3,4-dihydrothieno[2,3-d]pyrimidine compounds and their pharmaceu

Details 3,4-dihydrothieno[2,3-d]pyrimidine compounds and their pharmaceu 3,4-dihydrothieno[2,3-d]pyrimidine compounds and their pharmaceu

1989-11-02

1992-06-23

Shen, Cecilia

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

540600, 544115, 544117, 544250, 544278, 5142328, 5142342, 514267, 514258, A61K 31495, C07D49504

Patent

active

051243318

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to novel 2,3-dihydrothieno[2,3-d]pyrimidine compounds and their salts which are of use as immunoregulators, anticancer agents and so on, and to their use.


BACKGROUND ART

As for thieno[2,3-d]pyrimidine compounds, several kinds of similar compounds have already been reported. For example, in Chemical Abstracts, 79, 61411n, 3,4-dihydro-3-(2-chlorophenyl)-2,6-dimethyl-4-oxothieno[2,3-d]pyrimidine was synthesized as methaqualone analogue possessing a hypnotic action. Their actions, however, are weak. In Japanese Patent Application Examined Publication (Kokoku) No. 42271/1972, there are disclosed hexahydro-3-lower alkyl-[1]benzothieno[2,3-d]pyrimidin-1-one compounds which have a central nervous suppresive action, and an antiinflammatory action. In Japanese Patent Application Unexamined Publication (Kokai) No. 68197/1977, there are reported 3,4-dihydro-6-(N,N-dimethylsulfamoyl-4-oxothieno[2,3-d]pyrimidine as a synthetic intermediate for the compounds possessing an anti-microbial action, anti-virus action, antibacterial action and plant growth-regulating action.
In the specification of Indian Patent No. 151496, some kind of thienopyrimidine compounds usable for hyperlipidemic treatment are reported: In Drugs of the Future, vol. 10, No. 2, p 1885, it is described that 2-chloromethyl-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4(3H)-one which is encompassed in said Indian Patent is useful as a hypolipidemic agent.
In Arch. Pharm. vol. 309, pp. 908-913 (1976), it is reported that 2-aminomethyl-3-(2-methylphenyl)-5,6,7,8-tetrahydro(1)benzothieno[2,3-d]py rimidin-4(3H)-one compounds were synthesized as methaqualone analogues as mentioned above.
Meanwhile, the medicaments possessing an immunoregulating action have been in wide use recently for the prophylaxis or therapy of autoimmune diseases, the treatment of cancers, the amelioration of side-effects caused by anti-cancer agents, the therapy of infections diseases and so on. Particularly, as a medicament for chronic articular rheumatism which is one of the autoimmune diseases, the usefulness of the gold preparations for injections or oral administration is recognized, while such preparations have a defect of a number of side-effects. Accordingly, compounds having an excellent immunoregulating action and few side-effects have been demanded.


DISCLOSURE OF THE INVENTION

Under the foregoing situations, the present inventors conducted intensive studies for the purpose of providing excellent immunoregulators and, as a result, found that novel 2,3-dihydrothieno[2,3-d]pyrimidine compounds or their salts possessed not only remarkable immunoregulating actions but also anti-cancer actions, which culminated in the completion of the present invention.
This invention relates to 3,4-dihydrothieno[2,3-d]pyrimidine compounds of the general formula ##STR2## wherein A represents a straight or branched alkylene having 1 to 4 carbon atoms; R.sup.1 represents hydrogen, an alkyl, an aryl which may be substituted, or a group representable by --N(R.sup.7)(R.sup.8) wherein R.sup.7 and R.sup.8 are, the same or different, respectively hydrogen, an alkyl, an aralkyl which may be substituted, an aryl which may be substituted or a cycloalkyl, or R.sup.7 and R.sup.8 may, together with the adjacent nitrogen atom, form a ring in which nitrogen, oxygen, sulfur and >N-R.sup.9 may be interposed [wherein R.sup.9 represents hydrogen; an alkyl which may be substituted by hydroxy or an alkyl-substituted amino; a cycloalkyl; formyl, an aralkyl which may be substituted; an aryl which may be substituted; an arylalkenyl; a heterocyclic; an arylcarbonyl which may be substituted; or a heterocyclic carbonyl]; R.sup.2, R.sup.3 and R.sup.4 may be the same or different and respectively represent hydrogen, a halogen, hydroxy, an alkyl which may be substituted by a halogen, an alkoxy, nitro, cyano or a group of --N(R.sup.10)(R.sup.11) wherein R.sup.10 and R.sup.11 may be the same or different and respectively represent hydrogen, an alkyl, an alkanoyl or an arylcarbony

REFERENCES:
patent: 4146716 (1979-03-01), Cox et al.
CA 86: 139984t, 1977.
CA 104: 129858f, 1986.
M. J. Kulshreshtha et al, Journal of Indian Chemical Society, vol. LVIII, Oct. 1981, pp. 982-984.

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