4a, 5a, 8a,...

Details 4a, 5a, 8a,... 4a, 5a, 8a,...

2000-05-22

2001-09-18

Rotman, Alan L. (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C546S080000, C546S082000, C546S083000, C546S084000, C544S106000, C544S111000

Reexamination Certificate

active

06291472

ABSTRACT:

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,
in which
R
1
represents hydrogen, straight-chain or branched alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl, heteroarylalkyl, which are optionally substituted,
R
2
represents hydrogen, straight-chain or branched alkyl, cycloalkyl, alkoxycarbonyl, which are optionally substituted,
R
1
and R
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
3
represents hydrogen, straight-chain or branched alkyl, cycloalkyl, alkoxycarbonyl, which are optionally substituted,
R
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
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
1
, G
2
, G
3
and G
4
in which
R
6
represents hydrogen, straight-chain or branched alkyl, cycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, which are optionally substituted,
R
6
and R
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
7
and R
8
independently of one another represent hydrogen, straight-chain or branched alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, which are optionally substituted, or
R
7
and R
8
together represent a spirocyclic ring which is optionally substituted,
 can denote carboxyl, thiocarboxyl, —C═CH—NO
2
, —C═CH—CN, —C═C—R
9
, sulfoxyl, sulfonyl, —P(O)—OR
10
or P(S)—OR
10
,
R
9
represents hydrogen, hydroxyl, alkoxy, alkylcarbonyl, halogenoalkylcarbonyl, alkylsulfonyl, nitro or cyano, and
R
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
5
and G
6
in which
can denote carboxyl, thiocarboxyl or sulfonyl,
Y represents oxygen, sulfur or —NR
12
,
R
11
, in the case where Y represents nitrogen, can denote a cyclic amino group linked via a nitrogen atom,
R
11
and R
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
11
and R
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═, —NR
14
— or by quaternized nitrogen and is optionally substituted,
R
13
represents hydrogen or alkyl,
R
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
2
and the adjacent carbon atom, and/or between the carbon atom and the adjacent nitrogen atom which carry the substituents R
1
and R
5
.
In the case where a double bond is present between the carbon atom which carries the substituent R
1
and the adjacent nitrogen atom with a substituent R
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
in which
R
1
represents hydrogen, straight-chain or branched alkyl having up to 4 carbon atoms, C
3-6
-cycloalkyl, aryl-C
1-2
-alkyl, aryl, heteroaryl, heteroaryl-C
1-2
-alkyl, which are optionally substituted,
R
1
and R
2
, together with the atoms to which they are bonded, represent a 5- or 6-membered ring, which is optionally substituted,
R
2
and R
3
independently of one another represent hydrogen, straight-chain or branched alkyl having up to 4 carbon atoms, halogenoalkyl, hydroxyalkyl, C
1-4
-alkanoyloxyalkyl, C
1-2
-alkoxyalkyl, C
1-2
-mercaptoalkyl, C
1-2
-alkylthioalkyl, C
1-2
alkylsulfinylalkyl, C
1-2
alkylsulfonylalkyl, aminoalkyl, C
1-6
-alkylaminoalkyl, C
1-6
-dialkylaminoalkyl, C
3-6
-cycloalkylaminoalkyl, C
3-6
-cycloalkyl, C
1-4
-alkoxycarbonyl,
R
4
represents hydrogen, straight-chain or branched C
1-6
-alkyl, halogeno-C
1-6
-alkyl, hydroxy-C
1-6
-alkyl, C
1-4
-alkanoyloxyalkyl, C
1-2
-alkoxyalkyl, C
1-4
alkoxycarbonyl-C
1-4
-alkyl, amino-C
1-6
-alkyl, C
1-6
alkylamino-C
1-6
-alkyl, C
1-6
-dialkylamino-C
1-6
alkyl, C
1-6
-trialkylammonium-C
1-6
-alkyl halide, C
2-6
-alkenyl, C
2-6
-alkinyl, C
3-6
-cycloalkyl, C
3-6
-cycloalkyl-C
1-2
-alkyl, aryl, aryl-C
1-2
-alkyl, heteroaryl, heteroaryl-C
1-2
-alkyl, amino, C
1-4
-alkylamino, C
1-4
-dialkylamino, C
3-7
-cycloalkylamino, which are optionally substituted,
R
5
for hydrogen, straight-chain or branched C
1-6
-alkyl, halogeno-C
1-6
-alkyl, hydroxy-C
1-6
-alkyl, C
1-4
-alkanoyloxyalkyl, C
1-2
-alkoxyalkyl, amino-C
1-6
-alkyl, C
1-6
-alkylamino-C
1-6
-alkyl, C
1-6
-dialkylamino-C
1-6
-alkyl, C
1-6
-trialkylammonium-C
1-6
-alkyl halide, nitro-C
1-4
-alkyl, cyano-C
1-4
-alkyl, C
1-4
-alkoxycarbonyl-C
1-4
-alkyl, carbamoyl-C
1-4
-alkyl, carboxyl-C
1-4
-alkyl, C
2-6
-alkenyl, C
2-6
-alkinyl, C
3-6
-cycloalkyl, C
3-6
-cycloalkyl-C
1-2
-alkyl, aryl, aryl-C
1-2
-alkyl, heteroaryl, heteroaryl-C
1-2
-alkyl, formyl, C
1-4
-alkoxydicarbonyl, or for a radical from the group consisting of G
1
, G
2
, G
3
and G
4
in which
R
6
represents hydrogen, straight-chain or branched C
1-6
-alkyl, C
3-6
-cycloalkyl, aryl-C
1-2
-alkyl, heteroaryl-C
1-2
-alkyl, which are optionally substituted,
R
6
and R
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
7
and R
8
independently of one another represent hydrogen, straight-chain or branched C
1-6
-alkyl, halogeno-C
1-6
-alkyl, hydroxy-C
1-6
-alkyl, C
1-4
-alkanoyloxy-C
1-6
-alkyl, C
1-2
-alkoxy-C
1-6
-alkyl, mercapto-C
1-6
-alkyl, C
1-2
-alkylthio-C
1-6
-alkyl, C
1-2
alkylsulfinyl-C
1-6
-alkyl, C
1-2
-a

Affiliated with

Also associated with

Rating

4a, 5a, 8a,... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 4a, 5a, 8a,..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 4a, 5a, 8a,... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2474419