Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-01-21
1999-07-13
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
544304, 544299, 544314, A61K 31505, C07D23960, C07D23954
Patent
active
059227273
DESCRIPTION:
BRIEF SUMMARY
The present invention relates, to new substituted pyrimidinedione derivatives, which are useful as an antiviral agent, treating agent for acquired immunodeficiency syndromes(AIDS), and pharmaceutically acceptable salts thereof. The invention also relates to process for the preparation of such derivatives and to pharmaceutical compositions containing the same as active ingredients.
Nowadays, various compounds such as AZT, DDC, DDI and D4T have been used as chemotherapeutic agents of AIDS and have a medical action mechanism with inhibition of the replication of AIDS virus. They also have drug tolerance and undesirable side effects due to their toxicity. carried out to develope antiviral chemotherapeutic agents with strong activity and with lower toxicity. Among them, researches have been focused on pyrimidine 6-substituted nucleoside compounds. But, N-1 substituted homocarbocyclic nucleoside derivatives were not developed as yet.
The present inventors carried out an intensive research on the N-1 substituted homocarbocyclic nucleoside derivatives and unexpectively found out the facts that the compounds have strong activity against HIV(AIDS, Acquired immunodeficiency syndromes) as well as a lower toxicity.
Accordingly, the present invention relates to new pyrimidinedione derivatives, 6-substituted pyrimidinedione homocarbocyclic nucleosides which are useful as an antiviral agent for treating acquired immunodeficiency syndromes(AIDS), and pharmaceutically acceptable salts thereof. ##STR3## wherein R.sub.1, R.sub.2, and R.sub.3 represents independently hydrogen atom, halogen atom, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 thioalkyl, C.sub.3 -C.sub.8 optionally substituted cyclicalkyl, unsaturated alkyl, substituted alkyl hydroxyl or aryl hydroxyl, C.sub.1 -C.sub.10 alkylamine, nitro, C.sub.1 -C.sub.4 lower ester, C.sub.1 -C.sub.4 lower alkoxy, C.sub.1 -C.sub.4 lower thioalkoxy; Z represents oxygen atom, sulfur atom, carbon atom and carbonyl group; X represents oxygen atom, sulfur atom; n represents an integer of 1-3; and (sub)cycloalk(en)yl represents ##STR4## in which R.sub.4 and R.sub.5 represents independently hydrogen atom, hydroxymethyl, protected hydroxymethyl, benzyl, substituted carbonyl, substituted alkylsulfonyl or arylsulfonyl, substituted silyl or the like.
C.sub.1 -C.sub.10 alkyl means straight or branch alkyl group such as methyl, ethyl, propyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, 2-methyl-pentyl or the like.
C.sub.1 -C.sub.10 thioalkyl means straight or branch thioalkyl group such as methylthio, ethylthio, propylthio, butylthio, isobutylthio, t-butylthio, pentylthio, isopentylthio, hexylthio, heptylthio, octylthio, 2-methyl-pentylthio or the like.
C.sub.3 -C.sub.8 optionally substituted cyclic alkyl means cyclic propyl, cyclic butyl, cyclic pentyl, methyl cyclic propyl, methyl cyclic butyl, methyl cyclic pentyl or the like.
C.sub.1 -C.sub.4 lower ester means a carboxylic group was esterified by lower alkyl group or the like.
C.sub.1 -C.sub.4 lower alkoxy means methoxy, ethoxy, propyloxy, butyloxy, isobutyloxy, t-butyloxy or the like.
C.sub.1 -C.sub.4 lower thioalkoxy means thiomethoxy, thioethoxy, thiopropyloxy, thiobutyloxy, thioisobutyloxy, thio t-butyloxy or the like.
The substituted carbonyl group means acetyl, benzoyl, substituted benzoyl or the like.
The substituted alkylsulfonyl, arylsulfonyl group means methanesulfonyl, para-toluenesulfonyl, benzenesulfonyl, para-nitrobenzenesulfonyl or the like.
The substituted silyl group means trimethylsilyl, dimethylphenylsilyl, t-butyldimethylsilyl or the like.
The present inventors had studied the active compound as an antiviral agent for long time. As a result, the present inventors unexpectively found out the facts that the compounds of the general formula(I) have excellent antiviral activity against HIV and very low toxicity.
In accordance with present invention, there are provided pharmaceutical compositions comprising one or more of the general formula(I) and their salts with a excellent antiviral activity against
REFERENCES:
patent: 4730001 (1988-03-01), Shealy et al.
patent: 5496824 (1996-03-01), Onishi et al.
Cho Eui-Hwan
Chung Sun-Gan
Joo Jeong-Ho
Kang Dong-Wook
Kim Byung-chul
Kessinger Ann M.
Samjin Pharmaceutical Co., Ltd
Shah Mukund J.
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