HRP20100079T1 - Novi derivati 3-fenilpropionske kiseline za liječenje dijabetesa - Google Patents

Novi derivati 3-fenilpropionske kiseline za liječenje dijabetesa Download PDF

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HRP20100079T1
HRP20100079T1 HR20100079T HRP20100079T HRP20100079T1 HR P20100079 T1 HRP20100079 T1 HR P20100079T1 HR 20100079 T HR20100079 T HR 20100079T HR P20100079 T HRP20100079 T HR P20100079T HR P20100079 T1 HRP20100079 T1 HR P20100079T1
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phenyl
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Majka Zbigniew
Stawinski Tomasz
Rusin Katarzyna
Sawicki Andzej
Kurowski Krzysztof
Matusiewicz Katarzyna
Sulikowski Daniel
Kowalczyk Piotr
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Adamed Sp. Z O.O.
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Abstract

Derivati 3-fenilpropionske kiseline formule (I):(I) naznačeni time da: W predstavlja COOH ili -COO-C1-C4-alkil; Y predstavlja NH ili N-C1-C10-alkil; Z predstavlja NH, N-C1-C10-alkil, N-aril, N-heteroaril, S, ili O; KS predstavlja O; R1 do R8 svaki nezavisno predstavlja atom vodika ili njegovu zamjenu koja je odabrana iz skupine koja se sastoji od: C1-C4-alkila, C1-C4-alkoksi, C3-C7-cikloalkila, C3-C7-cikloalkoksi, C1-C4-tioalkoksi, C3-C7-ciklotioalkoksi, atoma halogena, halogen- supstituiranog C3-C7-cikloalkila, arila, heteroarila, -NO2, -CN, -SO2-NH2, -SO2-NH-C1-C4-alkila, -SO2-N(C1-C4-alkil)2, -CO-C1-C4-alkila, -O-CO-C1-C4-alkila, -CO-O-C1-C4-alkila, -CO-arila, -CO-NH2, -CO-NH-C1-C4-alkila, -CO-N(C1-C4-alkil)2;A predstavlja C3-C7-cikloalkil, halogen-supstituirani C3-C7-cikloalkil, fenil supstituiran sa etilenedioksi, aril odabran iz skupine koja se sastoji od tolila, ksilila i naftila, heteroaril odabran iz skupine koja se sastoji od pirol-1-ila, pirol-2-ila, pirol-3-ila, furila, tienila, imidazolila, oksazolila, tiazolila, izoksazolila, 1,2,4-triazolila, oksadiazolila, tiadiazolila, tetrazolila, piridinila, pirimidinila, 1,3,5-triazinila, indolila, benzo[b]furila, benzo[b]tienila, indazolila, benzimidazolila, azaindolila, kinolila, izsokinolinila, i karbazolila, zasićene ili djelomično nezasićen 5- do 6-člani heterociklil koji ima 1 do 4 heteroatoma odabranih od N, O i S, -NH-CO-C1-C4-alkila, -N(C1-C4-alkil)-CO-C1-C4-alkila, -NH-CO-arila, -N(C1-C4-alkil)-CO-arila, -N(C1-C4-alkil)-CO-heteroarila, -N(C1-C4-alkil)-CO-C3-C7-cikloalkila, -NH-CO-NH2, -NH-CO-NH-C1-C4-alkila, -NH-CS-NH-C1-C4-alkila, -NH-CO-NH-arila, -NH-CS-NH-arila, -SO2-C1-C4-alkila, -SO2-arila, ili -SO2-heteroarila; pri čemu su aril, heteroaril i heterociklil po potrebi supstituirani sa jednim ili više supstituenata nezavisno odabranih iz skupine koja se sastoji od C1-C4-alkila, C1-C4-alkoksi, C1-C4-tioalkoksi, etilenedioksi, CN, halogena ili fenila, navedeni fenil je po potrebi supstituiran sa jednim ili više supstituenata nezavisno odabranih između C1-C4-alkila, C1-C4-alkoksi, i atoma halogena; in predstavlja cijeli broj od 0 do 4, uključivo; i njegove farmaceutski prihvatljive soli. Patent sadrži još 23 patentna zahtjeva.

Claims (24)

1. Derivati 3-fenilpropionske kiseline formule (I): [image] (I) naznačeni time da: W predstavlja COOH ili -COO-C1-C4-alkil; Y predstavlja NH ili N-C1-C10-alkil; Z predstavlja NH, N-C1-C10-alkil, N-aril, N-heteroaril, S, ili O; KS predstavlja O; R1 do R8 svaki nezavisno predstavlja atom vodika ili njegovu zamjenu koja je odabrana iz skupine koja se sastoji od: C1-C4-alkila, C1-C4-alkoksi, C3-C7-cikloalkila, C3-C7-cikloalkoksi, C1-C4-tioalkoksi, C3-C7-ciklotioalkoksi, atoma halogena, halogen- supstituiranog C3-C7-cikloalkila, arila, heteroarila, -NO2, -CN, -SO2-NH2, -SO2-NH-C1-C4-alkila, -SO2-N(C1-C4-alkil)2, -CO-C1-C4-alkila, -O-CO-C1-C4-alkila, -CO-O-C1-C4-alkila, -CO-arila, -CO-NH2, -CO-NH-C1-C4-alkila, -CO-N(C1-C4-alkil)2; A predstavlja C3-C7-cikloalkil, halogen-supstituirani C3-C7-cikloalkil, fenil supstituiran sa etilenedioksi, aril odabran iz skupine koja se sastoji od tolila, ksilila i naftila, heteroaril odabran iz skupine koja se sastoji od pirol-1-ila, pirol-2-ila, pirol-3-ila, furila, tienila, imidazolila, oksazolila, tiazolila, izoksazolila, 1,2,4-triazolila, oksadiazolila, tiadiazolila, tetrazolila, piridinila, pirimidinila, 1,3,5-triazinila, indolila, benzo[b]furila, benzo[b]tienila, indazolila, benzimidazolila, azaindolila, kinolila, izsokinolinila, i karbazolila, zasićene ili djelomično nezasićen 5- do 6-člani heterociklil koji ima 1 do 4 heteroatoma odabranih od N, O i S, -NH-CO-C1-C4-alkila, -N(C1-C4-alkil)-CO-C1-C4-alkila, -NH-CO-arila, -N(C1-C4-alkil)-CO-arila, -N(C1-C4-alkil)-CO-heteroarila, -N(C1-C4-alkil)-CO-C3-C7-cikloalkila, -NH-CO-NH2, -NH-CO-NH-C1-C4-alkila, -NH-CS-NH-C1-C4-alkila, -NH-CO-NH-arila, -NH-CS-NH-arila, -SO2-C1-C4-alkila, -SO2-arila, ili -SO2-heteroarila; pri čemu su aril, heteroaril i heterociklil po potrebi supstituirani sa jednim ili više supstituenata nezavisno odabranih iz skupine koja se sastoji od C1-C4-alkila, C1-C4-alkoksi, C1-C4-tioalkoksi, etilenedioksi, CN, halogena ili fenila, navedeni fenil je po potrebi supstituiran sa jednim ili više supstituenata nezavisno odabranih između C1-C4-alkila, C1-C4-alkoksi, i atoma halogena; i n predstavlja cijeli broj od 0 do 4, uključivo; i njegove farmaceutski prihvatljive soli.
2. Spoj prema zahtjevu 1, naznačen time da W predstavlja COOH.
3. Spoj prema bilo kojem zahtjevu 1 ili 2, naznačen time da Y predstavlja NH.
4. Spoj prema bilo kojem zahtjevu 1 ili 2, naznačen time da Y predstavlja N-C1-C4-alkil, posebice N-CH3.
5. Spoj prema bilo kojem zahtjevu 1 do 4, naznačen time da Z predstavlja O.
6. Spoj prema bilo kojem zahtjevu 1 do 4, naznačen time da Z predstavlja S.
7. Spoj prema bilo kojem zahtjevu 1 do 4, naznačen time da Z predstavlja N-C1-C4-alkil, posebice N-CH3.
8. Spoj prema bilo kojem zahtjevu 1 do 4, naznačen time da Z predstavlja N-fenil.
9. Spoj prema zahtjevu 1, naznačen time da W predstavlja COOH, Y predstavlja NH, i Z predstavlja O.
10. Spoj prema bilo kojem zahtjevu od 1 do 9, naznačen time da svaki R1 do R8 predstavlja atom vodika.
11. Spoj prema bilo kojem zahtjevu od 1 do 10, naznačen time da je n jednako 1 ili 2.
12. Spoj prema bilo kojem zahtjevu od 1 do 11, naznačen time da A predstavlja heterociklil, navedeni heterociklil je po potrebi supstitutuiran sa jednim ili više supstituenata nezavisno odabranih iz skupine koja se sastoji od C1-C4-alkila, C1-C4-alkoksi, C1-C4-tioalkoksi, CN, atoma halogena i fenila.
13. Spoj prema zahtjevu 12, naznačen time da A predstavlja izoksazolil, po potrebi supstitutuirani sa jednim ili više supstituenata nezavisno odabranih iz C1-C4-alkila, posebice -CH3.
14. Spoj prema bilo kojem zahtjevu od 1 do 11, naznačen time da A predstavlja fenil supstituiran sa etilenedioksi skupinom.
15. Spoj prema bilo kojem zahtjevu od 1 do 11, naznačen time da A predstavlja -N(C1-C4-alkil)-CO-C3-C7-cikloalkil.
16. Spoj prema zahtjevu 15, naznačen time da A predstavlja -N(CH3)-CO-cikloheksil.
17. Spoj prema bilo kojem zahtjevu od 1 do 11, naznačen time da A predstavlja -N(C1-C4-alkil)-CO-heteroaril, navedeni heteroaril je po potrebi supstitutuiran sa jednim ili više supstituenata nezavisno odabranih iz skupine C1-C4-alkil, C1-C4-alkoksi, C1-C4-tioalkoksi, CN, atom halogena ili fenila, navedeni fenil je po potrebi supstituiran sa jednim ili više supstituenata nezavisno odabranih od C1-C4-alkil, C1-C4-alkoksi, i halogena.
18. Spoj prema zahtjevu 17, naznačen time da heteroaril je pirimidinil, po potrebi supstitutuiran sa jednim ili više supstituenata nezavisno odabranih iz skupine koja se sastoji od C1-C4-alkila, C1-C4-alkoksi, halogena, i fenila, navedeni fenil je po potrebi supstituiran sa jednim ili više supstituenata nezavisno odabranih od C1-C4-alkil, C1-C4-alkoksi, i atoma halogena.
19. Spoj prema bilo kojem zahtjevu od 1 do 18, naznačen time da ima stereokemijsku konfiguraciju kako je prikazano formulom (IA): [image] (IA) i njegove farmaceutski prihvatljive soli.
20. Spoj prema bilo kojem zahtjevu od 1 do 18, naznačen time da ima stereokemijsku konfiguraciju kako je prikazano formulom (IB): [image] (IB) i njegove farmaceutski prihvatljive soli.
21. Spoj prema zahtjevu 1, naznačen time da je navedeni spoj odabran između slijedećeg: (2S)-2-(1,3-benzoksazol-2-ilamino)-3-[4-(2,3-dihidro-1,4-benzodioksin-6-ilmetoksi)fenil]propionske kiseline, (2S)-2-(1,3-benzoksazol-2-ilamino)-3-[4-((3,5-dimetilisoksazol-4-il)metoksi)fenil]propionske kiseline, (2S)-2-(1,3-benzoksazol-2-ilamino)-3-[4-(2-[(cikloheksilkarbonil)(metil)amino]etoksi)fenil]propionske kiseline, (2S)-2-(1,3-benzoksazol-2-ilamino)-3-[4-(2-[5-metil-2-(3,4,5-trimetoksifenil)-1,3-oksazol-4-il]etoksi)fenil]propionske kiseline, (2S)-2-(1,3-benzoksazol-2-ilamino)-3-[4-(4-{2-[[6-(2-klorofenil)-5-cijano-2-(metiltio)pirimidin-4-il](metil)amino]etoksi})fenil]propionske kiseline, (2S)-2-(1,3-benzoksazol-2-ilamino)-3-[4-(2-(2-tert-butil-5-metil-1,3-oksazol-4-il)etoksi)fenil]propionske kiseline, (2S)-2-(1,3-benzotiazol-2-ilamino)-3-[4-(2-[(cikloheksilkarbonil)(metil)amino]etoksi)fenil]propionske kiseline, i njihovih farmaceutski prihvatljivih soli.
22. Farmaceutski sastav koji sadrži spoj kako je definiran u bilo kojem od zahtjeva 1 do 21 ili njegova farmaceutski prihvatljiva sol zajedno sa farmaceutski prihvatljivim nosačem i/ili ekscipijentom.
23. Spoj kako je definiran u bilo kojem od zahtjeva 1 do 21 naznačen time da se koristi kao lijek.
24. Upotreba spoja kako je definiran u bilo kojem od zahtjeva 1 do 21 naznačena time da se koristi za pripremu lijeka za liječenje i/ili prevenciju bolesti i stanja posredovanih sa peroksisomnim proliferatorski-aktiviranim receptorom gama (PPARγ), pri čemu su navedene bolesti ili stanja odabrana iz skupine koja se sastoji od dijabetesa tipa 2, inzulinske rezistencije, metaboličkog sindroma, komplikacija potaknutih ili povezanih sa dijabetesom, kardiovaskularnih poremećaja, ateroskleroze, pretilosti, kognitivnih poremećaja, i poremećaja metabolizma lipida.
HR20100079T 2004-12-20 2010-02-15 Novi derivati 3-fenilpropionske kiseline za liječenje dijabetesa HRP20100079T1 (hr)

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PL371841A1 (pl) * 2004-12-20 2006-06-26 ADAMED Sp.z o.o. Nowe związki pochodne kwasu 3-fenylopropionowego
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PL372356A1 (pl) * 2005-01-20 2006-07-24 ADAMED Sp.z o.o. Nowe związki, pochodne kwasu 3-fenylopropionowego
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IL183563A0 (en) 2007-09-20
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ZA200704584B (en) 2008-10-29
US20070219259A1 (en) 2007-09-20
MX2007007452A (es) 2007-11-07
ES2341020T3 (es) 2010-06-14
JP2008524166A (ja) 2008-07-10
NO20073736L (no) 2007-07-18
UA89807C2 (ru) 2010-03-10
PT1833805E (pt) 2010-03-31
US20070088061A1 (en) 2007-04-19
CY1110622T1 (el) 2015-04-29
CN101084203A (zh) 2007-12-05
PL371841A1 (pl) 2006-06-26
CA2588662C (en) 2010-12-07
RU2360906C2 (ru) 2009-07-10
RU2007127724A (ru) 2009-01-27
PL1833805T3 (pl) 2010-04-30
US7312338B2 (en) 2007-12-25
EP1833805A1 (en) 2007-09-19
ATE457305T1 (de) 2010-02-15
EP1833805B1 (en) 2010-02-10
KR20070097057A (ko) 2007-10-02
KR100923199B1 (ko) 2009-10-22
WO2006067086A1 (en) 2006-06-29
AU2005318221A1 (en) 2006-06-29
CA2588662A1 (en) 2006-06-29
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BRPI0519584A2 (pt) 2009-02-17
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