Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-03-03
1999-03-16
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
544231, 544293, A01N 4354, C07D23700, C07D23972
Patent
active
058831029
DESCRIPTION:
BRIEF SUMMARY
This is a 371 application of PCT/GB96/02496, filed Oct. 14, 1996.
This invention relates to novel compounds, processes for their preparation, compositions containing them and their use as pharmaceuticals.
According to the invention, we provide a compound of formula I: ##STR2## wherein R.sup.1 and R.sup.19 independently represent hydrogen, alkyl C1 to 6, alkoxy C1 to 6, alkylthio C1 to 6, halogen, hydroxyl or amino; containing one or two nitrogen atoms, or a 5-membered heterocyclic aromatic ring containing 1 to 3 heteroatoms selected from O, N and S, which phenyl or heterocyclic aromatic ring may be optionally substituted by alllyl C1 to 6, alkoxy C1 to 6, halogen, hydroxyl, alkylthio C1 to 6, cyano, trifluoromethyl, nitro, hydroxymethyl, amino, a group --(CH.sub.2).sub.c.NHCO.sub.2 R.sup.10, a group --(CH.sub.2).sub.c.NR.sup.5 R.sup.6, or a group --CO.sub.2 R.sup.11, optionally substituted by amino or a group --NHCO.sub.2 R.sup.10 ; and (CH.sub.2).sub.a.Z.(CH.sub.2).sub.b ; >NCOX(CH.sub.2).sub.n YR.sup.13, a group >NCSX(CH.sub.2).sub.n YR.sup.13, or a group >NCNHX(CH.sub.2).sub.n YR.sup.13 ; halogen atoms, cyano, quinolyl, phenyl, naphthyl, a 6-membered heterocyclic aromatic ring containing one or two nitrogen atoms, a 5-membered heterocyclic aromatic ring containing 1 to 3 heteroatoms selected from O, N and S, or a benzene ring fused with a 5-membered heterocyclic aromatic ring containing 1 to 3 heteroatoms selected from O, N and S; aromatic rings, said rings may be optionally substituted by one or more groups selected from alkyl C1 to 6, halogen, cyano, nitro, hydroxyl, alkoxy C1 to 6, trifluoromethyl, trifluoromethoxy, methanesulphonyl, sulphamoyl, --NR.sup.14 R.sup.15, --COOR.sup.16 or --CONR.sup.7 R.sup.8 ; ring containing one or two nitrogen atoms, or a 5-membered heterocyclic aromatic ring containing 1 to 3 heteroatoms selected from O, N and S substituted by 1 to 3 heteroatoms selected from O, N and S, hydroxyl, alkoxy C1 to 6, trifluoromethyl and trifluoromethoxy; aromatic ring containing at least one nitrogen atom, said ring may be optionally substituted by one or more oxo groups adjacent to the nitrogen, the ring being attached to the remainder of the molecule through one of the nitrogen atoms or otherwise; R.sup.16 independently represent hydrogen or alkyl C1 to 6; represent a pyrrolidine or piperidine ring; phenyl optionally substituted by one or more groups selected from allyl C1 to 6, halogen, cyano, nitro, hydroxyl, alkoxy C1 to 6, trifluoromethyl and trifluoromethoxy; (CH.sub.2).sub.a.Z.(CH.sub.2).sub.b, in which Z represents a group >NCOX(CH.sub.2).sub.n YR.sup.13, a group >NCSX(CH.sub.2).sub.n YR.sup.13, or a group >NCNHX(CH.sub.2).sub.n YR.sup.13 in which neither X nor Y represents a bond then n represents an integer 2 to 4; and (CH.sub.2).sub.a.Z.(CH.sub.2).sub.b, in which Z represents a group >NCOX(CH.sub.2).sub.n YCN, a group >NCSX(CH.sub.2).sub.n YCN, or a group >NCNHX(CH.sub.2).sub.n YCN, then Y represents a bond and either X also represents a bond or X does not represent a bond and n represents an integer 1 to 4;
Compounds of formula A: ##STR3## wherein R.sup.3 represents phenyl or benzyl, have already been disclosed by Finch et al. (1971), J Org. Chem., 36, 1463-1465.
Likewise compounds of formula B: ##STR4## wherein R.sup.1 represents hydrogen or chloro, have been disclosed by Carrington (1955), J. Chem. Soc., 2527-2528. Neither paper gives any useful pharmaceutical properties of the compounds.
Thus in a further aspect of the invention we provide a compound of formula I: ##STR5## wherein R.sup.1 and R.sup.19 independently represent hydrogen, alkyl C1 to 6, alkoxy C1 to 6, alkyilthio C1 to 6, halogen, hydroxyl or amino; containing one or two nitrogen atoms, or a 5-membered heterocyclic aromatic ring containing 1 to 3 heteroatoms selected from O, N and S, which phenyl or heterocyclic aromatic nng may be optionally substituted by alkyl C1 to 6, alkoxy C1 to 6, halogen, hydroxyl, alkylthio C1 to 6, cyano, trifluoromethyl, nitro, hydroxymethyl, amino, a grou
REFERENCES:
N. Finch et al. "Rearrangement of 3-amino-1-benzimidazole . . . " Journal of Organic Chemistry, vol. 36 No. 11, 1971, Easton US, pp. 1463-1465.
Carrington, H.C., "1:2-Dihydro-2:2-dimethylquinazolines. The Condensation of Acetone with . . . , " J. Chem. Soc. 1955, pp. 2527-2528.
Beaton Haydn
Hamley Peter
McInally Thomas
Pimm Austen
Tinker Alan
Astra Pharmaceuticals Limited
Ngo Tamthom T.
Shah Mukund J.
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