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Claims for Patent: 4,636,499

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Claims for Patent: 4,636,499

Title: Sulphenamides
Abstract:Novel compounds of the formula IIIa ##STR1## wherein R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a are the same or different and are hydrogen, an alkyl, alkoxy optionally completely or predominantly substituted by fluorine or chlorine, halogen, --CN, --CF.sub.3, --NO.sub.2, --COR, --COOR, aryl, aryloxy or arylalkoxy group, or adjacent groups R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a together with the adjacent carbon atoms in the benzimidazole ring form a 5-, 6- or 7-membered monocyclic ring or a 9-, 10- or 11-membered bicyclic ring, which rings may be saturated or unsaturated and may contain 0-3 heteroatoms selected from N and O and which rings may be optionally substituted with 1-4 substitutents selected from alkyl groups with 1-3 carbon atoms, halogen perferably F or Cl, alkylene radicals containing 4-5 carbon atoms giving spiro compounds, or two or four of these substituents together form one or two oxy groups ##STR2## whereby if R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a together with the adjacent carbon atoms in the benzimidazole ring form two rings they may be condensed with each other, R.sup.5a is hydrogen or an alkyl group, R.sup.6a is hydrogen or an alkyl group or R.sup.5a and R.sup.6a are joined together to form an alkylene chain, R.sup.7a is hydrogen, an alkyl, alkoxy, alkenyloxy, or alkynyloxy group, R.sup.8a is hydrogen or an alkyl group, or R.sup.6a and R.sup.7a, or R.sup.7a and R.sup.8a together with the adjacent carbon atoms in the pyridinium ring form a ring wherein the part constituted by R.sup.6a and R.sup.7a or R.sup.7a and R.sup.8a, is --CH.dbd.CH--CH.dbd.CH--, --O--(CH.sub.2).sub.p --, --CH.sub.2 (CH.sub.2).sub.p --, --O--CH.dbd.CH--, --NH--CH.dbd.CH--, ##STR3## or --S--(CH.sub.2).sub.p --, wherein p is 2, 3 or 4 and the O, S and N atoms always are attached to position 3 in the compound IIIa, R is an alkyl, cycloalkyl, aryl or arylalkyl group, and X.sup.- is a pharmaceutically acceptable anion, process for preparation thereof, pharmaceutical compositions containing such compounds and their use in medicine.
Inventor(s): Brandstrom; Arne E. (Gothenburg, SE), Lindberg; Per L. (Askim, SE), Wallmark; Bjorn (Molnlycke, SE)
Assignee: Aktiebolaget Hassle (Molndal, SE)
Application Number:06/739,425
Patent Claims: 1. A compound of the formula IIIa ##STR18## wherein R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a are the same or different and are hydrogen, and alkyl, alkoxy, optionally completely or predominantly substituted by fluorine or chlorine, halogen, CN, --CF.sub.3, --NO.sub.2, --COR, or --COOR an aryl group having up to 10 carbon atoms, an aryloxy group having up to 10 carbon atoms, or arylalkoxy group having up to 10 carbon atoms in the aryl group and 1 to 5 carbon atoms in the alkloxy group, or adjacent groups R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a together with the adjacent carbon atoms in the benzimidazole ring form a 5-, 6- or 7-membered monocyclic ring or a 9-, 10- or 11-membered bicyclic ring, which rings may be saturated or unsaturated and may contain 0-3 heteroatoms selected from N and O and which rings may be optionally substituted with 1-4 substituents selected from alkyl groups with 1-3 carbon atoms, halogen alkylene radicals containing 4-5 carbon atoms giving spiro compounds, or two or four of these substituents together form one or two oxy groups ##STR19## whereby if R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a together with the adjacent carbon atoms in the benzimidazole ring form two rings they may be condensed with each other,

R.sup.5a is hydrogen or an alkyl group,

R.sup.6a is hydrogen or an alkyl group or R.sup.5a and R.sup.6a are joined together to form an alkylene chain,

R.sup.7a is hydrogen, alkyl, alkoxy, alkenyloxy, or an alkynyloxy group,

R.sup.8a is hydrogen or an alkyl group, or R.sup.6a and R.sup.7a, or R.sup.7a and R.sup.8a together with the adjacent carbon atoms in the pyridinium ring form a ring wherein the part constituted by R.sup.6a and R.sup.7a or R.sup.7a and R.sup.8a is --CH.dbd.CH--CH.dbd.CH--, --O--(CH.sub.2).sub.p --, --CH.sub.2 (CH.sub.2).sub.p --O--CH.dbd.CH--, ##STR20## --N--CH.dbd.CH--, or --S--(CH.sub.2).sub.p --, wherein p is 2, 3 or 4 and the O, S and N atoms always are attached to position 3 and compound 3a in the compound IIIa,

R is an alkyl group, a cycloalkyl group, an aryl group having up to ten carbon atoms or an arylalkyl group having up to ten carbon atoms in the aryl group and one to seven carbon atoms in the alkyl group, and

X.sup.- is a pharmaceutically acceptable anion.

2. A compound according to claim 1, wherein the pharmaceutically acceptable anion is Cl.sup.-, Br.sup.-, I.sup.-, BF.sub.4.sup.-, PF.sub.6.sup.- or AuCl.sub.4.sup.-.

3. A compound according to claim 1 wherein R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a are the same or different and are each hydrogen, a lower alkyl group having 1-7 carbon atoms, a lower alkoxy group having 1-7 carbon atoms, chloro, bromo, fluoro or iodo, an aryl group having up to 10 carbon atoms, an aryloxy group having up to 10 carbon atoms, an aralkoxy group having up to 10 carbon atoms in the aryl group and 1-5 carbon atoms in the alkoxy group, --COR and/or --COOR, wherein R is a lower alkyl group having 1-7 carbon atoms, a cycloalkyl having 3-10 carbon atoms, an aryl having preferably up to 10 carbon atoms or an arylalkyl group having up to 10 carbon atoms in the aryl group and 1-7 carbon atoms in the alkyl group, R.sup.5a is hydrogen or a lower alkyl group having 1-7 carbon atoms, R.sup.6a is hydrogen or a lower alkyl group having 1-7 carbon atoms or R.sup.5a and R.sup.6a are joined together to form an alkenylene chain having 3 carbon atoms, R.sup.7a is hydrogen, a lower alkyl group having 1-7 carbon atoms, an alkoxy group having 1-7 carbon atoms, an alkenyloxy or an alkynyloxy group each having 2-5 carbon atoms and R.sup.8a is hydrogen or a lower alkyl group having 1-7 carbon atoms.

4. A compound according to claim 1 wherein each of R.sup.1a, R.sup.4a, R.sup.5a and R.sup.8a is hydrogen, each of R.sup.2a and R.sup.3a is methyl, R.sup.7a is methoxy, R.sup.6a is hydrogen or methyl and X.sup.- is BF.sub.4.sup.-.

5. A compound according to claim 1 wherein each of R.sup.1a, R.sup.3a, R.sup.4a and R.sup.5a is hydrogen, each of R.sup.6a and R.sup.8a is methyl, R.sup.7a is methoxy, R.sup.2a is hydrogen or methoxy and X.sup.- is PF.sub.6.sup.- or AuCl.sub.4.sup.-.

6. The isomeric mixture of 2,4-dimethyl-3,9-dimethoxy-5H-pyrido-[1',2':4,5][1,2,4]-thiadiazino[2,3-a] benzimidazol-13-ium tetrafluoroborate and 2,4-dimethyl-3,10-dimethoxy-5H-pyrido[1',2':4,5][1,2,4]-thiadiazino[2,3-a] benzimidazol-13-ium tetrafluoroborate.

7. A compound according to claim 1 wherein adjacent groups R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a together with the adjacent carbon atoms in the benzimidazole ring form a 5-, 6- or 7-membered monocyclic ring or a 9-, 10 or 11-membered bicyclic ring, which rings may be saturated or unsaturated and may contain 0-3 heteroatoms selected from N and O, and which rings may be optionally substituted with 1-4 substituents selected from F or Cl, whereby if R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a together with the adjacent carbon atoms in the benzimidazole ring form two rings they may be condensed with each other.

8. A compound according to one of the claim 1-6 wherein compound III(a) is in solid form.

9. A process for the preparation of a compounded formula IIIa ##STR21## wherein R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a are the same or different and are hydrogen, an alkyl, alkoxy optionally completely or predominantly substituted by fluorine or chlorine, halogen, --CN, --CF.sub.3, --NO.sub.2, --COR, or --COOR, an aryl group having up to ten carbon atoms, an arylkoxy group having up to ten carbons, an arylolkoxy group having up to ten carbon atoms in the aryl group and one to five carbon atoms in the arlkoxy group, or adjacent groups R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a together with the adjacent carbon atoms in the benzimidazole ring form a 5-, 6- or 7-membered monocyclic ring or a 9-, 10 or 11-membered bicyclic ring, which rings may be saturated or unsaturated and may contain 0-3 heteroatoms selected from N and O, and which rings may be optionally substituted with 1-4 substituents selected from alkyl groups with 1-3 carbon atoms, halogen, alkylene radicals containing 4-5 carbon atoms giving spiro compounds, or two or four of these substituents together form one or two oxy groups ##STR22## whereby if R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a together with the adjacent carbon atoms in the benzimidazole ring form two rings they may be condensed with each other,

R.sup.5a is hydrogen or an alkyl group,

R.sup.6a is hydrogen or an alkyl group, or R.sup.5a and R.sup.6a are joined together to form an alkylene chain,

R.sup.7a is hydrogen, an alkyl, alkoxy, alkenyloxy or alkynyloxy group,

R.sup.8a is hydrogen or an alkyl group, or R.sup.6a, R.sup.7a, or R.sup.7a and R.sup.8a together with the adjacent carbon atoms in the pyridinium ring form a ring wherein the part constituted by R.sup.6a and R.sup.7a or R.sup.7a and R.sup.8a is --CH.dbd.CH--CH.dbd.CH--, --O--(CH.sub.2).sub.p, --CH.sub.2 (CH.sub.2).sub.p --, --O--CH.dbd.CH--, ##STR23## --N--CH.dbd.CH--, or --S--(CH.sub.2).sub.p --, wherein p is 2, 3 or 4 and the O, S and N atoms always are attached to position 3 in the compound IIIa,

R is an alkyl group, cycloalkyl group, an aryl group having up to 10 carbon atoms, or an arylalkyl group having up to 10 carbon atoms in the aryl group and 1-7 carbon atoms in the alkyl group, and

X.sup.- is a pharmaceutically acceptable anion characterized by reacting a compound of the general formula Ia ##STR24## under transformation conditions with an acid catalyst to form the salt of a compound of the formula IIIa, and

thereafter isolating a compound of the formula IIIa or salt thereof.

10. A process according to claim 9 wherein the reaction is catalyzed by HPF.sub.6, HBF.sub.4 or HAuCl.sub.4.

11. A process according to claim 9 wherein adjacent groups R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a together with the adjacent carbon atoms in the benzimidazole ring form a 5-, 6-, or a 7-membered monocyclic ring or a 9-, 10- and 11-membered bicyclic ring, which rings may be saturated or unsaturated and may contain 0-3 heteroatoms selected from N and O, and which rings are substituted with 1-4 substituents selected from F or Cl, whereby if R.sup.1a, R.sup.2a, R.sup.3a and R.sup.4a together with the adjacent carbon atoms in the benzimidazole ring form two rings they may be condensed with each other.

12. A pharmaceutical preparation for the treatment of inflammatory diseases of the gastrointestinal tract comprising a compound according to claim 1 and the pharmaceutically acceptable carrier therefor, the concentration of said compound in said pharmaceutical composition being sufficient that the preparation is therapeutically effective to treat inflammatory diseases of the gastrointestinal tract in man or animal when administered thereto in an effective dosage form.

13. A pharmaceutical preparation for the treatment of inflammatory diseases of the gastrointestinal tract comprising a compound according to claim 1 and the pharmaceutically acceptable carrier therefor, the concentration of said compound in said pharmaceutical composition being therapeutically effective to inhibit gastric acid secretion when administered to a man or animal in a effective dosage form.

14. A pharmaceutical preparation for the treatment of inflammatory diseases of the gastrointestinal tract comprising a compound according to claim 1 and the pharmaceutically acceptable carrier therefor, the concentration of said compound in said pharmaceutical composition being sufficient that when said composition is administered to a man or animal in an effective dosage form it will impart a cytoprotective effect to the gastrointestinal tract.

15. A method for treating inflammatory diseases of the gastrointestinal tract comprising administering to a man or animal suffering therefrom a compound according to claim 1 in an amount therapeutically effective to treat said inflammatory disease.

16. A method for treating inflammatory diseases of the gastrointestinal tract in man or animal comprising administering to a man or animal suffering therefrom a compound according to claim 1 in an amount effective to suppress gastric acid secretion in said man or animal.

17. A method for treating inflammatory diseases of the qastrointestinal tract in a man or animal comprising administering to such man or animal suffering therefrom a compound according to claim 1 in an amount effective to impart a cytoprotective effect to the man or animal thereby treated.

18. A method according to one of claims 15, 16 or 17 wherein said compound is formulated with a pharmaceutically acceptable carrier before administration.
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