Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-01-31
1998-05-26
Shah, Mukunk J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540557, A61K 3155, C07D49100
Patent
active
057564957
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/DE95/01029 filed Jul. 28, 1995.
The invention relates to new 3-substituted 3H-2,3-benzodiazepine derivatives, their production and use as pharmaceutical agents.
It is already known that selected 2,3-benzodiazepine derivatives have modulatory activity at quisqualate receptors and owing to this property are suitable as pharmaceutical agents for treating diseases of the central nervous system.
It has now been found that 3-substituted 3H-2,3-benzodiazepine derivatives of general formula I ##STR2## in which R.sup.1 and R.sup.2 are the same or different and mean hydrogen, C.sub.1 -C.sub.6 alkyl, nitro, halogen, the group --NR.sup.8 R.sup.9, --O--C.sub.1-4 alkyl or --CF.sub.3, ##STR3## R.sup.4 means optionally substituted C.sub.1 -C.sub.6 alkyl, R.sup.5 means hydrogen or optionally substituted C.sub.1 -C.sub.6 alkyl, substituted C.sub.1 -C.sub.6 alkyl or optionally substituted aryl, -C.sub.6 alkyl or the group ##STR4## R.sup.10 means hydrogen, optionally substituted C.sub.1 -C.sub.6 alkyl, optionally substituted aryl, the group --NR.sup.11 R.sup.12, --O--C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, C.sub.2-6 alkenyl or --O--C.sub.3-7 cycloalkyl, optionally substituted C.sub.1 -C.sub.6 alkyl or optionally substituted aryl, and
as well as their isomers and physiologically compatible salts, also are suitable for treating diseases of the central nervous system, whereby the compounds are distinguished by better properties compared to the above-mentioned prior art. Since an optically active center is present neither in 4-position nor in 5-position, the compounds of formula I also are easily accessible without separation of enantiomers.
Alkyl is defined as a straight-chain or branched alkyl radical, such as, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl or hexyl, which can be substituted--like the aryl radical--optionally by C.sub.1 -C.sub.6 alkoxy, halogen or C.sub.1 -C.sub.6 alkanoyl.
If a halogenated alkyl radical is present, the latter can be halogenated or perhalogenated in several places.
Halogen is defined as fluorine, chlorine, bromine and iodine.
The aryl radical can contain 6-10 carbon atoms, whereby phenyl is preferred.
Cycloalkyl is defined in each case as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl, especially C.sub.3-5 cycloalkyl.
The alkenyl radicals can be straight-chain or branched. For example, 2-propenyl, 3-methyl-2-propenyl, 2-butenyl, methallyl and vinyl can be mentioned.
Alkanoyl radicals are derivatives of aliphatic carboxylic acids, such as, for example, formic acid, acetic acid, propionic acid, butyric acid, caproic acid, valeric acid, trimethylacetic acid, i.a.
The physiologically compatible salts are derived from inorganic and organic acids. Suitable are inorganic acids, such as, for example, hydrohalic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid or organic acids, such as, for example, aliphatic or aromatic mono- or dicarboxylic acids such as formic acid, acetic acid, maleic acid, fumaric acid, succinic acid, lactic acid, tartaric acid, citric acid, oxalic acid, glyoxylic acid or sulfonic acids, for example, C.sub.1-4 alkanesulfonic acids such as methanesulfonic acid or benzenesulfonic acids that are optionally substituted by halogen or C.sub.1-4 alkyl, such as p-toluenesulfonic acid.
The compounds of formula I also comprise the E- or Z- isomers, or, if a chiral center is present, their racemates or enantiomers.
Preferred compounds of general formula I are those in which R.sup.1 means amino or nitro.
Especially preferred compounds of general formula I are those in which ##STR5## R.sup.4 means methyl or ethyl, R.sup.5, R.sup.6 and R.sup.7 mean hydrogen, substituted with halogen, the group --NR.sup.11 R.sup.12, C.sub.3-7 cycloalkyl, C.sub.2-6 alkenyl, --O--C.sub.1-6 alkyl or C.sub.1-6 alkyl, which is substituted in one or more places with fluorine, -C.sub.4 alkyl or phenyl and
The compounds of general formula I as well as their physiologically compatible salts can
REFERENCES:
Gatta et al., Derivatives of 2,3-Benzodiazepine(*), Farmaco, Edizione Scientifica, vol. 40, No. 12, pp. 942-955, 1985.
Andrasi Ferenc
Berzsenyi Pal
Birkas Erzsebet
Csuzdl Emese
Erdo Franciska
Coleman Brenda
Schering Aktiengesellschaft
Shah Mukunk J.
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