Tricyclic thiazole and oxazole derivatives and pharmaceutical ag

Details Tricyclic thiazole and oxazole derivatives and pharmaceutical ag Tricyclic thiazole and oxazole derivatives and pharmaceutical ag

1994-03-04

1996-04-30

Ivy, C Warren

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

514248, 514293, 514250, 514338, 514366, 544 34, 544234, 546 81, 546271, 548151, C07D49814, A61K 31425

Patent

active

055125646

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP92/0215 filed Sep. 2, 1992.
The present invention concerns tricyclic thiazole and oxazole derivatives, processes for their production and pharmaceutical agents which contain these compounds.
The invention concerns tricyclic thiazolo- 2,3-a!pyrrole and oxazolo- 1,2-a!pyrrole derivatives of formula I ##STR2## in which
HET represents an aromatic, partially hydrogenated or hydrogenated heterocyclic ring with 3-7 ring atoms of which up to four atoms can be heteroatoms in which the heteroatoms can be the same or different and denote oxygen, nitrogen or sulphur, and the heterocycles can, if desired, carry an oxygen atom on one or several nitrogen atoms and HET can be substituted by one, two or three residues R.sup.1 which can be the same or different,
Y represents an oxygen or sulphur atom, or a SO or SO.sub.2 group,
X can be an oxygen or sulphur atom,
R denotes a straight-chained or branched, saturated or unsaturated aliphatic residue with 1-9 C atoms which can be substituted by phenyl or denotes a phenyl ring or a mono, bi or tricyclic carbocyclic ring with 7-15 C atoms or a heterocyclic mono, bi or tricyclic ring system each having five or six ring atoms and each ring system can contain 1-4 or 1-5 heteroatoms and the heteroatoms are nitrogen, sulphur or oxygen, in which the heteroatoms nitrogen and sulphur can, if desired, be substituted by oxygen atoms, and the aforementioned phenyl rings, the mono, bi or tricyclic carbocyclic rings or the heterocyclic mono, bi or tricyclic ring system is substituted, if desired, once or several times by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylmercapto, C.sub.1 -C.sub.6 -alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkinyl, C.sub.2 -C.sub.6 alkenyloxy, C.sub.2 -C.sub.6 -alkenylmercapto, C.sub.2 -C.sub.6 alkinyloxy, C.sub.2 -C.sub.6 alkinylmercapto, amino, C.sub.1 -C.sub.6 alkylamino, di-C.sub.1 -C.sub.6 alkylamino, C.sub.1 -C.sub.6 alkylcarbonylamino, C.sub.1 -C.sub.6 alkylaminocarbonyl, C.sub.1 -C.sub.6 alkoxycarbonyl, hydroxy, benzyloxy, phenylmercapto, phenyloxy, nitro, cyano, halogen, trifluoromethyl, azido, formylamino, carboxy or phenyl,
R.sup.1 denotes a hydrogen atom, a straight-chained or branched, saturated or unsaturated aliphatic residue with 1-6 C atoms or C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylmercapto, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, amino, C.sub.1 -C.sub.6 alkylamino, di-C.sub.1 -C.sub.6 alkylamino, sulfonamido, C.sub.1 -C.sub.6 alkoxycarbonyl, carboxy, halogen, hydroxy, nitro, cyano, azido, phenyl or benzyloxy,
R.sup.2 denotes hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylmercapto, amino, C.sub.1 -C.sub.6 alkylamino, di-C.sub.1 -C.sub.6 alkylamino, halogen, cyano, hydroxy, carboxy, C.sub.1 -C.sub.6 alkoxycarbonyl, aminocarbonyl or C.sub.1 -C.sub.6 alkylaminocarbonyl,
R.sup.3, R.sup.4, R.sup.5 have the same meaning as R.sup.2 and the residues R.sup.2, R.sup.3, R.sup.4 and R.sup.5 can independently of one another be the same or different, and R.sup.3 with R.sup.4 can, if desired, represent a double bond, as well as their tautomers, enantiomers, diastereomers and physiologically tolerated salts.
Thiazolo- 2,3-a!isoindoles are known as antiviral pharmaceutical agents from the earlier German Patent Application P 40 35 809.7.
The object of the present invention was to provide new tricyclic thiazolo- 2,3-a!pyrroles and oxazolo- 1,2-a!pyrroles with pharmacological properties. This object is achieved by the features characterized in the claims.
The compounds of the present invention have valuable pharmacological properties. In particular, they have an antiviral action and are suitable for the therapy and prophylaxis of infections that are caused by DNA viruses such as e.g. the herpes simplex virus, the cytomegaly virus, papilloma viruses, the varicella-zoster virus or Epstein-Barr virus or RNA viruses such as Toga viruses or in particular retroviruses such as the oncoviruses HTLV-I and

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Meyers, Tetrahedron Letters, vol. 30. No. 14, 1989, pp 1745-1748.
Bycroft et al, Tetrahedron Letters, vol. 24, No. 6, 1983, pp. 601-604.
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Hassan et al, Arch. Pharm. (Weinheim), vol. 324, No. 1, 1991, pp. 185-187.
Hassan et al, Chemical Abstracts, vol. 114, No. 21, Abstract No. 207,201j, p. 325, May 27, 1991.

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