Abstract: This appliciation discloses a process for preparing a lactone of general formula (I), where R is an optionally substituted phenyl group or an optionally substituted mono- or bicyclic heteroaryl radical which process comprises reacting an anion of a malonate of formula (II) with an ethylene compound of formula (III) Y--CH.sub.2 --CH.sub.2 OZ, to give a compound of formula (IV) and hydrolysing the compound of formula (IV) to give a lactone of formula (I). The lactones are of use as intermediates for preparing 5-HT.sub.1A binding agents.

Abstract: The invention concerns compounds of formula I ##STR1## or a salt thereof, wherein R.sup.1 and R.sup.2 each independently represent hydrogen, lower alkyl, lower alkoxy, carboxyloweralkyl, carboxy, hydroxyloweralkyl, halogen, haloloweralkyl, lower alkoxycarbonyl, optionally substituted aryl or optionally substituted aralkyl, n represents an integer from 3 to 6; R.sup.3 represents hydrogen or single or multiple substitution on one or more of the aliphatic carbons by one or more substituents selected from lower alkyl, optionally substituted aryl and optionally substituted aralkyl; A represents a group of formula (i) or (ii) below:--CR.sup.4 R.sup.5 --(CR.sup.6 R.sup.7).sub.m -- (i)--CX--(CR.sup.6 R.sup.7).sub.m -- (ii)in which R.sup.4, R.sup.6 and R.sup.7 each independently represent hydrogen or lower alkyl (providing that when R.sup.5 is NH.sub.2, R.sup.0 is hydrogen); m is 0 or 1; R.sup.5 represents hydrogen, NH.sub.2, OH or loweralkoxy, and X is .dbd.O, .dbd.NH or .dbd.

Abstract: The invention concerns compounds of formula I ##STR1## or a salt thereof, wherein R.sup.1 and R.sup.2 each independently represent hydrogen, lower alkyl, lower alkoxy, carboxyloweralkyl, carboxy, hydroxyloweralkyl, halogen, haloloweralkyl, lower alkoxycarbonyl, optionally substituted aryl or optionally substituted aralkyl, n represents an integer from 3 to 6; R.sup.3 which is optionally present represents single or multiple substitution on one or more of the aliphatic carbons by one or more substituents selected from lower alkyl, optionally substituted aryl and optionally substituted aralkyl; A represents a group of formula (i) or (ii) below:--CR.sup.4 R.sup.5 --(CR.sup.6 R.sup.7).sub.m -- (i)--CX--(CR.sup.6 R.sup.7).sub.m -- (ii)in which R.sup.4, R.sup.6 and R.sup.7 each independently represent hydrogen or lower alkyl (providing that when R.sup.5 is NH.sub.2, R.sup.4 is hydrogen); m is 0 or 1; R.sup.5 represents hydrogen, NH.sub.2, OH or loweralkoxy, and X is .dbd.O, .dbd.NH or .dbd.

Abstract: The invention concerns a process for preparng a thiazolo[3,2-a]benzimidazole of formula I ##STR1## in which formula n is 1 or 2, and R.sub.1 is hydrogen, lower alkyl, lower alkoxy, trifluoromethyl or halo, or a salt thereof which comprises dehydrating a compound of formula II, ##STR2## or a salt thereof wherein n and R, are a defined above, and COOR is an acid or ester function in the presence of an acid selected from sulphuric, sulphonic and phosphoric acid or mixtures thereof and if desired or required an inert solvent provided that if water is present then the amount of water is less than about 15% by volume of the acid, the reaction being carried out with heating if necessary.

Abstract: The invention concerns a process for preparing a thiazolo[3,2-a]benzimidazole of formula I ##STR1## in which formula n is 1 or 2, and R.sub.1 is hydrogen, lower alkyl, lower alkoxy, trifluoromethyl or halo, or a salt thereof which comprises dehydrating a compound of formula II, ##STR2## or a salt thereof wherein n and R, are as defined above, and COOR is an acid or ester function in the presence of an acid selected from sulphuric, sulphonic and phosphoric acid or mixtures thereof and if desired or required an inert solvent provided that if water is present then the amount of water is less than about 15% by volume of the acid, the reaction being carried out with heating if necessary.

Abstract: Nitriles of fused ring pyridine compounds such as 5,6,7,8-tetrahydroquinolines are prepared from metal derivatives of the starting compounds such as 8-litho-5,6,7,8-tetrahydroquinolines which have been prepared by treating a 5,6,7,8-tetrahydroquinoline with a metal amide prepared in situ from a metal alkyl and an N-benzylidine-N-alkylamine.

Abstract: The invention concerns thienoquinolizines of general formula (I) ##STR1## and their pharmaceutically acceptable acid addition salts. In the formula R.sup.1 is hydrogen or lower alkyl and R.sup.2 is lower alkyl, halo(lower)alkyl, --A--NR.sup.3 R.sup.4 [where A represents a direct bond between the S and N atoms or a lower alkylene group having 1 to 3 carbon atoms in the chain between the S and N atoms and R.sup.3 and R.sup.4 each independently represent hydrogen, lower alkyl, aryl or aryl(lower)alkyl or together with the nitrogen atom to which they are attached represent a five or six membered heterocyclic ring], aryl or a heterocyclic radical or R.sup.1 is --A.sup.1 NR.sup.5.SO.sub.2 R.sup.6 [where A.sup.1 is a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms, R.sup.5 is hydrogen or lower alkyl and R.sup.6 is lower alkyl, halo(lower)alkyl or aryl] and R.sup.2 is lower alkyl, halo(lower)alkyl or aryl. The compounds possess .alpha..sub.

Abstract: Nitriles and thioamides of fused ring pyridine compounds such as 5,6,7,8-tetrahydroquinolines are prepared from metal derivatives of the starting compounds such as 8-lithio-5,6,7,8-tetrahydroquinolines which have been prepared by treating a 5,6,7,8-tetrahydroquinoline with a metal amide prepared in situ from a metal alkyl and an N-benzylidine-N-alkylamine.

Abstract: The invention concerns thienoquinolizines of general formula (I) ##STR1## and their pharmaceutically acceptable acid addition salts. In the formula R.sup.1 is hydrogen or lower alkyl and R.sup.2 is lower alkyl, halo(lower)alkyl, --A--NR.sup.3 R.sup.4 [where A represents a direct bond between the S and N atoms or a lower alkylene group having 1 to 3 carbon atoms in the chain between the S and N atoms and R.sup.3 and R.sup.4 each independently represent hydrogen, lower alkyl, aryl or aryl(lower)alkyl or together with the nitrogen atom to which they are attached represent a five or six membered heterocyclic ring], aryl or a heterocyclic radical or R.sup.1 is --A.sup.1 NR.sup.5.SO.sub.2 R.sup.6 [where A.sup.1 is a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms, R.sup.5 is hydrogen or lower alkyl and R.sup.6 is lower alkyl, halo(lower)alkyl or aryl] and R.sup.2 is lower alkyl, halo(lower)alkyl or aryl. The compounds possess .alpha..sub.

Abstract: Novel benzoxazocines of formula (I) ##STR1## and their pharmaceutically acceptable acid addition salts, wherein R.sup.1 represents hydrogen, or one or more halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro, amino acylamino, mono- or di- (lower)alkyl-amino or cyano substituents, R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each represent hydrogen or lower alkyl or R.sup.3 and R.sup.4 together represent --(CH.sub.2).sub.3 --or --(CH.sub.2).sub.4 --, R.sup.5 represents hydrogen, lower alkyl, phenyl(lower)alkyl or cycloalkyl(lower)alkyl, and Ar is a phenyl radical optionally substituted by one or more halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro or amino groups exhibit activity on the central nervous system, particularly as antidepressants. The compounds can be prepared from novel alcohols of formula (II) ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and Ar are as defined above and X is fluorine, chlorine or bromine.

Abstract: The invention provides novel silyl reagents of Formula IR.sup.b R.sup.c R.sup.d SiNCYwherein R.sup.b is a branched chain alkyl of 3-10 carbon atoms, cycloalkyl of 4-8 carbon atoms or branched chain aralkyl of 8-12 carbon atoms and R.sup.c and R.sup.d are selected from alkyl of 1-10 carbon atoms, cycloalkyl of 4-8 carbon atoms, aralkyl of 7-12 carbon atoms or aryl with the proviso that R.sup.c and R.sup.d are not the same group as R.sup.b, and Y is oxygen or sulphur. A further novel compound tri-isopropylsilyl isothiocyanate is also included. These silyl reagents are useful in preparing tetrahydroquinoline 8-nitriles, amides and thioamides as described in Ser. No. 506,279.

Abstract: The invention provides new silyl derivatives of 5,6,7,8-tetrahydroquinolines and related compounds. The tetrahydroquinolines are substiuted at the 8-position by the group SiR.sub.3 where R may be one of various hydrocarbon groups or an electron donating substituent. The 8-position may also carry a lithium, sodium or potassium atom. The new silyl derivatives may be prepared by treating a corresponding 8-lithio, sodio or potassio tetrahydroquinoline with a silyl halide R.sub.3 SiHal followed by a metal compound R*M where M is sodium, potassium or lithium and R* is alkyl, cycloalkyl, aralkyl or aryl or an amine residue. The new silyl derivatives are useful intermediates for the preparation of known 5,6,7,8-tetrahydroquinline-8-nitriles, amides and thioamides employing an alkyl silyl isothiocyanate or cyanate. The nitriles and thioamides are anti-ulcer agents. The related compounds may be made by analogous methods.

Abstract: An improved process for preparing tetrahydroquinolines and related compounds especially 5,6,7,8-tetrahydroquinoline-8-nitriles, amides and thioamides is described. The nitriles and thioamides are anti-ulcer and/or anti-secretory agents. Typically a compound of formula A ##STR1## where M is sodium, potassium, lithium or MgHal where Hal is chlorine, bromine or iodine, is reacted, e.g., in an ether solvent, with a silyl compound R.sub.x.sup.a Si(NCY).sub.4-x (III) wherein R.sup.a is alkyl, cycloalkyl, aralkyl, or aryl, at least one group R.sup.a being a branched chain alkyl, cycloalkyl, aryl or branched chain aralkyl, Y is oxygen or sulphur, x has a value from 1 to 3, then subjecting the product to hydrolysis or alcoholysis, to obtain the corresponding nitrile, amide or thioamide, provided that when a nitrile is desired the molar ratio of compound III to compound A is at least 2:1 and x is 3 and Y is S. The products may be obtained as acid addition salts.Compound A may contain various substituents, e.g.

Abstract: m-Hydroxyphenyl substituted compounds of formula ##STR1## where R is an organic radical and R.sup.1 is hydroen or an organic radical are prepared by dehydrohalogenating a compound of formula ##STR2## (where X is chlorine or bromine, and R and R.sup.1 have the above meanings). Preferred novel starting materials of formula (II) are of the formula ##STR3## (where R.sup.1 and X are as above, n is 2,3 or 4, R.sup.2 is hydrogen or lower alkyl and R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl(lower)alkyl or aryl(lower)alkyl).

Abstract: Dihydropyridines of formula ##STR1## where R.sup.6 is lower alkyl and R.sup.5 is lower alkyl or aryl (lower)alkyl are prepared by a novel process from sodium or potassium salts of 1-substituted-1,6-dihydro-5-hydroxy-3[2H]-pyridones. The dihydropyridines are useful as intermediates for pharmacologically active 1-optionally substituted-3-phenyl or substituted phenylpiperidin-5-ols and esters. Some of the piperidinols and esters are novel; those where the 1-substituent is aryl(lower)alkyl are intermediates, those where the 1-substituent is cycloalkyl(lower)alkyl are analgesics or antidepressants and those in which the 1-position is unsubstituted are anti-secretory agents.

Abstract: 3-Aryl-3-aryloxyalkylamines of the general formula (I) ##STR1## and their pharmaceutically acceptable acid addition salts, wherein R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen or lower alkyl, R.sup.3 is hydrogen, lower alkyl or benzyl, Ar is phenyl optionally substituted by one or more halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro or amino groups, and Ar.sup.1 is methylsulphinyl, methylsulphonyl- or cyano-substituted phenyl, 2- or 4-pyridyl, 2-pyrazinyl, 2-quinolinyl, 2-thienyl or 2-thiazolyl exhibit activity on the central nervous system, e.g. as antidepressants.

Abstract: 4-Aryl-4-aryloxypiperidines of the general formula (I) ##STR1## and their pharmaceutically acceptable acid addition salts, wherein R.sup.1 and R.sup.2 are hydrogen or lower alkyl, R.sup.3 is hydrogen, lower alkyl or benzyl, Ar is phenyl optionally substituted by one or more halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro or amino groups and Ar.sup.1 is a phenyl radical optionally substituted by one or more cyano, methylsulphinyl, methylsulphonyl, lower alkoxy, trifluoromethyl, lower alkyl, lower alkenyl, halogen, nitro, amino or acylamino groups or an aromatic heterocyclic mono- or di-cyclic radical, exhibit activity on the central nervous system, e.g. as antidepressants.

Abstract: Novel benzoxazocines of formula (I) ##STR1## and their pharmaceutically acceptable acid addition salts, wherein R.sup.1 represents hydrogen, or one or more halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro, amino acylamino, mono- or di- (lower)alkyl-amino or cyano substituents, R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each represent hydrogen or lower alkyl or R.sup.3 and R.sup.4 together represent --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --, R.sup.5 represents hydrogen, lower alkyl, phenyl (lower)alkyl or cycloalkyl (lower)alkyl, and Ar is a phenyl radical optionally substituted by one or more halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro or amino groups exhibit activity on the central nervous system, particularly as antidepressants. The compounds can be prepared from novel alcohols of formula (II) ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and Ar are as defined above and X is fluorine, chlorine or bromine.

Abstract: 2-Oxo-hexahydroazepine, -piperidine or pyrrolidines of formula ##STR1## wherein n is 2,3 or 4, R is hydrogen, lower alkyl, aryl(lower)alkyl, loweralkenylmethyl or cycloalkylmethyl, R.sup.1 is hydrogen or lower alkyl and R.sup.2 is hydrogen, lower alkyl or aryl(lower)alkyl are prepared by a novel process involving reaction of an anion of a lactam of formula ##STR2## where R.sup.3 is lower alkyl, aryl(lower)alkyl, trialkyl-, triaryl- or triarylalkyl-silyl with a benzyne of formula ##STR3## where R.sup.4 is lower alkyl, aryl(lower)alkyl or trialkyl-, triaryl- or triarylalkyl-silyl. The products are useful as intermediates for preparing pharmacologically active 2-unsubstituted -hexahydroazepine, -piperidine and pyrrolidine derivatives.

Abstract: The invention concerns novel 2-oxo-hexahydroazepine, -piperidine and -pyrrolidine of formula I ##STR1## where n is 2,3 or 4, R is hydrogen, lower alkyl or aryl(lower)alkyl and R.sup.1 is lower alkyl. The compounds may be aromatized and the aromatized compounds converted to 3,3-disubstituted-hexahydroazepine, -piperidine and -pyrrolidine compounds having pharmacological activity, particularly analgesic activity.