Carbamate derivatives

Details Carbamate derivatives Carbamate derivatives

1994-07-20

1996-01-23

Bond, Robert T.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

540518, C07D24312, A61K 3155

Patent

active

054865140

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP93/00099, filed Jan. 15, 1993.
This invention relates to novel 1,5-benzodiazepine derivatives, to processes for their preparation, to pharmaceutical compositions containing them and to their use in medicine.
In particular the invention relates to compounds which are potent and specific antagonists of gastrin and/or cholecystokinin (CCK).
Thus, the invention provides compounds of general formula (I) ##STR2## wherein R.sup.1 represents a phenyl, C.sub.3-7 cycloalkyl, bridged C.sub.7-11 cycloalkyl or C.sub.1-6 alkyl group which alkyl group may be substituted by a hydroxy, phenyl, C.sub.1-6 alkoxycarbonyl, C.sub.3-7 cycloalkyl or bridged C.sub.7-11 cycloalkyl group or R.sup.1 represents the group XYR.sup.4 wherein X is a C.sub.1-3 straight or branched alklene chain, Y is C.dbd.O, C(OR.sup.5).sub.2 or C(SR.sup.5).sub.2 and R.sup.4 is a C.sub.1-6 alkyl, optionally substituted phenyl, C.sub.3-7 cycloalkyl or bridged C.sub.7-11 cycloalkyl. substitutents may be 1 or 2 of halo, C.sub.1-4 alkyl, nitro, cyano, trifluoromethyl, trifluoromethoxy C.sub.1-4 alkylthio or (CH.sub.2).sub.n NR.sup.8 R.sup.9. atoms; group.
It will be appreciated that compounds of formula (I) possess at least one asymmetric carbon atom (namely the carbon atom occupying the 3-position of the diazepine ring) and the compounds of the invention thus include all stereoisomers and mixtures thereof including the racemates.
In the compounds of formula (I) `alkyl` when used as a substituent or part of a substituent group means that the group may be straight or branched. Thus, C.sub.1-6 alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl, n-pentyl, isopentyl neopentyl, n-hexyl, isohexyl, 1,3-dimethylbutyl, 3,3-dimethylbutyl, 2,3-dimethylbutyl.
For the group R.sup.1 the term C.sub.3-7 cycloalkyl as a group or pan of a group refers to a monocyclic alkyl group such as cyclopropyl, cylobutyl, cyclopentyl, cyclohexyl or cycloheptyl. The term bridged C.sub.7-11 cycloalkyl refers to groups such adamantyl, norbornanyl or norbornenyl.
For the groups R.sup.7 R.sup.8 and R.sup.9 the term C.sub.1-4 alkyl includes 3-4-cycloalkyl (e.g. cyclopropyl or cyclobutyl) as well as straight or branched chain alkyl groups as defined above.
Halogen in the definition of compounds of formula (I) may represent a fluoro, chloro, bromo or iodo substituent.
When R.sup.2 is a phenyl group substituted by a single substituent this may be in the ortho, para or more preferably in the meta position.
When R.sup.10 is halogen this is preferably chlorine or fluorine.
When m is 1 or 2 the halogen atom(s) e.g. chlorine or fluorine are preferably in the 7 and/or 8 positions.
The compounds of formula (I) posses at least one asymmetric carbon atom (namely the carbon atom occupying the 3-position of the diazeine ring) and particularly preferred compounds of the invention or those having the relative stereochemistry shown in formula (1a) ##STR3## wherein the solid wedge bond indicates the group is above the plane of the diazepine ring and the broken bond indicates the group is below the plane of the diazepine ring.
When R.sup.1 represents an alkyl group substituted by a hydroxyl group this is preferably a C.sub.3-6 alkyl group substituted by hydroxy. Examples of such groups include 2-hydroxypropyl, 2-hydroxy-3-methylbutyl and 2-hydroxy-3,3-dimethylbutyl 3-hydroxypropyl.
When R.sup.1 represent an alkyl group substituted by a C.sub.3-7 cycloalkyl group this is preferably a C.sub.2-3 alkyl group such as ethyl substituted by a C.sub.3-7 cycloalkyl group such as cyclopentyl.
When R.sup.1 is a bridged C.sub.7-11 cycloalkyl group this may be for example an adamantyl group such as 1-adamantyl or 2-adamantyl group or a 2-norbornanyl group.
When R.sup.1 is an alkyl group substituted by a bridged C.sub.7-11 cycloalkyl group this is preferably an ethyl group or more especially a methyl group substituted by a bridged C.sub.7-11 cycloalkyl group. Examples of suitable bridged cycloalkyl groups include adamantyl such as 1-adamantyl or 2-adamantyl, 2-n

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