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Novel 3-(1-piperidinylalkyl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives

Assignee: Janssen Pharmaceutica NV
•
Filing: 1980-09-29
•
Granted: 1982-08-03
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Expires: 2000-09-29
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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

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