HRP20201604T1 - Sulfonamidi kao gpr40- i gpr120-agonisti - Google Patents

Sulfonamidi kao gpr40- i gpr120-agonisti Download PDF

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HRP20201604T1
HRP20201604T1 HRP20201604TT HRP20201604T HRP20201604T1 HR P20201604 T1 HRP20201604 T1 HR P20201604T1 HR P20201604T T HRP20201604T T HR P20201604TT HR P20201604 T HRP20201604 T HR P20201604T HR P20201604 T1 HRP20201604 T1 HR P20201604T1
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Croatia
Prior art keywords
phenyl
sulfamoyl
heptanoic acid
dimethylphenyl
methyl
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HRP20201604TT
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English (en)
Inventor
Maria DE PIZZOL
Anna SIRICO
Mara Zippoli
Gianluca Bianchini
Andrea Beccari
Andrea Aramini
Chiara Rossana Maria LIBERATI
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Dompé Farmaceutici S.P.A.
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Publication of HRP20201604T1 publication Critical patent/HRP20201604T1/hr

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    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
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    • C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
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Claims (17)

1. Spoj formule (I): [image] i njegove farmaceutski prihvatljive soli, naznačen time što: A je mono ili di-karbociklični ostatak, po izboru djelomično ili potpuno nezasićen, koji sadrži atome ugljika i po izboru jedan ili više heteroatoma izabranih od N, S ili O; R1, R2, R3 su nezavisno izabrani od grupe koja sadrži -H, -halogen, -CF3, -CN, -CH2CN, -OMe, -OCF3, -OH, fenil, -OPh, -OCH2Ph, -OCH2OMe, -OCH2CN - NO2, -NR'R", linearni ili razgranati C1-C6 alkil, -O(CH2)p-S(O)2Me i heterociklus sa petočlanim prstenom; gdje su R' i R" nezavisno -H ili C1-C4 alkil; gdje su fenil i heterociklus sa petočlanim prstenom nezavisno nesupstituirani ili supstituirani sa grupom izabranom od grupe koja sadrži linearni ili razgranati C1-C4 alkil, halogen, -OMe i -OH; p je 1 do 4; X je -CH2 ili -C(O); n je 0, 1 ili 2; R4 je -Y-C(O)OH, gdje Y je C4-C18 ugljikovodik ravnog lanca, zasićen ili nezasićen, pri čemu poželjno ima od 6 do 10 atoma ugljika; R4 je u položaju meta ili para u aromatičnom prstenu; gdje kada je A fenil, n je 0, Y je C4 ugljikovodik, bar jedan od navedenih R1, R2, R3 nije vodik; gdje kada je A fenil, n je 0, Y je C4 ugljikovodik, R1 i R2 su vodik, R3 nije Cl u položaju para u aromatičnom prstenu.
2. Spoj prema patentnom zahtjevu 1, gdje A je fenil, naftil, bifenil ili zasićeni ili nezasićeni heterociklus sa petočlanim prstenom koji ima pet atoma u prstenu pri čemu su 1, 2, 3 ili 4 atoma u prstenu nezavisno izabrana od N, O i S.
3. Spoj prema patentnom zahtjevu 1 ili 2, gdje je heterociklus sa petočlanim prstenom izabran od grupe koja sadrži tienil, furil, pirolil, imidazolil, tiazolil, oksazolil, pirazolil, izotiazolil, izoksazolil, 1,2,3-triazolil, tetrazolil, 1,2,3-tiadiazolil, 1,2,3-oksadiazolil, 1,2,4-triazolil, 1,2,4-tiadiazolil, 1,2,4-oksadiazolil, 1,3,4-triazolil, 1,3,4-tiadiazolil, 1,3,4-oksadiazolil i benzimidazol, po izboru djelomično zasićen.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3, gdje su R1, R2, R3 nezavisno izabrani od grupe koja sadrži -H, -halogen, -CF3, -OMe, -OH, fenil, -OPh, -OCH2Ph, -OCH2OMe, -OCH2CN -NO2, -NH2, -NMe2, linearni ili razgranati C1-C6 alkil i -O(CH2)p-S(O)2Me.
5. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, gdje n je 0 ili 1.
6. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, gdje je R4 u položaju meta u aromatičnom prstenu.
7. Spoj prema bilo kojem od patentnih zahtjeva 1 do 6 izabrano od: 7-(3-(N-(4-fluoro-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (1); 7-(3-(N-(2,4,6-trimetilbenzil)sulfamoil)fenil)heptanske kiseline (2); 7-(3-(N-(4-izopropil-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (3); 7-(3-(N-(4-kloro-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (4); 7-(3-(N-(4-(dimetilamino)-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (5); 7-(3-(N-(2,6-dimetil-4-(trifluorometil)fenil)sulfamoil)fenil)heptanske kiseline (6); 7-(3-(N-(4-bromo-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (7); 7-(3-(N-(4-metoksi-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (8); 7-(3-(N-(6-fluoro-4-metil-[1,1'-bifenil]-3-il)sulfamoil)fenil)heptanske kiseline (9); 7-(3-(N-(5-fluoro-3-metil-[1,1'-bifenil]-2-il)sulfamoil)fenil)heptanske kiseline (10); 6-{3-[(2,4,6-trimetilfenil)sulfamoil]fenil}heksanske kiseline(11); 7-(3-(N-(3,5-dimetil-1H-pirazol-4-il)sulfamoil)fenil)heptanske kiseline (12); 7-(3-(N-(2,4-dimetiltiazol-5-il)sulfamoil)fenil)heptanske kiseline (13); 7-(3-(N-(4,5-dimetiltiazol-2-il)sulfamoil)fenil)heptanske kiseline (14); 7-(3-(N-(4,5-dimetiloksazol-2-il)sulfamoil)fenil)heptanske kiseline (15); 7-(3-(N-(5-fenil-1,2,4-tiadiazol-3-il)sulfamoil)fenil)heptanske kiseline (16); 7-(3-(N-(3-metil-1,2,4-tiadiazol-5-il)sulfamoil)fenil)heptanske kiseline (17); 7-(3-(N-(5-metil-1,3,4-tiadiazol-2-il)sulfamoil)fenil)heptanske kiseline (18); 7-(3-(N-(3,5-dimetilizoksazol-4-il)sulfamoil)fenil)heptanske kiseline (19); 7-(3-(N-(5-metil-4H-1,2,4-triazol-3-il)sulfamoil)fenil)heptanske kiseline (20); 7-(3-(N-(3,5-dimetil-4H-1,2,4-triazol-4-il)sulfamoil)fenil)heptanske kiseline (21); 7-(3-(N-(3-fenilizotiazol-5-il)sulfamoil)fenil)heptanske kiseline (22); 7-{3-[(5-hidroksinaftalen-1-il)sulfamoil]fenil}heptanske kiseline (23); 7-{3-[(4-fluoro-2,6-dimetilbenzoil)sulfamoil]fenil}heptanske kiseline (24); 7-{4-[(4-fluoro-2,6-dimetilfenil)sulfamoil]fenil}heptanske kiseline (25); 7-(3-(N-(2-etil-2H-1,2,3-triazol-4-il)sulfamoil)fenil)heptanske kiseline (26); 7-(3-(N-(2-metil-2H-tetrazol-5-il)sulfamoil)fenil)heptanske kiseline (27); 7-(3-(N-(4-metil-4,5-dihidrooksazol-2-il)sulfamoil)fenil)heptanske kiseline (28); 7-(3-(N-(3a,4,5,6,7,7a-heksahidro-1H-benzo[d]imidazol-2il)sulfamoil)fenil) heptanske kiseline (29); 7-(3-(N-(3-fenilizotiazol-4-il)sulfamoil)fenil)heptanske kiseline (30); 7-(3-(N-(4-hidroksi-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (31); 7-(3-(N-(3,5-dimetil-[1,1'-bifenil]-4-il)sulfamoil)fenil)heptanske kiseline (32); 7-(3-(N-(2,6-dimetil-4-fenoksifenil)sulfamoil)fenil)heptanske kiseline (33); 7-(3-(N-(4-(benziloksi)-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (34); 7-(3-(N-(2,6-dimetil-4-(3(metilsulfonil)propoksi)fenil)sulfamoil)fenil)heptanske kiseline (35).
8. Spoj prema patentnom zahtjevu 7 izabrano od: 7-(3-(N-(4-fluoro-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (1); 7-(3-(N-(2,4,6-trimetilbenzil)sulfamoil)fenil)heptanske kiseline (2); 7-(3-(N-(4-izopropil-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (3); 7-(3-(N-(4-kloro-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (4); 7-(3-(N-(2,6-dimetil-4-(trifluorometil)fenil)sulfamoil)fenil)heptanske kiseline (6); 7-(3-(N-(4-bromo-2,6-dimetilfenil)sulfamoil)fenil)heptanske kiseline (7); 7-(3-(N-(6-fluoro-4-metil-[1,1'-bifenil]-3-il)sulfamoil)fenil)heptanske kiseline (9); 7-(3-(N-(5-fluoro-3-metil-[1,1'-bifenil]-2-il)sulfamoil)fenil)heptanske kiseline (10); 6-{3-[(2,4,6-trimetilfenil)sulfamoil]fenil}heksanske kiseline(11); 7-(3-(N-(2,6-dimetil-4-fenoksifenil)sulfamoil)fenil)heptanske kiseline (33).
9. Spoj prema bilo kojem od patentnih zahtjeva 1 do 8, za primjenu kao lijek.
10. Spoj za primjenu prema patentnom zahtjevu 9, u prevenciji i/ili liječenju bolesti ili poremećaja moduliranog pomoću GPR120 i/ili GPR40.
11. Spoj za primjenu prema patentnom zahtjevu 10, pri čemu su navedena bolest ili poremećaj izabrani od dijabetesa, poželjno dijabetesa tipa 2, poremećaja oralne tolerancije na glukozu, insulinske rezistencije, gojaznosti, poremećaja povezanih sa gojaznošću, metaboličkog sindroma, dislipidemije, povišenog LDL-a, povišenih triglicerida, upale izazvane gojaznošću, osteoporoze i kardiovaskularnih poremećaja povezanih sa gojaznošću.
12. Farmaceutska kompozicija koja sadrži kao aktivni sastojak bar jedno jedinjenje prema bilo kojem od patentnih zahtjeva 1 do 8 u kombinaciji sa fiziološki prihvatljivim ekscipijensima.
13. Farmaceutska kompozicija prema patentnom zahtjevu 12, pogodna za administriranje intravenskim, intraperitonealnim, inhalacijskim, topikalnim ili oralnim putem.
14. Farmaceutska kompozicija prema patentnim zahtjevima 12 ili 13, u obliku tečnosti ili čvrste supstance, poželjno u obliku kapsula, tableta, obloženih tableta, sirupa, praškova, granula, krema, losiona, sprejeva ili masti.
15. Spoj formule (I), gdje A je fenil R1, R2 i R3 su vodik, n je 0, i R4 je -(CH2)4-C(O)OH za primjenu u prevenciji i/ili liječenju bolesti ili poremećaja moduliranih pomoću GPR120 i/ili GPR40.
16. Spoj formule (I), gdje A je fenil R1 i R2 su vodik, R3 je Cl u položaju para u aromatičnom prstenu, n je 0, i R4 je -(CH2)4-C(O)OH za primjenu u prevenciji i/ili liječenju bolesti ili poremećaja moduliranog pomoću GPR120 i/ili GPR40.
17. Spoj za primjenu prema patentnom zahtjevu 15 ili 16, gdje je navedena bolest ili poremećaj odabran od dijabetesa (naročito dijabetesa tipa 2), poremećaja oralne tolerancije na glukozu, insulinske rezistencije, gojaznosti, poremećaja povezanih sa gojaznošću, metaboličkog sindroma, dislipidemije, povišenog LDL-a, povišenih triglicerida, upale izazvane gojaznošću, osteoporoze i kardiovaskularnih poremećaja povezanih sa gojaznošću.
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