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US4342870A
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Novel 3-(1-piperidinylalkyl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives
Assignee: Janssen Pharmaceutica NV
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Filing: 1980-09-29
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Granted: 1982-08-03
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Expires: 2000-09-29
Abstract
Abstract Novel 3-(1-piperidinylalkyl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives, wherein the piperidine ring is substituted with an aroyl radical or a functional derivative thereof, said compounds being potent serotonin-antagonists.
Inventors
- 👤 Ludo E. J. Kennis
- 👤 Josephus C. Mertens
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 14:18
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A61; A61P; A61P11/00; A61P11/08; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/30; C07D211/34; C07D211/68; C07D211/70
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
213 words
A chemical compound selected from the group consisting of a 3-[(1-piperidinyl)alkyl]-4H-pyrido[1,2-a]pyrimidin-4-one derivative having the formula ##STR29## and the pharmaceutically acceptable acid addition salts thereof, wherein R 1 and R 2 are each independently selected from the groups consisting of hydrogen, lower alkyl, lower alkyloxy, halo and trifluoromethyl; R 3 is a member selected from the group consisting of hydrogen, lower alkyl and aryl; Alk is a lower alkylene radical; R is a member selected from the group consisting of hydrogen, lower alkyl, hydroxy, lower alkyloxy and hydroxymethyl in the 2-, 3- or 4-position of the piperidine ring; X is a member selected from the group consisting of >C═O, >CHOH, ##STR30## >CH 2 , >C(O-lower alkyl) 2 , ##STR31## >C═NOH and >C═N-NH 2 , wherein said R a is hydrogen or lower alkyl and said q is the integer 2 or 3; and Ar is aryl; wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, thienyl, furanyl and pyridinyl, wherein said substituted phenyl has from 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro, amino and hydroxy, provided that no more than one substituent is nitro and further provided that said substituents are not simultaneously hydroxy and loweralkyloxy.
Claim 2
Dependent Claim
213 words
A chemical compound selected from the group consisting of a 3-[(1-piperidinyl)alkyl]-4H-pyrido[1,2-a]pyrimidin-4-one derivative having the formula ##STR29## and the pharmaceutically acceptable acid addition salts thereof, wherein R 1 and R 2 are each independently selected from the groups consisting of hydrogen, lower alkyl, lower alkyloxy, halo and trifluoromethyl; R 3 is a member selected from the group consisting of hydrogen, lower alkyl and aryl; Alk is a lower alkylene radical; R is a member selected from the group consisting of hydrogen, lower alkyl, hydroxy, lower alkyloxy and hydroxymethyl in the 2-, 3- or 4-position of the piperidine ring; X is a member selected from the group consisting of >C═O, >CHOH, ##STR30## >CH 2 , >C(O-lower alkyl) 2 , ##STR31## >C═NOH and >C═N-NH 2 , wherein said R a is hydrogen or lower alkyl and said q is the integer 2 or 3; and Ar is aryl; wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, thienyl, furanyl and pyridinyl, wherein said substituted phenyl has from 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro, amino and hydroxy, provided that no more than one substituent is nitro and further provided that said substituents are not simultaneously hydroxy and loweralkyloxy.
Claim 3
Dependent Claim
11 words
A chemical compound according to claim 1 wherein R is hydrogen.
Claim 4
Dependent Claim
20 words
A chemical compound according to claim 1 wherein R is hydrogen and X is >C═O, >C(O-lower alkyl) 2 or ##STR32##
Claim 5
Dependent Claim
20 words
A chemical compound according to claim 1 wherein R is hydrogen, X is >C═O and Alk is an 1,2-ethanediyl radical.
Claim 6
Dependent Claim
18 words
A chemical compound selected from the group consisting of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one and the pharmaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim
18 words
A chemical compound selected from the group consisting of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one and the pharmaceutically acceptable acid addition salts thereof.
Claim 8
Dependent Claim
190 words
A chemical compound selected from the group consisting of a 4H-pyrido[1,2-a]pyrimidin-4-one derivative having the formula ##STR33## and the pharmaceutically acceptable acid addition salts thereof, wherein: R 1 and R 2 are each independently selected from the group consisting of hydrogen, lower alkyl, lower alkyloxy, halo and trifluoromethyl; R 3 is a member selected from the group consisting of hydrogen, lower alkyl and aryl; Alk is a lower alkylene radical; R is a member selected from the group consisting of hydrogen, lower alkyl, hydroxy, lower alkyloxy, hydroxymethyl in the 2-, 3- or 4-position of the piperidine ring; and R 4 and R 5 are each independently selected from the group consisting of hydrogen, halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro, amino and hydroxy; wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, thienyl, furanyl and pyridinyl, wherein said substituted phenyl has from 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro, amino and hydroxy, provided that no more than one substituent is nitro and further provided that said substituents are not simultaneously hydroxy and loweralkyloxy.
Claim 9
Dependent Claim
190 words
A chemical compound selected from the group consisting of a 4H-pyrido[1,2-a]pyrimidin-4-one derivative having the formula ##STR33## and the pharmaceutically acceptable acid addition salts thereof, wherein: R 1 and R 2 are each independently selected from the group consisting of hydrogen, lower alkyl, lower alkyloxy, halo and trifluoromethyl; R 3 is a member selected from the group consisting of hydrogen, lower alkyl and aryl; Alk is a lower alkylene radical; R is a member selected from the group consisting of hydrogen, lower alkyl, hydroxy, lower alkyloxy, hydroxymethyl in the 2-, 3- or 4-position of the piperidine ring; and R 4 and R 5 are each independently selected from the group consisting of hydrogen, halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro, amino and hydroxy; wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, thienyl, furanyl and pyridinyl, wherein said substituted phenyl has from 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro, amino and hydroxy, provided that no more than one substituent is nitro and further provided that said substituents are not simultaneously hydroxy and loweralkyloxy.
References Cited (Backward Citations)
US3412094A
Cited
JPS525795A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-08-02 | 1986-02-01 | 1986-08-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-02 | 1990-02-01 | 1990-08-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-02 | 1994-02-01 | 1994-08-03 | $7700.00 | Window Closed / Lapsed |