FI113169B - Förfarande för framställning av nya terapeutiskt användbara pyrazolderivat och utgångsämne för förfarandet - Google Patents

Förfarande för framställning av nya terapeutiskt användbara pyrazolderivat och utgångsämne för förfarandet Download PDF

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FI113169B
FI113169B FI932891A FI932891A FI113169B FI 113169 B FI113169 B FI 113169B FI 932891 A FI932891 A FI 932891A FI 932891 A FI932891 A FI 932891A FI 113169 B FI113169 B FI 113169B
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hydrogen
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Christian Congy
Murielle Rinaldi
Serge Martinez
Pierre Casellas
Francis Barth
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Sanofi Synthelabo
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Claims (14)

1. I | * I » » * I 11316? 86
1. Förfarande för framställning av pyrazolderivat med formeln (I) eller salter därav, som har affinitet tili 5 kannabinoidreceptorer, R* X-CO-R W! S} i ÄA W5 'γ w3 *4 i vilken formel g2, g3 och g6 är väteatomer; g4 är klor eller brom, (C1-C3)alkyl, trifluormetyl eller fenyl; 10 och g5 är väte eller klor; w2, w3/ w5 och w6 var och en sj älvständigt är väte-eller kloatomer; w4 är väte, klor, (C1-C3) alkyl, (C1-C3)- i<; alkoxi eller nitro; R4 är väte eller (C1-C3) alkyl; , 15 X är en direkt bindning eller en grupp - (CH2) X-N (R3) -, där R3 är väte eller (Ci~C3) alkyl och x är 0 eller 1; och (i) dä X är en direkt bindning, är R -NR3R2, där Ri är väte, (Ci-C6)alkyl eller (C5-C7)-· cykloalkyl och R2 är (Ci-C3) alkyl; en icke-aromatisk (C3-C15)- 20 karbocyklisk radikal, som kan vara substituerad med hy- droxyl, 1-3 (Cx-Cs) alkylgrupper, (C1-C5) alkoxi eller halogen; di (C3-C3) alkylamino (Ci-C4) alkyl; (C3-Ci0) cyklo alkyl (Ci-C3) alkyl; fenyl, som kan vara substituerad med ‘ halogen eller (C1-C5) alkyl; f enyl (Ci-C3) alkyl; difenyl (Ci-
25 C3)alkyl; pyrrolidin-l-yl; piperid-l-yl; hexahydroazepin- ; · ; 1-yl; morfolin-4-yl, kinuklidyl; oxabicykloheptanyl; 1- : cykloheptanyl; l-bensylpiperid-4-yl; (Ci~C3)alkylpyrrol- yl (Ci-C3) alkyl; pyridyl (Ci~C3) alkyl; eller indolyl (Ci-C3) - 11316? 87 alkyl; eller Rx och R2 tillsammans med den kväveatom, till vilken de är bundna, bildar en pyrrolidyl-, piperidyl-eller morfolinylring; eller R5, där R5 är fenyl (C1-C3) alkyl, som är substi-5 tuerad med (Ci-C5) alkyl; eller (C5-C8) cykloalkyl (Ci-C3) -alkyl; (ii) da X är en grupp -CH2-N(R3)-, är R (C5-Ci0)-cykloalkyl; indolyl, som kan vara substituerad med (Ci-C3)alkoxi; antracenyl; fenyl, som är substituerad med 10 halogen; (C5-C7) cykloalkylamino; eller fenylamino, som kan vara substituerad med en eller tvä halogener, (C1-C3)alkyl eller (C1-C3) alkoxi ; (iii) dä X är en grupp -N(R3), är R indolyl; benzyl, som i fenylringen är substituerad med halogen; 15 (C5-C10) cykloalkyl; fenylamino, som är substituerad med halogen; eller (C5-Ci0) cykloalkylamino, kännetecknat av, att en pyrazol-3-karboxylsyraklorid, som har formeln: R, COCI :: ‘ ft-vV' &> I 20 behandlas med (a) en amin, som har formeln HNRiRs, varvid erhälls en amid, som har formeln: 88 113169 η Λ W Ri <Ia) eller (b) en primär amin, som har formeln R3NH2/ varvid erhälls en mellanproduktsamid, som har formeln (V), R„ CO-NHRj (v> J w‘i i WS y W, ·: w4 5 , vilken reduceras med en metallhydrid, varvid er- \ hälls en amin, som har formeln (VI) R< CHj-NHRj .T: / n' (/_ I (vi) w< l :*. ; vilken omvandlas tili en amid eller en ureafören- 10 ing med formeln (Ib) eller (Ie), 89 113169 R, R4 CH2-N-C-Rj CH2-N-C-NH-R; 0 ‘vvO 1. ar^yJ-& l.Wj J wi"| eller ^ w< | »/γΝ " %. W, (lb) (Ic) genom att bringa denna förening att reagera med en syraklorid, som har formeln R2C0C1, eller med ett iso-cyanat, som har formeln R2-N=C=0, 5 eller (c) ett difenylfosforylazidderivat i ett basiskt medium och därefter med en syra i ett alkoholhaltigt medium, varvid erhälls en mellanproduktsamin med formeln (VII), R* NHj V: ^ <VII) % "‘XX .: ws Ύ w3 : % 10 * : vilken bringas att reagera med en syraklorid, som har formeln R2C0C1, eller med ett isocyanat, som har formeln R2N=C=0, varvid erhälls en amid eller en ureaförening med formeln (Id) eller (Ie), 5 » 90 11316? K, «. R. VJ-C-R, R4k N-C-NH-R, k \_/ Il z b \_/ Il / » 0 lrVv\ n ° w2 ^ r^vL/"’ gj li tai 6 W<TT‘ «4 % (Id) (Ie) där R3 är väte, och för framställning av sädana föreningar med formeln (Id) eller (Ie) , där R3 är annat än väte, omvandlas en 5 primär amin med formeln (VII) tili en sekundär amin med formeln (Vllb), R4 NHR'j f lf^ (vi ib) W4 • j där R'3 är (Ci-C2) alkyl, vilken förening sedan : bringas att reagera med en syraklorid, som har formeln f. 10 R2COCl, eller med ett isocyanat, som har formeln R2-N=C=0, varvid erhälls en amid eller en ureaförening med formeln (Id) eller (Ie), där R3 är annat än väte, eller (d) en organomanganförening R5MnXi, där Xi är halogen, varvid erhälls ett derivat med formeln (If), « 91 113169 O II R< C-R, Γ af) % w, w3 *4 och om sa önskas, omvandlas det sä erhällna deri-vatet tili ett sait.
2. Förfarande enligt patentkrav 1, kannet eck-5 n a t av, att man framställer ett derivat med formeln (Ia)
0 R Il / ' R\ /C”N\ «r\J? _/ \ Rj J 11^ (Ia) ‘Λτ-vV ·, ‘ -?Y^, W4 eller ett sait därav, ! i vilken formel Rx är väte eller (Ci-C6) alkyl och
10 R2 är en icke-aromatisk (C3-Ci5)-karbocyklisk radikal, 1-pyrrolidinyl, 1-piperidinyl, 1-hexahydroazepinyl eller • ‘ 4-morfolinyl.
3. Föfarande enligt patentkrav 1, känneteck- i n a t av, att man framställer ett derivat med formeln (i) t » 92 113169 O II X-C-R F c\^\J I (i) V Cl eller ett sait därav.
4. Förfarande enligt patentkrav 3, känneteck-n a t av, att man framställer ett derivat med formeln 5 (i) , där R4 är väte eller en metylgrupp, eller ett sait därav.
5. Förfarande enligt patentkrav 4, känneteck- n a t av, att man framställer ett derivat med formeln (i), där X är en direkt bindning, eller ett derivat därav. 10 6. Förfarande enligt patentkrav 5, k ä n n e- t e c k n a t av, att man framställer ett derivat med formeln (i) , där R är -NRiR2, där Rx är väte eller metyl i och R2 är en icke-aromatisk (C3-Ci5) karbocyklisk radikal, 1-pyrrolidinyl, 1-piperidinyl, 1-hexahydroazepinyl eller 15 4-morfolinyl, eller ett sait därav.
7. Förfarande enligt patentkrav 3, känneteck-·, n a t av, att man framställer ett derivat med formeln .! (i) , där R4 är väte eller metyl och X är - (CH2) X-N (R3) -, där x är noll eller ett och R3 är väte eller metyl, och 20 (i) dä X är -CH2-N(R3)-, är R (C5-C7) cyklo- alkylamino eller fenylamino, som eventuellt är substi-tuerad med en eller tvä halogener, (Ci-C3) alkyl eller 1 · (Ci-C3) alkoxi ; (ii) dä X är -N(R3)-, är R fenylamino, som är sub-25 stituerad med halogen; eller (C5-Ci0) cykloalkylamino, eller ett sait därav. » 93 113169
8. Förfarande enligt patentkrav 1, känneteck-n a t av, att man framställer ett derivat med formeln (ii) , * X-C-R αΛ^ X Y W4 5 eller ett sait därav, där R4 är väte, w4 är en metyl- eller metoxigrupp, X är en direkt bindning eller -CH=N(R3)-, där R3 är väte eller (C!-C3) alkyl, och (i) da X är en direkt bindning, är R -NRiR2, där Ri 10 är väte eller (Οχ-Οβ) alkyl och R2 är (Ci-C6) alkyl; en icke-aromatisk (C5-Ci0) -karbocyklisk radikal, som kan vara substituerad med (Ci-C5) alkyl; indolyl (Cx-C3) alkyl; eller . Ri och R2 tillsammans med den kolatom, tili vilken de är bundna, bildar pyrrolidinyl; 15 (ii) da X är -CH2-N(R3)-, är R (C5-C7) cykloalkyl, indolyl eller fenylamino, som är substituerad med halogen, •j 9. Förfarande enligt patentkrav 8, k ä n n e- ' tecknat av, att man framställer ett derivat med for- : meln (ii) , där X är en direkt bindninng och R är en grupp 2 0 -NR]R2, där Rx är väte eller metyl och R2 är en icke-aromatisk (C5-Ci0) karbocyklisk radikal, » eller ett sait därav.
10. Förfarande enligt patentkrav 8, k ä n n e-' tecknat av, att man framställer ett derivat med • 25 formeln (ii) , där X är -CH2-N(R3)-, där R3 är väte eller . metyl, eller ett sait därav.
11. Förfarande enligt patentkrav 1, känne- tecknat av, att man framställer ett derivat med 94 113169 formeln (I) , där R4 är väte, X är en direkt bindning och R är -NRiR2, där Ri är väte eller (Ci-C6) alkyl och R2 är 2-eller 3 - indolyl (Ci-C3) alkyl, eller ett sait därav. 5 12. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer ett derivat med formeln (iii) X-C-R SSL (iii) W4 eller ett sait därav, 10 där X är en direkt bindning, R är -NRiR2, där Ri är väte eller (Ci-C6) alkyl och R2 är en 2- eller 3-indolyl-(Ci-C3) alkylgrupp, och antingen w2 är väte och w4 är metyl ; eller metoxi eller w2 och w4 är kloratomer. '2 13. Förfarande enligt patentkrav 1, känne- 15 tecknat av, att man framställer ett derivat med ; formeln (iv) k X-C-R ^ ΓΛ 0 ci : eller ett sait därav, 95 113169 där g4 är en bromatom eller en metyl- eller tri-fluormetylgrupp, X är en direkt bindning och R är -NRiR2, där Rx är väte eller (Ci-C6) alkyl och R2 är en icke-aromatisk (C5-Ci0)-karbocyklisk radikal, sora eventuellt är 5 substituerad med en eller tvä (Ci-C5) alkylgrupper eller (Ci-C5) alkoxi ; eller f enyl (C1-C3) alkyl.
14. Utgängsämne för ett förfarande enligt patent-krav 1, kännetecknat därav, att den har for-meln (II) R, COjR Cl n (ID V Cl 10 där R4 är (C2.-C3) alkyl och R är H eller (C2.-C3) - ,: alkyl. s » • I t
FI932891A 1992-06-23 1993-06-22 Förfarande för framställning av nya terapeutiskt användbara pyrazolderivat och utgångsämne för förfarandet FI113169B (sv)

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HU9301851D0 (en) 1993-09-28
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