HRP20130044T1 - Derivati piridizinona - Google Patents

Derivati piridizinona Download PDF

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HRP20130044T1
HRP20130044T1 HRP20130044TT HRP20130044T HRP20130044T1 HR P20130044 T1 HRP20130044 T1 HR P20130044T1 HR P20130044T T HRP20130044T T HR P20130044TT HR P20130044 T HRP20130044 T HR P20130044T HR P20130044 T1 HRP20130044 T1 HR P20130044T1
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Croatia
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phenyl
methyl
pyridazin
propoxy
pyrrolidin
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HRP20130044TT
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Robert L. Hudkins
Kurt A. Josef
Ming Tao
Nadine C. Becknell
Greg Hostetler
Lars J. S. Knutsen
Allison L. Zulli
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Cephalon, Inc.
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Publication of HRP20130044T1 publication Critical patent/HRP20130044T1/hr

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Claims (44)

1. Spoj prema formuli I*: [image] ili stereoizomerni oblik, mješavina stereoizomernih oblika ili farmaceutski prihvatljiva sol istog, naznačen time da: X i Xa predstavljaju svaki nezavisno CH ili N; Y predstavlja S(O)q, O ili NR15; R1 predstavlja piperidinski ili pirolidinski prsten, kojeg opcionalno supstituiraju 1 do 3 R20 skupine; R2 predstavlja [image] gdje: R2 predstavlja skupinu u para poziciji u odnosu na Y-(CHR4)m-R1 skupinu; svaki R3 predstavlja: R2 nezavisno H, F, Cl, Br, I, OR21, NR23R24, NO2, CN, CF3, (C1-C6)alkil, C(=O)R21, CO2R21 ili C(=O)NR23R24; ili kada je R3 u orto poziciji u odnosu na R2, a R2 predstavlja (i) ili (iv), R3 i R'4 tada zajedno mogu formirati -(CH2)S-, -CH2Z-, -ZCH2-, -ZCH2CH2- ili CH2CH2Z-; gdje Z predstavlja O, S(O)y ili NR2'; ili kada je R3 u orto poziciji u odnosu na R2, a R2 predstavlja (iv) ili (v), R3 i R13 tada zajedno mogu formirati -(CH2)S-, -CH2Z- , -ZCH2-, -ZCH2CH2- ili CH2CH2Z-; svaki R4 predstavlja nezavisno H, (C1-C6)alkil ili OR21, gdje alkilnu skupinu opcionalno supstituiraju 1 do 3 R20 skupine; R2 predstavlja H, (C1-C6)alkil, cikloalkil, aril, arilalkil, heteroaril, heterocikloalkil, C(=O)R27 ili CO2R27, gdje alkil, cikloalkil, aril, arilalkil, heteroaril ili heterocikloalkilnu skupinu opcionalno supstituiraju 1 do 3 R10 skupine; R13 i R14 predstavljaju svaki nezavisno H, (C1-C6)alkil, aril, arilalkil (C1-C6)alkoksil, S(=O)y-(C1-C6)alkil, cikloalkil, heterocikloalkil ili heteroaril; ili R13 i R14 zajedno s atomom ugljika preko kojega su povezani formiraju fuzionirani fenilni, tienilni, pirolilni, oksazolilni, piridinilni ili (C3-C6)cikloalkilni prsten; i gdje fuzionirani fenilni, tienilni, pirolilni, oksazolilni, piridinilni ili cikloalkilni prsten opcionalno supstituiraju 1 do 3 R20 skupine; R15 predstavlja H, (C1-C6)alkil, C(=O)R, CO2R25; R20 pri svakom pojavljivanju predstavlja nezavisno H, F, Cl, Br, I, OR2, OR22, NR23R24, NHOH, NO2, CN, CF3, (C1-C6)alkil opcionalno supstituiran s OR26, (C2-C6)alkenilom, (C2-C6)alkinilom, (C3-C7)cikloalkil(C0-C4)alkilom, 3- do 7-članim heterocikloalkil(C0-C4)alkilom, fenilom, 5- ili 6-članim heteroaril(C0-C4)alkilom, arilalkilom, (=O), C(=O)R21, CO2R21, OC(=O)R21, C(=O)NR23R24, NR27C(=O)R21, NR27C(=O)OR21, OC(=O)NR23R24, NR27C(=S)R21 ili S(O)qR21; svaki R21 predstavlja nezavisno H, (C1-C6)alkil, aril ili arilalkil; svaki R2 predstavlja nezavisno ostatak amino kiseline nastao nakon uklanjanja hidroksilne skupine iz karboksilne skupine; svaki R23 i R24je nezavisno odabran od H, (C1-C6)alkila i arila, ili R23 i R24, zajedno sa atomom dušika za koji su vezani, formiraju 3-7-člani heterociklični prsten opcionalno supstituiran s =O; R25 predstavlja (C1-C6)alkil, aril ili alkilaril; R26 predstavlja H, (C1-C6)alkil, aril ili alkilaril; R27 predstavlja H ili (C1-C6)alkil; m predstavlja 1, 2, 3, 4 ili 5 kada je R1 vezan preko atoma dušika, a m predstavlja 0, 1, 2, 3, 4 ili 5 kada je R1 vezan preko atoma ugljika; n predstavlja 1, 2 ili 3; q predstavlja 0, 1 ili 2; s predstavlja 1, 2 ili 3; i y predstavlja 0, 1 ili 2.
2. Spoj prema patentnom zahtjevu 1, formule le: [image] ili stereoizomerni oblik, mješavina stereoizomernih oblika ili farmaceutski prihvatljiva sol istog, naznačen time da: R predstavlja piperidinski ili pirolidinski prsten kojeg opcionalno supstituiraju 1 do 3 R20 skupine; R1 predstavlja H, (C1-C6)alkil, cikloalkil, aril, arilalkil, heteroaril, heterocikloalkil, C(=O)R27 ili CO2R27, gdje alkilnu, cikloalkilnu, arilnu, arilalkilnu, heteroarilnu ili heterocikloalkilnu skupinu opcionalno supstituiraju 1 do 3 R2 skupine; R3 i R14 predstavljaju svaki nezavisno H, (C1-C6)alkil, aril, arilalkil (C1-C6)alkoksil, S(=O)y-(C1-C6)alkil, cikloalkil, heterocikloalkil ili heteroaril; ili R13 i R14 zajedno s atomom ugljika preko kojeg su povezani formiraju fuzionirani fenilni, tienilni, pirolilni, oksazolilni, pirdinilni ili (C3-C6)cikloalkilni prsten; i gdje fuzionirani fenilni, tienilni, pirolilni, oksazolilni, pirdinilni ili cikloalkilni prsten opcionalno supstituiraju 1 do 3 R20 skupine; R20pri svakom pojavljivanju predstavlja nezavisno H, F, Cl, Br, I, OR21, OR22, NR23R24, NHOH, NO2, CN, CF3, (C1-C6)alkil opcionalno supstituiran s OR, (C2-C6)alkenilom, (C2-C6)alkinilom, (C3-C7)cikloalkil(C0-C4)alkilom, 3- do 7- članim heterocikloalkil(C0-C4)alkilom, fenilom, 5- ili 6-članim heteroaril(C0-C4)alkilom, arilalkilom, (=O), C(=O)R21, CO2R21, OC(=O)R21, C(=O)NR23R24, NR27C(=O)R21, NR27C(=O)OR21, OC(=O)NR23R24, NR27C(=S)R21 ili S(O)qR21; svaki R2 predstavlja nezavisno H, (C1-C6)alkil, aril ili arilalkil; svaki R22 predstavlja nezavisno ostatak amino kiseline nastao nakon uklanjanja hidroksilne skupine iz karboksilne skupine, svaki R23 i R24je nezavisno odabran od H, (C1-C6)alkila i arila, ili R23 i R24, zajedno s atomom dušika za koji su vezani, formiraju 3-7-člani heterociklični prsten opcionalno supstituiran s =O; R26 predstavlja H, (C1-C6)alkil, aril ili alkilaril; i R27 predstavlja H ili (C1-C6)alkil;
3. Spoj prema patentnom zahtjevu 1, naznačen time da najmanje jedan od X i Xa predstavlja CH.
4. Spoj prema patentnom zahtjevu 3, naznačen time da Y predstavlja 0.
5. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time da je opcionalno supstituirani piperidinski ili pirolidinski prsten vezan preko atoma dušika.
6. Spoj prema patentnom zahtjevu 5, naznačen time da je piperidinski ili pirolidinski prsten supstituiran s jednom ili dvije alkilne skupine.
7. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time da je piperidinski prsten vezan preko atoma ugljika.
8. Spoj prema patentnom zahtjevu 7, naznačen time da je piperidinski prsten N-supstituiran cikloalkilom.
9. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time da R13 i R14, zajedno sa atomima ugljika preko kojih su povezani, formiraju fuzionirani fenilni, tienilni, oksazolilni, pirdinilni ili (C3-C6)cikloalkilni prsten; i gdje fuzionirani fenilni, tienilni, pirolilni, oksazolilni, pirdinilni ili cikloalkilni prsten opcionalno supstituiraju 1 do 3 R20 skupine.
10. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time da R12 predstavlja H, (C1-C6)alkil, cikloalkil, aril, arilalkil ili heteroaril.
11. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time da R2 predstavlja: [image]
12. Spoj prema patentnom zahtjevu 2 ili 4, naznačen time da R13 i R14 predstavljaju svaki nezavisno H ili (C1-C6)alkil.
13. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time da R14 predstavlja heteroaril.
14. Spoj prema patentnom zahtjevu 1, naznačen time da R4 predstavlja H, alkil ili alkoksil.
15. Spoj prema patentnom zahtjevu 1, naznačen time da R4 predstavlja H ili Cialkil.
16. Spoj prema patentnom zahtjevu 1, naznačen time da m predstavlja 0 ili 1 kada je R1 vezan preko atoma ugljika.
17. Spoj prema patentnom zahtjevu 7 kada isti ovisi o patentnom zahtjevu 1, naznačen time da m predstavlja 0 ili 1.
18. Spoj prema patentnom zahtjevu 1, naznačen time da m predstavlja 3 kada je R1 vezan preko atoma dušika.
19. Spoj prema patentnom zahtjevu 6, naznačen time da m predstavlja 3.
20. Spoj prema patentnom zahtjevu 1, naznačen time da s predstavlja 2.
21. Spoj prema patentnom zahtjevu 1, naznačen time da n predstavlja 0 ili 1.
22. Spoj prema patentnom zahtjevu 6, naznačen time da R1 predstavlja: [image]
23. Spoj prema patentnom zahtjevu 22, naznačen time da R20 predstavlja F, Cl, CF3, NR23R24 ili (C1-C6)alkil opcionalno supstituiran s OR26, cikloalkil(C0-C4)alkilom ili heterocikloalkil(C0-C4)alkilom.
24. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time da R23 i R24 predstavljaju svaki nezavisno (C1-C6)alkil.
25. Spoj prema patentnom zahtjevu 1, naznačen time da Y-(CHR4)m-R1 predstavlja: [image]
26. Spoj prema patentnom zahtjevu 1, naznačen time da kada R4 predstavlja OR21, R21 predstavlja H ili (C1-C6)alkil.
27. Spoj prema patentnom zahtjevu 1, naznačen time da je odabran iz skupine koju čine: 2-metil-6-{4-[(R)-2-metil-3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-[4-(1-ciklopentil-piperidin-4-iloksi)-fenil]-2-metil-2H-piridazin-3-on; 6-{3,5-difluoro-4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2-metil-2H-piridazin-3-on; 6-{3-kloro-4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2-metil-2H-piridazin-3-on; 6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-5-piridin-2-il-2H piridazin-3-on; 6-[4-(1-ciklobutil-piperidin-4-iloksi)-fenil]-5-piridin-2-il-2H-piridazin-3-on; 2-(2-fluoro-etil)-6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-{3-fluoro-4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6- [3 -fluoro4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 4-metil-6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 4-metil-6-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 4-{4-[3-((S)-2-hidroksimetil-pirolidin-1-il)-propoksi]-fenil}-2-metil-5,6,7,8-tetrahidro-2H-ftalazin-1-on: 2-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-5-(6-okso-1,6-dihidro-piridazin-3-il)-benzonitril; 2-[3-(piperidin-1-il)-propoksi]-5-(6-okso-1,6-dihidro-piridazin-3-il)-benzonitril; 2-(2-hidroksietil)-6-{4-[3-((R)-2-meti!-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-{4-[(S)-2-metil-3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 4-[4-{3-piperidin-1-il-propoksi)-fenil]-2,5,6,7-tetrahidro-ciklopenta[d]piridazin-1-on; 6- [4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 6-[3-metoksi-4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 6-{3-metoksi-4-[3-((R)-2-metil-pirolidin-1-i!)-propoksi]-fenil}-2H-piridazin-3-on; 6-[2-metil-4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2-pirimidin-2-il-2H-piridazin-3-on; 6-[6-(1-ciklopentil-piperidin-4-iloksi)-piridin-3-il]-2H-piridazin-3-on; 6-[6-(1-izopropil-piperidin-4-il-metoksi)-piridin-3-il]-2H-piridazin-3-on; 6-[6-(1-ciklobutil-piperidin-4-iloksi)-piridin-3-il]'2H-piridazin-3-on; 6-[6-(1-izopropil-piperidin-4-iloksi)-piridin-3-il]-2H-piridazin-3-on; 6-[6-(1-ciklopentil-piperidin-4-iloksi)-piridin-3-il]-2-metil-2H-piridazin-3-on; 6-[6-(1-ciklobutil-piperidin-4-iloksi)-piridin-3-il]-2-metil-2H-piridazin-3-on; 6-[6-(1-ciklobutil-piperidin-4-iloksi)'piridin-3-il]-2-izopropil-2H-piridazin-3-on; 6-{6-[3-((R)-2-metil-pirolidin-1-il)'propoksi]-piridin-3Hl}-2H-piridazin-3-on; 6-[6-(3-piperidin-1-il-propoksi)-piridin-3-il]-2H-piridazin-3-on; 6-[6-(1-ciklobutil-piperidin-4-iloksi)-piridin-3-il]-2-piridin-2-il-2H-piridazin-3-on; 6-[4-(1-ciklopentil-piperidin-4-iloksi)-fenil]-2H-piridazin-3-on; 6-[4-(1-ciklobutil-piperidin-4-iloksi)-fenil]-2H-piridazin-3-on; 6-[4-(1-ciklobutil-piperidin-4-iloksi)-3-fluoro-fenil]-2H-piridazin-3-on; 6-[4-(1-ciklobutil-piperidin-4-iloksi)-fenil]-2-piridin-2-il-2H-piridazin-3-on; 6-[4-((R)-1-cikloheksil-pirolidin-3-iloksi)-fenil]-2H-piridazin-3-on; 6-[4-((R)-1-ciklobutil-pirolidin-3-iloksi)-fenil]-2H-piridazin-3-on; 6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2-(2,2,2-trifluoro-etil)-2H-piridazin-3-on; 6-[4-(3-piperidin-1-il-propoksi)-fenil]-2-(2,2,2-trifluoro-etil)-2H-piridazin-3-on; 4-[4-(1-ciklobutil-piperidin-4-iloksi)-fenil]-2,5,6,7-tetrahidro-ciklopenta[d]piridazin-1-on; 6-{3,5-difluoro-4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-{3,5-dibromo-4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-[4-(1-ciklobutil-piperidin-4-iloksi)-3,5-difluoro-fenil]-2H-piridazin-3-on; 5-metil-6-{4-[3-((R)-2-metil-pirolidin-i-il)-propoksi3-fenil}-2H-piridazin-3-on; 5-etil-6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-{2-metoksi-4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-{2-fluoro-4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-(4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil)-2-piridin-2 il-2H piridazin-3-on; 6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-4-piridin-2-il-2H-piridazin-3-on; 6-[4-(1-ciklobutil-piperidin-4-iloksi)-2-fIuoro-fenil]-2H-piridazin-3-on; 6-[4-(1-ciklobutil-piperidin-4-iloksi)-fenil]-5-metil-2H-piridazin-3-on; 6-{4-[3-((S)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-[4-(3-pirolidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 6-[4-(2-hidroksi-3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 6-{4-[2-hidroksi-3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-{4-[(S)-2-hidroksi-3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-{4-[(R)-2-hidroksi-3-((R)-2-metil-pirolidin-1-il)-propoksi]fenil}-2H-piridazin-3-on; 6-[4-((R)-2-hidroksi-3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksil-fenil}-2H-piridazin-3-on; 2.6-dimetil-5-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 2.6-dimetil-5-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 6-metil-5-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-metil-5-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 2-metil-5-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 2-metil-5-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 5-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2-piridin-2-il-2H-piridazin-3-on; 5-[4-(3-piperidin-1-il-propoksi)-fenil]-2-piridin-2-il-2H-piridazin-3-on; 2-metil-5-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 2-(6-metil-piridil-2-il)-5-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 2-(3-metil-piridin-2-il)-5-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 6-metil-5-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2-piridin-2-il-2H-piridazin-3-on; 6-metil-5-[4-(piperidin-4-iloksi)-fenil]-2H-piridazin-3-on; 5-[4-(1-ciklobutil-piperidin-4-iloksi)-fenil]-6-metil-2H-piridazin-3-on; 5-[4-(1-ciklobutil-piperidin-4-iloksi)-fenil]-6-metil-2-piridin-2-i!-2H-piridazin-3-on; 5-[4-(piperidin-4-iloksi)-fenil]-2H-piridazin-3-on; 5-[4-(1-ciklobutil-piperidin-4-iloksi)-fenil]-2H-piridazin-3-on; 5-i4-(1-ciklobutil-piperidin-4-iloksi)-fenil]-6-metil-2-tiofen-3-il-2H-piridazin-3-on; 6-metil-5-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2-tiofen-3-il-2H-piridazin-3-on; 5-{4-[3-((S)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2-piridin-2-il-2H-piridazin-3-on; 5-[6-(1-ciklobutil-piperidin-4-iloksi)-piridin-3-il]-2H-piridazin-3-on; 2-izopropil-5-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 2-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-6-fenil-2H-piridazin-3-on; 6-metil-2-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 2-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-ftalazin-1-on; 2-[6-(1-ciklobutil-piperidin-4-iloksi)-piridin-3-il]-6-fenil-2H-piridazin-3-on; 2-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-6-piridin-3-il-2H-piridazin-3-on; 8-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-5,6-dihidro-2H-benzo[h]kinolin-3-on; 8-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-5,6-dihidro-3H-benzo[f]kinolin-2-on; 5-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 2-metoksimetil-5-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 5-{4-[(S)-2-metil-3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 5{4-[(R)-2-metil-3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 5-[4-((S)-2-metil-3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 5-[4-((R)-2-metil-3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3 -on; 5-{3,5-dibromo4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 2-metoksimetil-5-{2-metil-4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 5-{2-metil-4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 2-metoksimetil-5-[2-metil-4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 5-[2-metil-4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 5-[4-(1-ciklobutil-piperidin-4-iloksi)-2-metil-fenil]-2-metoksimetil-2H-piridazin-3-on; 4-metoksi-2-metoksimetil-5-{4-[3-({R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; 5-metoksi-2-metoksimetil-4-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi}-fenil}-2H-piridazin-3-on; 5-metoksi-4-{4-[3-((R)-2-metil-pirolidin-1-i!)-propoksi]-fenil}-2H-piridazin-3-on; 6-ciklopropil-2-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; i 5-izopropil-7-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-5H-tieno[2,3-d]piridazin-4-on; ili stereoizomerni oblik, mješavina stereoizomernih oblika ili farmaceutski prihvatljiva sol istih.
28. Spoj prema patentnom zahtjevu 27, naznačen time da je spoj odabran iz skupine koju čine: 6-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-on; 6-{4-[(S)-2-metil-3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; i 6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; ili stereoizomerni oblik, mješavina stereoizomernih oblika ili farmaceutski prihvatljiva sol istih.
29. Spoj prema patentnom zahtjevu 28, naznačen time da je spoj odabran iz skupine koju čine: 6-{4-[(S)-2-metil-3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; i 6-{4-[3-((R)'2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-on; ili stereoizomerni oblik, mješavina stereoizomernih oblika ili farmaceutski prihvatljiva sol istih;
30. Spoj prema patentnom zahtjevu 29, naznačen time da spoj predstavlja 6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]- fenil}-2H-piridazin-3-on ili stereoizomerni oblik, mješavinu stereoizomernih oblika ili farmaceutski prihvatljivu sol istog;
31. Farmaceutski sastav, naznačen time da sadrži spoj patentnog zahtjeva 1 ili stereoizomerni oblik, mješavinu stereoizomernih oblika ili farmaceutski prihvatljivu sol istog ijedan ili više farmaceutski prihvatljivih ekscipijensa.
32. Spoj prema patentnom zahtjevu 1 ili stereoizomerni oblik, mješavina stereoizomernih oblika ili farmaceutski prihvatljiva sol istog, naznačen time da je za upotrebu u liječenju poremećaja odabranog iz skupine koju čine narkolepsija ili poremećaj spavanja/buđenja, hranidbeno ponašanje, poremećaji ishrane, gojaznost, kognicija, napetost, pamćenje, poremećaji raspoloženja, promjena pažnje, poremećaj pažnje i hiperaktivnost (ADHD), Alzheimerova bolest/demencija, šizofrenija, bol, stres, migrena, mučnina u toku vožnje, depresija, psihijatrijski poremećaji, epilepsija, gastrointestinalni poremećaji, respiratorni poremećaji, upala i infarkt miokarda.
33. Spoj prema patentnom zahtjevu 1 koji ima strukturu: [image] ili stereoizomerni oblik, mješavinu stereoizomernih oblika ili farmaceutski prihvatljivu sol istog, naznačen time da X i Xa predstavljaju svaki nezavisno CH ili N; Y je odabran od S(O)q, O i NR15; R predstavlja piperidinski ili pirolidinski prsten opcionalno supstituiran 1 do 3 R20 skupinama; R2 predstavlja [image] gdje: R2je u para poziciji u odnosu na Y-(CHR4)m-R1 skupinu; R3 pri svakom pojavljivanju predstavlja nezavisno H, F, Cl, Br, I, OR21, NR23R24, NO2, CN, CF3, (C1-C6)alkil, C(=O)R21, CO2R2 ili C(=O)NR23R24; ili kada je R3 u orto poziciji u odnosu na R2, tada se R3 i R14 mogu kombinirati kako bi formirali -(CH2)S-, -CH2Z-, CH2CH2Z-; gdje Z predstavlja O, S(O)y ili NR^; R4predstavlja H, (C1-C6)alkil ili OR21, gdje alkilnu skupinu opcionalno supstituiraju 1 do 3 R20 skupine; R12 predstavlja H, (C1-C6)alkil, cikloalkil, aril, arilalkil, heteroaril, heterocikloalkil, C(=O)R27 ili CO2R27, gdje alkil, cikloalkil, aril, arilalkil, heteroaril ili heterocikloalkilnu skupinu opcionalno supstituiraju 1 do 3 R20 skupine; R13 i R14 predstavljaju nezavisno H, (C1-C6)alkil, aril ili arilalkil ili se R13 i R14 mogu kombinirati kako bi formirali fuzionirani fenilni, tienilni, pirolilni, ciklopentilni ili cikloheksilni prsten; gdje fenilne, tienilne, pirolilne, ciklopentilne ili cikloheksilne prstene opcionalno supstituiraju 1 do 3 R20 skupine; R15 predstavlja H, (C1-C6)alkil, C(=O)R25, CO2R25; R20 pri svakom pojavljivanju predstavlja nezavisno H, F, Cl, Br, I, OR21, OR22, NR23R24, NHOH, NO2, CN, CF3, (C1-C6)alkil opcionalno supstituiran OR26, (C2-C6)alkenilom, (C2-C6)alkinilom, (C3-C7)cikloalkilom, 3- do 7-članim heterocikloalkilom, fenilom, 5- ili 6-članim heteroarilom, arilalkilom (=O), C(=O)R21, CO2R21, OC(=O)R21, C(=O)NR23R24, NR27C(=O)R21, NR27C(=O)OR21, OC(=O)NR23R24, NR27C(=S)R21 ili S(O)qR21; R21 pri svakom pojavljivanju predstavlja nezavisno H, (C1-C6)alkil, aril ili arilalkil; R22 pri svakom pojavljivanju predstavlja nezavisno ostatak amino kiseline nastao nakon uklanjanja hidroksilne skupine iz karboksilne skupine; R23 i R24pri svakom pojavljivanju svaki su nezavisno odabrani od H, (C1-C6)alkila i arila, ili R23 i R24, zajedno s atomom dušika za koji su vezani, formiraju 3-7-člani heterociklični prsten opcionalno supstituiran s =O; R25 predstavlja (C1-C6)alkil, aril ili alkilaril; R26 predstavlja H, (C1-C6)alkil, aril ili alkilaril; R27 predstavlja H ili (C1-C6)alkil; m predstavlja 1, 2, 3, 4 ili 5 kada je R1 vezan preko atoma dušika, a m predstavlja 0, 1, 2, 3, 4 ili 5 kada je R1 vezan preko atoma ugljika; n predstavlja 0, 1, 2 ili 3; q predstavlja 0, 1 ili 2; i s predstavlja 1, 2 ili 3.
34. Spoj prema patentnom zahtjevu 33, naznačen time da je spoj odabran od: 2-metil-6-{4-[3-{(R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-ona; 2-metil-6-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-ona; 2-izopropil-6-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-ona; 2-izopropil-6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-ona; 2-etil-6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-ona; 6-{3-fluoro-4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2-metil-2H-piridazin-3-ona; 2-(3,5-dikloro-fenil)-6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-ona; 6-[3-fluoro-4-(3-piperidin-1-il-propoksi)-fenil]-2-fenil-2H-piridazin-3-ona; 6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil} -2H-piridazin-3-ona; 4-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2,5,6,7-tetrahidro-ciklopenta[d]piridazin-1-ona; 2-metil-6-{4-[(S)-2-metil-3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-ona; 6-{4-[3-((S)-2-hidroksimetil-pirolidin-1-il)-propoksi]-fenil}-2-metil-2H-piridazin-3-ona; 6-{4-[3-((R)-2-hidroksimetil-pirolidin-1-il)-propoksi]-fenil}-2-metil-2H-piridazin-3-ona; 2-benzil-{6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-ona; 6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2-fenil-2H-piridazin-3-ona; 5-lzopropil-7-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-5H-tieno[2,3-d]piridazin-4-ona; 7-{4-[3-(2,5-dimetil-pirolidin-1-il)-propoksi]-fenil}-5-izopropil-5H-tieno[2,3-d]piridazin-4-ona; 5-izopropil-7-[4-(3-piperidin-1-il-propoksi)-fenil]-5H-tieno[2,3-d]piridazin-4-ona; 7-{4-[3-(3,3-dimetil-piperidin-1-il)-propoksi]-fenil}-5-izopropil-5H-tieno[2,3-d]piridazin-4-ona; 5-izopropil-7-{4-[3-((S)-2-metoksimetil-pirolidin-1-il)-propoksi]-fenil}-5H-tieno[2,3-d]piridazin-4-ona; 5-izopropil-7-{4-[3-((R)-2-metoksimetil-pirolidin-1-il)-propoksi]-fenil)-5H-tieno[2,3-d]piridazin-4-ona; 5-izopropil-7-[4-(3-pirolidin-1-il-propoksi)-fenil]-5H-tieno[2,3-d]-piridazin-4-ona; 5-izopropil-7-{4-[3-(4-pirolidin-1-il-piperidin-1-il)-propoksi]-fenil}-5H-tieno[2,3-d]piridazin-4-ona; 7-{4-[3-((2R,SR)-2,5-dimetil-pirolidin-1-il)-propoksi]-fenil}-5-izopropil-5H-tieno[2,3-d]piridazin-4-ona; 7-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-5-propil-5H-tieno[2,3-d]piridazin-4-ona; 7-{4-[3-((2R,SR)-2,5-dimetil-pirolidin-1-il)-propoksi]-fenil}-5-propil-5H-tieno[2,3-d]piridazin-4-ona; 7-{4-[3-(4-metil-piperidin-1-il)-propoksi]-fenil}-5-propil-5H-tieno[2,3-d]piridazin-4-ona; 7-{4-[3-(4-dimetilamino-piperidin-1-il)-propoksi]-fenil}-5-propil-5H-tieno[2,3-d]piridazin-4-ona; 5-propil-7-{4-[3-((S)-2-pirolidin-1-ilmetil-pirolidin-1-il)-propoksi]-fenil}-5H-tieno[2,3-d]piridazin4-ona; 5-(4-kloro-benzil)-7-[4-(3-piperidin-1-il-propoksi)-fenil]-5H-tieno[2,3-d]piridazin-4-ona; 5-(4-kloro-benzil)-7-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-5H-tieno[2,3-d]piridazin-4-ona; 2,4-dimetil-6-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-ona; 2,4-dimetil-6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-ona; 2-izopropil-4-metil-6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-ona; 2-izopropil-4-metil-6-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-ona; 2-benzil-4-metil-6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-ona; 2-benzil-4-metil-6-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-ona; 4-benzil-2-metil-6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-ona; 4-benzil-2-metil-6-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-ona; 2-metil-6-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-5-feni-2H-piridazin-3-ona; 2-metil-5-fenil-6-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-piridazin-3-ona; 2-metil-4-{4-[3-((R)-2-metil-pirolidin-1-ii)-propoksi]-fenil}-2H-ftalazin-1-ona; 2-metil-4-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-ftalazin-1-ona; 2-metil-4-[4-(2-piperidin-1-il-etoksi)-fenil]-2H-ftalazin-1-ona; 2-metil-4-[4-(3-pirolidin-1-il-propoksi)-fenil]-2H-ftalazin-1-ona; 2-(4-kloro-benzil)-4-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-ftalazin-1-ona; 2-(4-kloro-benzil)-4-[4-(3-piperidin-1-il-propoksi)-fenil]-2H-ftalazin-1-ona; 2-metil-4-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2,5,6,7-tetrahidro-ciklopenta[d]piridazin-1-ona; 2-metil-4-[4-(3-piperidin-1-il-propoksi)-fenil]-2,5,6,7-tetrahidro-ciklopenta[d]piridazin-1-ona; 2-metil-4-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-5,6,7,8-tetrahidro-2H-ftalazin-1-ona; 4-{4-[3-(butil-etil-amino)-propoksi]-fenil}-2-metil-5,6,7,8-tetrahidro-2H-fialazin-1-ona; tert-butil estera 4- 4-(3-metil-4-okso-3,4-dihidro-ftalazin-1-il)-fenoksimetil]-piperidin-1-karboksilne kiseline; 2-metil-4-[4-(piperidin-4-il-metoksi)-fenil]-2H-ftalazin-1-ona; 4-[4-(1-ciklobutil-piperidin-4-il-metoksi)-fenil]-2-metil-2H-ftalazin-1-ona; tert-butil estera 4-[4-(1-metil-6-okso-1,6-dihidro-piridazin-3-il)-fenoksimetil]-piperidin-1-karboksilne kiseline; 2-metil-6-[4-(piperidin-4-il-metoksi)-fenil]-2H-piridazin-3-ona; 6-[4-(1-ciklobutil-piperidin-4-il-metoksi)-fenil]-2-metil-2H-piridazin-3-ona; 6-[4-(1-izopropil-piperidin-4-il-metoksi)-fenil]-2-metil-2H-piridazin-3-ona; 6-[4-(1-ciklopropilmetil-piperidin-4-il-metoksi)-fenil]-2-metil-2H-piridazin-3-ona; 6-[4-(1-ciklopentil-piperidin-4-il-metoksi)-fenil]-2-metil-2H-piridazin-3-ona; 2-metil-6-[4-(1-metil-piperidin-4-il-metoksi)-fenil]-2H-piridazin-3-ona; 6-[4-(1-izopropil-piperidin-4-iloksi)-fenil]-2-metil-2H-piridazin-3-ona; 2-metil-6-[4-(piperidin-4-iloksi)-fenil]-2H-piridazin-3-ona; 2-metil-6-[4-(piperidin-4-iloksi)-fenil]-2H-piridazin-3-ona; 6-3-fluoro-4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil-2-fenil-2H-piridazin-3-ona; 2-{4-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-fenil}-2H-piridazin-3-ona; 8-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-5,6-dihidro-2H-benzo[h]kinolin-3-ona; 8-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-5,6-dihidro-3H-benzo[f]kinolin-2-ona; 2-metil-8-[3-((R)-2-metil-pirolidin-1-il)-propoksil-5,6-dihidro-2H-benzo[h]kinolin-3-ona; 8-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-2-fenil-5,6-dihidro-2H-benzo [h]kinolin-3-ona; 2-benzil-8-(3-piperidin-1-il-propoksi)-5,6-dihidro-2H-benzo[h]kinolin-3-ona; 2-izopropil-8-(3-piperidin-1-il-propoksi)-5,6-dihidro-2H-benzo[h]kinolin-3-ona; 2-metil-7-[3-((R)-2-metil-pirolidin-1-il)-propoksi]-2H-ftalazin-1-ona; i 2-metil-7-(3-piperidin-1-il-propoksi)-2H-ftalazin-1-ona; ili stereoizomernog oblika, mješavine stereoizomernih oblika ili farmaceutski prihvatljive soli istih;
35. Spoj prema patentnom zahtjevu 1, naznačen time da R2 predstavlja (i) ili (iv).
36. Spoj prema patentnom zahtjevu 35, naznačen time da R2 predstavlja (iv).
37. Spoj prema patentnom zahtjevu 36, naznačen time da R2 predstavlja (iv), R12 predstavlja H ili heteroaril, i R13 i R14 svaki predstavlja H ili alkilnu skupinu.
38. Spoj prema patentnom zahtjevu 37, naznačen time da R2 predstavlja (iv), R12 predstavlja heteroaril, i R13 i R14 svaki predstavlja H ili alkilnu skupinu.
39. Spoj prema patentnom zahtjevu 4, naznačen time da R2 predstavlja (iii) i jedan od R 3 predstavlja ciklopropil.
40. Spoj prema patentnom zahtjevu 36, naznačen time da R2 predstavlja: [image] i R12 predstavlja (C1-C6)alkil, aril, arilalkil ili heteroaril.
41. Spoj prema patentnom zahtjevu 40, naznačen time da R12 predstavlja tienil ili piridinil.
42. Spoj prema patentnom zahtjevu 41, naznačen time da R12 predstavlja piridin-2-il.
43. Farmaceutski sastav, naznačen time da sadrži spoj patentnog zahtjeva 33 i jedan ili više farmaceutski prihvatljivih ekscipijensa.
44. Spoj, stereoizomerni oblik, mješavina stereoizomernih oblika ili farmaceutski prihvatljiva sol istog prema patentnom zahtjevu 33, naznačen time da je za upotrebu u liječenju poremećaja odabranih iz skupine koju čine narkolepsija ili poremećaj spavanja/buđenja, hranidbeno ponašanje, poremećaj ishrane, gojaznost, kognicija, napetost, pamćenje, poremećaji raspoloženja, promjena pažnje, poremećaj pažnje i hiperaktivnost (ADHD), Alzheimerova bolest/demencija, šizofrenija, bol, stres, migrena, mučnina u toku vožnje, depresija, psihijatrijski poremećaji, epilepsija, gastrointestinalni poremećaji, respiratorni poremećaji, upala i infarkt miokarda.
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Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008137087A1 (en) 2007-05-03 2008-11-13 Cephalon, Inc. Processes for preparing (r)-2-methylpyrrolidine and (s)-2-methylpyrrolidine and tartrate salts thereof
US5241062A (en) * 1993-01-19 1993-08-31 Sun Company, Inc. (R&M) Synthetic route to meso-tetra hydrocarbyl or substituted hydrocarbyl porphyrins and derivatives
US9108948B2 (en) * 2006-06-23 2015-08-18 Abbvie Inc. Cyclopropyl amine derivatives
AU2007260836B2 (en) * 2006-06-23 2012-11-15 Abbvie Bahamas Ltd. Cyclopropyl amine derivatives as histamin H3 receptor modulators
MX2009000884A (es) 2006-07-25 2009-06-05 Cephalon Inc Derivados de piridizinona.
CL2008000066A1 (es) 2007-01-12 2008-08-01 Smithkline Beecham Corp Compuestos derivados de (5-hidroxi-3-oxo-2,3-dihidropiridazina-4-carbonil)glicina, inhibidores de hif prolil hidroxilasas; procedimiento de preparacion; composicion farmaceutica que comprende a dichos compuestos; y su uso en el tratamiento de la anem
US8283351B2 (en) * 2007-04-02 2012-10-09 Institute For Oneworld Health Cyclic and acyclic hydrazine derivatives compositions including them and uses thereof
DE102007025717A1 (de) * 2007-06-01 2008-12-11 Merck Patent Gmbh Arylether-pyridazinonderivate
US20090221648A1 (en) * 2007-12-21 2009-09-03 Abbott Laboratories Compositions for treatment of cognitive disorders
US8383657B2 (en) * 2007-12-21 2013-02-26 Abbott Laboratories Thiazolylidine urea and amide derivatives and methods of use thereof
MX2010008384A (es) * 2008-01-30 2010-11-30 Cephalon Inc Derivados de piridazina substituida, con actividad antagonista de h3 de histamina.
EP2328586A2 (en) * 2008-05-20 2011-06-08 Cephalon, Inc. Substituted pyridazinone derivatives as histamine-3 (h3) receptor ligands
CA2726588C (en) 2008-06-03 2019-04-16 Karl Kossen Compounds and methods for treating inflammatory and fibrotic disorders
GB0817207D0 (en) * 2008-09-19 2008-10-29 Pimco 2664 Ltd therapeutic apsac compounds and their use
US9186353B2 (en) * 2009-04-27 2015-11-17 Abbvie Inc. Treatment of osteoarthritis pain
EP2459529A1 (en) * 2009-07-02 2012-06-06 Cephalon, Inc. Substituted phenoxypropylcycloamine derivatives as histamine-3 (h3) receptor ligands
WO2012032532A1 (en) * 2010-09-07 2012-03-15 Symed Labs Limited "processes for the preparation of 4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone and intermediates thereof"
US8853390B2 (en) 2010-09-16 2014-10-07 Abbvie Inc. Processes for preparing 1,2-substituted cyclopropyl derivatives
KR101303283B1 (ko) * 2011-03-28 2013-09-04 한국화학연구원 피리다지논 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 포함하는 약학적 조성물
WO2013097052A1 (en) 2011-12-30 2013-07-04 Abbott Laboratories Bromodomain inhibitors
CN104718201A (zh) * 2012-06-12 2015-06-17 艾伯维公司 吡啶酮和哒嗪酮衍生物
AR092742A1 (es) 2012-10-02 2015-04-29 Intermune Inc Piridinonas antifibroticas
EP2970145B1 (en) * 2013-03-11 2020-05-06 The Broad Institute, Inc. Compounds and compositions for the treatment of cancer
JP6417401B2 (ja) 2013-05-10 2018-11-07 ギリアド アポロ， エルエルシー Ａｃｃ阻害剤及びその使用
EA030942B1 (ru) 2013-05-10 2018-10-31 Джилид Аполло, Ллс Ингибиторы акк и их применение
JP6417402B2 (ja) * 2013-05-10 2018-11-07 ギリアド アポロ， エルエルシー Ａｃｃ阻害剤及びその使用
BR112015028214A2 (pt) 2013-05-10 2017-07-25 Nimbus Apollo Inc inibidores de acc e usos dos mesmos
CN103772352B (zh) * 2014-01-16 2017-01-18 四川百利药业有限责任公司 哒嗪酮类衍生物及其制备方法和用途
WO2015153683A1 (en) 2014-04-02 2015-10-08 Intermune, Inc. Anti-fibrotic pyridinones
ES2821049T3 (es) 2015-06-18 2021-04-23 89Bio Ltd Derivados de piperidina 1,4 sustituidos
CA3014432A1 (en) 2015-06-18 2016-12-22 Cephalon, Inc. Substituted 4-benzyl and 4-benzoyl piperidine derivatives
PL3438095T3 (pl) 2016-03-30 2021-11-29 Ishihara Sangyo Kaisha, Ltd. Związek pirydazynonowy lub jego sól, oraz zawierający go środek chwastobójczy
PL3442972T3 (pl) 2016-04-15 2020-07-27 Abbvie Inc. Inhibitory bromodomeny
US10995084B2 (en) 2016-07-22 2021-05-04 Kissei Pharmaceutical Co., Ltd. Pyrrolidine derivative
WO2018086703A1 (en) 2016-11-11 2018-05-17 Bayer Pharma Aktiengesellschaft Dihydropyridazinones substituted with phenylureas
CN109111400B (zh) * 2017-06-23 2020-10-16 杭州百诚医药科技股份有限公司 苯基喹啉酮类和黄酮类衍生物的制备和应用
CA3075727A1 (en) * 2017-09-18 2019-03-21 Goldfinch Bio, Inc. Pyridazinones and methods of use thereof
CN108264488A (zh) * 2018-01-26 2018-07-10 天津瑞岭化工有限公司 一种取代2,3-二氮杂萘酮类化合物的制备方法
JP2021512103A (ja) 2018-01-31 2021-05-13 バイエル アクチェンゲゼルシャフトＢａｙｅｒ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ Ｎａｍｐｔ阻害剤を含む抗体薬物複合体（ａｄｃｓ）
HRP20230458T1 (hr) 2018-04-30 2023-07-21 Ribon Therapeutics Inc. Piridazinoni kao inhibitori parp7
KR20210069652A (ko) 2018-09-18 2021-06-11 골드핀치 바이오 인코포레이티드 피리다지논 및 이의 사용 방법
EA202191890A1 (ru) 2019-01-18 2022-02-03 Астразенека Аб Ингибиторы pcsk9 и способы их применения
WO2020157199A1 (en) 2019-02-01 2020-08-06 Bayer Aktiengesellschaft Annulated dihydropyridazinone compounds as anti-cancer compounds
US20220162196A1 (en) * 2019-04-29 2022-05-26 Ribon Therapeutics, Inc. Solid forms of a parp7 inhibitor
WO2021013693A1 (en) 2019-07-23 2021-01-28 Bayer Pharma Aktiengesellschaft Antibody drug conjugates (adcs) with nampt inhibitors
US11691969B2 (en) 2019-10-30 2023-07-04 Ribon Therapeutics, Inc. Pyridazinones as PARP7 inhibtors
GB201917101D0 (en) 2019-11-25 2020-01-08 Uea Enterprises Ltd Method for digesting nucleic acid in a sample
WO2022113008A1 (en) 2020-11-27 2022-06-02 Richter Gedeon Nyrt. Histamine h3 receptor antagonists/inverse agonists for the treatment of autism spectrum disorder
WO2022156708A1 (en) * 2021-01-20 2022-07-28 Jacobio Pharmaceuticals Co., Ltd. Parp7 enzyme inhibitor
CN114560814B (zh) * 2022-03-02 2023-10-20 天津理工大学 一种取代2,3-二氮杂萘酮类化合物的合成方法

Family Cites Families (90)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4011321A (en) 1973-12-19 1977-03-08 Smith Kline & French Laboratories Limited Pharmaceutical compositions and methods of inhibiting β-adrenergic receptors
GB1488330A (en) 1973-12-19 1977-10-12 Smith Kline French Lab Dihydropyridazinones
US4111936A (en) 1974-06-18 1978-09-05 Smith Kline & French Laboratories Limited Pyridazinethiones
IE42214B1 (en) 1974-06-18 1980-07-02 Smith Kline French Lab Hydrazinopyredazines
US4111935A (en) 1975-01-02 1978-09-05 Smith Kline & French Laboratories Limited 3-chloro-6-phenylpyridazine compounds
US4082843A (en) 1975-11-26 1978-04-04 Smith Kline & French Laboratories Limited 3-(3-(3-Substituted amino-2-hydroxypropoxy)phenyl)-6-hydrazino pyridazines and their use as vasodilators and β-adrenergic blocking agents
BE836633A (fr) 1975-12-15 1976-06-15 Phenylhydrazinopyridazines
GB1548601A (en) 1976-03-29 1979-07-18 Smith Kline French Lab Pyridazines
JPS5746966A (en) 1980-09-03 1982-03-17 Mitsui Toatsu Chem Inc Pyridazinone derivative and its production
EP0051217A1 (en) 1980-10-31 1982-05-12 Usv Pharmaceutical Corporation Oxidation process
US4331600A (en) 1980-10-31 1982-05-25 Usv Pharmaceutical Corporation Intermediates for the synthesis of phthalimidines
US4397854A (en) 1981-05-14 1983-08-09 Warner-Lambert Company Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents
US4404203A (en) 1981-05-14 1983-09-13 Warner-Lambert Company Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents
HU190412B (en) 1981-09-17 1986-09-29 Warner-Lambert Co,Us Process for producing substituted 4,5-dihiydro-6-bracket-substituted-bracket closed-phenyl-3-bracket-2h-bracket closed-pyridazinones and 6-bracket-substituted-bracket closed-phenyl-3-bracket-2h-bracket closed-pyridazinones
US4353905A (en) 1981-09-17 1982-10-12 Warner-Lambert Company Substituted 4,5-dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones and 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones
JPS58113180A (ja) 1981-12-28 1983-07-05 Mitsui Toatsu Chem Inc ピリダジノン誘導体
US4734415A (en) 1982-08-13 1988-03-29 Warner-Lambert Company Substituted 4,5-dihydro-6-(substituted)-phenyl-3(2H)-pyridazinones and 6-(substituted) phenyl-3(2H)-pyridazinones
US4666902A (en) 1983-06-20 1987-05-19 Cassella Aktiengesellschaft Tetrahydropyridazinone derivatives, processes for their preparation and their use
GB8323553D0 (en) 1983-09-02 1983-10-05 Smith Kline French Lab Pharmaceutical compositions
JPS6087283A (ja) * 1983-10-19 1985-05-16 Mitsubishi Chem Ind Ltd ピリダジノン誘導体またはその塩類
US4816454A (en) 1984-09-21 1989-03-28 Cassella Aktiengesellschaft 4,5-dihydro-3(2H)-pyridazinones and their pharmacological use
EP0194548A3 (de) 1985-03-12 1988-08-17 Dr. Karl Thomae GmbH Neue Sulfonylaminoäthylverbindungen, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
AU5428686A (en) 1985-03-12 1986-09-18 Smith Kline & French Laboratories Limited Imidazolinone and thiazolinone derivatives
GB8506319D0 (en) 1985-03-12 1985-04-11 Smith Kline French Lab Chemical compounds
GB8528633D0 (en) 1985-11-21 1985-12-24 Beecham Group Plc Compounds
JPH0629254B2 (ja) 1986-09-08 1994-04-20 帝国臓器製薬株式会社 ピリダジノン誘導体
JPS63145272A (ja) 1986-12-09 1988-06-17 Morishita Seiyaku Kk ４，５−ジヒドロ−６−（４−置換フエニル）−３（２ｈ）−ピリダジノン誘導体
JPS63154673A (ja) 1986-12-17 1988-06-27 Mitsubishi Kasei Corp ピリタジノン誘導体又はその塩類
US4819929A (en) 1987-02-24 1989-04-11 Stobb, Inc. Apparatus and method for feeding sheets to a sheet gatherer
DE3706427A1 (de) 1987-02-27 1988-09-08 Boehringer Mannheim Gmbh Neue substituierte 3h-indole, zwischenprodukte, verfahren zu ihrer herstellung sowie arzneimittel
JPS63215672A (ja) 1987-03-04 1988-09-08 Mitsubishi Kasei Corp ピリダジノン誘導体又はその塩類
DE3728491A1 (de) * 1987-08-26 1989-03-09 Heumann Pharma Gmbh & Co Dihydropyridazinon-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3804490A1 (de) 1988-02-12 1989-08-24 Heumann Pharma Gmbh & Co Substituierte 6-phenyldihydro-3(2h)-pyridazinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3814057A1 (de) 1988-04-26 1989-11-09 Heumann Pharma Gmbh & Co 6-oxo-pyridazinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3826855A1 (de) 1988-08-06 1990-02-15 Cassella Ag 4,5-dihydro-3(2h)-pyridazinone, verfahren zu ihrer herstellung und ihre verwendung
GB8903130D0 (en) 1989-02-11 1989-03-30 Orion Yhtymae Oy Substituted pyridazinones
DE3934436A1 (de) 1989-06-01 1991-04-18 Thomae Gmbh Dr K 2-hydroxy-n-propylamine, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
US5204463A (en) 1989-08-10 1993-04-20 Glaxo Inc. Substituted methoxyphenyl-4,5 dihydro-3(2H)-pridazinones having cardiotonic and beta blocking activities
EP0412814A3 (en) * 1989-08-10 1991-07-24 Glaxo Inc. Pyridazinones having cardiotonic and beta blocking activity
US5053338A (en) 1989-09-01 1991-10-01 Glaxo Inc. Kinetic resolution of pyridazinones using lipase
WO2008137087A1 (en) 2007-05-03 2008-11-13 Cephalon, Inc. Processes for preparing (r)-2-methylpyrrolidine and (s)-2-methylpyrrolidine and tartrate salts thereof
US5531496A (en) * 1994-07-28 1996-07-02 Saturn Corporation Automotive glass enclosure retaining fixture
IL118631A (en) * 1995-06-27 2002-05-23 Tanabe Seiyaku Co History of pyridazinone and processes for their preparation
JP3060454B2 (ja) 1996-12-26 2000-07-10 田辺製薬株式会社 医薬組成物
AU1760399A (en) 1997-12-15 1999-07-05 Byk Gulden Lomberg Chemische Fabrik Gmbh New phthalazinones
US6255303B1 (en) 1998-03-14 2001-07-03 Byk Gulden Lomberg Chemische Fabrik Gmbh Phthalazinone PDE III/IV inhibitors
AU6005999A (en) 1998-10-09 2000-05-01 Nihon Nohyaku Co., Ltd. Pyridazinone derivatives
AU3076700A (en) 1999-01-26 2000-08-18 Ono Pharmaceutical Co. Ltd. 2h-phthalazin-1-one derivatives and drugs comprising these derivatives as the active ingredient
DE19918294A1 (de) 1999-04-22 2000-10-26 Bayer Ag O-Aryldithiazoldioxide
DE10010425A1 (de) 2000-03-03 2001-09-06 Bayer Ag Substituierte 5-Methyldihydropyridazinone und ihre Verwendung
FI20000577A0 (fi) 2000-03-13 2000-03-13 Orion Yhtymae Oy Pyridatsinyylifenyylihydratsoneja
GB0008264D0 (en) * 2000-04-04 2000-05-24 Smithkline Beecham Plc Novel method and compounds
AU8112101A (en) 2000-08-08 2002-02-18 Ortho Mcneil Pharm Inc Non-imidazole aryloxypiperidines
BR0114836A (pt) 2000-10-20 2003-07-01 Pfizer Prod Inc Agonistas de receptores beta-3 adrenérgicos e suas aplicações
JP2005520791A (ja) 2001-11-08 2005-07-14 イーラン ファーマスーティカルズ、インコーポレイテッド Ｎ，ｎ’−置換−１，３−ジアミノ−２−ヒドロキシプロパン誘導体
US20040067955A1 (en) 2002-09-06 2004-04-08 Fujisawa Pharmaceutical Co. Ltd. Pyridazinone compound and pharmaceutical use thereof
GB0308333D0 (en) 2003-04-10 2003-05-14 Glaxo Group Ltd Novel compounds
JP4735261B2 (ja) 2003-06-27 2011-07-27 Ｍｓｄ株式会社 ヘテロアリールオキシ含窒素飽和ヘテロ環誘導体
DE102004010194A1 (de) 2004-03-02 2005-10-13 Aventis Pharma Deutschland Gmbh 4-Benzimidazol-2-yl-pyridazin-3-on-Derivate, ihre Herstellung und Verwendung in Arzneimitteln
DE102004010207A1 (de) * 2004-03-02 2005-09-15 Aventis Pharma S.A. Neue 4-Benzimidazol-2-yl-pyridazin-3-on-Derivate
WO2006060127A2 (en) 2004-11-30 2006-06-08 Artesian Therapeutics, Inc. COMPOUNDS WITH MIXED PDE-INHIBITORY AND β-ADRENERGIC ANTAGONIST OR PARTIAL AGONIST ACTIVITY FOR TREATMENT OF HEART FAILURE
JP2008521805A (ja) 2004-11-30 2008-06-26 アーテシアン セラピューティクス， インコーポレイテッド β−アドレナリン作用性受容体およびホスホジエステラーゼに対する阻害活性を有する強心性化合物
AU2006228690A1 (en) 2005-03-31 2006-10-05 Ucb Pharma S.A. Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses
EP1707203A1 (en) 2005-04-01 2006-10-04 Bioprojet Treatment of parkinson's disease obstructive sleep apnea, dementia with lewy bodies, vascular dementia with non-imidazole alkylamines histamine H3- receptor ligands
EP1717235A3 (en) 2005-04-29 2007-02-28 Bioprojet Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands
WO2006124874A2 (en) * 2005-05-12 2006-11-23 Kalypsys, Inc. Inhibitors of b-raf kinase
DE102005057924A1 (de) 2005-12-05 2007-06-06 Merck Patent Gmbh Pyridazinonderivate
WO2007130383A2 (en) 2006-04-28 2007-11-15 Northwestern University Compositions and treatments using pyridazine compounds and secretases
MX2009000884A (es) 2006-07-25 2009-06-05 Cephalon Inc Derivados de piridizinona.
DE102006037478A1 (de) 2006-08-10 2008-02-14 Merck Patent Gmbh 2-(Heterocyclylbenzyl)-pyridazinonderivate
JP2010013354A (ja) 2006-09-07 2010-01-21 Kyorin Pharmaceut Co Ltd ２−アルキル−６−（ピラゾロピリジン−４−イル）ピリダジノン誘導体とその付加塩及びそれらを有効成分とするｐｄｅ阻害剤
US20080262226A1 (en) 2006-11-07 2008-10-23 Artesian Therapeutics, Inc. Methods of making compounds having a beta-adrenergic inhibitor and a linker and methods of making compounds having a beta-adrenergic inhibitor, a linker and a phosphodiesterase inhibitor
BRPI0718874A2 (pt) 2006-12-22 2015-06-23 Novartis Ag Compostos orgânicos
JP2008222580A (ja) 2007-03-09 2008-09-25 Kyorin Pharmaceut Co Ltd ２−置換−５−（ピラゾロピリジン−４−イル）ピラゾロン誘導体及びそれらを有効成分とするホスホジエステラーゼ阻害剤
JP2008222648A (ja) 2007-03-14 2008-09-25 Kyorin Pharmaceut Co Ltd ２−置換−５−（ピラゾロピリジン−３−イル）ピラゾロン誘導体とその付加塩及びそれらを有効成分とするｐｄｅ阻害剤
JP2008239558A (ja) 2007-03-28 2008-10-09 Kyorin Pharmaceut Co Ltd ２−置換−６−（ピラゾロピリジン−３−イル）ピリダジノン誘導体とその付加塩及びそれらを有効成分とするｐｄｅ阻害剤
US7867980B2 (en) 2007-05-31 2011-01-11 Meiji Seika Kaisha, Ltd. Lincosamide derivatives and antimicrobial agents comprising the same as active ingredient
DE102007025717A1 (de) 2007-06-01 2008-12-11 Merck Patent Gmbh Arylether-pyridazinonderivate
US20100130738A1 (en) 2007-06-19 2010-05-27 Yasushi Kohno Pyrazolone derivative and pde inhibitor containing the same as active ingredient
US20100160335A1 (en) 2007-06-19 2010-06-24 Kyorin Pharmaceutical Co., Ltd. Pyridazinone derivative and pde inhibitor containing the same as active ingredient
US20090011994A1 (en) 2007-07-06 2009-01-08 Bristol-Myers Squibb Company Non-basic melanin concentrating hormone receptor-1 antagonists and methods
CN101842359A (zh) * 2007-10-31 2010-09-22 日产化学工业株式会社 哒嗪酮化合物和p2x7受体抑制剂
EP2219646A4 (en) 2007-12-21 2010-12-22 Univ Rochester METHOD FOR MODIFYING THE LIFETIME OF EUKARYOTIC ORGANISMS
WO2009082698A1 (en) 2007-12-21 2009-07-02 Abbott Laboratories Compositions for treatment of cognitive disorders
CA2712897A1 (en) 2008-01-30 2009-08-06 Pharmacopeia, Inc. Substituted spirocyclic piperidine derivatives as histamine-3 (h3) receptor ligands
MX2010008382A (es) 2008-01-30 2010-11-25 Cephalon Inc Derivados de piperidina espirociclicos substituidos, como ligandos de receptores de histamina-3 (h3).
MX2010008384A (es) 2008-01-30 2010-11-30 Cephalon Inc Derivados de piridazina substituida, con actividad antagonista de h3 de histamina.
EP2328586A2 (en) 2008-05-20 2011-06-08 Cephalon, Inc. Substituted pyridazinone derivatives as histamine-3 (h3) receptor ligands
EP2396408B1 (en) * 2009-02-12 2017-09-20 CuRNA, Inc. Treatment of glial cell derived neurotrophic factor (gdnf) related diseases by inhibition of natural antisense transcript to gdnf
US9186353B2 (en) 2009-04-27 2015-11-17 Abbvie Inc. Treatment of osteoarthritis pain

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