US4021552A
Expired / Lapsed
US
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10-[ω-(BENZOYLPIPERIDINYL)ALKYL]PHENOTHIAZINES
Assignee: AH Robins Co Inc
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Filing: 1976-04-20
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Granted: 1977-05-03
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Expires: 1996-04-20
Abstract
Abstract 10-[ω-(Benzoylpiperidinyl)alkyl]phenothiazines having the formula ##STR1## wherein R is hydrogen, chloro, bromo, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl, or dimethylsulfamoyl, R 1 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, lower alkyl or lower alkoxy and n is 2, 3 or 4 are disclosed. Methods for the preparation of the compounds are described. The compounds possess tranquilizing activity and are useful as tranquilizing agents in mammals.
Inventors
- 👤 William J. Welstead, Jr.
- 👤 Robert F. Boswell, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 10:08
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/30; C07D211/32; A; A61; A61P; A61P25/00; A61P25/04; A61P25/20
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
11 words
A compound selected from 10-[ω-(benzoylpiperidinyl)alkyl] phenothiazines having the formula: ##STR7## wherein;
Claim 2
Dependent Claim
11 words
A compound selected from 10-[ω-(benzoylpiperidinyl)alkyl] phenothiazines having the formula: ##STR7## wherein;
Claim 3
Dependent Claim
53 words
R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl, or dimethylsulfamoyl, R 1 is selected from the group consisting of hydrogen, chloro, bromo, fluoro, trifluoromethyl, lower alkoxy, or lower alkyl, n is a positive integer from 2-4 inclusive, and non-toxic pharmaceutically acceptable acid addition salts thereof.
Claim 4
Dependent Claim
53 words
R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl, or dimethylsulfamoyl, R 1 is selected from the group consisting of hydrogen, chloro, bromo, fluoro, trifluoromethyl, lower alkoxy, or lower alkyl, n is a positive integer from 2-4 inclusive, and non-toxic pharmaceutically acceptable acid addition salts thereof.
Claim 5
Dependent Claim
37 words
A compound selected from 10-[3-(benzoylpiperidinyl)propyl] phenothiazines having the formula: ##STR8## wherein; R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl or dimethylsulfamoyl, and non-toxic pharamaceutically acceptable acid addition salts thereof.
Claim 6
Dependent Claim
37 words
A compound selected from 10-[3-(benzoylpiperidinyl)propyl] phenothiazines having the formula: ##STR8## wherein; R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl or dimethylsulfamoyl, and non-toxic pharamaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim
37 words
A compound selected from 10-[3-(benzoylpiperidinyl)propyl] phenothiazines having the formula: ##STR9## wherein; R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl or dimethylsulfamoyl, and non-toxic pharmaceutically acceptable acid addition salts thereof.
Claim 8
Dependent Claim
37 words
A compound selected from 10-[3-(benzoylpiperidinyl)propyl] phenothiazines having the formula: ##STR9## wherein; R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl or dimethylsulfamoyl, and non-toxic pharmaceutically acceptable acid addition salts thereof.
Claim 9
Dependent Claim
8 words
The compound of claim 3 which is 10-{3-[4-(p-fluorobenzoyl)-piperidinyl]propyl}phenothiazine.
Claim 10
Dependent Claim
8 words
The compound of claim 3 which is 2-trifluoromethyl-10-{3-[4-(p-fluorobenzoyl)piperidinyl]propyl}phenothiazine.
Claim 11
Dependent Claim
1 words
2-Chloro-10-{3-[4-(p-fluorobenzoyl)piperidinyl]propyl}phenothiazine.
Claim 12
Dependent Claim
1 words
2-Chloro-10-{3-[4-(p-fluorobenzoyl)piperidinyl]propyl}phenothiazine.
Claim 13
Dependent Claim
16 words
The compound of claim 6 in the form of a non-toxic pharmaceutically acceptable acid addition salt.
Claim 14
Dependent Claim
2 words
2-Acetyl-10-[3-(p-fluorobenzoylpiperidinyl)propyl] phenothiazine.
Claim 15
Dependent Claim
2 words
2-Acetyl-10-[3-(p-fluorobenzoylpiperidinyl)propyl] phenothiazine.
Claim 16
Dependent Claim
16 words
The compound of claim 8 in the form of a non-toxic pharmaceutically acceptable acid addition salt.
Claim 17
Dependent Claim
73 words
A pharmaceutical composition useful for its tranquilizing properties comprising (a) an effective amount of a 10-[ω-(benzoylpiperidinyl)alkyl]phenothiazine having the formula: ##STR10## wherein; R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl or dimethylsulfamoyl, R 1 is selected from the group consisting of hydrogen, chloro, bromo, fluoro, trifluoromethyl, lower alkoxy or lower alkyl, n is a positive integer from 2-4 inclusive, and (b) a pharmaceutically acceptable carrier therefor.
Claim 18
Dependent Claim
73 words
A pharmaceutical composition useful for its tranquilizing properties comprising (a) an effective amount of a 10-[ω-(benzoylpiperidinyl)alkyl]phenothiazine having the formula: ##STR10## wherein; R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl or dimethylsulfamoyl, R 1 is selected from the group consisting of hydrogen, chloro, bromo, fluoro, trifluoromethyl, lower alkoxy or lower alkyl, n is a positive integer from 2-4 inclusive, and (b) a pharmaceutically acceptable carrier therefor.
Claim 19
Dependent Claim
24 words
A pharmaceutical composition as defined in claim 10, wherein the active ingredient is in the form of a non-toxic pharmaceutically acceptable acid addition salt.
Claim 20
Dependent Claim
23 words
A pharmaceutical composition as defined in claim 11, wherein the active ingredient is present in the amount of from 5 to 500 milligrams.
Claim 21
Dependent Claim
15 words
The pharmaceutical composition as defined in claim 12, wherein the active ingredient is 2-acetyl-10-{3-[4-(p-fluorobenzoyl) piperidinyl]propyl}phenothiazine.
Claim 22
Dependent Claim
14 words
The pharmaceutical composition as defined in claim 12, wherein the active ingredient is 2-trifluoromethyl-10-{3-[4-(p-fluorobenzoyl)piperidinyl]propyl}phenothiazine.
Claim 23
Dependent Claim
31 words
A pharmaceutical composition useful for its tranquilizing properties comprising (a) an effective amount of 2-chloro-10-{3-[4-(p-fluorobenzoyl)piperidinyl]propyl}phenothiazine or a non-toxic pharmaceutically acceptable acid addition salt thereof and (b) a pharmaceutically acceptable carrier therefor.
Claim 24
Dependent Claim
31 words
A pharmaceutical composition useful for its tranquilizing properties comprising (a) an effective amount of 2-chloro-10-{3-[4-(p-fluorobenzoyl)piperidinyl]propyl}phenothiazine or a non-toxic pharmaceutically acceptable acid addition salt thereof and (b) a pharmaceutically acceptable carrier therefor.
Claim 25
Independent Claim
71 words
A method for inducing tranquilization in a mammal comprising administering to a mammal a tranquilizing effective amount of a compound having the formula: ##STR11## wherein; R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl or dimethylsulfamoyl, R 1 is selected from the group consisting of hydrogen, chloro, bromo, fluoro, trifluoromethyl, lower alkoxy or lower alkyl, and n is a positive integer from 2-4 inclusive.
Claim 26
Independent Claim
71 words
A method for inducing tranquilization in a mammal comprising administering to a mammal a tranquilizing effective amount of a compound having the formula: ##STR11## wherein; R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl or dimethylsulfamoyl, R 1 is selected from the group consisting of hydrogen, chloro, bromo, fluoro, trifluoromethyl, lower alkoxy or lower alkyl, and n is a positive integer from 2-4 inclusive.
Claim 27
Dependent Claim
21 words
The method according to claim 16 wherein the active ingredient is in the form of a pharmaceutically acceptable acid addition salt.
Claim 28
Dependent Claim
29 words
The method according to claim 17 wherein the active ingredient is administered together with a pharmaceutically acceptable carrier therefor and in an amount of about one to 500 milligrams.
Claim 29
Dependent Claim
12 words
The method according to claim 18 wherein the active ingredient is 2-acetyl-10-{3-[4-(p-fluorobenzoyl)piperidinyl]propyl}phenothiazine.
Claim 30
Dependent Claim
13 words
The method according to claim 18 wherein the active ingredient is 2-trifluoromethyl-10-{3-[4-(p-fluorobenzoyl) piperidinyl]propyl}phenothiazine.
Claim 31
Independent Claim
28 words
A method for inducing tranquilization in a mammal comprising administering to a mammal a tranquilizing effective amount of 2-chloro-10-[3-(4-p-fluorobenzoylpiperidinyl)propyl]phenothiazine or a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 32
Independent Claim
28 words
A method for inducing tranquilization in a mammal comprising administering to a mammal a tranquilizing effective amount of 2-chloro-10-[3-(4-p-fluorobenzoylpiperidinyl)propyl]phenothiazine or a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 33
Dependent Claim
120 words
A process for the preparation of 10-[ω-(benzoylpiperidinyl) alkyl]phenothiazines having the formula: ##STR12## wherein; R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl or dimethylsulfamoyl, R 1 is selected from the group consisting of hydrogen, chloro, bromo, fluoro, trifluoromethyl, lower alkoxy or lower alkyl, and n is a positive integer from 2-4 inclusive, which comprises mixing and heating in an aprotic solvent at a temperature from about 80°-130° C. in the presence of a strong inorganic base a 1-(ω-haloalkyl)-4-(2 or 3)-benzoylpiperidine of the formula: ##STR13## wherein n and R 1 are as defined hereinabove and X is chloro, bromo or iodo with a phenothiazine of the formula: ##STR14## wherein R is as defined hereinabove.
Claim 34
Dependent Claim
120 words
A process for the preparation of 10-[ω-(benzoylpiperidinyl) alkyl]phenothiazines having the formula: ##STR12## wherein; R is selected from the group consisting of hydrogen, bromo, chloro, trifluoromethyl, lower alkoxy, acetyl, sulfamoyl or dimethylsulfamoyl, R 1 is selected from the group consisting of hydrogen, chloro, bromo, fluoro, trifluoromethyl, lower alkoxy or lower alkyl, and n is a positive integer from 2-4 inclusive, which comprises mixing and heating in an aprotic solvent at a temperature from about 80°-130° C. in the presence of a strong inorganic base a 1-(ω-haloalkyl)-4-(2 or 3)-benzoylpiperidine of the formula: ##STR13## wherein n and R 1 are as defined hereinabove and X is chloro, bromo or iodo with a phenothiazine of the formula: ##STR14## wherein R is as defined hereinabove.
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) | 1980-05-02 | 1980-11-01 | 1981-05-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-02 | 1984-11-01 | 1985-05-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-02 | 1988-11-01 | 1989-05-03 | $7700.00 | Window Closed / Lapsed |