US4067982A
Expired / Lapsed
US
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Aryl-substituted piperazinyl-alkylamino-uracils, -uracil ethers and -uracil thioethers as therapeutics
Assignee: Takeda GmbH
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Filing: 1976-04-08
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Granted: 1978-01-10
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Expires: 1996-04-08
Abstract
Abstract Aryl-substituted piperazinyl-alkylamino-uracils, the corresponding uracil ethers and uracil-thioethers and their pharmaceutically acceptable salts such as the hydrochloride, and method for the preparation of these compounds. The novel compounds are useful for lowering the blood pressure, causing an analgesic, a sedative or antihistiminic effect in mammalians.
Inventors
- 👤 Kurt Klemm
- 👤 Wolfgang Schoetensack
- 👤 Wolfgang Prusse
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 23:42
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/52; C07D239/54; C07D239/545; C07D239/553; C07D239/557; C07D239/60; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
213 words
The method of causing a lowering of the blood pressure, causing an analgesic effect, antihistiminic effect or a sedative effect in a warm-blooded animal which comprises administering in a therapeutically effective dose, a pharmaceutical composition comprising a compound of the formula: ##STR26##wherein R 1 and R 2 each is hydrogen, alkyl or alkenyl of 1 to 6 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, or phenyl; R 3 is hydrogen, alkyl or alkenyl of 1 to 6 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, chlorine or bromine, phenyl, aralkyl, wherein the alkyl is of 1 to 3 carbon atoms, nitro, nitroso, amino, alkylamino of 1 to 3 carbon atoms, dialkylamino wherein each of the alkyl groups contain 1 to 3 carbon atoms, alkanoylamino of 1 to 4 carbon atoms, formyl, ethoxycarbonylamino, thiocyanato, COCH 3 or CONHC 6 H 5 ; X is --NH--, --NC 2 H 5 --, --O-- or --S--; A is --CH 2 --CH 2 CH 2 --, --CH(CH 3 )--CH 2 -- or --CH 2 -- CH(CH 3 ); Z is hydrogen, a methyl group, one or two methoxy groups or an ethoxy group, a chlorine atom and Y is hydrogen, and the pharmaceutically acceptable salts of these compounds, in mixture with a pharmaceutically acceptable carrier.
Claim 2
Independent Claim
213 words
The method of causing a lowering of the blood pressure, causing an analgesic effect, antihistiminic effect or a sedative effect in a warm-blooded animal which comprises administering in a therapeutically effective dose, a pharmaceutical composition comprising a compound of the formula: ##STR26##wherein R 1 and R 2 each is hydrogen, alkyl or alkenyl of 1 to 6 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, or phenyl; R 3 is hydrogen, alkyl or alkenyl of 1 to 6 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, chlorine or bromine, phenyl, aralkyl, wherein the alkyl is of 1 to 3 carbon atoms, nitro, nitroso, amino, alkylamino of 1 to 3 carbon atoms, dialkylamino wherein each of the alkyl groups contain 1 to 3 carbon atoms, alkanoylamino of 1 to 4 carbon atoms, formyl, ethoxycarbonylamino, thiocyanato, COCH 3 or CONHC 6 H 5 ; X is --NH--, --NC 2 H 5 --, --O-- or --S--; A is --CH 2 --CH 2 CH 2 --, --CH(CH 3 )--CH 2 -- or --CH 2 -- CH(CH 3 ); Z is hydrogen, a methyl group, one or two methoxy groups or an ethoxy group, a chlorine atom and Y is hydrogen, and the pharmaceutically acceptable salts of these compounds, in mixture with a pharmaceutically acceptable carrier.
Claim 3
Dependent Claim
11 words
The method of claim 1 wherein the administration is to humans.
Claim 4
Dependent Claim
13 words
The method of claim 2 of causing a lowering of the blood pressure.
Claim 5
Dependent Claim
10 words
The method of claim 2 of causing an analgesic effect.
Claim 6
Dependent Claim
10 words
The method of claim 2 of causing an antiinflammatory effect.
Claim 7
Dependent Claim
8 words
The method of claim 2 of causing sedation.
Claim 8
Dependent Claim
16 words
The method of claim 3 wherein the substituent Z is in the ortho-position or is hydrogen.
Claim 9
Dependent Claim
13 words
The method of claim 7 wherein the substituent Z is in the para-position.
Claim 10
Dependent Claim
16 words
The method of claim 6 wherein the substituent Z is in the ortho-position or is hydrogen.
Claim 11
Dependent Claim
16 words
The method of claim 4 wherein the substituent Z is in the ortho-position or is hydrogen.
Claim 12
Dependent Claim
10 words
The method of claim 3 wherein the compound is 1,3-dimethyl-4-(gamma-[-0-methoxyphenyl)-piperazinyl-(1)]-propylamino)-uracil.
Claim 13
Dependent Claim
209 words
A pharmaceutical composition for use in mammals to cause: a lowering of blood pressure, an analgesic, a sedative, or an histiminic effect, comprising, in a therapeutically effective amount to cause such effect, a compound of the general formula ##STR27##wherein R 1 and R 2 each is hydrogen, alkyl or alkenyl of 1 to 6 atoms, cycloalkyl of 5 to 6 carbon atoms, or phenyl; R 3 is hydrogen, alkyl or alkenyl of 1 to 6 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, chlorine or bromine, phenyl, benzylalkyl wherein the alkyl is of 1 to 3 carbon atoms, nitro, nitroso, amino, alkylamino of 1 to 3 carbon atoms, dialkylamino wherein each of the alkyl groups contain 1 to 3 carbon atoms, alkanoylamino of 1 to 4 carbon atoms, formyl, ethoxycarbonylamino, thiocyanato, COCH 3 or CONHC 6 H 5 ; X is --NH--, --NC 2 H 5 --, --O-- or --S--; A is --CH 2 --CH 2 --CH 2 --, --CH(CH 3 )--CH 2 -- or --CH 2 -- CH(CH 3 ); Z is hydrogen, a methyl group, one or two methoxy groups or an ethoxy group, a chlorine atom and Y is hydrogen, and the pharmacetucally acceptable salts of these compounds in mixture with a pharmaceutically acceptable carrier.
Claim 14
Dependent Claim
209 words
A pharmaceutical composition for use in mammals to cause: a lowering of blood pressure, an analgesic, a sedative, or an histiminic effect, comprising, in a therapeutically effective amount to cause such effect, a compound of the general formula ##STR27##wherein R 1 and R 2 each is hydrogen, alkyl or alkenyl of 1 to 6 atoms, cycloalkyl of 5 to 6 carbon atoms, or phenyl; R 3 is hydrogen, alkyl or alkenyl of 1 to 6 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, chlorine or bromine, phenyl, benzylalkyl wherein the alkyl is of 1 to 3 carbon atoms, nitro, nitroso, amino, alkylamino of 1 to 3 carbon atoms, dialkylamino wherein each of the alkyl groups contain 1 to 3 carbon atoms, alkanoylamino of 1 to 4 carbon atoms, formyl, ethoxycarbonylamino, thiocyanato, COCH 3 or CONHC 6 H 5 ; X is --NH--, --NC 2 H 5 --, --O-- or --S--; A is --CH 2 --CH 2 --CH 2 --, --CH(CH 3 )--CH 2 -- or --CH 2 -- CH(CH 3 ); Z is hydrogen, a methyl group, one or two methoxy groups or an ethoxy group, a chlorine atom and Y is hydrogen, and the pharmacetucally acceptable salts of these compounds in mixture with a pharmaceutically acceptable carrier.
Claim 15
Dependent Claim
18 words
The pharmaceutical composition of claim 12 in a therapeutically effective dosage of from about 1 to 100 mg.
Claim 16
Dependent Claim
21 words
The pharmaceutical composition of claim 13 wherein the dosage is of about 5 to 100 mg, especially suited for oral administration.
Claim 17
Dependent Claim
21 words
The pharmaceutical composition of claim 12 wherein the dosage is from about 1 to 50 mg, especially suited for intramuscular administration.
Claim 18
Dependent Claim
21 words
The pharmaceutical composition of claim 12 wherein the dosage is from about 1 to 30 mg especially suited for intravenous administration.
Claim 19
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1,3-dimethyl-4-(gamma-[4-(o-methoxyphenyl)-piperazinyl-(1)]-propylamino)[4-bromo]-uracil.
Claim 20
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1,3-dimethyl-4-(gamma-[4-o-methoxyphenyl)-piperazinyl-(1)]-propylamino)-5-propionylamino-uracil.
Claim 21
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1,3-dimethyl-4-(1-methyl-2[4(ortho-methoxyphenyl-piperazinyl-(1)]-ethyloxy)uracil.
Claim 22
Dependent Claim
23 words
The composition of claim 12 wherein the compound is in the form of its salt with a pharmaceutically acceptable organic or inorganic acid.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-01-09 | 1981-07-11 | 1982-01-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-09 | 1985-07-11 | 1986-01-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-09 | 1989-07-11 | 1990-01-10 | $7700.00 | Window Closed / Lapsed |