Thiazoline acid derivatives
View Patent ↗Phenyl- and pyridyl-substituted thiazoline acid derivatives useful in diagnosing and treating pathological conditions associated with an excess of trivalent metals in humans and animals.
1. A compound of the formula:
wherein:
Z is CH or N;
R is HI or acyl;
R 1 , R 2 , R 3 and R 5 may be the same or different and represent H, alkyl or hydrocarbyl arylalkyl having up to 14 carbon atoms;
R 4 is H or alkyl having 1-4 carbon atoms with the proviso that:
R 4 is alkyl having 1-4 carbon atoms when
Z is CH, R 5 is H and R 4 O is attached to the carbon atom labelled 4; and
that R 5 is H, when Z is CH, R, R 1 , R 2 , R 3 and R 4 are each H and R 4 O is attached to the carbon atom labeled 3 ; a salt thereof with a pharmaceutically acceptable acid or a pharmaceutically acceptable complex thereof.
2. A compound of claim 1 wherein Z is N and R=R 1 =R 2 =R 3 =R 4 =R 5 =H.
3. A compound of claim 1 wherein Z is CH, R=R 1 =R 2 =R 3 =R 5 =H, and R 4 is alkyl having 1-4 carbon atoms.
4. A compound of claim 3 wherein R 4 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or t-butyl .
5. A compound of claim 1 wherein Z is N, R=R 1 =R 2 =R 3 =R 5 =H, and R 4 is alkyl having 1-4 carbon atoms.
6. A compound of claim 5 wherein R 4 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or t-butyl .
7. A compound of claim 1 having the formula:
wherein:
Z, R, R 1 , R 2 , R 3 , R 4 and R 5 have the meanings ascribed thereto in claim 1 ;
a salt thereof with a pharmaceutically acceptable acid or a pharmaceutically acceptable complex thereof.
8. A compound of claim 7 wherein Z is N and R=R 1 =R 2 =R 3 =R 4 =R 5 =H.
9. A compound of claim 7 wherein Z is CH, R=R 1 =R 2 =R 3 =R 5 =H, and R 4 is alkyl having 1-4 carbon atoms.
10. A compound of claim 9 wherein R 4 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or t-butyl .
11. A compound of claim 7 wherein Z is N, R=R 1 =R 2 =R 3 =R 5 =H, and R 4 is alkyl having 1-4 carbon atoms.
12. A compound of claim 11 wherein R 4 is methyl, ethyl, n-propyl, isopropyl, or t-butyl .
13. A compound of claim 7 1 wherein Z is CH, R=R 4 =R 1 =R 2 =R 5 =H, and R 3 is alkyl having 1-4 carbon atoms.
14. A compound of claim 7 1 wherein Z is CH, R=R 4 =R 1 =R 2 =R 5 =H, and R 3 is alkyl having 1-4 carbon atoms.
15. A compound of claim 7 1 wherein Z is CH, R 4 =R 3 =R 2 =R 5 =H, and R 1 is alkyl having 1-4 carbon atoms.
16. A compound of claim 7 wherein Z is N, R=R 4 =R 1 =R 2 =R 5 =H, and R 3 is alkyl having 1-4 carbon atoms.
17. A compound of claim 7 wherein Z is N, R=R 4 =R 1 =R 3 =R 5 =H, and R 2 is alkyl having 1-4 carbon atoms.
18. A compound of claim 7 wherein Z is N, R=R 4 =R 3 =R 2 =R 5 =H, and R 1 is alkyl having 1-4 carbon atoms.
19. An optically pure compound of claim 1 or 7 .
20. An (S)-enantiomer compound of claim 7 having the formula:
a salt thereof with a pharmaceutically acceptable acid or a pharmaceutically acceptable complex thereof.
21. An (S)-enantiomer compound of claim 7 having the formula:
a salt thereof with a pharmaceutically acceptable acid or a pharmaceutically acceptable complex thereof.
22. An (S)-enantiomer compound of claim 7 having the formula:
a salt thereof with a pharmaceutically acceptable acid or a pharmaceutically acceptable complex thereof.
23. An (R)-enantiomer compound of claim 7 having the formula:
24. An (R)-enantiomer compound of claim 7 having the formula:
a salt thereof with a pharmaceutically acceptable acid or a pharmaceutically acceptable complex thereof.
25. An (R)-enantiomer compound of claim 7 having the formula:
a salt thereof with a pharmaceutically acceptable acid or a pharmaceutically acceptable complex thereof.
26. A pharmaceutical composition in unit dosage form for treating a pathological condition in a human or non-human animal that is associated with an excess of a trivalent metal, ion or compound thereof comprising a therapeutically effective amount of a compound according to claim 1 or 7 and a pharmaceutically acceptable carrier therefor.
27. A method of preventing or treating a pathological condition in a human or non-human animal that is associated with an excess of a trivalent metal, ion or compound thereof comprising administering to said animal a therapeutically effective amount of a compound according to claim 1 or 7 .