HRP20150096T1 - 2-aminobenzimidazol-5-karboksamidi kao protuupalni agensi - Google Patents

2-aminobenzimidazol-5-karboksamidi kao protuupalni agensi Download PDF

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HRP20150096T1
HRP20150096T1 HRP20150096AT HRP20150096T HRP20150096T1 HR P20150096 T1 HRP20150096 T1 HR P20150096T1 HR P20150096A T HRP20150096A T HR P20150096AT HR P20150096 T HRP20150096 T HR P20150096T HR P20150096 T1 HRP20150096 T1 HR P20150096T1
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Roland Pfau
Kirsten Arndt
Henri Doods
Klaus Klinder
Raimund Kuelzer
Dimitrijs Lubriks
Juergen Mack
Benjamin Pelcman
Henning Priepke
Robert Roenn
Dirk Stenkamp
Edgars Suna
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Orexo Ab
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P25/00—Drugs for disorders of the nervous system
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    • A—HUMAN NECESSITIES
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    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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Claims (19)

1. Spojevi opće formule I [image] jedan od X i Y predstavlja -N(R6)-; i drugi predstavlja -N= ; jedan od Z1, Z2 i Z3 neovisno predstavlja -C(R7)= ili -N=; i druga dva od Z1, Z2 i Z3 predstavljaju -C(R7)=; Q2, Q3 i Q4 predstavljaju odgovarajući -C(R2)=, -C(R3)= i -C(R4)=; ili bilo koji ili bilo koja dva od Q2, Q3 ili Q4 mogu naizmjence i neovisno predstavljati -N=; R1 predstavlja halo, OH, -CN; C1-3 alkil, C2-6 alkinil, OC1-3 alkil, gdje su zadnje tri skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -CN, =O, OH, -OCH3, -OCF3; R2, R3 i R4 neovisno predstavljaju vodik, halo, -CN; C1-3 alkil, OC1-3 alkil, gdje su zadnje dvije skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -CN, =O, OH, -OCH3, -OCF3; Ra, Rb neovisno predstavljaju vodik, C1-3 alkil, ili oba zajedno s ugljikovim atomom na koji su vezani, čine C3-7 cikloalkilenski prsten, ili 4-6-člani heterocikloalkilenski prsten; Rc predstavlja vodik ili C1-3 alkil; W predstavlja -C(O)-, -S(O)-, -S(O)2-, -C(O)O-, ili -C(O)NRd-, gdje su skupine vezane za dušik iz -NRc- dijela preko atoma ugljika ili sumpora; Rd predstavlja vodik ili C1-3 alkil; M predstavlja C1-7 alkil, C3-7 cikloalkil, gdje su obje skupine opcionalno supstituirane s jednom ili više skupina odabranih od fluoro, -OH, -CN, -NH2, -NH(C1-3 alkil), N(C1-3 alkil)2, -OC1-3 alkil, -SC1-3 alkil, aril, heteroaril [gdje dvije zadnje skupine mogu biti supstituirane s jednim ili više supstituenata odabranih od halo, OH, -CN, C1-3 alkil, OC1-3 alkil (gdje su zadnje dvije alkilne skupine opcionalno supstituirane s jednim ili više atoma fluora)], C1-7 alkil, C2-7, alkinil, C3-7 cikloalkil-C0-2alkil, 4-7-člani heterocikloalkil-C0-2 alkil (gdje su zadnje alkil, alkinil, heterocikloalkil ili cikloalkil skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -CN, =O, -NH2, -NH(C1-3 alkil), -N(C1-3 alkil)2, -OH, -OC1-3 alkil); ili aril, heteroaril, 4-7-člani heterocikloalkil, od kojih su sve skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od halo, -OH, -CN, -NH2, -NH(C1-3 alkil), -N(C1-3 alkil)2, -OC1-3 alkil, -SC1-3 alkil, aril, heteroaril [gdje zadnje dvije skupine mogu biti supstituirane s jednim ili više supstituenata odabranih od halo, OH, -CN, C1-3 alkil, -OC1-3 alkil (gdje su dvije zadnje alkilne skupine opcionalno supstituirane s jednim ili više atoma fluora)], C1-7 alkil, C2-7 alkinil, C3-7 cikloalkil, 4-7-člani heterocikloalkil (gdje su zadnje alkil, alkinil, heterocikloalkil ili cikloalkil skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -CN, =O, -NH2, -NH(C1-3 alkil), N(C1-3 alkil)2, -OH, -OC1-3alkil)]; R5 predstavlja vodik; ili C1-3 alkil; R6 predstavlja vodik; C1-5 alkil, C3-6 alkinil, 4-7-člani heterocikloalkil-C0-2 alkil ili C3-7cikloalkil-C0-2 alkil (gdje su zadnje četiri skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -CN, =O, C1-3 alkil, -OH, -OC1-3 alkil, -NH2, -NH(C1-3 alkil), N(C1-3 alkil)2); svaki R7 neovisno predstavlja vodik, halo, -CN, C1-7 alkil, C2-7 alkinil, C3-7 cikloalkil, C1-5 alkil-O-, C3-7cikloalkil-C0-2 alkil-O-, 4-7-člani heterocikloalkil-C0-2 alkil-O-, (gdje je zadnjih šest skupina alkil, alkinil, cikloalkil ili heterocikloalkil fragmenata opcionalno supstituirano s jednim ili više supstituenata odabranih od fluoro, -CN, =O, OH, -OC1-3 alkil, -NH2, -NH-C1-3 alkil, N(C1-3 alkil)2 ili s jednim ili više C1-3 alkil skupina, koje mogu biti opcionalno supstituirane s jednim ili više atoma fluora); ili aril ili heteroaril, gdje zadnje dvije skupine mogu biti supstituirane s jednim ili više supstituenata odabranih od halo, OH, -CN, C1-3 alkil, -OC1-3 alkil (gdje su zadnje dvije skupine alkilnih fragmenata opcionalno su supstituirane s jednim ili više atoma fluora); L predstavlja -C(O)N(R8)-, -N(R8)C(O)-, -S(O)2N(R8)-, - N(R8)S(O)2-, - N(R8)C(O)N(R8)-, -OC(O)N(R8)- ili -N(R8)C(O)O-; A predstavlja vodik, C1-8 alkil, C3-8 alkinil, aril, heteroaril, aril-C1-3alkil-, C3-8cikloalkil-C0-3alkil-, 4-7-člani heterocikloalkil-C0-3alkil-, heteroaril-C1-3alkil-, gdje su skupine alkil-, alkinil-, cikloalkil- i heterocikloalkil-fragmenata opcionalno supstituirane s jednim ili više supstituenata odabranih od R9a i su aril i heteroaril fragmenti opcionalno supstituirani s jednim ili više supstituenata odabranih od R9b; ili A-1- zajedno predstavljaju jednu od slijedećih skupina [image] u kojima V predstavlja vezu, -CH2CH2-, -CH2CH2CH2-, gdje u svakoj od zadnjih skupina alkilena jedna metilenska [-(CH2)-] jedinica može opcionalno biti zamijenjena s atomom kisika, , -NH- ili-N(C1-3 alkil)- skupinom i svaka metilenska jedinica može opcionalno i neovisno biti supstituirana s jednom ili dvije od slijedećih skupina: fluoro, -CN, =O, -NH2, -NH(C1-3 alkil), N(C1-3 alkil)2, -OH, -OC1-3alkil); svaki R8 neovisno predstavlja vodik, ili C1-3 alkil; svaki R9a neovisno predstavlja fluoro, -OH, -CN, =O, -NH2, -NH(C1-3 alkil), -N(C1-3 alkil)2, -OC1-6alkil, C1-6alkil, (gdje su zadnje četiri skupine fragmenata alkila opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -CN, =O, -NH2, -NH(C1-3 alkil), N(C1-3 alkil)2, -OH, -OC1-3 alkil) ili aril, heteroaril [gdje zadnje dvije skupine mogu biti supstituirane s jednim ili više supstituenata odabranih od halo, OH, -CN, C1-3 alkil, OC1-3 alkil (gdje su dvije zadnje alkilne skupine opcionalno supstituirane s jednim ili više atoma fluora)]; svaki R9b predstavlja neovisno halo, -OH, -CN, -NH2, -NH(C1-3 alkil), -N(C1-3 alkil)2, -OC1-3 alkil , -SC1-3 alkil, aril, heteroaril [gdje dvije zadnje skupine mogu biti supstituirane s jednim ili više supstituenata odabranih od halo, OH, -CN, C1-3 alkil, OC1-3 alkil (gdje su dvije alkilne skupine opcionalno supstituirane s jednim ili više atoma fluora)], C1-7 alkil, C2-7 alkinil, C3-7 cikloalkil, 4-7-člani heterocikloalkil (gdje su zadnje alkil, alkinil, heterocikloalkil ili cikloalkil skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -CN, =O, -NH2, -NH(C1-3 alkil), N(C1-3 alkil)2, -OH, OC1-3alkil); njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama ili baza.
2. Spojevi prema zahtjevu 1, naznačeno time da su spojevi formule la [image] u kojima A, L, M, Q2, Q3, Q4, R1, R6, Ra, Rb, Rc, W, Z1, Z2, Z3 imaju isto značenje kako je definirano u zahtjevu 1, njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
3. Spojevi prema zahtjevu1, naznačeno time da su spojevi formule Ib [image] u kojima A, L, M, Q2, Q3, Q4, R1, R6, R7, Ra, Rb, Rc, W imaju isto značenje kako je definirano u zahtjevu 1, njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
4. Spojevi prema zahtjevu1, naznačeno time da su spojevi formule Ic [image] u kojima A, L, M, R1, R2, R3, R4, R6, Ra, Rb, Rc, W, Z1, Z2, Z3 imaju isto značenje kako je definirano u zahtjevu 1, njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
5. Spojevi prema zahtjevu1, naznačeno time da su spojevi formule Id [image] u kojima A, L, M, R1, R2, R3, R4, R6, R7, Ra, Rb, Rc, W imaju isto značenje kako je definirano u zahtjevu 1, njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
6. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da W predstavlja -C(O)-, -S(O)2-, gdje su skupine vezane za dušik iz -NRc- dijela pomoću atoma ugljika ili sumpora; njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
7. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da M predstavlja C1-7 alkil, C3-7 cikloalkil, od kojih su obje skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od: fluoro, -OH, -CN, -NH2, -OC1-3 alkil, -SC1-3 alkil, aril [gdje dvije zadnje aril skupine mogu biti supstituirane s jednim ili više supstituenata odabranih od halo, OH, -CN, C1-3 alkil, OC1-3 alkil (gdje su dvije zadnje alkilne skupine opcionalno supstituirane s jednim ili više atoma fluora)], C1-7 alkil, C3-7 cikloalkil-C0-2-alkil (gdje su zadnje alkil i cikloalkil skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -CN, =O, -NH2, -NH(C1-3 alkil), -N(C1-3 alkil)2, -OH, -OC1-3 alkil); ili aril, heteroaril, 4-7-člani heterocikloalkil, gdje su sve skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od halo, -CN, -OC1-3 alkil, C1-7 alkil, C3-7 cikloalkil, (gdje su zadnje alkil i cikloalkil skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -CN, -OC1-3alkil); njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
8. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da R6 predstavlja vodik; C1-5 alkil, C3-5cikloalkil-C0-1 alkil, gdje su dvije zadnje skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -OCH3, -NH(C1-3 alkil), N(C1-3 alkil)2; njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
9. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da R2, R3 i R4 neovisno predstavljaju vodik, fluoro, kloro- ili -CH3 opcionalno supstituiran s jednim ili više atoma fluora; njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
10. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da L predstavlja -C(O)NH- ili -S(O)2NH-, gdje skupine su vezane za 9-članu fuziranu heteroaromatsku građu preko odgovarajućeg atoma ugljika ili sumpora; njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
11. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da svaki R7 predstavlja vodik, halo, C1-5 alkil-O-, C3-5cikloalkil-C0-2 alkil-O-, 4-5-člani heterocikloalkil-C0-2 alkil-O- (gdje su zadnje tri skupine alkil, cikloalkil ili heterocikloalkil fragmenata opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -OC1-3 alkil ili s jednim ili više C1-3 alkilnih skupina, koje mogu biti opcionalno supstituirane s jednim ili više atoma fluora); njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
12. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da A predstavlja vodik, C1-6 alkil, C3-6 alkinil, fenil, 5-6-člani heteroaril, C3-6cikloalkil-C0-2alkil-, 4-6-člani heterocikloalkil-C0-2alkil, fenil-C1-3alkil-, 5-6-člani heteroaril-C1-3alkil gdje su skupine alkil-, alkinil-, cikloalkil- i heterocikloalkil-fragmenata opcionalno supstituirane s jednim ili više supstituenata odabranih od R9a i fenil, tienil i piridil fragmenti su opcionalno supstituirani s jednim ili dva supstituenta odabrana od R9b; svaki R9a neovisno predstavlja fluoro, fenil, C1-2alkil,-OC1-4alkil gdje su zadnje dvije skupine opcionalno supstituirane s jadnim do tri atoma fluora; svaki R9b predstavlja neovisno fluoro, chloro, bromo, C1-2 alkil, -OC1-2 alkil gdje su zadnje dvije skupine opcionalno supstituirane s jednim ili više fluoro; njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
13. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da M predstavlja C1-6 alkil, C3-6 cikloalkil, 4-6-člani heterocikloalkil, od kojih su sve skupine opcionalno supstituirane s jednim ili više skupina odabranih od fluoro, -OH, -CN, -NH2, fenil, -CF3, C1-2 alkil, C3-5 cikloalkil-C0-1 alkil; ili fenil, 5-6-člani heteroaril od kojih su obje opcionalno supstituirane s jednim ili više substituenata neovisno odabranih od fluoro, kloro, metil, -CF3, -OCH3; njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
14. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da su spojevi formule Ie [image] gdje A predstavlja vodik, C1-6 alkil, fenilpropargil, fenil, C3-6cikloalkil-C0-2alkil-, tetrahidrofuranil-C0-2alkil, pirolidinil-C0-2alkil, piperidin-C0-2alkil, piridil-C1-2alkil-, gdje su skupine alkil-, alkinil-, cikloalkil- i heterocikloalkil fragmenata opcionalno supstituirane s jednim ili više supstituenata odabranih od R9a i fenil i piridil fragmenti su opcionalno supstituirani s jednim ili više supstituenata odabranih od R9b; svaki R9a neovisno predstavlja fluoro, C1-2alkil, -OC1-4alkil gdje su zadnje dvije skupine alkilnih fragmenata opcionalno supstituirane s jednim ili više atoma fluora; svaki R9b predstavlja neovisno fluoro, kloro, bromo, L predstavlja -C(O)NH- ili -S(O)2NH-, gdje su skupine vezane za 9-članu fuziranu heteroaromatsku građu preko odgovarajućeg atoma ugljika ili sumpora; W predstavlja -C(O)-, -S(O)2-; M predstavlja alkil, C3-6 cikloalkil gdje su zadnje dvije skupine opcionalno supstituirane s jednim ili više skupina odabranih od fluoro, -OH, -CN, -NH2, fenil, CF3, C1-2 alkil, ciklopropil-metil; ili predstavlja oksetanil ili tetrahidrofuranil, gdje su obje skupine opcionalno supstituirane s CH3-skupinom; ili fenil, tienil od kojih su obje opcionalno supstituirane s jednom ili dva supstituenta neovisno odabrana od fluoro ili kloro, R1 predstavlja fluoro, kloro, bromo, CH3, CH2F, CHF2, CF3, -OCH3; R4 predstavlja vodik ili fluoro; R6 predstavlja vodik, C1-3 alkil, C3-5cikloalkil-C0-1 alkil, gdje su zadnje dvije skupine opcionalno supstituirane s jednim ili više supstituenata odabranih od fluoro, -OCH3, -NH(C1-3 alkil), N(C1-3 alkil)2; R7-22 predstavlja vodik, halo, -OC1-5alkil, gdje je zadnja skupina alkila opcionalno supstituirana s jednim ili više atoma fluora; R7-Z1 i R7-Z3 neovisno predstavljaju vodik ili fluoro; njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
15. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da su Primjer Struktura [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] njihove soli, posebice njihove fiziološki prihvatljive soli s organskim ili anorganskim kiselinama i bazama.
16. Spojevi prema bilo kojem od prethodnih zahtjeva, naznačeni time da su za upotrebu kao farmaceutski proizvodi.
17. Farmaceutski sastav koji sadrži barem jedan spoj prema bilo kojem zahtjevu od 1 do 15 u mješavini s farmaceutski prihvatljivim pomoćnim sredstvom, razrjeđivačem ili nosačem.
18. Spojevi prema bilo kojem od zahtjeva 1 do 15, naznačeni time da su za upotrebu u prevenciji i/ili liječenju upalnih bolesti i povezanih stanja.
19. Upotreba prema zahtjevu 18, naznačena time da je stanje koje treba liječiti i/ili prevenirati bol.
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