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Claims for Patent: 4,760,075

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Claims for Patent: 4,760,075

Title: N-thiazolylmethylthioalkyl-N-alkyl-amidines and related compounds
Abstract:N-alkyl-N'-(2-aminomethyl-4-thiazolylmethylthio)alkyl guanidines, thioureas, ethenediamines and related compounds, H.sub.2 -receptor antagonists, useful in inhibiting gastric acid secretion in mammals.
Inventor(s): Pioch; Richard P. (Indianpolis, IN)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Application Number:06/814,274
Patent Claims: 1. A compound of the formula ##STR35## wherein R.sup.1 represents hydrogen, methyl, ethyl, benzyl or benzoyl; R.sup.2 represents methyl or ethyl; or R.sup.1 and R.sup.2 taken together with the nitrogen atom to which they are attached, form a piperidino, pyrrolidino or morpholino radical;

R.sup.3 is hydrogen or methyl;

Z is O, S or CH.sub.2 ;

n is 2 or 3 when Z is O or S and n is 1, 2 or 3 when Z is CH.sub.2 ;

Q is ##STR36## wherein A is N-CN, N-NO.sub.2, CH-NO.sub.2, S, N-SO.sub.2 -aryl, N-SO.sub.2 -methyl or N-CO-NH.sub.2, wherein aryl is phenyl or tolyl; and

B is NHR, wherein R is methyl, ethyl, cyclopropyl or (2-hydroxy)ethyl; or

B is YR.sup.4, wherein Y is oxygen or sulfur and R.sup.4 is (C.sub.1 -C.sub.3 alkyl, -CH.sub.2 -(C.sub.2 -C.sub.4) alkenyl or benzyl; provided that when Q is ##STR37## B is NHR or O--(C.sub.1 -C.sub.2)-alkyl; and acid addition salts thereof.

2. A thiazole derivative as claimed in claim 1 wherein R.sup.1 is hydrogen, methyl, ethyl, benzyl or benzoyl; R.sup.2 is methyl or ethyl; or R.sup.1 and R.sup.2 taken together with the adjacent nitrogen atom represent a piperidino, pyrrolidino or morpholino group; R.sup.3 is hydrogen or methyl; A is N-CN, N--NO.sub.2, CH-NO.sub.2, S, N-SO.sub.2 --aryl, N-SO.sub.2 --methyl or N-CO-NH.sub.2, where aryl is phenyl or tolyl; B is NHR or YR.sub.4 wherein R is methyl, ethyl, cyclopropyl or 2-(hydroxy)ethyl and R.sup.4 is (C.sub.1 -C.sub.3)alkyl; provided that when B is YR.sup.4, Q is C.dbd.A; or a pharmaceutically-acceptable, acid addition salt thereof.

3. A thiazole derivative as claimed in claim 1, wherein Z is sulfur.

4. A thiazole derivative as claimed in claim 1 wherein n is 2.

5. A thiazole derivative as claimed in claim 1, wherein R.sup.3 is hydrogen.

6. A thiazole derivative as claimed in claim 1, wherein R.sup.1 and R.sup.2 are methyl.

7. A thiazole derivative as claimed in claim 1, wherein A is NCN or CHNO.sub.2.

8. A thiazole derivative as claimed in claim 1, wherein B is NHR where R is methyl or ethyl.

9. A thiazole derivative as claimed in claim 8, wherein B is methylamino.

10. A compound according to claim 1 in which R.sup.3 is H, R.sup.1 is H, methyl or ethyl, R.sup.2 is methyl or ehtyl, Z is S, Q is ##STR38## A is N-CN, N-NO.sub.2 or CH-NO.sub.2, B is NHR, and R is methyl or ethyl.

11. A compound according to claim 10, said compund being N-methyl-N'-2-(2-methylaminomethyl-4-thiazolylmethylthio)ethyl 2-nitro-1,1-ethenediamine.

12. A compound according to claim 10, said compound being N-methyl-N'-2-(2-dimethylaminomethyyl-4-thiazoIylmethylthio)ethyl-N"-cyano guanidine.

13. A pharmaceutical formulation in unit dosage form adapted for oral administration to achieve an antisecretory effect, comprising per dosage unit an antisecretorially-effective amount of a compound of claim 1 wherein B is NHR plus one or more pharmaceutical excipients.

14. A pharmaceutical formulation in unit dosage form adapted for oral administration to achieve an antisecretory effect, comprising per dosage unit an antisecretorially-effective amount of a compound of claim 10 plus one or more pharm.aceutical excipients.

15. A pharmaceutical formulation according to claim 13 containing from 50-80 mg. of active drug per dosage unit.

16. A pharmaceutical formulation in unit dosage form adapted for oral administration to achieve an antisecretory effect, comprising per dosage unit an antisecretorially-effective amount of a compound according to claim 2 plus one or more pharmaceutical excipients.

17. A method for inhibiting gastric acid secretion in mammals which comprises administering to a mammal, whose gastric acid secretion is excessive and who is in need of treatment, an antisecretorially effective amount of a compound according to claim 1.

18. A method according to claim 17 in which from 140-350 mg. of drug per day are administered orally to humans.

19. A method according to claim 18 in which the oral daily dose is from 2-5 mg./kg. of mammalian body weight.

20. A method for inhibiting gastric acid secretion in mammals which comprises administering to a mammal, whose gastric acid secretion is excessive and who is in need of treatment, an antisecretorially effective amount of a compound according to claim 2.

21. A method for inhibiting gastric acid secretion in mammals which comprises administering to a mammal, whose gastric acid secretion is excessive and who is in need of treatment, an antisecretorially effective amount of a compound according to claim 10.

22. A method according to claim 17 in which the antisecretory drug is administerd orally.

23. A method according to claim 17 in which the antisecretory drug is administered parenterally.

24. A method of inhibiting H.sub.2 histamine receptors which comprises administering to an animal an amount effective to inhibit said receptors of a compound according to claim 1 wherein B is NHR.
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