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US4457931A
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Piperazine derivatives with anticholinergic and/or antihistaminic activity
Assignee: Selvi and C SpA
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Filing: 1982-09-27
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Granted: 1984-07-03
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Expires: 2002-09-27
Abstract
Abstract Compounds of formula I ##STR1## are described in which R is an aryl, substituted aryl, aralkyl or heterocyclic radical; R 1 is hydrogen or alkyl of 1-4 carbon atoms; A is a saturated, aliphatic hydrocarbon chain, which is linear or branched; R 2 and R 3 are the same or different and are hydrogen, linear or branched alkyl, aryl, substituted aryl or together with the nitrogen atom to which they are connected and together with y form a ring wherein y is a methylene group or a heteroatom, which is selected from the group consisting of nitrogen, oxygen and sulfur; R 4 is hydrogen or linear or branched alkyl; X is halogen or an organic or inorganic anion; n is 0; 1; 2; 3 or in the case of a bifunctional acid, n is equal to 0.5; 1.5; 2.5 and their enantiomers and diestereoisomers. Several methods of preparation of the novel compounds are described.
Inventors
- 👤 Carlo Milani
- 👤 Giovanni M. Carminati
- 👤 Attilio Sovera
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 22:54
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/18; C07D295/182; C07D295/185; A; A61; A61P; A61P1/00; A61P11/00; A61P25/00; A61P25/02; A61P25/04; A61P25/20; A61P29/00; A61P43/00; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/74; C07D295/02; C07D295/04; C07D295/12; C07D295/125; C07D295/13; C07D295/20; C07D295/205; C07D405/00; C07D405/02; C07D405/12
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
152 words
A compound of formula I ##STR94## wherein: R is phenyl, unsubstituted or mono or di substituted by trifluoromethyl; benzyl, 2-pyridyl; R 1 is hydrogen; A is a saturated, linear or branched alkylene chain of up to 4 carbon atoms; R 2 and R 3 are the same or different and are hydrogen, linear or branched alkyl of 2-6 carbon atoms or the group ##STR95## methylene dioxy phenyl when y is zero; or are an alkylene chain which together with the nitrogen atom to which they are connected and together with y form a 5-, 6- or 7-member ring which is a cyclic group having one N atom, adamantyl or cyclohexyl; X is halogen or a pharmaceutically acceptable organic or inorganic anion; n is 0; 1; 2; 3 or in the case of a bifunctional acid, n is equal to 0.5; 1.5; 2.5 and lower alkyl quaternary compounds and enantiomers and diestereoisomers thereof.
Claim 2
Dependent Claim
152 words
A compound of formula I ##STR94## wherein: R is phenyl, unsubstituted or mono or di substituted by trifluoromethyl; benzyl, 2-pyridyl; R 1 is hydrogen; A is a saturated, linear or branched alkylene chain of up to 4 carbon atoms; R 2 and R 3 are the same or different and are hydrogen, linear or branched alkyl of 2-6 carbon atoms or the group ##STR95## methylene dioxy phenyl when y is zero; or are an alkylene chain which together with the nitrogen atom to which they are connected and together with y form a 5-, 6- or 7-member ring which is a cyclic group having one N atom, adamantyl or cyclohexyl; X is halogen or a pharmaceutically acceptable organic or inorganic anion; n is 0; 1; 2; 3 or in the case of a bifunctional acid, n is equal to 0.5; 1.5; 2.5 and lower alkyl quaternary compounds and enantiomers and diestereoisomers thereof.
Claim 3
Dependent Claim
28 words
A compound according to claim 1, wherein R is 2-pyridyl and the group ##STR96## is (a) cyclohexylamino; (b) dialkylamino; (c) adamentylamino; (d) piperidino; (e) hexamethylenimino; or (f) ##STR97##
Claim 4
Dependent Claim
31 words
A compound according to claim 2, wherein R is 2-pyridyl; R 2 is H; A is an alkylene chain of up to 4 carbon atoms; and ##STR98## forms the adamantylamino group.
Claim 5
Dependent Claim
33 words
A compound according to claim 2, wherein R is 2-pyridyl; R 2 is H; and the group ##STR99## forms the cyclohexylamino group; A is an alkylene chain of up to 4 carbon atoms.
Claim 6
Dependent Claim
28 words
A compound according to claim 2, wherein R is 2-pyridyl or benzyl; A is an alkylene chain of up to 4 carbon atoms and ##STR100## the hexamethylenimino ring.
Claim 7
Dependent Claim
26 words
A compound according to claim 2, wherein R is 2-pyridyl; A is an alkylene chain of up to 4 carbon atoms; ##STR101## forms the piperidino ring.
Claim 8
Dependent Claim
35 words
A compound according to claim 2, wherein R 1 is phenyl substituted by a trifluoromethyl group; A is an alkylene chain of up to 4 carbon atoms; and the group ##STR102## forms a dialkylamino group.
Claim 9
Dependent Claim
20 words
The compound according to claim 2, wherein said group ##STR103## forms the anilino group additionally substituted by a dioxy-methylene group.
Claim 10
Dependent Claim
9 words
A compound according to claim 1, which is 1-(2-pyridyl)-4-(2-(1-adamantylamino)-1-methylethyl)piperazine.
Claim 11
Dependent Claim
9 words
A compound according to claim 1, which is 1-(2-pyridyl)-4-(1-methyl-2-cyclohexylaminoethyl)piperazine.
Claim 12
Dependent Claim
10 words
A compound according to claim 1, which is 1-(2-pyridyl)-4-(1-methyl-2-hexamethyleniminoethyl)piperazine methiodide.
Claim 13
Dependent Claim
9 words
A compound according to claim 1, which is 1-(2-pyridyl)-4-(1-methyl-2-hexamethyleniminoethyl)piperazine.
Claim 14
Dependent Claim
9 words
A compound according to claim 1, which is 1-(2-pyridyl)-4-(1-methyl-2-piperidinoethyl)piperazine.
Claim 15
Dependent Claim
10 words
A compound according to claim 1, which is 1-(2-pyridyl)-4-(1-methyl-2-piperidinoethyl)piperazine methiodide.
Claim 16
Dependent Claim
10 words
A compound according to claim 1, which is 1-(2-pyridyl)-4-(1-methyl-2-piperidinoethyl)piperazine ethobromide.
Claim 17
Dependent Claim
10 words
A compound according to claim 1, which is 1-(2-pyridyl)-4-(1-ethyl-2-hexamethyleniminoethyl)piperazine methiodide.
Claim 18
Dependent Claim
10 words
A compound according to claim 1, which is 1-(2-pyridyl)-4-(1-methyl-2-n-hexylaminoethyl)piperazine maleate.
Claim 19
Dependent Claim
37 words
A pharmaceutical composition having anti-cholinergic activity, suitable for administration by the oral, rectal, parenteral route and by eye instillation, which contains as the active component a compound according to claim 1 or a pharmaceutically compatible salt thereof.
References Cited (Backward Citations)
JPS54103893A
Cited
JPS5761149A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-07-03 | 1988-01-02 | 1988-07-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-07-03 | 1992-01-02 | 1992-07-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-07-03 | 1996-01-02 | 1996-07-03 | $7700.00 | Window Closed / Lapsed |