Octacyclodepsipeptides having an endoparasiticidal action

Details Octacyclodepsipeptides having an endoparasiticidal action Octacyclodepsipeptides having an endoparasiticidal action

1994-05-19

2002-04-09

Ponnaluri, Padmashri (Department: 1627)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

C514S002600, C514S011400, C530S317000

Reexamination Certificate

active

06369028

ABSTRACT:

The present invention relates to new octacyclodepsipeptides and to a plurality of processes for their preparation, and to their use as endoparasiticides.
European Published Specification 0 382 173 discloses a cyclic depsipeptide with the designation PF 1022. The compound possesses an anthelmintic action. At low application rates, however, the activity in some cases leaves something to be desired.
The present invention relates, then, to:
1. Compounds of the general formula (I)
in which
R
1
, R
2
, R
11
and R
12
represent the same or different radicals selected from the group of C
1-8
-alkyl, C
1-8
-halogenoalkyl, C
3-6
-cycloalkyl, aralkyl or aryl.
R
3
, R
5
, R
7
, R
9
, represent the same or different radicals selected from the group of hydrogen or straight-chain
C
1-5
-alkyl or branched C
4-7
-alkyl which may optionally be substituted by hydroxyl, C
1-4
-alkoxy, carboxyl
 carboxamide,
 imidazolyl, indolyl, guanidino, —SH
or C
1-4
-alkylthio, and furthermore represents aryl, aralkyl or heteroarylmethyl which may be substituted by halogen, hydroxyl, C
1-4
-alkyl, C
1-4
-alkoxy, nitro or a —NR
13
R
14
group in which R
13
and R
14
independently from each other represent hydrogen or alkyl or together with the adjoining nitrogen atom forms a 5, 6 or 7-membered ring which is optionally interrupted by O, S or N and which is optionally C
1-4
-alkyl substituted,
R
4
, R
6
, R
8
, R
10
represent the same or different radicals selected from the group of hydrogen, straight-chain C
1-5
-alkyl and represents isopropyl, sec.-butyl, t-butyl, C
2-6
-alkenyl, C
3-7
-cycloalkyl, which may optionally be substituted by hydroxyl, C
1-4
-alkoxy, carboxyl, carboxamide, imidazolyl, indolyl, guanidino, SH or C
1-4
-alkylthio and represent aryl, aralkyl or heteroarylmethyl which may be substituted by halogen, hydroxyl, C-
1-4
-alkyl, C
1-4
-alkoxy,
and stereoisomers thereof.
2. Process for the preparation of the compounds of the formula (I)
in which
R
1
, R
2
, R
11
and R
12
represent the same or different radicals selected from the group of C
1-8-
alkyl, C
1-8
-halogenoalkyl, C
3-6
-cycloalkyl, aralkyl or aryl.
R
3
represents hydrogen or straight-chain C
1-5
-alkyl which may optionally be substituted by hydroxyl, C
1-4
-alkoxy, carboxyl
 carboxamide,
 imidazolyl, indolyl,
guanidino, —SH or C
1-4
-alkylthio, and represents isopropyl or sec.-butyl and furthermore represents aryl, aralkyl or heteroarylmethyl which may be substituted by halogen, hydroxyl, C
1-4
-alkyl, C
1-4
-alkoxy, nitro or
a —NR
13
R
14
group in which R
13
and R
14
independently from each other represent hydrogen or alkyl or together with the adjoining nitrogen atom forms a 5, 6 or 7-membered ring which is optionally interrupted by O, S or N and which is optionally C
1-4
-alkyl substituted,
R
4
to R
10
represent the same or different radicals selected from the group of hydrogen, straight-chain C
1-5
-alkyl which may optionally be substituted by
hydroxyl, C
1-4
-alkoxy, carboxyl, carboxamide, imidazolyl, indolyl, guanidino, SH or C
1-4
-alkylthio, and represent aryl, aralkyl or heteroarylmethyl which may be substituted
by halogen, hydroxyl, C
1-4
-alkyl, C
1-4
-alkoxy, nitro or a —NR
13
R
14
group in which R
13
and R
14
independently from each other represent hydrogen or alkyl or together with the adjoining nitrogen atom forms a 5, 6 or 7-membered ring which is optionally interrupted by O, S or N and which is optionally C
1-4
-alkyl substituted,
characterized in that
open-chain octadepsipeptides of the formula (II)
in which
R
1
to R
12
have the meaning given above are cyclized
in the presence of a diluent and in the presence of a coupling reagent;
3. Open-chain octadepsipeptides of the formula (II)
in which
R
1
, R
2
, R
11
and R
12
represent the same or different radicals selected from the group of C
1-8
-alkyl, C
1-8
-halogenoalkyl, C
3-6
-cycloalkyl, aralkyl, alkyl,
R
3
, R
5
, R
7
, R
9
represent “the same or different radicals selected from the group of” hydrogen or straight-chain C
1-5
-alkyl or branched C
4-7
-alkyl which may optionally be substituted by hydroxyl, C
1-4
-alkoxy, carboxyl
 carboxamide,
 imidazolyl, indolyl, guanidino, —SH or
C
1-4
-alkylthio and furthermore represents aryl, aralkyl or heteroarylmethyl which may be substituted by halogen, hydroxyl, C
1-4
-alkyl, C
1-4
-alkoxy, nitro or a —NR
13
R
14
group in which R
13
and R
14
independently from each other represent hydrogen or alkyl or together with the adjoining nitrogen atom forms a 5, 6 or 7-membered ring which is optionally interrupted by O, S or N and which is optionally C
1-4
-alkyl substituted,
R
4
, R
6
, R
8
, R
10
represent the same or different radicals selected from the group of hydrogen, straight-chain C
1-5
-alkyl and represents isopropyl, sec.-butyl, t-butyl, C
2-6
-alkenyl, C
3-7
-cycloakyl, which may optionally be substituted by hydroxyl, C
1-4
-alkoxy, carboxyl, carboxamide, imidazolyl, indolyl, guanidino, SH or C
1-4
-alkylthio, and represent aryl, aralkyl or heteroarylmethyl which may be substituted by halogen, hydroxyl C
1-4
-alkyl, C
1-4
-alkoxy,
and stereoisomers thereof.
4. Process for the preparation of the open-chain octadepsipeptides of the formula (II)
in which
R
1
, R
2
, R
11
and R
12
represent the same or different radicals selected from the group of C
1-8
-alkyl, C
1-8
-halogenoalkyl, C
3-6
-cycloalkyl, aralkyl, aryl,
R
3
, R
5
, R
7
, R
9
represent the same or different radicals selected from the group of hydrogen or straight-chain C
1-5
-alkyl or branched C
4-7
-alkyl which may optionally be substituted by hydroxyl, C
1-4
-alkoxy, carboxyl
 carboxamide,
 imidazolyl, indolyl, guanidino, —SH
C
1-4
-alkylthio and furthermore represents aryl, aralkyl or heteroarylmethyl which may be substituted by halogen, hydroxyl, C
1-4
-alkyl, C
1-4
-alkoxy, nitro or a —NR
13
R
14
group in which R
13
and R
14
independently from each other represent hydrogen or alkyl or together with the adjoining nitrogen atom forms a 5, 6 or 7-membered ring which is optionally interrupted by O, S or N and which is optionally C
1-4
-alkyl substituted,
R
4
, R
6
, R
8
, R
10
represent he same or different radicals selected from the group of hydrogen, straight-chain C
1-5
-alkyl and represents isopropyl, sec.-butyl, t-butyl, C
2-6
-alkenyl, C
3-7
-cycloakyl, which may optionally be substituted by hydroxyl, C
1-4
-alkoxy, carboxyl, carboxamide, imidazolyl, indolyl, guanidino, SH or C
1-4
-alkylthio, and represent aryl, aralkyl or heteroarylmethyl which may be substituted by halogen,
hydroxyl, C
1-4
-alkyl, C
1-4
-alkoxy,
characterized in that compounds of the formula (III)
in which
A represents benzyl and
B represents OH and
R
1
to R
12
possess the meaning given above
are subjected in the presence of a diluent and a catalyst to hydrogenolysis.
5. Compounds of the formula (III)
in which
A represents benzyl and
B represents OH and
R
1
, R
2
, R
11
and R
12
represent the same or different radicals selected from the group of C
1-8
-alkyl, C
1-8
-halogenoalkyl, C
3-6
-cycloalkyl, aralkyl, aryl,
R
3
, R
5
, R
7
, R
9
represent the same or different radicals selected from the group of hydrogen or straight-chain C
1-5
-alkyl or branched C
4-7
-alkyl which may optionally be substituted by hydroxyl, C
1-4
-alkoxy, carboxyl
 carboxamide,
 imidazolyl, indolyl, guanidino, —SH
C
1-4
-alkylthio and furthermore represents aryl, aralkyl or heteroarylmethyl which may be substituted by halogen, hydroxyl, C
1-4
-alkyl, C
1-4
-alkoxy, nitro or a —NR
13
R
14
group in which R
13
and R
14
independently from each other represent hydrogen or alkyl or together with the adjoining nitrogen atom forms a 5, 6 or 7-membered ring which is optionally interrupted by O, S or N and which is optionally C
1-4
-alkyl substituted,
R
4
, R
6
, R
8
, R
10
represent the same or different radicals selected from the group of hydrogen, straight-chain C
1-5
-alkyl and represents isopropyl, sec.-butyl, t-butyl, C
2-6
-alkenyl, C
3-7
-cycloakyl, which may optionally be substituted by hydroxyl, C
1-4
-alkoxy,

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