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US4335127A Expired / Lapsed US ⏱️ 0.0 years remaining

Piperidinylalkyl quinazoline compounds, composition and method of use

Assignee: Janssen Pharmaceutica NV
•
Filing: 1979-10-12
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Granted: 1982-06-15
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Expires: 1999-10-12
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Abstract

Abstract Novel quinazoline derivatives, comprising in the heterocyclic part of their quinazoline nucleus at least one carbonyl or thiocarbonyl group and a particularly substituted piperidinyl-alkyl side chain, said compounds being potent serotonin-antagonists.

Inventors

  • 👤 Jan Vandenberk
  • 👤 Ludo Kennis
  • 👤 Marcel Van der Aa
  • 👤 Albert Van Heertum

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 19:52
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/06; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/30; C07D211/32; A; A61; A61P; A61P25/00; A61P25/02; A61P9/00; A61P9/08; C07D239/00; C07D239/70; C07D239/72; C07D239/78; C07D239/80; C07D239/86; C07D239/88; C07D239/90; C07D239/95; C07D239/96

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 251 words
A chemical compound selected from the group consisting of a quinazoline compound having the formula ##STR38## and the pharmaceutically acceptable acid addition salts thereof, wherein; Ar is a number selected from the group consisting of aryl, thienyl, and pyridinyl radicals; X is a member selected from the group consisting of ##STR39## wherein said q is the integer 2 or 3; R is a member selected from the group consisting of hydrogen, hydroxy and lower alkyl; Alk is an alkylene chain having from 1 to 4 carbon atoms; and Q is a quinazolinyl radical, the 1-, 2-, 3- or 4-position of which is connected with the alkylene side chain, said quinazolinyl radical bearing in one or both of its 2- and 4-positions a oxo or thioxo group, wherein the benzene ring of said quinazolinyl radical is optionally substituted with 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro and cyano, and wherein the pyrimidino ring of said quinazolinyl radical may be partly or fully saturated, said pyrimidino ring being optionally substituted with 1 to 3 substituents independently selected from the group consisting of lower alkyl, aryl, aryl(lower alkyl), thienyl, pyridinyl, thienyl(loweralkyl), and pyridinyl (loweralkyl); wherein said aryl as used in the definition of said Ar and of said Q is a member selected from the group consisting of phenyl substituted with from 1 to 2 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl and amino.
Claim 2
Dependent Claim 251 words
A chemical compound selected from the group consisting of a quinazoline compound having the formula ##STR38## and the pharmaceutically acceptable acid addition salts thereof, wherein; Ar is a number selected from the group consisting of aryl, thienyl, and pyridinyl radicals; X is a member selected from the group consisting of ##STR39## wherein said q is the integer 2 or 3; R is a member selected from the group consisting of hydrogen, hydroxy and lower alkyl; Alk is an alkylene chain having from 1 to 4 carbon atoms; and Q is a quinazolinyl radical, the 1-, 2-, 3- or 4-position of which is connected with the alkylene side chain, said quinazolinyl radical bearing in one or both of its 2- and 4-positions a oxo or thioxo group, wherein the benzene ring of said quinazolinyl radical is optionally substituted with 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro and cyano, and wherein the pyrimidino ring of said quinazolinyl radical may be partly or fully saturated, said pyrimidino ring being optionally substituted with 1 to 3 substituents independently selected from the group consisting of lower alkyl, aryl, aryl(lower alkyl), thienyl, pyridinyl, thienyl(loweralkyl), and pyridinyl (loweralkyl); wherein said aryl as used in the definition of said Ar and of said Q is a member selected from the group consisting of phenyl substituted with from 1 to 2 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl and amino.
Claim 3
Dependent Claim 11 words
A chemical compound according to claim 1 wherein X is CO.
Claim 4
Dependent Claim 13 words
A chemical compound according to claim 2 wherein Alk is an 1,2-ethanediyl radical.
Claim 5
Dependent Claim 18 words
A chemical compound selected from the group consisting of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedione and the pharmaceutically acceptable acid addition salts thereof.
Claim 6
Dependent Claim 18 words
A chemical compound selected from the group consisting of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedione and the pharmaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim 41 words
A chemical compound according to claim 1 wherein Ar is an aryl radical, X is >C═O, Alk is an alkylene chain having 2 or 3 carbon atoms; and Q is connected to the alkylene side chain by the 2- or 3-position.
Claim 8
Dependent Claim 269 words
An anti-congestive composition comprising an inert carrier and as an active ingredient an effective anticongestive amount of a chemical compound selected from the group consisting of a quinazoline compound having the formula ##STR40## and the pharmaceutically acceptable acid addition salts thereof, wherein: Ar is a member selected from the group consisting of aryl, thienyl, and pyridinyl radicals; X is a member selected from the group consisting of ##STR41## wherein said q is the integer 2 or 3; R is a member selected from the group consisting of hydrogen, hydroxy and lower alkyl; Alk is an alkylene chain having from 1 to 4 carbon atoms; and Q is a quinazolinyl radical, the 1-, 2-, 3- or 4-position of which is connected with the alkylene side chain, said quinazolinyl radical bearing in one or both of its 2- and 4-positions a oxo or thioxo group, wherein the benzene ring of said quinazolinyl radical is optionally substituted with 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro and cyano, and wherein the pyrimidino ring of said quinazolinyl radical may be partly or fully saturated, said pyrimidino ring being optionally substituted with 1 to 3 substituents independently selected from the group consisting of lower alkyl, aryl, aryl(lower alkyl), thienyl, pyridinyl, thienyl (loweralkyl), and pyridinyl (loweralkyl); wherein said aryl as used in the definition of said Ar and of said Q is a member selected from the group consisting of phenyl substituted with from 1 to 2 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl and amino.
Claim 9
Dependent Claim 269 words
An anti-congestive composition comprising an inert carrier and as an active ingredient an effective anticongestive amount of a chemical compound selected from the group consisting of a quinazoline compound having the formula ##STR40## and the pharmaceutically acceptable acid addition salts thereof, wherein: Ar is a member selected from the group consisting of aryl, thienyl, and pyridinyl radicals; X is a member selected from the group consisting of ##STR41## wherein said q is the integer 2 or 3; R is a member selected from the group consisting of hydrogen, hydroxy and lower alkyl; Alk is an alkylene chain having from 1 to 4 carbon atoms; and Q is a quinazolinyl radical, the 1-, 2-, 3- or 4-position of which is connected with the alkylene side chain, said quinazolinyl radical bearing in one or both of its 2- and 4-positions a oxo or thioxo group, wherein the benzene ring of said quinazolinyl radical is optionally substituted with 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro and cyano, and wherein the pyrimidino ring of said quinazolinyl radical may be partly or fully saturated, said pyrimidino ring being optionally substituted with 1 to 3 substituents independently selected from the group consisting of lower alkyl, aryl, aryl(lower alkyl), thienyl, pyridinyl, thienyl (loweralkyl), and pyridinyl (loweralkyl); wherein said aryl as used in the definition of said Ar and of said Q is a member selected from the group consisting of phenyl substituted with from 1 to 2 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl and amino.
Claim 10
Dependent Claim 11 words
An anti-congestive composition according to claim 6 wherein X is CO.
Claim 11
Dependent Claim 13 words
An anti-congestive composition according to claim 7 wherein Alk is an 1,2-ethanediyl radical.
Claim 12
Dependent Claim 34 words
An anti-congestive composition comprising an inert carrier and as an active ingredient an effective anti-congestive amount of a chemical compound selected from the group consisting of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedione and the pharmaceutically acceptable acid-addition salts thereof.
Claim 13
Dependent Claim 34 words
An anti-congestive composition comprising an inert carrier and as an active ingredient an effective anti-congestive amount of a chemical compound selected from the group consisting of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedione and the pharmaceutically acceptable acid-addition salts thereof.
Claim 14
Dependent Claim 41 words
An anticongestive composition according to claim 6 wherein Ar is an arly radical, X is >C═O, Alk is an alkylene chain having 2 or 3 carbon atoms; and Q is connected to the alkylene side chain by the 2- or 3-position.
Claim 15
Independent Claim 272 words
A method of treating congestion in warm-blooded animals which comprises the administration thereto of an effective anticongestive amount of a chemical compound selected from the group consisting of a quinazoline compound having the formula ##STR42## and the pharmaceutically acceptable acid addition salts thereof, wherein: Ar is a member selected from the group consisting of aryl, thienyl, and pyridinyl radicals; X is a member selected from the group consisting of ##STR43## wherein said q is the integer 2 or 3; R is a member selected from the group consisting of hydrogen, hydroxy and lower alkyl; Alk is an alkylene chain having from 1 to 4 carbon atoms; and Q is a quinazolinyl radical, the 1-, 2-, 3- or 4-position of which is connected with the alkylene side chain, said quinazolinyl radical bearing in one or both of its 2- and 4-positions a oxo or thioxo group, wherein the benzene ring of said quinazolinyl radical is optionally substituted with 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro and cyano, and wherein the pyrimidino ring of said quinazolinyl radical may be partyly or fully saturated, said pyrimidino ring being optionally substituted with 1 to 3 substituents independently selected from the group consisting of lower alkyl, aryl, aryl(loweralkyl), thienyl, pyridinyl, thienyl (loweralkyl), and pyridinyl (lower alkyl); wherein aryl as used in the definition of said Ar and of said Q is a member selected from the group consisting of penyl and phenyl substituted with from 1 to 2 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl and amino.
Claim 16
Independent Claim 272 words
A method of treating congestion in warm-blooded animals which comprises the administration thereto of an effective anticongestive amount of a chemical compound selected from the group consisting of a quinazoline compound having the formula ##STR42## and the pharmaceutically acceptable acid addition salts thereof, wherein: Ar is a member selected from the group consisting of aryl, thienyl, and pyridinyl radicals; X is a member selected from the group consisting of ##STR43## wherein said q is the integer 2 or 3; R is a member selected from the group consisting of hydrogen, hydroxy and lower alkyl; Alk is an alkylene chain having from 1 to 4 carbon atoms; and Q is a quinazolinyl radical, the 1-, 2-, 3- or 4-position of which is connected with the alkylene side chain, said quinazolinyl radical bearing in one or both of its 2- and 4-positions a oxo or thioxo group, wherein the benzene ring of said quinazolinyl radical is optionally substituted with 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro and cyano, and wherein the pyrimidino ring of said quinazolinyl radical may be partyly or fully saturated, said pyrimidino ring being optionally substituted with 1 to 3 substituents independently selected from the group consisting of lower alkyl, aryl, aryl(loweralkyl), thienyl, pyridinyl, thienyl (loweralkyl), and pyridinyl (lower alkyl); wherein aryl as used in the definition of said Ar and of said Q is a member selected from the group consisting of penyl and phenyl substituted with from 1 to 2 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl and amino.
Claim 17
Dependent Claim 10 words
A method according to claim 11 wherein X is CO.
Claim 18
Dependent Claim 12 words
A method according to claim 12 wherein Alk is an 1,2-ethanediyl radical.
Claim 19
Independent Claim 38 words
A method of treating congestion in warm-blooded animals which comprises the administration thereto of an effective anti-congestive amount of a chemical compound selected from the group consisting of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H, 3H)-quinazolinedione and the pharmaceutically acceptable acid addition salts thereof.
Claim 20
Independent Claim 38 words
A method of treating congestion in warm-blooded animals which comprises the administration thereto of an effective anti-congestive amount of a chemical compound selected from the group consisting of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H, 3H)-quinazolinedione and the pharmaceutically acceptable acid addition salts thereof.
Claim 21
Dependent Claim 40 words
A method according to claim 11 wherein Ar is an aryl radical, X is >C═O, Alk is an alkylene chain having 2 or 3 carbon atoms; and Q is connected to the alkylene said chain by the 2- or 3-position.

References Cited (Backward Citations)

US3322766A Cited
US3635976A Cited
US4096144A Cited
US4099002A Cited
US4146717A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-06-14 1985-12-14 1986-06-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-06-14 1989-12-14 1990-06-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-06-14 1993-12-14 1994-06-15 $7700.00 Window Closed / Lapsed

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