US3957786A
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Aryl-substituted piperazinyl-alkylamino-uracils, -uracil ethers and -uracil thioethers and method for their production
Assignee: Takeda GmbH
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Filing: 1970-08-20
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Granted: 1976-05-18
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Expires: 1990-08-20
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 in mammalians.
Inventors
- 👤 Kurt Klemm
- 👤 Wolfgang Schoetensack
- 👤 Wolfgang Prusse
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 01:38
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: 32
Claim 1
Independent Claim
147 words
A compound of Formula I ##SPC15## wherein R 1 and R 2 each is hydrogen, alkyl of 1 to 4 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, and phenyl; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms, chlorine or bromine, 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.
Claim 2
Dependent Claim
147 words
A compound of Formula I ##SPC15## wherein R 1 and R 2 each is hydrogen, alkyl of 1 to 4 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, and phenyl; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms, chlorine or bromine, 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.
Claim 3
Dependent Claim
26 words
The compound of claim 1, wherein R 3 is hydrogen, alkyl of 1 to 4 carbon atoms, bromine, amino and diethylamino, and wherein Z is methoxy.
Claim 4
Dependent Claim
47 words
The salt of the compound of claim 1 with an acid of the group consisting of acetic acid, oxalic acid, maleic acid, fumaric acid, tartaric acid, benzoic acid, pamoic acid, salicylic acid, polygalacturonic acid, polyvinylcarboxylic acid, hydrochloric acid, sulfuric acid, phosphoric acid, amidosulfonic acid and methanesulfonic acid.
Claim 5
Dependent Claim
17 words
The compound of claim 1, wherein at least one of R 1 and R 2 is methyl.
Claim 6
Dependent Claim
20 words
The compound of claim 1, wherein R 3 is hydrogen, alkyl of 1 to 4 carbon atoms, amino or diethylamino.
Claim 7
Dependent Claim
12 words
The compound of claim 1, wherein Z is methoxy in the o-position.
Claim 8
Dependent Claim
13 words
The compound of claim 1, wherein R 3 is bromine, amino or diethylamino.
Claim 9
Dependent Claim
10 words
The compound of claim 1, wherein R 1 is methyl.
Claim 10
Dependent Claim
10 words
The compound of claim 1, wherein R 3 is hydrogen.
Claim 11
Dependent Claim
9 words
The compound of claim 1, wherein X is -NH-.
Claim 12
Dependent Claim
10 words
The compound of claim 1, wherein R 2 is methyl.
Claim 13
Dependent Claim
14 words
The compound of claim 1, wherein R 1 and R 2 both are methyl.
Claim 14
Dependent Claim
39 words
The compound of claim 1, wherein R 3 is --CH 3 , n--C 4 H 9 , --NO 2 , --Br, --Cl, --NO, --NH 2 , -NHCOC 2 H 5 , -CH=O, -NHCOOC 2 H 5 , or -SCN.
Claim 15
Dependent Claim
56 words
The compound of claim 1, wherein R 1 is methyl. R 2 is methyl, R 3 is hydrogen, X is --NH--, A is --CH 2 --CH 2 --CH 2 --, Y is hydrogen and Z is p--CH 3 , o--Cl, 2,5-dimethoxy, o--CH 3 , o--CH 2 H 5 , 2,4-dimethoxy, o-methoxy, m-methoxy, p-methoxy, hydrogen, or p--Cl.
Claim 16
Dependent Claim
44 words
The compound of claim 1, wherein R 1 is --CH 3 , R 2 is --CH 3 , R 3 is hydrogen, X is --O--, A is --CH(CH 3 )--CH 2 --, Y is hydrogen and Z is hydrogen, p--Cl or p--CH 3 .
Claim 17
Dependent Claim
49 words
The compound of claim 1, wherein R 1 is --CH 3 , R 2 is --CH 3 , R 3 is hydrogen, X is --S--, A is --CH(CH 3 )--CH 2 --, Y is hydrogen and Z is o--OCH 3 , hydrogen, m--CH 3 , p--CH 3 or p--Cl.
Claim 18
Dependent Claim
53 words
The compound of claim 1, wherein R 1 is --CH 3 , R 2 is --CH 3 , R 3 is hydrogen, X is --NH--, Y is hydrogen, Z is o--OCH 3 and A is --CH 2 --CH(CH 3 )--, --CH(CH 3 )--CH 2 -- or --CH 2 --CH 2 --CH 2 .
Claim 19
Dependent Claim
47 words
The compound of claim 1, wherein R 1 is --CH 3 , R 2 is hydrogen, R 3 is hydrogen, A is --CH 2 --CH 2 --CH 2 --, Y is hydrogen, Z is o--OCH 3 and X is --NH--, --N(C 2 H 5 )-- or --O--.
Claim 20
Dependent Claim
42 words
The compound of claim 1, wherein R 2 is hydrogen, R 3 is hydrogen, X is --NH--, A is --CH 2 --CH 2 --CH 2 --, Y is hydrogen, Z is o--OCH 3 and R 1 is hydrogen, butyl, cyclohexyl and phenyl.
Claim 21
Dependent Claim
22 words
The compound of claim 1 of the group consisting of 1,3-dimethyl-4-(γ-[4-(o-methoxyphenyl)-piperazinyl-(1)]-propylamino-uracil and a salt of this compound with a pharmaceutically acceptable acid.
Claim 22
Dependent Claim
8 words
The salt of claim 1, which is 1,3-dimethyl-4-(γ[4-(o-methoxyphenyl)-piperazinyl-(1)]-propylamino-5-bromo-uracil-dihydrobromide.
Claim 23
Dependent Claim
12 words
The compound of claim 1 wherein R 3 is NO 2 .
Claim 24
Dependent Claim
10 words
The compound of claim 1 wherein R 3 is Br.
Claim 25
Dependent Claim
12 words
The compound of claim 1 wherein R 3 is NH 2 .
Claim 26
Dependent Claim
10 words
The compound of claim 1 wherein R 3 is SCN.
Claim 27
Dependent Claim
1 words
1,3-Dimethyl-4-(gamma-[4-(o-methoxyphenyl)piperazinyl-(1)]-propylamino)-5-propionylamino-uracil.
Claim 28
Dependent Claim
1 words
1,3-Dimethyl-4-(gamma-[4-(o-methoxyphenyl)piperazinyl-(1)]-propylamino)-5-propionylamino-uracil.
Claim 29
Dependent Claim
2 words
1,3-Dimethyl-4-(1-methyl-2[4(orthomethoxyphenyl-piperazinyl(1)]-ethyloxy uracil-dihydrochloride.
Claim 30
Dependent Claim
2 words
1,3-Dimethyl-4-(1-methyl-2[4(orthomethoxyphenyl-piperazinyl(1)]-ethyloxy uracil-dihydrochloride.
Claim 31
Dependent Claim
14 words
The compound of claim 1 wherein the alkanoylamino of R 3 is propionyl amino.
Claim 32
Dependent Claim
53 words
The compound of claim 1 wherein R 3 is hydrogen, CH 3 , n-C 4 H 9 , NO 2 , Br, NO, NH 2 , NH(CO 2 C 2 H 5 ), NHCO-C 2 H 5 , CHO, SCN, N(C 2 H 5 ), CONHC 6 H 5 or COCH 3 .
References Cited (Backward Citations)
US2567651A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-05-18 | 1979-11-17 | 1980-05-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-05-18 | 1983-11-17 | 1984-05-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-05-18 | 1987-11-17 | 1988-05-18 | $7700.00 | Window Closed / Lapsed |