HRP20120290T1 - NOVI DERIVATI (PREMOŠTENI PIPERAZINIL)-1-ALKANONA I NJIHOVA UPOTREBA KAO INHIBITORA p75 - Google Patents

NOVI DERIVATI (PREMOŠTENI PIPERAZINIL)-1-ALKANONA I NJIHOVA UPOTREBA KAO INHIBITORA p75 Download PDF

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HRP20120290T1
HRP20120290T1 HR20120290T HRP20120290T HRP20120290T1 HR P20120290 T1 HRP20120290 T1 HR P20120290T1 HR 20120290 T HR20120290 T HR 20120290T HR P20120290 T HRP20120290 T HR P20120290T HR P20120290 T1 HRP20120290 T1 HR P20120290T1
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pyridin
trifluoromethyl
diazabicyclo
dihydro
connection
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Baroni Marco
Bono Fran�oise
Delbary-Gossart Sandrine
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Sanofi
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Abstract

Spoj formule (I): naznačen time što:- m predstavlja 0 ili 1;- A predstavlja: ,a B predstavlja atom vodika iliA predstavlja atom vodika, a B predstavlja: ;- W- je heterocikl s dušikom, kojeg se bira između: - 1-3 predstavlja 1, 2 ili 3;- n predstavlja 1 ili 2;- R1 predstavlja atom halogena, (C1-C4)alkilnu skupinu, trifluormetilni radikal, (C1-C4)alkoksi skupinu ili trifluormetoksi radikal;- R2 predstavlja atom vodika, atom halogena, (C1-C4)alkilnu skupinu, trifluormetilni radikal, (C1-C4)alkoksi skupinu, trifluormetoksi radikal, skupinu COOR ili skupinu CONH2;- R5 predstavlja skupinu formule: iligdje R3 i R4, smješteni na bilo kojem od dostupnih položaja, neovisno predstavljaju atom vodika, atom halogena, (C1-C4)alkilnu skupinu, (C1-C4)alkoksi skupinu, trifluormetilni radikal, trifluormetoksi radikal, cijano radikal, skupinu COOH, COOalkilnu skupinu, skupinu CONH2, skupinu CONR6R7 ili skupinu NHCOR;- R, R6 i R7 predstavljaju (C1-C6)alkilnu skupinu; u obliku baze ili adicijske soli s kiselinom. Patent sadrži još 15 patentnih zahtjeva.

Claims (16)

1. Spoj formule (I): [image] naznačen time što: – m predstavlja 0 ili 1; – A predstavlja: [image] , a B predstavlja atom vodika ili A predstavlja atom vodika, a B predstavlja: [image] ; – W- je heterocikl s dušikom, kojeg se bira između: [image] – 1-3 predstavlja 1, 2 ili 3; – n predstavlja 1 ili 2; – R1 predstavlja atom halogena, (C1-C4)alkilnu skupinu, trifluormetilni radikal, (C1-C4)alkoksi skupinu ili trifluormetoksi radikal; – R2 predstavlja atom vodika, atom halogena, (C1-C4)alkilnu skupinu, trifluormetilni radikal, (C1-C4)alkoksi skupinu, trifluormetoksi radikal, skupinu COOR ili skupinu CONH2; – R5 predstavlja skupinu formule: [image] ili [image] gdje R3 i R4, smješteni na bilo kojem od dostupnih položaja, neovisno predstavljaju atom vodika, atom halogena, (C1-C4)alkilnu skupinu, (C1-C4)alkoksi skupinu, trifluormetilni radikal, trifluormetoksi radikal, cijano radikal, skupinu COOH, COOalkilnu skupinu, skupinu CONH2, skupinu CONR6R7 ili skupinu NHCOR; – R, R6 i R7 predstavljaju (C1-C6)alkilnu skupinu; u obliku baze ili adicijske soli s kiselinom.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R2 je atom vodika, trifluormetilni radikal, skupina COOR ili skupina CONH2; u obliku baze ili adicijske soli s kiselinom.
3. Spoj u skladu s patentnim zahtjevom 1 ili 2, naznačen time što R5 predstavlja skupinu formule: [image] gdje R3 i R4 neovisno predstavljaju atom vodika, atom halogena, trifluormetilni radikal, CONH2 radikal, COOH radikal ili NHCOCH3 radikal; u obliku baze ili adicijske soli s kiselinom.
4. Spoj u skladu s patentnim zahtjevom 1, naznačen time što: – m predstavlja 1; – A predstavlja: [image] a B predstavlja atom vodika; – W- je heterocikl s dušikom, kojeg se bira između: [image] – n predstavlja 1 ili 2; – R1 predstavlja atom halogena, (C1-C4)alkilnu skupinu, trifluormetilni radikal, (C1-C4)alkoksi skupinu ili trifluormetoksi radikal; – R2 predstavlja atom vodika, atom halogena, (C1-C4)alkilnu skupinu, trifluormetilni radikal, (C1-C4)alkoksi skupinu ili trifluormetoksi radikal; – R5 predstavlja skupinu formule: [image] ili [image] gdje R3 i R4, smješteni na bilo kojem od dostupnih položaja, neovisno predstavljaju atom vodika, atom halogena, (C1-C4)alkilnu skupinu, (C1-C4)alkoksi skupinu, trifluormetilni radikal, trifluormetoksi radikal, cijano radikal, skupinu COOH ili COOalkilnu skupinu; u obliku baze ili adicijske soli s kiselinom.
5. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što W je skupina čiju se formulu bira između: [image] u obliku baze ili adicijske soli s kiselinom.
6. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što n = 1; u obliku baze ili adicijske soli s kiselinom.
7. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što R1 je atom halogena ili trifluormetilni radikal; u obliku baze ili adicijske soli s kiselinom.
8. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što R2 je atom vodika ili trifluormetilni radikal; u obliku baze ili adicijske soli s kiselinom.
9. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što R5 predstavlja skupinu formule: [image] gdje R3 i R4 neovisno predstavljaju atom vodika, atom halogena ili trifluormetilni radikal; u obliku baze ili adicijske soli s kiselinom.
10. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što ga se bira između sljedećih spojeva: – Spoj br. 1: 1-[4-(3-(Trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(5-(trifluormetil)piridin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 2: 1-[4-(4-Klorfenil)-3,6-dihidro-2H-piridin-1-il]-2-(8-(pirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il)etanon; – Spoj br. 3: 2-(3-(Pirazin-2-il)-3,8-diazabiciklo[3.2.1]okt-8-il)-1-[4-(3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 4: 2-(8-(Pirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il)-1-[4-(3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 5: 1-[4-(3-(Trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[3-(5-(trifluormetil)piridin-2-il)-3,8-diazabiciklo[3.2.1]okt-8-il]etanon; – Spoj br. 6: 2-(8-(Piridin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il)-1-[4-(3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 7: 1-[4-(4-Klorfenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(5-(trifluormetil)piridin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 8: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(5-(trifluormetil)piridin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 9: 2-(8-(Kinolin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il)-1-[4-(3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 10: 1-[4-(4-Klorfenil)-3,6-dihidro-2H-piridin-1-il]-2-[3-(5-(trifluormetil)piridin-2-il)-3,8-diazabiciklo[3.2.1]okt-8-il]etanon; – Spoj br. 11: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(5-fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 12: 2-[8-(5-Bromopirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[4-(4-klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 13: 1-[4-(3-(Trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[5-(5-(trifluormetil)piridin-2-il)-2,5-diazabiciklo[2.2.1]hept-2-il]etanon; – Spoj br. 14: 1-[4-(4-Klorfenil)-3,6-dihidro-2H-piridin-1-il]-2-[5-(5-(trifluormetil)piridin-2-il)-2,5-diazabiciklo[2.2.1]hept-2-il]etanon; – Spoj br. 15: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[5-(5-(trifluormetil)piridin-2-il)-2,5-diazabiciklo[2.2.1]hept-2-il]etanon; – Spoj br. 16: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-(5-(piridin-2-il)-2,5-diazabiciklo[2.2.1]hept-2-il)etanon; – Spoj br. 17: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[5-(5-fluorpirimidin-2-il)-2,5-diazabiciklo[2.2.1]hept-2-il]etanon; – Spoj br. 18: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[9-(5-(trifluormetil)piridin-2-il)-3,9-diazabiciklo[3.3.1]non-3-il]etanon; – Spoj br. 19: 2-[8-(5-Fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[4-(4-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 20: 1-[4-(3-Klorfenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(5-fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 21: 2-[8-(5-Fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[4-(3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 22: 1-[4-(4-Klorfenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(5-fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 23: 1-[4-(3,5-Bis(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(5-fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 24: 2-[8-(5-Fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-(4-(m-tolil)-3,6-dihidro-2H-piridin-1-il)etanon; – Spoj br. 25: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(pirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 26: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[3-(5-fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-8-il]etanon; – Spoj br. 27: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-(8-(piridin-3-il)-3,8-diazabiciklo[3.2.1]okt-3-il)etanon; – Spoj br. 28: Metilni ester 6-(3-{2-[4-(4-klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-oksoetil}-3,8-diazabiciklo[3.2.1]okt-8-il)nikotinske kiseline; – Spoj br. 29: 6-(3-{2-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-oksoetil}-3,8-diazabiciklo[3.2.1]okt-8-il)nikotinska kiselina; – Spoj br. 30: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(6-(trifluormetil)piridin-3-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 31: 2-[8-(5-Klorpiridin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[4-(4-klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 32: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-(8-(kinolin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il)etanon; – Spoj br. 33: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(5-fluorpiridin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 34: 2-[8-(6-Klorpiridin-3-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[4-(4-klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 35: 1-[4-(3-(Trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(3-(trifluormetil)piridin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 36: Etilni ester 6-(3-{2-[4-(4-klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-oksoetil}-3,8-diazabiciklo[3.2.1]okt-8-il)nikotinske kiseline; – Spoj br. 37: 2-(8-(Pirazin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il)-1-[4-(3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 38: 2-(8-(Pirimidin-4-il)-3,8-diazabiciklo[3.2.1]okt-3-il)-1-[4-(3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 39: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-(8-(pirazin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il)etanon; – Spoj br. 40: 2-(8-(Pirazin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il)-1-(4-(m-tolil)-3,6-dihidro-2H-piridin-1-il)etanon; – Spoj br. 41: Metilni ester 2-(3-{2-[4-(4-klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-oksoetil}-3,8-diazabiciklo[3.2.1]okt-8-il)pirimidine-5-karboksilne kiseline; – Spoj br. 42: 2-(3-{2-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-oksoetil}-3,8-diazabiciklo[3.2.1]okt-8-il)pirimidine-5-karboksilna kiselina; – Spoj br. 43: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-3-[8-(5-fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]propan-1-on; – Spoj br. 44: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[5-(5-fluorpirimidin-2-il)-2,5-diazabiciklo[2.2.2]okt-2-il]etanon; – Spoj br. 45: 2-[8-(5-fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[4-(3-metoksifenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 46: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[5-(6-(trifluormetil)piridazin-3-il)-2,5-diazabiciklo[2.2.1]hept-2-il]etanon; – Spoj br. 47: 2-[8-(5-Fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[3-(3-(trifluormetil)-4-klorfenil)-2,5-dihidropirol-1-il]etanon; – Spoj br. 48: 6-(3-{2-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-oksoetil}-3,8-diazabiciklo[3.2.1]okt-8-il)nikotinamid; – Spoj br. 49: 2-[8-(5-Fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[4-(2,3-diklorfenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 50: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[8-(6-fluorpiridin-3-il)-3,8-diazabiciklo[3.2.1]okt-3-il]etanon; – Spoj br. 51: 2-[8-(5-Fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[5-(3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 52: 2-[8-(5-Fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[3-(3-(trifluormetil)fenil)-2,5-dihidropirol-1-il]etanon; – Spoj br. 53: Metilni ester 3-(1-{2-[8-(5-fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]acetil}-1,2,5,6-tetrahidropiridin-3-il)benzojeve kiseline; – Spoj br. 54: 2-[8-(5-Fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[5-(2-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 55: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-(8-(pirimidin-5-il)-3,8-diazabiciklo[3.2.1]okt-3-il)etanon; – Spoj br. 56: 2-[8-(5-Fluorpirimidin-2-il)-3,8-diazabiciklo[3.2.1]okt-3-il]-1-[4-(3-(trifluormetoksi)fenil)-3,6-dihidro-2H-piridin-1-il]etanon; – Spoj br. 57: 1-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-[5-(6-(trifluormetil)piridazin-3-il)-2,5-diazabiciklo[2.2.2]okt-2-il]etanon; – Spoj br. 58: N-[6-(3-{2-[4-(4-Klor-3-(trifluormetil)fenil)-3,6-dihidro-2H-piridin-1-il]-2-oksoetil}-3,8-diazabiciklo[3.2.1]okt-8-il)piridin-3-il]acetamid; – Spoj br. 59: 2-(8-(Kinolin-3-il)-3,8-diazabiciklo[3.2.1]okt-3-il)-1-[4-(3-trifluormetil-4-klorfenil)-3,6-dihidro-2H-piridin-1-il]etanon; u obliku baze ili adicijske soli s kiselinom.
11. Postupak dobivanja spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 10, naznačen time što spoj formule (II): [image] , gdje A, B, m i n su definirani u skladu s bilo kojim od patentnih zahtjeva 1 do 10, a Hal predstavlja atom halogena, reagira sa spojem opće formule (III): H-W-R5 (III) gdje su W i R5 definirani u skladu s bilo kojim od patentnih zahtjeva 1 do 10.
12. Spoj formule (II): [image] naznačen time što su A, B, m i n definirani u skladu s bilo kojim od patentnih zahtjeva 1 do 10, a Hal predstavlja atom halogena; uz izuzetak 2-klor-1-[4-(2-metoksifenil)-3,6-dihidro-2H-piridin-1-il]etanona i 2-klor-1-[4-(4-bromofenil)-3,6-dihidro-2H-piridin-1-il]etanona; u obliku baze ili adicijske soli s kiselinom.
13. Medikament, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 10, ili adicijsku sol tog spoja s farmaceutski prihvatljivom kiselinom.
14. Farmaceutski pripravak, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 10, ili njegovu farmaceutski prihvatljivu sol, i najmanje jednu farmaceutski prihvatljivu pomoćnu tvar.
15. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 10, naznačen time što je namijenjen pripravi medikamenta za sprječavanje ili liječenje središnjih i perifernih neurodegenerativnih bolesti, staračke demencije, epilepsije, Alzheimerove bolesti, Parkinsonove bolesti, Huntingtonove koreje, Downog sindroma, prionskih bolesti, amnezije, shizofrenije, depresije, bipolarnog poremećaja, amiotrofne lateralne skleroze, multiple skleroze, kardiovaskularnih stanja, postishemijskog oštećenja srca, kardiomiopatija, infarkta miokarda, insuficijencije srca, ishemije srca, cerebralnog infarkta, perifernih neuropatija, oštećenja očnog živca i mrežnice, mrežnice pigment degeneracija, glaukoma, ishemije mrežnice, degeneracije makule, ozljeda leđne moždine, ozljeda lubanje, ateroskleroze, stenoza, poremećaja ožiljavanja, alopecije, raka, tumora, metastaza, leukemija, poremećaja dišnog sustava, upale pluća, alergije, astme, kronične opstruktivne bronhopneumopatije, kožne, somatske, visceralne i neurološke boli, kronične neuropatske i upalne boli, autoimunih bolesti, reumatoidnog artritisa, ankilozantnog spondilartritisa, psorijatičnog artritisa, psorijaze s pločastim promjenama, prijeloma kostiju, bolesti kostiju ili osteoporoze.
16. Spoj namijenjen pripravi medikamenta u skladu s patentnim zahtjevom 15, naznačen time što može inhibirati dimeriziranje receptora p75NTR neovisno o njegovom ligandu.
HR20120290T 2008-06-13 2012-04-02 NOVI DERIVATI (PREMOŠTENI PIPERAZINIL)-1-ALKANONA I NJIHOVA UPOTREBA KAO INHIBITORA p75 HRP20120290T1 (hr)

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PCT/FR2009/051118 WO2009150388A1 (fr) 2008-06-13 2009-06-12 NOUVEAUX DERIVES DE (PIPERAZINYL PONTE)-1-ALCANONE ET LEUR UTILISATION COMME INHIBITEURS DE p75

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CN102124006A (zh) 2011-07-13
SI2297148T1 (sl) 2012-05-31
CY1112610T1 (el) 2016-02-10
BRPI0915126A2 (pt) 2016-02-16
BRPI0915126B1 (pt) 2019-09-24
US8193190B2 (en) 2012-06-05
DK2297148T3 (da) 2012-05-07
RS52262B (en) 2012-10-31
JP2011522869A (ja) 2011-08-04

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