Use of thiazoloisoindolinone derivatives as antiviral medicament

Details Use of thiazoloisoindolinone derivatives as antiviral medicament Use of thiazoloisoindolinone derivatives as antiviral medicament

1993-07-20

1995-03-14

Henley, III, Raymond J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514934, A61K 31425

Patent

active

053977947

DESCRIPTION:

BRIEF SUMMARY
The subject of the present invention is the new use of thiazoloisoindolinone derivatives for the preparation of medicaments with antiviral action.
The present invention concerns the use of compounds of the general formula I ##STR2## for the preparation of medicaments for the treatment of viral or retroviral infections, whereby R signifies a hydrogen atom or a straight-chained or branched, saturated or unsaturated aliphatic radical with 1-7 carbon atoms, which can possibly be substituted by phenyl, or a phenyl ring, which can possibly be substituted one or more times by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, hydroxyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkylsulphonyl or halogen, such as fluorine, chlorine or bromine, n stands for the numbers 0, 1 or 2, as well as of their pharmacologically compatible salts and tautomers.
In U.S. Pat. No. 3,334,113 is described, inter alia, 9b-phenyl-2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-one as inflammation-inhibiting and anti-convulsive medicament. Further derivatives of thiazoloisoindolinone with similar action and lower toxicity are known from the Swiss Patent Application CH-469,733 (R=alkyl, n=0) and the Belgian Patent Application 659,528 or the U.S. Pat. No. 3,646,022, respectively.
In U.S. Pat. No. 2,860,985 and Belgian Patent Application 564,592, thiazoloisoindolinones are used for the stabilisation and as contrast agents for photographic emulsions.
Apart from in the above-mentioned Patent Applications, the synthesis of the compounds is also described in J. Org. Chem., 30, 1506 (1965), as well as in J. Org. Chem., 34, 165 (1969).
Surprisingly, it has now been found that these compounds display an outstanding anti-viral action and are, therefore, especially well suited for the treatment of viral and retroviral infections. Viral infections of mammals, especially of humans, are very widespread. In spite of intensive efforts, hitherto it has not been possible to make available chemotherapeutic agents which interfere causatively or symptomatically with occurrences of diseases caused virally or retrovirally with recognisable substantial success. At present, it is not possible to cure or chemotherapeutically favourably to influence the symptoms of certain viral diseases, such as for example acquired immune deficiency syndrome (AIDS), the AIDs-related complex (ARC) and its preliminary stages, herpes, cytomegalovirus (CMV), influenza and other viral infections. At present, for example, for the treatment of AIDS, there is almost exclusively available 3'-azido-3'-desoxythymidine (AZT), known as zidovudine or Retrovir.RTM.. However, AZT is characterised by a very narrow therapeutic range and by very severe toxicities already arising in the therapeutic range (Hirsch, M. S. (1988), J. Infec. Dis. 157, 427-431). The compounds of the general formula I do not possess these disadvantages. They act anti-virally without being cytotoxic in pharmacologically relevant doses.
The compounds of the present invention display valuable pharmacological properties. In particular, they are suitable for the therapy and prophylaxis of infections which are caused by DNA viruses, such as e.g. the herpes simplex virus, the cytomegalovirus, papillomaviruses, varicalla zoster virus or Epstein-Barr virus, or RNA viruses, for example toga-viruses, or especially retroviruses, such as onco-viruses HTLV-I and II, as well as the lentiviruses visna and the human immune deficiency virus HIV-1 and 2.
The compounds of the formula I appear to be especially suitable for the treatment of the clinical manifestations of the retroviral HIV infection in humans, such as the persistent, generalised lymphadenopathy (PGL), the advance stage of the AIDS-related complex (ARC) and the clinically complete manifestation of AIDS.
It could now be demonstrated that compounds of the general formula I inhibit the multiplication of DNA and RNA viruses at the stage of the virus-specific DNA and RNA transcription, respectively. Via the inhibition of the enzyme reverse transcriptase, the substances can influence the multipli

REFERENCES:
Yaechoan et al, 1989, Pharm Ther. vol. 40 pp. 329-348.

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