EP-4735419-A1 - DEUTERATED ORGANIC COMPOUNDS AND USES THEREOF

Abstract

Provided are compounds of Formula I and Formula II, described herein, processes for their preparation, their use as pharmaceuticals, and pharmaceutical compositions comprising them and intermediates used in their preparation. Compounds of Formula I and Formula II are useful, for instance, in modulating dopamine and serotonin neurotransmission and treating disorders that may benefit from the same, such as schizophrenia and depression.

Inventors

• VADODARIA, Krishna
• VANOVER, KIMBERLY
• SUDARSAN, Vikram
• GARVEY, DAVID

Assignees

• Engrail Therapeutics, Inc.

Dates

Publication Date

20260506

Application Date

20240702

Claims (1)

1. orneoceo.-- c caommeo:un oormua: R 2 R 3 weren a 1 ,eas 2 , on 3 ,e o 4 , an 1 , 2 , 5 ar 3 e,n 4 ,e anenens seecerom an annree or saor 5 comoun omo.rmu Ra 8 : were a 6 ,eas 7 ,n a: on 8 areneenen seecerom an annree orn sea oor 6 m,, 7 , an 8 s orneoceo.--. weer ceonmoeu cnom acocournns suo csaanma orre,e os, enanomer. . e werene comounsnreeorm. . comoun accorno cam or, weren eac o 1 , 2 , 3 , 4 , an 5 are.. ee c coommoouunn a accccoorrnnoo c caamm, or, o,r w,e wreenre eanc o 6 , 7 , an 8 are. De comou Dns: D nr ,. ee D ,,, s: D nree ,. aerm coam or ceuoucna ac accocrenaoe a sna oonrem o, casamresae-r, wanerene comoun,nree or a one or moreosonsesnae aseuerum. ncororaon oeuerum orneoceo.--. comaormaceuca comoson, werenearmaceuca comoson comrses a orm, aunn a accoarrmanceuo acna on aecc oe cams-,nree orarmaceuca acceae sa . meoorreamen o aranasoree crarnrer. meo comrses amn aaenn neeereo, werene cams-,nree orarsmearcneucoae acaceena a ceo smaouonrm, a ocrcorno an one o como anxees aarmaceuca . e moon sor a accccoorrnnoo c caamm., werenesorers an aecvesorer or an . seor meo acecro.rno cam, werenesorerseresson, an anxe soreerr,scos, as,e scnozno-erenca, scerzaoaecvesorer,os-raumac sress anorexa nervosa,uma nervosa,ne-ceavnssoorreerr,o,smoourrece snrome, osessve comusvesorer, acon, sorer, . e meo accorno ca oarsorer, or a mrane. anxesorer, aoa, ormene,ra wzeere annxee anxseorers.orersancsorer, soca . asseoc maeeo w acco anrenonoa c,a sumca, weeareonesorers aneona,eresson eresson,reamen-ressaneresson,n, asnxomusa,eroesasrone,rnesasmmaor eresson, oros-scoceresson on,scoc .. ee m meeoo a accccoorrnnoo c caamm,, w weer. reennesorers anxouseresson. . e meo accor esorers meancoceresson. . e meo accornnoo c caamm,, w weerreenneessoorreerrss m aaoreressvesorer. . e meo accorno cam, susance usesorer. . werenesorersos-raumac sresssorer orneoceo.--. se comoun accorno an one o cams-,nree orarmaceuca acceae oa aorramn, ors aorearrmaceuca comoson accorno cam,or usenereamen. msee oca am ceonmoorun. rea amcceonr ono an one o cams-ne manuacure o a. e use accorno cam a orran, wsorer. cams-. ereneransorers as recen an o

Description

orneoceo.-- eu, ,s a..croavosno cnaamsrcoarono..rovsona caono. , rovsona caono. , euo., ,,..eu, ,.. , eu, ,..rovsona ca rovsona caono. ..rovsona caono. , eu,ono., , eu, , caono. , eu, ,e conens an..rovsonancororae reerencener enrees. o eac o wc areere orerreararoovn,ee arre us ceo amsouanrmsa oceuocrmasu,a an anormua,escreeow,rocesses em annermeaes usenerrearaon.omouanrmsa oceuocra comosons comrsn useu,ornsance,n mouanoamne an seroonn neuroranmsmuas anormua are sorersa maenerome same, suc as sczorena aneressosnon a.nrean vounar movemoenam,eneesnn,v aoven a vare o cenra nervous ssemuncons,ncun eroonn asosnvoven a varece, rewar, see, aenon, worn memor, anearnn. conon, rewar,earnn, memor, a on cenra nervous ssemuncons,ncun moo, oamnerc anor seroonercsunc vaorno cuasneasoooscarocesses.ccorn, eresson. eases suc as sczorena an am oroene-nco reueaeseoroammnresnacermnas,oamne acvaes memers o a ven e receors-.oamne receors- are o-eo recweoorrosu acs,vaees a-ene c acnase an anncree-e,, an .cvaonnor.cvaon o-e receorsns acvaasoesn c o aeneves c.ca-se.e receors are orneoceo.-- -eoamne- recee reocres aorers e axrereossuenoossonsasncaac oano onamne-receve ces, we resnaca on oamneare ces an ouroeenam snerc neurons. o sero eroonn receor sues,roueno su-ames, meae eecs resnaoncn-.e- receor sue, a maor receor sue, exss as e auoreceorn seroonn neuronsne rae nuce an asossnac meecroarnecsemso orsn-ere rercoenaor csornex,e raoec namuceus, m saeuem, anerenoromaam-us. rneacn oerran reons.cvaon o- ossnac receors can ecnc eorsn reease.e- receor sues enrcen corex ansn reaseoamneurnover an aso mouaesoamne reease.- rece eoosanoso roeres, we- receor aonsmsouoeor anaonssave anscoc anaucnoencroeres.eaucnoe assocae w conon-enancn socn areouo arseromer-nc e receecso or aserceame an een reoreoromoe neuraasc an reuc onsm.- aonsmas aso amar o annscsoccosscs are re ucseeoor a mnaanaonesmse .ceosre ress,s cenon. oarr ancuaaorn scszorena. reucnosve smoms o sczorenaornsance,aucn ms eecven oen asorouces exrarama se eecs,ncu aons aneusons,u snesa,ncreasesroacn, an m narnsonsm, aasa, anarvensance,oss oner a exacerae neave smoms o sczorenaor eeaur es an movaonne an acves, soca wrawa, an aneona. receor ane o aca anscocss receor anaonsmn comnaon w- moo aonsm, wc ma exaner enance ecac an reuce exrarama romr serees esoenc,s wc m caomearee uonreacea an cusrrceno mces.caanonss.cowoecvera, soenms aso suer anscocs are use auncveo seroonerc aneressanso e aca maoreressve mrove resonsen an curren meeccaasuosreemr.aancesnoamne an seroonn caneao a vare osorers a can mo ons ma noe aeo eecve mouaeeves oo, new comounsreanseauseaseaoanmvonvee anm saeraoncoensnn neouroamrannsem anss soenro aroen nnee.e, as are meos o orneoceo.-- roves a comoun oormua: R2 R3 R4 we a1,re ea2,n:3,4, an5 areneenen seecerom an an nrese o orn sea oor1,2,3,4, an5s ormua,rumr.errove arearmaceuca comosons comrsn comouns o comouns ooceosrsmesuoar,roeranrsnan ccoem, aso aunn asn o-anoremoua, anarmaceuca uses o eresson, anos-raumac nc aen anorea sczorena, roves a com sresssorer. R8oun oormua: weren: orneoceo.-- a6,ea7, an8 areneenen seecerom an an nrs one o6,7, an8s wereeen or sea coomrm uro,unersro svusean areaarrmee os, enanomer. ormua,rocessesorrearn comoaucneus oca coomosons comrsn comouns o comouns oormua,ornsance, as an an-anremounac a, anarmaceuca uses o eresson, ano en anorea sczorena, urs-erra auremaas oc sresssorer. eeaeescronrove aerceanaer. o seouresene unnvenon wecome aarenrom an secc exames, wencanreerre emomenesrs oooenaveneone,a aeescron uroses ousraon on an are noneneome scoe oenvenorne.neneor nemonare anuree com soowusn av oeraxeamasema conc weneran aonmnnmn ras o cs, m. sere a a sne ose o. nemona ure sows averaeran concenraonnmn ras o cs, m.re ane comoun oxame wen amnsere a a sne ose o. n memon.are anuree com soowusn av oeraxeamasema conc weneran aonmnnsmeren a ra as s on ces,ose o. nemonare anuree com soowusn av oeraeran concenraonnmn ras o cs, m. xame wen amnsere a a sne ose o. comoun oxamuree sows w aveenra aemnassmear anran concenraonsnmn ras oe ure sows averaeasme a a sne ose o. m. comoun oxame wen amnseare an a ara snn coencenroaseon osn. mmn. ras oe orneoceo.-- romnernaonaurue scaowons eoe.cs o amnsrao onn ooxaammneene n auncexame ree-movnr us accumens o uarueawe rasasene. romnerna e sows eecs o amnsraon oxame anxame ree-movnonarauuecaawone roa.sasene. onoamnenererona corex o naure ansn noe woaownenneescron oereerre emomenss mere exemarn ne even o a coonmcnenvenon,s acaon, or uses. ce reerence,e aenonneresenscosure ana o a - anresen- rescceosourrse a croen erxorse. ceosam anne nreesurnoans.caoam onneo reacmenoers ne ounronos.sse amoneaom neneo rsecsenaorsc aare m oannooamcanee oanr neon- uoreceors conrue urons are cae auoreceors. reease, an ua o reuanoamne neuron acv an conrone sness, ose o a-eree rs o ecneao orcamn a-e.eoamne auoreceors reuaeoamne reease.owncr naons mareerenaocresnac auoreceors an oaemaseneo neaumronrean rsemeassse,o wn.eea aveose m ocaoc