Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-04-28
1997-03-11
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546 16, C07D22120, A61K 31445
Patent
active
056101619
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/EP93/02951, filed Oct. 23, 1993. The present invention relates to novel therapeutic agents, to processes for their preparation, to pharmaceutical compositions containing them and to their use in the treatment of obesity and affective disorders such as depression and anxiety.
The present invention provides compounds of formula I ##STR2## and pharmaceutically acceptable salts thereof in which m is an integer from 1 to 3; selected from halo, hydroxy, alkoxy containing 1 to 3 carbon atoms, alkanoyl containing 2 or 3 carbon atoms, alkyl containing 1 to 3 carbon atoms, halogenated alkyl containing 1 to 3 carbon atoms, alkylthio containing 1 to 3 carbon atoms, alkylsulphinyl containing 1 to 3 carbon atoms, alkylsulphonyl containing 1 to 3 carbon atoms, cyano, nitro, amino optionally substituted by 1 or 2 alkyl groups each containing 1 to 3 carbon atoms, sulphamoyl optionally substituted by 1 or 2 alkyl groups each containing 1 to 3 carbon atoms, carbamoyl optionally substituted by 1 or 2 alkyl groups each containing 1 to 3 carbon atoms, or phenyl, or R.sub.1 is naphthyl; 6 carbon atoms, or alkoxyalkyl in which the alkoxy group contains 1 to 4 carbon atoms and the alkyl group contains 2 to 4 carbon atoms;
In preferred compounds of formula I, n is 4 or 5.
In preferred compounds of formula I, m is 1 or 2.
In preferred compounds of formula I, R.sub.1 is phenyl optionally substituted by one or more substituents selected from halo (for example fluoro, chloro, bromo or iodo), hydroxy, halogenated alkyl containing 1 to 3 carbon atoms in which halo is fluoro, alkoxy containing 1 or 2 carbon atoms or phenyl or R.sub.1 is naphthyl. In more preferred compounds of formula I, R.sub.1 is phenyl optionally substituted by one or more substituents selected from chloro, fluoro, hydroxy, trifluoromethyl, methoxy or phenyl or R.sub.1 is naphthyl. In especially preferred compounds of formula I, R.sub.1 is phenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 4-fluorophenyl, 3-(trifluoromethyl)phenyl, 4-hydroxyphenyl, 4-methoxyphenyl, 4-biphenylyl or 2-naphthyl.
In preferred compounds of formula I, R.sub.2 is H.
In preferred compounds of formula I, R.sub.3 is H, alkyl containing 1 to 3 carbon atoms, alkenyl containing 3 to 6 carbon atoms or alkoxyalkyl in which the alkoxy group contains 1 to 3 carbon atoms and the alkyl group contains 2 or 3 carbon atoms. In more preferred compounds of formula I, R.sub.3 is H, methyl, ethyl, propyl, allyl or 2-methoxyethyl. In especially preferred compounds of formula I, R.sub.3 is H.
In preferred compounds of formula I, R.sub.4 is hydroxy and R.sub.5 is H, R.sub.4 and R.sub.5 are both H, or R.sub.4 and R.sub.5 together represent a bond. In more preferred compounds of formula I, R.sub.4 and R.sub.5 together represent a bond.
Compounds of formula I may exist as salts with pharmaceutically acceptable acids. Examples of such salts include hydrochlorides, hydrobromides, sulphates, methanesulphonates, nitrates, maleares, acetates, citrates, fumarates, tartrates [e.g. (+)-tartrates, (-)-tartrates or mixtures thereof including racemic mixtures), succinates, benzoates and salts with amino acids such as glutamic acid. Compounds of formula I and their salts may exist in the form of solvates (for example hydrates).
Certain compounds of formula I may exist in more than one crystal form and the present invention includes each crystal form and the mixtures thereof.
Compounds of formula I which contain one or more chiral centres exist in different optically active forms. When compounds of formula I contain one chiral centre, the compounds exist in two enantiomeric forms and the present invention includes both enantiomers and mixtures of enantiomers. The enantiomers may be resolved by methods known to those skilled in the art, for example by formation of diastereoisomeric salts which may be separated, for example, by crystallisation; formation of diastereoisomeric derivatives or complexes which may be separated, for example, by crystallisation, gas-liquid or liquid chromatography; selective
REFERENCES:
patent: 4430335 (1984-02-01), Stupczewski et al.
patent: 4515960 (1985-05-01), Teetz
Bogeso, K. P. et al. J. Med. Chem. 30, 142-150 (1987).
Sundberg, R. J. et al. J. Org. Chem. 53, 976-983 (1988).
The international search report for PCT/EP93/02951.
Kloetzel et al, J.A.C.S. 83 (5), 1128-1132 (17 Mar. 1961).
Pearson et al, J.A.C.S. 114 (4), 1329-1345 (12 Feb. 1992).
Harris Paul J.
Kerrigan Frank
Shah Mukund J.
The Boots Company PLC
Wong King Lit
LandOfFree
Therapeutic agents does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Therapeutic agents, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Therapeutic agents will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-443768