Eli Lilly and Company

Lilly Industries, Inc.

Colin W Smith

Peter Thaddeus Gallagher

William M Owton

Colin P Dell

Michael Brunavs

Jai P Singh

Martin Victor Miles

William Dawson

Michael John Foulis

Norman James Gutteridge

William F Heath, Jr

Lawrence E Stramm

John Fairhurst

Samantha J Ambler

Terence Alan Hicks

Jeremy Gilmore

David R Dobson

Pharmaceutical compounds of the formula: ##STR1## in which n is 1 to 6, m is 1 or 2 and p is 1 or 2, R.sup.1 and R.sup.2 are each hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, HO--C.sub.1-4 alkyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, C.sub.1-4 alkylthio, halo, optionally substituted phenyl, optionally substituted phenyl-C.sub.1-4 alkyl, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a C.sub.3-6 cycloalkyl group, &gt;C.dbd.O, C.dbd.NOR' where R' is hydrogen or C.sub.1-4 alkyl, R.sup.3, R.sup.4 and R.sup.5 are each hydrogen, halo, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkyl-CO--, where m is 0, 1 or 2, R'R'N--SO.sub.2 --, --COOR', --CONR'R', --NR'R', --N(OR')COOR', --COR', --NHSO.sub.2 R', where R' and R' are each hydrogen or C.sub.1-4 alkyl, R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl, X is oxygen or sulphur, the dotted line represents an optional double bond, and the fluorine atom is attached at the 6- or 7-position; and salts thereof.

Indole compounds

A pharmaceutical compound of the formula ##STR1## in which X is --CR'R'-- or --C(O)-- where R' and R' are each hydrogen, C.sub.1-6 alkyl or optionally substituted phenyl, Y is oxygen or sulphur, R.sup.1, R.sup.2 and R.sup.7 are each selected from halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, trifluoromethyl, nitro, cyano, amino, phenyl, phenoxy, benzyl, benzyloxy, acylamino, C.sub.1-4 alkylsulphonylamino, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphonyl, carboxamido, sulphonamido, hydroxy, methylenedioxy, carboxy, and heteroaryl, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each hydrogen, C.sub.1-6 alkyl or optionally substituted phenyl, n, m and p are each 0, 1, 2 or 3; or a salt or ester thereof.

5HT receptor binding benzimidazolylpiperidines

A pharmaceutical compound of the formula ##STR1## and salts and esters thereof.

Pharmaceutical compounds

Pharmaceutical compounds of the formula ##STR1## in which n is 0, 1 or 2 and R.sup.1 is attached at any of the positions 7, 8, 9 or 10, and each R.sup.1 is halo, carboxy, trifluoromethyl, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, hydroxy-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkoxy, nitrogen-containing heterocyclyl, nitro, trifluoromethoxy, --COOR.sup.5 where R.sup.5 is an ester group, --COR.sup.6, --CONR.sup.6 R.sup.7 or --NR.sup.6 R.sup.7 where R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl;

This invention provides novel compounds and pharmaceutical methods comprising the administration of a compound of the Formula I: ##STR1## wherein n, m, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are variables.

Pharmaceutical compounds of the formula ##STR1## in which n is 0, 1 or 2 and R.sup.1 is attached at any of the positions 7, 8, 9 or 10, and each R.sup.1 is halo, carboxy, trifluoromethyl, hydroxy, C.sub.1 -4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, hydroxy-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkoxy, nitrogen-containing heterocyclyl, nitro, trifluoromethoxy, --COOR.sup.5 where R.sup.5 is an alkyl group, --COR.sup.6, --CONR.sup.6 R.sup.7 or --NR.sup.6 R.sup.7 where R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl;

5,6-dihydronaphtho [1,2-b]pyrans and their use as pharmaceutical

This invention provides novel, optionally substituted tetrahydropyridoindoles which are useful serotonergic agents for the treatment of central nervous system disorders.

Serotonerbic tetrahydropyridoindoles

Pharmaceutical compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, hydroxyl, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acyloxy, --O-glucoside, optionally substituted phenyl or optionally substituted phenyl-C.sub.1-4 alkoxy;

Methods of treating an immune disease, cell proliferation, restenosis and vascular smooth muscle cells using the pharmaceutical compounds of the formula ##STR1## in which R.sup.2 is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R.sup.2 is furanyl optionally substituted with C.sub.1-4 alkyl; and salts thereof.

Methods of using dihydropyrans

This invention provides a method of treating diabetic complications in mammals which comprises the administration of a compound of the Formula I: ##STR1## in which n, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are variables.

Therapy for diabetic complications

A pharmaceutical compound of the formula ##STR1## in which n is 0, 1 or 2 and R.sup.1 is attached at any of the positions 5, 6, 7, 8, 9 or 10, and each R.sup.1 is halo, trifluoromethyl, C.sub.1-4 alkoxy, hydroxy, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkylthio, hydroxy-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkoxy, trifluoromethoxy, carboxy, --COOR.sup.5 where R.sup.5 is an ester group, --CONR.sup.6 R.sup.7 or --NR.sup.6 R.sup.7 where R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl; R.sup.2 is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R.sup.2 is furanyl optionally substituted with C.sub.1-4 alkyl; R.sup.3 is nitrile, carboxy, --COOR.sup.8 where R.sup.8 is an ester group, --CONR.sup.9 R.sup.10 where R.sup.9 and R.sup.10 are each hydrogen or C.sub.1-4 alkyl, or R.sup.11 SO.sub.2 -- where R.sup.11 is C.sub.1-4 alkyl or optionally substituted phenyl; and R.sup.4 is --NR.sup.12 R.sup.13, --NHCOR.sup.12, --N(COR.sup.12).sub.2 or --N.dbd.CHOCH.sub.2 R.sup.12 where R.sup.12 and R.sup.13 are each hydrogen or C.sub.1-4 alkyl optionally substituted with carboxy, ##STR2## where X is C.sub.2-4 alkylene, or --NHSO.sub.2 R.sup.14 where R.sup.14 is C.sub.1-4 alkyl or optionally substituted phenyl; provided that when n is 0, R.sup.3 is nitrile and R.sup.4 is --NH.sub.2, R.sup.2 is not phenyl or phenyl substituted in the para-position with a single chloro, hydroxy or methoxy substituent; and salts thereof.

This invention provides a method of treating diabetic complications in mammals which comprises the administration of a compound of the Formula I: ##STR1## in which n, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are variables.

Propanoic acid derivatives of the formula: ##STR1## where R.sup.1 is a C.sub.1-8 alkyl group optionally substituted by hydroxyl or --COOH and R.sup.2 is hydrogen or a protecting group, are useful as anti-thrombotic agents.

Growing community of inventors

Bracknell, United Kingdom

Colin W Smith