Pyrazolothiazolopyrimidine derivatives

Details Pyrazolothiazolopyrimidine derivatives Pyrazolothiazolopyrimidine derivatives

1993-08-05

1996-06-18

Datlow, Philip I.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

544 34, 544250, 544251, C07D51314, A61K 31505

Patent

active

055279082

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to pyrazolothiazolopyrimidine derivatives which are useful as anti-inflammatory, analgesic, immunomodulatory and anti-ulcer agents.


BACKGROUND ART

6,7-Dihydro-2-methylpyrazolo[3,4-d]thiazolo[3,2-a]pyrimidin-4(2H)-one which is a tricyclic compound having a 6,7-dihydropyrazolo[3,4-d]thiazolo[3,2-a]pyrimidin-4-one skeleton and which has a substituent on a nitrogen atom at the 2-position is described in Liebigs Ann. Chem., 1121 (1987).


DISCLOSURE OF THE INVENTION

According to the present invention, there can be provided pyzazolothiazolopyrimidine derivatives represented by the following Formula (I): ##STR2## in which R.sup.1 represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, halogen or --NR.sup.3 R.sup.4 (in which R.sup.3 and R.sup.4 represent independently hydrogen, lower alkyl, lower alkanoyl or aroyl); when R.sup.2 is a substituent on the 1-position, X represents N or CH, and R.sup.2 represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl or lower alkoxycarbonyl; when R.sup.2 is a substituent on the 2-position, X represents N, and R.sup.2 represents --CR.sup.5 R.sup.6 R.sup.7 (in which R.sup.5 represents substituted or unsubstituted lower alkyl; and R.sup.6 and R.sup.7 represent independently hydrogen or lower alkyl), substituted or unsubstituted aryl, substituted or unsubstituted aralkyl or lower alkoxycarbonyl; Y represents O or S; Q represents --CR.sup.8 R.sup.9 CR.sup.10 R.sup.11 --(CH.sub.2).sub.n -- or --CR.sup.8 .dbd.CR.sup.9 --(CH.sub.2).sub.n -- (in which R.sup.8, R.sup.9, R.sup.10 and R.sup.11 represent independently hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl or lower alkoxycarbonyl; and n is an integer of 0 to 2) [which are hereinafter referred to as Compounds (I), and the same applies to the compounds of other formula numbers] or pharmaceutically acceptable salts thereof.
In the definitions of the groups in Formula (I), the lower alkyl moiety of the lower alkyl, the lower alkanoyl and the lower alkoxycarbonyl means a straight-chain or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl; neopentyl and hexyl. The aryl moiety of the aryl and the aroyl means a group such as phenyl and naphthyl. The aralkyl means an aralkyl group having 7 to 10 carbon atoms, such as benzyl and phenethyl. The halogen includes fluorin, chlorine, bromine and iodine. The substituted lower alkyl, the substituted aryl and the substituted aralkyl each has 1 to 3 independently-selected substituents, such as halogen, carboxyl and lower alkoxycarbonyl. The halogen and the lower alkyl moiety of the lower alkoxycarbonyl have the same meanings as defined above.
The pharmaceutically acceptable salts of Compounds (I) include acid addition salts and amino acid addition salts. Examples of the acid addition salts are inorganic acid addition salts such as hydrochloride and sulfate, and organic acid addition salts such as fumarate, tartrate, and citrate. Examples of the amino acid addition salts are salts with lysine, glycine and phenylalanine.
Compounds (I) in which R.sup.2 is hydrogen can be usually present as Compounds (I-1) and Compounds (I-2) which are tautomers. Compounds (I-2) are also included in the present invention, which are hereinafter shown as Compounds (I-1). ##STR3##
The processes for preparing Compounds (I) are described below.
In the processes shown below, if the defined groups are converted under the conditions of the processes or are not suitable for carrying out the processes, the processes can be readily carried out by applying thereto means conventionally used in organic synthetic chemistry, for example, protection or deprotection of functional groups.
Compound (Ia), i.e., Compound (i) in which X is N, Y is O, and R.sup.1 is hydrogen, ca

REFERENCES:
Masters et al, J. Amer. Chem Soc., 64, pp. 2709-2712 (1942).
Schmidt et al, Helv. Chim. Acta., 42, pp. 349-359 (1959).
Helvetica Chimica Acta, vol. 54, No. 6 (Sep. 1971) 1687-1691, Bormann et al.
Chemical Abstracts, vol. 84 No. 9 (1976), 59368p., Dashkerich et al.
Jan Svetlik, Liebigs Ann. Chem., vol. 12 (1987) 1121-1122.

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