Eli Lilly and Company

Lilly Industries, Inc.

University of East Anglia

Other

Jeremy Gilmore

Jason Scott Sawyer

Nicholas J Bach

Peter Thaddeus Gallagher

Stephen Richard Baker

Alexander McKillop

Russell Andrew Lewthwaite

George Richard Stephenson

Graham Henry Timms

John Joseph Masters

Barry P Clark

Maria Ann Whatton

Magnus Wilhelm Walter

Manuel Javier Cases-Thomas

Christopher David Beadle

Virginia Ann Wood

Michael William Urquhart

Colin W Smith

William M Owton

Andrew Caerwyn Williams

Alec Todd

Nicholas Paul Camp

John Richard Harris

Ana Belen Bueno Melendo

Carlos Lamas-Peteira

Martin Victor Miles

Michael William John Urquhart

Javier Agejas-Chicharro

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, which are useful for the inhibition of the uptake of one or more physiologically active monoamines (serotonin, norepinephrine, and dopamine).

3-Aminopyrrolidines as inhibitors of monoamine uptake

3-aminopiperidines and 3-aminoquinuclidines as inhibitors of monoamine uptake

This invention relates to compounds of formula (I) where Rto R, &#x2014;W&#x2014;V&#x2014;, &#x2014;X&#x2014;Y&#x2014;, p and n have the values defined in claim, their preparation and use as pharmaceuticals for the treatment of central nervous system disorders, such as depression, bipolar disorder, and anxiety.

Isochroman compounds for treatment of CNS disorders

This invention relates to a method of making N-benzyl indoles, and to intermediates for use in the method, and to certain substantially optically pure N-benzyl indoles obtained by the method.

Process for preparing N-benzyl indoles

Process for preparing n-benzyl indoles

A process for producing a compound of the formu5la ##STR1## comprising the step of reacting a compound of the formula ##STR2## with a compound of the formula ##STR3## to form a compound of the formula ##STR4## wherein R.sup.2a is selected from the groups recited above for R.sup.2, or R.sup.2a --X-- is a protected hydroxyl group, and Z is a group of formula --Y--R.sub.5 recited above, or a group that can be converted into a group of said formula --Y--R.sup.5. Intermediates of formula IV and composition containing substantially optically pure enantiomers of Formula (I) are included within the scope of the invention.

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

Serotonerbic tetrahydropyridoindoles

A compound having pharmaceutical activity, of the formula ##STR1## in which A is hydrogen or --(CR.sup.1 R.sup.2).sub.x R.sup.3 where x is 0 or 1 to 4, R.sup.1 and R.sup.2 are each hydrogen or C.sub.1-4 alkyl and R.sup.3 is --CN, --COOH, tetrazolyl or --CONHSO.sub.2 R.sup.4 where R.sup.4 is optionally substituted phenyl, and ##STR2## where R.sup.5 and R.sup.6 are each hydrogen, C.sub.1-4 alkyl or --(CR.sup.1 R.sup.2).sub.x R.sup.3 where x, R.sup.1, R.sup.2 and R.sup.3 are as defined above, and R.sup.7 is hydrogen, C.sub.1-4 alkyl or --(CR.sup.1 R.sup.2).sub.x R.sup.3 where x is 1 to 4, and R.sup.1, R.sup.2 and R.sup.3 are as defined above;

Pharmaceutical compounds

A compound of the formula ##STR1## in which R.sup.1 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C.sub.1-4 alkyl, aldehydo, --CH.sub.2 Z, --CH.dbd.CH--Z or --CH.sub.2 CH.sub.2 Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R.sup.2 is halo, nitrile, an optionally protected acid group or --CONR.sup.7 R.sup.8 where R.sup.7 and R.sup.8 are each hydrogen or C.sub.1-4 alkyl; R.sup.3 and R.sup.4 are each hydrogen, C.sub.1-4 alkyl, optionally substituted phenyl, or C.sub.1-4 alkyl substituted by --CONR.sup.7 R.sup.8 or an optionally protected acid group; R.sup.5 is ##STR2## where W is --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --O-- or --S--, R.sup.9 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or trihalomethyl, and R.sup.10 is hydrogen, C.sub.1-4 alkyl, C.sub.2-6 alkenyl, C.sub.3-6 cycloalkyl or C.sub.1-4 alkyl-C.sub.3-6 cycloalkyl; R.sup.6 is hydrogen or C.sub.1-4 alkyl; X is --O--(CH.sub.2).sub.n CR.sup.11 R.sup.12, --CR.sup.11 R.sup.12 --, --CR.sup.11 R.sup.12.(CH.sub.2).sub.n.CR.sup.13 R.sup.14 -- or --CR.sup.11 .dbd.CR.sup.12 -- where R.sup.11, R.sup.12, R.sup.13 and R.sup.14 are each hydrogen or C.sub.1-4 alkyl, and n is 0, 1 or 2; and Y is --O--CR.sup.15 R.sup.16 --, --CR.sup.15 .dbd.CR.sup.16 -- or --CR.sup.15 R.sup.16.CR.sup.17 R.sup.18 -- where R.sup.15, R.sup.16, R.sup.17 and R.sup.18 are each hydrogen or C.sub. 1-4 alkyl; or a salt thereof. The compounds in unprotected form are active as leukotriene antagonists.

Certain indole derivatives useful as leukotriene antagonists

A pharmaceutical compound of the formula ##STR1## in which A is selected from --NHCOR.sup.1, --NHCOOR.sup.1, --NHCONHR.sup.1, --NHCSNHR.sup.1, --CONHR.sup.1, where R.sup.1 is optionally halo-substituted C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.3-7 cycloalkyl-C.sub.1-4 alkyl or phenyl-C.sub.1-4 alkyl B is optionally substituted phenyl, and --X--Y-- is --CH=CH-- or --CH.sub.2 --CH.sub.2 --; and salts thereof. The compounds are leukotriene antagonists.

Growing community of inventors

Frimley, United Kingdom

Jeremy Gilmore