 6 carbon atoms; and R 5 represents hydrogen, alkyl containing 1 to 6 carbon atoms, phenyl, or phenylalkyl wherein the alkyl group contains 1 to 6 carbon atoms.
Claim 6
Dependent Claim 12 words
A compound or salt of claim 3 having an (S,S,S) structural configuration.
Claim 7
Dependent Claim 10 words
The compound according to claim 3 which is 4-(1-carbethoxy-3-phenylpropyl-1-amino)-1,2-diazapin-3-one-2-acetic acid.
Claim 8
Dependent Claim 10 words
The compound according to claim 3 which is 4-(1-carbethoxy-3-phenylpropyl-1-amino)-1-phenyl-1,2-diazapin-3-one-2-acetic acid.
Claim 9
Dependent Claim 10 words
The compound according to claim 3 which is 4-(1-carbethoxy-3-phenylpropyl-1-amino)-1-ethyl-1,2-diazapin-3-one-2-acetic acid.
Claim 10
Dependent Claim 10 words
The compound according to claim 3 which is 4-(1-carbethoxy-ethyl-1-amino)-1,2-diazapin-3-one-2-acetic acid.
Claim 11
Dependent Claim 10 words
The compound according to claim 3 which is 4-(1-carbethoxy-4-aminobutyl-1-amino)-1,2-diazapin-3-one-2-acetic acid.
Claim 12
Dependent Claim 10 words
The compound according to claim 3 which is 4-(1-carbethoxy-3-phenylpropyl-1-amino)-hexahydropyridazine-3-one-2-acetic acid.
Claim 13
Dependent Claim 10 words
The compound according to claim 3 which is 4-(1-carbethoxy-3-phenylpropyl-1-amino)-1,2-diazocine-3-one-2-acetic acid.
Claim 14
Dependent Claim 32 words
A pharmaceutically-acceptable acid salt of a compound according to claim 3 wherein the acid is selected from the group consisting of hydrochloric, hydrobromic, sulfuric, nitric, acetic, fumaric, malic, maleic and citric acids.
Claim 15
Dependent Claim 32 words
A pharmaceutically-acceptable acid salt of a compound according to claim 5 wherein the acid is selected from the group consisting of hydrochloric, hydrobromic, sulfuric, nitric, acetic, fumaric, malic, maleic and citric acids.
Claim 16
Dependent Claim 32 words
A pharmaceutically-acceptable acid salt of a compound according to claim 6 wherein the acid is selected from the group consisting of hydrochloric, hydrobromic, sulfuric, nitric, acetic, fumaric, malic, maleic and citric acids.
Claim 17
Dependent Claim 32 words
A pharmaceutically-acceptable acid salt of a compound according to claim 7 wherein the acid is selected from the group consisting of hydrochloric, hydrobromic, sulfuric, nitric, acetic, fumaric, malic, maleic and citric acids.
Claim 18
Dependent Claim 32 words
A pharmaceutically-acceptable acid salt of a compound according to claim 8 wherein the acid is selected from the group consisting of hydrochloric, hydrobromic, sulfuric, nitric, acetic, fumaric, malic, maleic and citric acids.
Claim 19
Dependent Claim 32 words
A pharmaceutically-acceptable acid salt of a compound according to claim 9 wherein the acid is selected from the group consisting of hydrochloric, hydrobromic, sulfuric, nitric, acetic, fumaric, malic, maleic and citric acids.
Claim 20
Dependent Claim 32 words
A pharmaceutically-acceptable acid salt of a compound according to claim 10 wherein the acid is selected from the group consisting of hydrochloric, hydrobromic, sulfuric, nitric, acetic, fumaric, malic, maleic and citric acids.
Claim 21
Dependent Claim 32 words
A pharmaceutically-acceptable acid salt of a compound according to claim 11 wherein the acid is selected from the group consisting of hydrochloric, hydrobromic, sulfuric, nitric, acetic, fumaric, malic, maleic and citric acids.
Claim 22
Dependent Claim 25 words
The method of alleviating hypertension in a host suffering therefrom comprising administering to said host an antihypertensive effect amount of a salt of claim 12.
Claim 23
Dependent Claim 25 words
The method of alleviating hypertension in a host suffering therefrom comprising administering to said host an antihypertensive effect amount of a salt of claim 13.
Claim 24
Dependent Claim 25 words
The method of alleviating hypertension in a host suffering therefrom comprising administering to said host an antihypertensive effect amount of a salt of claim 14.
Claim 25
Dependent Claim 25 words
The method of alleviating hypertension in a host suffering therefrom comprising administering to said host an antihypertensive effect amount of a salt of claim 15.
Claim 26
Dependent Claim 25 words
The method of alleviating hypertension in a host suffering therefrom comprising administering to said host an antihypertensive effect amount of a salt of claim 16.
Claim 27
Dependent Claim 25 words
The method of alleviating hypertension in a host suffering therefrom comprising administering to said host an antihypertensive effect amount of a salt of claim 17.
Claim 28
Dependent Claim 25 words
The method of alleviating hypertension in a host suffering therefrom comprising administering to said host an antihypertensive effect amount of a salt of claim 18.
Claim 29
Dependent Claim 25 words
The method of alleviating hypertension in a host suffering therefrom comprising administering to said host an antihypertensive effect amount of a salt of claim 19.
Claim 30
Dependent Claim 24 words
An antihypertensive pharmaceutical preparation comprising about 0.1 to about 500 milligrams of a compound according to claim 3 in association with a pharmaceutically-acceptable carrier.
Claim 31
Dependent Claim 24 words
An antihypertensive pharmaceutical preparation comprising about 0.1 to about 500 milligrams of a compound according to claim 5 in association with a pharmaceutically-acceptable carrier.
Claim 32
Dependent Claim 24 words
An antihypertensive pharmaceutical preparation comprising about 0.1 to about 500 milligrams of a compound according to claim 6 in association with a pharmaceutically-acceptable carrier.
Claim 33
Dependent Claim 24 words
An antihypertensive pharmaceutical preparation comprising about 0.1 to about 500 milligrams of a compound according to claim 7 in association with a pharmaceutically-acceptable carrier.
Claim 34
Dependent Claim 24 words
An antihypertensive pharmaceutical preparation comprising about 0.1 to about 500 milligrams of a compound according to claim 8 in association with a pharmaceutically-acceptable carrier.
Claim 35
Dependent Claim 24 words
An antihypertensive pharmaceutical preparation comprising about 0.1 to about 500 milligrams of a compound according to claim 9 in association with a pharmaceutically-acceptable carrier.
Claim 36
Dependent Claim 24 words
An antihypertensive pharmaceutical preparation comprising about 0.1 to about 500 milligrams of a compound according to claim 10 in association with a pharmaceutically-acceptable carrier.
Claim 37
Dependent Claim 24 words
An antihypertensive pharmaceutical preparation comprising about 0.1 to about 500 milligrams of a compound according to claim 11 in association with a pharmaceutically-acceptable carrier.

References Cited (Backward Citations)

US4409146A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-08-14 1988-02-13 1988-08-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-08-14 1992-02-13 1992-08-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-08-14 1996-02-13 1996-08-14 $7700.00 Window Closed / Lapsed

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