Octacyclodepsipeptides having an endoparasiticidal action

Details Octacyclodepsipeptides having an endoparasiticidal action Octacyclodepsipeptides having an endoparasiticidal action

1994-05-19

2002-10-22

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

06468966

ABSTRACT:

The present invention relates to new octacyclodepsipeptides and to a plurality of processes for their preparation and 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
and R
12
represent the same or different radicals selected from the group of C
2-9
-alkyl, C
1-8
-haloqenoalkyl, C
3-6
-cycloalkyl, aralkyl or aryl,
R
3
to R
10
represent the same or different radicals selected from the group of hydrogen, C
1-5
-alkyl which may optionally be substituted by hydroxyl, alkoxy, carboxyl, carboxamide, imidazolyl, indolyl, guanidino, thio- or thioalkyl, and represent aryl, alkylaryl or heteroarylmethyl which are optionally substituted by halogen, hydroxyl, alkyl, alkoxy, nitro or a —NR
13
R
14
group in which R
13
or R
14
independently from each other represent hydrogen or alkyl or together with the adjoining nitrogen atom form a 5, 6 or 7-membered ring which is optionally interrupted by O, S or N and which is optionally substituted by C
1-4
-alkyl,
R
2
and R
11
represent the same of different radicals selected from the group of C
1-4
-alkyl,
2. Process for the preparation of the compounds of the formula (I)
in which
R
1
and R
12
represent the same or different radicals from the group of C
2-9
-alkyl, C
1-8
-halogenoalkyl, C
3-6
-cycloalkyl, aralkyl or aryl,
R
3
to R
10
represent the same of different radicals selected from the group of hydrogen, C
1-5
-alkyl which may which may optionally be substituted by hydroxyl, alkoxy, carboxyl, carboxamide, imidazolyl, indolyl, guanidino, thio- or thioalkyl, and represent aryl, alkylaryl or heteroarylmethyl which are optionally substituted by halogen, hydroxyl, alkyl, alkoxy, nitro or a —NR
13
R
14
group in which R
13
or R
14
independently from each other represent hydrogen or alkyl or together with the adjoining nitrogen atom form a 5, 6 or 7-membered ring which is optionally interrupted by O, S or N and which is optionally substituted by C
1-4
-alkyl,
R
2
and R
11
represent the same of different radicals selected from the group of C
1-4
-alkyl,
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
to R
12
have the meaning given above.
4. Process for the preparation of the open-chain octadepsipeptides of the formula (II)
in which
R
1
to R
12
possess the meaning given above,
characterized in that compounds of the formula (III)
in which
A represents benzyl 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
R
1
to R
12
possess the meaning given above.
6. Process for the preparation of the compounds of the formula (III)
in which
A represents benzyl and
R
1
to R
12
possess the meaning given above,
characterized in that compounds of the formula (IV)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
1
to R
12
possess the meaning given above,
are hydrolysed in the presence of a diluent and a protic acid.
7. Compounds of the formula (IV)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
1
to R
12
have the meaning given above.
8. Process for the preparation of the compounds of the formula (IV)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
1
to R
12
have the meaning given above,
characterized in that tetradepsipeptides of the formula (V)
in which
A represents benzyl and
Z represents OH or Cl, and
R
1
, R
2
, R
3
, R
4
, R
5
and R
10
have the meaning given above,
and tetradepsipeptides of the formula (VI)
in which
D represents hydrogen and
B represents tert.-butoxy, and
R
6
, R
7
, R
8
, R
9
, R
11
and R
12
have the meaning given above,
are condensed in the presence of a diluent and a suitable coupling reagent.
9. Tetradepsipeptides of the formula (V)
in which
A represents benzyl and
Z represents OH or Cl, and
R
1
, R
2
, R
3
, R
4
, R
5
and R
10
have the meaning given above.
10. Tetradepsipeptides of the formula (VI)
in which
D represents hydrogen and
B represents tert.-butoxy, and
R
6
, R
7
, R
8
, R
9
, R
11
and R
12
possess the meaning given above,
11. Process for the preparation of the tetradepsipeptides of the formula (V)
in which
A represents benzyl and
Z represents OH or Cl, and
R
1
, R
2
, R
3
, R
4
, R
5
and R
10
have the meaning given above,
characterized in that tetradepsipeptides of th
1
e formula (VII)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
1
, R2, R
3
, R
4
, R
5
and R
10
have the meaning given above,
are hydrolysed in the presence of a diluent and a protic acid.
12. Process for the preparation of the tetradepsipeptides of the formula (VI)
in which
D represents hydrogen and
B represents tert.-butoxy, and
R
6
, R
7
, R
8
, R
9
, R
11
and R
12
have the meaning given above,
characterized in that tetradepsipeptides formula (VII)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
1
, R
2
, R
3
, R
4
, R
5
and R
10
possess the meaning given above,
are subjected in the presence of a diluent and a catalyst to hydrogenolysis.
13. Tetradepsipeptides of the formula (VII)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
1
, R2, R
3
, R
4
, R
5
and R
10
have the meaning given above.
14. Process for the preparation of the tetradepsipeptides of the formula (VII)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
1
, R
2
, R
3
, R
4
, R
5
and R
10
possess the meaning given above,
characterized in that didepsipeptides of the formula (VIII)
in which
A represents benzyl and
Z represents OH or Cl, and
R
1
, R
3
and R
10
possess the meaning given above and didepsipeptides of the formula (IX)
in which
D represents hydrogen and
B represents tert.-butoxy, and
R
2
, R
4
and R
5
possess the meaning given above,
are condensed in a diluent in the presence of a suitable coupling reagent.
15. Didepsipeptides of the formula (VIII)
in which
A represents benzyl and
Z represents OH or Cl, and
R
1
, R
3
and R
10
possess the meaning given above.
16. Didepsipeptides of the formula (IX)
in which
D represents hydrogen and
B represents tert.-butoxy, and
R
2
, R
4
and R
5
possess the meaning given above.
17. Process for the preparation of didepsipeptides of the formula (VIII)
in which
Z represents OH or Cl and
A represents benzyl, and
R
1
, R
3
and R
10
possess the meaning given above. The processes are characterized in that a compound of the formula (X)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
1
, R
3
and R
10
possess the meaning given above and a diluent are hydrolysed in the presence of a protic acid.
18. Process for the preparation of didepsipeptides of the formula (IX)
in which
D represents hydrogen and
B represents tert.-butoxy, and
R
2
, R
4
and R
5
possess the meaning given above, characterized in that compounds of the formula (XI)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
2
, R
4
and R
5
possess the meaning given above,
are subjected in the presence of a diluent and a catalyst to hydrogenolysis.
19. Didepsipeptides of the formula (X)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
1
, R
3
and R
10
possess the meaning given above.
20. Didepsipeptides of the formula (XI)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
2
, R
4
and R
5
possess the meaning given above.
21. Process for the preparation of didepsipeptides of the formula (X)
in which
A represents benzyl and
B represents tert.-butoxy, and
R
1
, R
3
and R
10
possess the meaning given above,
characterized in that an aminocarboxylic acid of the formula (XII

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