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Further reproduction prohibited without permission. *&i® author to his grntltwia to Br* ®* S* Kwiitim# UWM^LHfc^^fk- ro ^JBM-J-Ji w■*>- 515 fla* fTthf* *tJ»L* jH9L. ^ w @ #AfcW^ttk WMi*EIkwJ0*I frajMmwi Wi&9#i(M €^3l wt#jaa W[r .._ O--■* -Ea-a.* K^| » ^133 »v £^IliEP-ju *aN— %E ._■ —ttjt Satta and tapaagr for a research gjMiru&ajk smih sJLb* 396004 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. fable ©f ioaienta V tf* . X* Introduction . . . . . . . . . . . . . * . . . . . ' 1 XX* irej&jitaX lepreeentation of Ite&otioae* * * , * * * $ XXX* Discussion . . . . . . . . . . . . . . . . . . . . 7 If* BxperXffient&l * * * * * » . • • • » # » • « . . • * X® A# Preparation of 2-{p«araonophenylaraino)-3- nitr ©pyridine and related eoi8p©und8, * * * * * X® 1* 2 -Ohlor© ~$ «*ni tropyrldlne 2* 2-Cp~Aalnophenylaaino)-5-.nitropyrldin© 3. 2 - Cp-Arsonophenylintln©) *5 -nitr ©pyridine 4 * 2-(p -Ar ® enosophenylasiino} -5 -at tr ©pyridine S# 2-(p-Arsonopbienylaiaino)-S«a!ninopyridine 6* 4-£2* -(5* -AidinopyridylJJ-aialnophenyl- ar seal ©tie acid 1* freparatlon of 2 - (a-araonophenylaiaiBQ) -5 - ■ nitr ©pyridine and related oompsnmde* * * ♦ * .* li 7, 2-(««Jy®ln©phenyla®ln©) -S -nitropyridtne 8. 2*<m»Arsofnophenylamin©)-6-*nltropyrldine 9 • 2- (ei-Ar senosopiienyla®ino) ~S *ni tr ©pyridine 10* 2 - (m-Ar eonophenylamino} -5 -aainopyrt&ine #* Preparation of 2- (1* -benssotriaeolyl} -S-arsono- pyridine and related compomda # * * , , * * *. 21 11* 2- (o-Aiainopheaylsod.no) -5 -nitr ©pyridine 12. 2-(l*-Beneotriaeolyl)-5-nitropyridine 12* 2-(l* -Benaotriaaolyl)*5-aninopyrldlne 14* 2-cl*-Benaotriezolyl)-5-areonopyridlne IS. 2-fl1 -Benaotriaaolyl) -S-areenoaopyridine U* Preparation of 3-ni tro-4 - (p -arsonophenyl- anino)-pyridine and related compounds, * * * * 2§ 16 * Chelidonlc acid 17, Ohelidaxalc acid 18, The nitrate salt of 4-hydraxypyrldlne 19* 3 -Ifi tr © -4 -hydroxypyridlne 20, The hydrochloride of 3<-nitro*4<*©hl©r©- pyrldine 21 * 3 -N1 tr o-4 - (p -aminophenylamiao) -pyridine 22# 3-Hltro-4-ip-ar®«no|rib.ei»l»diio)-pyridine. 23, 4 - £4* - (3* -litropyridyl) J -amtnophenyl - arsaniouo aold Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. 1* "tatrodnotion 1 Since Shrlleh* e ayntkssi s of a^aphenajolii© the useful* ness of organic derivatives -of arseni© in'the "field-of chemotherapy has steadily-increased* However, Ike met'-of Many of such mwm&mX® is United because of Ike t«ati©iby* caused by their astiOn# toward the human system. 2a this connection the me# Of two organ!© arsenleala ■ will be briefly reviewed* • ■ Atm yl {Ike »«ao*e@ilw eell ©f p*e®la^toeiylttr»«ftie aeidj Is M©r® ©ff©otiv© th*** inorganic ' srsonlo In the tr®ati&tet of teypte©s©*®laai## However, Iks drug 1» espe* eially dangerous beoam®.® of ©file injury and blindness which result Mai il* use, ■ ■■ fiypsy§*SBid# (4 -arsonophenylglyoineamide), derived ■ t ■ trm at©*yl by Jacobs end B®id®ib©a?i©pf le need in the tr®at»««ib of' Idle central nervous. systte ■ syphilis m S in trypttoscwlasls* Cases of ©ft!©' injury and blindness have resulted also from the mm of Ibis tohpONMft* lino# no I*pyfiay!*4teiwaily*« of p~a»in©ph©nyi~ arsonle aeld have been reported in the literature ted be* d#-d cause Bins ted Balk ' have found that certain d-substi- ' luted derivatives of b«te*te©ffridi»® have therapeutic value It was the purpose of this investigatlte to study organ!© arsenical® of the following b|jt«#t 1. H-Pyrldyl- derivatives Of p-amlnophenyl&rson!e sold which also otetained a free ante©- gromp on the pyridine nuoleus* .§ Sinse the'.start of the investigation, infoi»ti« Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. t* , has been re©®fve4 to the effeeb that a m©lamia© dertw* ative of p •as&nophenylar sonie aeid width- probably ha® the following atnwetm1© H HHa a . . H /H=CV t O ' - w H MR* has been used affectively In the treatment of aleeping. sickness and 1a -reported to have little or no .,■■■. offset upon the ©ptie nerve* $* I~Pyridyl~ derivatives of m#easiao^enflar#oai« aeid abieh'alae have a free ipia® gritf on the pyridine. - aaelema* dliiioiigii it ie diffienlb to establish any tafalil* bl© rale*.'relating eihwalftaX e«etitatl* *»d therapeutic &et3 vity, ¥©mg and hoeventoart: observed that tonicity fw the opt!# nerve appear* to be connected with - the siiiatt tubed ante© group in. the pOeitfoa para* to the arsenic. Similar aoapoaariUi with the araenio in the ortho* or note* poeltioii are apparently free of thle danger* 3 . a *(i» • ^ a a o tria a ® ly l)* i« a r* « o ^ rid in e * Reproduced with permission of the copyright owner. Further reproduction prohibited without permission.