Claims
- 1. A (fused)benz(thio)amide of the general formula: ##STR401## wherein A represents a single bond or a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a vinylene group, a propenylene group, a butenylene group, a butadienylene group or an ethylene group optionally substituted by one, two or three of straight or branched alkyl group(s) of from 1 to 10 carbon atom(s) and/or phenyl group(s);
- B represents a roup of general formula: ##STR402## T represents an oxygen atom or a sulphur atom; R.sup.1 represents a group of general formula: ##STR403## (iv) a straight or branched alkyl, alkenyl or alkynyl group of from 1 to 20 carbon atoms,
- wherein R.sup.5 and R.sup.6 independently represent a hydrogen atom or a halogen atom or a straight or branched alkyl, alkenyl or alkynyl group of up to 20 carbon atoms, one, two, three, four or five of the optional carbon atom(s) being unreplaced or replaced by one or more oxygen atom(s), sulphur atom(s), halogen atom(s), nitrogen atom(s), benzene ring(s), thiophene ring(s), naphthalene ring(s), carbocyclic ring(s), thiophene ring(s), naphthalene ring(s), carbocyclic (ring(s) of from 4 to 7 carbon atom(s), carbonyl group(s), carbonyloxy group(s), hydroxy group(s), carboxy group(s), azido group(s) and/or nitro group(s);
- R.sup.2 represents a hydrogen atom or a straight or branched alkyl group of from 1 to 6 carbon atom(s);
- R.sup.3 represents a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a group of general formula: --COOR.sup.7, wherein R.sup.7 represents a hydrogen atom or a straight or branched alkyl group of from 1 to 6 carbon atom(s), or a straight or branched alkyl, alkenyl or alkynyl group of from 1 to 6 carbon atom(s);
- R.sup.4 represents a group of general formula: ##STR404## wherein U represents an oxygen atom or a sulphur atom, R.sup.8 represents a hydrogen atom or a straight or branched alkyl group of from 1 to 6 carbon atoms(s), n and m represent an integer of from 1 to 10, respectively, and p and q represent zero or an integer of from 1 to 10, respectively
- or non-toxic salts thereof.
- 2. A compound according to claim 1, wherein B is 2,3,5,6-tetrahydro-1,4-dioxane ring (i.e. the formula: ##STR405##
- 3. A compound according to claim 2, wherein A is a single bond, and the T is an oxygen atom.
- 4. A compound according to claim 3, wherein R.sup.1 is a group of the general formula: ##STR406## wherein R.sup.5 and R.sup.6 have the same meaning as in claim 1.
- 5. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a hydrogen atom or a straight or branched alkyl group of from 1 to 20 carbon atom(s).
- 6. A compound according to claim 5, wherein the compound is selected from the group consisting of
- 8-(p-pentylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-pentylbenzoyl)amino-2-(5-tetrazolyl)-6-chloro-1,4-benzodioxane,
- 8-(m-octylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(o-pentylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-butylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-hexylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-heptylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-octylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-nonylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-decylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-undecylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-(p-dodecylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 7. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a straight or branched alkoxy group of from 1 to 19 carbon atom(s).
- 8. A compound according to claim 7, wherein the compound is selected from the group consisting of
- 8-(p-pentyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(m-pentyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(o-pentyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-butyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-nonyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-propoxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-hexyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-heptyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-octyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-decyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-isopentyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-isohexyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(1-methylbutoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[N-methyl-N-(p-octynyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- 8-(p-octyloxybenzoyl)amino-1,4-benzodioxane-2-carboxylic acid and methyl ester thereof,
- 8-(p-isoheptyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-isooctyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(3,7-dimethyloctyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-(p-octyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane-7-carboxylic acid and methyl ester thereof
- and sodium salts thereof.
- 9. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a straight or branched alkenyloxy group of from 3 to 19 carbon atoms.
- 10. A compound according to claim 9, wherein the compound is selected from the group consisting of
- 8-[p-(2E-octenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(3-butenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(3Z-hexenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2Z-octenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2E-nonenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[N-methyl-N-[p-(2E-cctenyloxy)benzoyl]amino]-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2E-hexenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(3E-heptenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2E-octenyloxy)benzoyl.]amino-1,4-benzodioxane-2--carboxylic acid and methyl ester thereof,
- 8-[p-(2E-heptenyloxy)benzoyl]amino-2-(5-tetrazolyl)1,4-benzodioxane,
- 8-[p-(4-pentenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2E-decenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-geranyloxy benzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2E,7-octadienyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2E-pentenyloxy)benzoyl]amino-2-(5-tetrazoyl)-1,4-benzodioxane,
- 8-[p-(2E-butenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(3E-octenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(7-octenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2E,4E-octadienyoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[p-(2E-octenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane.
- and sodium salts thereof.
- 11. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a straight or branched alkynyloxy group of from 3 to 19 carbon atoms.
- 12. A compound according to claim 11, wherein the compound is selected from the group consisting of
- 8-[p-(2-octynyloxy)benzoyl]amino-2-(5-tetrazoyl)-1,4-benzodioxane,
- 8-[p-(2-octynyloxy)benzoyl]amino-1,4-benzodioxane-2-carboxylic acid and methyl ester thereof and
- 8-[p-(2-isooctynyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 13. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a straight or branched alkylthio group of from 1 to 19 carbon atom(s).
- 14. A compound according to claim 13, wherein the compound is selected from the group consisting of
- 8-(p-pentylthiobenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(m-pentylthiobenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(o-pentylthiobenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-(p-heptylthiobenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 15. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a straight or branched alkoxy group of from 1 to 18 carbon atom(s) being substituted by halogen atom(s).
- 16. A compound according to claim 15, wherein the compound is selected from the group consisting of
- 8-[p-(6-chlorohexyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(5-chloropentyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(4-chlorobutoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8[p-(7-chloroheptyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(8-chlorooctyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(9-chlorononyloxy)benzoyl]amino-2-(5-tetrazoyl)-1,4-benzodioxane and
- 8-[p-(5-bromopentyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane-2-carboxylic acid and methyl ester thereof
- and sodium salt thereof.
- 17. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a straight or branched alkyloxyalkyl group of from 2 to 19 carbon atoms.
- 18. A compound according to claim 17, wherein the compound is 8-[p-(hexyloxymethyl)benzoyl]amino-2-(5-tetraxzolyl)-1,4-benzodioxane or sodium salt thereof.
- 19. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a cycloalkyl group, cycloalkylalkyl group wherein the alkyl moiety is an alkyl group of from 1 to 8 carbon atom(s), or a cycloalkylalkyloxy group, wherein the alkyl moiety is an alkyl group of from 1 to 8 carbon atom(s), each of the groups represented by R.sup.6 having from 4 to 7 carbon atoms which may be unsubstituted or substituted by a etraight or branched alkyl group of from 1 to 8 carbon atom(s).
- 20. A compound according to claim 19, wherein the compound is selected from the group consisting of
- 8-[p-(cyclohexylmethoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(4-cyclohexylbutoxy)benozyl ]amino-2-(5-tetrazolyl)-1,4-benzodioxane, and
- 8-[p-(2-cyclohexylethoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 21. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a phenyl group, a phenylalkyl group wherein the alkyl moiety is an alkyl group of from 1 to 8 carbon atom(s), a phenylalkyloxy group wherein the alkyl moiety is an alkyl group of from 1 to 8 carbon atom(s), a phenylalkenyloxy group wherein the alkenyl moiety is an alkenyl group of from 2 to 8 carbon atoms, a naphthyl group, a naphthylalkyl group wherein the alkyl moiety is an alkyl group of from 1 to 8 carbon atom(s), a naphthylalkyloxy group wherein the alkyl moiety is an alkyl group of from 1 to 8 carbon atom(s), or a naphthylalkenyloxy group wherein the alkenyl moiety is an alkenyl group of from 2 to 8 carbon atoms which may be unsubstituted or substituted by a straight or branched alkyl group of from 1 to 8 carbon atom(s), one or more hydroxy group(s), one or more halogen atom(s) and/or one or more nitro group(s).
- 22. A compound according to claim 21, wherein the compound is selected from the group consisting of
- 8-[p-(p-butylphenyl)methoxybenoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(5-phenylpentyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(3-phenylpropoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(p-propylphenyl)methoxybenzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- 8-[p-(3-phenyl-2-propenyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(4-phenylbutoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(o-pentylphenyl)methoxybenzoyl amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(m-butylphenylmethoxybenzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-phenylmethoxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2-phenylethoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(4-phenylbutoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p[-2-(2-naphthyl)ethoxy]benozxyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- 8-[p-[3-(p-chlorophenyl)propoxy]benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[p-[4-(p-chlorophenyl)butoxy]benzoyl]amino-2-(5-tetraxzolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 23. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a straight or branched alkoxy, alkenyloxy or alkoxyalkoxy group of from 1 to 18 carbon atom(s) in which one or more carbon atoms are replaced by one or more carbonyl group(s), carbonyloyxy group(s) or hydroxy group(s).
- 24. A compound according to claim 23, wherein the compound is selected from the group consisting of
- 8-[p-(5-methoxycarbonylpentyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(6-acetyloxyhexyloxy)benzoyl]amino-2-(5-tetrazxolyl)-1,4-benzodioxane,
- 8-[p-(6-hydroxyhexyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benozdioxane,
- 8-[p-(2E-octenoyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-(p-octanoylbenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 25. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a straight or branched alkoxy group of from 1 to 17 carbon atom(s) which is substituted by a phenoxy or phenylthio group.
- 26. A compound according to claim 25, wherein the compound is selected form the group consisting of
- 8-[p-(3-phenylthiopropoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(3-phenoxypropoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2-phenylthioethoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[p-(2-phenoxyethoxy)benzoyl]amino-2-(5-tetraxzolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 27. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a straight or branched alkoxy group of from 1 to 18 carbon atom(s) which is substituted by one or more thiophene ring(s).
- 28. A compound according to claim 27, wherein the compound is selected from the group consisting of
- 8-[p-[2-(3-thienyl)ethoxy]benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[p-[4-(2-thienyl)butoxy]benzoyl]amino-2-(5-tetrazolyl)-1,4-benodioxane
- and sodium salts thereof.
- 29. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a straight or branched alkoxy group of from 1 18 carbon atom(s) which is substituted by one or more azido group(s), one or more nitro group(s) or one or more amino group(s) which may be unsubstituted or substituted by one or more straight or branched alkyl group(s) of from 1 to 6 carbon atom(s).
- 30. A compound according to claim 29, wherein the compound is selected from the group consisting of
- 8-[p-(5-azidopenyloxy)benozyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(5-dimethylaminopentyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(4-nitrobutoxy)benxzoyl amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2-azidoethoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[p-(4-azidobutoxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 31. A compound according to claim 4, wherein R.sup.5 is a hydrogen atom and R.sup.6 is a straight, or branched alkyl, alkenyl, alkoxy or alkenyloxy group substituted by two kinds of groups i.e. carbonyl group(s) and amino group(s).
- 32. A compound according to claim 31 wherein the compound is 8-[p-(2-octenoylamino)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane or sodium salt thereof.
- 33. A compound according to claim 4, wherein R.sup.5 and R.sup.6 are a halogen atom or a straight or branched alkyl, alkoxy or alkenyloxy group(s) of from 1 to 10 carbon atom(s), independently.
- 34. A compcund according to claim 33, wherein the compound is selected from the group consisting of
- 8-(p-pentyloxy-m-methoxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[p-(2E-octenyloxy)-m-chlorobenzoy]amino-2-(5-tetrazolyl)-1,4-benzodioxane and sodium salts thereof.
- 35. A compound according to claim 3, wherein R.sup.1 is a group of the general formula: ##STR407## wherein R.sup.5 and R.sup.6 have the same meaning as set forth in claim 1.
- 36. A compound according to claim 35, wherein the compound is 8-(2-naphthylcarbonyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane or sodium salt thereof.
- 37. A compound according to claim 2, wherein A is a vinylene group unsubstituted or substituted by straight or branched alkyl group(s) of from 1 to 6 carbon atom(s) or phenyl group(s) and T is an oxygen atom.
- 38. A compound according to claim 37, wherein in R.sup.1 is a group of the general formula: ##STR408## wherein R.sup.5 and R.sup.6 are the same meaning as set forth in claim 1.
- 39. A compound according to claim 38,
- wherein R.sup.5 is a hydrogen atom, and R.sup.6 is a hydrogen atom or a straight or branched alkyl group of from 1 to 20 carbon atom(s).
- 40. A compound according to claim 39, wherein the compound is selected from the group consisting of
- 8-(p-pentylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-pentylcinnamoyl)amino-1,4-benzodioxane- 2-carboxylic acid and methyl ester thereof,
- 8-(p-heptylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[N-methyl-[N-(p-pentylcinnamoyl)]amino]-2-(5-tetrazolyl(-1,4-benzodioxane
- 5-(p-pentylcinnamoyl)amino-2-(5-tetrazolyl)-7-chloro-1,4-benzodioxane,
- 8-(p-pentylcinnamoyl)amino-2-(5-tetrazolyl)-6-chloro-1,4-benzodioxane,
- 8-(p-ethylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-propylcinnamoyl)amino-2-(5-tetrazoyl)-1,4-benzodioxane,
- 8-(p-butylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-pentylcinnamoyl)amino-2-(5-tetrazolyl)-6-methyl-1,4-benzodioxane,
- 8-(o-pentylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(m-octylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-pentylcinnamoyl)amino-2-(5-tetrazoyl)-1,4-benzodioxane-5-carboxylic acid and methyl ester thereof,
- 5-(p-pentylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane-8-carboxylic acid and methyl ester thereof,
- 8-(p-hexylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-nonylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-pentylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane-6-carboxylic acid and methyl ester thereof,
- 5-(p-pentylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane-7-carboxylic acid and methyl ester thereof,
- 8-(p-octylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-decylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-isopropylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-isobutylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-isopentylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-pentyl-2-methylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-pentyl-3-methylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-(p-pentylcinnamoyl)amino-2-(5-tetrazolyl)methyl-1,4-benzodioxane
- and sodium salts thereof.
- 41. A compound according to claim 38, wherein R.sup.5 is a hydrogen atom, and R.sup.6 is a straight or branched alkoxy group of from 1 to 19 carbon atom(s).
- 42. A compound according to claim 41, wherein the compound is selected from the group consisting of
- 8-(p-pentyloxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(m-pentyloxycinnamoyl)amino-2-(5-tetrazolyl(-1,4-benzodioxane,
- 8-(o-pentyloxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-propoxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-butoxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-octyloxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-hexyloxycinnamoyl)amino-2-(5-tetrazolyl(-1,4-benzodioxane,
- 8-(p-heptyloxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-isopentyloxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-isohexyloxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(1-methylbutoxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-isoheptyloxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-isooctyloxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-isohexyloxy-2-methylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- -8-(p-isohexyloxy-2-phenylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 43. A compound according to claim 38,
- wherein R.sup.5 is a hydrogen atom, and R.sup.6 is a straight or branched alkenyloxy group of from 3 to 19 carbon atoms.
- 44. A compound according to claim 43, wherein the compound is selected from the group consisting of
- 8-[p-(2E-octenyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2-propenyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(3-butenyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(3Z-hexenyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2Z-pentenyloxycinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxan,
- 8-[p-(2E-nonenyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(3E-heptenyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2E-heptenyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2E-hexenyloxy)cinnamoyl]amino-2-(5-terrazolyl)-1,4-benzodioxane,
- 8-[p-(2E-pentenyloyy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(4-pentenyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2E-butenyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[p-(2E-decenyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 45. A compound according to claim 38,
- wherein R.sup.5 is a hydrogen atom, and R.sup.6 is a straight or branched alkynyloxy group of from 3 to 19 carbon atoms.
- 46. A compound according to claim 45, wherein the compound is selected from the group consisting of
- 8-[p-(2-octynyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[p-(2-pentynyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 47. A compound according to claim 38,
- wherein R.sup.5 is a hydrogen atom, and R.sup.6 is a straight or branched alkylthio group of from 1 to 19 carbon atom(s).
- 48. A compound according to claim 47, wherein the compound is selected from the group consisting of
- 8-(p-pentylthiocinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8(m-pentylthiocinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-(o-pentylthiocinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 49. A compound according to claim 38,
- wherein R.sup.5 is a hydrogen atom, and R.sup.6 is a straight or branched alkoxy group of from 1 to 18 carbon atom(s) being substituted by halogen atom(s).
- 50. A compound according to claim 49, wherein the compound is selected from the group consisting of
- 8-[p-(6-chlorohexyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(4-chlorobutoxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(5-chloropentyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[p-(7-chloroheptyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 51. A compound according to claim 38, wherein R.sup.5 is a hydrogen atom, and R.sup.6 is a straight or branched alkyloxyalkyl group of from 2 to 19 carbon atoms.
- 52. A ccmpound according to claim 51,
- wherein the compound is 8-(p-isopentyloxymethylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane or sodium salt thereof.
- 53. A compound according to claim 38,
- wherein R.sup.5 is a hydrogen atom, and R.sup.6 is a cycloalkyl, cycloalkylalkyl (wherein alkyl moiety is a group of from 1 to 8 carbon atom(s) or cycloalkylalkyloxy (wherein alkyl moiety is a group of from 1 to 8 carbon atom(s) of from 4 to 7 carbon atoms being unsubstituted or substituted by a straight or branched alkyl group of from 1 to 8 carbon atom(s).
- 54. A compound according to claim 53, wherein the compound is selected from the group consisting of
- 8-(p-cyclohexylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-cyclohexylmethoxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(4-cyclohexylbutoxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[p-(2-cyclohexylethoxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 55. A compound according to claim 38, wherein R.sup.5 is a hydrogen atom, and R.sup.6 is a phenyl group, a phenylalkyl group wherein the alkyl moiety is an alkyl group of from 1 to 8 carbon atom(s), a phenylalkyloxy group whereien the alkyl moiety is an alkyl group of from 1 to 8 carbon atom(s) or a phenylakenyloxy group wherein the alkenyl moiety is an alkenyl group of from 2 to 8 carbon atoms, which may be unsubstituted or substituted by one or more straight or branched alkyl group(s) of from 1 to 8 carbon atom(s), one or moe hydroxy group(s), one or more halogen atom(s) and/or one or more nitro group(s).
- 56. A compcund according to claim 55, wherein the compound is selected from the group consisting of
- 8-(p-phenylmethylcinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(p-phenylmethoxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(2-phenylethoxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(4-phenylbutoxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[p-(5-phenylpentyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[p-(3-phenylpropoxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 57. A compound according to claim 38,
- wherein R.sup.5 is a hydrogen atom, and R.sup.6 is a straight or alkoxy, alkenyloxy or alkoxyalkoxy group of from 1 to 18 carbon atoms(s) in which one or more carbon atoms are replaced by one or more carbonyl group(s), carbonyloxy group(s) or hydroxy group(s).
- 58. A compound according to claim 57,
- wherein the compound is 8-[p-(6-acetyloxyhexyloxy)cinnamoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane or sodium salts thereof.
- 59. A compound according to claim 38,
- wherein R.sup.5 is a hydrogen atom, and R.sup.6 is a straight or branched alkoxy group of from 1 to 18 carbon atom(s) which is substituted by thiophene ring(s).
- 60. A compound according to claim 59,
- wherein the compound is 8-[p-[2-(2-thienyl)ethoxy]cinnamoyl]-amino-2-(5-tetrazolyl)-1,4-benzodioxane or sodium salts thereof.
- 61. A compound according to claim 38, wherein R.sup.5 and R.sup.6 are a halogen atom or a straight or branched alkyl, alkoxy or alkenyloxy group of from 1 to 10 carbon atom(s), independently.
- 62. A compound according to claim 61, wherein the compound is selected from the group consisting of
- 8-(m,p-dimethoxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-(m-methoxy-p-pentyloxycinnamoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-(p-pentyloxy-m-chlorocinnamoyl)amino-2-(5-tetrazoylyl)-1,4-benzodioxane
- and sodium salts thereof.
- 63. A compound according to claim 37, wherein R.sup.1 is a group of the general formula: ##STR409## (wherein R.sup.5 and R.sup.6 have the same meaning as set forth in claim 1.
- 64. A compound according to claim 63,
- wherein the compound is 8-[3-(5-indanyl)acryloyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane or scdium salt thereof.
- 65. A compound according to claim 37, wherein R.sup.1 is a straight or branched alkyl, alkenyl or alkynyl group of from 1 to 20 carbon atom(s).
- 66. A compound according to claim 65,
- wherein the compound is N-(2-hexadecenoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane or sodium salt thereof.
- 67. A compound according to claim 2, wherein A is a methylene or ethylene group, and symbol T is an oxygen atom.
- 68. A compound according to claim 67, wherein the compound is selected from the group consisting of
- 8-(p-pentylphenylacetyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[3-(p-pentylphenyl)propionyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 69. A compound according to claim 2, wherein A is an ethynylene or butadienylene group, and T is an oxygen atom.
- 70. A compound according to claim 69, wherein the compound is selected from the group consisting of
- 8-(p-hexylphenylpropioloyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane,
- 8-[5-(p-propoxyphenyl)penta-2E,4E-dienoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane and
- 8-[5-(p-butylphenyl)penta-2E,4E-dienoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane
- and sodium salts thereof.
- 71. A compound according to claim 2, wherein A is a single bond or vinylene group, and T is a sulphur atom.
- 72. A compound according to claim 71, wherein the compound is 8-(p-heptyloxybenzothioyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane or sodium salt thereof.
- 73. A compound according to claim 1, wherein B is a 2,3,5,6-tetrahydro-1,4-dithiane ring (i.e. the formula: ##STR410##
- 74. A compound according to claim 73, wherein A is a single bond or vinylene group which may be unsubstituted or substituted by one or more straight or branched alkyl group(s) of from 1 to 6 carbon atom(s) or one or more phenyl group(s) and T is an oxygen atom.
- 75. A compound according to claim 74, wherein R.sup.1 is a group of the general formula: ##STR411## wherein R.sup.5 and R.sup.6 have the same meaning as set forth in claim 1.
- 76. A compound according to claim 75, wherein the compound is selected from the group consisting of
- 8-(p-pentylcinnamoyl)amino-2-(5-tetrazolyl)-2,3-dihydro-14-dithianaphthalene and
- 5-(p-pentylcinnamoyl)amino-2-(5-tetrazolyl)-2,3-dihydro-1,4-dithianaphthalene
- and sodium salts thereof.
- 77. A pharmaceutical composition which contains, as an active ingredient, at least one compound of the general formula (I) as defined in claim 1, together with a pharmaceutically acceptable carrier and/or coating.
Priority Claims (3)
Number |
Date |
Country |
Kind |
59-172570 |
Aug 1984 |
JPX |
|
59-243412 |
Dec 1984 |
JPX |
|
59-246363 |
Dec 1984 |
JPX |
|
Parent Case Info
This is a division of application Ser. No. 06/767,538, filed Aug. 20, 1985, now U.S. Pat. No. 4,780,469.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4205076 |
Durham et al. |
May 1980 |
|
4205079 |
Durham et al. |
May 1980 |
|
Divisions (1)
|
Number |
Date |
Country |
Parent |
767538 |
Aug 1985 |
|