FI91396B - Förfarande för framställning av terapeutiskt användbara 3,5-disubstituerade pyrokatekolderivat - Google Patents

Förfarande för framställning av terapeutiskt användbara 3,5-disubstituerade pyrokatekolderivat Download PDF

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FI91396B
FI91396B FI871041A FI871041A FI91396B FI 91396 B FI91396 B FI 91396B FI 871041 A FI871041 A FI 871041A FI 871041 A FI871041 A FI 871041A FI 91396 B FI91396 B FI 91396B
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hydroxy
methylene chloride
lower alkyl
dihydroxy
group
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FI871041A (sv
FI91396C (sv
FI871041A0 (sv
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Karl Bernauer
Janos Borgulya
Hans Bruderer
Prada Mos Da
Gerhard Zuercher
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Hoffmann La Roche
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Claims (10)

1. Förfarande för framställning av terapeutiskt användbara föreningar med den allmänna formeln (Ib) 5 ?a HOx./\ J il D , (Ib) V*“Rc HO N·^ Rb 10 väri Ra är nitro eller cyan, Rb är väte eller halogen, Rc' är nitro, cyan eller en grupp -(A) —(Q) -R11 eller 21. n ra -(A) -Q-R, A är vmylen, som kan vara substituerad med n 11 lägre alkyl, n är o eller 1, m är 0 eller 1, R är en 31 21 grupp -COR , aryl eller heteroaryl, R är en lägre al- 15 kylgrupp, som är osubstituerad eller har en substituent ur gruppen hydroxi, halogen, amino, lägre alkoxikarbony1, aryl, arylaminokarbonyl, arylkarbonyl och lägre alkanoyl-oxi, R är hydroxi, amino eller en genom en syreatom eller imino- eller lägre alkyl-iminogrupp bunden lägre al-20 kylgrupp, som är osubstituerad eller monosubstituerad med amino eller di(lägre alkyl)amino, Q är en grupp -CO- el- 4 4 ler >C=N-(Z)p-R ' Z är en syreatom, p är 1 och R är en lägre alkylgrupp, varvid Ra är cyan, dä Rc' är cyan eller nitro, och R är annat än hydroxi, dä m är 0, och varvid 25 aryl betecknar en fenyl- eller naftylgrupp, som är osubstituerad eller substituerad med en eller tvä substituen-ter ur gruppen halogen, trifluormetyl, amino, lägre alkyl, hydroxi och cyan, och heteroaryl betecknar en genom en kolatom bunden heterocyklisk grupp ur gruppen pyridyl, 30 pyrazinyl, triazinyl, tiadiazinyl, tiazolyl, oxadiazolyl, pyrazolyl, tetrazolyl, imidazolyl, tienyl, kinolinyl, isokinolinyl, dihydroisokinolinyl, bensoxazinyl, kinoxa-linyl, bensopyranyl, bensimidazoly1, indolyl, imidazoti-azolyl, imidazotiadiazolyl, imidazopyridyl, bensotiazi-35 nyl, bensokinoxalinyl och imidazobensotiazolyl, och vil- 102 ken heterocyklisk grupp är osubstituerad eller substitue-rad med en, tvä eller tre substituenter ur gruppen halogen, trifluormetyl, nitro, karboxi, amino, arylamino, lägre alkyl, lägre alkoxi, hydroxi, oxo, merkapto, C8_1Q-5 bicykloalkylamino, cyan, aryl, aryl(lägre alkyl), aryl-(lägre alkyl)amino, heteroaryl och heteroarylamino och varvid attributet lägre anger grupper innehillande högst sju kolatomer, samt under fysiologiska förhällanden hyd-rolyserbara (lägre alkanoyl)estrar och (lägre alkyl)etrar 10 och farmaceutiskt godtagbara salter därav, k ä n n e -t e c k n a t därav, att a) man avspjälkar den (de) lägre alkyletergruppen (-grupperna) av en förening med den allmänna formeIn (II) ?a
15 R0\ Λχ?-·»' (II> R'° · Rb väri den ena av symbolerna R och R' betecknar lägre alkyl 20 och den andra väte eller lägre alkyl och Ra, Rb och Rc' betecknar samma som ovan, eller b) en förening med den allmänna formeln HCV\ 1 25. j‘- (A) n-CO-CH2-X (Ib ) H0 · Rb väri X betecknar en avgiende grupp och Ra, Rb, A och n betecknar samma som ovan, omsätts med en tioamid, tio-30 urea, tiokarboxylsyrahydrazid, tiosemikarbazid, amidin, guanidin, amidrazon, aminoguanidin, cyklisk amidin, 1,2-diamin, 1,2-aminotiol eller 1,2-aminoalkohol och om sä önskas, dehydreras den erhälinä cyklokondensationsproduk-ten, eller 103 91396 c) en förening med den allmänna formeln f* «<\ Λ • · 5 unA A(A) n-c°-C00R" 2 H0 * Rb (Ib2) väri R" är lägre alkyl och Ra, Rb, A och n betecknar 10 samma som ovan, omsätts med en 1,2-diamin, 1,2-aminotiol, 1,2-aminoalkohol, semikarbazid, tiosemikarbazid, amid-razon eller aminoguanidin och om sä önskas, dehydreras den erhälinä cyklokondensationsprodukten, eller d) en förening med den ovan angivna formeln (Ib1) 15 omsätts med en β-aminokarbonylförening, eller e) karboxaldehydgruppen (-grupperna) i en förening med den allmänna formeln cho 9n 9ho H0\
20 A\i-Rc"' /\v'CH0 /U'-® H0 Ab H0 Ab eller H0 Ab (III) (Ia2) (IV) . . 12 van Rc''' är nitro, cyan eller en grupp -(A) -R och 12 31 n R är en grupp -COR , aryl eller heteroaryl och Ra, Rb, 31
25 A, n och R betecknar samma som ovan, eller i ett di-0-(lägre alkanoyl)derivat därav omvandlas tili cyangrupp (-grupper), eller f) ett di-0-(lägre alkanoyl)derivat av en karbox-ylsyra med den allmänna formeln
30 Ra "°\/\ H0X Av--(A)n-COOH i li „ H0/ ''Ab eller n COOH Rb 35 (Ia3) (Ib3) 104 väri Ra, Rb, Ά och n betecknar samna son ovan, i närvaro av ett kondenseringsämne eller ett reaktivt derivat av ett di-0-(lägre alkanoyl)derivat av en karboxylsyra med 3 3 tornein la eller Ib onsätts ned en förening ned den al-5 lmänna tornein HO-R5 (V) eller HNR6R7 (VI) 5 väri R är en lägre alkylgrupp son är osubstituerad eller 10 nonosubstituerad ned anino eller di(lägre alkyl)anino, R6 7 är väte eller lägre alkyl och R är väte eller en lägre alkylgrupp son är osubstituerad eller nonosubstituerad ned anino eller di(lägre alkyl)anino, eller g) en törening ned ovan angivna tornein Ib eller 15 en förening ned den allnänna tornein Ra o8q · V\ , !xV'!-Rc· (Ib4) "-\b 20 Q väri R är lägre alkanoyl och Ra, Rb och Rc' betecknar sanna son ovan, hydrolyseras, eller h) en förening ned den allnänna tornein
25 H0\ /X - i jj rOR«. (Ib5) x C0R H0 · Rb väri Ra och Rb betecknar sanna son ovan och R"' är väte 30 eller lägre alkyl, eller ett di-0-(lägre alkanoyl)derivat därav onsätts i närvaro av en sekundär anin ned en förening ned den allnänna tornein CH3CO-R23 (VII) 35 91396 105 van R23 gr en ^ggre alkylgrupp som är osubstituerad el-ler som har en substituent ur gruppen hydroxi, halogen, amino, lägre alkoxikarbonyl, aryl, arylaminokarbonyl, arylkarbonyl och lägre alkanoyloxi, eller 5 i) en förening med den allmänna formeIn HO. N./ (Ib6) Λ v"-(A)n-C0-CH2-C00R" H0 * Rh
10 Rb väri Ra, Rb, Ά, n och R'' betecknar samma som ovan, om-sätts med en hydrazin eller amidin, eller j) en förening med ovan angivna formeln Ib, väri m 15 betecknar talet 1 och Q gruppen -CO-, omsätts med en förening med den allmänna formeln h2N-(z)p-r4 (VIII) 4 o 20 väri Z, p och R betecknar samma som ovan, och, om sa önskas, k) omvandlas en förening med den ovan angivna formeln Ib till en under fysiologiska förhällanden hydro-lyserbar (lägre alkanoyl)ester eller (lägre alkyl)eter 25 eller ett farmaceutiskt godtagbart salt därav.
2. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att Rb är i p-ställning till Ra.
3. Förfarande enligt patentkrav 1 eller 2, k ä n-netecknat därav, att Ra är nitro. 30
4. Förfarande enligt nägot av patentkraven 1-3, kännetecknat därav, att Rb är väte, klor eller fluor.
5. Förfarande enligt patentkrav 4, kännetecknat därav, att Rb är väte. 35
6. Förfarande enligt nägot av patentkraven 1-5, kännetecknat därav, att Rc' är en grupp 106 -CO-R11 och R11 är en fenylgrupp, som är osubstituerad eller substituerad med en eller tv& substituenter ur gruppen halogen, trifluormetyl, amino, lägre alkyl, hyd-roxi och cyan, eller en genom en kolatom bunden grupp ur 5 gruppen pyridyl, pyrazinyl, triazinyl, pyrazolyl, tetra-zolyl och imidazolyl, vilken heterocyklisk grupp är osubstituerad eller substituerad med en, tvä eller tre substituenter ur gruppen halogen, trifluormetyl, nitro, karboxi, amino, arylamino, lägre alkyl, lägre alkoxi, 10 hydroxi, oxo, merkapto, c8_1()-bicykloalkylamino, cyan, aryl, aryl(lägre alkyl), aryl(lägre alkyl)amino, heteroaryl och heteroarylamino.
7. Förfarande enligt patentkrav 6, känne- t e c k n a t därav, att R11 är en fenylgrupp som even-15 tuellt mono- eller disubstituerats med halogen, trifluor-metyl, cyan, hydroxi och/eller lägre alkyl, eller en py-ridylgrupp.
8. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer 3,4-dihydroxi-20 5-nitrobensofenon.
9. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att man framställer 2'-fluor-3,4-dihydroxi-5-nitrobensofenon.
10. Förfarande enligt patentkrav 1, känne- 25 tecknat därav, att man framställer 3,4-dihydroxi- 5-nitrofenyl-4-pyridylketon.
FI871041A 1986-03-11 1987-03-10 Förfarande för framställning av terapeutiskt användbara 3,5-disubstituerade pyrokatekolderivat FI91396C (sv)

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FI91396C (sv) 1994-06-27
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