The Synthesis and Reactions of Substituted Carbamates

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SH1JOTEJWXS ARB SK3»TW?JfS % ® m&k »a carried rnt ana to Dr, 39w al&Mhmm* Hi M11&1 and Oo*, for m$£$m paeeifcl* the deiermimtton of the phm^mmlog**

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»

t 1 m® eynfheeiaed in X83& (1)* feat

Bthyl earlwsai©*

irn tll recently i t hm feeen nm& m m mmM wMLg m X&fear&iory antasals*

Tfamm of it# fsefele and vmmtMLn. notion®-* i t m» need only feriefiy m a hyjm eti© i n hmm®-*

In mm mum® o f * wmmt etwdy m the ©ffeeie of cert&in eeng®s0»da m rn^rniwm^mkl tanara* fhMm and Itodtaft {&> m&im& th&i eth y l M&Atttte was slig h tly effectiv e l*i prod&cing recession® of c e rta in e&rciaoims*

Baring fa rth e r c lin ic a l tria ls * P&itersan and

©©•workers (3) notloed that in some

ethyl

produced

& f a l l l a the X«c©cyte m u st, following which t r i a l s mv® extended t o Xesikemia# a ^ « r m » c h s r s & te r ie e d m a in ly tagjr a n I m

cyt© pmdmstim*

i t

I n l« c o * *

from the c lin ic a l r©«Xte on Xe^Mia* i t was cfe*

▼ious th at In the ®y#lei& or lymphatic form of the aieea*©* ethyl carfesm tt m® d e fin ite ly effectiv e.

In a mealier of cases there -were

©fee®3nr©&* (a) a rapid decline in the leucocyte ernrnt to mtrml lim its , (fe) a i m&m&

the d iffe re n tia l eoos&t to rev ert to a more

ttersnl couiposition* and (c) a diminution in spleen else and glandular masses,

ftmm effect®# while thegr may oeeaeionally p e rs is t for a

variable time a f te r ethyl m&mmkm withdrawal* are# hew«nrert ©sc©**-

t w o rsiM o .

W m

at© hm$ i m i M

nv& 'pm®of

Iflftteadla* ©tl^l &&bm*

y o l ft©

an d o t t o tm to m rd .

*et£on® p rw w » l * ff© % 3,« w i f t l f o f ©voroomtssg.

Kb* «j&3©ei of t&U mmimoh projoci m s to afady tlws igrtt* til©©'!©: o f 6*vlm1&m of iWMftoamt© &©!4 im ih© lidp«© of f i n a l s &&$>&&»

alt*

m m pa%m% m d

«po«stft« iiw t

4 m i« v of i3a© Utorairar#

i!mi a eosiatdmrifte mi t&stod

of mtmti %©•&©& Mritaa&t* o®tar$ hud tioon

for TOPiotft* wxmmm (2# % h, 5* &!)• f t mss mtim€ ttj&t % tmmjor** itar of ite © fsm&r*& wi&fcioB© of tfc© ©stior mimiT* i%%m&f Hmhnk fofo* dooaod of i&loro&t to gQmthosig*

of

i#&t&

mbBttmmts m % % »nitrogon wldX© eo&fizdng t&© otior moioif* to th©

m m m aem* !»#** rnotl*^!, ettogrl, iooftutrl.

i ©©proi^X# x»*l&ty3L&&&

fox itmnd%m^m mfcsiifcwoisi® i t mo tooldM to »«&$ e&sw

temto© wMoh wore d o rlm iiiw of ©ads*® alro&dy knowa to peowm pb^siolo^ioal ao tM .tr.

3 II m m om m *

X#atoefKi& is a fa ta l diae&ea, eeneidared to he jteonl&etle in nature, ntattifo arise® primarily In the bleed forming organs, and 1# tihKkr&eterieed % an, tadmwlTft and abnormal p roliferation of the white bleed. ©ell® and th eir vremwmrn with in filtr a tio n into %h&wmiwm

%%®mm o f the bodgr* eepeelally the bone narrow* saloon sad l$m$k aslK u

In, «m3n»% . eeeee there in m mumt&tod anemia*

tm km im ms& 1?® ©las sifte d on ib® ha»i» oft

(a) the acute**

a®®® o f tli® disorder# {%) the preeeae* o f the XeBtasl© or subleukemic (aloukemie) phase in the bleed# and («) the parent ©oil ^rpe. are tin?®® main type#! ii^aXegemms* Xyaplmfcie and mm®$%ie*

fher# 1st the

ptmm aXX three t^p®® are fa ta l in ftm two to three month®. %®Xegen®ue and lymphatic type® magr mm& in dnronle form and the patient may Hire for two to fir e .years* fhe baste

in leukemia i s an alteration in the mil®

of the bone marrow which result® in p artial or eomplet* imlepen&enee

ftm im iom regelatia^ mmhmn* growth* .and d ifferen tiation of normal leaeoeptea*

Wmmltm Xenfemia nay he Induced ehemte&lly or p!\yolml~

ly* inherited# or transmitted by transplantation of the lirlngf Xeukemie e e ll* to other animal** $he dUaleaX mamlfaet&tlen of laafeeisAa are dependent on the

tmm of

the

■mlooksmlm. In the chronic tom fe«w i s a Ifis# * iwrm^ mil®,

p ls tia

®ha ®pX##s i s shout %m times I ts

liormaX t i f f while Hut lymph sod®# &af# mtmX,

S«gX#M& i s a ^ i

*£©#40.* tli® md hleeft #»& eauttt ##*$#« frost* 2« 000*000 t© 3 *000*000

m il coast ttm 450*000 to 500,000

(soym&X ig 5*000*000) u st the

(m tm l

i s X0*O00) m a l l ferns# fc e isg p r e s e n t .

ft» »torpgvplA gfta iwmlvm the tissue ** thg

most often ®£t®mtm th®

md tn^admX &>&**. Bptmn as&mgmmt i t m t m

u m w tm t*

as i s the

gye&ege&mu In the early stag#®* the r«& ggll emmt and homogXoMs afre mrmX hat anemia ssmXXy develop® i s the latar stages*

fh#

iffeita ©#11 © am i 1® c lm m e to r i s e d % a s a lm o s t eam ltjielre ismreftA* i s

im m tnre J^pligggrtgg, the total ocm st fcetsg tm m than is syoX ogesesg*

!•«*, 100*000 to 150,000 m lees* $M* form i s a lw y s ami® and rapidly fatal.*

ft# mm% i s sterwy.

fe ta l # d t t c o ll ommt i s high with

m m raesocytee o f a ll ago®, lymph sodas ant spleen are ©lightly enlarged. Sh®, s c o t # m yelogenous m d ly m o to tio ty p o s a r e c l i n i c a l l y

sim ilar.

fiw sto n y ossoi i s efcum teriseA V headache, hody m iss*

flUtMSi #sps®m* dSavshgA* gataasties* tmm ®s*d fammrr^mgm tern the

mm * stem s * ia to stis# and bladder*

She spleen i s mt emmn^ m*

larged hat the lymph glands of the neck and im enlarge rapidly.

$ heeeglefcta are mmml hut there i t a.

in it ia lly the ted. c a ll count

r a p i d a n d p*[email protected] r*e#iir« aiawasia w hich aeon d e v elo p s*

W ith in a fm ? wealse

the red c e ll count trepo to nfomb 3,000*000; hemoglobin to white ©all n ew t varies, fiam i appa^Mmatolj 1.0*000 and than rises to -100,000 oonei stin g mostly of immtm® torn® ($}*

In general i t want ho s a lt that there 1# no real cure for asy tom o f Xmfyml:®,* (Bm treatments that «

need c lin ic a lly are

s o l e l y p a l l i a t i v e and te m p o ra ry {6, ?)«

Irradiation hr %»ffflgrs agpea** to he one o f the most e ffectiv e methods for a llev ia tin g T ronic much 10m e ffectiv e in the am t# for® of the dfsees#*

It i s fdnoo repeated

doses hmom loos effective* the more recent trend h&a %mm to %m the sn ail dose technic m& to xim i t only syssptcmati©ally ($}* JttBtt8S£* Altlwugh largely discredited at the present tin*,

hm %&m need with com# mtcmm* Besides Im&m toxic to leucocytes i t in also d etra ctiv e to red corpuscles m& hlood p la te le ts thoroty Intensifying the anemia* A© potassium mmm&tn (Fowler’s oelntlen) arscnie

mtmtimn produces sa il ©factory resu lts, esp ecially in the syslogs&ms typo,

Hewmr, i t i s d is tin c tly in fe rio r to irra d ia tio n ,

Stevsrtho*

lo se , where irradiation in in effectiv e or urmmila&Le or hetweeu irradiation treatmente, ereetde has a useful place. on.

Blood transfusion i s indicated in order

to tid e the p a tie n t mm a c r i t i c a l period and also os an aid in com-

II b a llo t %tm mmi&

l« tMtM&lar « m m oattrowt& of mm&mh. m m r $®>m®

III® &iW$&m

wMdhmma&lmgm wmlm® of tb® mntmmk

smstard m®* M «M^mhlwmttyrl) tmlfi&o# m m tlto o w o d to bm% & tonoflolid mttm*. m Imitem&a..

in a m & m t artlolo ItaroitaMl m&, eo~

utmekmm (9 ) oattMttvl*#& tat* mmi%% of IZf w w of XmSmdn trootoA 1^I& *si%3?©f®s taootftM i*

*m& 2 Bos&oao* of

fkw&pr

i a M ? O m m o f Lffi&tfnl&

%po of 2*®«alwla

BO* 0&fOO

flood

Bmsgwaae lid *

Cteonlo apolooyti# Cfc&oi&e Aaalo m& Oitemto

gfe 15 28

5a 15 0

1 7 £

foos* 11

m M

t e n d in g to t&oao o&t-feasra tho ‘boat av&ilablo oocspotitMlo of t&l* ©oipioo Aftt ®*2» irio fa ^ o h lo j^ o tfe s? -!)

s{ ^cklorootb^X) a»&0»{ 8S»3# and 0C»»X36t liSIM'* lota?a^^ehIw >otifegrX *l» 3 *

wopaaoMaatno,

c i^ { t% a % a } $

*(cas20BSaoi)3

o% < m ^ { a ^ q ^ c i)s

MW

m ,5

flM .36

2-n tho fin a l onaiyoio these ttKfljptitmdo asro aoofal adjw^o to

f

the

1mt mm m b etter than arses&e, bo»i«n«»

of

W i l k i t , WM m fflflWf r

®w> th e r& p e n iic agent® i n r s d t e & e t i r e

im%mm mm %M emn&tlem© arisin g tsm the nuclear toimk&nm of the isotopes*

In thi® respect r&dta&etire rnlmmat* md th eir effm tB mm l o w r e r # th e floe© r« © elv ed % map m m eeXX

s i m i l a r to t h a t o f

i s dependent spent

(&) the deposition m.& metabolism of these agent*

in the ho#'# (h) the h&XMlfe o f the loo top© md i t s degencmtion product® and (c) the penetrability of the muaatioxift ihsmseliree#

M ioaoti'ro phesphorii® ®P$S) in the tmm of dieodim pke®* $ha$#i a beta emitter with a balf«*ll£s of X&*3 days* has received the m ost a tte n tio n *

®o a l e s s e r 4set«nst« r& dieA etiy© s tro n tiu m m d m d im

Mire %mti meet* A® e& Indication of the efffeetiimeee of p3$ !Msn (10) w rites that the mmm® l i f e of patient© with lenkemia i s 3

years eithent tr ©almost* 3 ,5 years when treated with Xtasy* md 3*& years when p3® iS'-tho tMrepoatl© agent*

However* P3® has the &&*»&»

tag® swap 3t*an#s in that i t does not proc&ee radiation sickness* fM p o ^ X ^ ^ o ,

-% rly i n 1 W

JW b » m d

co-workers (XX) reported temporary remissions in children with a&ite Xenkemia when treated with artneptsHn ( I ) ,

However, more recently

BurchomX anti eo*worke?a (X2» 13* 18) demonstrated that « in o p terln produced on!# slig h t « l Irregular a ctiv ity in prolonging the survival time o f .mice with transplanted mouse XeufeiwsiA. H w ® w , Walno**#&* methyl pter#Xgintamic .acid (H ); ^ r fn e ~ 9 ^ e th y l pteroylgXutsurdc

8 acid (If) m& £»&*

( I 'll) | M m tfm p m im ^ ( f ) h*& d e f i n i t e

n a t i v i t y &s d e m o n s tra te d t p

X* I and a* « I NH*.

n . ItX*. itx *

8 * OEjf B* « I B** * s i1 « i1 r/ b

If.

8 end 1* m ® j

COOH

n ?

dnuftling the

mwv&v&l t l m of Mm ©train of mtm

Bad %mn in jected v ith liv in g Xmteemia mlom e s lls ftm m $k k *$$al& a t

fft addition to the $&mt* fe w native eotqpwjii&t* that# m fe m fested

dtfcev wm$mm&&+ fh® f ir s t fm t of $«t>X© II

showed alight %®mdemte awsHv1% t-MXs the r©mal»l»g elgBtr*tm showed m aarfcivitar against He %leakefiain. I t m s aertigad % then# authors (18) that a ll tiie eoimmtnda in th is series wMeh ti&Mftd a d efin ite a ctiv ity against Alt h latiNed*

m m related is* that %%@m ver# amine grma^s in the 2 and h pm itlom of the pfeHMm Mm #*■ 4» the enelegona csnfignrntlon in th© 2*&* dleaAnagiiuriiket f-Mpiw and m^msfkem (19) recently teeted a ©srls© of

9 tmm i s 3W9ISpwSSM8fiiKM8BBwjS^^

&ei& e m id (Mw&Uwin) ty&pprStald&ftft

alms

Z»M 3ti»&§^aiaeatylaalEOpjrrlBi dim

tf k^M m im ^S ^^W iW ^^d im 2* 2*^ M ^ E o ^ ^ ^ lx o 3^i^itsd€[email protected] 2*5~M®&&0-4 # fli»* 2* 4 ^ i E i ^ t o ^ 5 ^ d i l . o i ? o 3 c # t e i d o i^ T im ia i^

2* ^ B i3^ar0^ 5, 2# tr d|^rlBidlE0 2# 6mMl^e^^$^rm&w^%mi as

Z»^,d#*liil^^o^pyM.miaiiit#

fli&&

2 , *>#5* ^ ^© tral^rdro^srpp'iaii &i$ $

2#4,&*&£ dilWOTrifiJiMsi# 2~ (& l0 r® ^ ^ U m k i& lm tm » & ~ m % ty rip w i® i &*»&

3Li*Btttyl^2-lai^M#€5r3^X#fc, 5*&*$^ s^ to p a rriia iiln ©

m

tmm u

OgBposttd

Kegjawdjgatrtigilianeg (eoni.) X*J~Mn(SN»fcl^Xta$l

aims

?Jr£X.W&S8$i. 2 ^ M m & m p % m tl M m 2* ^ l ) l » i a i s ^ f ^ m t ^ l p l ^ l M m #

2t ^$iami&Q*4 a^dil'^dx^^T^exidimt 2* VlS|j0s4!MMSf f w i i |> t e ^ ||» t e ,i l l l a #

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^ ^ | t i 0 ^ r l p t i s r l al&ft

Fteroyl^Xuteric acid P& arc^M ^ntagtic acid W^m 0^ 0 ^p%mwlg!Xtri»®4« acid $k&£mma&&® m to lo g o f « iiM $ p tix lj^ Ftcro^l^X & iim i© a c i d V ~ f * Fi«w srX **sw rti& acid (d)

FtcrcrXassimrtie acid {r&ccsde) ^w.Mlno**[email protected]?cyl ®Xm%m

n tm m n tmm*) S esp M s

igalssst Ate k % msk,mifo

aS888»BW8»i^

m id

X*SJ?S&®i&6

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M e n ifis i l l j Il

la sa tM n #

h

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{C&r&nmOia&l&e}

line )* 8~

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(a) pr^iisiaiiio W M W illW ttW m H >M l»— IH -W W i|>.

>■W *1l/.»*w »ltot

m M rt MW^^inil|^W^l«>4*lw>i i i »»

$t£gKl m % m tlln® If- C ^ b ® * fo ® ? ^ ® rp h # lim

M fo yt MWl tM f t m t a m f c * WtoyX ^ p k m s g l %hMms%mm%%

Rtlgrl %*thimpmtyt

m w l o f a seareh. for

SMlO*(X*

CHZMH C O O CH* C H * 5 C Hz C Hz CJL

teior grow th tidsiM ter®in m i®end sd o * -* « o X © g ie& Xdata

m

Aswc

glim*

OarhaM© acid dnecmooe® snoahaneeusly mft is not known i& babooes *

the free state*

- 2 £ L , H2sco ret

J R

» m > o i + {%

B o w se r* it s sa lts are wore otahle*

itoeatos c a r te l

at©wfi he fmmd txm tw oneleoi& oe of amnt* and o n e- of carbon dioxide in petrolm ®ether,

fhe w hite nrsrstals

00$ ♦

he © n eio x d n

----- * H^COOM!^

and earfcon dioxide © * *teatiisg at < $ 0® f #» heated under eam snre urea

Is fomfti*

So6iu® ©arhamat® eaa he forced hr

2 « = £ {!% )#% fh© AAtnr« o f « w h » ie m®id* loosely g&UM umtlims* ar# HglTO®B Terr stable eryat»3Xi»e snbateea® tm m llr mMhl® in alcohol* ether* m ter sad dr&©ro£®m.

0arha»t©ss tm& he f o » s t V &

©f differ*

«sit tt«ihed*i (a) V the mAtlAA o f alfcyl ehim m [email protected] with mteniA or ^aine% SKMIg * 0&0Q(A» ---- * JMTOE* ♦ MfjOl (b) %* tTAAttng a t itf t a g l ehXaride with on alcohol or ptw el*

mmmm, * m m

►moatm* * ecu

t&) % heailag urea with am aXeahaX at a high te i^ e m te e (23)* 08 mrnomw

(#)

oMtnld# into alcohols (3&)*

mm * 2%hjjOK — * % w o c y ^ * Ogjfga (#) l3§r the ftnUftft of »m©®&a at ©iHliiMf [email protected] s f# » k s s vcpm carhoai©

«*ta*« {^)* o c& tt^ jg * » | — *

+ ozwgm

and (&) % tii© aeftlon of ettSMffiia on &&m®mrhmtv eotere {$*)*

woimoffy * « 3 — * s^ m oe^ tj * x%or A

modification of (a) i« afforded t r & » » ^ of

fmoiiomo -wfeEctt load to tli© fom&ieti of an feo«$wsafc© in the isrooone# o f tli#

tslmhot* Them a n t th© Sofmsim Inmostd* mrnetim

s ta rtin g with an m%$®$

mm% + m.^ _» H8HC008*

and the Looecn roaotion «tortlx& with the hen&eyl f^dressmie acid,. RCOKWCOCgHj - g t0n > (HBCO) —B>0TL » KSHMOR*

rat Metho&e (a)# (t>) and the Hoitann modification of (d) as*# th© most nppMc&M© to the osrnthoois of B*mfc©Mtnt©d c&rhMmt©® and w ill,

ao tfeatyoCOPtt*

ih©

attention*

$te*g*o&» (e)* (o ), (f) and (c)

«oni of l i t t l e m in i in tfcio work w d w ill 110% %* dooeyitoft tethor* m itittoV B ft of msmhsiitutod awtbm^ eotora wo in gooogal thoo* of htifi m « * % or andan acid ss& i& e(aft)#

turn stable © o d ln ra

dorimiivoa w hich ro& et w ith olhyl andacyl halides to £ive B -m shsti**

tatod m&hftfto,

Wm

IMdAyiatad wotta*© react with niton** md s&irie

acid to g lw l^M irom and fe d tr o cojs^nds. K iw i s& osio**m sftfititutad

ffoo reduction of those

Xhwtbom in n^toam solution ro& et

with chloric© to giro SMSi derimtlvoo*

%&*o3yei* V either &X&&M

m add dteoapoftoo wetfeaas to «boi* dio.ildo, a»eni&and the comesponding oloohol* &(#MUU$ potaooioa hr&rad&o c o a w ts uyetttaft* to the ooryetfm dliig alcohol andp o tao ol« opy&ate,

In ardor to illu strate the m*o ii^ori&ni methods of ssnsr thooio of &mfe*t£tfite& ear%«teo,. a » t « r of go-looted emsrmle® w o fceareia given. ^ o&cellaftfe pro* aodtere for the pronamtion o f ot&yl JMaetfcgrl ewfcamto is gimn hr SBSPtaoii and Bfotdm ($$)*

titina an other solution of oihyl ehlwo--

oarlMmato mo atianrod with a oold afuoous solution of meth^l&sine in mfM% * aoooegRg ♦ m m — * m,%mmm$w$ * & & * i%o the vtf&mnm of aoditHR hydread do solution they© m s ohtainoi* of tor d istilla tio n o f tho prodnot, «& B&*90$ y ield of the tw o MrtNUMft** QWtasato* derived tmm IW nlm epittoliao wer® ohtainod in

mSL stain#* ($£) w&en m ether solution of

good yioM g

IM® a^&n# w o treated nitfe m oli^M exe#«s of th» &H$rX ^oroes3% o»* at# in t&e preoona# of a onturatot solution of «#aitoa

®»

len t* nllsjrl ^#a?o«i% on#t#i g$m 8Cu$®^ fie ld # , 1mt th# y ield s dropped

+ acooR NHZ

MHCOOR

#0 the H group increased In e l m* wo that the fie ld of the n«&#xp3. d#rImtlT# was only aSwnt X#* Gan^s (2?) fle e t &»8«rlfea& the prmmmttm of etfcyl IMSpyrld^X) m rham ie % the M illio n of em ether solution of 2**vmlm-

pyridine to gm ® % hmsolution of ethyl oKloeoesrtfomto follows# Xy digestion of the p recip itate In sodium m&tm&to* solution*

Although

no mention wm mSk o f ylelclt* Ctapss did export the m m m m of di»

>MH

N+ H Cfl"

^NHCOOCaH

pyrldyl m m in the reaction edntxxr#.

Howvw, the preparation. of ethyl H*(5~iede~&*pyriflyl) cartn

zz fc&s toea

I(T^\

t r BerattaAa md ^worfeara (20)*

+ « C Q .C i Hs-

(f^\,

M « te

■»• C fH ^ N hOL

mmmk of

m ln tt.m « f etf^rl ablora SawcitoXXX of the Xfa&mmity of 8&Xif©risXa at I*©® A^eXo®

who i® t o tin g to il*

m l ptfopsrfcias.

t o to u h ilitio ®

as*® g to a in f&t&X® I* t%is ia to estla g to mot® t o t in this host©Xogons ««$!$$ ait Iiw m ® im mol®®!*!®*1Wtti&frfc % m

grmp

imXims t o so lto litg r .

t o host proea&xro for t o p^®p&raticm of t o t aeries of o&shm&to was developed m a resttll of sow# twenty oM efxpart&siifte

m&imu m oiifim ^iom o f t o ooMoaa&tioa hotoei* p^fd&to «md sm a&hgft

* Bio proeadsre t o eh m s

fias&3$r w s d fefr t o prapflm tiea of to® series m s ohmm On t o ta a le o f y ie ld ©fct&tod* aa&e of operation* and te s t of separation and p urification of t o desired pro&M&i# t o rotation m& proeate® to'M ft me* as fo X to st

*2 CfCOOR

C ^ ^ -N « C O O R

-7 U/HITC 50CID

+

C^N H CN H 'C^ 0

3B

fm ms!** of aHiyX felor oasrfeimt e dim olm d in e©M ^ m m m§ fem fed a*opwls© w ife a %mmm mln%fm. of m® mol® of &» srtstopyriitix©*

4 white solid o f vttimam m m m iM m tommU which m

feft&tlttg la hssissfts- dsooaapoasd to iho sgrtmat©, l^droeKtorido* ©ifebsn dlosdcl® md Mpyridyl tots,.

SspsHttioa m s

saslly offmiM % the f&ot feat the 3*aiE&fiop$ri m cltor

loilim g tlw 9