N-[(Amino)Alkyl]-1-pyrrolidine, 1-piperidine and 1-homopiperidinecarboxamides (and thiocarboxamides) with sulphur linked substitution in the 2, 3 or 4-position

Claim 2

A compound of general formula I: wherein: n is zero, one or two; Y represents oxygen or sulphur; each of A, A 1 and A 2 independently represents straight or branched chain alkylene having 1 to 8 carbon atoms and each of p and d independently is zero or one with the proviso that when the -(A 1 ) p -X-(A 2 ) d -Q radical is in the 2-position, p is one; X represents -S-, -S(O)- or -S(0) 2 -; each of R, R and R 2 independently represents hydrogen, loweralkyl (1-8 carbons), phenyl, cycloalkyl (1-9 carbons) or phenylalkyl (7-14 carbons) or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic residue which is: a) 1-pyrrolidino, b) 1-piperidino, c) 4-morpholino, d) 1-piperazino, e) a heterocycle of a) to d) substituted by a methyl, ethyl, phenyl or phenylloweralkyl, f) 2,6- (loweralkyl) 2 -piperidino, g) 4-hydroxy-4-phenylpiperidino, h) 4-cyano-4-phenylpiperidino, or, i) 4-phenyl-1,2,3,6-tetrahydropyridino, Q represents: 1) 1 or 2-naphthyl, 2) 2,3-dihydro-lH-inden-4-yl or 2,3-dihydro-1H-inden-5-yl, 3) biphenyl, 4) phenyl, wherein R 3 represents fluorine, chlorine, bromine, iodine, loweralkyl (1-8 carbons), loweralkoxy (1-8 carbons), trifluoromethyl, hydroxy, cyano or nitro, R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy or nitro and R 5 represents hydrogen, methyl, ethyl, methoxy, ethoxy, methylthio and phenylthio, wherein R 6 represents - NR 7 R 8 , -C(O)NR 7 R 8 , -B-(CH 2 ) b NR 7 R 8 or -B-(CH 2 ) b OR 7 wherein B represents -0-, -S-, -S(O)- or -S(0) 2 -, b is 2 or 3 and each of R and R 8 independently represents hydrogen, loweralkyl (1-8 carbons), wherein R 9 represents -SR 10 , -S(O)R 10 or -S(O 2 )R 10 wherein R 10 represents loweralkyl (1-8 carbons) or phenyl with the proviso that X must be -S(O) 2 -, wherein A3 represents straight or branched chain alkylene (2-8 carbons) and G represents loweralkoxy (1-8 carbons) or -NR 11 R 12 wherein each of R 11 and R 12 independently represent hydrogen, loweralkyl (1 to 8 carbons), phenyl or phenyl-loweralkyl (7-14 carbons), or a pharmaceutically acceptable acid addition salt or hydrate thereof.

Claim 3

3-[4-(Chlorophenyl)thio]-N-[2-(diethylamino)ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)thio]-N-[2-(dimethylamino)-ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)thio]-N-[2-(dimethylamino)-ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)sulphinyl]-N-[2-(diethylamino)ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)sulphonyl]-N-[2-(diethylamino) ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)sulphonyl]-N-[2-(dimethylamino) ethyl]-l-pyrrolidinecarboxamide, 3-(phenylsulphonyl)-N-[2-(diethylamino)ethyl]-1-pyrrolidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[(4-methylphenyl)thio]-1-pyrrolidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[(4-methylphenyl) sulphonyl]-1-pyrrolidinecarboxamide, N-[3-(diethylamino)propyl]-3-(phenylsulphonyl)-1-pyrrolidinecarboxamide, 3-[(3,4-dichlorophenyl)sulphonyl]-N-(2-(dimethyl- amino)ethyl]-1-pyrrolidinecarboxamide, 3-[(3,4-dichlorophenyl)sulphonyl]-N-[2-(diethylamino)ethyl]-1-pyrrolidinecarboxamide, 3-[(3,4-dichlorophenyl)thio]-N-[2-(diethylamino) ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)sulphonyl]-N-[2-(dimethylamino) ethyll-1-piperidinecarboxamide, 3-[(4-chlorophenyl)thio]-N-[2-(dimethylamino) ethyl]-1-piperidinecarboxamide, 3-[(3-chlorophenyl)sulphonyl]-N-[2-(dimethylamino) ethyl]-1-piperidinecarboxamide, 3-[(3-chlorophenyl)thio]-N-[2-(dimethylamino) ethyl]-1-piperidinecarboxamide, 3-[(4-chlorophenyl)sulphinyl]-N-[2-(dimethylamino) ethyl]-1-piperidinecarboxamide, 3-[(4-chlorophenyl)sulphonyl]-N-[2-(diethylamino) ethyl]3-1-pyrrolidinecarboxamide, N-[2-(diethylamino)ethyl]-3-(phenylsulphonyl)-1-piperidinecarboxamide, N-[2-(dimethylamino)ethyl]-3-(phenylsulphdnyl)-1-piperidinecarboxamide, N-[2-(diethylamino)ethyl]-3-(phenylsulphonyl)-1-piperidinecarbothioamide, N-[2-(diethylamino)ethyl]-3-[(4-methylphenyl) sulphonyl]-1-piperidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[(4-fluorophenyl) sulphonyl]-1-piperidinecarboxamide, N-[3-(diethylamino)propyl]-3-(phenylsulphonyl)-1-piperidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[(4-methoxyphenyl) sulphonyl]-1-piperidinecarboxamide, N-[2-[bis(1-methylethyl)amino]ethyl]-3-(phenylsulphonyl)-1-piperidinecarboxamide, 4-[(4-chlorophenyl)thio]-N-[2-(dimethylamino) ethyl]-l-piperidinecarboxamide, 4-[4-(chlorophenyl)sulphonyl]-N-[2-(dimethyl amino)ethyl]-1-piperidinecarboxamide, 4-[(4-chlorophenyl)sulphinyl]-N-[2-(dimethyl amino)ethyll-l-piperidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[[4-[2-(dimethylamino) ethoxy]phenyl]sulphonyl]-1-piperidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[[4-(2-methoxy ethoxy]phenyl]sulphonyl]-1-piperidinecarboxamide, 3-[[4-[2-(diethylamino)ethoxy]phenyl]sulphonyl]-N-[2-(diethylamino)ethyl]-1-piperidinecarboxamide, N-[2-(dimethylamino)ethyl]-3-[(phenylsulphonyl) methyl]-1-piperidinecarboxamide, or N-[2-(diethylamino)ethyl]-3-[(phenylsulphonyl) methyl]-1-piperidinecarboxamide or a pharmaceutically acceptable acid addition salt or hydrate of any of such compounds.

Claim 4

3-[4-(Chlorophenyl)thio]-N-[2-(diethylamino)ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)thio]-N-[2-(dimethylamino)-ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)thio]-N-[2-(dimethylamino)-ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)sulphinyl]-N-[2-(diethylamino)ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)sulphonyl]-N-[2-(diethylamino) ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)sulphonyl]-N-[2-(dimethylamino) ethyl]-l-pyrrolidinecarboxamide, 3-(phenylsulphonyl)-N-[2-(diethylamino)ethyl]-1-pyrrolidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[(4-methylphenyl)thio]-1-pyrrolidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[(4-methylphenyl) sulphonyl]-1-pyrrolidinecarboxamide, N-[3-(diethylamino)propyl]-3-(phenylsulphonyl)-1-pyrrolidinecarboxamide, 3-[(3,4-dichlorophenyl)sulphonyl]-N-(2-(dimethyl- amino)ethyl]-1-pyrrolidinecarboxamide, 3-[(3,4-dichlorophenyl)sulphonyl]-N-[2-(diethylamino)ethyl]-1-pyrrolidinecarboxamide, 3-[(3,4-dichlorophenyl)thio]-N-[2-(diethylamino) ethyl]-1-pyrrolidinecarboxamide, 3-[(4-chlorophenyl)sulphonyl]-N-[2-(dimethylamino) ethyll-1-piperidinecarboxamide, 3-[(4-chlorophenyl)thio]-N-[2-(dimethylamino) ethyl]-1-piperidinecarboxamide, 3-[(3-chlorophenyl)sulphonyl]-N-[2-(dimethylamino) ethyl]-1-piperidinecarboxamide, 3-[(3-chlorophenyl)thio]-N-[2-(dimethylamino) ethyl]-1-piperidinecarboxamide, 3-[(4-chlorophenyl)sulphinyl]-N-[2-(dimethylamino) ethyl]-1-piperidinecarboxamide, 3-[(4-chlorophenyl)sulphonyl]-N-[2-(diethylamino) ethyl]3-1-pyrrolidinecarboxamide, N-[2-(diethylamino)ethyl]-3-(phenylsulphonyl)-1-piperidinecarboxamide, N-[2-(dimethylamino)ethyl]-3-(phenylsulphdnyl)-1-piperidinecarboxamide, N-[2-(diethylamino)ethyl]-3-(phenylsulphonyl)-1-piperidinecarbothioamide, N-[2-(diethylamino)ethyl]-3-[(4-methylphenyl) sulphonyl]-1-piperidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[(4-fluorophenyl) sulphonyl]-1-piperidinecarboxamide, N-[3-(diethylamino)propyl]-3-(phenylsulphonyl)-1-piperidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[(4-methoxyphenyl) sulphonyl]-1-piperidinecarboxamide, N-[2-[bis(1-methylethyl)amino]ethyl]-3-(phenylsulphonyl)-1-piperidinecarboxamide, 4-[(4-chlorophenyl)thio]-N-[2-(dimethylamino) ethyl]-l-piperidinecarboxamide, 4-[4-(chlorophenyl)sulphonyl]-N-[2-(dimethyl amino)ethyl]-1-piperidinecarboxamide, 4-[(4-chlorophenyl)sulphinyl]-N-[2-(dimethyl amino)ethyll-l-piperidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[[4-[2-(dimethylamino) ethoxy]phenyl]sulphonyl]-1-piperidinecarboxamide, N-[2-(diethylamino)ethyl]-3-[[4-(2-methoxy ethoxy]phenyl]sulphonyl]-1-piperidinecarboxamide, 3-[[4-[2-(diethylamino)ethoxy]phenyl]sulphonyl]-N-[2-(diethylamino)ethyl]-1-piperidinecarboxamide, N-[2-(dimethylamino)ethyl]-3-[(phenylsulphonyl) methyl]-1-piperidinecarboxamide, or N-[2-(diethylamino)ethyl]-3-[(phenylsulphonyl) methyl]-1-piperidinecarboxamide or a pharmaceutically acceptable acid addition salt or hydrate of any of such compounds.

Claim 5

The use of a compound of general formula I: wherein: n is zero, one or two; Y represents oxygen or sulphur; each of A, A and A 2 independently represents straight or branched chain alkylene having 1 to 8 carbon atoms and each of p and d independently is zero or one with the proviso that when the -(A 1 ) p -X-(A 2 ) d -Q radical is in the 2-position, p is one; X represents -S-, -S(0)-, or -S(0) 2 -; each of R , R1 and R 2 independently represents hydrogen, loweralkyl (1-8 carbons), phenyl, cycloalkyl (1-9 carbons) or phenylalkyl (7-14 carbons) or Rand R 2 taken together with the adjacent nitrogen atom form a heterocyclic residue which is: a) 1-pyrrolidino, b) 1-piperidino, c) 4-morpholino, d) I-piperazino, e) a heterocycle of a) to d) substituted by a methyl, ethyl, phenyl or phenylloweralkyl, f) 2,6-(loweralkyl) 2 -piperidino, g) 4-hydroxy-4-phenylpiperidino, h) 4-cyano-4-phenylpiperidino, or, i) 4-phenyl-1,2,3,6-tetrahydropyridino, Q represents:- 1) 1 or 2-naphthyl, 2) 2,3-dihydro-lH-inden-4-yl or 2,3-dihydro-1H-inden-5-yl, 3) biphenyl, 4) phenyl, wherein R 3 represents fluorine, chlorine, bromine, iodine, loweralkyl (1-8 carbons), loweralkoxy (1-8 carbons), trifluoromethyl, hydroxy, cyano or nitro, R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy or nitro and R 5 represents hydrogen, methyl, ethyl, methoxy, ethoxy, methylthio or phenylthio, wherein R 6 represents -NR 7 R 8 , -C(O)NR 7 R 8 , -B-(CH 2 ) b NR 7 R 8 or -B-(CH 2 ) b OR 7 wherein B represents -O-, -S-, -S(O)- or -S(0) 2 -, b is 2 or 3 and each of R 7 and R 8 independently represents hydrogen or loweralkyl (1-8 carbons), wherein R 9 represents -SR 10 , -S(O)R 10 or -S(O 2 )R 10 wherein R represents loweralkyl (1-8 carbons) or phenyl with the proviso that X must be -S(0) 2 -, or, 8) wherein A3 represents straight or branched chain alkylene (-2-8 carbons) and G represents hydrogen, loweralkoxy (1-8 carbons) or -NR 11 R 12 wherein each of R 11 and R 12 independently represents loweralkoxy (1-8 carbons), phenyl or phenyl-loweralkyl (7-14 carbons), or a pharmaceutically acceptable acid addition salt or hydrate thereof, in the manufacture of a medicament for treating cardiac arrhythmias.

Claim 6

The use of a compound of general formula I: wherein: n is zero, one or two; Y represents oxygen or sulphur; each of A, A and A 2 independently represents straight or branched chain alkylene having 1 to 8 carbon atoms and each of p and d independently is zero or one with the proviso that when the -(A 1 ) p -X-(A 2 ) d -Q radical is in the 2-position, p is one; X represents -S-, -S(0)-, or -S(0) 2 -; each of R , R1 and R 2 independently represents hydrogen, loweralkyl (1-8 carbons), phenyl, cycloalkyl (1-9 carbons) or phenylalkyl (7-14 carbons) or Rand R 2 taken together with the adjacent nitrogen atom form a heterocyclic residue which is: a) 1-pyrrolidino, b) 1-piperidino, c) 4-morpholino, d) I-piperazino, e) a heterocycle of a) to d) substituted by a methyl, ethyl, phenyl or phenylloweralkyl, f) 2,6-(loweralkyl) 2 -piperidino, g) 4-hydroxy-4-phenylpiperidino, h) 4-cyano-4-phenylpiperidino, or, i) 4-phenyl-1,2,3,6-tetrahydropyridino, Q represents:- 1) 1 or 2-naphthyl, 2) 2,3-dihydro-lH-inden-4-yl or 2,3-dihydro-1H-inden-5-yl, 3) biphenyl, 4) phenyl, wherein R 3 represents fluorine, chlorine, bromine, iodine, loweralkyl (1-8 carbons), loweralkoxy (1-8 carbons), trifluoromethyl, hydroxy, cyano or nitro, R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy or nitro and R 5 represents hydrogen, methyl, ethyl, methoxy, ethoxy, methylthio or phenylthio, wherein R 6 represents -NR 7 R 8 , -C(O)NR 7 R 8 , -B-(CH 2 ) b NR 7 R 8 or -B-(CH 2 ) b OR 7 wherein B represents -O-, -S-, -S(O)- or -S(0) 2 -, b is 2 or 3 and each of R 7 and R 8 independently represents hydrogen or loweralkyl (1-8 carbons), wherein R 9 represents -SR 10 , -S(O)R 10 or -S(O 2 )R 10 wherein R represents loweralkyl (1-8 carbons) or phenyl with the proviso that X must be -S(0) 2 -, or, 8) wherein A3 represents straight or branched chain alkylene (-2-8 carbons) and G represents hydrogen, loweralkoxy (1-8 carbons) or -NR 11 R 12 wherein each of R 11 and R 12 independently represents loweralkoxy (1-8 carbons), phenyl or phenyl-loweralkyl (7-14 carbons), or a pharmaceutically acceptable acid addition salt or hydrate thereof, in the manufacture of a medicament for treating cardiac arrhythmias.

Claim 7

The use of a compound as defined in Claim 2 in the manufacture of a medicament for treating cardiac arrhthmias.

Claim 8

A compound as defined in Claim 1 or 2 for use in medicine, for example cardiovascular medicine.

Claim 9

A therapeutic composition for the treatment of cardiac arrhythmias comprising a) an effective amount of a compound of general formula I wherein: n is zero, one or two; Y represents oxygen or sulphur, each of A, A 1 and A 2 independently represents straight or branched chain alkylene having 1 to 8 carbon atoms,each of p and d independently is zero or one with the proviso that when the -(A 1 ) p -X-(A 2 ) d -Q radical is in the 2-position, p is one; X represents -S-, -S(O)- or -S(O) 2 -, each of R , R 1 and R 2 independently represents hydrogen, loweralkyl (1-8 carbons), phenyl, cycloalkyl (1-9 carbons) or phenylalkyl (7-14 carbons), or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic residue which is: a) I-pyrrolidino, b) 1-piperidino, c). 4-morpholino, d) I-piperazino, e) a heterocyclic of a) to d) substituted by a methyl, ethyl, phenyl or phenylloweralkyl, f) 2,6-(loweralkyl) 2 -piperidino, g) 4-hydroxy-4-phenylpiperidino, h) cyano-4-phenylpiperidino, or, i) 4-phenyl-1,2,3,6-tetrahydropyridino, Q represents: 1) 1 or 2 naphthyl, 2) 2,3-dihydro-lH-inden-4-yl or 2,3-dihydro-1H-inden-5-yl, 3) biphenyl, 4) phenyl, 5) wherein R 3 represents fluorine, chlorine, bromine, iodine, loweralkyl (1-8 carbons), loweralkoxy (1-8 carbons), trifluoromethyl, hydroxy, cyano or nitro, R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy or nitro and R 5 represents hydrogen, methyl, ethyl, methoxy, ethoxy, methylthio or phenylthio, wherein R 6 represents -NR 7 R 8 , - C ( 0 ) NR 7 R 8 , -B-(CH 2 ) b NR 7 R 8 or -B-(CH 2 ) b OR 7 wherein B represents -O-, -S-, -S(O)- or -S(O) 2 -, b is 2 or 3 and each of R 7 and R 8 independently represents hydrogen, loweralkyl (1-8 carbons), wherein R 9 represents -SR 10 , -S(O)R 10 , or -S(O 2 )R 10 wherein R 10 represents loweralkyl (1-8 carbons) and phenyl with the proviso that X must be -S(0) 2 -, or, 8) wherein A3 represents straight or branched chain alkylene (2-8 carbons) and G represents loweralkoxy (1-8 carbons) or -NR 11 R 12 wherein each of R 11 and R 12 independently represent hydrogen, loweralkyl (1-8 carbons), phenyl or phenyl-loweralkyl (7-14 carbons), or a pharmaceutically acceptable acid addition salt or hydrates thereof, and b) a pharmaceutically acceptable carrier therefor.

Claim 10

A therapeutic composition for the treatment of cardiac arrhythmias comprising a) an effective amount of a compound of general formula I wherein: n is zero, one or two; Y represents oxygen or sulphur, each of A, A 1 and A 2 independently represents straight or branched chain alkylene having 1 to 8 carbon atoms,each of p and d independently is zero or one with the proviso that when the -(A 1 ) p -X-(A 2 ) d -Q radical is in the 2-position, p is one; X represents -S-, -S(O)- or -S(O) 2 -, each of R , R 1 and R 2 independently represents hydrogen, loweralkyl (1-8 carbons), phenyl, cycloalkyl (1-9 carbons) or phenylalkyl (7-14 carbons), or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic residue which is: a) I-pyrrolidino, b) 1-piperidino, c). 4-morpholino, d) I-piperazino, e) a heterocyclic of a) to d) substituted by a methyl, ethyl, phenyl or phenylloweralkyl, f) 2,6-(loweralkyl) 2 -piperidino, g) 4-hydroxy-4-phenylpiperidino, h) cyano-4-phenylpiperidino, or, i) 4-phenyl-1,2,3,6-tetrahydropyridino, Q represents: 1) 1 or 2 naphthyl, 2) 2,3-dihydro-lH-inden-4-yl or 2,3-dihydro-1H-inden-5-yl, 3) biphenyl, 4) phenyl, 5) wherein R 3 represents fluorine, chlorine, bromine, iodine, loweralkyl (1-8 carbons), loweralkoxy (1-8 carbons), trifluoromethyl, hydroxy, cyano or nitro, R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy or nitro and R 5 represents hydrogen, methyl, ethyl, methoxy, ethoxy, methylthio or phenylthio, wherein R 6 represents -NR 7 R 8 , - C ( 0 ) NR 7 R 8 , -B-(CH 2 ) b NR 7 R 8 or -B-(CH 2 ) b OR 7 wherein B represents -O-, -S-, -S(O)- or -S(O) 2 -, b is 2 or 3 and each of R 7 and R 8 independently represents hydrogen, loweralkyl (1-8 carbons), wherein R 9 represents -SR 10 , -S(O)R 10 , or -S(O 2 )R 10 wherein R 10 represents loweralkyl (1-8 carbons) and phenyl with the proviso that X must be -S(0) 2 -, or, 8) wherein A3 represents straight or branched chain alkylene (2-8 carbons) and G represents loweralkoxy (1-8 carbons) or -NR 11 R 12 wherein each of R 11 and R 12 independently represent hydrogen, loweralkyl (1-8 carbons), phenyl or phenyl-loweralkyl (7-14 carbons), or a pharmaceutically acceptable acid addition salt or hydrates thereof, and b) a pharmaceutically acceptable carrier therefor.

Claim 11

A pharmaceutical composition comprising a compound as defined in Claim 2 and a pharmaceutically acceptable carrier therefore.

Claim 12

A process for preparing a compound of Formula I as defined in Claim 1, the process comprising either A) reacting (i) a compound of general formula II: wherein n, A 1 , A 2 , p, d, X and Q are as defined for Formula I with (ii) a compound preparable by the reaction of an imidazole of the formula: wherein Y is oxygen or sulphur, and a compound having the formula NH 2 -A-NR 1 R 2 wherein A, R 1 and R 2 are as defined for Formula I with the proviso that R 1 and R 2 are not hydrogen, to produce a compound of Formula I with the proviso that 2 R 1 and R are not hydrogen; or B) reacting (i) a compound of general formula II as defined for (A) above with (ii) a compound preparable by the reaction of phosgene or thiophosgene with a compound having the formula RNH-A- NR 1 R 2 wherein A, R, R 1 and R 2 are as defined for Formula I with the proviso that when R 2 is hydrogen, R and R 1 are identical radicals, to produce a compound of Formula I with the proviso that when R 2 is hydrogen, R and R are identical radicals; and C) optionally after either (A) or (B) converting a compound of Formula I so formed into a further compound of Formula I or a salt thereof.

Claim 13

A process as claimed in Claim 8 for producing a compound as defined in Claim 2.

Claim 14

A compound of Formula II: wherein: n is zero, one or two; each of A 1 and A 2 independently represents straight or branched chain alkylene having 1 to 8 carbon atoms and each of p and d independently is zero or one with the proviso that when the -(A 1 )p-X-(A 2 ) d -Q radical is in the 2-position, p is one; X represents -S-, --S(O)- or -S(O) 2 -; Q represents 1) 1 or 2-naphthyl, 2) 2,3-dihydro-lH-inden-4-yl or 2,3-dihydro- lH-inden-5-yl, 3) biphenyl, 4) phenyl, wherein R 3 represents fluorine, chlorine, bromine, iodine, loweralkyl (1-8 carbons), loweralkoxy (1-8 carbons), trifluoromethyl, hydroxy, cyano or nitro, R represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy or nitro and R 5 represents hydrogen, methyl, ethyl, methoxy, ethoxy, methylthio and phenylthio, wherein R 6 represents -NR 7 R 8 , -C(O)NR 7 R 8 , -B-(CH 2 ) b NR 7 R 8 or -B-(CH 2 ) b OR 7 wherein B represents -0-, -S-, -S(O)- or -S(O) 2 -, b is 2 or 3 and each of R 7 and R 8 independently represents hydrogen, loweralkyl (1-8 carbons), wherein R 9 represents -SR 10 , -S(O)R 10 and -S(O 2 )R 10 wherein R 10 represents loweralkyl (1-8 carbons) and phenyl with the proviso that X must be -S(0) 2 -, or, 8) wherein A3 represents straight or branched chain alkylene (2-8 carbons) and G represents loweralkoxy (1-8 carbons) or -NR 11 R 12 wherein each of R 11 and R 12 independently represents hydrogen,loweralkyl (1-8 carbons), phenyl or phenyl-loweralkyl, (7-14 carbons), or an acid addition salt or hydrate thereof.

Claim 15

A compound of Formula II: wherein: n is zero, one or two; each of A 1 and A 2 independently represents straight or branched chain alkylene having 1 to 8 carbon atoms and each of p and d independently is zero or one with the proviso that when the -(A 1 )p-X-(A 2 ) d -Q radical is in the 2-position, p is one; X represents -S-, --S(O)- or -S(O) 2 -; Q represents 1) 1 or 2-naphthyl, 2) 2,3-dihydro-lH-inden-4-yl or 2,3-dihydro- lH-inden-5-yl, 3) biphenyl, 4) phenyl, wherein R 3 represents fluorine, chlorine, bromine, iodine, loweralkyl (1-8 carbons), loweralkoxy (1-8 carbons), trifluoromethyl, hydroxy, cyano or nitro, R represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy or nitro and R 5 represents hydrogen, methyl, ethyl, methoxy, ethoxy, methylthio and phenylthio, wherein R 6 represents -NR 7 R 8 , -C(O)NR 7 R 8 , -B-(CH 2 ) b NR 7 R 8 or -B-(CH 2 ) b OR 7 wherein B represents -0-, -S-, -S(O)- or -S(O) 2 -, b is 2 or 3 and each of R 7 and R 8 independently represents hydrogen, loweralkyl (1-8 carbons), wherein R 9 represents -SR 10 , -S(O)R 10 and -S(O 2 )R 10 wherein R 10 represents loweralkyl (1-8 carbons) and phenyl with the proviso that X must be -S(0) 2 -, or, 8) wherein A3 represents straight or branched chain alkylene (2-8 carbons) and G represents loweralkoxy (1-8 carbons) or -NR 11 R 12 wherein each of R 11 and R 12 independently represents hydrogen,loweralkyl (1-8 carbons), phenyl or phenyl-loweralkyl, (7-14 carbons), or an acid addition salt or hydrate thereof.

Claim 16

3-(Phenylsulphonyl)piperidine, 3-[(4-chlorophenyl)sulphinyl]piperidine, 3-[(4-chlorophenyl)thio]piperidine, 4-[(4-chlorophenyl)thio]piperidine, 4-[(4-chlorophenyl)sulphinyl]piperidine, or 4-[(4-chlorophenyl)sulphonyl]piperidine or and acid addition salt of any of such compounds.

Claim 17

3-(Phenylsulphonyl)piperidine, 3-[(4-chlorophenyl)sulphinyl]piperidine, 3-[(4-chlorophenyl)thio]piperidine, 4-[(4-chlorophenyl)thio]piperidine, 4-[(4-chlorophenyl)sulphinyl]piperidine, or 4-[(4-chlorophenyl)sulphonyl]piperidine or and acid addition salt of any of such compounds.

Claim 18

1 2. A process for preparing a compound of Formula II as defined in Claim 10, the process comprising hydrolyzing a compound of the formula wherein L represents a non-interfering leaving group, n , A 1 , A 2 , p, d and Q are as defined in Claim 10 and X' represents -S- or -S(O) 2 - to form a compound of Formula II except that X represents -S- or -S(O) 2 -. optionally, in the case of where X represents -S-oxidizing the compound of Formula II so formed to give a compound where X represents -S(O)- or -S(0) 2 -, and optionally forming a salt of such a compound.

Claim 19

A process as claimed in Claim 12 wherein L represents a carboxyphenyl group or a group -S(0) 2 W wherein W represents alkyl phenyl or substituted phenyl.

Claim 20

A process as claimed in Claim 12 or 13 for preparing a compound as defined in Claim 1-1.