US4166852A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Piperazino-pyrimidines and their use as spasmolytic agents
Assignee: Produits Chimiques Ugine Kuhlmann
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Filing: 1977-02-28
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Granted: 1979-09-04
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Expires: 1997-02-28
Abstract
Abstract The compounds of the formula: <IMAGE> (I) in which R represents a methyl or methylthio group, X represents a halogen atom or an alkoxy group containing 1 to 5 carbon atoms, Y represents an acylamino group or a substituted or unsubstituted amino group, Z represents a hydrogen atom or a methyl, ethyl, hdroxyethyl or phenyl group, with the exception of 2-methylamino-4-N-methylpiperazino-5-methylthio-6-chloro-pyrimidine; process for their preparation: medicaments comprising such compounds or salts thereof and with pharmaceutically acceptable acids and the use of such compounds or salts in the treatment of human beings.
Inventors
- 👤 Gerard P. M. H. Loiseau
- 👤 Georges D. Mattioda
- 👤 Rene J. Millischer
- 👤 Pierre M. J. Obellianne
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 22:29
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/48
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
4 words
The compound: 2-isopropyl-amino-4-N-methyl piperazino-6-chloro-5-methylthio-pyrimidine.
Claim 2
Dependent Claim
4 words
The compound: 2-isopropyl-amino-4-N-methyl piperazino-6-chloro-5-methylthio-pyrimidine.
Claim 3
Dependent Claim
3 words
The compound: 2-ethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 4
Dependent Claim
3 words
The compound: 2-ethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 5
Dependent Claim
3 words
The compound: 2-t-butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 6
Dependent Claim
3 words
The compound: 2-t-butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 7
Dependent Claim
3 words
The compound: 2-(N-methyl-N-phenyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 8
Dependent Claim
3 words
The compound: 2-(N-methyl-N-phenyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 9
Dependent Claim
3 words
The compound: 2-N-diethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 10
Dependent Claim
3 words
The compound: 2-N-diethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 11
Dependent Claim
3 words
The compound: 2-allylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 12
Dependent Claim
3 words
The compound: 2-allylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 13
Dependent Claim
3 words
The compound: 2-cyclohexylamino-4-N-methyl-piperazino-6-chloro-5-methylthio-pyrimidine.
Claim 14
Dependent Claim
3 words
The compound: 2-cyclohexylamino-4-N-methyl-piperazino-6-chloro-5-methylthio-pyrimidine.
Claim 15
Dependent Claim
3 words
The compound: 2-n.pentylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 16
Dependent Claim
3 words
The compound: 2-n.pentylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 17
Dependent Claim
3 words
The compound: 2-n.hexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 18
Dependent Claim
3 words
The compound: 2-n.hexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 19
Dependent Claim
3 words
The compound: 2-benzylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 20
Dependent Claim
3 words
The compound: 2-benzylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 21
Dependent Claim
3 words
The compound: 2-n.propylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 22
Dependent Claim
3 words
The compound: 2-n.propylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 23
Dependent Claim
3 words
The compound: 2-n.butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 24
Dependent Claim
3 words
The compound: 2-n.butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 25
Dependent Claim
3 words
The compound: 2-methylamino-4-N-(β-hydroxyethyl)piperazino-6-chloro-5-methylthio-pyrmidine.
Claim 26
Dependent Claim
3 words
The compound: 2-methylamino-4-N-(β-hydroxyethyl)piperazino-6-chloro-5-methylthio-pyrmidine.
Claim 27
Dependent Claim
3 words
The compound: 2-(N-methyl-N-benzoyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 28
Dependent Claim
3 words
The compound: 2-(N-methyl-N-benzoyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine.
Claim 29
Dependent Claim
51 words
A pharmaceutical composition in unit dosage form comprising 10 mg to 500 mg of a compound selected from the group consisting of: 2-isopropylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-ethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-t-butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-(N-methyl-N-phenyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-N-diethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-allylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-cyclohexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.pentylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.hexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-benzylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrmidine; 2-n.propylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-methylamino-4-N-(β-hydroxyethyl)piperazino-6-chloro-5-methylthio-pyrimidine; and 2-(N-methyl-N-benzoyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine, or a salt thereof with a pharmaceutically acceptable acid, and a pharmaceutically acceptable carrier.
Claim 30
Dependent Claim
51 words
A pharmaceutical composition in unit dosage form comprising 10 mg to 500 mg of a compound selected from the group consisting of: 2-isopropylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-ethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-t-butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-(N-methyl-N-phenyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-N-diethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-allylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-cyclohexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.pentylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.hexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-benzylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrmidine; 2-n.propylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-methylamino-4-N-(β-hydroxyethyl)piperazino-6-chloro-5-methylthio-pyrimidine; and 2-(N-methyl-N-benzoyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine, or a salt thereof with a pharmaceutically acceptable acid, and a pharmaceutically acceptable carrier.
Claim 31
Dependent Claim
64 words
Process for the treatment of spasms in a human being which comprises administering to a human in need thereof, as a spasmolytic agent, an effective amount of a compound selected from the group consisting of: 2-isopropylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-ethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-t-butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-(N-methyl-N-phenyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-N-diethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-allylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-cyclohexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.pentylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.hexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-benzylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.propylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-methylamino-4-N-(β-hydroxyethyl)piperazino-6-chloro-5-methylthio-pyrimidine; and 2-(N-methyl-N-benzoyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine, or a salt thereof with a pharmaceutically acceptable acid, and a pharmaceutically acceptable carrier.
Claim 32
Dependent Claim
64 words
Process for the treatment of spasms in a human being which comprises administering to a human in need thereof, as a spasmolytic agent, an effective amount of a compound selected from the group consisting of: 2-isopropylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-ethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-t-butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-(N-methyl-N-phenyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-N-diethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-allylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-cyclohexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.pentylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.hexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-benzylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.propylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-methylamino-4-N-(β-hydroxyethyl)piperazino-6-chloro-5-methylthio-pyrimidine; and 2-(N-methyl-N-benzoyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine, or a salt thereof with a pharmaceutically acceptable acid, and a pharmaceutically acceptable carrier.
Claim 33
Dependent Claim
75 words
Process for the treatment of spasms in a human being which comprises orally or intravenously administering to a human in need thereof, as a spasmolytic agent of low toxicity, an effective amount of a compound selected from the group consisting of: 2-isopropylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-ethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-t-butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-(N-methyl-N-phenyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-N-diethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-allylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-cyclohexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.pentylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.hexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-benzylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrmidine; 2-benzylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.propylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; and 2-methylamino-4-N-(β-hydroxyethyl)piperazino-6-chloro-5-methylthio-pyrimidine, or a salt thereof with a pharmaceutically acceptable acid at a daily dose of 50 mg to 2500 mg.
Claim 34
Dependent Claim
75 words
Process for the treatment of spasms in a human being which comprises orally or intravenously administering to a human in need thereof, as a spasmolytic agent of low toxicity, an effective amount of a compound selected from the group consisting of: 2-isopropylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-ethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-t-butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-(N-methyl-N-phenyl)amino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-N-diethylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-allylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-cyclohexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.pentylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.hexylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-benzylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrmidine; 2-benzylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.propylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; 2-n.butylamino-4-N-methylpiperazino-6-chloro-5-methylthio-pyrimidine; and 2-methylamino-4-N-(β-hydroxyethyl)piperazino-6-chloro-5-methylthio-pyrimidine, or a salt thereof with a pharmaceutically acceptable acid at a daily dose of 50 mg to 2500 mg.
Claim 35
Dependent Claim
11 words
Process according to claim 17 wherein said compound is administered orally.
Claim 36
Dependent Claim
11 words
Process according to claim 17 wherein said compound is administered intravenously.
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) | 1982-09-03 | 1983-03-05 | 1983-09-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-09-03 | 1987-03-05 | 1987-09-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-09-03 | 1991-03-05 | 1991-09-04 | $7700.00 | Window Closed / Lapsed |