HRP20130865T1 - Derivati pirazol piridina kao inhibitori nadph oksidaze - Google Patents

Derivati pirazol piridina kao inhibitori nadph oksidaze Download PDF

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HRP20130865T1
HRP20130865T1 HRP20130865AT HRP20130865T HRP20130865T1 HR P20130865 T1 HRP20130865 T1 HR P20130865T1 HR P20130865A T HRP20130865A T HR P20130865AT HR P20130865 T HRP20130865 T HR P20130865T HR P20130865 T1 HRP20130865 T1 HR P20130865T1
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methyl
pyridine
pyrazolo
dione
chlorophenyl
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HRP20130865AT
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Patrick Page
Mike Orchard
Benoît Laleu
Francesca Gaggini
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Genkyotex Sa
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Claims (16)

1. Derivat pirazol piridina u skladu sa Formulom (I): [image] naznačen time, što G, predstavlja H; G2 predstavlja radikal izabran iz grupe koju čine H; moguće supstituirana C1-C6alkil grupa; moguće supstituirana aril grupa; moguće supstituirana C1-C6alkil aril grupa; moguće supstituirana aril C1-C6alkil grupa; moguće supstituirana heteroaril grupa; moguće supstituirana C1-C6alkil heteroaril grupa; moguće supstituirana heteroaril C1-C6alkil grupa; moguće supstituirana C3-C8-cikloalkil grupa; moguće supstituirana heterocikloalkil grupa; moguće supstituirana alkil C3-C8-cikloalkil grupa; moguće supstituirana C3-C8-cikloalkil C1-C6alkil grupa; moguće supstituirana C1-C6alkil heterocikloalkil grupa i moguće supstituirana heterocikloalkil C1-C6alkil grupa; G3 predstavlja radikal izabran iz grupe koju čine -(CH2)n-R' i -(CH2)P-R5 grupa; R1 predstavlja radikal izabran iz grupe koju čine -NR2R3 grupa; -OR4 grupa; moguće supstituirana heterocikloalkil grupa izabrana iz grupe koju čine moguće supstituirana morfolinil, opciono moguće supstituirana pirolidinil, moguće supstituirana piperidinil, moguće supstituirana dihidroindolil i moguće supstituirana piperazinil grupa; -CHR6R7 grupa; moguće supstituirana acil i -C(O)NR2R3 grupa; R2 i R3 predstavljaju radikale koji su nezavisno jedan od drugog izabrani iz grupe koju čine H; moguće supstituirana C1-C6alkil grupa; moguće supstituirana C2-C6 alkenil grupa; moguće supstituirana C2-C6alkinil grupa; moguće supstituirana aril grupa; moguće supstituirana C1-C6alkil aril grupa; moguće supstituirana aril C1-C6alkil grupa; moguće supstituirana heteroaril grupa; moguće supstituirana alkil heteroaril grupa; moguće supstituirana heteroaril C1-C6alkil grupa; moguće supstituirana C2-C6 alkenil aril grupa; moguće supstituirana aril C2-C6alkenil grupa; moguće supstituirana C2-C6alkenil heteroaril grupa; moguće supstituirana heteroaril C2-C6alkenil grupa; moguće supstituirana C3-C8-cikloalkil grupa; moguće supstituirana heterocikloalkil grupa; moguće supstituirana alkil C3-C8-cikloalkil grupa; moguće supstituirana C3-C8-cikloatkil C1-C6alkil grupa; moguće supstituirana C1-C6alkil heterocikloalkil grupa i moguće supstituirana heterocikloalkil C1-C6alkil grupa ili radikal NR2R3 formira strukturu prstena koja može biti moguće supstituirana heteroaril i moguće supstituirana heterocikloalkil grupa; R4 predstavlja radikal izabran iz grupe koju čine H; moguće supstituirana alkoksi C1-C6alkil grupa; moguće supstituirana C1-C6alkil grupa; moguće supstituirana C2-C6alkenil grupa; moguće supstituirana C2-C6alkinil grupa; moguće supstituirana aril grupa; moguće supstituirana C1-C6alkil aril grupa; moguće supstituirana aril C1-C6alkil grupa; moguće supstituirana heteroaril grupa; moguće supstituirana alkil heteroaril grupa; moguće supstituirana heteroaril C1-C6alkil grupa; moguće supstituirana C2-C6alkenil aril grupa; moguće supstituirana aril C2-C6alkenil grupa; moguće supstituirana C2-C6alkenil heteroaril grupa; moguće supstituirana heteroaril C2-C6alkenil grupa; moguće supstituirana C3-C8-cikloalkil grupa; moguće supstituirana heterocikloalkil grupa; moguće supstituirana alkil C3-C8-cikloatkil grupa; moguće supstituirana C3-C8-cikloalkil C1-C6alkil grupa; moguće supstituirana C1-C6alkil heterocikloalkil grupa i moguće supstituirana heterocikloalkil C1-C6alkil grupa; R1 predstavlja radikal izabran iz grupe koju čine moguće supstituirana alkoksi grupa; moguće supstituirana alkoksi C1-C6alkil grupa; moguće supstituirana metil grupa; moguće supstituirana C1-C6alkil aril grupa; moguće supstituirana alkil heteroaril grupa; moguće supstituirana C2-C6alkenil aril grupa; moguće supstituirana C2-C6alkenil heteroaril grupa; moguće supstituirana alkil C3-C8-cikloalkil grupa; moguće supstituirana C3-C8- cikloalkil C1-C6alkil grupa; moguće supstituirana C1-C6alkil heterocikloalkil grupa i moguće supstituirana heterodkloalkil C1-C6alkil grupa; R6 i R7 predstavljaju radikale koji su nezavisno jedan od drugoga izabrani iz grupe koju čine moguće supstituirana C2-C6alkenil grupa; moguće supstituirana C2-C6alkinil grupa; moguće supstituirana aril grupa; moguće supstituirana C1-C6alkil aril grupa; moguće supstituirana aril C1-C6alkil grupa; moguće supstituirana heteroaril grupa; moguće supstituirana alkil heteroaril grupa; moguće supstituirana heteroaril C1-C6alkil grupa; moguće supstituirana C2-C6alkenil aril grupa; moguće supstituirana aril C2-C6alkenil grupa; moguće supstituirana C2-C6alkenil heteroaril grupa; moguće supstituirana heteroaril C2-C6alkenil grupa; moguće supstituirana C3-C8-cikloalkil grupa; moguće supstituirana heterodkloalkil grupa; moguće supstituirana alkil C3-C8-cikloalkil grupa; moguće supstituirana C3-C8-cikloalkil C1-C6alkil grupa; moguće supstituirana C1-C6alkil heterodkloalkil grupa i moguće supstituirana heterodkloalkil C1-C6alkil grupa ili –CHR6R7 radikal formira moguće supstituiranu strukturu prstena izabranu iz grupe koju čine moguće supstituirana heteroaril, moguće supstituirana cikloalkil grupa i moguće supstituirana heterocikloalkil grupa; n predstavlja cijeli broj izabran iz grupe koju čine brojevi od 0 do 5; p predstavlja cijeli broj izabran iz grupe koju čine brojevi od 3 do 5; G4 predstavlja radikal izabran iz grupe koju čine H; moguće supstituirana acil grupa; moguće supstituirana acil amino grupa; moguće supstituirana acil C1-C6alkil grupa; moguće supstituirana C1-C6alkil grupa; moguće supstituirana C2-C6alkenil grupa; moguće supstituirana C2-C6alkinil grupa; moguće supstituirana aril grupa; moguće supstituirana C1-C6alkil aril grupa; moguće supstituirana aril C1-C6alkil grupa; moguće supstituirana heteroaril grupa; moguće supstituirana C1-C6alkil heteroaril grupa; moguće supstituirana heteroaril C1-C6alkil grupa; moguće supstituirana C2-C6alkenil aril grupa; moguće supstituirana aril C2-C6alkenil grupa; moguće supstituirana C2-C6alkenil heteroaril grupa; moguće supstituirana heteroaril C2-C6alkenil grupa; moguće supstituirana C3-C8-cikloalkil grupa; moguće supstituirana heterodkloalkil grupa; moguće supstituirana C1-C6alkil C3-C8-cikloalkil grupa; moguće supstituirana C3-C8-cikloalkil C1-C6alkil grupa; moguće supstituirana C1-C6alkil heterodkloalkil grupa i moguće supstituirana heterodkloalkil C1-C6alkil grupa; G5 predstavlja H; kao i njegove farmaceutski prihvatljive soli, naznačen time, što se termin "supstituiran" odnosi na grupe koje i same mogu biti supstituirane sa od 1 do 5 supstituenata izabranih iz grupe koju čine "C1-C6alkil”, "C2-C6alkenil”, "C2-C6alkinil”, "C3-C8-cikloalkil”, "heterocikloalkil”, "C1-C6alkil aril”, ''C1-C6alkil heteroaril”, "C1-C6alkil cikloalkil”, ''C1-C6alkil heterodkloalkil”, "amino”, "aminosulfonil”, "amonij”, "acil amino", "amino karbonil”, "aril”, “heteroaril”, " sulfinil”, "sulfonil”, "alkoksi”, "alkoksi karbonil”, "karbamat”, "sulfanil”, "halogen”, trihalometil, cijano, hidroksi, merkapto, nitro grupa.
2. Derivat prema patentnom zahtjevu 1, naznačen time, što G2 predstavlja moguće supstituiranu C1-C6alkil grupu.
3. Derivat prema patentnom zahtjevu 1, naznačen time, što G2 predstavlja moguće supstituiranu aril grupu.
4. Derivat prema bilo kojem patentnom zahtjevu od 1 do 3, naznačen time, što G3 predstavlja -(CH2)n-R1 grupu; R1 i n su kao što je to opisano u prethodnim patentnim zahtjevima.
5. Derivat prema bilo kojem patentnom zahtjevu od 1 do 3, naznačen time, što G3 predstavlja -(CH2)n-R1 grupu; R1 predstavlja -NR2R3 grupu; R2, R3 i n su kao što je to opisano u prethodnim patentnim zahtjevima.
6. Derivat prema bilo kojem patentnom zahtjevu od 1 do 5, naznačen time, što G3 predstavlja -(CH2)n-R1 grupu; R1 predstavlja -NR2R3 grupu; R3 predstavlja moguće supstituiranu aril C1-C6alkil grupu; R2 i n su kao što je to opisano u prethodnim patentnim zahtjevima.
7. Derivat prema bilo kojem patentnom zahtjevu od 1 do 4, naznačen time, što G3 predstavlja -(CH)n-R1 grupu; R1 predstavlja moguće supstituiranu heterocikloalkil grupu; n je kao što je to opisano u prethodnim patentnim zahtjevima.
8. Derivat prema bilo kojem patentnom zahtjevu od 1 do 5, naznačen time, što G3 predstavlja -(CH2)n-R1 grupu; R' predstavlja -NR2R3 grupu; R2 predstavlja moguće supstituiranu C1-C6alkil grupu; R3 i n su kao što je to opisano u prethodnim patentnim zahtjevima.
9. Derivat prema bilo kojem patentnom zahtjevu od 1 do 8, naznačen time, što G3 predstavlja -(CH2)n-R1 grupu; n predstavlja 1; R 1 je kao što je to opisano u prethodnim patentnim zahtjevima.
10. Derivat prema bilo kojem patentnom zahtjevu od 1 do 3, naznačen time, što G3 predstavlja -(CH2)p-R5; R5 i p su kao što je to opisano u prethodnim patentnim zahtjevima.
11. Derivat prema bilo kom patentnom zahtjevu od 1 do 3, naznačen time, što G3 predstavlja -(CH2)p-R5; naznačen time, što p predstavlja 3, a R5 je kao što je to opisano u prethodnim patentnim zahtjevima.
12. Derivat prema bilo kom patentnom zahtjevu od 1 do 11 izabran iz grupe koja slijedi: 5-benzil-2-(2-klorofenil)-4-(morfolin-4-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-butil-2-metil-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-[4-(benziloksi)fenil]-4-butil-5-(4-klorobenzil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-[4-(benziloksi)fenil]-4-butil-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-[4-(benziloksi)fenil]-4-butil-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c] piridin-3,6(2H,5H)-dion; 4-butil-2-(2-kloro-4-fluorofenil)-5-(furan-2-ilmetil)-1H-pirazol[4,3-c] piridin-3,6(2H,5H)-dion; 4-butil-2-(2-kloro-4-fluorofenil)-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c] piridin-3,6(2H,5H)-dion; 4-butil-2-(2-kloro-4-fluorofenil)-5-(2-metoksi etil)-1H-pirazol[4,3-c] piridin-3,6 (2H,5H)-dion; 4-butil-2-(2-kloro-4-fluorofenil)-5-(2-piridin-2-iletil)-1H-pirazol[4,3-c] piridin-3,6(2H,5H)-dion; 4-butil-2-(2-kloro-4-fluorofenil)-5-(3,5-dimetoksibenzil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)- dion; 4-{[benzil(metil)amino]metil}-2-(2-kloro-4-fluorofenil)-5-(3-metoksipropil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-[4-(benziloksi)fenil]-4-butil-5-(2-metoksietil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-butil-2-(2-kloro-4-fluorofenil)-5-[2-(morfolin-4-ilmetil)benzil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(3-klorofenil)-4-(metoksimetil)-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(3-klorofenil)-4-(metoksimetil)-5-[2-(morfolin-4-ilmetil)benzil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-benzil-5-(3-etoksipropil)-4-{[(3-fluorobenzil)(metil)amino]metil}-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(3-klorofenil)-5-metil-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 5-(4-klorobenzil)-2-(3-klorofenil)-4-{[(3-fluorobenzil)(metil)amino]metil}-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(3-klorofenil)-4-(metoksimetil)-5-(2-piridin-2-iletil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 5-(4-klorobenzil)-4-(metoksimetil)-2-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-metil-4-(3-fenoksipropil)-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-benzil-5-(2-metoksietil)-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-benzil-4-{[(3-fluorobenzil)(metil)amino]metil}-5-(2-metoksietil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(3-klorofenil)-4-{[(3-fluorobenzil)(metil)amino]metil}-5-(2-piridin-2-iletil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-kloro-4-fluorofenil)-5-(3,5-dimetoksibenzil)-4-(metoksimetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-kloro-4-fluorofenil)-5-(2-piridin-2-iletil)-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(3-klorofenil)-5-(2-piridin-2-iletil)-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-kloro-4-fluorofenil)-5-(furan-2-ilmetil)-4-(metoksimetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-kloro-4-fluorofenil)-4-(metoksimetil)-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-benzil-5-(3,5-dimetoksibenzil)-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(3-klorofenil)-4-{[(3-fluorobenzil)(metil)amino]metil}-5-(2-metoksietil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-[4-(benziloksi)fenil]-5-(piridin-3-ilmetil)-4-(pirolidin-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-(metoksimetil)-2-metil-5-(2-piridin-2-iletil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(3-klorofenil)-5-(2-metoksietil)-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-kloro-4-fluorofenil)-5-(2-metoksietil)-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-kloro-4-fluorofenil)-5-(3-etoksipropil)-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(3-klorofenil)-5-(3-etoksipropil)-4-{[(3-fluorobenzil)(metil)amino]metil}-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-benzil-5-(3-etoksipropil)-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-[4-(benziloksi)fenil]-5-(4-klorobenzil)-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-[4-(benziloksi)fenil]-4-{[(3-fluorobenzil)(metil)amino]metil}-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-[4-(benziloksi)fenil]-5-(4-klorobenzil)-4-{[(3-fluorobenzil)(metil)amino]metil}-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-[4-(benziloksi)fenil]-5-metil-4-(pirolidin-1-itmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 5-(4-klorobenzil)-2-metil-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; N-[3-({2-[4-(benziloksi)fenil]-3,6-diokso-4-(pirolidin-1-ilmetil)-1,2,3,6-tetrahidro-5H-pirazol[4,3-c]piridin-5-il}metil)fenil]acetamid; N-{3-[(2-[4-(benziloksi)fenil]-4-{[(3-fluorobenzil)(metil)amino]metil}-3,6-diokso-1,2,3,6-tetrahidro-5H-pirazol[4,3-c]piridin-5-il)metil]fenil}acetamid; 2-(3-klorofenil)-5-(3-etoksipropil)-4-(pirolidin-1-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-metil-4-(fenoksimetil)-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(4-fluorofenoksi)metil]-2-metil-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(4-fluorofenoksi)metil]-5-(2-metoksietil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(4-fluorofenoksi)metil]-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2,5-diklorofenil)-4-f(4-fluorofenoksi)metil]-5-metii-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2,5-diklorofenil)-4-[(4-fluorofenoksi)metil]-5-(2-metoksietil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 5-(4-klorobenzil)-4-[(4-fluorofenoksi)metil]-2-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-metil-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 5-(2-metoksibenzil)-2-metil-4-(3-fenoksipropil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(4-fluorofenoksi)metil]-2-metil-5-[(6-morfolin-4-ilpiridin-2-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(4-fluorofenoksi)metil]-2-metil-5-[2-(tetrahidro-2H-piran-2-il)etil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(4-fluorofenoksi)metil]-2-metil-5-(2-piridin-2-iletil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 5-(3-metoksibenzil)-2-metil-4-(3-fenoksipropil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-metil-4-{3-fenoksipropil)-5-(2-piridin-2-iletil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion 4-[(4-klorofenoksi)metil]-5-(3-metoksibenzil)-2-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-5-(3-etoksipropil)-2-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-5-(3-metoksibenzil)-2-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(4-klorofenoksi)metil]-5-(3-etoksipropil)-2-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(4-klorofenoksi)metil]-2-metil-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-metil-5-(2-piridin-2-iletil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; N-[3-({4-[(benziloksi)metil]-2-metil-3,6-diokso-1,2,3,6-tetrahidro-5H-pirazol[4,3-c]piridin-5-il}metil)fenil]acetamid; N-[3-({4-[(4-klorofenoksi)metil]-2-metil-3,6-diokso-1,2,3,6-tetrahidro-5H-pirazol[4,3-c]piridin-5-il}metil)fenil]acetamid; 4-[(4-fluorofenoksi)metil]-2-metil-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(4-fluorofenoksi)metil]-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(4-fluorofenoksi)metil]-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-metil-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(4-fluorofenoksi)metil]-5-[(5-metil-1,2,4-oksadiazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-(4-benzilmorfolin-2-il)-2-(2-klorofenil)-5-metil-1H-pirazol[4,3-c]pin'din-3,6(2H,5H)-dion; 2-(2-klorofenH)-5-(3-etoksipropil)-4-[(4-fluorofenoksi)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(4-fluorofenoksi)metil]-5-(2-piridin-2-iletil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(4-klorofenoksi)metil]-2-(2-klorofenil)-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(4-fluorofenoksi)metil]-5-[(2-metil-1,3-tiazol-4-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-(2-piridin-2-iletil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-(3-etoksipropil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; N-[3-({2-(2-klorofenil)-4-[(4-fluorofenoksi)metil]-3,6-diokso-1,2,3,6-tetrahidro-5H-pirazol[4,3-c]piridin-5-il}metil)fenil]acetamid; 4-[(4-klorofenoksi)metil]-2-(2-klorofenil)-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[metil(fenil)amino]metil3-5-(2-piridin-2-iletil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-5-(3-etoksipropil)-4-{[metil(fenil)amino]metil}-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[metU(fenil)amino]metil}-5-(piridin-4-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(4-klorofenoksi)metil]-2-(2-klorofenil)-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-[(3-etil-1,2,4-oksadiazol-5-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-(piridin-4-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-(1,3-tiazol-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; tert-butil4-({4-[(benziloksi)metil]-2-(2-klorofenil)-3,6-diokso-1,2,3,6-tetrahidro-5H-pirazol[4,3-c]piridin-5-il}metil)piperidin-1-karboksilat; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-(piperidin-4-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-[3-(dietilamino)propil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-(piridin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-(2-metoksietil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(4-klorofenoksi)metil]-2-(2-klorofenil)-5-(piridin-4-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-[(1-metilpiperidin-4-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(3-klorofenoksi)metil]-2-(2-ktorofenil)-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-5-metil-4-[(2,2,2-trifluoro-1-feniletoksi)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-5-metil-4-(3-fenoksi propit)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-[(5-metil-1,2,4-oksadiazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-[(2-metil-1,3-tiazol-4-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-(pirazin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-fluorobenzil)(metil)amino]metil}-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-5-metil-4-[(4-fenilpiperidin-1-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-{4-[(benziloksi)metil]-2-(2-klorofenil)-3,6-diokso-1,2,3,6-tetrahidro-5H-pirazol[4,3-c]piridin-5-il}-N,N-dimetilacetamid; 2-(2-klorofenil)-4-[(3-metoksifenoksi)metil]-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(4-fluorofenoksi)metil]-5-(piridin-4-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-metoksibenzil)oksi]metil}-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenH)-5-metil-4-{3-[metil(fenil)amino]propil}-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(4-metoksibenzil)oksi]metil}-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil)oksi]metil}-2-(2-klorofenil)-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[3-(2,3-dihidro-1H-indolil-il)propil]-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-[(1-metil-1H-pirazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-5-metil-4-[(naftalen-1-iloksi)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(4-klorobenzil)oksi]metil}-2-(2-klorofenil)-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[2-(4-klorofenil)etoksi]metil}-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[benzil(metil)amino]metil}-2-(2-klorofenil)-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-[(4-metilmorfolin-2-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-klorofenil)-5-(piperidin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[3-(dimetilamino)fenoksi]metil}-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-5-metil-4-{[metil(piridin-2-ilmetil)amino]metil}-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil)oksi]metil}-2-(2-klorofenil)-5-(piridin-4-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil)oksi]metil}-2-(2-klorofenil)-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil)oksi]metil}-2-(2-klorofenil)-5-(2-metoksietil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-5-(2-metoksietil)-4-[(3-metoksifenoksi)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-fluorobenzil)(metil)amino]metil}-5-(2-metoksietil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(3-metoksifenoksi)metil]-5-(piridin-4-Hmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(3-klorobenzil)oksi]metil}-2-(2-klorofenil)-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-({[3-(dimetitamino)benzil]oksi}metil)-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(difenilmetoksi)metil]-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(3-metoksifenoksi)metil]-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-metoksibenzil)(metil)amino]metil}-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-fluorobenzil)(metil)amino]metil}-5-[(1-metil-1H-pirazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil)(metil)amino]metil}-2-(2-klorofenil)-5-(2-metoksietil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil)oksi]metil]-2-(2-klorofenil)-5-[(1-metil-1H-pirazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofeml)-5-metil-4-{[metil(piridin-3-ilmetil)amino]metil}-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil)(metil)amino]metil}-2-(2-klorofenil)-5-[(1-metil-1H-pirazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-metoksibenzil)(metil)amino]metil}-5-[(1-metil-1H-pirazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-metoksibenzil)oksi]metil}-5-[(1-metil-1H-pirazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(3-metoksifenoksi)metil]-5-[(1-metil-1H-pirazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(3-metoksifenoksi)metil]-5-(pirazin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-5-(2-metoksietil)-4-{[(3-metoksifenil)(metil)amino]metil}-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-metoksifenil)(metil)amino]metil}-5-[(1-metil-1H-pirazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil){metil)amino]metil}-2-(2-klorofenil)-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-metoksibenzil)oksi]metil}-5-(pirazin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-metoksibenzil)oksi]metil}-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-metoksibenzil)oksi]metil}-5-(2-metoksietil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-fluorobenzil)(metil)amino]metil}-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil)(metil)amino]metil}-2-(2-klorofenil)-5-(pirazin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-metoksibenzil)(metil)amino]metil)-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-[(3-metoksifenoksi)metil]-5-[(4-metilmorfolin-2-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[4-(3-metoksifenil)piperazin-1-il]metil}-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-metoksifenil)(metil)amino]metil}-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[4-(2-klorofenil)piperazin-1-il]metil}-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[4-(3-klorofenil)piperazin-1-il]metil}-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil)oksi]metil}-2-(2-metoksifenil)-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil)oksi]metil}-2-(2-klorofenil)-5-(pirazin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[metil(piridin-2-ilmetil)amino]metil}-5-(piridin-3-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-5-[(1-metil-1H-pirazol-3-il)metil]-4-{[metil(piridin-2-ilmetil)amino]metil}-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(3-metoksibenzil)oksi]metil}-2-(2-metoksifenil)-5-(pirazin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(3-metoksibenzil)oksi]metil}-2-(2-metoksifenil)-5-[(1-metil-1H-pirazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[(3-metoksibenzil)(metil)amino]metil}-5-(pirazin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-metoksifenil)-5-[(1-metil-1H-pirazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(3-metoksifenoksi)metil]-2-(2-metoksifenil)-5-[(1-metil-1H-pirazol-3-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2M2-klorofenil)-5-[(1-metil-1H-pirazol-3-il)metil]-4-{[metil(piridin-3-ilmetil)amino]metil}-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-4-{[metil(piridin-2-ilmetil)amino]metil}-5-(pirazin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-metoksifenil)-4-{[4-(3-metoksifenil)piperazin-1-il]metil}-5-metil-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-metoksifenil)-5-metil-4-[(4-piridin-2-ilpiperazin-1-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-5-metil-4-[(4-piridin-2-ilpiperazin-1-il)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-{[(2-klorobenzil)oksi]metil}-2-(2-metoksifenil)-5-(pirazin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 4-[(benziloksi)metil]-2-(2-metoksifenil)-5-(pirazin-2-ilmetil)-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; 2-(2-klorofenil)-5-[(1-metil-1H-pirazol-3-il)metil]-4-[(piridin-3-ilmetoksi)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion; i 2-(2-klorofenil)-5-(pirazin-2-ilmetil)-4-[(piridin-3-ilmetoksi)metil]-1H-pirazol[4,3-c]piridin-3,6(2H,5H)-dion.
13. Farmaceutski pripravak koji sadrži najmanje jedan od derivata prema bilo kojem patentnom zahtjevu od 1 do 12 i njegov farmaceutski prihvatljiv nosač, diluent ili ekscipijent.
14. Derivat prema bilo kojem patentnom zahtjevu od 1 do 12, za upotrebu u obliku lijeka.
15. Derivat pirazol piridina prema bilo kom patentnom zahtjevu od 1 do 12, za upotrebu u tretmanu bolesti ili stanja izabranih iz grupe koju čine kardiovaskularni poremećaji, respiratorni poremećaji, poremećaji metabolizma, poremećaji na koži, poremećaji u kostima, neuroupalni i/ili neurodegenerativni poremećaji, oboljenja bubrega, poremećaji u reprodukciji, bolesti koje utječu na oko i/ili leću oka i/ili stanja koja utječu na unutrašnje uho, upalni poremećaji, bolesti jetre, bol, rak, alergijski poremećaji, ozlijede, septički, hemoragični i anafilaktički šok, bolesti i poremećaji gastrointestinalnog sistema, angiogeneza, stanja koja su uvjetovana angiogenezom, kao i druga oboljenja i/ili poremećaji koje karakterizira izmijenjena aktivnost ili funkcija oksidaze nikotinamid adenin dinukleotid fosfata (NADPH oksidaze).
16. Postupak pripreme spoja Formule (I), koji obuhvaća korak ciklizacije spoja Formule (VIII) uz prisutnost baze: [image] naznačen time, što R8 predstavlja C1-C6alkil grupu poput metil, etil, propil, izopropil ili butil grupe; G, predstavlja H; G2, G3, G4 i G5 predstavljaju grupe definirane prethodno, u bilo kom od prethodnih patentnih zahtjeva.
HRP20130865AT 2008-09-23 2013-09-13 Derivati pirazol piridina kao inhibitori nadph oksidaze HRP20130865T1 (hr)

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EP20080164853 EP2165707A1 (en) 2008-09-23 2008-09-23 Pyrazolo pyridine derivatives as NADPH oxidase inhibitors
PCT/IB2009/054150 WO2010035219A2 (en) 2008-09-23 2009-09-22 Pyrazolo pyridine derivatives as nadph oxidase inhibitors

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RU2532161C2 (ru) 2014-10-27
BRPI0919328B8 (pt) 2021-05-25
ES2560840T3 (es) 2016-02-23
IL211890A0 (en) 2011-06-30
PT2349261E (pt) 2013-10-31
PL2349261T3 (pl) 2014-01-31
JP5700836B2 (ja) 2015-04-15
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KR101703361B1 (ko) 2017-02-06
AU2009298006B2 (en) 2014-03-06
US20110178081A1 (en) 2011-07-21
CY1114879T1 (el) 2016-12-14
US8455485B2 (en) 2013-06-04
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KR20110059719A (ko) 2011-06-03
BRPI0919328B1 (pt) 2020-11-24
SMT201300158B (it) 2014-03-07
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