John Wyeth Brother, Limited

American Home Products Corporation

Robin G Shepherd

Alan C White

Christopher Ian Brightwell

Roger Crossley

Adrian Charles Curran

Barry John Langham

Sie-Yearl Chai

John Frederick Cavalla

Arnold S Milowsky

Maynard E Lichty

Albert Opalko

Brian John Bushell

Oxathiazolidinyl pyridines

Processes and intermediates for the preparation of piperazine derivatives

Preparation of .alpha.-aryl .gamma.-butyrolactones

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:

Certain cyclopenta[b]pyridines and 5,6,7,8-tetrahydroquinolines having

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:

Method for the production of 2-bromo-5,6,7,8-tetrahydroquinoline and the

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.

Process for preparing thiazolobenzimidazoles and intermediates used

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.

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.

Preparation of nitriles of fused ring pyridine derivatives

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.2 -adrenoceptor antagonistic activity in warm blooded animals.

7H thieno[2,3-a]quinolizines, useful as .alpha..sub.2 -andrenoceptor

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.

Preparation of nitriles and thioamides of fused ring pyridine derivatives

Thienoquinolizines and their use as .alpha..sub.2 -adrenoceptor

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.

Benzoxazocines intermediates

The invention provides novel silyl reagents of Formula I

Novel silyl reagents

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.

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Maidenhead, United Kingdom

Robin G Shepherd