Thieno[2,3-d]pyrimidine antiallergic agents
AssigneeMead Johnson & Company
InventorDavis L. Temple, Jr.
Life of this patent
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Abstract
2-Aminothiophene-3-carboxamides are converted to oxamates or fumaramides by acylation of the amino group. Cyclization yields thieno[2,3-d]pyrimidines which may also be prepared from the corresponding oxazines. Compounds illustrative of those having inhibitory action on the immediate hypersensitivity reaction in mammmals are N-[3(aminocarbonyl)-4,5,6,7-tetrahydrobenzo[b]thien-2-yl]oxamic acid, ethyl 5,6,7,8-tetrahydro-4oxo-4H-benzothieno[2,3-d][1,3]oxazine-2-carboxyl ate, and ethyl 3,4-dihydro-6-ethyl-4-oxothieno[2,3-d]pyrimidine-2-carboxylate.
Claims34
The compound having Formula I ##STR7## wherein:
- R.sup.2 is --CO.sub.2 R.sup.3, wherein R.sup.3 is selected from the group consisting of hydrogen, lower alkyl having 1 to 8 carbon atoms, and M wherein M is a non-toxic pharmacologically inert metal cation, and
- R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, lower alkyl having 1 to 8 carbon atoms, and amino.
The compound having Formula I ##STR8## wherein R.sup.2 is selected from the group consisting of CH.sub.2 OH, ##STR9## wherein R is lower alkyl having 1 to 8 carbon atoms,
- R.sup.3 is selected from the group consisting of hydrogen, lower alkyl having 1 to 8 carbon atoms, and M wherein M is a non-toxic pharmacologically inert metal cation, and
- R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, lower alkyl having 1 to 8 carbon atoms, lower alkenyl having 3 to 6 carbon atoms, lower alkoxy having 1 to 6 carbon atoms, hydroxy, nitro, amino, halo, phenyl, alkanoyl having 2 to 6 carbon atoms, or together they constitute a cycloalkene ring or an R-substituted cycloalkene ring wherein R is as defined above and said cycloalkene ring contains 5 to 7 annular atoms.
A method of inhibiting the immediate hypersensitivity reaction in a sensitive mammal which comprises administering to said mammal an effective hypersensitivity reaction inhibiting dose of a compound having Formula I ##STR10## wherein R.sup.2 is selected from the group consisting of --CO.sub.2 R.sup.3, --CH.dbd.CHCO.sub.2 R.sup.3, --CH.sub.2 OH, ##STR11## and --CHO wherein R is lower alkyl having 1 to 8 carbon atoms,
- R.sup.3 is selected from the group consisting of hydrogen, lower alkyl having 1 to 8 carbon atoms, and M wherein M is a non-toxic pharmacologically inert metal cation, and
- R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, lower alkyl having 1 to 8 carbon atoms, lower alkenyl having 3 to 6 carbon atoms, lower alkoxy having 1 to 6 carbon atoms, hydroxy, nitro, amino, halo, phenyl, alkanoyl having 2 to 6 carbon atoms, or together they constitute a cycloalkene ring or an R-substituted cycloalkene ring wherein R is as defined above and said cycloalkene ring contains 5 to 7 annular atoms.
A pharmaceutical composition in dosage unit form comprising a pharmaceutical carrier and an effective mammalian immediate hypersensitivity reaction inhibiting dose of a compound having Formula I ##STR12## wherein R.sup.2 is selected from the group consisting of --CO.sub.2 R.sup.3, --CH.dbd.CHCO.sub.2 R.sup.3, --CH.sub.2 OH, ##STR13## and --CHO wherein R is lower alkyl having 1 to 8 carbon atoms,
- R.sup.3 is selected from the group consisting of hydrogen, lower alkyl having 1 to 8 carbon atoms, and M wherein M is a non-toxic pharmacologically inert metal cation, and
- R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, lower alkyl having 1 to 8 carbon atoms, lower alkenyl having 3 to 6 carbon atoms, lower alkoxy having 1 to 5 carbon atoms, hydroxy, nitro, amino, halo, phenyl, alkanoyl having 2 to 5 carbon atoms, or together they constitute a cycloalkene ring or an R-substituted cycloalkene ring wherein R is as defined above and said cycloalkene ring contains 5 to 7 annular atoms.
Dependencies are inferred from the claim text.