Piperidinylalkyl quinazoline compounds, composition and method of use
AssigneeJanssen Pharmaceutica NV
InventorsJan Vandenberk, Ludo Kennis, Marcel Van der Aa, Albert Van Heertum
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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.
Claims15
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.
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.
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.
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.
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.
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.
Dependencies are inferred from the claim text.