NO159677B - Fortykkende blanding, samt anvendelse av den. - Google Patents

Fortykkende blanding, samt anvendelse av den. Download PDF

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Publication number
NO159677B
NO159677B NO820350A NO820350A NO159677B NO 159677 B NO159677 B NO 159677B NO 820350 A NO820350 A NO 820350A NO 820350 A NO820350 A NO 820350A NO 159677 B NO159677 B NO 159677B
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NO
Norway
Prior art keywords
benzoazadithian
sulfamoyl
dioxyd
lower alkyl
disulfamoylmercaptobenzene
Prior art date
Application number
NO820350A
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English (en)
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NO159677C (no
NO820350L (no
Inventor
Syamalarao Evani
Original Assignee
Dow Chemical Co
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Publication date
Application filed by Dow Chemical Co filed Critical Dow Chemical Co
Publication of NO820350L publication Critical patent/NO820350L/no
Publication of NO159677B publication Critical patent/NO159677B/no
Publication of NO159677C publication Critical patent/NO159677C/no

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Description

Fremgangsmåte ved fremstilling av terapeutisk virksomme benzoazadithianer.
Foreliggende oppfinnelse angår en fremgangsmåte ved fremstillingen
av sulfamoyl-2, 1 ,4-benzoazadiethian-1, 1 -dioxydforbindelser som har diure-tiske og saluretiske egenskaper og som derfor er nyttige ved behandling av tilstander som er forbundet med unormal væske og/eller elektrolyttilbakehold-else.
Dyreforsøk har vist at fremgangsproduktene ikke er giftige i virksomme doser og at mens utskillelsen av natrium- og kloridioner er betraktelig høyere for fremgangsmåte-produktene, bevirker de ikke en så øket utskillelse av ka-liumioner som ved andre kjente diuretica, særlig som thiazid-diuretica.
Ifølge oppfinnelsen fremstilles benzoazadithianer av formelen:
og fysiologisk godtagbare salter derav, hvor R<*> er hydrogen, halogen (dvs. klor, brom, jod, fluor), trihalogenalkyl, særlig trifluormethyl og triklorme-thyl, lavere alkyl, lavere alkoxy, nitro eller amino, R <2> og R <3>, som kan være like eller forskjellige, er hydrogen, halogen-lavere alkyl, lavere alkyl, fenyl-lavere alkyl, lavere alkoxyfenyl, eller sammen med ringcarbonatomet
2 3
til hvilket de er bundet, kan R og R danne en eventuelt lavere alkylsubstituert cycloalkylgruppe med 5 eller 6 ringcarbonatomer, R <4> og R <5>, som kan være like eller forskjellige, er hydrogen eller lavere alkyl.
De ovenfor beskrevne forbindelser kan opparbeides for oral administra-sjon ved å tilblande en tilstrekkelig mengde aktiv bestanddel til å frembringe en diuretisk og/eller saluretisk virkning med de vanlige fortynningsmidler, ekstendere, bindemidler og/eller smøremidler som anvendes ved fremstilling av kapsler, piller, tabletter eller pulvere eller de kan inkorporeres i eleksi-rer. Dessuten kan forbindelsene oppløses i vandige media egnet for parente-ral injeksjon.
Benzoazadithianforbindelsene fremstiltes ifølge oppfinnelsen ved at en 2, 4-disulfamoylmercaptobenzen-forbindelse av formele!*:
14 5 hvor R , R og R er som ovenfor angitt, omsettes med et aldehyd eller keton av formelen:
eller reaktive funksjonelle derivater derav, hvor R <2> og • R <3>er som ovenfor angitt, og når R<*> er nitro, reduseres denne gruppe eventuelt til amino, og at den dannede forbindelse eventuelt overføres til et salt på i og for seg kjent måte. B.eaksjonen lettes ved moderat oppvarmning av reaksjonsblandingen som med fordel innbefatter et oppløsningsmiddel og en uorganisk (passende saltsyre) eller organisk syre. Benzoazadithianet er vanligvis uoppløselig i reaksjonsblandingen og kan lett fraskilles.
Fremgangsmåteforbindelsene ble prøvet ved følgende metode:
Dresserte tisper av blandingsrase i den postabsorptive tilstand ble gitt 500 ml vann oralt og 3,0 g creatinin subcutant. En infusjon av isotonisk fos-fatpuffer inneholdende mannitol ble infusert i en mengde på 3,0 ml/min, og etter 20 minutter ble urinblæren tømt ved kateter og gjentatte urinprøver ble tatt med 10 minutters mellomrom, idet venøse blodprøver ble tatt ved midt-punktet mellom hver urinprøve. Etter denne kontrollfase ble den forbindelse som skulle prøves, injisert intravenøst med en begynnelsesdose på 1,25 mg/ kg °g ytterligere mengder av forbindelsen ble inkorporert i infusjonsmediet i en mengde på 1,5 mg/kg/time. Etter en 20-minutters likevektsinnstillings-periode ble gjentatte 10-minutters prøver av urin og blod tatt. Bestemmel-sen av natrium, kalium og klorid ble gjort.
Resultatene av like store doser er vist nedenfor i tabellen som gjennom-snittet av tre kontrollfaseresultater og tre drogefaseresultater.
Av tabellen fremgår at der ved fremgangsmåteforbindelsene fåes en mindre utskillelse av kalium enn ved det kjente diuretikum "Diuril", hvilket er en fordel.
Av disse resultater fremgår at de to første forbindelser i tabellen er de beste på grunn av den samlede virkning idet 3-klormethyl-6-klor-7-sulfamoyl-2, 1,4-benzoazadithian-1 ,1 -dioxyd oppviser den mest markerte økning i natrium- og kloridutskillelsen, mens 6-klor-7-sulfamoyl-2, 1, 4-benzoazadithian- 1,1 -dioxyd foruten en betraktelig øket natrium- og kloridutskil-lelse samtidig viser en relativt liten økning av kaliumutskillelsen.
Disulfamoylmercaptobenzenutgangsmaterialene er også nye forbindelser. De kan fremstilles ved å omsette den ønskede 2, 4-disulfamoylhalogen-benzen med natriumpolysulfid. Reaksjonen lettes ved moderat opphetning av reaktantene oppløst i et oppløsningsmiddel. Den således fremstilte disulfamoylmercaptobenzen kan utvinnes og renses ved konvensjonelle fremgangs-måter .
Di(alkylsulfamoyl) -mercaptobenzenforbindelsene , særlig de som har en 5-trihalogenalkylgruppe, kan også fremstilles ved å diazotere et 5-R<*->2,4-di-(alkylsulfamoyl)-anilin, derpå omsette den dannede diazoniumforbin-delse med et atkalixantat (passende natrium- eller kaliumxantat) hvorved man får, etter alkalisk hydrolyse , 5-R<*->2,4-di-(alkylsulfamoyl)-mercaptobenzen-forbindelsen. Denne forbindelse cycliseres så ved den ovenfor beskrevne fremgangsmåte til sluttprodukter med den ovenfor angitte struktur hvor R <4>
5 og R er alkylgrupper.
Oppfinnelsen vil bli beskrevet mere detaljert i de etterfølgende eksemp-ler.
Eksempel 1
6-klor- 7-sulfamoyl-2, 1, 4-benzoazadithian -1 , 1 -dioxyd
Trinn A: Fremstilling av 5- klor- 2, 4- disulfamoylmercaptobenzen
En blanding av 6 , 0 g 2, 4-disulfamoyl-1, 5-diklorbenzen, 5,0 g natrium - polysulfidnonahydrat, 1,0 g svovel i 150 ml ethanol oppvarmes under tilbake-løp i 1,5 timer, avkjøles, filtreres og konsentreres til tørrhet i vakuum. Residuet oppløses i'50 ml mettet natriumbikarbonatoppløsning, behandles med trekull, filtreres og syres med saltsyre. Produktet oppsamles og renses ved omfelning fra vandig natriumbikarbonat, hvorved man får 5-klor-2, 4-disulfamoylmercaptobenzen med smeltepunkt 282 - 285°C under spaltning.
Anaiyse beregnet for C6H7C1N204S3: C 23,78; H 2,33; S 31,70
Funnet: C 23,70; H 2,25; S 31,56.
Trinn B: Fremstilling av 6- klor- 7- sulfamoyl- 2, 1, 4- benzoazadithian -
1, 1- dioxyd
En oppløsning av 3,0 g 5-klor-2,4-disulfamoylmercaptobenzen og 0,3g paraformaldehyd i 60 ml ethanol og 60 ml 6 normal saltsyre oppvarmes under tilbakeløp i 4 timer og avkjøles. Bunnfallet oppsamles og omkrystalliseres fra ethanolvann, hvorved man får 6-klor-7-sulfamoyl-2,1,4-benzoazadithian-1,1-dioxyd som farveløse nåler med smeltepunkt 259 - 262°C under spaltning.
Analyse beregnet for C7H7C1N204S3: C 26,68; H2.24; N8.89
Funnet: C 27,14; H2.59; N8.79.
Eksempel 2
6 -methyl - 7 - sulf amoyl - 2, 1 ,4 -benzoazadithian -1,1 -dioxyd
Trinn A: Fremstilling av 5- methyl- 2, 4- disulfampylmercaptobenzen
En oppløsning av 10 g natriumpolysulfidnonahydrat og 2,0 g svovel i 100 ml ethanol oppvarmes under tilbakeløp i 30 minutter. ,11,2 g 5-methyl-2,4-disulfamoylklorbenzen tilsettes og oppvarmningen fortsettes i 18 timer. Oppløsningen konsentreres til tørrhet i vakuum og residuet omrøres ved vaerelsetemperatur med 100 ml vann og 25 ml natriumbikarbonatoppløsning og behandles derpå med trekull, filtreres og syres. Produktet oppsamles og omkrystalliseres fra vann og et spor ethanol, hvorved man får 5-methyl-2,4-disulfamoylmercaptobenzen som smeltepunkt 228 - 231°C.
Analyse beregnet for <C>^HjqIS^O^: C 29,75; H 3,57;, N 9,91
Funnet: C 29,91; H3.59; N 9,80
Trinn B: Fremstilling av 6 - methyl- 7- sulfamoyl- 2, 1, 4- benzoazadithian -
1, 1- dioxyd
En oppløsning av 2,8 g 5-methyl-2,4-disulfamoylmercaptobenzen og 0,4 g paraformaldehyd i 30 ml ethanol og 30 ml 6N-saltsyre oppvarmes under tilbakeløp i 18 timer og konsentreres til tørrhet i vakuum. Produktet omkrystalliseres fra ethanolvann, hvorved man får 6-methyl-7-sulfamoyl-2,1,4-benzoazadithian-1,1-dioxyd med smeltepunkt 234 - 236°C under spaltning.
Analyse beregnet for CgH10N2O4S3: C 32,60; H 3,42; N9.52
Funnet: C33.12; H 3,81; *N 9,38.
Eksempel 3
Spiro-[6-methyl-7-sulfamoyl-2,1,4-benzoazadithian-1,1-diosyd-3 ,1' - (41 -methyl) -cyclohexan] s En oppløsning av 2,8 g 5-methyl-2,4-disulfamoylmercaptobenzen og 4-methylcyclohexanon (1,2 ml) i 30 ml ethanol og 30 ml 6N saltsyre oppvarmes under tilbakeløp i 4 timer og konsentreres til tørrhet i vakuum. Produktet oppsamles og omkrystalliseres fra ethylacetathexan, hvorved man får spiro- ^6-methyl-7-sulfamoyl-2, 1, 4-benzoazadithian-1 ,1 -dioxyd-3 ,1 '-(4<1->methyl)-cyclohexan^med smeltepunkt 209 - 211°C.
Analyse beregnet for C^H^Is^O^: C 44,72; H 5,35; N 7,44
Funnet: C 44,96; H5.56; N 7,48.
Eksempel 4
6-brom-7-sulfamoyl-2,1,4-benzoazadithian-1,1 -dioxyd Denne forbindelse fremstilles ved å erstatte 2,4-disulfamoyl-1,5-diklorbenzenen anvendt i trinn A, eksempel 1, med en ekvivalent mengde 2,4-disulfamoyl-l, 5-dibrombenzen og ved å anvende reaksjonsbetingelsene og de andre reaktanter i trinn A og B av eksempel 1.
Eksempel 5
2-methyl-6-trifluormethyl-7-methylsulfamoyl-2, 1, 4-benzoazadithian- 1, 1 - dioxyd
Trinn A: Fremstilling av 5- trifluormethyl- 2, 4- di-( methylsulfamoyl)- mer-captoberizen
En oppløsning av 34,7 g (0,1 mol) 5-trifluormethyl-2,4-di-(methylsul-famoyl) -anilin i 200 ml IN natriumhydroxyd behandles dråpevis ved 0°C med en kold oppløsning av 7 g natriumnitrit i 175 ml konsentrert saltsyre. Di-azoniumsaltet tilsettes så til en oppløsning av 40 g kaliumethylxanthat i 150 ml vann holdt ved 80°C. Bunnfallet fraskilles og oppvarmes under tilbakeløp i 3 timer med en oppløsning av 86 g kaliumhydroxyd i 150 ml ethanol og 75 ml vann. Oppløsningen fortynnes med 1 liter vann, filtreres og syres koldt med saltsyre. Produktet oppsamles og omkrystalliseres fra alkoholvann, hvorved man får 5-trifluormethyl-2,4-di-(methylsulfamoyl) -mercaptobenzen.
Trinn B: Fremstilling av 2- methyl- 6- trifluormethyl- 7- methylsulfamoyl-2, 1, 4- benzoazadithian- 1, I - dioxyd
Dette produkt fremstilles ved cyclisering av 5-trifluormethyl-2,4-di-(methylsulfamoyl) -mercaptobenzenen erholdt som beskrevet i trinn A, ved omsetning med paraformaldehyd ved praktisk talt' samme fremgangsmåte som beskrevet i eksempel 1, trinn B.
Eksempel 6
2-ethyl-6-methoxy-7-ethylsulfamoyl-2, 1, 4-benzoazadithian -
1,1 -dioxyd
Trinn A: Fremstilling av 5- methoxy- 2, 4- di-( ethylsulfamoyl)- anilin
32 g (0,1 mol) 5-methoxyanilin-2, 4-disulfonylklorid tilsettes] poEsjons - vis til 150 ml 40 %-ig vandig ethylamin og oppvarmes på dampbad i 1 time. Blandingen avkjøles, og produktet oppsamles, vaskes med vann og omkrystalliseres" fra ethanolvann, hvorved man får 5-methoxy-2, 4-di-(ethylsulfa-moyl)-anilin.
Trinn B: Fremstilling av 5- methoxy- 2, 4- di-( ethylsulfamoyl)- mercapto-benzen
Produktet erholdt i trinn A diazoteres og omsettes derpå med kalium-ethylxantat ved fremgangsmåten beskrevet i trinn A av eksempel 5, hvorved man får 5-methoxy-2, 4-di-(ethylsulfamoyl)-mercaptobenzen.
Trinn C: Fremstilling av 2- ethyl- 6- methoxy- 7- ethyl- sulfamQyl- 2, 1, 4-benzoazadithian - 1, 1 - dioxyd
Forbindelsen erholdt i trinn B cycliseres med paraformaldehyd ved praktisk talt samme fremgangsmåte som beskrevet i eksempel 1, trinn B, hvorved man får 2-ethyl-6-methoxy-7-ethylsulfamoyl-2,1 , 4-benzoazadithian-1, 1 -dioxyd.
Eksempel 7
6-methoxy-7-sulfamoyl-2,1 , 4-benzoazadithian-1, 1-dioxyd
Trinn A: Fremstilling av 5 - methoxy- 2, 4- disulfamoylklorid- benzen
0,5 mol m-kloranisol tilsettes dråpevis"i løpet av 1 time til et over-skudd av (ca. 400 ml) klorsulfonsyre avkjølt i et isbad. 350 ^ natriumklo-
rid tilsettes porsjonsvis i løpet av 2 timer, og blandingen oppvarmes i et ol-jebad i ca. 3 timer. Etter omhyggelig avkjøling i et isbad behandles reaksjonsblandingen med 1 liter isvann, produktet som utskilles taes opp i ether, vaskes med vann og tørres. Oppløsningsmidlet fjernes ved fordampning, og residuet, avkjølt i et isbad, behandles med 150 ml 29 %'ig ammoniumhydroxyd. Når den kraftige begynnelsesreaksjon stilner av, varmes reaksjonsblandingen på dampbad i ca. 1 timer, avkjøles og den utfelte 5-methoxy-2, 4-disulfamoylklorbenzen oppsamles.
Trinn B: Fremstilling av 5- methoxy- 2, 4- disulfamoylmercaptobenzen
Dette produkt fremstilles ved å omsette 5-methoxy-2,4-disulfamoylben-zen med natriumpolysulfid ved praktisk talt samme fremgangsmåte og under
anvendelse av de andre reagenser i eksempel 1, trinn A.
Trinn C: Fremstilling av 6- methoxy- 7- sulfamoyl- 2, 1, 4- benzoazadithian - 1, I - dioxyd
5-methoxy-2, 4-disulfamoylmercaptobenzenen cycliseres med paraformaldehyd ved praktisk talt samme fremgangsmåte som .beskrevet i eksempel 1, trinn B, hvorved man får 6-methoxy-7-sulfamoyl-2, 1 , 4-benzoazadithian -1,1 -dioxyd.
Eksempel 8
3 -diklormethyl-6-methoxy-7-sulfamoyl-2, 1,4-benzoazadithian-1,1 -dioxyd
5 -methoxy-2, 4-disulfamoylmercaptobenzenen fremstillet i eksempel
7, trinn A og B, cycliseres med dikloracetaldehyddiethylacetal ved fremgangsmåten beskrevet i eksempel 1, trinn B, hvorved man får 3-diklormethyl-6 - methoxy-7 -sulfamoyl-2,1,4-benzoazadithian- 1,1 -dioxyd.
Eksempel 9
6-nitro-7-sulfamoyl-2, 1, 4-benzoazadithian-1 , 1 -dioxyd
Trinn A: Fremstilling av 5- nitro- 2, 4- disulfamoylmercaptobenzen
Denne forbindelse ble fremstillet ved å bringe 5-nitro-2,4-disulfamoyl-kloridbenzen til å reagere med natriumpolysulfid ved fremgangsmåten og under anvendelse av de andre reaktanter beskrevet i eksempel 1 , trinn A.
Trinn B: Fremstilling av 6- nitro- 7- sulfamoyl- 2, 1, 4- benzoazatithian- l, 1 -
dioxyd
5-nitro-2, 4-disulfamoylmercaptobenzenen fremstillet i trinn A cycliseres så ved omsetning med paraformaldehyd ved fremgangsmåten beskrevet i trinn B i eksempel 1, hvorved man får 6-nitro-7-sulfamoyl-2, 1,4-benzoazadithian -1,1-dioxyd.
Eksempel 10
6 - amino -7 - sulfamoyl-2, 1,4 -benzoazadithian - 1, 1 - dioxyd
En oppløsning av 3,25 g (0,01 mol) 6-nitro-7-sulfamoyl-2 , 1, 4-benzoazadithian-1, 1-dioxyd (fra eksempel 9) i 500 ml 50 % ethanol-vann hydrogene-res i nærvær av 400 mg platinaoxyd ved værelsetemperatur i et Parr-apparat. Katalysatoren fjernes ved filtrering, og oppløsningen konsentreres til tørrhet i vakuum. Residuet omkrystalliseres fra alkohol-vann, hvorved man får 6-amino-7-sulfamoyl-2, 1,4-benzoazadithian-1, 1 -dioxyd.
Eksempel 11
3 ,3-diethyl-6-klor-7-sulfamoyl-2,1, 4-benzoazadithian-1-^ 1-dioxyd
Denne forbindelse fremstilles ved å erstatte paraformaldehydet i eksempel 1, trinn B, med ketalet, 3, 3-diethbxypentan, og ved å anvende de andre reaktanter og praktisk talt samme reaksjonsbetingelser som der an-
gitt.
Eksempel 12
3-benzyl-7-sulfamoyl-2, 1,4-benzoazadithian-1, 1 -dioxyd
Ved å erstatte 2,4-disulfamoyl-l, 5-diklorbenzenen anvendt i trinn A
i eksempel 1 med en ekvivalent mengde 2,4-disulfamoylklorbenzen og anvende de andre reaktanter og reaksjonsbetingelser beskrevet der, fremstilles 2,4-disulfamoylmercaptobenzen. Denne forbindelse kan så cycliseres ved å bringe den til å reagere med fenylacetaldehyd ved fremgangsmåten beskrevet i trinn B i eksempel 1, hvorved man får 3 -benzyl-7-sulfamoyl-2 ,1, 4-benzoazadithian-1,1 - dioxyd.
Andre 7-sulfamoyl-2, 1,4-benzoazadithian-l, 1-dioxyd-forbindelser fremstillet ved fremgangsmåten beskrevet i eksempel 1, trinn B, under anvendelse
av mellomproduktene erholdt som beskrevet i trinn A av eksempel 1 eller 2, er identifisert i tabell I. Disse forbindelser ble fremstillet ved å bringe en 5-R<*->2,4-disulfamoylmercaptobenzen hvor R* er klor eller methyl som angitt i tabellen, til å reagere med det passende aldehyd, R 2CHO, også identifisert i tabel - :i: len, hvorved man fikk 3-R 2 -6-R 1- 7 - sulfamoyl - 2,1,4-benzoazadithian-d , 1-di-thian-1 , 1-dioxydforbindelser identifisert i tabell I.

Claims (3)

1. Fremgangsmåte ved fremstilling av terapeutisk virksomme benzoazadithianer av formelen: og fysiologisk godtagbare salter derav, hvor: R* er hydrogen,halogen, trihalogenmethyl, lavere alkyl, lavere alkoxy, nitro eller amino, R <2> og R 3, som kan være like eller forskjellige, er hydrogen, halogen-lavere alkyl, lavere alkyl, fenyl-lavere alkyl, lavere alkoxyfenyl, eller sammen med ringcarbonatomet til hvilket de er bundet, kan R 2 og R 3 danne en eventuelt lavere alkylsubstituert cycloalkylgruppe med 5 eller 6 ringcarbonatomer, R <4> og R <5>, som kan være like eller forskjellige, er hydrogen eller lavere alkyl, karakterisert ved at en 2, 4-disulfamoylmercaptobenzen-forbindelse av formelen: hvor R 1, R 4 og R <5>er som ovenfor angitt, omsettes med et aldehyd eller keton av formelen: eller reaktive funksjonelle derivater derav, hvor R 2 og R 3 er som ovenfor angitt, og når R* er nitro, reduseres denne gruppe eventuelt til amino, og at den dannede forbindelse eventuelt overføres til et salt på i og for seg kjent måte.
2. Fremgangsmåte ifølge krav 1 ved fremstilling av 3-klormethyl - 6 - klor - 7 - sulfamoyl-2, 1, 4-benzoazadithian -1, 1 -dioxyd, karakterisert ved at 5-klor-2,4-disulfamoylmercaptobenzen omsettes med kloracetaldehyd.
3. Fremgangsmåte ifølge krav 1 ved fremstilling av 6-klor-7-sulfamoyl-2, 1, 4-benzoazadithian-1, 1 -dioxyd, karakterisert ved at 5-klor-2, 4-disulfamoylmercaptobenzen omsettes med formaldehyd.
NO820350A 1981-02-06 1982-02-05 Fortykkende blanding, samt anvendelse av den. NO159677C (no)

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NO159677C (no) 1989-01-25
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US4432881A (en) 1984-02-21
DE3276437D1 (en) 1987-07-02
JPS57155280A (en) 1982-09-25
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IN156183B (no) 1985-06-01
MX159228A (es) 1989-05-08
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NO820350L (no) 1982-08-09
EP0057875B1 (en) 1987-05-27
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