The Upjohn Co.

Pharmacia & Upjohn Company

Other

Chiu-Hong Lin

Arthur Glenn Romero

Susanne R Haadsma-Svensson

Michael D Ennis

Per A Carlsson

Bengt R Andersson

John C Sih

Gordon L Bundy

Roy A Johnson

Hakan V Wikstrom

Nils P Stjernlof

William H Darlington

Stig Thomas Elebring

Kerry Anne Cleek

Kjell A Svensson

Bradley D Hewitt

Thomas Andrew Runge

Kjell Anders Svensson

Kjell Anders Ivan Svensson

Steven Paul Tanis

Ruth Elizabeth TenBrink

Gilbert A Youngdale

Robert B McCall

R Nicholas Waters

Clas A Sonesson

Lars O Hansson

Jeffrey A Leiby

Montford F Piercey

Robert A Lahti

N Peter Stjernlof

The present invention relates to (2S)-enantiomers of 2-aminoindan derivatives of formula I:and a novel process for the preparation of them.

Process to prepare 2-aminoindan derivatives

Novel aromatic bicyclic amines of formula (I) ##STR1## are useful in treating central nervous system disorders and cardiac arrhythmias and cardiac fibrillation.

Heterocyclic compounds for the treatment of CNS and cardiovascular

Compounds and their pharmaceutically acceptable salts suitable for treating central nervous system disorders associated with the dopamine D3 receptor activity of structural Formula I: ##STR1##

Aryl substituted bicyclic amines as selective dopamine D3 ligands

2-aminoindans as selective dopamine D3 ligands

A compound of Formula I ##STR1## or pharmaceutically acceptable salts of Formula I, where R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, --(CH.sub.2).sub.n CONH.sub.2 where n is 2 to 6, (CH2).sub.n -1-(4,4-dimethylpiperidine-2,6-dione-yl), or cyclopropylmethyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl or combined with R.sup.1 to form a C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 akynyl, (CH.sub.2).sub.n --X--Ar where X is O, S, or NH, 3,3,3-trifluoropropyl, --(CH.sub.2).sub.m --R.sup.9 where m is 2 or 3 and R.sup.9 is phenyl, 2-thiophenyl or 3-thiophenyl; R.sup.3 is hydrogen, C.sub.1 -C.sub.3 alkyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, formyl, CN, halogen, CH.sub.2 OR.sup.2, C(O)C(O)OR.sup.1, C(O)CO NR.sup.1 R.sup.2, --(CH.sub.2).sub.q --NR.sup.1 R.sup.2 where q is 0 to 5, C.dbd.NOR.sup.2, 2(4,5-dihydro)oxazolyl, or COR.sup.10 where R.sup.10 is H, R.sup.1, NR.sup.1 R.sup.2 or CF.sub.3 ; R.sup.4 is hydrogen, C.sub.1 -C.sub.3 alkyl, cyclopropylmethyl, CF.sub.3, 2,2,2-trifluoroethyl, CN, CONR.sup.1 R.sup.2, .dbd.O, 2(4,5-dihydro)imidazolyl, 2(4,5-dihydro)oxazolyl, 2-oxazolyl, 3-oxadiazolyl, or 3,3,3-trifluoropropyl; R.sup.5 is hydrogen, R.sup.1, OCH.sub.3, C(O)CH.sub.3 or C(O)OR.sup.1 ; X is (a) a valence bond, (b) CH.sub.2, or (c) O, S or NR.sup.5 where R.sup.5 is H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, benzyl, COR.sup.6 where R.sup.6 is a C.sub.1 -C.sub.3 alkyl, phenyl, or CONR.sup.7 R.sup.8 where R.sup.7 and R.sup.8 are independently H or C.sub.1 -C.sub.3 alkyl; and Z is a hydrogen or halogen; provided that when X is CH.sub.2, at least one of R.sub.3 and R.sub.4 is other than hydrogen or C.sub.1 -C.sub.3 alkyl. The compounds of Formula I are suitable for treating disorders of the central nervous system, particularly as 5-HT.sub.1A receptor agonists.

Centrally acting 6,7,8,9-tetrahydro-3H-benz(e) indole heterocyclics

This invention is therapeutically useful 2-aminotetralins and pharmaceutically acceptable acid addition salts thereof of the formula ##STR1## R, R.sub.1 to R.sub.5 and p are as defined in the specification, these compounds are useful to treat central nervous system disorders, hypertension, diabetes, sexual impotency and to control appetite.

Therapeutically useful 2-aminotetralin derivatives

This invention is therapeutically useful tetralins and pharmaceutically acceptable acid addition salts thereof of the formula ##STR1## wherein R, R.sub.1 and A are as defined in claim 1. These compounds are useful to treat central nervous system disorders.

(1,2N) and (3,2N)-carbocyclic-2-amino tetralin derivatives

This invention is therapeutically useful tetralins and pharmaceutically acceptable acid addition salts thereof of the formula I: ##STR1## wherein X is --(CH.sub.2).sub.n -- or --C(R.sub.1)(H)--; R is C.sub.1 -C.sub.8 alkyl; and R.sub.1 and R.sub.2 are the same or different and are selected from the group consisting of hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8) alkynyl, aryl and benzyl. These compounds are useful to treat central nervous system disorders and are unexpectedly resistant to metabolism by the liver and have superior oral plasma bioavailability.

Carboxamido-(1,2N)-carbocyclic-2-aminotetralin derivatives

A compound of Formula I ##STR1## or pharmaceutically acceptable salts of Formula I, where R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, --(CH.sub.2).sub.n CONH.sub.2 where n is 2 to 6, (CH2).sub.n -1-(4,4-dimethylpiperidine-2,6-dione-yl), or cyclopropylmethyl;

Centrally acting 6,7,8,9-tetrahydro-3H-benz(E)indole heterocyclics

Centrally acting 6,7,8,9-tetrahydro-3H-benz(e)indole heterocyclics

.alpha.-amino-indole-3-acetic acids useful as anti-diabetic,

Novel 1,4-naphthalenediol and 1,4-hydroquinone derivatives of formula I, II, III and IV and their therapeutic uses as 5-lipoxygenase inhibitors, leukotriene inhibitors, antiinflammatory and/or inhibitors of mucus secretion agents are described. Also provided are novel intermediates useful for the preparation of said derivatives. ##STR1##

1,4-naphthalenediol and 1,4-hydroquinone derivatives

The present invention provides novel 3'-pyridinylalkenylindole-2-carboxylic acids and derivatives thereof of the formulas I and II ##STR1## which are useful as thromboxane A.sub.2 (TXA.sub.2) synthetase inhibitors and as such represent potent pharmacological agents.

3'-pyridinylalkylinden- and 3'-pyridinylalkylindol-2-carboxylic acids

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Portage, MI, United States of America

Chiu-Hong Lin