HRP20100541T1 - Derivati bifeniloksioctene kiseline za liječenje respiratornih bolesti - Google Patents

Derivati bifeniloksioctene kiseline za liječenje respiratornih bolesti Download PDF

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Publication number
HRP20100541T1
HRP20100541T1 HR20100541T HRP20100541T HRP20100541T1 HR P20100541 T1 HRP20100541 T1 HR P20100541T1 HR 20100541 T HR20100541 T HR 20100541T HR P20100541 T HRP20100541 T HR P20100541T HR P20100541 T1 HRP20100541 T1 HR P20100541T1
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HR
Croatia
Prior art keywords
oxy
biphenyl
acetic acid
sulfonyl
halogen
Prior art date
Application number
HR20100541T
Other languages
English (en)
Inventor
Jon Luker Timothy
Tasneem Mohammed Rukhsana
Dickinson Mark
Thom Stephen
Original Assignee
Astrazeneca Ab
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Publication date
Priority claimed from GB0520324A external-priority patent/GB0520324D0/en
Priority claimed from GB0525082A external-priority patent/GB0525082D0/en
Priority claimed from GB0602800A external-priority patent/GB0602800D0/en
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of HRP20100541T1 publication Critical patent/HRP20100541T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
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Abstract

Spoj formule (I) ili njegova farmaceutski prihvatljiva sol: naznačen time da: A i D su nezavisno izabrani iz vodika, halogena, nitrila, C1-3 alkila, C1-3 alkoksi, pri čemu zadnje 2 skupine mogu opcijski biti supstituirane sa jednim ili više atoma halogena; X je halogen ili C1-3 alkil koji je po potrebi supstituiran sa jednim ili više atoma halogena; Y je veza; Z je aril ili heteroaril po potrebi supstituiran sa jednim ili više atoma izabranih iz halogena, nitrila, C1-6 alkila, C1-6 alkoksi, SO2C1-6alkila, heteroarila; a zadnje četiri skupine mogu po potrebi biti supstituirane sa atomima halogena, nitrilom ili SO2C1-6alkilom; R1 i R2 nezavisno predstavljaju atom vodika ili C1-3 alkilnu skupinu; iliR1 i R2 zajedno mogu tvoriti 3-8-člani prsten koji po potrebi sadrži jedan ili više atoma izabranih iz O, S, NR3 i samog sebe, a koji su po potrebi supstituirani sa jednim ili više C1-C3 alkila; iR3 je vodik ili C1-C6 alkil. Patent sadrži još 21 patentni zahtjev.

Description

DERIVATI BIFENILOKSIOCTENE KISELINE ZA LIJEČENJE RESPIRATORNIH BOLESTI

Claims (22)

1. Spoj formule (I) ili njegova farmaceutski prihvatljiva sol: [image] naznačen time da: A i D su nezavisno izabrani iz vodika, halogena, nitrila, C1-3 alkila, C1-3 alkoksi, pri čemu zadnje 2 skupine mogu opcijski biti supstituirane sa jednim ili više atoma halogena; X je halogen ili C1-3 alkil koji je po potrebi supstituiran sa jednim ili više atoma halogena; Y je veza; Z je aril ili heteroaril po potrebi supstituiran sa jednim ili više atoma izabranih iz halogena, nitrila, C1-6 alkila, C1-6 alkoksi, SO2C1-6alkila, heteroarila; a zadnje četiri skupine mogu po potrebi biti supstituirane sa atomima halogena, nitrilom ili SO2C1-6alkilom; R1 i R2 nezavisno predstavljaju atom vodika ili C1-3 alkilnu skupinu; ili R1 i R2 zajedno mogu tvoriti 3-8-člani prsten koji po potrebi sadrži jedan ili više atoma izabranih iz O, S, NR3 i samog sebe, a koji su po potrebi supstituirani sa jednim ili više C1-C3 alkila; i R3 je vodik ili C1-C6 alkil.
2. Spoj prema zahtjevu 1, naznačen time, da u njemu X je kloro, fluoro ili metil.
3. Spoj prema zahtjevu 1 ili 2, naznačen time, da se u njemu skupina SO2-Y-Z nalazi na poziciji 4 u fenilnom prstenu.
4. Spoj prema zahtjevu 1 ili 2, naznačen time, da se u njemu skupina SO2-Y-Z nalazi na poziciji 4 u fenilnom prstenu, orto u odnosu na obje skupine A i D.
5. Spoj prema zahtjevu 1 ili 2, naznačen time, da se u njemu skupina SO2-Y-Z nalazi na poziciji 4 u fenilnom prstenu, orto u odnosu na skupinu A i meta u odnosu na skupinu D.
6. Spoj prema bilo kojem od zahtjeva od 1 do 5, naznačen time, da su u njemu skupine A i D nezavisno vodik, halogen ili C1-3 alkil (posljednji je po potrebi supstituiran sa atomima halogena).
7. Spoj prema bilo kojem od zahtjeva od 1 do 6, naznačen time, da A je vodik, halogen ili CF3.
8. Spoj prema bilo kojem od zahtjeva od 1 do 7, naznačen time, da D je vodik, halogen ili metil.
9. Spoj prema bilo kojem od zahtjeva od 1 do 8, naznačen time, da su A i D nezavisno odabrani iz vodika i halogena.
10. Spoj prema bilo kojem od zahtjeva od 1 do 9, naznačen time, da R1 i R2 su nezavisno vodik ili C1-3 alkil.
11. Spoj prema bilo kojem od zahtjeva od 1 do 9, naznačen time, da R1 i R2 su nezavisno vodik ili metil.
12. Spoj prema bilo kojem od zahtjeva od 1 do 11, naznačen time, da Y je veza.
13. Spoj prema bilo kojem od zahtjeva od 1 do 12, naznačen time, da Z je fenil koji je po potrebi supstituiran sa halogenom ili C1-6 alkoksi.
14. Spoj prema bilo kojem od zahtjeva od 1 do 13, naznačen time, da Z je fenil koji je po potrebi supstituiran sa halogenom.
15. Spoj prema bilo kojem od zahtjeva od 1 do 14, naznačen time, da Z je fenil koji je po potrebi supstituiran sa fluoro.
16. Spoj formule (I) prema bilo kojem od zahtjeva od 1 do 15, naznačen time, da je odabran iz: {[5-Kloro-4'-(fenilsulfonil)bifenil-2-il]oksi}octene kiseline; {[3',5-Difluoro-4'-(fenilsulfonil)bifenil-2-il]oksi}octene kiseline; (2S)-2-{[3',5-Difluoro-4'-(fenilsulfonil)bifenil-2-il]oksi}propanske kiseline; ({5-Kloro-3'-fluoro-4'-[(4-fluorofenil)sulfonil]bifenil-2-il}oksi)octene kiseline; {[2',5-Difluoro-4'-(fenilsulfonil)bifenil-2-il]oksi}octene kiseline; {[5-Kloro-2'-fluoro-4'-(fenilsulfonil)bifenil-2-il]oksi}octene kiseline; {[5-fluoro-4'-(fenilsulfonil)-3'-(trifluorometil)bifenil-2-il]oksi}octene kiseline; (2S)-2-({5-kloro-4'-[(4-fluorofenil)sulfonil]bifenil-2-il}oksi)propanske kiseline; ({5-kloro-2'-fluoro-4'-[(4-fluorofenil)sulfonil]bifenil-2-il}oksi)octene kiseline; (2S)-2-({5-kloro-2'-fluoro-4'-[(4-fluorofenil)sulfonil]bifenil-2-il}oksi)propanske kiseline; (2S)-2-({3',5-difluoro-4'-[(2-fluorofenil)sulfonil]bifenil-2-il}oksi)propanske kiseline; (2S)-2-({3',5-difluoro-4'-[(4-metoksifenil)sulfonil]bifenil-2-il}oksi)propanske kiseline; (2S)-2-({3',5-difluoro-4'-[(3-fluorofenil)sulfonil]bifenil-2-il}oksi)propanske kiseline; ({5-kloro-4'-[(4-fluorofenil)sulfonil]-2'-metilbifenil-2-il}oksi)octene kiseline; (2S)-2-{[2'-kloro-5-fluoro-4'-(fenilsulfonil)bifenil-2-il]oksi}propanske kiseline; ({3'-fluoro-4'-[(4-fluorofenil)sulfonil]-5-metilbifenil-2-il}oksi)octene kiseline; ({5-kloro-4'-[(4-metoksifenil)sulfonil]bifenil-2-il}oksi)octene kiseline; ({4'-[(2-klorofenil)sulfonil]-3',5-difluorobifenil-2-il}oksi)octene kiseline; (2S)-2-{[3'-kloro-5-fluoro-4'-(fenilsulfonil)bifenil-2-il]oksi}propanske kiseline; ({4'-[(3-klorofenil)sulfonil]-2',5-difluorobifenil-2-il}oksi)octene kiseline; ({2'-fluoro-4'-[(4-fluorofenil)sulfonil]-5-metilbifenil-2-il}oksi)octene kiseline; {[3'-fluoro-5-metil-4'-(fenilsulfonil)bifenil-2-il]oksi}octene kiseline; {[5-kloro-3',5'-difluoro-4'-(fenilsulfonil)bifenil-2-il]oksi}octene kiseline i njegovih farmaceutski prihvatljivih soli.
17. Spoj formule (I) prema bilo kojem od zahtjeva od 1 do 15, naznačen time, da navedeni spoj je ({5-Kloro-3'-fluoro-4'-[(4-fluorofenil)sulfonil]bifenil-2-il}oksi)octena kiselina;
18. Spoj formule (I) prema bilo kojem od zahtjeva od 1 do 17, naznačen time, da je za upotrebu kod terapije.
19. Uporaba spoja formule (I), ili njegove farmaceutski prihvatljive soli, kao što je definirano u prethodnim zahtjevima, naznačena time, da se navedeni spoj koristi u proizvodnji lijeka za liječenje humanih bolesti ili stanja u kojima je korisna modulacija receptorske aktivnosti CRTh2.
20. Spoj, naznačen time, da ima formulu (II): [image] pri čemu R1, R2, A, D, X, Y i Z su definirani kao u zahtjevu 1, a R4 je C1-10 alkilna skupina.
21. Spoj, naznačen time, da ima formulu (III) [image] pri čemu A, D, X, Y i Z su definirani kao u zahtjevu 1.
22. Spoj, naznačen time, da ima formulu (V) [image] gdje R5, A, D, X, Y i Z su definirani kao u zahtjevu 1.
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AU2010257385B2 (en) 2011-11-10
WO2007039741A1 (en) 2007-04-12
ES2347470T3 (es) 2010-10-29
SA06270368B1 (ar) 2009-12-29
ECSP088414A (es) 2008-05-30
NZ567070A (en) 2010-12-24
US8415394B2 (en) 2013-04-09
JP5114413B2 (ja) 2013-01-09
US8349897B2 (en) 2013-01-08
EP1937633B8 (en) 2010-12-22
BRPI0616969A2 (pt) 2011-07-05
AU2010257385C1 (en) 2012-06-21
US20110152374A1 (en) 2011-06-23
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US8008350B2 (en) 2011-08-30
TW200745003A (en) 2007-12-16
NO20082124L (no) 2008-06-20
CY1110812T1 (el) 2015-06-10
AR058077A1 (es) 2008-01-23
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RS51471B (en) 2011-04-30
AU2010257385A1 (en) 2011-01-20
EP1937633A1 (en) 2008-07-02
EP1937633B1 (en) 2010-08-04
ATE476414T1 (de) 2010-08-15
PL1937633T3 (pl) 2010-12-31
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IL190338A0 (en) 2009-09-22
UY29839A1 (es) 2007-05-31
AU2006298531A1 (en) 2007-04-12
KR20080050606A (ko) 2008-06-09
JP2009511454A (ja) 2009-03-19
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PT1937633E (pt) 2010-09-30
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