4a, 5a, 8a, 8b--tetrahydro-6H-ptrrolo [3,4':4,5]furo(3,2-b) pyridine-6,8[7H]-dione derivatives for use in controlling endoparasites and a method of producing said derivatives

The present invention relates to the use of 4a, 5a, 8a, 8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione derivatives of the general formula (I) and salts thereof, ##STR1## in which the radicals R.sup.1 to R.sup.5 have the meaning given in the description, and to novel 4a, 5a, 8a, 8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione derivatives and processes for their preparation.

CROSS-REFERENCES 
This application is a 371 of PCT/EP96/04346 filed Oct. 7, 1996. 
The present invention relates to the use of 4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives for the control of endoparasites, to novel 4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8 (7H)-dione 
derivatives and processes for their preparation. 
Some 4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives are already known. However, nothing is known of their use 
against endoparasites (cf. for example: T. Hisano et al. Chem. Pharm. 
Bull. 35 (3), (1987) pages 1049-1057; Heterocycles 29 (6), (1989) pages 
1029-1032; Chem. Pharm. Bull. 38 (3), (1990) pages 605-611; Chem. Pharm. 
Bull. 39 (1), (1991) pages 10-17). 
The present invention relates to: 
1. The use of 4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo-[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (I) and salts thereof, 
##STR2## 
in which R.sup.1 represents hydrogen, straight-chain or branched alkyl, 
cycloalkyl, arylalkyl, aryl, heteroaryl, heteroarylalkyl, which are 
optionally substituted, 
R.sup.2 represents hydrogen, straight-chain or branched alkyl, cycloalkyl, 
alkoxycarbonyl, which are optionally substituted, 
R.sup.1 and R.sup.2, together with the atoms to which they are bonded, 
represent a 5- or 6-membered ring, which can optionally be interrupted by 
oxygen, sulfur, sulfoxyl or sulfonyl and is optionally substituted, 
R.sup.3 represents hydrogen, straight-chain or branched alkyl, cycloalkyl, 
alkoxycarbonyl, which are optionally substituted, 
R.sup.4 represents hydrogen, straight-chain or branched alkyl, alkenyl, 
alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, 
heteroarylalkyl, amino, alkylamino, dialkylamino, cycloalkylamino, which 
are optionally substituted, 
R.sup.5 represents hydrogen, straight-chain or branched alkyl, alkenyl, 
alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, 
heteroarylalkyl, which are optionally substituted, formyl, 
alkoxydicarbonyl or optionally represents a radical from the group 
consisting of G.sup.1, G.sup.2, G.sup.3 and G.sup.4 
##STR3## 
in which R.sup.6 represents hydrogen, straight-chain or branched alkyl, 
cycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, which are 
optionally substituted, 
R.sup.6 and R.sup.7, together with the atoms to which they are bonded, 
represent a 5- or 6-membered ring, which can optionally be interrupted by 
oxygen, sulfur, sulfoxyl or sulfonyl and is optionally substituted, stand, 
R.sup.7 and R.sup.8 independently of one another represent hydrogen, 
straight-chain or branched alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, 
aryl, aryl-alkyl, heteroaryl, heteroarylalkyl, which are optionally 
substituted, or 
R.sup.7 and R.sup.8 together represent a spirocyclic ring which is 
optionally substituted, 
##STR4## 
can denote carboxyl, thiocarboxyl, --C.dbd.CH--NO.sub.2, --C.dbd.CH--CN, 
--C.dbd.N--R.sup.9, sulfoxyl, sulfonyl, --P(O)--OR.sup.10 or 
P(S)--OR.sup.10, 
R.sup.9 represents hydrogen, hydroxyl, alkoxy, alkylcarbonyl, 
halogenoalkylcarbonyl, alkylsulfonyl, nitro or cyano, and 
R.sup.10 represents hydrogen or alkyl, and 
Q represents straight-chain or branched alkyl, alkenyl, alkinyl, 
cycloalkyl, aryl, arylalkyl, hetaryl or hetarylalkyl, which are optionally 
substituted, or optionally represents a radical from the group consisting 
of G.sup.5 and G.sup.6 
##STR5## 
in which 
##STR6## 
can denote carboxyl, thiocarboxyl or sulfonyl, Y represents oxygen, 
sulfur or --NR.sup.12, 
R.sup.11, in the case where Y represents nitrogen, can denote a cyclic 
amino group linked via a nitrogen atom, 
R.sup.11 and R.sup.12 independently of one another represent hydrogen, 
straight-chain or branched alkyl, alkenyl, alkinyl, cycloalkyl, 
cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, which are 
optionally substituted, or 
R.sup.11 and R.sup.12, together with the adjacent N atom, for a carbocyclic 
5-, 6- or 7-membered ring system or for a 7 to 10-membered bicyclic ring 
system, which can optionally also be interrupted by oxygen, sulfur, 
sulfoxyl, sulfonyl, carbonyl, --N--O, --N.dbd., --NR.sup.14 -- or by 
quaternized nitrogen and is optionally substituted, 
R.sup.13 represents hydrogen or alkyl, 
R.sup.14 represents hydrogen, straight-chain or branched alkyl, alkenyl, 
alkinyl, cycloalkyl, cycloalkylalkyl, alkoxycarbonyl, alkylcarbonyl, 
cycloalkylcarbonyl, cyano, aryl, arylalkyl, heteroaryl, heteroarylalkyl 
stand which are optionally substituted, 
for control of endoparasites in medicine and veterinary medicine. 
The compounds of the formula (I) can occur as geometric and/or optical 
isomers or isomer mixtures of different composition, depending on the 
nature of the substituents. The invention relates both to the pure isomers 
and to the isomer mixtures. 
In the formula (I), the broken line can denote a single bond or represent 
one or two double bonds between the carbon atom which carries the 
substituent R.sup.2 and the adjacent carbon atom, and/or between the 
carbon atom and the adjacent nitrogen atom which carry the substituents 
R.sup.1 and R.sup.5. 
In the case where a double bond is present between the carbon atom which 
carries the substituent R.sup.1 and the adjacent nitrogen atom with a 
substituent R.sup.5, the compounds of the formula (I) are in the form of 
their salts. 
The 4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (I) and salts thereof 
##STR7## 
in which R.sup.1 represents hydrogen, straight-chain or branched alkyl 
having up to 4 carbon atoms, C.sub.3-6 -cycloalkyl, aryl-C.sub.1-2 -alkyl, 
aryl, heteroaryl, heteroaryl-C.sub.1-2 -alkyl, which are optionally 
substituted, 
R.sup.1 and R.sup.2, together with the atoms to which they are bonded, 
represent a 5- or 6-membered ring, which is optionally substituted, 
R.sup.2 and R.sup.3 independently of one another represent hydrogen, 
straight-chain or branched alkyl having up to 4 carbon atoms, 
halogenoalkyl, hydroxyalkyl, C.sub.1-4 -alkanoyloxyalkyl, C.sub.1-2 
-alkoxyalkyl, C.sub.1-2 -mercaptoalkyl, C.sub.1-2 -alkylthioalkyl, 
C.sub.1-2 alkylsulfinylalkyl, C.sub.1-2 alkylsulfonylalkyl, aminoalkyl, 
C.sub.1-6 -alkylaminoalkyl, C.sub.1-6 -dialkylaminoalkyl, C.sub.3-6 
-cycloalkylaminoalkyl, C.sub.3-6 -cycloalkyl, C.sub.1-4 -alkoxycarbonyl, 
R.sup.4 represents hydrogen, straight-chain or branched C.sub.1-6 -alkyl, 
halogeno-C.sub.1-6 -alkyl, hydroxy-C.sub.1-6 -alkyl, C.sub.1-4 
-alkanoyloxyalkyl, C.sub.1-2 -alkoxyalkyl, C.sub.1-4 
alkoxycarbonyl-C.sub.1-4 -alkyl, amino-C.sub.1-6 -alkyl, C.sub.1-6 
-alkylamino-C.sub.1-6 -alkyl, C.sub.1-6 -dialkylamino-C.sub.1-6 alkyl, 
C.sub.1-6 -trialkylammonium-C.sub.1-6 -alkyl halide, C.sub.2-6 -alkenyl, 
C.sub.2-6 -alkinyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkyl-C.sub.1-2 
-alkyl, aryl, aryl-C.sub.1-2 -alkyl, heteroaryl, heteroaryl-C.sub.1-2 
-alkyl, amino, C.sub.1-4 -alkylamino, C.sub.1-4 -dialkylamino, C.sub.3-7 
-cycloalkylamino, which are optionally substituted, 
R.sup.5 for hydrogen, straight-chain or branched C.sub.1-6 -alkyl, 
halogeno-C.sub.1-6 -alkyl, hydroxy-C.sub.1-6 -alkyl, C.sub.1-4 
-alkanoyloxyalkyl, C.sub.1-2 -alkoxyalkyl, amino-C.sub.1-6 -alkyl, 
C.sub.1-6 -alkylamino-C.sub.1-6 -alkyl, C.sub.1-6 -dialkylamino-C.sub.1-6 
-alkyl, C.sub.1-6 -trialkylammonium-C.sub.1-6 -alkyl halide, 
nitro-C.sub.1-4 -alkyl, cyano-C.sub.1-4 -alkyl, C.sub.1-4 
-alkoxycarbonyl-C.sub.1-4 -alkyl, carbamoyl-C.sub.1-4 -alkyl, 
carboxyl-C.sub.1-4 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 -alkinyl, 
C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkyl-C.sub.1-2 -alkyl, aryl, 
aryl-C.sub.1-2 -alkyl, heteroaryl, heteroaryl-C.sub.1-2 -alkyl, formyl, 
C.sub.1-4 -alkoxydicarbonyl, or for a radical from the group consisting of 
G.sup.1, G.sup.2, G.sup.3 and G.sup.4 
##STR8## 
in which R.sup.6 represents hydrogen, straight-chain or branched C.sub.1-6 
-alkyl, C.sub.3-6 -cycloalkyl, aryl-C.sub.1-2 -alkyl, heteroaryl-C.sub.1-2 
-alkyl, which are optionally substituted, 
R.sup.6 and R.sup.7, together with the atoms to which they are bonded, 
represent a 5- or 6-membered ring, which can optionally be interrupted by 
oxygen, sulfur, sulfoxyl or sulfonyl and is optionally substituted, stand, 
R.sup.7 and R.sup.8 independently of one another represent hydrogen, 
straight-chain or branched C.sub.1-6 -alkyl, halogeno-C.sub.1-6 -alkyl, 
hydroxy-C.sub.1-6 -alkyl, C.sub.1-4 -alkanoyloxy-C.sub.1-6 -alkyl, 
C.sub.1-2 -alkoxy-C.sub.1-6 -alkyl, mercapto-C.sub.1-6 -alkyl, C.sub.1-2 
-alkylthio-C.sub.1-6 -alkyl, C.sub.1-2 alkylsulfinyl-C.sub.1-6 -alkyl, 
C.sub.1-2 -alkylsulfonyl-C.sub.1-6 alkyl, carboxyl-C.sub.1-6 -alkyl, 
carbamoyl-C.sub.1-6 -alkyl, amino-C.sub.1-6 -alkyl, C.sub.1-6 
alkylamino-C.sub.1-6 -alkyl, C.sub.1-6 -dialkylamino-C.sub.1-6 -alkyl, 
guanidino-C.sub.1-6 -alkyl, which radical can optionally be substituted by 
one or two benzyloxycarbonyl radicals or by one, two, three or four 
C.sub.1-2 -alkyl radicals, (.sub.1-4 -alkoxycarbonylamino-C.sub.1-6 
-alkyl, C.sub.2-6 -alkenyl, C.sub.3-6 -cyclo-C.sub.1-2 -alkyl, C.sub.3-6 
-cycloalkyl-C.sub.1-2 -alkyl, and represent optionally substituted aryl, 
aryl-C.sub.1-2 -alkyl, heteroaryl, heteroaryl-C.sub.1-2 -alkyl, or 
R.sup.7 and R.sup.8 together represent a spirocyclic ring, 
##STR9## 
denotes carboxyl, thiocarboxyl, --C.dbd.CH--NO.sub.2, --C.dbd.CH--CN, 
--C.dbd.N--R.sup.9, sulfoxyl, sulfonyl, --P(O)--OR.sup.10 or 
P(S)--OR.sup.10, 
R.sup.9 represents hydrogen, hydroxyl, C.sub.1-4 -alkoxy, C.sub.1-4 
-alkylcarbonyl, halogeno-C.sub.1-4 -alkylcarbonyl, C.sub.1-4 
-alkylsulfonyl, nitro or cyano, and 
R.sup.10 represents hydrogen or C.sub.1-4 -alkyl, and 
Q represents straight-chain or branched C.sub.1-6 -alkyl, 
halogeno-C.sub.1-6 -alkyl, hydroxy-C.sub.1-6 -alkyl, C.sub.1-4 
-alkanoyloxyalkyl, C.sub.1-2 -alkoxyalkyl, mercaptoalkyl, C.sub.1-2 
-alkylthioalkyl, C.sub.1-2 -alkylsulfinylalkyl, C.sub.1-2 
-alkylsulfonylalkyl, carboxyalkyl, carbamoylalkyl, amino-C.sub.1-6 -alkyl, 
C.sub.1-6 -alkylamino-C.sub.1-6 -alkyl, C.sub.1-6 -dialkylamino-C.sub.1-6 
-alkyl, guanidino-C.sub.1-6 -alkyl, which radical can optionally be 
substituted by one or two benzyloxycarbonyl radicals, 
tert-butyloxycarbonyl radicals or by one, two, three or four C.sub.1-2 
-alkyl radicals, C.sub.1-4 -alkoxycarbonylaminoalkyl, C.sub.2-6 -alkenyl, 
C.sub.2-6 -alkinyl, C.sub.3-6 -cycloalkyl, aryl, aryl-C.sub.1-2 alkyl, 
heteroaryl or heteroaryl-C.sub.1-2 -alkyl, which are optionally 
substituted, or optionally represents a radical from the group consisting 
of G.sup.5 and G.sup.6 
##STR10## 
in which 
##STR11## 
can denote carboxyl, thiocarboxyl or sulfonyl, Y represents oxygen, 
sulfur or --NR.sup.12, 
R.sup.11, in the case where Y represents nitrogen, can denote a cyclic 
amino group linked by a nitrogen atom, 
R.sup.11 and R.sup.12 independently of one another represent hydrogen, 
straight-chain or branched C.sub.1-6 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 
-alkinyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkyl-C.sub.1-2 -alkyl, 
aryl, aryl-C.sub.1-2 -alkyl, heteroaryl, heteroaryl-C.sub.1-2 -alkyl, 
which are optionally substituted, or 
R.sup.11 and R.sup.12, together with the adjacent N atom, for a carbocyclic 
5-, 6- or 7-membered ring system, or for a 7 to 10-membered bicyclic ring 
system, which can optionally also be interrupted by oxygen, sulfur, 
sulfoxyl, sulfonyl, carbonyl, --N--O, --N.dbd., --NR.sup.14 -- or by 
quaternized nitrogen and is optionally substituted, 
R.sup.13 represents hydrogen or C.sub.1-4 -alkyl, 
R.sup.14 represents hydrogen, straight-chain or branched C.sub.1-6 -alkyl, 
C.sub.2-6 -alkenyl, C.sub.2-6 -alkinyl, C.sub.3-8 -cycloalkyl, C.sub.3-8 
-cycloalkyl-C.sub.1-2 -alkyl, C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 
-alkylcarbonyl, C.sub.3-6 -cycloalkylcarbonyl, cyano, aryl, aryl-C.sub.1-2 
-alkyl, heteroaryl, heteroaryl-C.sub.1-2 -alkyl stand, which are 
optionally substituted, 
and optical isomers and racemates thereof, 
are preferably used for control of endoparasites in medicine and veterinary 
medicine. 
The compounds of the general formula (I) are known in some cases and can be 
prepared by processes analogous to known processes. 
The invention furthermore relates to: 
2. Novel 4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Ia) and salts thereof, 
##STR12## 
in which R.sup.1 represents hydrogen, straight-chain or branched alkyl 
having up to 4 carbon atoms, C.sub.3-6 -cycloalkyl, aryl-C.sub.1-2 -alkyl, 
aryl, heteroaryl, heteroaryl-C.sub.1-2 -alkyl, which are optionally 
substituted, 
R.sup.2 and R.sup.3 independently of one another represent hydrogen, 
straight-chain or branched alkyl having up to 4 carbon atoms, 
halogenoalkyl, hydroxyalkyl, C.sub.1-4 -alkanoyloxyalkyl, C.sub.1-2 
-alkoxyalkyl, C.sub.1-2 -mercaptoalkyl, C.sub.1-2 -alkylthioalkyl, 
C.sub.1-2 -alkylsulfinylalkyl, C.sub.1-2 -alkylsulfonylalkyl, aminoalkyl, 
C.sub.1-6 -alkylaminoalkyl, C.sub.1-6 -dialkylaminoalkyl, C.sub.3-6 
-cycloalkylaminoalkyl, C.sub.3-6 -cycloalkyl, C.sub.1-4 -alkoxycarbonyl, 
R.sup.4 represents hydrogen, straight-chain or branched C.sub.1-6 -alkyl, 
halogeno-C.sub.1-6 -alkyl, hydroxy-C.sub.1-6 -alkyl, C.sub.1-4 
-alkanoyloxyalkyl, C.sub.1-2 -alkoxyalkyl, C.sub.1-4 
-alkoxycarbonyl-C.sub.1-4 -alkyl, amino-C.sub.1-6 -alkyl, C.sub.1-6 
-alkylamino-C.sub.1-6 -alkyl, C.sub.1-6 -dialkylamino-C.sub.1-6 -alkyl, 
C.sub.1-6 -trialkylammonium-C.sub.1-6 -alkyl halide, C.sub.2-6 -alkenyl, 
C.sub.2-6 -alkinyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkyl-C.sub.1-2 
-alkyl, aryl, aryl-C.sub.1-2 -alkyl, heteroaryl, heteroaryl-C.sub.1-2 
-alkyl, amino, C1-4-alkylamino, C.sub.1-4 -dialkylamino, C.sub.3-7 
-cycloalkylamino, which are optionally substituted, 
with the proviso in the case where 
R.sup.1 represents hydrogen, 
R.sup.2 and R.sup.3 represent methyl, 
R.sup.4 represents radicals other than methyl, n-butyl, phenyl, 2-, 3- or 
4-methylphenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-fluorophenyl, 
2-chloro, 4-fluorophenyl, 2-fluoro, 4-chlorophenyl, 3-chloro, 
4-fluorophenyl, 2-, 3- or 4-nitrophenyl, 4-methoxyphenyl 
and optical isomers and racemates thereof. 
3. Process for the preparation of the novel 4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Ia) and salts thereof, 
##STR13## 
in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meaning given 
under point 2, 
characterized in that 
a) pyridine N-oxides of the general formula (II) 
##STR14## 
in which R.sup.1, R.sup.2 and R.sup.3 have the meaning given under point 
2, are reacted with maleic acid imides of the general formula (III) 
##STR15## 
in which R.sup.4 has the meaning given under point 2, if appropriate in 
the presence of a diluent. 
The invention furthermore relates to: 
4. Novel 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione and 1, 
2, 4a, 5a, 8a, 
8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formulae (Ib) and (Ic) and salts thereof, 
##STR16## 
in which R.sup.1 represents hydrogen, straight-chain or branched alkyl 
having up to 4 carbon atoms, C.sub.3-6 -cycloalkyl, aryl-C.sub.1-2 -alkyl, 
aryl, heteroaryl, heteroaryl-C.sub.1-2 -alkyl, which are optionally 
substituted, 
R.sup.2 and R.sup.3 independently of one another represent hydrogen, 
straight-chain or branched alkyl having up to 4 carbon atoms, 
halogenoalkyl, hydroxyalkyl, C.sub.1-4 -alkanoyloxyalkyl, C.sub.1-2 
-alkoxyalkyl, C.sub.1-2 -mercaptoalkyl, C.sub.1-2 -alkylthioalkyl, 
C.sub.1-2 -alkylsulfinylalkyl, C.sub.1-2 alkylsulfonylalkyl, aminoalkyl, 
C.sub.1-6 -alkylaminoalkyl, C.sub.1-6 -dialkylaminoalkyl, C.sub.3-6 
-cycloalkyl-aminoalkyl, C.sub.3-6 -cycloalkyl, C.sub.1-4 -alkoxycarbonyl, 
R.sup.4 represents hydrogen, straight-chain or branched C.sub.1-6 -alkyl, 
halogeno-C.sub.1-6 -alkyl, hydroxy-C.sub.1-6 -alkyl, C.sub.1-4 
-alkanoyloxyalkyl, C.sub.1-2 -alkoxyalkyl, C.sub.1-4 
alkoxycarbonyl-C.sub.1-4 -alkyl, amino-C.sub.1-6 -alkyl, C.sub.1-6 
-alkylamino-C.sub.1-6 -alkyl, C.sub.1-6 -dialkylamino-C.sub.1-6 alkyl, 
C.sub.1-6 -trialkylammonium-C.sub.1-6 -alkyl halide, C.sub.2-6 -alkenyl, 
C.sub.2-6 -alkinyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkyl-C.sub.1-2 
-alkyl, aryl, aryl-C.sub.1-2 -alkyl, heteroaryl, heteroaryl-C.sub.1-2 
-alkyl, amino, C.sub.1-4 -alkylamino, C.sub.1-4 -dialkylamino, C.sub.3-7 
-cycloalkylamino, which are optionally substituted, 
R.sup.5 for hydrogen, straight-chain or branched C.sub.1-6 -alkyl, 
halogeno-C.sub.1-6 -alkyl, hydroxy-C.sub.1-6 -alkyl, C.sub.1-4 
-alkanoyloxyalkyl, C.sub.1-2 -alkoxyalkyl, amino-C.sub.1-6 -alkyl, 
C.sub.1-6 -alkylamino-C.sub.1-6 -alkyl, C.sub.1-6 -dialkylamino-C.sub.1-6 
-alkyl, C.sub.1-6 -trialkylammonium-C.sub.1-6 -alkyl halide, 
nitro-C.sub.1-4 -alkyl, cyano-C.sub.1-4 -alkyl, C.sub.1-4 
-alkoxycarbonyl-C.sub.1-4 -alkyl, carbamoyl-C.sub.1-4 -alkyl, 
carboxyl-C.sub.1-4 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 -alkinyl, 
C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkyl-C.sub.1-2 -alkyl, aryl, 
aryl-C.sub.1-2 alkyl, heteroaryl, heteroaryl-C.sub.1-2 -alkyl, formyl, 
C.sub.1-4 -alkoxydicarbonyl, or for a radical from the group consisting of 
G.sup.1, G.sup.2, G.sup.3 and G.sup.4 
##STR17## 
in which R.sup.6 represents hydrogen, straight-chain or branched C.sub.1-6 
-alkyl, C.sub.3-6 -cycloalkyl, aryl-C.sub.1-2 -alkyl, heteroaryl-C.sub.1-2 
-alkyl, which are optionally substituted, 
R.sup.6 and R.sup.7, together with the atoms to which they are bonded, 
represent a 5- or 6-membered ring, which can optionally be interrupted by 
oxygen, sulfur, sulfoxyl or sulfonyl and is optionally substituted, stand, 
R.sup.7 represent hydrogen, straight-chain or branched C.sub.1-6 
-alkyl,C.sub.2-4 -alkenyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 
-cycloalkyl-C.sub.1-2 -alkyl, and represent optionally substituted aryl, 
aryl-C.sub.1-2 -alkyl, heteroaryl, heteroaryl-C.sub.1-2 -alkyl, or 
R.sup.8 represents hydrogen or methyl, 
##STR18## 
can denote carboxyl, thiocarboxyl, --C.dbd.CH--NO.sub.2, --C.dbd.CH--CN, 
--C.dbd.N--R.sup.9, sulfoxyl, sulfonyl, --P(O)--OR.sup.10 or 
P(S)--OR.sup.10, 
R.sup.9 represents hydrogen, hydroxyl, C.sub.1-4 -alkoxy, C.sub.1-4 
-alkylcarbonyl, halogeno-C.sub.1-4 -alkylcarbonyl, C.sub.1-4 
-alkylsulfonyl, nitro or cyano, and 
R.sup.10 represents hydrogen or C.sub.1-4 -alkyl, and 
Q represents straight-chain or branched C.sub.1-6 -alkyl, 
halogeno-C.sub.1-6 -alkyl, hydroxy-C.sub.1-6 -alkyl, C.sub.1-4 
-alkanoyloxyalkyl, C.sub.1-2 -alkoxyalkyl, mercaptoalkyl, C.sub.1-2 
-alkylthioalkyl, C.sub.1-2 -alkylsulfinylalkyl, C.sub.1-2 
-alkylsulfonylalkyl, carboxyalkyl, carba-moylalkyl, amino-C.sub.1-6 
-alkyl, C.sub.1-6 alkylamino-C.sub.1-6 -alkyl, C.sub.1-6 
-dialkylamino-C.sub.1-6 -alkyl, guanidino-C.sub.1-6 -alkyl, which radical 
can optionally be substituted by one or two benzyloxycarbonyl radicals, 
tert-butyloxycarbonyl radicals or by one, two, three or four C.sub.1-2 
-alkyl radicals, C.sub.1-4 -alkoxycarbonylaminoalkyl, C.sub.2-6 -alkenyl, 
C.sub.2-6 -alkinyl, C.sub.3-6 -cycloalkyl, aryl, aryl-C.sub.1-2 -alkyl, 
heteroaryl or heteroaryl-C.sub.1-2 -alkyl, which are optionally 
substituted, or optionally represents a radical from the group consisting 
of G.sup.5 and G.sup.6 
##STR19## 
in which 
##STR20## 
can denote carboxyl, thiocarboxyl or sulfonyl, Y represents oxygen, 
sulfur or --NR.sup.12, 
R.sup.11, in the case where Y represents nitrogen, can denote a cyclic 
amino group linked by a nitrogen atom, 
R.sup.11 and R.sup.12 independently of one another represent hydrogen, 
straight-chain or branched C.sub.1-6 -alkyl, C.sub.2-6 -alkenyl, C.sub.2-6 
-alkinyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkyl-C.sub.1-2 -alkyl, 
aryl, aryl-C.sub.1-2 -alkyl, heteroaryl, heteroaryl-C.sub.1-2 -alkyl, 
which are optionally substituted, or 
R.sup.11 and R.sup.12, together with the adjacent N atom, for a carbocyclic 
5-, 6- or 7-membered ring system, or for a 7 to 10-membered bicyclic ring 
system, which can optionally also be interrupted by oxygen, sulfur, 
sulfoxyl, sulfonyl, carbonyl, --N--O, --N.dbd., --NR.sup.14 -- or by 
quaternized nitrogen and is optionally substituted, 
R.sup.13 represents hydrogen or C.sub.1-4 -alkyl, 
R.sup.14 represents hydrogen, straight-chain or branched C.sub.1-6 -alkyl, 
C.sub.2-6 -alkenyl, C.sub.2-6 -alkinyl, C.sub.3-8 -cycloalkyl, C.sub.3-8 
-cycloalkyl-C.sub.1-2 -alkyl, C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 
-alkylcarbonyl, C.sub.3-6 -cyclo-alkylcarbonyl, cyano, aryl, 
aryl-C.sub.1-2 -alkyl, heteroaryl, heteroaryl-C.sub.1-2 -alkyl stand, 
which are optionally substituted, 
and optical isomers and racemates thereof 
5. Process for the preparation of the novel 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione and/or 
1, 2, 4a, 5a, 8a, 
8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]-pyridine-6,8(7H)-dione 
derivatives of the general formulae (Ib) and (Ic) and salts thereof, 
##STR21## 
in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meaning 
given under point 4, characterized in that 
the 4a, 5a, 8a, 8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b] 
pyridine-6,8(7H)-dione derivatives, obtainable, for example, according to 
process 3, of the general formula (Ia) 
##STR22## 
in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meaning given 
under point 2, 
are hydrogenated in a first reaction step in the presence of suitable 
catalysts to form 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-n]pyridine-6,8(7H-dione and/or 
1,2,4a, 5a, 8a, 
8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Id) and (Ie) 
##STR23## 
in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meaning given 
further above, 
or 
in order to selectively prepare the new derivatives of the general formula 
(Ie) and salts thereof, the derivatives of the general formula (Ia) are 
first reacted with methyl halides of the general formula (IV) 
EQU Me-Hal (IV) 
in which 
Hal represents halogen, in particular fluorine, chlorine, bromine or 
iodine, if appropriate in the presence of diluents, and then the N.sup.1 
-methylammonium halides formed, of the general formula (V) 
##STR24## 
are hydrogenated in the presence of a suitable diluent, after which the 
resulting N.sup.1 -methyl derivative of the general formula (VI) 
##STR25## 
in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meaning mentioned 
further above, is demethylated at the N.sup.1 atom to form (1e) and then, 
in a second reaction step, the resulting 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione and/or 
1, 2, 4a, 5a, 8a, 
8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]-pyridine-6,8(7H)-dione 
derivatives of the general formulae (Id) and (Ie) 
##STR26## 
in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meaning given 
above, 
a) are reacted with compounds of the general formula (VII) 
EQU R.sup.5 -E (VII) 
in which 
R.sup.5 has the meaning given above, and 
E represents an electron-withdrawing leaving group, if appropriate in the 
presence of diluents and if appropriate in the presence of a basic 
reaction auxiliary, or 
b) with compounds of the general formula (VIII) 
##STR27## 
in which A represents a suitable acceptor group, such as, for example, 
nitro, nitrile, carbamoyl or R.sup.13 O--CO--, and 
R.sup.8 and R.sup.13 have the meaning given under point 4, or in that 
c) are reacted with an epoxide of the general formula (IX) 
##STR28## 
in which R.sup.5 has the meaning given under point 4, if appropriate in 
the presence of a catalyst or in the presence of a basic reaction 
auxiliary, if appropriate in the presence of diluents, or 
d) are reacted with compounds of the general formula (X) 
##STR29## 
in which G, Q and X have the meaning given under point 4, and 
W represents a suitable leaving group, such as, for example, halogen, 
alkoxy, alkylthio or aryloxy, if appropriate in the presence of a 
catalyst, if appropriate in the presence of an acid-binding agent and if 
appropriate in the presence of diluents, or in that 
to prepare the novel 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione and/or 
1, 2, 4a, 5a, 8a, 
8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-(7H)-dione 
derivatives of the general formulae (Ib) and (Ic) and salts thereof, 
in which the group 
##STR30## 
represents carboxyl, e) are reacted with a carboxylic acid anhydride of 
the general formula (XI) 
EQU (Q-C.dbd.O).sub.2 O (XI) 
in which 
Q has the meaning given under point 4, if appropriate in the presence of a 
catalyst, 
if appropriate in the presence of diluents, or 
f) are reacted with amino sows derivatives of the general formula (XII) 
##STR31## 
in which G, Q, X, R.sup.6, R.sup.7 and R.sup.8 have the meaning given 
under point 4, or carboxyl-activated derivatives thereof, 
if appropriate in the presence of a catalyst, if appropriate in the 
presence of an acid-binding agent and if appropriate in the presence of 
diluents, or 
g) are reacted with compounds of the general formulae (XIII) or (XIV) 
EQU R.sup.11 --N.dbd.C.dbd.X (XIII) 
##STR32## 
in which the radicals R.sup.11, G.sup.1, X, X.sup.1 and Y have the meaning 
given under point 1, 
if appropriate in the presence of a catalyst, if appropriate in the 
presence of an acid-binding agent and if appropriate in the presence of 
diluents, or in that 
to prepare the novel 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione and/or 
1, 2, 4a, 5a, 8a, 
8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formulae (Ib) and (Ic) and salts thereof, 
in which the group 
##STR33## 
represents carboxyl and Y represents oxygen, h) in a third reaction step 
are reacted with carbon dioxide and an alkali metal carbonate of the 
general formula (XV) 
EQU M.sub.2 CO.sub.3 (XV) 
in which 
M represents a monovalent alkali metal cation, preferably lithium, sodium, 
potassium or caesium, in particular potassium or caesium, 
and then, in a fourth reaction step, the resulting alkali metal salts of 
compounds of the general formulae (XVI) and (XVII) 
##STR34## 
in which the radicals R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the 
meaning given under point 4, 
M represents one metal cation equivalent bonded in salt form, are reacted 
with an alkylating agent of the formula (VIIa) 
EQU R.sup.11 -Hal (VIIa) 
in which 
R.sup.11 has the meaning given under point 4, and 
Hal represents halogen, such as fluorine, chlorine, bromine or iodine, 
if appropriate in the presence of a basic reaction auxiliary and if 
appropriate in the presence of diluents, or in that 
i) 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]-pyridine-6,8(7H)-dione 
and/or 1, 2, 4a, 5a, 8a, 8b-hexahydro-6H-pyrrolo [3',4,':4,5] furo 
[3,2-b]pyridine-6,8(7H)-dione derivatives of the general formulae (Id) and 
(Ie) 
##STR35## 
in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4, G, W and X have 
the meaning given under point 4, 
if appropriate in the presence of a catalyst, if appropriate in the 
presence of an acid-binding agent and if appropriate in the presence of 
diluents, are reacted with compounds of the general formula (XVIII) 
EQU R.sup.11 --Y--H (XVIII) 
in which 
the radicals R.sup.11 and Y have the meaning given above under point 4. 
The general formula (I) provides a general definition of the 4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]py-ridine-6,8(7H)-dione 
derivatives and salts thereof according to the invention. 
The 4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]py-ridine-6,8(7H)-dione 
derivatives and acid addition salts and metal salt complexes thereof 
according to the invention have a very good endoparasiticidal, in 
particular anthelmintic, action and can preferably be employed in the 
field of veterinary medicine. 
Optionally substituted alkyl, by itself or as a constituent of a radical, 
in the general formulae denotes straight-chain or branched alkyl having 
preferably 1 to 6, in particular 1 to 4, carbon atoms. Examples which may 
be mentioned are optionally substituted methyl, ethyl, n-propyl, 
isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, 
1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 
1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 
1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 
1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 
1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 
1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylpropyl and 
2-ethylbutyl. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 
sec-butyl and tert-butyl may be mentioned as preferred. 
Optionally substituted alkenyl, by itself or as a constituent of a radical, 
in the general formulae denotes straight-chain or branched alkenyl having 
preferably 1 to 6, in particular 1 to 4, carbon atoms. Examples which may 
be mentioned are optionally substituted vinyl, 2-propenyl, 2-butenyl, 
3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 
3-pentenyl, 4-pentenyl, 1-methyl-2-bute-nyl, 2-methyl-2-butenyl, 
3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 
3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 
1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 
1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 
4-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 
1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 
4-methyl-4-pentenyl, 1,1-diemethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 
1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 
1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 
2,3-dimethyl-3-butenyl, 1-ethyl-2-bute-nyl, 1-ethyl-3-butenyl, 
2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-prope-nyl, 
1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl. Optionally 
substituted ethenyl, 2-propenyl, 2-butenyl or 1-methyl-2-propenyl may be 
mentioned as preferred. 
Optionally substituted alkinyl, by itself or as a constituent of a radical, 
in the general formulae denotes straight-chain or branched alkinyl having 
preferably 1 to 6, in particular 1 to 4, carbon atoms. Examples which may 
be mentioned are optionally substituted ethinyl, 2-propinyl, 2-butinyl, 
3-butinyl, 1-methyl-2-propinyl, 2-pentinyl, 3-pentinyl, 4-pentinyl, 
1-methyl-3-butinyl, 2-methyl-3-butinyl, 1-methyl-2-butinyl, 
1,1-dimethyl-2-propinyl, 1-ethyl-2-propinyl, 2-hexinyl, 3-hexinyl, 
4-hexinyl, 5-hexinyl, 1-methyl-2-pentinyl, 1-methyl-3-pentinyl, 
1-methyl-4-pentinyl, 2-methyl-3 -pentinyl, 2-methyl-4-pentinyl, 
3-methyl-4-pentinyl, 4-methyl-2-pentinyl, 1,1-dimethyl-2-b-butinyl, 
1,1-dimethyl-3-butinyl, 1,2-dimethyl-3-butinyl, 2,2-dimethyl-3-butinyl, 
1-ethyl-3-butinyl, 2-ethyl-3-butinyl and i-ethyl-1-methyl-2-propinyl. 
Optionally substituted ethinyl, 2-propinyl or 2-butinyl may be mentioned as 
preferred. 
Optionally substituted cycloalkyl, by itself or as a constituent of a 
radical, in the general formulae denotes mono-, bi- and tricyclic 
cycloalkyl, prefer-ably having 3 to 10, in particular having 3, 5 or 7, 
carbon atoms. Examples which may be mentioned are optionally substituted 
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 
bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and adamantyl. 
Halogenoalkyl, by itself or as a constituent of a radical, in the general 
formulae contains 1 to 4, in particular 1 or 2, carbon atoms, and 
preferably 1 to 9, in particular 1 to 5, identical or different halogen 
atoms, preferably fluorine, chlorine and bromine, in particular fluorine 
and chlorine. Examples which may be mentioned are trifluoromethyl, 
trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chloromethyl, 
bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 
2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 
pentafluoroethyl and pentafluoro-tert-butyl. 
Optionally substituted alkoxy, by itself or as a constituent of a radical, 
in the general formulae denotes straight-chain or branched alkoxy having 
preferably 1 to 6, in particular 1 to 4, carbon atoms. Examples which may 
be mentioned are optionally substituted methoxy, ethoxy, n-propoxy, 
isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy. 
Optionally substituted halogenoalkoxy, by itself or as a constituent of a 
radical, in the general formulae denotes straight-chain or branched 
halogenoalkoxy having preferably 1 to 6, in particular 1 to 4, carbon 
atoms. Examples which may be mentioned are optionally substituted 
difluoromethoxy, trifluoromethoxy, trichloromethoxy, 
chlorodifluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 
1,1,2,2-tetrafluoroethoxy, 2,2,2-trifluoroethoxy and 
2-chloro-1,1,2-trifluoroethoxy. 
Optionally substituted alkylthio, by itself or as a constituent of a 
radical, in the general formulae denotes straight-chain or branched 
alkylthio having pre-ferably 1 to 6, in particular 1 to 4, carbon atoms. 
Examples which may be mentioned are optionally substituted methylthio, 
ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, 
sec-butylthio and tert-butylthio. 
Optionally substituted halogenoalkylthio, by itself or as a constituent of 
a radical, in the general formulae denotes straight-chain or branched 
halogenoalkylthio having preferably 1 to 6, in particular 1 to 4, carbon 
atoms. Examples which may be mentioned are optionally substituted 
difluoromethylthio, trifluoromethylthio, trichloromethylthio, 
chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 
2,2-di-fluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 
2,2,2-trifluoroethylthio and 2-chloro-1,1,2-trifluoroethylthio. 
Optionally substituted alkylcarbonyl, by itself or as a constituent of a 
radical, in the general formulae denotes straight-chain or branched 
alkylcarbonyl having preferably 1 to 6, in particular 1 to 4, carbon 
atoms. Examples which may be mentioned are optionally substituted 
methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, 
n-butylcarbonyl, isobutylcarbonyl, sec-bu-tyl-carbonyl and 
tert-butylcarbonyl. 
Optionally substituted cycloalkylcarbonyl, by itself or as a constituent of 
a radical, in the general formulae denotes mono-, bi- and tricyclic 
cycloalkylcarbonyl, preferably having 3 to 10, in particular having 3, 5 
or 7, carbon atoms. Examples which may be mentioned are optionally 
substituted cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, 
cyclohexyl-carbonyl, cycloheptylcarbonyl, cyclooctylcarbonyl, 
bicyclo[2.2.1]-heptylcarbonyl, bicyclo[2.2.2]octylcarbonyl and 
adamantylcarbonyl. 
Optionally substituted alkoxycarbonyl, by itself or as a constituent of a 
radical, in the general formulae denotes straight-chain or branched 
alkoxycarbonyl having preferably 1 to 6, in particular 1 to 4, carbon 
atoms. Examples which may be mentioned are optionally substituted 
methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, 
n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl and 
tert-butoxycarbonyl. 
Aryl is, for example, a mono-, di- or polynuclear aromatic radical, such as 
phenyl, naphthyl, tetrahydronaphthyl, indanyl, fluorenyl and the like, 
preferably phenyl or naphthyl. 
Optionally substituted aryl in the general formulae preferably denotes 
optionally substituted phenyl or naphthyl, in particular phenyl. 
Optionally substituted arylalkyl in the general formulae preferably denotes 
arylalkyl which is optionally substituted in the aryl part and/or alkyl 
and has preferably 6 or 10, in particular 8 carbon atoms in the aryl part 
(preferably phenyl or naphthyl, in particular phenyl) and preferably 1 to 
4, in particular 1 or 2, carbon atoms in the alkyl part, it being possible 
for the alkyl part to be straight-chain or branched. Optionally 
substituted benzyl and phenylethyl may be mentioned as examples and as 
preferred. 
Optionally substituted hetaryl, by itself or as a constituent of a radical, 
in the general formulae denotes 5- to 7-membered rings having preferably 1 
to 3, in particular 1 or 2, identical or different heteroaromatics. 
Heteroatoms in the heteroaromatics are oxygen, sulfur or nitrogen. 
Optionally substituted furyl, thienyl, pyrazolyl, imidazolyl, 1,2,3- and 
1,2,4-triazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,3,4-, 
1,2,4- and 1,2,5-oxadiazolyl, azepinyl, pyrrolyl, pyridyl, piperazinyl, 
pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-, 1,2,4- and 1,2,3-triazinyl, 
1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, oxepinyl, thiepinyl and 
1,2,4-diazepinyl, may be mentioned as examples and as preferred. 
The optionally substituted radicals of the general formulae can carry one 
or more, preferably 1 to 3, in particular 1 to 2, identical or different 
substituents. Substituents which may be mentioned as examples and as 
preferred are: 
alkyl having preferably 1 to 4, in particular 1 to 2, carbon atoms, such as 
methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and 
tert-butyl; alkoxy having preferably 1 to 4, in particular 1 to 2, carbon 
atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, 
isobutoxy, sec-butoxy and tert-butoxy; alkylthio, such as methylthio, 
ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, 
sec-butylthio and tert-butylthio; halogenoalkyl having preferably 1 to 4, 
in particular 1 to 2, carbon atoms and preferably 1 to 5, in particular 1 
to 3, halogen atoms, the halogen atoms being identical or different and 
the halogen atoms being preferably fluorine, chlorine or bromine, in 
particular fluorine or chlorine, such as difluoromethyl, trifluoromethyl, 
trichloromethyl; hydroxyl; halogen, prefer-ably fluorine, chlorine, 
bromine and iodine, in particular fluorine and chlorine; cyano; nitro; 
amino; monoalkyl- and dialkylamino having preferably 1 to 4, in particular 
1 or 2, carbon atoms per alkyl group, such as methylamino, 
methylethylamino, dimethyl-amino, n-propylamino, isopropyl amino, 
methyl-n-butyl amino; alkylcarbonyl radicals such as methylcarbonyl; 
alkoxycarbonyl having preferably 2 to 4, in particular 2 to 3, carbon 
atoms, such as methoxycarbonyl and ethoxycarbonyl; alkylsulfinyl having 1 
to 4, in particular 1 to 2, carbon atoms; halogenosilfinyl having 1 to 4, 
in particular 1 to 2, carbon atoms and 1 to 5 halogen atoms, such as 
trifluoromethylsulfinyl; sulfonyl (--SO.sub.2 --OH); alkylsulfonyl having 
preferably 1 to 4, in particular 1 or 2, carbon atoms, such as 
methylsulfonyl and ethylsulfonyl; halogenoalkylsulfonyl having 1 to 4, in 
particular 1 to 2, carbon atoms and 1 to 5 halogen atoms, such as 
trifluoromethylsulfonyl, perfluoro-n-butylsulfonyl, 
perfluoro-isobutylsulfonyl; arylsulfonyl having preferably 6 or 10 aryl 
carbon atoms, such as phenylsulfonyl; acyl, aryl, aryloxy, hetaryl, 
hetaryloxy, which in their turn can carry one of the abovementioned 
substituents, and the formimino radical (--HC.dbd.N--O-alkyl). 
Possible suitable cyclic amino groups are heteroaromatic or aliphatic ring 
systems having one or more nitrogen atoms as the heteroatom, in which the 
heterocyclic rings can be saturated or unsaturated, can be one ring system 
or several fused ring systems, and optionally contain further heteroatoms, 
such as nitrogen, oxygen and sulfur and the like. Cyclic amino groups can 
furthermore also denote a spiro ring or a bridged ring system. The number 
of atoms which form cyclic amino groups is not limited, for example in the 
case of a single-ring system, they comprise 3 to 8 atoms, and in the case 
of a three-ring system, they comprise 7 to 11 atoms. 
Examples which may be mentioned of cyclic amino groups with saturated and 
unsaturated monocyclic groups with a nitrogen atom as the heteroatom are 
1-azetidinyl, pyrrolidino, 2-pyrrolin-1-yl, 1-pyrrolyl, piperidino, 
1,4-dihydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, homopiperidino; 
examples which may be mentioned of cyclic amino groups with saturated and 
unsaturated monocyclic groups with two or more nitrogen atoms as 
heteroatoms are 1-imidazolidinyl, 1-imidazolyl, 1-pyrazolyl, 1-triazolyl, 
1-tetrazolyl, 1-piperazinyl, 1-homopiperazinyl, 
1,2-dihydro-pyridazin-1-yl, 1,2-dihydro-pyrimidin-1-yl, 
perhydropyrimidin-1-yl and 1,4-diazacycloheptan-1-yl; examples which may 
be mentioned of cyclic amino groups with saturated and unsaturated 
monocyclic groups with one to three nitrogen atoms and one to two sulfur 
atoms as heteroatoms are thiazolidin-3-yl, isothiazolin-2-yl, 
thiomorpholino or dioxothiomorpholino; examples which may be mentioned of 
cyclic amino groups with saturated and unsaturated fused cyclic groups are 
indol-1-yl, 1,2-dihydrobenzimidazol-1-yl, 
perhydropyrrolo[1,2-a]pyrazin-2-yl; an example which may be mentioned of 
cyclic amino groups with spirocyclic groups is 2-azaspiro[4,5]decan-2-yl; 
an example which may be mentioned of cyclic amino groups bridged 
heterocyclic groups is 2-azabicyclo[2,2,1]heptan-7-yl. 
Preferred compounds are those of the formula (I) and salts thereof 
##STR36## 
in which R.sup.1 represent hydrogen, straight-chain or branched C.sub.1-4 
-alkyl, in particular methyl, ethyl, propyl, isopropyl, isobutyl, 
sec-butyl, tert-butyl, C.sub.3-6 -cycloalkyl, in particular cyclopropyl, 
cyclobutyl, cyclopentyl, cyclohexyl, aryl, heteroaryl, which are 
optionally substituted, 
R.sup.1 and R.sup.2, together with the atoms to which they are bonded, 
represent a 5- or 6-membered ring, which is optionally substituted, 
R.sup.2 and R.sup.3 independently of one another represent hydrogen, 
straight-chain or branched branched C.sub.1-4 -alkyl, in particular 
methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, 
halogeno-C.sub.1-4 -alkyl, in particular chloromethyl, bromomethyl, 
difluoromethyl, trifluoromethyl or trichloromethyl, hydroxy-C.sub.1-4 
-alkyl, in particular hydroxymethyl, C.sub.1-4 -alkanoyloxy-C.sub.1-4 
-alkyl, in particular acetoxymethyl, C.sub.1-2 -alkoxyalkyl, in particular 
methoxymethyl, C.sub.1-2 -alkylthioalkyl, in particular methylthiomethyl, 
C.sub.1-2 -alkylsulfinyl-C.sub.1-4 -alkyl, in particular 
methylsulfinylmethyl, C.sub.1-2 -alkylsulfonyl-C.sub.1-4 -alkyl, in 
particular methylsulfonylmethyl, amino-C.sub.1-4 -alkyl, in particular 
aminomethyl, C.sub.1-6 -alkylamino-C.sub.1-4 -alkyl, in particular 
methylaminomethyl, C.sub.1-6 -dialkylamino-C.sub.1-4 -alkyl, in 
particular, dimethylaminomethyl, C.sub.3-6 -cycloalkylamino-C.sub.1-2 
-alkyl, in particular morpholinomethyl, thiomorpholinomethyl, C.sub.3-6 
-cycloalkyl, in particular cyclopropyl, cyclobutyl, C.sub.1-4 
-alkoxycarbonyl, in particular methoxycarbonyl, ethoxycarbonyl, 
R.sup.4 represents hydrogen, straight-chain or branched C.sub.1-6 -alkyl, 
in particular methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, 
tert-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 
1,2-di-methylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 
1-ethyl-propyl, hexyl, 1-methylpentyl, halogeno-C.sub.1-6 -alkyl, in 
particular fluoromethyl, difluoromethyl, difluorochloromethyl, 
trifluoromethyl, trichloromethyl, 1-fluoroethyl, trifluoroethyl, 
2-chloro-1,1,2-trifluoroethyl, hydroxy-C.sub.1-6 -alkyl, in particular 
hydroxymethyl, hydroxyethyl, 2-hydroxypropyl, C.sub.1-4 
-alkanoyloxy-C.sub.1-4 -alkyl, in particular acetoxymethyl, acetoxyethyl, 
2-acetoxypropyl, C.sub.1-2 -alkoxy-C.sub.1-4 -alkyl, in particular 
methoxymethyl, methoxyethyl, 2-methoxypropyl, C.sub.1-4 
-alkoxycarbonyl-C.sub.1-4 -alkyl, in particular methoxycarbonylmethyl, 
ethoxycarbonylmethyl, tert-butoxy-carbonylmethyl, methoxycarbonylethyl, 
ethoxycarbonylethyl, amino-C.sub.1-6 -alkyl, in particular aminomethyl, 
aminoethyl, 2-aminopropyl, C.sub.1-6 -alkylamino-C.sub.1-6 alkyl, in 
particular methylaminomethyl, methylaminoethyl, C.sub.1-6 
-dialkylamino-C.sub.1-6 -alkyl, in particular di-methylaminomethyl, 
dimethylaminoethyl, C.sub.1-6 -trialkylammonium-C.sub.1-6 -alkyl halide, 
in particular trimethylaminomethylene iodide, tri-methylaminoethylene 
iodide, C.sub.3-7 -cycloalkylamino-C.sub.1-4 -alkyl, in particular 
N-pyrrolidinoethyl, N-morpholinoethyl, N-piperidino-ethyl, 
N-thiomorpholinoethyl, N.sup.1 -(N.sup.4 -methylpiperazino)-ethyl, 
C.sub.2-6 -alkenyl, in particular vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 
1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 1-methyl-2-butenyl, 
2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 
1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 
2-hexenyl, 1,1-dimethyl-2-butenyl, 1,2-dimethyl-2-butenyl, 
1-ethyl-2-butenyl, C.sub.2-6 -alkinyl, in particular ethinyl, 2-propinyl, 
2-butinyl, 3-butinyl, 1-methyl-2-propinyl, 2-pentinyl, 1-methyl-3-butinyl, 
2-methyl-3-butinyl, 1,1-dimethyl-2-propinyl, 1-ethyl-2-propinyl, C.sub.3-6 
-cycloalkyl in particular cyclopropyl, cyclobutyl, cyclopentyl, 
cyclohexyl, C.sub.3-6 -cycloalkyl-C.sub.1-2 -alkyl, in particular 
cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 
aryl, in particular phenyl, aryl-C.sub.1-2 -alkyl, in particular 
phenylmethyl, 1-phenylethyl, 2-phenylethyl, heteroaryl, in particular 
pyridyl or thiazolyl, N-morpholinyl, heteroaryl-C.sub.1-2 -alkyl, in 
particular pyridylmethyl and thiazolylmethyl, which radicals can 
optionally be substituted by radicals from the series consisting of 
halogen, in particular fluorine, chlorine, bromine or iodine, C.sub.1-4 
-alkyl, in particular methyl, C.sub.1-4 -halogenoalkyl, in particular 
trifluoromethyl, trichloromethyl, amino, hydroxyl, C.sub.1-4 -alkoxy, in 
particular methoxy, C.sub.1-2 -alkylenedioxy, in particular methylenedioxy 
or ethylenedioxy, C.sub.1-4 -halogenoalkoxy, in particular 
trifluoromethoxy, difluoromethoxy, C.sub.1-4 -alkylthio, in particular 
methylthio, C.sub.1-4 -halogenoalkylthio, in particular 
trifluoromethylthio, C.sub.1-4 -alkylsulfonyl in particular 
methylsulfonyl, C.sub.1-4 -alkylamino, in particular methylamino, 
di-C.sub.1-4 -alkylamino, in particular dimethyl-amino, C.sub.1-4 
-alkylcarbonyl, in particular methylcarbonyl, C.sub.1-4 -alkoxycarbonyl, 
in particular methoxycarbonyl, 
R.sup.5 for hydrogen, straight-chain or branched C.sub.1-6 -alkyl, in 
particular methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, 
tert-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 
1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 
hexyl, 1-methylpentyl, halogeno-C.sub.1-6 -alkyl, in particular 
fluoromethyl, difluoromethyl, difluorochloromethyl, trifluoromethyl, 
trichloromethyl, 1-fluoroethyl, trifluoroethyl, 
2-chloro-1,1,2-trifluoroethyl, hydroxy-C.sub.1-6 -alkyl, in particular 
hydroxymethyl, hydroxyethyl, 2-hydroxypropyl, C.sub.1-4 
-alkanoyloxy-C.sub.1-4 -alkyl, in particular acetoxymethyl, acetoxyethyl, 
2-acetoxypropyl, C.sub.1-2 -alkoxy-C.sub.1-4 -alkyl, in particular 
methoxymethyl, methoxyethyl, 2-methoxypropyl, amino-C.sub.1-6 -alkyl, in 
particular aminomethyl, aminoethyl, 2-aminopropyl, C.sub.1-6 
-alkylamino-C.sub.1-6 -alkyl, in particular methylaminomethyl, 
methylaminoethyl, C.sub.1-6 -dialkylamino-C.sub.1-6 -alkyl, in particular 
dimethylaminomethyl, dimethylaminoethyl, C.sub.1-6 
-trialkylammonium-C.sub.1-6 -alkyl halide, in particular 
trimethyl-ammoniummethylene or trimethylammoniumethylene iodide, C.sub.3-7 
-cycloalkylamino-C.sub.1-4 -alkyl, in particular N-pyrrolidinoethyl, 
N-morpholinoethyl, N-piperidinoethyl, N-thiomorpholinoethyl, N.sup.1 
-(N.sup.4 -methylpiperazino)-ethyl, nitro-C.sub.1-4 -alkyl, in particular 
nitromethyl, 2-nitroethyl, 2-nitropropyl, cyano-C.sub.1-4 -alkyl, in 
particular cyanomethyl, 2-cyanoethyl, 2-cyanopropyl, C.sub.1-4 
-alkoxycarbonyl-C.sub.1-4 -alkyl, in particular methoxycarbonylmethyl, 
2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, carbamoyl-C.sub.1-4 -alkyl, 
in particular carbamoylethyl, carboxyl-C.sub.1-4 -alkyl, in particular 
2-carboxylethyl, C.sub.2-6 -alkenyl, in particular vinyl, 2-propenyl, 
2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 
2-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 
1-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 
1-ethyl-2-propenyl, 2-hexenyl, 1,1-dimethyl-2-butenyl, 
1,2-dimethyl-2-butenyl, 1-ethyl-2-butenyl, C.sub.2-6 -alkinyl, in 
particular ethinyl, 2-propinyl, 2-butinyl, 3-butinyl, 1-methyl-2-propinyl, 
2-pentinyl, 1-methyl-3-butinyl, 2-methyl-3-butinyl, 
1,1-dimethyl-2-propinyl, 1-ethyl-2-propinyl, C.sub.3-6 -cycloalkyl, in 
particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, C.sub.3-6 
-cycloalkyl-C.sub.1-2 -alkyl, in particular cyclopropylmethyl, 
cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, C.sub.1-4 
-alkoxydicarbonyl, in particular methoxydicarbonyl or ethoxydicarbonyl, 
aryl-C.sub.1-2 -alkyl, in particular phenylmethyl, heteroaryl, in 
particular pyridyl, pyrimidyl, pyrazinyl or thiazolyl, 
heteroaryl-C.sub.1-2 -alkyl, in particular pyridylmethyl and 
thiazolylmethyl, which radicals can optionally be substituted by radicals 
from the series consisting of halogen, in particular fluorine, chlorine, 
bromine or iodine, C.sub.1-4 -alkyl, in particular methyl, C.sub.1-4 
-halogenoalkyl, in particular trifluoromethyl, trichloromethyl, amino, 
hydroxyl, C.sub.1-4 -alkoxy, in particular methoxy, C.sub.1-2 
-alkylenedioxy, in particular methylenedioxy or ethylenedioxy, C.sub.1-4 
-halogenoalkoxy, in particular trifluoromethoxy, difluoromethoxy, 
C.sub.1-4 -alkylthio, in particular methylthio, C.sub.1-4 
-halogenoalkylthio, in particular trifluoromethylthio, C.sub.1-4 
-alkylsulfonyl in particular methylsulfonyl C.sub.1-4 -alkylamino, in 
particular methylamino, di-C.sub.1-4 -alkylamino, in particular 
dimethylamino, C.sub.1-4 -alkylcarbonyl, in particular methylcarbonyl, 
C.sub.1-4 -alkoxycarbonyl, in particular methoxycarbonyl, methoxycarbonyl, 
can be substituted, or for a radical from the group consisting of G.sup.1, 
G.sup.2, G.sup.3 and G.sup.4 
##STR37## 
in which R.sup.6 represent hydrogen, straight-chain or branched C.sub.1-6 
-alkyl, in particular methyl, ethyl, propyl, isopropyl, isobutyl, 
sec-butyl, tert-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 
3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 
1-ethylpropyl, hexyl, 1-methylpentyl, C.sub.3-6 -cycloalkyl, in particular 
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, aryl-C.sub.1-2 -alkyl, 
in particular phenylmethyl, heteroaryl-C.sub.1-2 -alkyl, in particular 
pyridylmethyl and thiazolylmethyl, which are optionally substituted, 
R.sup.6 and R.sup.7, together with the atoms to which they are bonded, 
represent a 5- or 6-membered ring, which optionally sulfur, can be 
interrupted and is optionally substituted by hydroxyl, stand, 
R.sup.7 represents hydrogen, straight-chain or branched alkyl having up to 
6 carbon atoms, in particular methyl, ethyl, propyl, isopropyl, sec-butyl, 
tert-butyl, hydroxy-C.sub.1-2 -alkyl, in particular hydroxymethyl, 
1-hydroxyethyl, C-.sub.1-4 -alkanoyloxy-C.sub.1-4 -alkyl, in particular 
acetoxy-methyl, 1-acetoxymethyl, C.sub.1-4 -alkoxy-C.sub.1-4 -alkyl, in 
particular methoxymethyl, 1-methoxyethyl, aryl-C.sub.1-4 -alkoxy-C.sub.1-4 
-alkyl, in particular benzyloxymethyl, 1-benzyloxymethyl, 
mercapto-C.sub.1-4 -alkyl, in particular mercaptomethyl, C.sub.1-4 
-alkylthio-C.sub.1-4 -alkyl, in particular methylsulfinylmethyl, C.sub.1-4 
-alkylsulfonyl-C.sub.1-4 -alkyl, in particular methylsulfonylethyl, 
carboxy-C.sub.1-4 -alkyl, in particular carboxymethyl, carboxyethyl, 
C.sub.1-4 alkoxycarbonyl-C.sub.1-4 -alkyl, in particular 
methoxycarbonylmethyl, ethoxycarbonylmethyl, aryl-C.sub.1-4 
-alkoxycarbonyl-C.sub.1-4 -alkyl, in particular benzyloxycarbonylmethyl, 
carbamoyl-C.sub.1-4 -alkyl, in particular carbamoylmethyl, carbamoylethyl, 
amino-C.sub.1-4 -alkyl, in particular aminopropyl, aminobutyl, C.sub.1-4 
-alkylamino-C.sub.1-4 -alkyl, in particular methylaminopropyl, 
methylaminobutyl, C.sub.1-4 -dialkylamino-C.sub.1-4 -alkyl, in particular 
dimethylaminopropyl, dimethylaminobutyl, guanido-C.sub.1-4 -alkyl, in 
particular guanidopropyl, C.sub.1-4 -alkoxy-carbonylamino-C.sub.1-4 
-alkyl, in particular tert-butylcarbonylamino-propyl, 
tert-butylcarbonylaminobutyl, alkenyl having up to 6 carbon atoms, in 
particular vinyl, 2-propenyl, 2-butenyl, 1-methyl-2-propenyl, C.sub.3-6 
-cycloalkyl-C.sub.1-2 -alkyl, in particular cyclopropylmethyl, 
cyclobutylmethyl, cyclohexylmethyl, hetaryl-C.sub.1-2 -alkyl, in 
particular benzo[b]thien-1-yl-methyl, benzo[b]thien-3-yl, 
pyrid-2-yl-methyl, pyrid-3-yl-methyl, pyrid-4-yl-methyl, fur-2-yl-methyl, 
fur-3-yl-methyl, thien-2-yl-methyl, thien-3-yl-methyl, indol-3-yl-methyl, 
N-methyl-indol-3-yl-methyl, imidazol-4-yl-methyl, 
N-methylimidazol-4-yl-methyl, aryl-C.sub.1-2 -alkyl, in particular benzyl, 
which radicals can optionally be substituted by radicals from the series 
consisting of halogen, in particular fluorine, chlorine, bromine or 
iodine, hydroxyl, C.sub.1-4 -alkyl, in particular methyl or tert-butyl, 
C.sub.1-4 -halo-genoalkyl, in particular trifluoromethylethyl, 
difluoromethyl or trichloromethyl, C.sub.1-4 -alkoxy, in particular 
methoxy, ethoxy or tert-butyloxy, C.sub.1-4 -halogenoalkoxy, in particular 
trifluoromethoxy, difluoromethoxy, C.sub.1-4 -alkylthio, in particular 
methylthio, C.sub.1-4 -halogenoalkylthio, in particular 
trifluoromethylthio, C.sub.1-2 -alkylenedioxy, in particular 
methylenedioxy or ethylenedioxy, nitro, amino, C.sub.1-4 -alkylamino, in 
particular methylamino, C.sub.1-4 -di-alkylamino, in particular 
dimethylamino, C.sub.3-6 -cycloalkylamino, in particular pyrrolidino, 
piperidino, C.sub.3-6 -cycloalkylthioamino, in particular thiomorpholino 
and dioxothiomorpholino, C.sub.3-6 -cycloalkyldiamino, in particular 
N-methylpiperazino, and 
R.sup.8 represents hydrogen or methyl, 
##STR38## 
represents carboxyl, thiocarboxyl, --C.dbd.CH--NO.sub.2, --C.dbd.CH--CN, 
--C.dbd.N--R.sup.9, sulfoxyl, sulfonyl, --P(O)--OR.sup.10 or 
P(S)--OR--.sup.10, 
R.sup.9 represents hydrogen, hydroxyl, C.sub.1-4 -alkoxy, in particular 
methoxy, ethoxy, sec-butyloxy, C.sub.1-4 -alkylcarbonyl, in particular 
methylcarbonyl, ethylcarbonyl, C.sub.1-4 -halogenoalkylcarbonyl, in 
particular trifluoromethylcarbonyl, trichloromethylcarbonyl, C.sub.1-4 
-alkylsulfonyl, in particular methylsulfonyl, ethylsulfonyl, 
propylsulfonyl, nitro or cyano, and 
R.sup.10 represents hydrogen or C.sub.1-4 -alkyl, in particular methyl or 
ethyl, and 
Q represents straight-chain or branched C.sub.1-4 -alkyl, in particular 
methyl, ethyl, propyl, isopropyl, sec-butyl, tert-butyl, C.sub.1-4 
-halogenoalkyl, in particular trifluoromethyl, trichloromethyl, 
chlorodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, chloromethyl, 
bromomethyl, 1-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 
C.sub.2-6 -alkenyl, in particular vinyl, 2-propenyl, 1-methyl-2-propenyl 
and 2-butenyl, C.sub.2-6 -halogenoalkenyl, in particular difluorovinyl, 
dichlorovinyl, 2-chloro-2-propenyl, 2,3,3-trifluoro-2-propenyl, 
2,3,3-trichloro-2-propenyl, 4,4-difluoro-3-butenyl, C.sub.3-6 -cycloalkyl, 
in particular cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, 
hetaryl-C.sub.1-2 -alkyl, in particular pyridylmethyl and thiazolylmethyl, 
which radicals can optionally be substituted by radicals from the series 
consisting of halogen, in particular fluorine, chlorine, bromine or 
iodine, hydroxyl, C.sub.1-4 -alkyl, in particular methyl or tert-butyl 
C.sub.1-4 -halogenoalkyl, in particular trifluoromethyl, difluoromethyl or 
trichloromethyl, C.sub.1-4 -alkoxy, in particular methoxy, C.sub.1-4 
-halogenoalkoxy, in particular trifluoromethoxy, difluoromethoxy, 
C.sub.1-4 -alkylthio, in particular methylthio, C.sub.1-4 
-halogenoalkylthio, in particular trifluoromethylthio, nitro, amino, 
C.sub.1-4 -alkylamino, in particular methylamino, C.sub.1-4 -dialkylamino, 
in particular dimethylamino, or optionally represents a radical from the 
group consisting of G.sup.5 and G.sup.6 
##STR39## 
in which 
##STR40## 
can denote carboxyl, thiocarboxyl or sulfonyl, Y represents oxygen, 
sulfur or --NR.sup.12, 
R.sup.11, in the case where Y represents nitrogen, a cyclic amino group 
linked via a nitrogen atom, in particular 1-azetidinyl, pyrrolidino, 
2-pyrrolin-1-yl, 1-pyrrolyl, piperidino, 1,4-dihydropyridin-1-yl, 
1-imidazolidinyl, 1-imidazolyl, 1-pyrazolyl, 1-triazolyl, 1-tetrazolyl, 
1-piperazinyl, 1-homopiperazinyl, 1,2-dihydro-pyridazin-1-yl, 
1,2-dihydropyrimidin-1-yl, perhydropyrimidin-1-yl, 
1,4-diazacyclo-heptan-1-yl, thiazolidin-3-yl, isothiazolin-2-yl, 
morpholino, thiomorpholino, dioxothiomorpholino, which radicals can 
optionally be substituted by radicals from the series consisting of 
halogen, in particular fluorine, chlorine, bromine or iodine, C.sub.1-4 
-alkyl, in particular methyl, hydroxy-C.sub.1-4 -alkyl, in particular 
hydroxymethyl, amino-C.sub.1-4 -alkyl, in particular aminomethyl, 
aminoethyl, C.sub.1-4 -monoalkylamino-C.sub.1-4 -alkyl, in particular 
methylaminomethyl, methylaminoethyl, C.sub.1-4 -dialkylamino-C.sub.1-4 
-alkyl, in particular dimethylaminomethyl, dimethylaminoethyl, amino, 
hydroxyl, C.sub.1-4 -alkoxy, in particular methoxy, C.sub.1-4 
-alkylcarbonyl, in particular methylcarbonyl, C.sub.1-4 -alkoxycarbonyl, 
in particular methoxycarbonyl, 
R.sup.11 and R.sup.12 independently of one another represent hydrogen, 
straight-chain or branched C.sub.1-4 -alkyl, in particular methyl, ethyl, 
propyl, isopropyl, sec-butyl, tert-butyl, carboxyl-C.sub.1-4 -alkyl, in 
particular carboxylmethyl, C.sub.2-4 -alkenyl, in particular vinyl, 
2-propenyl, 1-methyl-2-propenyl and 2-butenyl, C.sub.2-4 -alkinyl, in 
particular ethinyl, 2-propinyl and 2-butinyl, C.sub.3-6 -cycloalkyl, in 
particular cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, C.sub.3-6 
-cycloalkyl-C.sub.1-2 -alkyl, in particular cyclopropylmethyl, 
cyclobutylmethyl, cyclopentylmethyl and cyclohexylmethyl, hetaryl, in 
particular pyridyl and thiazolyl, hetaryl-C.sub.1-2 -alkyl, in particular 
pyridylmethyl and thiazolylmethyl, which radicals can be optionally 
substituted by radicals from the series consisting of halogen, in 
particular fluorine, chlorine, bromine or iodine, C.sub.1-4 -alkyl, in 
particular methyl, hydroxy-C.sub.1-4 -alkyl, in particular hydroxymethyl, 
amino-C.sub.1-4 -alkyl, in particular aminomethyl, aminoethyl, C.sub.1-4 
-monoalkylamino-C.sub.1-4 -alkyl, in particular methylaminomethyl, 
methylaminoethyl, C.sub.1-4 -dialkylaminoC.sub.1-4 -alkyl, in particular 
dimethylaminomethyl, dime-thylaminoethyl, amino, hydroxyl, C.sub.1-4 
-alkoxy, in particular methoxy, C.sub.1-4 -alkylcarbonyl, in particular 
methylcarbonyl, C.sub.1-4 -alkoxycarbonyl, in particular methoxycarbonyl, 
or 
R.sup.11 and R.sup.12, together with the adjacent N atom, represent a 
carbocyclic 5-, 6- or 7-membered ring system, or represent a 7 to 
10-membered bicyclic ring system, which can optionally also be interrupted 
by oxygen, sulfur, sulfoxyl, sulfonyl, carbonyl, --N--O, --N.dbd., 
--NR.sup.14 -- or by quaternized nitrogen and is optionally substituted by 
C.sub.1-4 -alkyl, in particular methyl, hydroxy-C.sub.1-4 -alkyl, in 
particular hydroxymethyl, amino-C.sub.1-4 -alkyl, in particular 
aminomethyl, aminoethyl, C.sub.1-4 -monoalkylamino-C.sub.1-4 -alkyl, in 
particular methylaminomethyl, methylaminoethyl, C.sub.1-4 
-dialkylamino-C.sub.1-4 -alkyl, in particular dimethylaminomethyl, 
dimethylaminoethyl, amino, hydroxyl, C.sub.1-4 -alkoxy, in particular 
methoxy, C.sub.1-4 -alkylcarbonyl, in particular methylcarbonyl, C.sub.1-4 
-alkoxycarbonyl, in particular methoxycarbonyl, halogen, in particular 
fluorine, chlorine, bromine or iodine, or a radical from the groups 
G.sup.7, G.sup.8, G.sup.9, G.sup.10 and G.sup.11 
##STR41## 
in which n can denote the numbers 0, 1, 2, 3 or 4, 
R.sup.13 represents hydrogen or C.sub.1-4 -alkyl, in particular methyl, 
ethyl, propyl, isopropyl, sec-butyl, tert-butyl, and 
R.sup.14 represents hydrogen, straight-chain or branched C.sub.1-6 -alkyl, 
in particular methyl, ethyl, propyl, isopropyl, sec-butyl, tert-butyl, 
C.sub.2 6 -alkenyl, in particular vinyl, 2-propenyl, 1-methyl-2-propenyl 
and 2-butenyl, C.sub.2-6 -alkinyl, in particular ethinyl, 2-propinyl and 
2-butinyl, C.sub.3-6 -cycloalkyl, in particular cyclopropyl, cyclobutyl, 
cyclopentyl and cyclohexyl, C.sub.3-6 -cycloalkyl-C.sub.1-2 -alkyl, in 
particular cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl and 
cyclohexylmethyl, C.sub.1-4 -alkylcarbonyl, in particular methylcarbonyl, 
ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, 
isobutylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl, C.sub.3-6 
-cycloalkylcarbonyl, in particular cyclopropylcarbonyl, 
cyclobutylcarbonyl, cyclopentylcarbonyl and cyclohexylcarbonyl, C.sub.1-4 
-alkoxycarbonyl, in particular methoxycarbonyl, ethoxycarbonyl, 
n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, 
isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, 
hydroxy-C.sub.1-4 -alkyl, in particular hydroxymethyl, hydroxyethyl, 
hydroxyethylsulfonylethyl, C.sub.1-4 -alkylamino, in particular 
methylamino, ethylamino, C.sub.1-4 -monoalkylamino-C.sub.1-4 -alkyl, in 
particular methylaminomethyl, methylaminoethyl, C.sub.1-4 
-dialkylamino-C.sub.1-4 -alkyl, in particular dimethylaminomethyl, 
dimethylaminoethyl, dimethylaminopropyl, C.sub.3-7 
-cycloalkylamino-C.sub.1-4 -alkyl, in particular N-pyrrolidinoethyl, 
N-morpholinoethyl, N-piperidinoethyl, N-thio-morpholinoethyl, N.sup.1 
-(N.sup.4 -methyl-piperazino)-ethyl, C.sub.3-6 
-cycloalkyl-aminocarbonyl-C.sub.1-2 -alkyl, in particular 
N-morpholinocarbonyl-methyl, cyano, aryl, in particular phenyl, 
aryl-C.sub.1-2 -alkyl, in particular phenylmethyl, hetaryl, in particular 
pyridyl or thiazolyl, heteroaryl-C.sub.1-2 -alkyl, in particular 
pyridylmethyl and thiazolyl-methyl, which radicals can optionally be 
substituted by radicals from the series consisting of halogen, in 
particular fluorine, chlorine, bromine or iodine, C.sub.1-4 -alkyl, in 
particular methyl, C.sub.1-4 -halogenoalkyl, in particular 
trifluoromethyl, trichloromethyl, amino, hydroxyl, C.sub.1-4 -alkoxy, in 
particular methoxy, C.sub.1-2 -alkylenedioxy, in particular methylenedioxy 
or ethylenedioxy, C.sub.1-4 -halogenoalkoxy, in particular 
trifluoromethoxy, difluoromethoxy, C.sub.1-4 -alkylthio, in particular 
methylthio, C.sub.1-4 -halogenoalkylthio, in particular 
trifluoromethylthio, C.sub.1-4 -alkylsulfonyl in particular 
methylsulfonyl, C.sub.1-4 -alkylamino, in particular methylamino, 
di-C.sub.1-4 -alkylamino, in particular dimethylamino, C.sub.1-4 
-alkylcarbonyl, in particular methylcarbonyl, C.sub.1-4 -alkoxycarbonyl, 
in particular methoxycarbonyl, 
with the proviso for the compounds of the general formula (Ia), in the case 
where 
R.sup.1 represents hydrogen, 
R.sup.2 and R.sup.3 represent methyl, 
R.sup.4 represents radicals other than methyl, n-butyl, phenyl, 2-, 3- or 
4-methylphenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-fluorophenyl, 
2-chloro, 4-fluorophenyl, 2-fluoro, 4-chlorophenyl, 3-chloro, 
4-fluorophenyl, 2-, 3- or 4-nitrophenyl, 4-methoxyphenyl, 
and optical isomers and racemates thereof. 
Particularly preferred compounds are those of the formula (I) and salts 
thereof 
##STR42## 
in which R.sup.1 represent hydrogen, straight-chain or branched C.sub.1-4 
-alkyl, in particular methyl, ethyl, propyl, isopropyl, isobutyl, 
sec-butyl, C.sub.3-6 -cycloalkyl, in particular cyclopropyl, 
R.sup.2 represents hydrogen, straight-chain or branched branched C.sub.1-4 
-alkyl, in particular methyl, ethyl, propyl, isopropyl, isobutyl, 
sec-butyl, tert-butyl, halogeno-C.sub.1-4 -alkyl, in particular 
chloromethyl, bromomethyl, hydroxy-C.sub.1-4 -alkyl, in particular 
hydroxymethyl, C.sub.1-4 -alkanoyloxy-C.sub.1-4 -alkyl, in particular 
acetoxymethyl, C.sub.1-2 -alkoxyalkyl, in particular methoxymethyl, 
C.sub.1-2 -alkylthioalkyl, in particular methyl-thiomethyl, C.sub.1-2 
-alkylsulfinyl-C.sub.1-4 -alkyl, in particular methyl-sulfinylmethyl, 
C.sub.1-2 -alkylsulfonyl-C.sub.1-4 -alkyl, in particular 
methyl-sulfonylmethyl, C.sub.1-6 -alkylamino-C.sub.1-4 -alkyl, in 
particular methyl-aminomethyl, C.sub.1-6 -dialkylamino-C.sub.1-4 -alkyl, 
in particular dimethylaminomethyl, C.sub.3-6 -cycloalkylamino-C.sub.1-2 
-alkyl, in particular morpholinomethyl, thiomorpholinomethyl, C.sub.1-4 
-alkoxycarbonyl, in particular methoxycarbonyl, ethoxycarbonyl, 
R.sup.3 represents hydrogen, straight-chain or branched branched C.sub.1-4 
-alkyl, in particular methyl, ethyl, propyl, isopropyl, isobutyl, 
sec-butyl, tert-butyl, 
R.sup.4 represents straight-chain or branched C.sub.1-6 -alkyl, in 
particular methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, 
tert-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 
1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 
hexyl, 1-methylpentyl, halogeno-C.sub.1-6 -alkyl, in particular 
fluoromethyl, difluoromethyl, fluoroethyl, C.sub.1-4 
-alkoxycarbonyl-C.sub.1-4 -alkyl, in particular methoxycarbonylmethyl, 
ethoxycarbonylmethyl, tert-butoxycarbonylmethyl, C.sub.3-7 
-cycloalkylamino-C.sub.1-4 -alkyl, in particular N-pyrrolidinoethyl, 
N-morpholinoethyl, N-piperidinoethyl, N-thiomorpholinoethyl, C.sub.2-6 
-alkenyl, in particular 2-propenyl, 2-butenyl, C.sub.3-6 -cycloalkyl in 
particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, C.sub.3-6 
-cycloalkyl-C.sub.1-2 -alkyl, in particular cyclopropylmethyl, 
cyclobutylmethyl, aryl-C.sub.1-2 -alkyl, in particular phenylmethyl, 
1-phenylethyl, 2-phenylethyl, heteroaryl, in particular pyridyl or 
thiazolyl, N-morpholinyl, hetaryl-C.sub.1-2 -alkyl, in particular 
pyridylmethyl and thiazolylmethyl, which radicals can optionally be 
substituted by radicals from the series consisting of halogen, in 
particular fluorine, chlorine, bromine or iodine, C.sub.1-4 -alkyl, in 
particular methyl, C.sub.1-4 -halogenoalkyl, in particular 
trifluoromethyl, trichloromethyl, amino, hydroxyl, C.sub.1-4 -alkoxy, in 
particular methoxy, C.sub.1-2 -alkylenedioxy, in particular methylenedioxy 
or ethylenedioxy, C.sub.1-4 -halogenoalkoxy, in particular 
trifluoromethoxy, difluoromethoxy, C.sub.1-4 -alkylthio, in particular 
methylthio, C.sub.1-4 -halogenoalkylthio, in particular 
trifluoromethylthio, C.sub.1-4 -alkylsulfonyl in particular 
methylsulfonyl, C.sub.1-4 -alkylamino, in particular methylamino, 
di-C.sub.1-4 -alkylamino, in particular dimethylamino, C.sub.1-4 
-alkylcarbonyl, in particular methylcarbonyl, C.sub.1-4 -alkoxycarbonyl, 
in particular methoxycarbonyl, 
R.sup.5 for hydrogen, straight-chain or branched C.sub.1-6 -alkyl, in 
particular methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, 
C.sub.1-4 -alkanoyloxy-C.sub.1-4 -alkyl, in particular 
methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, 
ethoxycarbonylethyl, tert-butoxycarbonylmethyl, amino-C.sub.1-6 -alkyl, in 
particular amino- methyl, aminoethyl, C.sub.1-6 -alkylamino-C.sub.1-6 
-alkyl, in particular methyl aminomethyl, methyl aminomethyl, C.sub.1-6 
-dialkylamino-C.sub.1-6 -alkyl, in particular dimethylaminomethyl, 
dimethylaminoethyl, C.sub.1-6 -trialkylammonium-C.sub.1-6 -alkyl halide, 
in particular trimethylammoniummethylene or trimethylammoniu-methylene 
iodide, C.sub.3-7 -cycloalkylamino-C.sub.1-4 -alkyl, in particular 
N-pyrrolidinoethyl, N-morpholinoethyl, N-piperidinoethyl, 
N-thiomorpholinoethyl, N.sup.1 -(N.sup.4 -methyl-piperazino)-ethyl, 
nitro-C.sub.1-4 -alkyl, 2-nitroethyl, cyano-C.sub.1-4 -alkyl, in 
particular 2-cyanoethyl, C.sub.1-4 -alkoxycarbonyl-C.sub.1-4 -alkyl, in 
particular 2-methoxycarbonylethyl, C.sub.2-6 -alkenyl, in particular 
2-propenyl, C.sub.2-6 -alkinyl, in particular 2-propinyl, C.sub.1-4 
-alkoxydicarbonyl, in particular methoxydicarbonyl or ethoxydicarbonyl, 
heteroaryl, in particular pyridyl, pyrimidyl, pyrazinyl or thiazolyl, 
heteroaryl-C.sub.1-2 -alkyl, in particular pyridyl, pyrimidyl, pyrazinyl 
or thiazolyl, heteroaryl-C.sub.1-2 -alkyl, in particular pyridylmethyl and 
thiazolylmethyl, which radicals can optionally be substituted by radicals 
from the series consisting of halogen, in particular fluorine, chlorine, 
bromine or iodine, C.sub.1-4 -alkyl, in particular methyl, C.sub.1-4 
-halogenoalkyl, in particular trifluoromethyl, trichloromethyl, amino, 
hydroxyl, C.sub.1-4 -alkoxy, in particular methoxy, C.sub.1-2 
-alkylenedioxy, in particular methylenedioxy or ethylenedioxy, C.sub.1-4 
-halogenoalkoxy, in particular trifluoromethoxy, difluoromethoxy, 
C.sub.1-4 -alkylthio, in particular methylthio, C.sub.1-4 
-halogenoalkylthio, in particular trifluoromethylthio, C.sub.1-4 
-alkylsulfonyl, in particular methylsulfonyl, C.sub.1-4 -alkylamino, in 
particular methylamino, di-C.sub.1-4 -alkylamino, in particular 
dimethylamino, C.sub.1-4 -alkylcarbonyl, in particular methylcarbonyl, 
C.sub.1-4 -alkoxycarbonyl, in particular methoxycarbonyl, methoxycarbonyl, 
can be substituted 
or for a radical from the group consisting of G.sup.1, G.sup.2, G.sup.3 and 
G.sup.4 
##STR43## 
in which R.sup.6 represents hydrogen, straight-chain or branched C.sub.1-6 
-alkyl, in particular methyl, ethyl, C.sub.3-6 -cycloalkyl, in particular 
cyclopropyl, 
R.sup.6 and R.sup.7, together with the atoms to which they are bonded, 
represent a 5- or 6-membered ring, which optionally sulfur, can be 
interrupted and is optionally substituted by hydroxyl, stand, 
R.sup.7 for hydrogen, straight-chain or branched alkyl having up to 6 
carbon atoms, in particular methyl, ethyl, propyl, isopropyl, sec-butyl, 
R.sup.8 represents hydrogen or methyl, 
##STR44## 
represents carboxyl, --C.dbd.CH--NO.sub.2, --C.dbd.CH--CN, 
--C.dbd.N--R.sup.9, sulfonyl, 
R.sup.9 represents C.sub.1-4 -halogenoalkylcarbonyl, in particular 
trifluoromethylcarbonyl, trichloromethylcarbonyl, C.sub.1-4 
-alkylsulfonyl, in particular methylsulfonyl, ethylsulfonyl, nitro or 
cyano, and 
Q represents a radical from the group consisting of G.sup.5 and G.sup.6 
##STR45## 
in which 
##STR46## 
can denote carboxyl or sulfonyl, Y represents oxygen or --NR.sup.12, 
R.sup.11, in the case where Y represents nitrogen, a cyclic amino group 
which is linked via a nitrogen atom, in particular pyrrolidino, 
2-pyrrolin-1-yl, 1-pyrrolyl, piperidino, 1,4-dihydropyridin-1-yl, 
1-piperazinyl, 1-homopiperazinyl, morpholino, thiomorpholino, 
dioxothio-morpholino, which radicals can optionally be substituted by 
radicals from the series consisting of halogen, in particular fluorine, 
chlorine, bromine or iodine, C.sub.1-4 -alkyl, in particular methyl, 
hydroxy-C.sub.1-4 -alkyl, in particular hydroxymethyl, amino-C.sub.1-4 
-alkyl, in particular aminomethyl, aminoethyl, C.sub.1-4 -monoalkylamino 
C.sub.1-4 -alkyl, in particular methylaminomethyl, methylaminoethyl, 
C.sub.1-4 -di-alkyl-amino-C.sub.1-4 -alkyl, in particular 
dimethylaminomethyl, dimethylaminoethyl, amino, hydroxyl, C.sub.1-4 
-alkoxy, in particular methoxy, C.sub.1-4 -alkylcarbonyl, in particular 
methylcarbonyl, C.sub.1-4 -alkoxycarbonyl, in particular methoxycarbonyl, 
R.sup.11 and R.sup.12 independently of one another represent hydrogen, 
straight-chain or branched C.sub.1-4 -alkyl, in particular methyl, ethyl, 
propyl, isopropyl, sec-butyl, carboxyl-C.sub.1-4 -alkyl, in particular 
carboxylmethyl, C.sub.2-4 -alkenyl, in particular vinyl, 2-propenyl, 
1-methyl-2-propenyl, C.sub.2-4 -alkinyl, in particular ethinyl, 
2-propinyl, C.sub.3-6 -cycloalkyl, in particular cyclopropyl, 
heteroaryl-C.sub.1-2 -alkyl, in particular pyridylmethyl and 
thiazolylmethyl, which radicals can optionally be substituted by radicals 
from the series consisting of halogen, in particular fluorine, chlorine, 
bromine or iodine, C.sub.1-4 -alkyl, in particular methyl, 
hydroxy-C.sub.1-4 -alkyl, in particular hydroxymethyl, amino-C.sub.1-4 
-alkyl, in particular aminomethyl, aminoethyl, C.sub.1-4 
-monoalkylamino-C.sub.1-4 alkyl, in particular methylaminomethyl, 
methylaminoethyl, C.sub.1-4 -dialkylaminoC.sub.1-4 -alkyl, in particular 
dimethylaminomethyl, dimethylaminoethyl, amino, hydroxyl, C.sub.1-4 
-alkoxy, in particular methoxy, C.sub.1-4 -alkylcarbonyl, in particular 
methylcarbonyl, C.sub.1-4 -alkoxycarbonyl, in particular methoxycarbonyl, 
or 
R.sup.11 and R.sup.12, together with the adjacent N atom, represent a 
carbocyclic 5-, 6- or 7-membered ring system, or represent a 7 to 
10-membered bicyclic ring system, which can optionally also be interrupted 
by oxygen, sulfur, sulfoxyl, sulfonyl, carbonyl, --N--O, --N.dbd., 
--NR.sup.14 -- or by quaternized nitrogen and is optionally substituted by 
C.sub.1-4 -alkyl, in particular methyl, hydroxy-C.sub.1-4 -alkyl, in 
particular hydroxymethyl, amino-C.sub.1-4 -alkyl, in particular 
aminomethyl, aminoethyl, C.sub.1-4 -monoalkylamino-C.sub.1-4 -alkyl, in 
particular methylaminomethyl, methylaminoethyl, C.sub.1-4 
-dialkylamino-C.sub.1-4 -alkyl, in particular dimethylaminomethyl, 
dimethylaminoethyl, amino, hydroxyl, C.sub.1-4 -alkoxy, in particular 
methoxy, C.sub.1-4 -alkylcarbonyl, in particular methylcarbonyl, C.sub.1-4 
-alkoxycarbonyl, in particular methoxycarbonyl, halogen, in particular 
fluorine, chlorine, bromine or iodine, 
or a radical from the groups G.sup.7, G.sup.8, G.sup.9, G.sup.10 and 
G.sup.11 
##STR47## 
in which n can denote the numbers 0, 1, 2 or 3, 
R.sup.13 represents C.sub.1-4 -alkyl, in particular methyl or ethyl, and 
R.sup.14 represents hydrogen, straight-chain or branched C.sub.1-6 -alkyl, 
in particular, methyl, ethyl, C.sub.2-6 -alkenyl, in particular vinyl, 
2-propenyl, C.sub.2-6 -alkinyl, in particular 2-propinyl, C.sub.3-6 
-cycloalkyl, in particular cyclopropyl, C.sub.1-4 -alkoxycarbonyl, in 
particular methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, 
hydroxy-C.sub.1-4 -alkyl, in particular hydroxymethyl, hydroxyethyl, 
hydroxyethylsulfonylethyl, C.sub.1-4 -alkylamino, in particular 
methylamino, ethylamino, C.sub.1-4 -dialkylamino-C.sub.1-4 -alkyl, in 
particular dimethylaminomethyl, dimethylaminoethyl, C.sub.3-7 
-cycloalkylamino-C.sub.1-4 -alkyl, in particular N-pyrrolidinoethyl, 
N-morpholinoethyl, N-piperidinoethyl, N-thiomorpholinoethyl, N.sup.1 
-(N.sup.4 -methylpiperazino)-ethyl, C.sub.3-6 
-cycloalkylaminocarbonyl-C.sub.1-2 -alkyl, in particular 
N-morpholinocarbonylmethyl, cyano, aryl, in particular phenyl, 
aryl-C.sub.1-2 -alkyl, in particular phenylmethyl, hetaryl, in particular 
pyridyl or thiazolyl, heteroaryl-C.sub.1-2 -alkyl, in particular 
pyridylmethyl and thiazolylmethyl, which radicals can optionally be 
substituted by radicals from the series consisting of halogen, in 
particular fluorine, chlorine, bromine or iodine, C.sub.1-4 -alkyl, in 
particular methyl, C.sub.1-4 -halogenoalkyl, in particular 
trifluoromethyl, trichloromethyl, amino, hydroxyl, C.sub.1-4 -alkoxy, in 
particular methoxy, C.sub.1-2 -alkylenedioxy, in particular methylenedioxy 
or ethylenedioxy, C.sub.1-4 -halogenoalkoxy, in particular 
trifluoromethoxy, difluoromethoxy, C.sub.1-4 -alkylthio, in particular 
methylthio, C.sub.1-4 -halogenoalkylthio, in particular 
trifluoro-methylthio, C.sub.1-4 -alkylsulfonyl, in particular 
methylsulfonyl, C.sub.1-4 -alkylamino, in particular methylamino, 
di-C.sub.1-4 -alkylamino, in particular dimethylamino, C.sub.1-4 
-alkylcarbonyl, in particular methyl-carbonyl, C.sub.1-4 -alkoxycarbonyl, 
in particular methoxycarbonyl, 
with the proviso for the compounds of the general formula (Ia), in the case 
where 
R.sup.1 represents hydrogen, 
R.sup.2 and R.sup.3 represent methyl, 
R.sup.4 represents radicals other than methyl or n-butyl, 
and optical isomers or racemates thereof. 
Especially preferred compounds are those of the formula (I) and salts 
thereof 
##STR48## 
in which R.sup.1 represents hydrogen, 
R.sup.2 represents straight-chain or branched branched C.sub.1-4 -alkyl, in 
particular methyl, ethyl, 
R.sup.3 represents methyl, 
R.sup.4 represent straight-chain or branched C.sub.1-6 -alkyl, in 
particular methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, n-butyl, 
C.sub.3-6 -cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, 
C.sub.3-6 -cycloalkyl-C.sub.1-2 -alkyl, in particular cyclopropylmethyl, 
phenyl-C.sub.1-2 -alkyl, in particular phenylmethyl, 2-phenylethyl, 
phenyl, N-morpholinyl, hetero-C.sub.1-2 -alkyl, in particular 
2-chloro-pyrid-5-yl-methyl, morpholinylethyl and 
chlorothiazol-5-yl-methyl, where the phenyl or hetaryl radicals can be 
substituted by halogen, methyl, halogenomethyl, phenyl, phenoxy, C.sub.1-4 
-alkylphenyl, C.sub.1-4 -halogeno-alkylphenoxy, C.sub.1-4 -alkylphenoxy, 
R.sup.5 represent hydrogen, straight-chain or branched C.sub.1-6 -alkyl, in 
particular methyl, ethyl, cyano-C.sub.1-4 -alkyl, in particular 
2-cyanoethyl, C.sub.1-4 -alkanoyloxy-C.sub.1-4 -alkyl, in particular 
methoxycarbonylmethyl, C.sub.2-6 -alkenyl, in particular 2-propenyl, 
C.sub.2-6 -alkinyl, in particular 2-propinyl, C.sub.1-4 -alkoxydicarbonyl, 
in particular methoxydicarbonyl or ethoxydicarbonyl, heteroaryl-C.sub.1-2 
-alkyl, in particular 5-chloropyrid-2-yl-methyl and 
chloro-thiazol-5-yl-methyl, 
or a radical from the group consisting of G.sup.1, G.sup.2, G.sup.3 and 
G.sup.4 
##STR49## 
in which R.sup.6 represent hydrogen or methyl, 
R.sup.7 represent hydrogen, straight-chain or branched alkyl having up to 6 
carbon atoms, in particular methyl or ethyl, 
R.sup.8 for hydrogen, 
##STR50## 
represents carboxyl or sulfonyl, Q represents a radical from the group 
consisting of G.sup.5 and G.sup.6 
##STR51## 
in which 
##STR52## 
can denote carboxyl or sulfonyl, Y represents oxygen or --NR.sup.12, 
R.sup.11, in the case where Y represents nitrogen, denotes a cyclic amino 
group which is linked via a nitrogen atom, in particular pyrrolidino, 
1-pyrrolyl, piperidino, morpholino, thiomorpholino, dioxothiomorpholino, 
R.sup.11 and R.sup.12 independently represent straight-chain or branched 
C.sub.1-4 -alkyl, in particular methyl, ethyl, propyl, isopropyl, 
sec-butyl, C.sub.2-4 -alkenyl, in particular vinyl, 2-propenyl, 
1-methyl-2-propenyl, C.sub.2-4 -alkinyl, in particular ethinyl, 
2-propinyl, C.sub.3-6 -cycloalkyl, in particular cyclopropyl, 
heteroaryl-C.sub.1-2 -alkyl, in particular 5-chloro-pyrid-2-yl-methyl and 
chlorothiazol-5-yl-methyl, or 
R.sup.11 and R.sup.12, together with the adjacent N atom, represent a 
carbocyclic 5-, 6- or 7-membered ring system, which can optionally also be 
interrupted by oxygen, sulfur, sulfonyl, carbonyl, --N.dbd., --NR.sup.14 
-- or by quaternized nitrogen and optionally by C.sub.1-4 -alkyl, in 
particular methyl, thyl, hydoxy-C.sub.1-4 -alkyl, in particular 
hydroxymethyl, amino-C.sub.1-4 -dialkylamino-C.sub.1-4 -alkyl, in 
particular dimethylaminomethyl, hydroxyl, C.sub.1-4 -alkoxycarbonyl, in 
particular methoxycarbonyl, 
or a radical from the groups consisting of G.sup.7, G.sup.8, G.sup.9, 
G.sup.10 and G.sup.11 
##STR53## 
in which n can denote the numbers 0, 1 or 2, 
R.sup.13 represents C.sub.1-4 -alkyl, in particular methyl, and 
R.sup.14 represents straight-chain or branched C.sub.1-6 -alkyl, in 
particular methyl, C.sub.2-6 -alkenyl, in particular vinyl, 2-propenyl, 
C.sub.2-6 -alkinyl, in particular 2-propinyl, C.sub.3-6 -cycloalkyl, in 
particular cyclopropyl, C.sub.1-4 -alkoxycarbonyl, in particular 
methoxycarbonyl, hydroxy-C.sub.1-4 -alkyl, in particular hydroxyethyl, 
hydroxyethylsulfonylethyl, C.sub.1-4 -alkyl-amino, in particular 
methylamino, ethylamino, C.sub.1-4 -dialkylamino-C.sub.1-4 -alkyl, in 
particular dimethylaminoethyl, C.sub.3-7 -cycloalkylamino-C.sub.1-4 
-alkyl, in particular N-morpholinoethyl, N-piperidinoethyl, C.sub.3-6 
-cycloalkylaminocarbonyl-C.sub.1-2 -alkyl, in particular 
N-morpholino-carbonylmethyl, 
with the proviso for the compounds of the general formula (Ia), in the case 
where 
R.sup.1 represents hydrogen, 
R.sup.2 and R.sup.3 represent methyl, 
R.sup.4 represents radicals other than methyl or n-butyl, 
and optical isomers and racemates thereof 
The compound of the general formula (I) and salts thereof to be used 
according to the invention furthermore contain one or more chirality 
centres and can thus be present as pure stereoisomers or in the form of 
various enantiomer and diastereoisomer mixtures, which can be separated in 
a manner known per se if necessary. The invention therefore relates both 
to the pure enan-tiomers and diastereomers and to mixtures thereof for 
controlling endoparasites, in particular in the field of medicine and 
veterinary medicine. 
Preferably, however, the optically active, stereoisomeric forms of the 
compounds of the general formula (I) and salts thereof are used according 
to the invention. 
Suitable salts of the compounds of the general formula (I) which may be 
mentioned are the customary non-toxic salts, i.e. salts with various bases 
and salts with added acids. Salts which may be mentioned as preferred are 
those with inorganic, bases, such as alkali metal salts, for example 
sodium, potassium or caesium salts, alkaline earth metal salts, for 
example calcium or magnesium salts, ammonium salts, salts with organic 
bases and with organic amines, for example triethylammonium, pyridinium, 
picolinium, ethanolammonium, triethanolammonium, dicyclohexylammonium or 
N,N'-dibenzylethylenedi-ammonium salts, salts with inorganic acids, for 
example hydrochlorides, hydrobromides, dihydrosulfates or 
trihydrophosphates, salts with organic carboxylic acids or organic 
sulfonic acids, for example formates, acetates, trifluoroacetates, 
maleates, tartrates, methanesulfonates, benzenesulfonates or 
para-toluenesulfonates, salts with basic amino acids or acid amino acids, 
for example arginates, aspartates or glutamates. 
Examples of the novel compounds according to the invention are listed in 
Tables 1 to 52. 
TABLE 1 
______________________________________ 
(Ib-1) 
#STR54## 
- Compounds of Table 1 correspond to the general formula (Ib-1), in 
which R.sup.1 = --H, R.sup.2, R.sup.3, 
R.sup.4 = -methyl; R.sup.5 is as listed 
below: 
Compound 
No. R.sup.5 
______________________________________ 
1 --SO.sub.2 --Me 
2 --SO.sub.2 --Et 
3 --SO.sub.2 --iPr 
4 --SO.sub.2 --CH.sub.2 --Cl 
5 --CO--Me 
6 --CO--CH.sub.2 --Cl 
7 --CO--CF.sub.3 
8 --CO--CCl.sub.3 
9 --CO-cyclopropyl 
10 --CO--O--Me 
11 --CH.sub.2 --CH.tbd.CH 
12 --CO--NMe--CO--NMe.sub.2 
13 --CO--NMe--CO--NEt.sub.2 
14 
cyclopropyl 
15 --CO--O--(CH.sub.2).sub.2 --CF.dbd.CF.sub.2 
16 pyrazin-2-yl- 
17 --CS--NMe.sub.2 
18 --CO--NMe.sub.2 
- 19 
#STR55## 
- 20 
#STR56## 
- 21 
#STR57## 
- 22 
#STR58## 
- 23 --CH.sub.2 C.tbd.N 
24 --PO(O--Et).sub.2 
25 --CO--CH.sub.2 --NH.sub.2 
26 --CO--CH.sub.2 --NH--Me 
27 --CO--CH.sub.2 --NMe.sub.2 
28 --CO--CH.sub.2 --NMe.sub.3.sup.+ I.sup.- 
29 --CO--CH.sub.2 --NMe--Z 
30 --CO--CHMe--NH.sub.2 
31 --CO--CHMe--NH--Me 
32 --CO--CHMe--NMe.sub.2 
33 --CO--CHMe--NMe.sub.3 .sup.+ I.sup.- 
34 --CO--CHMe--NMe--Z 
35 --CO--CHEt--NH--Me 
36 --CO--CHiPr--NH--Me 
37 --CO--NH--Me 
38 --CH.sub.2 --CH.sub.2 --NMe.sub.2 
39 --CH.sub.2 --CO--OEt 
40 --CHMe--CO--OMe 
- 41 
#STR59## 
- 42 
#STR60## 
- 43 
#STR61## 
- 44 
#STR62## 
- 45 
#STR63## 
- 46 
#STR64## 
- 47 
#STR65## 
- 48 
#STR66## 
- 49 
#STR67## 
- 50 
#STR68## 
- 51 
#STR69## 
- 52 
#STR70## 
- 53 
#STR71## 
- 54 
#STR72## 
- 55 
#STR73## 
- 56 
#STR74## 
- 57 
#STR75## 
- 58 
#STR76## 
- 59 
#STR77## 
- 60 
#STR78## 
- 61 
#STR79## 
- 62 
#STR80## 
- 63 
#STR81## 
- 64 
#STR82## 
- 65 
#STR83## 
- 66 
#STR84## 
- 67 
#STR85## 
- 68 
#STR86## 
- 69 
#STR87## 
- 70 
#STR88## 
- 71 
#STR89## 
- 72 
#STR90## 
- 73 
#STR91## 
- 74 
#STR92## 
- 75 
#STR93## 
- 76 
#STR94## 
- 77 
#STR95## 
- 78 
#STR96## 
- 79 
#STR97## 
- 80 
#STR98## 
- 81 --CO--CH.sub.2 --NMe--O--Me 
82 --CO--O--CHMe--CH.dbd.CH.sub.2 
83 --SO.sub.2 --NMe--CO--O--Me 
84 --CO--CH.sub.2 --CF.dbd.CF.sub.2 
85 --CO--N(CH.sub.2 --CH.sub.2 --OH).sub.2 
- 86 
#STR99## 
- 87 
#STR100## 
- 88 
#STR101## 
- 89 
#STR102## 
- 90 
#STR103## 
- 91 
#STR104## 
- 92 
#STR105## 
- 93 
#STR106## 
- 94 --SO.sub.2 --CH.sub.2 --NMe--CH.sub.2 --C.tbd.CH 
95 --CO--CH.sub.2 --NMe--CH.sub.2 .tbd.CH 
96 --CO--CH.sub.2 --NMe--CH.sub.2 --C.dbd.CH 
97 --PS(O--Et).sub.2 
98 --CO--CH.sub.2 --NMe--CHMe--Ph 
- 99 
#STR107## 
- 100 
#STR108## 
- 101 
#STR109## 
- 102 
#STR110## 
- 103 
#STR111## 
- 104 
##STR112## 
______________________________________ 
TABLE 2 
Table 2 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-ethyl; R.sup.5 has the 
meanings listed in Table 1. 
TABLE 3 
Table 3 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-n-propyl; R.sup.5 has 
the meanings listed in Table 1. 
TABLE 4 
Table 4 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-isopropyl; R.sup.5 has 
the meanings listed in Table 1. 
TABLE 5 
Table 5 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-cyclopropyl; R.sup.5 
has the meanings listed in Table 1. 
TABLE 6 
Table 6 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-n-butyl; R.sup.5 has 
the meanings listed in Table 1. 
TABLE 7 
Table 7 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-sec-butyl; R.sup.5 has 
the meanings listed in Table 1. 
TABLE 8 
Table 8 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-isobutyl; R.sup.5 has 
the meanings listed in Table 1. 
TABLE 9 
Table 9 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-cyclobutyl; R.sup.5 has 
the meanings listed in Table 1. 
TABLE 10 
Table 10 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-cyclopropylmethyl; 
R.sup.5 has the meanings listed in Table 1. 
TABLE 11 
Table 11 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-cyclopentyl; R.sup.5 
has the meanings listed in Table 1. 
TABLE 12 
Table 12 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =2-phenylethyl; R.sup.5 
has the meanings listed in Table 1. 
TABLE 13 
Table 13 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-allyl; R.sup.5 has the 
meanings listed in Table 1. 
TABLE 14 
Table 14 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl R.sup.4 = 
##STR113## 
R.sup.5 has the meanings listed in Table 1. 
TABLE 15 
Table 15 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 = 
##STR114## 
R.sup.5 has the meanings listed in Table 1. 
TABLE 16 
Table 16 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 .dbd.--CH.sub.2 --Br, R.sup.3, R.sup.4 =-methyl; 
R.sup.5 has the meanings listed in Table 1. 
TABLE 17 
Table 17 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 .dbd.--CH.sub.2 --Br, R.sup.3 =-methyl; R.sup.4 
=-ethyl; R.sup.5 has the meanings listed in Table 1. 
TABLE 18 
Table 18 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 .dbd.--CH.sub.2 --Br, R.sup.3 =-methyl; R.sup.4 
=-cyclopropyl; R.sup.5 has the meanings listed in Table 1. 
TABLE 19 
Table 19 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 =--CH.sub.2 --Br, R.sup.3 =-methyl; R.sup.4 
=-n-butyl; R .sup.5 has the meanings listed in Table 1. 
TABLE 20 
Table 20 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 =--CH.sub.2 --Br, R.sup.3 =-methyl; R.sup.4 
=-cyclobutyl; R.sup.5 has the meanings listed in Table 1. 
TABLE 21 
Table 21 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR115## 
R.sup.3, R.sup.4 =-methyl; R.sup.5 has the meanings listed in Table 1. 
TABLE 22 
Table 22 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR116## 
R.sup.3 =-methyl; R.sup.4 =-ethyl; R.sup.5 has the meanings listed in 
Table 1. 
TABLE 23 
Table 23 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR117## 
R.sup.3 =-methyl; R.sup.4 =-cyclopropyl; R.sup.5 has the meanings listed 
in Table 1. 
TABLE 24 
Table 24 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR118## 
R.sup.3 =-methyl; R.sup.4 =-n-butyl; R.sup.5 has the meanings listed in 
Table 1. 
TABLE 25 
Table 25 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR119## 
R.sup.3, R.sup.4 =-methyl; R.sup.5 has the meanings listed in Table 1. 
TABLE 26 
Table 26 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR120## 
R.sup.3 =-methyl; R.sup.4 =-ethyl; R.sup.5 has the meanings listed in 
Table 1. 
TABLE 27 
Table 27 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR121## 
R.sup.3 =-methyl; R.sup.4 =-cyclopropyl; R.sup.5 has the meanings listed 
in Table 1. 
TABLE 28 
Table 28 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR122## 
R.sup.3 =-methyl; R.sup.4 =-n-butyl; R.sup.5 has the meanings listed in 
Table 1. 
TABLE 29 
Table 29 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR123## 
R.sup.3, R.sup.4 =-methyl; R.sup.5 has the meanings listed in Table 1. 
TABLE 30 
Table 30 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR124## 
R.sup.3 =-methyl; R.sup.4 =-ethyl; R.sup.5 has the meanings listed in 
Table 1. 
TABLE 31 
Table 31 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR125## 
R.sup.3 =-methyl; R.sup.4 =-cyclopropyl; R.sup.5 has the meanings listed 
in Table 1. 
TABLE 32 
Table 32 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR126## 
R.sup.3 =-methyl; R.sup.4 =-n-butyl; R.sup.5 has the meanings listed in 
Table 1. 
TABLE 33 
Table 33 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 .dbd.--CO--O--Me, R.sup.3, R.sup.4 =-methyl; R.sup.5 
has the meanings listed in Table 1. 
TABLE 34 
Table 34 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 .dbd.--CO--O--Me, R.sup.3 =-methyl; R.sup.4 =-ethyl; 
R.sup.5 has the meanings listed in Table 1. 
TABLE 35 
Table 35 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 .dbd.--CO--O--Me, R.sup.3 =-methyl; R.sup.4 
=-cyclopropyl; R.sup.5 has the meanings listed in Table 1. 
TABLE 36 
Table 36 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 .dbd.--CO--O--Me, R.sup.3 =-methyl; R.sup.4 
=-n-butyl; R.sup.5 has the meanings listed in Table 1. 
TABLE 37 
Table 37 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR127## 
R.sup.3, R.sup.4 =-methyl; R.sup.5 has the meanings listed in Table 1. 
TABLE 38 
Table 38 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR128## 
R.sup.3 =-methyl; R.sup.4 =-ethyl; R.sup.5 has the meanings listed in 
Table 1. 
TABLE 39 
Table 39 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR129## 
R.sup.3 =-methyl; R.sup.4 =-cyclopropyl; R.sup.5 has the meanings listed 
in Table 1. 
TABLE 40 
Table 40 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR130## 
R.sup.3 =-methyl; R.sup.4 =-n-butyl; R.sup.5 has the meanings listed in 
Table 1. 
TABLE 41 
Table 41 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR131## 
R.sup.3, R.sup.4 =-methyl; R.sup.5 has the meanings listed in Table 1. 
TABLE 42 
Table 42 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR132## 
R.sup.3 =-methyl; R.sup.4 =-ethyl; R.sup.5 has the meanings listed in 
Table 1. 
TABLE 43 
Table 43 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR133## 
R.sup.3 =-methyl; R.sup.4 =-cyclopropyl; R.sup.5 has the meanings listed 
in Table 1. 
TABLE 44 
Table 44 contains the compounds of the general formula (Ib-1), in which 
R.sup.1 =--H; R.sup.2 = 
##STR134## 
R.sup.3 =-methyl; R.sup.4 =-n-butyl; R.sup.5 has the meanings listed in 
Table 1. 
TABLE 45 
##STR135## 
Table 45 contains the compounds of the general formula (Ic-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3, R.sup.4 =-methyl; R.sup.5 has the meanings 
listed in Table 1. 
TABLE 46 
Table 46 contains the compounds of the general formula (Ic-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-ethyl; R.sup.5 has the 
meanings listed in Table 1. 
TABLE 47 
Table 47 contains the compounds of the general formula (Ic-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-n-propyl; R.sup.5 has 
the meanings listed in Table 1. 
TABLE 48 
Table 48 contains the compounds of the general formula (Ic-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 -isopropyl; R.sup.5 has 
the meanings listed in Table 1. 
TABLE 49 
Table 49 contains the compounds of the general formula (Ic-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-cyclopropyl; R.sup.5 
has the meanings listed in Table 1. 
TABLE 50 
Table 50 contains the compounds of the general formula (Ic-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-n-butyl; R.sup.5 has 
the meanings listed in Table 1. 
TABLE 51 
Table 51 contains the compounds of the general formula (Ic-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-cyclopropylmethyl; 
R.sup.5 has the meanings listed in Table 1. 
TABLE 52 
Table 52 contains the compounds of the general formula (Ic-1), in which 
R.sup.1 =--H; R.sup.2, R.sup.3 =-methyl; R.sup.4 =-2-phenylethyl; R.sup.5 
has the meanings listed in Table 1. 
The compounds of the formula (Ia) are known in some cases, and they can be 
prepared by process a) described above under point 3 (cf., for example: T. 
Hisano et al. Chem. Pharm. Bull. 35 (3), (1987) pages 1049-1057; 
Heterocycles 29 (6), (1989) pages 1029-1032; Chem. Pharm. Bull. 38 (3), 
(1990) pages 605-611; Chem. Pharm. Bull. 39 (1), (1991) pages 10-17). 
If 3,5-dimethyl-pyridine N-oxide is employed as compounds of the general 
formula (II) and N-benzyl-maleimide is employed as compounds of the 
formula (III) in process 3a for the preparation of the novel 4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Ia), the process can be represented by 
the following equation: 
##STR136## 
Formula (II) provides a general definition of the substituted pyridine 
N-oxides required as starting substances for carrying out process 3a 
according to the invention. In this formula, R.sup.1, R.sup.2, R.sup.3 
preferably represent those radicals which have already been mentioned as 
preferred for these substituents in connection with the description of the 
substances of the formula (I) according to the invention. 
The substituted pyridine N-oxides used as starting materials are known in 
some cases, and can be ob-tained in some cases commercially or by methods 
known from the literature (for example J. M. Essery and K. Schofield J. 
Chem. Soc. (1960) page 49539). 
##STR137## 
The most diverse peroxides, such as hydrogen peroxide, tert-butylperoxide, 
organic or inorganic peroxides or salts thereof, such as 
3-chloro-perbenzo-ic acid, peracetic acid, performic acid, 
dibenzoylperoxide and the like, are possible for the oxidation of the 
pyridine derivatives to give the N-oxides of the general formula (II). 
The peroxide can also be prepared in situ from another peroxide, for 
example peracetic acid from acetic acid and hydrogen peroxide. 
The peroxide is preferably employed in equal equivalents to the starting 
pyridine. It is also possible to use an excess in order to bring the 
reaction to completion. All solvents which do not themselves undergo 
interfering side reactions with the oxidizing agents are suitable, such 
as, for example, water, alkyl alcohols, carboxylic acids, such as acetic 
acid or formic acid, or halogenated hydrocarbons, such as, inter alia, 
methylene chloride. The reaction temperatures are between -30.degree. C. 
and +130.degree. C., preferably between -10.degree. C. and +80.degree. C. 
Formula (III) provides a general definition of the N-substituted maleimides 
furthermore required as starting substances for carrying out process 3a 
according to the invention. In this formula, R.sup.4 preferably represents 
that radical which has already been mentioned as preferred for this 
substituent in connection with the description of the substances of the 
general formula (I) according to the invention. 
The N-substituted maleimides of the general formula (III) used as starting 
materials are known in some cases, and can be obtained in some cases 
commercially or by methods known from the literature (cf., for example: EP 
0608 445 A1, N. B. Mehta et al. J. Org. Chem. 25 (1960) pages 1012-1015; 
T. F. Braish et al. Synlett (1992) pages 979-980). 
In general, it is advantageous to carry out process 3a according to the 
invention in the presence of diluents. Diluents are advantageously 
employed in an amount such that the reaction mixture remains readily 
stirrable throughout the entire process. Possible diluents for carrying 
out process 3a according to the invention are all inert organic solvents. 
Examples which may be mentioned are: halogenohydrocarbons, in particular 
chlorohydrocarbons, such as tetrachloroethylene, tetrachloroethane, 
dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon 
tetrachloride, trichloroethane, trichloroethylene, pentachloroethane, 
difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, 
dichlorobenzene, chlorotoluene, trichlorobenzene; alcohols, such as 
methanol, ethanol, isopropanol, butanol; ethers, such as ethyl propyl 
ether, methyl tert-butyl ether, n-butyl ether, anisole, phenetole, 
cyclohexyl methyl ether, dimethyl ether, diethyl ether, di-propyl ether, 
diisopropyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, 
ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, dichlorodiethyl 
ether and polyethers of ethylene oxide and/or propylene oxide; amines, 
such as trimethyl-, triethyl-, tripropyl-, tributylamine, 
N-methyl-morpholine, pyridine and tetramethylenediamine, 
nitrohydrocarbons, such as nitromethane, nitroethane, nitropropane, 
nitrobenzene, chloronitrobenzene, o-nitrotoluene; nitriles, such as 
acetonitrile, propionitrile, butyronitrile, isobutyronitrile, 
benzonitrile, m-chloro-benzonitrile, and compounds such as 
tetrahydro-thiophene dioxide and dimethyl sulfoxide, tetramethylene 
sulfoxide, dipropyl sulfoxide, benzylmethyl sulfoxide, diisobutyl 
sulfoxide, dibutyl sulfoxide, diisoamyl sulfoxide; sulfones, such as 
dimethyl, diethyl, dipropyl, dibutyl, diphenyl, dihexyl, methyl ethyl, 
ethyl propyl, ethyl isobutyl and pentamethylene sulfone; aliphatic, 
cycloalipha-tic or aromatic hydrocarbons, such as pentane, hexane, 
heptane, octane, nonane and technical grade hydrocarbons, for example 
so-called white spirits with components having boiling points in the range 
of, for example, 40 to 250.degree. C., cymene, benzine fractions within a 
boiling point range of 70.degree. C. to 190.degree. C., cyclohexane, 
methylcyclohexane, petroleum ether, ligroin, octane, benzene, toluene, 
chlorobenzene, bromobenzene, nitrobenzene, xylene; esters, such as methyl, 
ethyl, butyl, isobutyl acetate, and dimethyl, dibutyl, ethylene carbonate; 
amides, such as hexamethylenephosphor triamide, formamide, 
N-methylformamide, N,N-dimethylformamide, N, N-dipropylformamide, 
N,N-dibutylformamide, N-methyl-pyrrolidone, N-methyl-capro-lactam, 
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidine, octylpyrrolidone, 
octylca-prolactam, 1,3-dimethyl-2-imidazolinedione, N-formylpiperidine, 
N,N'-1,4-diformyl-piperazine; ketones, such as acetone, acetophenone, 
methyl ethyl ketone, methyl butyl ketone. 
Mixtures of the solvents and diluents mentioned can of course also be 
employed in the process according to the invention. 
Preferred diluents are aromatic halogenohydrocarbons, in particular 
chlorobenzene and bromobenzene, aromatic nitrohydrocarbons, such as 
nitrobenzene, aromatic hydrocarbons, in particular benzene and toluene, 
ketones, such as acetophenone, amides, such as N,N-dimethylformamide, 
sulfoxides, such as tetramethylene and sulfoxide and or mixtures of these 
with other diluents mentioned. 
Process 3a is carried out by reacting substituted pyridine N-oxides of the 
general formula (II) with N-substituted maleimides of the general formula 
(III) in one of the diluents mentioned. 
The duration of the reaction is 4 to 72 hours. The reaction is carried out 
at temperatures between -10.degree. C. and +250.degree. C., preferably 
between 0.degree. C. and +200.degree. C., particularly preferably at room 
temperature to +150.degree. C. It is preferably carried out under the 
pressure which is established on heating to the required reaction 
temperature under the reaction conditions. 
For carrying out process 3a according to the invention, in general 1.0 to 
3.0 mol, preferably 1.0 to 2.0 mol, of N-substituted maleimide are 
employed per mol of compound of the formula (II). 
When the reaction is complete, the reaction solution is concentrated in 
vacuo. The products obtained can be purified in the customary manner by 
recrystallization, vacuum distillation or column chromatography (cf. also 
the preparation examples). 
The following compounds of the general formula (Ia) in which the radicals 
R.sup.1 to R.sup.4 have the following meaning may be mentioned 
specifically: 
__________________________________________________________________________ 
(Ia) 
#STR138## 
R.sup.1 
R.sup.2 R.sup.3 
R.sup.4 
__________________________________________________________________________ 
--H 
--CH.sub.3 --CH.sub.3 
--CH.sub.2 --CF.sub.3 
--H --CH.sub.3 --CH.sub.3 --CH.sub.2 --CH.sub.2 --F 
--H --CH.sub.3 --CH.sub.3 --CH.sub.2 --CH.sub.2 --CF.sub.3 
--H --CH.sub.3 --CH.sub.3 --CHMe.sub.2 
--H --CH.sub.3 --CH.sub.3 --CHMe--CF.sub.3 
--H --CH.sub.3 --CH.sub.3 --CH.sub.2 --C.tbd.CH 
--H --CH.sub.3 --CH.sub.3 --(R)--CHMe-phenyl 
--H --CH.sub.3 --CH.sub.3 --CH.sub.2 --CO--O--Me 
--H --CH.sub.3 --CH.sub.3 --CH.sub.2 --CO--O--tBu 
--H --CH.sub.3 --CH.sub.3 --(R)--CHMe--CO--O--tBu 
--H --CH.sub.3 --CH.sub.3 --(R)--CHMe--CO--O--Me 
--H --CH.sub.3 --CH.sub.3 --(S)--CHMe--CO--O--tBu 
--H --CH.sub.3 --CH.sub.3 --(S)--CHMe--CO--O--Me 
--H --CH.sub.2 --Br --CH.sub.3 --Me 
--H --CH.sub.2 --Br --CH.sub.3 --Et 
--H --CH.sub.2 --Br --CH.sub.3 
cyclopropyl 
--H --CH.sub.2 --Br --CH.sub.3 
cyclobutyl 
--H --CH.sub.2 --Br --CH.sub.3 
n-butyl 
--H --CH.sub.2 --Br --CH.sub.3 
sec-butyl 
--H --CH.sub.2 --Br --CH.sub.3 --(S)--CHMe-phenyl 
--H --CH.sub.2 --Br --CH.sub.3 
benzyl 
--H --CH.sub.2 --NMe.sub.2 --CH.sub.3 --Me 
--H --CH.sub.2 --NMe.sub.2 --CH.sub.3 --Et 
--H --CH.sub.2 --NMe.sub.2 --CH.sub.3 
cyclopropyl 
--H --CH.sub.2 --NMe.sub.2 --CH.sub.3 
cyclobutyl 
--H --CH.sub.2 --NMe.sub.2 --CH.sub.3 
n-butyl 
--H --CH.sub.2 --NMe.sub.2 --CH.sub.3 
sec-butyl 
--H --CH.sub.2 --NMe.sub.2 --CH.sub.3 --(S)--CHMe-phenyl 
--H --CH.sub.2 --NMe.sub.2 --CH.sub.3 
benzyl 
- --H 
--CH.sub.3 --Me 
- --H 
--CH.sub.3 --Et 
- --H 
--CH.sub.3 
cyclopropyl 
- --H 
--CH.sub.3 
n-butyl 
- --H 
--CH.sub.3 --Me 
- --H 
--CH.sub.3 --Et 
- --H 
--CH.sub.3 
cyclopropyl 
- --H 
--CH.sub.3 
n-butyl 
- --H 
--CH.sub.3 --Me 
- --H 
--CH.sub.3 --Et 
- --H 
--CH.sub.3 
cyclopropyl 
- --H 
--CH.sub.3 
n-butyl 
- --H 
--CH.sub.3 --Me 
- --H 
--CH.sub.3 --Et 
- --H 
--CH.sub.3 
cyclopropyl 
- --H 
--CH.sub.3 
n-butyl 
- --H --CO--O--Me --CH.sub.3 --Me 
--H --CO--O--Me --CH.sub.3 --Et 
--H --CO--O--Me --CH.sub.3 --CHMe.sub.2 
--H --CO--O--Me --CH.sub.3 
cyclopropyl 
--H --CO--O--Me --CH.sub.3 
n-butyl 
- --H 
--CH.sub.3 --Me 
- --H 
--CH.sub.3 --Et 
- --H 
--CH.sub.3 
cyclopropyl 
- --H 
--CH.sub.3 
n-butyl 
- --H 
--CH.sub.3 --Me 
- --H 
--CH.sub.3 --Et 
- --H 
--CH.sub.3 --Me 
- --H 
--CH.sub.3 --Et 
- --H 
--CH.sub.3 --Me 
- --H 
--CH.sub.3 --Et 
- --H 
--CH.sub.3 --Me 
- --H 
--CH.sub.3 --Et 
- --H 
--CH.sub.3 --Et 
__________________________________________________________________________ 
The present invention also relates to the compounds of the general formula 
(I) in the form of an acid addition salt. Acids which can be used for salt 
formation are inorganic acids, such as hydrochloric acid, hydrobromic 
acid, nitric acid, sulfuric acid, phosphoric acid or organic acids, such 
as formic acid, acetic acid, propionic acid, malonic acid, oxalic acid, 
fumaric acid, adipic acid, stearic acid, tartaric acid, oleic acid, 
methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid. 
Examples which may be mentioned of the preparation of suitable salts of 
compounds of the general formula (Ia) are hydrochloride formation and 
preparation of the corresponding N.sup.1 -methylammonium halides of the 
general formula (V), for example the N.sup.1 -methylammonium iodide of 
7-ethyl-4a, 5a, 8a, 
8b-tetrahydro-3,4a-di-methyl-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8( 
7H)-dione: 
##STR168## 
The salt formation is carried out by reacting compounds of the general 
formula (Ia), for example in the presence of inorganic acids, such as 
gaseous hydrochloric acid, or with an alkylating agent, such as methyl 
iodide, in one of the diluents mentioned for process 3a. 
The duration of the reaction is 10 minutes to 24 hours. The reaction is 
carried out at temperatures between -60.degree. C. and +150.degree. C., 
preferably between -10.degree. C. and +80.degree. C., particularly 
preferably at 0.degree. C. to room temperature. It is carried out under 
normal pressure. For the salt formation, in general an excess of acid or 
alkylating agent is employed per mol of compound of the formula (Ia). 
When the reaction is complete, the salt, which has usually precipitated 
out, is separated off, washed and dried in vacuo (cf. also the Preparation 
examples). 
Surprisingly, the novel 4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Ia) can be converted via hydrogenation 
of one or both double bonds in the dihydropyridine part into the novel 1, 
2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione and 1, 
2, 4a, 5a, 8a, 
8b-hexahydro-6H-pyrrolo-[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formulae (Id) and (Ie) and can be used for 
subsequent reactions according to process 5. 
In general, a procedure is followed in process 5 in which the novel 4a, 5a, 
8a, 8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Ia) are first hydrogenated in the 
presence of a catalyst and in the presence of a diluent, the corresponding 
novel 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8 
(7H)-dione-and/or 1, 2, 4a, 5a, 8a, 
8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8 (7H)dione 
derivatives of the general formulae (Id) and (Ie) being formed. 
As expected, the compounds of the general formula (Id) are present in the 
form of an isomer mixture comprising a 3.alpha. isomer and 3.beta. isomer. 
If, for example, 7-benzyl-4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione is 
employed as the compound of the general formula (Ia) for the 
hydrogenation, an isomer mixture of 7-benzyl-1, 2, 3, 4, 4a.alpha., 
5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dimethyl-6H-pyrrolo[3',4':4,5]furo[ 
3,2-b]pyridine-6,8(7H)-dione (3.alpha.-isomer) and 7-benzyl-1, 2, 3, 4, 
4a.alpha., 5a.alpha., 8a.alpha., 8b.alpha.-(.+-.)-octahydro-3.beta., 
4a-dimethyl-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
(3.beta.-isomer) is formed. 
##STR169## 
If, for example, 7-methyl-4a, 5a, 8a, 
8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione is 
used as the compound of the general formula (Ia) for the hydrogenation, in 
addition to the isomer mixture of 7-methyl-1, 2, 3, 4, 4a.alpha., 
5a.alpha., 8a.alpha., 8b.alpha.-(.+-.)-octahydro-3.alpha., 
4a-dimethyl-6H-pyrrolo[3',4':4,5]-furo[3,2-b]pyridine-6,8-(7H)-dione 
(3.alpha. isomer) and 7-methyl- 1, 2, 3, 4, 4a.alpha., 5a.alpha., 
8a.alpha., 8b.alpha.-(.+-.)-octahydro-3.beta., 
4a-dimethyl-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
(3.beta. iso-mer) of the general formula (Id), 7-methyl-1, 2, 4a, 5a, 8a, 
8b-hexahydro-6H-pyr-rolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione of 
the general formula (Ie) can also be obtained. 
##STR170## 
Diluents which are used for the hydrogenation are the inert organic 
solvents mentioned for process 3a such as, for example, alcohols, in 
particular ethanol. 
The formation of the 1, 2, 4a, 5a, 8a, 
8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)di-one 
derivatives of the general formula (Ie) according to the invention can be 
influenced by the hydrogenation conditions mentioned below. 
Possible suitable catalysts for carrying out the catalytic hydrogenation 
are all the customary hydrogenation catalysts, such as, for example, 
platinum catalysts (platinum sheet, platinum sponge, platinum black, 
colloidal platinum, platinum oxide, platinum wire and the like), palladium 
catalysts (for example palladium sponge, palladium black, palladium oxide, 
palladium-on-charcoal, colloidal palladium, palladium barium sulfate, 
palladium barium carbonate, palladium hydroxide and the like), nickel 
catalysts (for example reduced nickel, nickel oxide, Raney nickel and the 
like), ruthenium catalysts, cobalt catalysts (for example reduced cobalt, 
Raney cobalt and the like), iron catalysts (for example reduced iron, 
Raney iron and the like), copper catalysts (for example reduced copper, 
Raney copper, Ullman copper and the like). Preferably, however, noble 
metal catalysts, such as, for example, platinum and palladium or ruthenium 
catalysts, are used, if appropriate on a suitable support, such as, for 
example, carbon or silicon dioxide. 
For carrying out the hydrogenation, an alcoholic solution of the compounds 
of the formula (Ia) is reacted in the presence of a suitable hydrogenation 
catalyst, for example palladium hydroxide/charcoal. The duration of the 
reaction is 1 to 20 hours. The hydrogenation is carried out at 
temperatures of between +10.degree. C. and +150.degree. C., preferably 
between +15.degree. C. and +100.degree. C. 
The isomer mixtures (3.alpha. isomers and 3.beta. isomers) thus obtained 
are worked up in the customary manner, for example by purification by 
chromatography. (cf. also the Preparation examples). However, they can 
also be reacted directly (without further separation) in accordance with 
processes 5a to 5i. 
By using a "chiral hydrogenation catalyst", for example with chiral 
diphosphine ligands, for example 
(2S,3S)-(-)-2,3-bis-(diphenylphosphino)-butane [(S,S)-chiraphos] (N. K. 
Roberts in "Catalytic Aspects of Metal Phosphine Complexes" (1982) page 
337 ACS Washington) or R(+)-2,2'- or 
S(-)-2,2'-bis-(diphenylphosphino)-1,1'-binaphthalene [R(+)-BINAP or 
S(-)-BINAP] (cf. A. Miyashita et al. Tetrahedron 40 (1984) page 1245), the 
content of one isomer (3.alpha. isomer or 3.beta. isomer) in the isomer 
mixture can of course also be increased significantly, or the formation of 
another isomer (3.alpha. isomer or 3.beta. isomer) can even be suppressed 
completely. 
The 
1,2,4a,5a,8a,8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H) 
-dione derivatives of the general formula (1e) can be selectively prepared 
from the corresponding N.sup.1 -methylammonium halides of the general 
formula (V), such as for example the N.sup.1 -methylammonium iodide, 
followed by N.sup.1 -demethylation (cf. B. Fr.o slashed.lund et al., J. 
Med. Chem. 38, 1995, page 3287). 
The selective preparation of the 
1,2,4a,5a,8a,8b-hexahydro-6H-pyrrolo[3',4':4,5]furo-[3,2-b]pyridine-6,8(7H 
)-dione derivatives of the formula (1e) according to the invention can be 
illustrated by the hydrogenation of the corresponding N.sup.1 
-methylammonium iodide of 
7-methyl-4a.alpha.,5a.alpha.,8a.alpha.,8b.alpha.-tetrahydro-3,4a-dimethyl- 
6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione: 
##STR171## 
The hydrogenation of the corresponding N.sup.1 -methylammonium iodide is 
carried out by reacting compounds of the general formula (V), such as for 
example the N.sup.1 -methylammonium iodide of 7-methyl-4a.alpha., 
5a.alpha.,8a.alpha.,8b.alpha.-tetrahydro-3,4a-dimethyl-6H-pyrrolo[3',4':4, 
5]furo[3,2-b]pyridine-6,8(7,8)dione, in the presence of sodium 
hydridoborate in one of the diluents mentioned in connection with the 
subsequent process 3a. 
Inert organic solvents, such as for example alcohols, and in particular 
methanol or ethanol, are preferably used as diluents for the hydrogenation 
process. 
The reaction time is from 10 minutes to 48 hours. The reaction is carried 
out at temperatures of between -60.degree. C. and +100.degree. C., 
preferably between -30.degree. C. and +80.degree. C., and more preferably 
at from -10.degree. C. to room temperature. The reaction is carried out 
under atmospheric pressure. For the hydrogenation process a slight excess 
of hydrogenation agent is generally used per mol N.sup.1 -methylammonium 
halide of the formula (V). 
When the reaction is complete working up is carried out in the customary 
manner, such as for example by chromatographic purification (cf. also the 
preparation examples). 
In general the subsequent N.sup.1 -demethylation is carried out by first 
reaction the new 
1,2,4a,5a,8a,8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H) 
-diones of the general formula (VI) in the presene of a suitable 
chloroformic acid ester in the manner described by R. F. Olofson et 
al.(J.Org. Chem. 49, 4984, page 2081), as a result of which the 
corresponding carbamates of the 
1,2,4a,5a,8a,8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H) 
-diones of the general formula 1g) are formed (cf. also process 5i). 
The N.sup.1 -demethylation of the 
1,2,4a,5a,8a,8b-hexahydro-6H-pyrrolo[3',4':4,5]furo-[3,2-b]pyridine-6,8(7H 
)-diones of the general formula (VI) according to the invention can be 
illustrated by the elimination of the corresponding N.sup.1 -methyl 
radical from 
7-methyl-4a.alpha.,5a.alpha.,8a.alpha.,8b.alpha.-tetrahydro-3,4a-dimethyl- 
6H-pyrrolo-[3',4':4,5]furo[3,2-b]-pyridine-6,8(7H)-dione using 
1-chloroethoxycarbonyl chloride: 
##STR172## 
In order to carry out the N.sup.1 -demethylation the 
1,2,4a,5a,8a,8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H) 
-diones of the general formula (VI) are heated in the presence of an excess 
of 1-chloroethoxycarbonyl chloride. The reaction time is from 1 to 24 
hours. The N.sup.1 -demethylation is carried out at temperatures between 
0.degree. C. and +200.degree. C., preferably at tempeatures between 
+5.degree. C. and +150.degree. C., and more preferably at temperatures 
between +50.degree. C. and +130.degree. C. 
The 
1-chloroethoxycarbonyl-1,2,4a,5a,8a,8b-hexahydro-6H-pyrrolo[3',4':4,5]furo 
-[3,2-b]pyridine-6,8(7H)-diones obtained in this way are worked up in the 
customary manner, for example by means of chromatographic purification 
(cf. also the preparation examples). 
The the 1-chloroethoxycarbonyl-1,2,4a,5 
a,8a,8b-hexahydro-6H-pyrrolo[3',4':4,5]-furo[3,2-b]pyridine-6,8(7H)-diones 
are reacted in one of the diluents mentioned in relation to the subsequent 
process 3a. 
Inert organic solvents, such as for example alcohols, and in particular 
methanol or ethanol, are preferably used as diluents for the N.sup.1 
-demethylation. 
The reaction time is from 10 minutes to 24 hours. The reaction is carried 
out at a temperature between 0.degree. C. and +100.degree. C., preferably 
at temperatures between +10.degree. C. and +80.degree. C. The reaction can 
generally be carried out under atmospheric pressure. 
When the reaction is complete the resulting hydrochloride is worked up in 
the customary manner (cf. also the preparation examples). 
If 7-ethyl-1, 2, 3, 4, 4a.alpha., 5a.alpha., 
8a.alpha.,8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dimethyl-6H-pyrrolo[3'4': 
4, 5]furo[3,2-b]pyridine-6,8(7H)dione is employed as compounds of the 
general formula (Id) and methyl iodide is employed as compounds of the 
general formula (VII) in process 5a for the preparation of the novel 
1-substituted 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Ib), the process can be represented by 
the following equation: 
##STR173## 
Formula (Id) provides a general definition of the 1, 2, 3, 4, 4a.alpha., 
5a.alpha., 
8a.alpha.,8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo-[3',4' 
:4,5]furo[3,2-b]pyridine-6,8(7H)-diones required as starting substances for 
carrying out process 5a according to the invention. In this formula 
R.sup.1, R.sup.2, R.sup.3 and R.sup.4 preferably represent those radicals 
which have already been mentioned as preferred for these substituents in 
connection with the description of the substances of the general formula 
(Ib) according to the invention. 
The 1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo-[3',4':4,5]furo[3 
,2-b]pyridine-6,8(7H)-diones of the general formula (Id) used as starting 
materials are novel and can be obtained from the 4a, 5a, 8a, 
8b-tetrahydro-3,4a-dialkyl-6H-pyrrolo[3'4':4,5]furo[3,2-b]pyridine-6,8(7H) 
-dione derivatives (Ia) by the hydrogenation process described above. 
Formula (IV) provides a general definition of the alkylating or 
heteroarylating agents (R.sup.5 =heteroaryl) furthermore to be used as 
starting substances for carrying out process 5a according to the 
invention. 
In the formula (VII), R.sup.5 has the meaning which has already been 
mentioned as pre-ferred for these substituents in connection with the 
description of the substances of the general formula (Ib) according to the 
invention, and E has the meaning of an electron-withdrawing leaving group. 
Suitable leaving groups are, for example, halogen, such as fluorine, 
chlorine, bromine and iodine, sulfonate, such as aryl- and 
perfluoroalkylsulfonate, monosubstituted diazo and monosubstituted 
nitrato, and those additionally listed in J. March, Advanced Organic 
Chemistry, 3rd edition, John Wiley & Sons, New York 1985, pages 310-316. 
Alkylating or heteroarylating agents of the formula (VII) are generally 
known compounds of organic chemistry or can be obtained commercially or by 
methods known from the literature (for example: Houben-Weyl, Methoden der 
organischen Chemie [Methods of organic chemistry], Volume V/3, pages 830, 
862; Volume V/4, pages 361, 610). 
In general, it is advantageous to carry out process 5a according to the 
invention in the presence of diluents and if appropriate in the presence 
of a basic reaction auxiliary. 
Possible diluents for carrying out process 3a according to the invention 
are all the inert organic solvents. 
Preferred diluents are ketones, in particular acetone, methyl ethyl ketone 
or methyl isobutyl ketone, amides, in particular N,N-di-methylformamide, 
N,N-di-methyl-acetamide or N-methyl-pyrrolidone, benzine fractions within 
a boiling point range of 70.degree. C. to 190.degree. C., in particular 
benzene, toluene, chlorobenzene, bromobenzene, nitrobenzene or xylene, and 
mixtures of these with other diluents mentioned. 
Mixtures of the solvents and diluents mentioned can of course also be 
employed in process 5a according to the invention. 
All suitable acid-binding agents can be employed as basic reaction 
auxiliaries for carrying out process 5a according to the invention, such 
as amines, in particular tertiary amines, and alkali metal and alkaline 
earth metal compounds. 
Examples of these which may be mentioned are the hydrides, hydroxides, 
oxides and carbonates of lithium, sodium, potassium, magnesium, calcium 
and barium, and furthermore other basic compounds, such as amidine bases 
or guanidine bases, such as 7-methyl-1,5,7-triazabicyclo(4.4.0)dec-5-ene 
(MTBD); diazabicyclo(4.3.0)-nonene (DBN), diazabicyclo(2.2.2)-octane 
(DABCO), 1,8-diazabicyclo-(5.4.0)undecene (DBU) 
cyclohexyltetra-butylguanidine (CyTBG), cyclohexyltetra-methylguanidine 
(CyTMG), N,N,N,N-tetramethyl-1,8-naphthalenediamine, 
pentamethyl-piperidine, tertiary amines, such as triethylamine, 
trimethylamine, tribenzylamine, tri-isopropylamine, tributylamine, 
tribenzylamine, tricyclohexylamine, tri-amylamine, trihexylamine, 
N,N-dimethylaniline, N,N-dimethyltoluidine, N,N-dimethyl-p-aminopyridine, 
N-methyl-pyrrolidine, N-methylpiperidine, N-methylimidazole, 
N-methyl-pyrrol, N-methyl-morpholine, N-methylhexa-methyleneimine, 
pyridine, 4-pyrrolidinopyridine, 4-dimethylamino-pyridine, quinoline, 
.alpha.-picoline, .beta.-picoline, isoquinoline, pyrimidine, acridine, 
N,N,N,N'-tetramethylenediamine, N,N',N'-tetra-ethylenediamine, 
quinoxaline, N-propyl-diisopropylamine, N-ethyl-diisopropylamine, 
N,N'-dimethylcyclohexylamine, 2,6-lutidine, 2,4-lutidine or 
triethylenediamine. 
Tertiary amines, in particular trialkylamines, such as triethylamine, 
N,N-diisopropylethylamine, N-propyl-diisopropylamine, 
N,N'-dimethylcyclohexyl-amine or N-methylmorpholine, and alkali metal 
carbonates, in particular sodium bicarbonate, sodium carbonate, potassium 
carbonate or potassium bicarbonate, are preferably used. 
Process 5a is carried out by reacting compounds of the general formula (Id) 
with compounds of the general formula (VII) in the presence of a basic 
reaction auxiliary in one of the diluents mentioned. 
The duration of the reaction is 4 to 72 hours. The reaction is carried out 
at temperatures between -10.degree. C. and +250.degree. C., preferably 
between 0.degree. C. and +200.degree. C., particularly preferably at 
0.degree. C. to 150.degree. C. It is carried out under normal pressure. 
For carrying out process 5a according to the invention, in general 1.0 to 
6.0 mol, preferably 1.0 to 4.0 mol, of basic reaction auxiliary and 1.0 to 
4.0 mol, preferably 1.0 to 2.0 mol, of alkylating agent (VII) are employed 
per mol of compound of the formula (Id). 
When the reaction is complete, the reaction solution is washed and the 
organic phase is separated off, dried and concentrated in vacuo. The 
products obtained can be purified in a customary manner by 
recrystallization, vacuum distillation or column chromatography (cf. also 
the Preparation examples). 
If appropriate, the amino alkylation or reductive amino alkylation known 
from the literature (cf. Houben-Weyl, Methoden der Organischen Chemie 
[Methods of organic chemistry], Volume XI/I, page 648; W. S. Emerson, Org. 
Reactions 4 (1948), page 174) is also suitable for preparation of 
compounds of the general formula (Ib) and (Ic) for process 5a according to 
the invention. 
If 7-ethyl-1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dimethyl-6H-pyrrolo[3',4':4,5]furo[ 
3,2-b] pyridine-6,8(7H)dione is employed as compounds of the general 
formula (Id) and acrylonitrile is employed as the compound of the general 
formula (VIII) in process 5b for the preparation of the novel 1, 2, 3, 4, 
4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Ib), the process can be represented by 
the following equation: 
##STR174## 
Formula (Id) provides a general definition of the 1, 2, 3, 4, 4a.alpha., 
5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo[3',4':4,5]furo[3 
,2-b]pyridine-6,8(7H)-diones required as starting substances for carrying 
out process 5b according to the invention. In this formula, R.sup.1, 
R.sup.2, R.sup.3 and R.sup.4 preferably represent those radicals which 
have already been mentioned as preferred for these substituents in 
connection with the description of the substances of the general formula 
(Ib) according to the invention. 
The 1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo-[3',4':4,5]furo[ 
3,2-b]pyridine-6,8(7H)-diones of the general formula (Id) used as starting 
materials are novel and can be obtained from the 4a, 5a, 8a, 
8b-tetrahydro-3,4a-dialkyl-6H-pyrrolo [3',4':4,5]furo 
[3,2-b]pyridine-6,8(7H)-dione derivatives (Ia) by the hydrogenation 
process described above. 
Formula (VIII) provides a general definition of the compounds furthermore 
to be used as starting substances for carrying out process 5b according to 
the invention. 
In the formula (VIII) R.sup.8 has the meaning which have already been 
mentioned as preferred for these substituents in connection with the 
description of the substances of the general formula (Ib) according to the 
invention, and A represents a suitable ac-ceptor group, for example nitro, 
nitrile, carbamoyl, carboxyl or C.sub.1-4 -alkoxycarbonyl. 
The compounds of the formula (VIII) are generally known compounds of 
organic chemistry and they can be obtained in some cases commercially or 
by methods known from the literature (for example: Houben-Weyl, Methoden 
der Organischen Chemie [Methods of organic chemistry], Volume VIII, page 
265). 
The reaction of the compounds (Id) with (VIII) is carried out, if 
appropriate, in the presence of a catalyst using diluents. 
Diluents which are used for carrying out process 5b according to the 
invention are the inert solvents mentioned for process 3a, such as, for 
example, alcohols, in particular methanol or ethanol. 
Process 5b is carried out by reacting compounds of the general formula (Id) 
with a compound general formula (VIII), if appropriate in the presence of 
a suitable catalyst, in one of the diluents mentioned. 
The duration of the reaction is 4 to 72 hours. The reaction is carried out 
at temperatures between -10.degree. C. and +200.degree. C., preferably 
between -5.degree. C. and +150.degree. C., particularly preferably at 
0.degree. C. to 100. It can in principle be carried out under normal 
pressure, but can also be carried out under increased or reduced pressure. 
Preferably, the reaction is carried out under normal pressure or under 
pressures of up to 15 bar. At higher temperatures, it is advantageous to 
carry out the reaction under increased pressure, if appropriate also above 
15 bar. 
For carrying out process 5b according to the invention, in general 1.0 to 
3.0 mol, preferably 1.0 to 2.0 mol, of compound of the formula (VIII) are 
employed per mol of compound of the formula Id. 
When the reaction is complete, the reaction solution is washed and the 
organic phase is separated off, dried and concentrated in vacuo. The 
products obtained can be purified in a customary manner by 
recrystallization, vacuum distillation or column chromatography (cf. also 
the Preparation examples). 
If 7-ethyl-1,2,3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha., 
4a-dimethyl-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6, 8(7H)-dione is 
employed as compounds of the general formula (Id) and 
(.+-.)-2,3-epoxypropyl iso-propyl ether is employed as the epoxide of the 
general formula (IX) in process 5c for the preparation of the novel 1, 2, 
3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Ib), the process can be represented by 
the following equation: 
##STR175## 
Formula (Id) provides a general definition of the 1, 2, 3, 4, 4a.alpha., 
5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3a.alpha.,4a-dialkyl-6H-pyrrolo-[3',4':4,5]furo 
[3,2-b]pyridine-6,8(7H)-diones required as starting substances for carrying 
out process 5c according to the invention. In this formula, R.sup.1, 
R.sup.2, R.sup.3 and R.sup.4 preferably represent those radicals which 
have already been mentioned as preferred for these substituents in 
connection with the description of the substances of the general formula 
(Ib) according to the invention. 
The 1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo[3',4':4,5]furo[3 
,2-b]pyridine-6,8(7H)-diones of the general formula (Id) used as starting 
materials are novel and can be obtained from the 4a, 5a, 8a, 
8b-tetrahydro-3,4a-dialkyl-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H 
)-dione derivatives (Ia) by the hydrogenation process described above. 
Formula (IX) provides a general definition of the epoxides furthermore to 
be used as starting substances for carrying out process 5c according to 
the invention. 
In the formula (IX) R.sup.5 has the meaning which have already been 
mentioned as preferred for these substituents in connection with the 
de-scription of the substances of the general formula (Ib) according to 
the invention. 
The epoxides of the formula (IX) are generally known compounds of organic 
chemistry, and they can be obtained in some cases commercially or by 
methods known from the literature (for example: Houben-Weyl, Methoden der 
Organischen Chemie [Methods of organic chemistry], Volume VI/3, page 371; 
D. Swern, Org. Reactions 7 (1953), page 378). 
The reaction of the compounds (Id) with (IX) is carried out, if 
appropriate, in the presence of a catalyst or in the presence of a basic 
reaction auxiliary using diluents. 
Diluents which are used for carrying out process 5c according to the 
invention are the inert, aprotic solvents mentioned for process 3a, such 
as, for example, ethers, in particular methyl tert-butyl ether, 
tetrahydrofuran or dioxane, alcohols, in particular methanol. 
All the basic reaction auxiliaries mentioned for process 5a, in particular 
alkali metal hydrides, can be used as reaction auxiliaries employed, if 
appropriate, for carrying out process 5c according to the invention. 
Process 5c is carried out by reacting compounds of the general for-mula 
(Id) with an epoxide of the general formula (IX) in, if appropriate, the 
presence of a reaction auxiliary in one of the diluents mentioned. 
The duration of the reaction is 4 to 72 hours. The reaction is carried out 
at temperatures between -10.degree. C. and +200.degree. C., preferably 
between -5.degree. C. and +150.degree. C., particularly preferably at 
0.degree. C. to 100.degree. C. It can in principle be carried out under 
normal pressure, but also under increased or reduced pressure. The 
reaction is preferably carried out under normal pressure or under 
pressures of up to 15 bar. At higher temperatures, it is advantageous to 
carry out the reaction under increased pressure, if appropriate also above 
15 bar. 
For carrying out process 5c according to the invention, in general 0.5 to 
2.0 mol, preferably 0.5 to 1.5 mol, of epoxide are employed per mol of 
compound of the formula (Id). 
When the reaction is complete, the reaction solution is washed and the 
organic phase is separated off, dried and concentrated in vacuo. The 
products obtained can be purified in the customary manner by 
recrystallization, vacuum distillation or column chromatography (cf. also 
the Preparation examples). 
If 7-methyl-1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dimethyl-6H-pyrrolo[3',4':4,5]furo[ 
3,2-b]pyridine-6,8(7H)dione is employed as compounds of the general formula 
(Id) and allyl chloroformate is employed as compounds of the general 
formula (VII) in process 5d for the preparation of the novel 1, 2, 3, 4, 
4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Ib), the process can be represented by 
the following equation: 
##STR176## 
Formula (Id) provides a general definition of the 1, 2, 3, 4, 4a.alpha., 
5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo[3',4':4,5]furo[3 
,2-b]pyridine-6,8(7H)-diones required as starting substances for carrying 
out process 5d according to the invention. In this formula, R.sup.1, 
R.sup.2, R.sup.3 and R.sup.4 preferably represent those radicals which 
have already been mentioned as preferred for these substituents in 
connection with the description of the substances of the general formula 
(Ib) according to the invention. 
The 1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo-[3',4':4,5]furo[ 
3,2-b]pyridine-6,8(7H)-diones of the general formula (Id) used as starting 
materials are novel and can be obtained from the 4a, 5a, 8a, 
8b-tetrahydro-3,4a-dialkyl-6H-pyrrolo [3', 4':4,5]furo 
[3,2-b]pyridine-6,8(7H)-dione derivatives (Ia) by the hydrogenation 
process described above. 
Formula (X) provides a general definition of the compounds furthermore to 
be used as starting substances for carrying out process 5d according to 
the invention. 
In the formula (VII), G, X, Y, and W have the meaning which have already 
been mentioned as preferred for these substituents in connection with the 
description of the substances of the general formula (Ib) according to the 
invention. 
The compounds of the formula (X) are generally known compounds of organic 
chemistry, and they can be obtained in some cases commercially or by 
methods known from the literature (for example: persubstituted allophanic 
acid halides: DE-A 2 008 116; carbamoyl chlorides: Liebigs Ann. 299, page 
85; carbamates: Houben-Weyl, Methoden der organischen Chemie [Methods of 
organic chemistry], Volume E 4). 
The reaction of the compounds (Id) with (X) is preferably carried out in 
the presence of a basic reaction auxiliary using diluents. 
Diluents which are used for carrying out process 5d according to the 
invention are the inert, aprotic solvents mentioned for process 3a, such 
as, for example, dioxane, acetonitrile or tetrahydrofuran, but also 
halogenohydrocarbons, in particular chlorohydrocarbons, such as methylene 
chloride. 
All the acid-binding agents mentioned for process 5a can be used as basic 
reaction auxiiliaries for carrying out process 5d according to the 
invention, but preferably tertiary amines, in particular trialkylamines, 
such as triethylamine, N,N-diisopropylethylamine, 
N-propyl-diisopropylamine, N,N'-dimethylcyclohexylamine or 
N-methylmorpholine. 
Process 5d is carried out by reacting compounds of the general formula (Id) 
with compounds of the general formula (X) in the presence of a basic 
reaction auxiliary in one of the diluents mentioned. 
The duration of the reaction is 4 to 72 hours. The reaction is carried out 
at temperatures between -10.degree. C. and +150.degree. C., preferably 
between -5.degree. C. and +80.degree. C., particularly preferably at 
0.degree. C. to room temperature. It is carried out under normal pressure. 
For carrying out process 5b according to the invention, in general 1.0 to 
3.0 mol, preferably 1.0 to 1.5 mol, of acylating agent are employed per 
mol of compound of the formula (Id). 
When the reaction is complete, the reaction solution is washed and the 
organic phase is separated off, dried and concentrated in vacuo. The 
products obtained can be purified in the customary manner by 
recrystallization, vacuum distillation or column chromatography (cf. also 
the Preparation examples). 
In the compounds prepared by process 5d with a halogenoacyl (G=X for 
carbonyl) or halogenosulfonyl radical (G=X for sulfonyl), the halogen 
radical can be replaced by customary processes in a subsequent reaction 
with suitable nucleophiles of the general formula (XVIII) (R.sup.11 -YH), 
for example with amino, hydroxy or mercapto compounds. 
##STR177## 
The exchange of halogen is usually carried out here in the presence of 
basic reaction auxiliaries under the reaction conditions customary for 
this reaction, and if appropriate can be accelerated by means of catalysts 
(cf. also the Preparation examples). 
If 7-methyl-1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dimethyl-6H-pyrrolo[3',4':4,5]furo[ 
3,2-b]pyridine-6,8(7H)dione or 7-methyl-1, 2, 4a.alpha., 5a.alpha., 
8a.alpha., 
8b.alpha.-(.+-.)-hexahydro-3,4a-dimethyl-6H-pyrrolo[3',4':4,5]furo[3,2-b]p 
yridine-6,8(7H)dione is employed as compounds of the general formulae (Id) 
and (Ie) and diglycolic anhydride is employed as carboxylic acid anhydride 
of the general formula (XI) in process 5e for the preparation of the novel 
1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione and/or 
1, 2, 4a, 5a, 8a, 
8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formulae (Ib) and (Ie), the process can be 
represented by the following equations: 
##STR178## 
Formula (Id) and (Ie) provide a general definition of the 1, 2, 3, 4, 
4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo[3',4':4,5]furo[3 
,2-b]pyridine-6,8(7H)-dione and 1, 2, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-hexahydro-3,4a-dialkyl-6H-pyrrolo-[3',4':4,5]furo[3,2-b]p 
yridine-6,8(7H)dione required as starting substances for carrying out 
process 5e according to the invention. In these formulae, R.sup.1, 
R.sup.2, R.sup.3 and R.sup.4 pre-ferably represent those radicals which 
have already been mentioned as preferred for these substituents in 
connection with the description of the substances of the general formulae 
(Ib) and (Ic) according to the invention. 
The 1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo-[3',4':4,5]furo[ 
3,2-b]pyridine-6,8(7H)-diones and 1, 2, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-hexahydro-3,4a-dialkyl-6H-pyrrolo[3',4':4,5]furo[3,2-b]py 
ridine-6,8(7H)dione of the general formulae (Id) and (Ie) used as starting 
materials are novel and can be obtained from the 4a, 5a, 8a, 
8b-tetrahydro-3,4-dialkyl-6H-pyrrolo[3'4':4,5]furo-[3,2-b]pyridine-6,8(7H) 
-dione derivatives (Ia) by the hydrogenation processes described above. 
Formula (XI) provides a general definition of the carboxylic acid 
anhydrides furthermore to be used as starting substances for carrying out 
process 5e according to the invention. 
In the formula (XI), Q has the meaning which have already been mentioned as 
preferred for these substituents in connection with the description of the 
substances of the general formula (Ib) according to the invention. 
The carboxylic anhydrides of the formula (XI) are generally known compounds 
of organic chemistry, and they can be obtained in some cases commercially 
or by methods known from the literature (for example: Houben-Weyl, 
Methoden der organischen Chemie [Methods of organic chemistry], Volume 
VII/4, page 120; Volume VIII, page 477). 
The reaction of the compounds (Id) and/or (Ie) with (XI) is carried out, if 
appropriate, in the presence of a reaction auxiliary using diluents. 
Diluents which are used for carrying out process 5e according to the 
invention are the inert, aprotic solvents mentioned for process 3a, such 
as, for example, ethers, in particular methyl tert-butyl ether, 
tetrahydrofuran or dioxane. 
All the acid-binding agents mentioned for process 5a can be used as 
reaction auxiliaries employed, if appropriate, for carrying out process 5e 
according to the invention, but preferably tertiary amines, in particular 
trialkylamines, such as triethylamine, N,N-diisopropylethylamine, 
N-propyl-diisopropylamine, N,N'-dimethyl-cyclohexylamine or 
N-methylmorpholine. 
Process 5e is carried out by reacting compounds of the general formulae 
(Id) and/or (Ie) with a carboxylic acid anhydride of the general formula 
(XI) in, if appropriate, the presence of a catalyst in one of the diluents 
mentioned. 
Possible catalysts here are not only the basic reaction auxiliaries 
mentioned for process 5a but also acid catalysts. Practically all the 
mineral acids or Lewis acids may be mentioned as such catalysts. The 
mineral acids include include, preferably, hydrogen halide acids, such as 
hydrofluoric acid, hydrobromic acid or hydroiodic acid, and sulfuric acid, 
phosphoric acid, phosphorus acid, nitric acid, and the Lewis acids 
include, preferably, aluminum chloride, boron trifluoride or its etherate, 
titanium(IV) chloride, tin(IV) chloride. 
The duration of the reaction is 4 to 72 hours. The reaction is carried out 
at temperatures between -10.degree. C. and +250.degree. C., preferably 
between -5.degree. C. and +200.degree. C., particularly preferably at 
0.degree. C. to 150.degree. C. It is carried out under normal pressure. 
For carrying out process 5e according to the invention, in general 1.0 to 
3.0 mol, preferably 1.0 to 1.5 mol, of carboxylic acid anhydride are 
employed per mol of compounds of the formulae (Id) and/or (Ie). 
Alternatively, process 5e can also be carried out with excess carboxylic 
acid anhydride of the formula (XI) without a diluent, if the reaction 
mixture remains readily stirrable. 
When the reaction is complete, the reaction solution is washed and the 
organic phase is separated off, dried and concentrated in vacuo. The 
products obtained can be purified in the customary manner by 
recrystallization, vacuum distillation or column chromatography (cf. also 
the Preparation examples). 
If 7-methyl-1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dimethyl-6H-pyrrolo[3',4':4,5]furo[ 
3,2-b]pyridine-6,8(7H)dione is employed as compounds of the general formula 
(Id) and N-benzyl-oxycarbonylsarcosine (Z-Sar-OH) is employed as amino 
acid derivatives of the general formula (XII) in process 5f for the 
preparation of the novel 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]-pyridine-6,8(7H)-dione 
derivatives of the general formula (Ib), the process can be represented by 
the following equation: 
##STR179## 
Formula (Id) provides a general definition of the 1, 2, 3, 4, 4a.alpha., 
5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo[3',4':4,5]furo[3 
,2-b]pyridine-6,8(7H)-diones required as starting substances for carrying 
out process 5f according to the invention. In this formula, R.sup.1, 
R.sup.2, R.sup.3 and R.sup.4 preferably represent those radicals which 
have already been mentioned as preferred for these substituents in 
connection with the description of the substances of the general formula 
(Ib) according to the invention. 
The 1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo-[3',4':4,5]furo[ 
3,2-b]pyridine-6,8(7H)diones of the general formula (Id) used as starting 
materials are novel and can be obtained from the 4a, 5a, 8a, 
8b-tetrahydro-3,4a-dialkyl-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H 
)-dione derivatives (Ia) by the hydrogenation process described above. 
Formula (XII) provides a general definition of the amino acid derivatives 
furthermore to be used as starting substances for carrying out process 5f 
according to the invention. 
In the formula (XII), G, Q, X, R.sup.6, R.sup.7 and R.sup.8 have the 
meaning which have already been mentioned as preferred for this 
substituent in connection with the description of the substances of the 
general formula (Ib) according to the invention. 
The naturally occurring or synthetic amino acids used as starting 
substances can be in the (S) or (R) form (or L or D form), if they are 
chiral. 
Examples which may be mentioned are: 
Aad, Abu, jAbu, ABz, 2ABz, .epsilon.Aca, Ach, Acp, Adpd, Ahb, Aib, 
.beta.Aib, Ala, .beta.Ala, .DELTA.AIa, Alg, All, Ama, Amt, Ape, Apm, Apr, 
Arg, Asn, Asp, Asu, Aze, Azi, Bai, Bph, Can, Cit, Cys, (Cys).sub.2, Cyta, 
Daad, Dab, Dadd, Dap, Dapm, Dasu, Djen, Dpa, Dtc, Fel, Gln, Glu, Gly, Guv, 
hAla, hArg, hCys, hGln, hGlu, His, hIle, hLeu, hLys, hMet, hPhe, hPro, 
hSer, hThr, hTrp, hTyr, HyI, Hyp, 3Hyp, Ile, Ise, Iva, Kyn, Lant, Lcn, 
Leu, Lsg, Lys, .beta.Lys, .DELTA.Lys, Met, Mim, Min, nArg, Nle, Nva, Oly, 
Orn, Pan, Pec, Pen, Phe, Phg, Pic, Pro, .DELTA.Pro, Pse, Pse, Pya, Pyr, 
Pza, Qin, Ros, Sar, Sec, Sem, Ser, Thi, .beta.Thi, Thr, Thy, Thx, Tia, 
Tle, Tly, Trp, Trta, Tyr, Val, Nal, Tbg, Npg, Chg, Thia (cf. for example, 
Houben-Weyl, Methoden der Organischen Chemie, [Methods of organic 
chemistry], Volume XV/1 and 2, Stuttgart, 1974). 
The compounds of the formula (XII) can be obtained in some cases 
commercially or by methods known from the literature (cf., for example: 
N-methylamino acids: 
R. Bowmann et al. J. Chem. Soc. (1950) page 1346; J. R. McDermott et al Can 
J. Chem. 51 (1973) page 1915; H. Wurziger et al. Kontakte (Merck, 
Darmstadt) 3 (1987) page 8). 
The reaction of the 1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,,4a-dialkyl-6H-pyrrolo[3',4':4,5]furo[ 
3,2-b]pyridine-6,8(7H)-diones of the general formula (Ic) with amino acid 
derivatives of the formula (XII) is preferably carried out in the presence 
of coupling reagents and in the presence of a basic reaction auxiliary 
using diluents. 
Coupling reagents which are used for carrying out process 5f are all those 
which are suitable for establishing an amide bond (cf., for example: 
Houben-Weyl, Methoden der organischen Chemie [Methods of organic 
chemistry], Volume 15/2; Bodanszky et al., Peptide Synthesis 2nd ed. 
(Wiley & Sons, New York 1976) or Gross, Meienhofer, The Peptides: Analysis 
Synthesis, Biology (Academic Press, New York 1979). The following methods 
are preferably used: active ester method with pentachloro- (Pcp) and 
pentafluorophenyl (Pfp), N-hydroxysuccinimide, N-hydroxy-5-norbonene-2,3 
-dicarbox-amide (HONB), 1-hydroxy-benzotriazole (HOBt) or 
3-hydroxy-4-oxo-3,4-dihydro- 1,2,3-benzotriazine as the alcohol component, 
coupling with carbodiimides, such as dicyclo-hexyl-carbodiimide (DCC) by 
the DCC additive process, or with n-propanephos-phonic anhydride (PPA) and 
the mixed anhydride method with pivaloylchloride, ethyl (EEDQ) and 
isobutyl chloroformate (IIDQ) or coupling with phosphonium reagents, such 
as benzotriazol-1-yl-oxy-tris(dimethylamino-phosphonium) 
hexafluorophosphate (BOP), bis(2-oxo-3-oxazolidinyl)phosphonium acid 
chloride (BOP-Cl), or with phosphonic acid ester reagents, such as diethyl 
cyanophosphonate (DEPC) and diphenylphosphoryl azide (DPPA) or uronium 
reagents, such as 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetra-methyluronium 
tetrafluoro-borate (TBTU). 
Coupling with phosphonium reagents such as 
bis(2-oxo-3-oxazolidinyl)-phosphonium acid chloride (BOP-Cl), 
benzotriazol-1-yl-oxy-tris(dimethylamino-phosphonium) hexafluorophosphate 
(BOP) and phosphonic acid ester reagents, such as diethyl cyanophosphonate 
(DEPC) or diphenylphosphoryl azide (DPPA) is preferred. 
All acid-binding agents suitable for process 5a can likewise be employed as 
basic reaction auxiliaries for carrying out process 5f according to the 
invention. 
Tertiary amines, in particular trialkylamines, such as triethylamine, 
N,N-diisopropylethylamine, N-propyl-diisopropylamine, 
N,N'-dimethyl-cyclohexylamine or N-methylmorpholine are preferably 
suitable. 
Diluents which are used for carrying out process 5f according to the 
invention are the solvents mentioned for process 3a, such as, for example, 
halogenohydrocarbons, in particular chlorohydrocarbons, such as methylene 
chloride or 1,2-dichloroethane, and mixtures of these with other mentioned 
diluents. 
Process 5f is in general carried out in such a way by compounds of the 
formula (Id) with compounds of the general formula (XII) in the presence 
of one of the coupling reagents mentioned and in the presence of one of 
the basic reaction auxiliaries mentioned in one of the diluents mentioned. 
The duration of the reaction is 4 to 72 hours. The reaction is carried out 
at temperatures between -10.degree. C. and +120.degree. C., preferably 
between -5.degree. C. and +50.degree. C., particularly preferably at 
0.degree. C. to room temperature. It is carried out under normal pressure. 
For carrying out process 5f according to the invention, in general 1.0 to 
3.0 mol, preferably 1.0 to 1.5 mol of coupling reagent are employed per 
mol of 1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo-[3',4':4,5]furo[ 
3,2-b] pyridine-6,8(7H)-diones of the formula (Id). 
When the reaction is complete, the reaction solution is washed and the 
organic phase is separated off, dried and concentrated in vacuo. The 
products obtained can be purified in the customary manner by 
recrystallization, vacuum distillation or column chromatography (cf. also 
the Preparation examples). 
If 7-methyl-1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)octahydro-3.alpha.,4a-dimethyl-6H-pyrrolo-[3',4':4,5]furo[ 
3,2-b]pyri-dine-6,8(7H)dione is employed as compounds of the general 
formula (Id) and trichloroacetyl isocyanate is employed as compounds of 
the general formula (XIII) in process 5g for the preparation of the of the 
novel 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Ib), the process can be represented by 
the following equation: 
##STR180## 
Formula (Id) provides a general definition of the 1, 2, 3, 4, 4a.alpha., 
5a.alpha., 8a.alpha., 8b.alpha.-(.+-.)-octahydro-3.alpha., 
4a-dialkyl-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-diones 
required as starting substances for carrying out process 5g according to 
the invention. In this formula, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 
preferably represent those radicals which have already been mentioned as 
preferred for these substituents in connection with the description of the 
substances of the general formula (Ib) according to the invention. 
The 1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3a.alpha., 
4a-dialkyl-6H-pyrrolo-[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-diones of the 
general formula (Id) used as starting materials are novel and can be 
obtained from the 4a, 5a, 8a, 8b-tetrahydro-3,4a-dialkyl-6H-pyrrolo[3',4 
':4,5]furo[3,2-b]pyridine-6,8(7H)-dione derivatives (Ia) by the 
hydrogenation process described above. 
Formulae (XIII) and (XIV) provide general definitions of the compounds 
furthermore to be used as starting substances for carrying out the process 
5g according to the invention. 
In the formulae (XIII) and (XIV), R.sup.11, Y, G.sup.1, X.sup.1 and X have 
the meaning which have already been mentioned as preferred for these 
substituents in connection with the description of the substances of the 
general formula (Ib) according to the invention. 
The compounds of the formulae (XIII) and (XIV) are generally known 
compounds of organic chemistry, and can be obtained in some cases 
commercially or by methods known from the literature (Houben-Weyl, 
Methoden der organischen Chemie [Methods of organic chemistry], Volume E 
4). 
The reaction of the compounds (Id) with (XIII) or (XIV) by process 5f 
according to the invention is preferably carried out in the presence of 
diluents, if appropriate in the presence of a basic reaction auxiliary. 
Diluents which are used for carrying out process 5g according to the 
invention are the solvents mentioned for process 3a, such as, for example, 
nitrites, such as acetonitrile, propionitrile, butyronitrile, in 
particular acetonitrile, and ethers, such as ethylpropyl ether, n-butyl 
ether, diethyl ether, dipropyl esther, diisopropyl ether, di-n-butyl 
ether, diisobutyl ether, diisoamyl ether, tetrahydrofuran, dioxane, in 
particular tetrahydrofuran and dioxane. 
Process 5g can also be carried out in the presence of basic reaction 
auxiliaries. All the acid-binding agents mentioned for process 5a can be 
used as such basic reaction auxiliaries for carrying out process 5g 
according to the invention, but preferably tertiary amines, in particular 
trialkylamines, such as triethylamine, N,N-diisopropylethylamine or 
N-methylmorpholine, and amidine bases or guanidine bases, such as 
diazabicyclo-(4.3.0)nonene (DBN), diazabicyclo (2.2.2)-octane (DABCO), 
1,8-diaza-bicyclo(5.4.0)-undecene (DBU) in particular 
1,8-diazabicyclo(5.4.0)-undecene (DBU). 
Process 5g is carried out by bringing together compounds of the general 
formula (Id) with equimolar amounts of a compound of the formulae (XIII) 
or (XIV) in one of the diluents mentioned above, if appropriate in the 
presence of a basic, reaction auxiliary. The duration of the reaction is 1 
to 72 hours. The reaction is carried out at temperatures between 
-50.degree. C. to +200.degree. C., preferably in a temperature range 
between -20.degree. C. and +150.degree. C., in particular in a temperature 
range between -10.degree. C. and +120.degree. C. 
The reaction can in principle be carried out under normal pressure, but it 
can also be carried out under increased or reduced pressure. It is 
preferably carried out under normal pressure or under pressures of up to 
15 bar. At higher temperatures, it is advantageous to carry out the 
reaction under increased pressure, if appropriate also above 15 bar. 
When the reaction is complete, the reaction mixture is worked up by 
generally customary methods (cf. also the Preparation examples). 
Processes for the preparation of organic carbamates from an amine giving a 
basic reaction, carbon dioxide and an alkylating agent in the presence of 
basic alkali metal, alkaline earth metal or ammonium salts are known (cf. 
EP-A 511 948, EP-A 628 542 and literature cited therein). 
It has now been found that the basic 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione and/or 
1, 2, 4a, 5a, 8a, 
8b-hexahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formulae (Id) and (Ie) according to the 
invention also react, as secondary amino compounds, with carbon dioxide 
and an alkylating agent in the presence of metal carbonates to give 
carbamates of the general formula (Ib) and (Ic). 
If 7-methyl-1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha., 
4a-dimethyl-6H-pyrrolo-[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione, is 
employed as compounds of the general formula (Id), carbon dioxide and 
potassium carbonate are employed, and propargyl bromide is employed as 
compounds of the general formula (VIIa) in process 5h for the preparation 
of the novel 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)dione 
derivatives of the general formula (Ib), the process can be represented by 
the following equation: 
##STR181## 
The 1, 2, 3, 4, 4a, 5a, 8a, 8b-octahydro-6H-pyrrolo[3', 4':4,5] 
furo[3,2-b]pyridine-6,8(7H)-dione derivatives of the general formula (Id) 
in which the radicals R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the 
preferred and particularly preferred meanings in the case of the compounds 
of the general formula (Ib) are preferably employed in process 5h. 
The 1, 2, 3, 4, 4a.alpha., 5a.alpha., 8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dialkyl-6H-pyrrolo[3',4':4,5]furo[3 
,2-b]pyridine-6,8(7H)-diones of the general formula (Id) used as starting 
materials are novel and can be obtained from the 4a, 5a, 8a, 
8b-tetrahydro-3,4-dialkyl-6H-pyrrolo[3',4':4,5]furo 
[3,2-b]pyridine-6,8(7H)-dione derivatives (Ia) by the hydrogenation 
process described above. 
The usual commercial product, if appropriate also so-called "dry ice", can 
be employed as carbon dioxide in the process according to the invention. 
The alkylating agents of the formula (VIIa) furthermore to be used as 
starting substances for carrying out process 5h according to the invention 
are generally known compounds of organic chemistry. 
In the formula (VIIa), R.sup.11 has the meaning which has already been 
mentioned as preferred for this substituent in connection with the 
description of the substances of the general formula (Ib) according to the 
invention, and Hal has the meaning of an electron-withdrawing leaving 
group. 
Suitable leaving groups are, for example, halogen, such as fluorine, 
chlorine, bromine and iodine, sulfonate, such as aryl- and 
perfluoroalkylsulfonate, monosubstituted diazo and monosubstituted 
nitrato, and those additionally listed in J. March, Advanced Organic 
Chemistry, 3rd ed., John Wiley & Sons, New York 1985, pages 310-316. 
Compounds which give a basic reaction and can be used in the present 
invention are one or more basic compounds of the elements lithium, sodium, 
magnesium, potassium, calcium, rubidium, strontium, cesium, barium, and/or 
of ammonium. Possible basic compounds are, for example, salts, oxides, 
hydrides and hydroxides which give a basic reaction. Examples which may be 
mentioned are: lithium hydride, sodium hydride, potassium hydride, calcium 
hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, 
rubidium hydroxide, magnesium hydroxide, calcium hydroxide, strontium 
hydroxide, barium hydroxide, lithium oxide, sodium peroxide, potassium 
oxide, potassium peroxide, calcium oxide, barium oxide, magnesium oxide, 
strontium oxide, lithium carbonate, lithium bicarbonate, rubidium 
carbonate, rubidium bicarbonate, cesium bicarbonate, cesium carbonate, 
lithium cyanide, sodium cyanide, potassium cyanide, rubidium cyanide, 
ammonium bicarbonate, cesium carbonate, ammoni-um carbamate, potassium 
sulfide, potassium hydrogensulfide, sodium sulfide, sodium hydrogensulfide 
and/or naturally occurring or synthetically obtainable mixtures thereof, 
such as, for example, dolomite or magnesium oxide carbonate and/or 
compounds which contain sodium or potassium metal on the corresponding 
carbonates in dispersed form. 
However, alkali metal carbonates and/or bicarbonates, especially preferably 
cesium carbonate or potassium carbonate, are preferred. 
The compounds which give a basic reaction can be employed in anhydrous form 
or, if they are salts which crystallize with water of hydration, in 
hydrated form. Preferably, however, anhydrous compounds are used. 
Diluents which are used for carrying out process 5h according to the 
invention are the solvents mentioned for process 3a, such as, for example, 
amides, such as hexamethylenephosphorotriamide, N,N-dimethylformamide, 
N,N-dipropylformamide, N,N-dibutylformamide, N-methyl-pyrrolidone or 
N-methyl-caprolactam, in particular N,N-dialkylformamides, such as 
N,N-dimethyl-formamide, and sulfoxides, such as dimethyl sulfoxide, 
tetramethylene sulfoxide, dipropyl sulfoxide, benzylmethyl sulfoxide, 
diusobutyl sulfoxide, dibutyl sulfoxide, diisoamyl sulfoxide, in 
particular dimethyl sulfoxide. 
Alternatively, process 5h can also be carried out in the presence of basic 
reaction auxiliaries, i.e. in the presence of further bases, for example 
in an amount of less than 0.5 mol, based on the base employed. 
All the acid-binding agents mentioned for process 5a can as such basic 
reaction auxiliaries for carrying out process 5h according to the 
invention, but preferably tertiary amines, in particular trialkylamines, 
such as triethylamine, N,N-diisopropylethylamine or N-methylmorpholine, 
and amidine bases or guanidine bases, such as 
7-methyl-1,5,7-triazabicyclo-(4.4.0)dec-5-ene (MTBD); 
diazabicyclo-(4.3.0)nonene (DBN), diazabicyclo-(2.2.2)octane (DABCO), 
1,8-diazabi-cyclo(5.4.0)-undecene (DBU) cyclohexyltetrabutylguanidine 
(CyTBG), cyclohexyltetramethylguanidine (CyTMG), 
cyclohexyltetrabutylguanidine, 
N,N,N,N-tetra-methyl-1,8-naphthalenediamine, in particular 
cyclohexyltetra-methylguanidine (CyTMG) and cyclohexyltetrabutylguanidine 
(CyTBG), use. 
Process 5h is carried out by bringing together compounds of the general 
formula (Id) in the presence of carbon dioxide, a 2- to 3-fold excess of 
alkali metal carbonate of the formula (XV) and an alkylating agent of the 
formula (VIIa) in one of the diluents mentioned above for process 3a, if 
appropriate in the presence of a basic reaction auxiliary, at room 
temperature. In a second reaction step, the alkylation of the alkali metal 
salts of the formulae (XVI) and (XVII), formed in situ, with compounds of 
the formula (VIIa) is carried out over a reaction time of 1 to 72 hours 
and a reaction temperature between -50.degree. C. and +180.degree. C., 
preferred temperatures being in the range between -30.degree. C. and 
+150.degree. C., in particular those in the range of -10.degree. C. to 
+100.degree. C. 
The reaction can in principle be carried out under normal pressure, but it 
can also be carried out under increased or reduced pressure. Preferably, 
it is carried out under normal pressure or under pressures of up to 15 
bar. At higher temperatures it is advantageous to carry out the reaction 
under increased pressure, if appropriate also above 15 bar. 
The reaction products are worked up and isolated by generally customary 
methods (cf. also the Preparation examples). 
If 1-(4-nitrophenoxy-carbonyl)-7-methyl-1, 2, 3, 4, 4a.alpha., 5a.alpha., 
8a.alpha., 
8b.alpha.-(.+-.)-octahydro-3.alpha.,4a-dimethyl-6H-pyrrolo[3',4':4,5]furo[ 
3,2-b] pyridine-6,8(7H)-dione is employed as compounds of the general 
formula (If) and morpholine is employed as the nucleophile of the general 
formula (XVIII) in process 5i for the preparation of the novel 1, 2, 3, 4, 
4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (Ib), the process can be represented by 
the following equation: 
##STR182## 
The general formula (If) provides a general definition of the 1, 2, 3, 4, 
4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives required as starting substances for carrying out process 5i 
according to the invention. In this formula, R.sup.1, R.sup.2, R.sup.3, 
R.sup.4, R.sup.5, G, W and X preferably represent those radicals which 
have already been mentioned as preferred for these substituents in 
connection with the description of the substances of the general formula 
(If) according to the invention. 
The 1, 2, 3, 4, 4a, 5a, 8a, 
8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione 
derivatives of the general formula (If) used as starting materials can be 
prepared by process 5d according to the invention already described above. 
The nucleophilic agents of the formula (XVIII) furthermore to be used as 
starting substances for carrying out process 5i according to the invention 
are generally known compounds of organic chemistry, and they can be 
obtained in some cases commercially. In the formula (XVIII), R.sup.11 and 
Y have the meaning which have already been mentioned as preferred in 
connection with the description of the substances of the general formula 
(Ib) according to the invention. 
Process 5i is carried out by reacting compounds of the general formula (If) 
in the presence of a nucleophilic agent of the formula (XVIII) in one of 
the diluents mentioned above. The duration of the reaction is 4 to 72 
hours. The reaction is carried out at temperatures between +10.degree. C. 
and +200.degree. C., preferably between +20.degree. C. and +150.degree. 
C., particularly preferably at the boiling point of the diluent. 
The reaction can in principle be carried out under normal pressure, but it 
can also be carried out under increased or reduced pressure. It is 
preferably carried out under normal pressure or under pressures of up to 
15 bar. At higher temperatures, it is advantageous to carry out the 
reaction under increased pressure, if appropriate also above 15 bar. 
When the reaction is complete, the reaction solution is washed and the 
organic phase is separated off, dried and concentrated in vacuo. The 
products obtained can be purified in the customary manner by 
recrystallization, vacuum distillation or column chromatography (cf. also 
the Preparation examples). 
Compounds according to the invention are obtainable with processes 5a to 5i 
according to the invention from the individual units with both the (S) and 
the (R) configuration (or L and D configuration), retaining the original 
configuration of the starting substances. 
The "inert solvents" referred to in the above process variants 5a to 5i are 
taken in each case to mean solvents which are inert under the particular 
reaction conditions, but do not have to be inert under any desired 
reaction conditions. 
The active compounds are suitable for controlling pathogenic endoparasites 
which occur in humans and in stock, breeding, zoo, laboratory and test 
animals and pets in animal husbandry and animal breeding, having favorable 
toxicity to warm-blooded animals. They are active here against all or 
individual stages of development of the pests and against resistant and 
normally sensitive species. By controlling the pathogenic endoparasites, 
disease, fatalities and reductions in productivity (for example in the 
production of meat, milk, wool, hides, eggs, honey and the like) are to be 
diminished, so that more economic and easier animal husbandry is possible 
by use of the active compounds. The pathogenic endoparasites include 
cestodes, trematodes, nematodes, acantocephalae, in particular: 
From the order of the Pseudophyllidea, for example: Diphyllobothrium spp., 
Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., 
Diphlogonoporus spp.. 
From the order of the Cyclophyllidea, for example: Mesocestoides spp., 
Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomsa 
spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., 
Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera 
spp., Davainea spp, Raillietina spp., Hymenolepis spp., Echinolepis spp., 
Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., 
Diplopylidium spp.. 
From the subclass of the Monogenea, for example: Gyrodactylus spp., 
Dactylogyrus spp., Polystoma spp.. 
From the subclass of the Digenea, for example: Diplostomum spp., 
Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., 
Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., 
Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium 
spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides 
spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., 
Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle 
spp., Fischoederius spp., Gastrothylacus spp., Notocotylus spp., 
Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., 
Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., 
Nanophyetus spp., Opisthorchis spp., Clonorchis spp., Metorchis spp., 
Heterophyes spp., Metagonismus spp.. 
From the order of the Enoplida, for example: Trichuris spp., Capillaria 
spp., Trichomosoides spp., Trichinella spp. 
From the order of the Rhabditia, for example: Micronema spp., Strongyloides 
spp.. 
From the order of the Strongylida, for example: Stronylus spp., 
Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus 
spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., 
Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus 
spp., Ancylostoma spp., Uncinaria spp., Bunostomum spp., Globocephalus 
spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus 
spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., 
Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., 
Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., 
Paracrenosoma spp., Angiostrongylus spp., Aelurostrongylus spp., 
Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus 
spp., Ostertagia spp., Marshallagia spp., Cooperia spp., Nematodirus spp., 
Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.. 
From the order of the Oxyurida, for example: Oxyuris spp., Enterobius spp., 
Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.. 
From the order of the Ascaridia, for example: Ascaris spp., Toxascaris 
spp., Toxocara spp., Parascaris spp., Anisakis spp., Ascaridia spp.. 
From the order of the Spirurida, for example: Gnathostoma spp., 
Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., 
Parabronema spp., Draschia spp., Dracunculus spp.. 
From the order of the Filariida, for example: Stephanofilaria spp., 
Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides 
spp., Brugia spp., Wuchereria spp., Onchocerca spp. 
From the order of the Gigantorhynchida, for example: Filicollis spp., 
Moniliformis spp., Macracanthorhynchus spp., Prosthenorchis spp.. 
The stock and breeding animals include mammals, such as, for example, 
cattle, horses, sheep, pigs, goats, camels, water buffalo, donkeys, 
rabbits, fallow deer, reindeer, fur-bearing animals, such as, for example, 
mink, chinchillas, racoons, birds, such as, for example, chickens, geese, 
turkeys, ducks, fresh water and salt-water fishes, such as, for example, 
trout, carp, eels, reptiles, insects, such as, for example, honey bees and 
silk worms. 
Laboratory and test animals include mice, rats, guinea-pigs, golden 
hamsters, dogs and cats. 
Pets include dogs and cats. 
The compounds can be used both prophylactically and therapeutically. 
The active compounds are used, directly or in the form of suitable 
formulations, enterally, parenterally, dermally, nasally, by treatment of 
the environment or with the aid of molded articles containing the active 
compound, such as, for example, strips, sheets, tapes, collars, ear marks, 
limb tapes, marking devices. 
Enteral use of the active compounds is effected, for example, orally, in 
the form of powders, tablets, capsules, pastes, drinks, granules, orally 
administerable solutions, suspensions and emulsions, boli, medicated feed 
or drinking water. Dermal use is effected, for example, in the form of 
dips, sprays or pour-on and spot-on formulations. Parenteral use is 
effected, for example, in the form of injection (intramuscular, 
subcutaneous, intravenous, intraperitoneal) or by implants. 
Suitable formulations are: 
Solutions, such as injection solutions, oral solutions, concentrates for 
oral administration after dilution, solutions for use on the skin or in 
body cavities, pour-on formulations, gels; 
emulsions and suspensions for oral or dermal use and for injection; 
semi-solid formulations; 
formulations in which the active compound is processed in an ointment base 
or in an oil-in-water or water-in-oil emulsion base; 
Solid formulations, such as powders, premixes or concentrates, granules, 
pellets, tablets, boli, capsules; aerosols and inhalates, molded articles 
containing the active compound. 
Injection solutions are administered intravenously, intramuscularly and 
subcutaneously. 
Injection solutions are prepared by dissolving the active compound in a 
suitable solvent and if necessary adding additives, such as solubilizing 
agents, acids, bases, buffer salts, antioxidants, preservatives. The 
solutions are subjected to sterile filtration and bottled. 
Solvents which may be mentioned are: physiologically tolerated solvents, 
such as water, alcohols, such as ethanol, butanol, benzyl alcohol, 
glycerol, propylene glycol, polyethylene glycols, N-methyl-pyrrolidone, 
and mixtures thereof. 
If appropriate, the active compounds can also be dissolved in 
physiologically tolerated vegetable or synthetic oils which are suitable 
for injection. 
Solubilizing agents which may be mentioned are: solvents which promote 
solution are the active compound in the main solvent or prevent its 
precipitation. Examples are polyvinylpyrrolidone, polyoxyethylated castor 
oil, polyoxyethylated sorbitan esters. 
Preservatives are: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid 
esters, n-butanol. 
Oral solutions are used directly. Concentrates are used orally after prior 
dilution to the use concentration. Oral solutions and concentrates are 
prepared as described above for the injection solutions, but sterile 
working can be omitted. 
Solutions for use on the skin are dripped on, brushed on, massaged in, 
sprinkled on or sprayed on. These solutions are prepared as described 
above for the injection solutions. 
It may be advantageous to add thickeners during the preparation. Thickeners 
are: inorganic thickeners, such as bentonites, colloidal silicic acid, 
aluminum monostearate, organic thickeners, such as cellulose derivatives, 
polyvinyl alcohols and copolymers thereof, acrylates and methacrylates. 
Gels are applied to or spread on the skin or introduced into body cavities. 
Gels are prepared by adding to solutions which have been prepared as 
described for the injection solutions, an amount of thickeners such that a 
clear composition having an ointment-like consistency is formed. The 
thickeners mentioned above are employed as thickeners. 
Pour-on formulations are poured or sprayed on to limited areas of the skin, 
the active compound penetrating through the skin and acting systemically. 
Pour-on formulations are prepared by dissolving, suspending or emulsifying 
the active compound in suitable solvents or solvent mixtures tolerated by 
the skin. If appropriate, further auxiliaries, such as colorants, 
absorption-promoting substances, antioxidants, light stabilizers, 
adhesives, are added. 
Solvents which may be mentioned are: water, alkanols, glycols, polyethylene 
glycols, polypropylene glycols, glycerol, aromatic alcohols, such as 
benzyl alcohol, phenylethanol, phenoxyethanol, esters, such as ethyl 
acetate, butyl acetate, benzyl benzoate, ethers, such as alkylene glycol 
alkyl ethers, such as dipropylene glycol monomethyl ether, diethylene 
glycol mono-butyl ether, ketones, such as acetone, methyl ethyl ketone, 
aromatic and/or aliphatic hydrocarbons, vegetable or synthetic, oils, DMF, 
dimethylacetamide, N-methylpyrrolidone, 
2,2-dimethyl-4-oxymethylene-1,3-dioxolane. 
Colorants are all the colorants which are approved for use on animals and 
can be dissolved or suspended. 
Absorption-promoting substances are, for example, DMSO, spreading oils, 
such as isopropyl myristate, dipropylene glycol pelargonate, silicone 
oils, fatty acid esters, triglycerides, fatty alcohols. 
Antioxidants are sulfites are metabisulfites, such as potassium 
metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, 
tocopherol. 
Light stabilizers are, for example, novantisole acid. 
Adhesives, are for example, cellulose derivatives, starch derivatives, 
polyacrylates, naturally occurring polymers, such as alginates, gelatin. 
Emulsions can be used orally, dermally or as injections. 
Emulsions are either of the water-in-oil type or of the oil-in-water type. 
They are prepared by dissolving the active compound either in the 
hydrophobic oi in the hydrophilic phase and homogenizing this solution 
with the solvent of the other phase with the aid of suitable emulsifiers 
and if appropriate other auxiliaries, such as colorants, 
absorption-promoting substances, preservatives, antioxidants, light 
stabilizers, viscosity-increasing substances. 
Hydrophobic phases (oils) which may be mentioned are: paraffin oils, 
silicone oils, naturally occurring plant oils, such as sesame oil, almond 
oil, castor oil, synthetic triglycerides, such as caprylic/capric acid 
biglyceride, a triglyceride mixture with. plant fatty acids of chain 
length C.sub.8-12 or other specially selected naturally occurring fatty 
acids, partial glyceride mixtures of saturated or unsaturated fatty acids, 
which may also contain hydroxyl groups, mono- and diglycerides of C.sub.8 
/C.sub.10 -fatty acids. 
Fatty acid esters, such as ethylstearate, di-n-butyryl adipate, hexyl 
laurate, dipropylene glycol pelargonate, esters of a branched fatty acid 
of medium chain length with saturated fatty alcohols of chain length 
C.sub.16 -C.sub.18, isopropylmyristate, isopropylpalmitate, 
caprylic/capric acid esters of saturated fatty alcohols of chain length 
C.sub.12 -C.sub.15, isopropylstearate, oleyl oleate, decyl oleate, ethyl 
oleate, ethyl lactate, waxy fatty acid esters, such as synthetic duck 
uropygeal gland fat, dibutyl phthalate, diisopropyl adipate, ester 
mixtures related to the latter and others. 
Fatty alcohols, such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl 
alcohol, oleyl alcohol. 
Fatty acids, such as, for example, oleic acid and its mixtures. 
Hydrophilic phases which may be mentioned are: water, alcohols, such as, 
for example, propylene glycol, glycerol, sorbitol and their mixtures. 
Emulsifiers which may be mentioned are: nonionic surfactants, for example 
polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, 
sorbitan monostearate, glycerol monostearate, polyoxyethylstearate, 
alkylphenol polyglycol ethers; 
ampholytic surfactants, such as di-Na N-lauryl-.beta.-iminodipropionate or 
lecithin; 
anionic surfactants, such as Na lauryl sulfate, fatty alcohol 
ether-sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester 
monoethynolamine salt. 
Further auxiliaries which may be mentioned are: viscosity-increasing and 
emulsion-stabilizing substances, such as carboxymethylcellulose, 
methylcellulose and other cellulose and starch derivatives, polyacrylates, 
alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, 
copolymers of methyl vinyl ether and maleic anhydride, polyethylene 
glycols, waxes, colloidal silicic acid or mixtures of the substances 
listed. 
Suspensions can be used orally, dermally or as an injection. They are 
prepared by suspending the active compound in a carrier liquid, if 
appropriate with the addition of other auxiliaries, such as wetting 
agents, colorants, absorption-promoting substances, preservatives, 
antioxidant light stabilizers. 
Carrier liquids which may be mentioned are all the homogeneous solvents and 
solvent mixtures. 
Wetting agents (dispersing agents) which may be mentioned are the 
surfactants mentioned above. 
Other auxiliaries which may be mentioned are those mentioned above. 
Semi-solid formulations can be administered orally or dermally. They differ 
from the suspensions and emulsions described above only in their higher 
viscosity. 
To prepare solid formulations, the active compound is mixed with suitable 
carrier substances, if appropriate with the addition of auxiliaries, and 
the mixture is brought into the desired shape. 
Carrier substances which may be mentioned are all the physiologically 
tolerated solid inert substances. Inorganic or organic substances serve as 
such inert substances. Inorganic substances are, for example, sodium 
chloride, carbonates, such as calcium carbonate, bicarbonates, aluminum 
oxides, silicic acids, aluminas, precipitated or colloidal silicon 
dioxide, phosphates. 
Organic substances are, for example, sugars, cellulose, foodstuffs and 
feedstuffs, such as milk powder, animal flours, cereal flours and shredded 
cereals, starches. 
Auxiliaries are preservatives, antioxidants, dyestuffs, which have already 
been listed above. 
Other suitable auxiliaries are lubricants and slip agents, such as, for 
example, magnesium stearate, stearic acid, talc, bentonites, substances 
which promote disintegration, such as starch or crosslinked 
polyvinylpyrrolidone, binders, such as, for example, starch, gelatin or 
linear polyvinylpyrrolidone, and dry binders, such as microcrystalline 
cellulose. 
The active compounds can also be present in the formulations as a mixture 
with synergists or with other active compounds which act against 
pathogenic endoparasites. Such active compounds are, for example, 
L-2,3,5,6-tetrahydro-6-phenyl-imidazothiazole, benzimidazole-carbamates, 
prazi-quantel, pyrantel, febantel. 
Ready-to-use formulations comprise the active compound in concentrations of 
1.0 ppm-20 percent by weight, preferably 0.1-10 percent by weight. 
Formulations which are diluted before use comprise the active compound in 
concentrations of 0.5-90% by weight, preferably 5-50% by weight.