US3965257A
Expired / Lapsed
US
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Compositions and methods for the treatment of the symptoms of histamine induced allergic reactions
Assignee: Richardson Vicks Inc
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Filing: 1974-01-28
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Granted: 1976-06-22
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Expires: 1994-01-28
Abstract
Abstract Novel compounds useful as antihistamine agents, antiallergy agents, and bronchodilators are represented by the following formula ##SPC1## Wherein R represents hydrogen or hydroxy; R 1 represents hydrogen; or R and R 1 taken together form a second bond between the carbon atoms bearing R and R 1 ; n is a positive whole integer of from 1 to 3; Z represents thienyl, phenyl, or substituted phenyl wherein the substituents on the substituted phenyl may be attached at the ortho, meta, or para positions of the phenyl ring and are selected from halogen, a straight or branched lower alkyl chain of from 1 to 4 carbon atoms, a lower alkoxy group of from 1 to 4 carbon atoms, di(lower)alkylamino, or a saturated monocyclic heterocyclic group such as pyrrolidino, piperidino, morpholino, or N-(lower)alkylpiperazino. Pharmaceutically acceptable acid addition salts and individual optical isomers of compounds of the above formula are also included as a part of this invention.
Inventors
- 👤 Albert A. Carr
- 👤 C. Richard Kinsolving
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 22:19
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/435; A61K31/44; A61K31/445
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
151 words
A pharmaceutical composition in unit dosage form containing from about 1 to 5 milligrams of a compound of the formula ##SPC6## wherein R is selected from the group consisting of hydrogen and hydroxy; n is a positive integer of from 1 to 3; and Z is selected from the group consisting of thienyl, phenyl, and substituted phenyl wherein the substituents on the substituted phenyl may be attached at the ortho, meta, or para positions of the substituted phenyl ring and are selected from the group consisting of a halogen atom, a straight or branched alkyl chain of from 1 to 4 carbon atoms, a lower alkoxy group of from 1 to 4 carbon atoms, a di(lower)alkylamino group, and a saturated monocyclic heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, morpholino, and N-(lower)alkylpiperazino; and a pharmaceutically acceptable acid addition salt thereof and a significant amount of a pharmaceutically acceptable carrier.
Claim 2
Dependent Claim
151 words
A pharmaceutical composition in unit dosage form containing from about 1 to 5 milligrams of a compound of the formula ##SPC6## wherein R is selected from the group consisting of hydrogen and hydroxy; n is a positive integer of from 1 to 3; and Z is selected from the group consisting of thienyl, phenyl, and substituted phenyl wherein the substituents on the substituted phenyl may be attached at the ortho, meta, or para positions of the substituted phenyl ring and are selected from the group consisting of a halogen atom, a straight or branched alkyl chain of from 1 to 4 carbon atoms, a lower alkoxy group of from 1 to 4 carbon atoms, a di(lower)alkylamino group, and a saturated monocyclic heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, morpholino, and N-(lower)alkylpiperazino; and a pharmaceutically acceptable acid addition salt thereof and a significant amount of a pharmaceutically acceptable carrier.
Claim 3
Dependent Claim
13 words
A composition of claim 1 wherein R represents hydroxy and n is 3.
Claim 4
Dependent Claim
18 words
A composition of claim 2 wherein the compound is 4'-tert-butyl-4-[4-(α-hydrozy-α-phenylbenzyl)piperidino]butyrophenone or a pharmaceutically acceptable acid addition salt thereof.
Claim 5
Dependent Claim
18 words
A composition of claim 2 wherein the compound is 4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-4'methoxybutyrophenone or a pharmaceutically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
18 words
A composition of claim 2 wherein the compound is 4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-1-(2-thienyl)-1-butanone or a pharmaceutically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
18 words
A composition of claim 2 wherein the compound is 4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-4'-piperidinobutyrophenone or a pharmaceutically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
18 words
A composition of claim 2 wherein the compound is 4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone or a pharmaceutically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
18 words
A composition of claim 2 wherein the compound is 4'-fluoro-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-butyrophenone or a pharmaceutically acceptable acid addition salt thereof.
Claim 10
Dependent Claim
18 words
A composition of claim 2 wherein the compound is 4'-ethyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-butyrophenone or a pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
19 words
A composition of claim 2 wherein the compound is 4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-4'-methylbutyrophenone hydrochloride or a pharmaceutically acceptable acid addition salt thereof.
Claim 12
Dependent Claim
15 words
A composition of claim 1 wherein said composition is in the form of a solid.
Claim 13
Dependent Claim
15 words
A composition of claim 1 wherein said composition is in a form suitable for injection.
Claim 14
Dependent Claim
15 words
A composition of claim 1 wherein said composition is in the form of an aerosol.
Claim 15
Independent Claim
156 words
A method of treating the symptoms of an allergic reaction due to histamine in a patient comprising administering to said patient from 0.01 to 20 milligrams per kilogram of body weight of the patient a compound of the formula: ##SPC7## wherein R is selected from the group consisting of hydrogen and hydroxy; n is a positive integer of from 1 to 3; and Z is selected from the group consisting of thienyl, phenyl, and substituted phenyl wherein the substituents on the substituted phenyl amy be attached at the ortho, meta, or para positions of the substituted phenyl ring and are selected from the group consisting of a halogen atom, a straight or branched alkyl chain of from 1 to 4 carbon atoms, a lower alkoxy group of from 1 to 4 carbon atoms, a di(lower) alkylamino group, and a saturated monocyclic heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, morpholino, and N-(lower)alkylpiperazino; and a
Claim 16
Independent Claim
156 words
A method of treating the symptoms of an allergic reaction due to histamine in a patient comprising administering to said patient from 0.01 to 20 milligrams per kilogram of body weight of the patient a compound of the formula: ##SPC7## wherein R is selected from the group consisting of hydrogen and hydroxy; n is a positive integer of from 1 to 3; and Z is selected from the group consisting of thienyl, phenyl, and substituted phenyl wherein the substituents on the substituted phenyl amy be attached at the ortho, meta, or para positions of the substituted phenyl ring and are selected from the group consisting of a halogen atom, a straight or branched alkyl chain of from 1 to 4 carbon atoms, a lower alkoxy group of from 1 to 4 carbon atoms, a di(lower) alkylamino group, and a saturated monocyclic heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, morpholino, and N-(lower)alkylpiperazino; and a
Claim 17
Dependent Claim
10 words
A method of claim 15 wherein the compound is 4'-fluoro-2-[4-(α-hydroxy-α-phenylbenzyl)piperidino]acetopheno
Claim 18
Dependent Claim
10 words
A method of claim 17 wherein the compound is 4'-tert-butyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyro
Claim 19
Dependent Claim
10 words
A method of claim 17 wherein the compound is 4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-4'-methoxybutyrophe
Claim 20
Dependent Claim
10 words
A method of claim 17 wherein the compound is 4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-1-(2-thienyl)-1-but
Claim 21
Dependent Claim
10 words
A method of claim 17 wherein the compound is 4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-4'-piperidinobutyro
Claim 22
Dependent Claim
12 words
A method of claim 17 wherein the compound is 4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone or a
Claim 23
Dependent Claim
10 words
A method of claim 17 wherein the compound is 4'-fluoro-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino[-butyrophe
Claim 24
Dependent Claim
10 words
A method of claim 17 wherein the compound is 4'-ethyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-butyrophen
Claim 25
Dependent Claim
18 words
A method of claim 17 wherein the compound is 4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-4'-methylbutyrophenone hydrochloride or a pharmaceutically acceptable acid addition salt
Claim 26
Independent Claim
153 words
A method of inducing bronchial dilation in a patient suffering from bronchial constriction comprising administering to said patient from 0.01 to 20 milligrams per kilogram of body weight of the patient of a compound of the formula ##SPC8## wherein R is selected from the group consisting of hydrogen and hydroxy; n is a positive integer of from 1 to 3; and Z is selected from the group consisting of thienyl, phenyl, and substituted phenyl wherein the substituents on the substituted phenyl may be attached at the ortho, meta, or para positions of the substituted phenyl ring and are selected from the group consisting of a halogen atom, a straight or branched alkyl chain of from 1 to 4 carbon atoms, a lower alkoxy group of from 1 to 4 carbon atoms, a di(lower)alkylamino group, and a saturated monocyclic heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, morpholino, and N-(lower)alkylpiperazino; and a
Claim 27
Independent Claim
153 words
A method of inducing bronchial dilation in a patient suffering from bronchial constriction comprising administering to said patient from 0.01 to 20 milligrams per kilogram of body weight of the patient of a compound of the formula ##SPC8## wherein R is selected from the group consisting of hydrogen and hydroxy; n is a positive integer of from 1 to 3; and Z is selected from the group consisting of thienyl, phenyl, and substituted phenyl wherein the substituents on the substituted phenyl may be attached at the ortho, meta, or para positions of the substituted phenyl ring and are selected from the group consisting of a halogen atom, a straight or branched alkyl chain of from 1 to 4 carbon atoms, a lower alkoxy group of from 1 to 4 carbon atoms, a di(lower)alkylamino group, and a saturated monocyclic heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, morpholino, and N-(lower)alkylpiperazino; and a
Claim 28
Dependent Claim
15 words
A method of claim 26 wherein R is hydroxy and n is equal to 3.
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) | 1979-06-22 | 1979-12-22 | 1980-06-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-22 | 1983-12-22 | 1984-06-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-22 | 1987-12-22 | 1988-06-22 | $7700.00 | Window Closed / Lapsed |