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Claims for Patent: 5,510,353

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Claims for Patent: 5,510,353

Title: Certain aminoguanidine compounds, pharmaceutical compositions containing them and their use in treating gastrointestinal motility disorders and disorders associated with cephalic pain
Abstract:Compounds of formula wherein A is derived from optionally substituted benzothiophene, indole, 4-aza-and 7-aza-benzothiophene or-indole, A bearing in position 5 hydrogen, halogen, optionally substituted alkyl, hydroxy, nitro, amino, alkylamino, acylamino, alkoxycarbonyl, sulfamoyl, cyano, trimethylsilyl, carboxy, carbamoyl, phosphate, oxycarbamoyl, heterocyclic radical or ether or ester group, X-Y is --CR.sub.8 .dbd.N-- or CH(R.sub.8)--NH-- wherein R.sub.8 is -H or alkyl and attached at position 3 of A, and B is a heterocyclic radical or a residue ##STR1## wherein R.sub.10 is H, optionally substituted alkyl, cycloalkyl, aryl, adamantyl, acyl or carbamoyl and X.sub.2 is alkylthio or NR.sub.3 R.sub.10 wherein R.sub.3 is H or alkyl or R.sub.3 and R.sub.10 together with the nitrogen atom to which they are attached form a heterocyclic radical, in free form or in salt form, have pharmacological activity, e.g. for treating gastrointestinal disorders.
Inventor(s): Giger; Rudolf K. A. (Muttenz, CH), Mattes; Henri (Brunstadt, FR)
Assignee: Sandoz Ltd. (Basel, CH)
Application Number:08/370,038
Patent Claims: 1. A compound of the formula ##STR27## wherein R.sub.1 hydrogen; C.sub.1-6 alkyl; (C.sub.1-6 alkyl)carbonyl; or benzoyl;

R.sub.5 is hydrogen; halo; C.sub.1-6 alkyl; hydroxy; nitro; amino; C.sub.1-4 alkylamino; C.sub.1-10 alkylcarbonylamino; C.sub.2-6 alkoxy-carbonyl; SO.sub.2 NR.sub.a R.sub.b ; cyano; trimethylsilyl; C.sub.1-6 alkyl monosubstituted by --SO.sub.2 -(C.sub.1-6 alkyl), --SO.sub.2 NR.sub.a R.sub.b, --CONR.sub.a R.sub.b, --NH--SO.sub.2 --(C.sub.1-6 alkyl), --N (C.sub.1-6 alkyl)--SO.sub.2 --(C.sub.1-6 alkyl), --NR.sub.a R.sub.b, C.sub.2-6 alkoxycarbonyl or --PO(C.sub.1-4 alkyl).sub.2 ; carboxy; CONR.sub.a R.sub.b ; --PO(C.sub.1-4 alkyl).sub.2 ;

--OCONR.sub.c R.sub.d ; C.sub.1-6 alkoxy; C.sub.1-6 alkoxy monosubstituted

by hydroxy, C.sub.1-4 alkoxy, NR.sub.a R'.sub.b, CONR.sub.a R.sub.b, CSNR.sub.a R.sub.b,

(C.sub.1-6 alkyl)carbonyloxy or benzoyloxy;

C.sub.2-6 alkenyloxy; pyridyl-carbonyloxy;

(C.sub.1-6 alkyl)carbonyloxy; or benzoyloxy;

and wherever they appear in the above definition of

R.sub.5, each of R.sub.a and R.sub.b, independently, is hydrogen or C.sub.1-6 alkyl; R'.sub.b is hydrogen or C.sub.1-6 alkyl; and each of R.sub.c and R.sub.d, independently, is C.sub.1-6 alkyl;

R.sub.7 is hydrogen, halo, C.sub.1-6 alkyl or C.sub.1-6 alkoxy;

X--Y is --CR.sub.8 .dbd.N-- or---H(R.sub.8)--NH-- where R.sub.8 is hydrogen or C.sub.1-6 alkyl; and

B is a radical of formula (a) or (b), ##STR28## where n is 1 or 2;

A.sub.1 is C.dbd.O or CH.sub.2 ;

X.sub.1 is S; NR.sub.11 where R.sub.11 is hydrogen; or CR.sub.12 R.sub.13 where each of R.sub.12 and R.sub.13, independently, is hydrogen or C.sub.1-4 alkyl;

R.sub.10 is hydrogen; C.sub.1-12 alkyl; C.sub.1-6 alkyl monosubstituted by hydroxy, aryl, aryloxy, adamantyl, a heterocyclic radical, --NH--SO.sub.2 -aryl or --NR.sub.15 --COR.sub.16 where R.sub.15 is hydrogen or C.sub.1-4 alkyl and R.sub.16 is C.sub.1-6 alkyl, C.sub.5-7 cycloalkyl, C.sub.5-7 cycloalkyl-C.sub.1-4 alkyl, aryl or aryl(C.sub.1-4 alkyl); C.sub.5-7 cycloalkyl; adamantyl; (C.sub.1-10 alkyl)-carbonyl; benzoyl; phenyl(C.sub.1-4 alkyl)carbonyl; or --CONHR.sub.14 where R.sub.14 is C.sub.1-10 alkyl or C.sub.5-7 cycloalkyl;

and wherever "aryl" appears as is or in the significances "aryloxy", "--NH--SO.sub.2 -aryl" or "aryl(C.sub.1-4 alkyl)" in the above definition, it is phenyl or phenyl mono- or disubstituted by fluoro, chloro, methyl or methoxy; and wherever the term "a heterocyclic radical" appears in the above definition, it is pyridyl, imidazolyl, benzimidazolyl, pyrrolidinyl, piperidino, pyrazinyl, perhydroindolyl or a radical of formula (d) ##STR29## where E is --CH.sub.2 CH.sub.2 --,--CH.sub.2 N(R.sub.17)-- where R.sub.17 is hydrogen or C.sub.1-4 alkyl; or --(CH.sub.2).sub.3 --where one or two hydrogens therein can be replaced by C.sub.1-6 alkyl; and E.sub.1 is --CO--or --CH.sub.2 --;

and

X.sub.2 is --SR.sub.20 where R.sub.20 is C.sub.1-6 alkyl; or --NR.sub.3 R'.sub.10 where either R.sub.3 is hydrogen or C.sub.1-6 alkyl and R'.sub.10 has one of the significances indicated above for R.sub.10 ; or R.sub.3 and

R'.sub.10 together with the nitrogen atom to which they are attached form a heterocyclic radical as defined above;

with the proviso that where B is a radical of formula (b), only one of R.sub.10 and R'.sub.10 can be other than hydrogen and X.sub.2 can be --SR.sub.20 only when R.sub.10 is hydrogen; which compound is in free base or pharmaceutically acceptable salt form.

2. A compound of claim 1 wherein each of R.sub.1 and R.sub.7 is hydrogen.

3. A compound of claim 1 wherein each of R.sub.1 and R.sub.7 is hydrogen and R.sub.5 is hydroxy or C.sub.1-6 alkoxy.

4. A compound of claim 1 wherein at least one of R.sub.1 and R.sub.7 is other than hydrogen.

5. A compound of claim 1 wherein each of R.sub.1 and R.sub.7 is hydrogen and R.sub.5 is hydrogen, hydroxy, C.sub.1-6 alkoxy, carboxy, C.sub.2-6 alkoxycarbonyl, CONR.sub.a R.sub.b where R.sub.a and R.sub.b are as defined in claim 14, SO.sub.2 NH(C.sub.1-6 alkyl) or C.sub.1-6 alkyl monosubstituted by --SO.sub.2 --(C.sub.1-6 alkyl) or --PO(C.sub.1-4 alkyl).sub.2.

6. A compound according to claim 1 which is 5-methoxy-indole-3-carboxaldehyde amino-(pentyl-amino)methylenehydrazone, in free base form or in pharmaceutically acceptable salt form.

7. A compound according to claim 1 which is [5-hydroxy-indole-3-carboxaldehydeamino(N-cyclo-hexylureido)methylenehydra zone, 5hydroxy-indole-3-carboxaldehyde amino (3-benzimidazol-2-yl-propylamino)methylenehydrazone] 5-carbamoyl-indole-3-carboxaldehydeamino(pentyl-amino)methylenehydrazone, 5-hydroxy-7-methyl-indole-3-carboxaldehyde amino(pentyl-amino)methylene-hydrazone, 1-ethyl-5-hydroxy-indole-3-carboxaldehyde amino (pentyl-amino)methylenehydrazone and 5-hydroxy-7-methyl-indole-3-carboxaldehyde amino (N-methyl-N-pentyl-amino)-methylenehydrazone, all of which are in free base form or in pharmaceutically acceptable salt form.

8. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and a therapeutically effective amount of a compound of claim 1, which compound is in free base or pharmaceutically acceptable salt form.

9. A method of treating a gastrointestinal motility disorder comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound of claim 1, which compound is in free base or pharmaceutically acceptable salt form.

10. A method according to claim 9 wherein the disorder is irritable bowel syndrome, gastroesophageal reflux disease or constipation.

11. A method of treating a disorder associated with cephalic pain comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound of claim 1, which compound is in free base or pharmaceutically acceptable salt form.

12. A method according to claim 11 wherein the disorder is migraine headaches.

13. A compound of claim 1 wherein B is a radical ##STR30## or a radical of formula (b) where R.sub.10 and X.sub.2 are as defined in claim 1.

14. The compound of claim 6 which is in pharmaceutically acceptable acid addition salt form.

15. The compound of claim 6 which is in hydrogen maleate form.

16. A compound according to claim 1 where X--Y is --CR.sub.8 .dbd.N--.

17. A compound according to claim 1 where B is a radical of formula (b) where R.sub.10 is hydrogen and X.sub.2 is --NR.sub.3 R'.sub.10 where R.sub.3 is hydrogen or C.sub.1-4 alkyl and R'.sub.10 is C.sub.1-12 alkyl.
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