FI111715B - Förfarande för framställning av terapeutiskt användbara cykloalkylsubstituerade glutaramidföreningar - Google Patents

Förfarande för framställning av terapeutiskt användbara cykloalkylsubstituerade glutaramidföreningar Download PDF

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FI111715B
FI111715B FI894158A FI894158A FI111715B FI 111715 B FI111715 B FI 111715B FI 894158 A FI894158 A FI 894158A FI 894158 A FI894158 A FI 894158A FI 111715 B FI111715 B FI 111715B
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heterocyclyl
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Keith James
John Christopher Danilewicz
Ryszard Jurek Kobylecki
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Pfizer
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Claims (5)

1. Förfarande för framställning av nya terapeutiskt användbara cykloalkylsubstituerade glutaramidföreningar 5 med formeln I och farmaceutiskt godtagbara salter därav, <y s XC0NH-CH R02c ^co2r4 i vilken forme1 15. kompletterar en 5- eller 6-ledad mättad karbok- syklisk ring; * R1 är H; R och R4 är bäda självständigt H, (cyg) -alkyl, (C3_7)-cykloalkyl, bensyl eller en alternativ biolabil 20 esterbildande grupp; Y är en metylengrupp; V. R2 är H, fenyl, R6CONR5- eller R7NR5CO-; väri R5 är H, (Ci.6) -alkyl eller fenyl-(cy6) -alkyl; » * II ', R6 är en grupp med formeln 25 r9 v: R10_c V· έ» : y 30 väri R9 är H, OH, (cy 6) -alkyl, hydroxi - (cy6) -alkyl, fenyl- (cy6)-alkyl, fenyl-(Cy6) -alkylamino, R12CONH-, R12S02NH- eller (R13)2N-; R10 och R11 är bäda självständigt H eller (cyj-alkyl; eller R10 är H och R11 är amino- (cy6) -alkyl, imidazo-35 lylmetyl, fenyl, 4-hydroxi fenyl, f enyl - (C1_6) -alkyl, fenyl- 105 111715 (Ci_6)-alkoxi-(Ci_6)-alkyl, hydroxi-(C^J -alkyl ellermetyl-tio-(Ci.g)-alkyl; eller R10 och R11 bildar tillsammans med den kolatom, till vilken de är bundna, en 3 - β-ledad kar-bocyklisk ring eller en pyrrolidin- eller piperidinring, 5 sora kan vara substituerad med amino eller bensoyl; R12 är (Ci.g)-alkyl, (C3_7)-cykloalkyl, fenyl, halo- genfenyl, fenyl-(CVg)-alkyl, furyl eller pyridyl; envart R13 är självständigt H, (C^g) -alkyl eller fenyl-(Cx.6) -alkyl;
10 R7 är en grupp med formeln R14 R1?— C 15 väri R10 är H; R11 är amino- (CVg) -alkyl eller imidazolylme-tyl; och R14 är H eller hydroxi-(Οχ_6)-alkyl; och R3 är en grupp med formeln -kX” ;'ϊ Λ20 ! väri R16 är H, 4-OH, 4-(CVg-alkoxi) , 4-[ (C^g-alkoxi) karbo- . 25 nyloxi] , 4-[ (C3_v-cykloalkoxi) karbonyloxi] eller 3-(C^4- I I t *;;; alkyl) S02NH-; och R20 är H, (C1.4) -alkyl, (C2_6)-alkanoyl el- * i · '·’ ’ ler halogen; eller R3 är en grupp med formeln ; - - “90 kännetecknat därav, att man frän en förening 106 111715 2' /-‘S-'1
5 E \ (c) f (V) CHCH2 ’ CONH-CH 17 / \ R °2C C02R18 10 väri A och R1 betecknar samma som ovan, R21 och R3' beteck- nar samma som R2 och R3, varvid i dessa närvarande reaktiva grupper eventuellt är skyddade, och R17 och R18 betecknar samma som R och R4, förutom väte, eller de är konventionel-la karboxylsyraskyddsgrupper, avlägsnar den ena eller var-15 dera av de esterbildande och skyddande grupperna R17 och R18, eller dä bade R17 och R18 betecknar en skyddsgrupp, avlägsnar man bäda skyddsgrupperna, och avlägsnar eventuella övriga skyddsgrupper i R2' och R3'; och, om sa önskas, om-vandlar man den erhällna produkten till ett farmaceutiskt 20 godtagbart salt.
2. Förfarande enligt patentkrav 1, k ä n n e -t e c k n a t därav, att man framställer N-[1-(2 (S)-kar- » · ; boxi-3- (S) -lysylaminopropyl) -1-cyklopentankarbonyl] - (S) - * ♦ tyrosin,
25 N-{1-[2 (S)-karboxi-3-(N2-metansulfonyl-(S)-lysylami- * » · no)propyl]-1-cyklopentankarbonyl}-(S)-tyrosin, eller * N-{l-[2-(S) -karboxi-3-(N2-fenylsulfonyl-(S) -lysyla- mino) propyl] - 1-cyklopentankarbonyl}-(S)-tyrosin, eller ett farmaceutiskt godtagbart salt eller biolabilt esterderivat I ' 3 0 av dessa. I I
FI894158A 1988-09-05 1989-09-04 Förfarande för framställning av terapeutiskt användbara cykloalkylsubstituerade glutaramidföreningar FI111715B (sv)

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