HRP20130004T1 - 4-supstituirani derivati fenoksifeniloctene kiseline - Google Patents

4-supstituirani derivati fenoksifeniloctene kiseline Download PDF

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HRP20130004T1
HRP20130004T1 HRP20130004TT HRP20130004T HRP20130004T1 HR P20130004 T1 HRP20130004 T1 HR P20130004T1 HR P20130004T T HRP20130004T T HR P20130004TT HR P20130004 T HRP20130004 T HR P20130004T HR P20130004 T1 HRP20130004 T1 HR P20130004T1
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Croatia
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alkyl
methyl
substituted
unsubstituted
group
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HRP20130004TT
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George A. Doherty
Adam Cook
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Array Biopharma, Inc.
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Publication of HRP20130004T1 publication Critical patent/HRP20130004T1/hr
Publication of HRP20130004T8 publication Critical patent/HRP20130004T8/hr

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    • C07C311/19Sulfonamides 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 hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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Claims (17)

1. Spoj opće formule (I): [image] ili njegova sol, naznačen time što: R1 je Ar1-L1-W-L2-; L2 je -(CRcRd)m,-; W je -CONR3a- ili -NR3bCO-; svaki od R3a i R3b je H ili metil; L1 je -(CRaRb)n-, -(CH=CH)- ili -O(CRaRb), uz uvjet da kada je W -NR3CO-, L1 nije -(CH=CH)-; n i m su neovisno 0, 1 ili 2; svaki Ra, Rb, Rc i Rd je neovisno H, F, OH, metil ili ciklopropil, ili Ra i Rb ili Rc i Rd, zajedno s ugljikom na kojeg su vezani, tvore ciklopropilni prsten; Ar1 je fenil ili naftil, od kojih je svaki nesupstituiran ili je supstituiran s jednim ili više supstituenata, koje se neovisno bira između F, Cl, CN, CF3, CHF2, CH2F, SF5, metila, etila, ciklopropila, t-butila ili OMe, ili je Ar1 1,2,3,4-tetrahidronaftil, koji je nesupstituiran ili je supstituiran s metoksi, uz uvjet da kada je Ar1 naftil ili 1,2,3,4-tetrahidronaftil, n je 0; R2 je H, C1-C6 alkil, aminokiselinski ostatak ili dipeptid, ili CHRe(CH2)qRf; q je 1 do 6; Re je H, metil ili etil; Rf je NRgRh, u kojem Rg i Rh svaki neovisno predstavlja atom vodika ili C1-C4 alkilnu skupinu, ili Rg i Rh, zajedno s atomom dušika na kojeg su vezani, tvore 5-6-eročlani heterociklički prsten, koji izborno sadrži drugi heteroatom u prstenu, kojeg se bira između N i O, gdje je navedeni heterociklički prsten izborno supstituiran s jednom ili više skupina, koje se neovisno bira između C1-C6 alkila; A je CN, CH2NH2, CH2NR4aC(=O)R5 ili CH2NR4bSO2R6, Cl, OMe, (1-4C)alkil, ciklopropil, H, F, Br, CH2NH(1-4C alkil), CH2N(1-4C alkil)2, tienil ili fenil, koji je nesupstituiran ili je supstituiran s SO2Me; svaki od R4a i R4b je H ili metil; R5 je C1-C6 alkil, C1-C6 alkoksi, C3-C6 cikloalkil, hetAr1 ili Ar2; R6 je C1-C6 alkil, NH(C1-C6 alkil), N(C1-C6 alkil)2, Ar3 ili hetAr2; hetAr1 je 6-eročlani heteroaril, koji je nesupstituiran ili je supstituiran s jednom ili više skupina, koje se neovisno bira između atoma halogena i skupine formule -NR5aR5b, u kojoj svaki od R5a i R5b neovisno predstavlja atom vodika ili (1-4C) alkilnu skupinu, ili, zajedno s atomom dušika na kojeg su vezani, tvore pirolidinilnu, piperidinilnu ili morfolino skupinu; hetAr2 je 5-6-eročlani heteroaril, koji je nesupstituiran ili je supstituiran s jednom ili više skupina, koje se neovisno bira između C1-C4 alkila; Ar2 je fenil, koji je nesupstituiran ili je supstituiran s jednom ili više skupina, koje se neovisno bira između atoma halogena, CN, SF5, ciklopropila, C1-C4 alkilne skupine, C1-C4 alkoksi skupine i fluorC1-C4 alkilne skupine; Ar3 je definiran kao za Ar2; R7 i R8 su neovisno H, metil ili F; R9 je H ili metil; i R10 je H ili F.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ima formulu Ia, [image] gdje R1 je Ar1-L1-W-L2-; L2 je -(CRcRd)m-; W je -CONR3a- ili -NR3bCO-; svaki od R3a i R3b je H ili metil; L1 je -(CRaRb)a-, -(CH=CH)- ili -O(CRaRb)-, uz uvjet da kada je W -NR3CO-, L1 nije -(CH=CH)-; n i m su neovisno 0, 1 ili 2; svaki Ra, Rb, Rc i Rd je neovisno H, F, metil ili ciklopropil, ili Ra i Rb ili Rc i Rd, zajedno s ugljikom na kojeg su vezani, tvore ciklopropilni prsten; Ar1 je fenil ili naftil, od kojih je svaki nesupstituiran ili je supstituiran s jednim ili više supstituenata, koje se neovisno bira između F, Cl, CN, CF3, CHF2, CH2F, SF5, metila, etila i ciklopropila, uz uvjet da kada je Ar1 naftil, n je 0; R2 je H, C1-C6 alkil, aminokiselinski ostatak ili dipeptid, ili CHRe(CH2)qRf; q je 1 do 6; Re je H, metil ili etil; Rf je NRgRh, u kojem Rg i Rh svaki neovisno predstavlja atom vodika ili C1-C4 alkilnu skupinu, ili Rg i Rh, zajedno s atomom dušika na kojeg su vezani, tvore 5-6-eročlani heterociklički prsten, koji izborno sadrži drugi heteroatom u prstenu, kojeg se bira između N i O, gdje je navedeni heterociklički prsten izborno supstituiran s jednom ili više skupina, koje se neovisno bira između C1-C6 alkila; A je CN, CH2NH2, CH2NR4aC(=O)R5, CH2NR4bSO2R6, Cl, OMe, (1-4C)alkil ili ciklopropil; svaki od R4a i R4b je H ili metil; R5 je C1-C6 alkil, C1-C6 alkoksi, C3-C6 cikloalkil, hetAr1 ili Ar2; R6 je C1-C6 alkil, NH(C1-C6 alkil), N(C1-C6 alkil)2, Ar3 ili hetAr2; hetAr1 je 6-eročlani heteroaril, koji je nesupstituiran ili je supstituiran s jednom ili više skupina, koje se neovisno bira između atoma halogena i skupine formule -NR5aR5b, u kojoj svaki od R5a i R5b neovisno predstavlja atom vodika ili (1-4C) alkilnu skupinu, ili, zajedno s atomom dušika na kojeg su vezani, tvore pirolidinilnu, piperidinilnu ili morfolino skupinu; hetAr2 je 5-6-eročlani heteroaril, koji je nesupstituiran ili je supstituiran s jednom ili više skupina, koje se neovisno bira između C1-C4 alkila; Ar2 je fenil, koji je nesupstituiran ili je supstituiran s jednom ili više skupina, koje se neovisno bira između atoma halogena, CN, SF5, ciklopropila, C1-C4 alkilne skupine, C1-C4 alkoksi skupine i fluorC1-C4 alkilne skupine; Ar3 je definiran kao za Ar2; i R7 i R8 su neovisno H ili metil.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što se -L1-W-L2- bira između -CONH-, -CH2CONH-, -CH2CH2CONH-, -CONHCH2-, -CH2CONHCH2-, -NHCO-, -CH2NHCO-, -NHCOCH2-, -CH2CH2NHCO-, -CH2NHCOCH2-, -CH2CH2NHCOCH2-, -CH2N(CH)COCH2-, ciklopropilidenCH2NHCO, -CH2ONHCO-, -CH(OH)CH2NHCO- i -ciklopropilidinNHCO-.
4. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 ili 3, naznačen time što je Ar1 naftilna skupina ili fenilna skupina, koja je nesupstituirana ili je supstituirana s jednim ili dva supstituenta, koje se neovisno bira između F, Cl, CF3, OMe, Me i t-Bu ili 1,2,3,4-tetrahidronaftilne skupine, koja je nesupstituirana ili je supstituirana s OMe.
5. Spoj u skladu s patentnim zahtjevom 4, naznačen time što je Ar1 naftil, fenil, 4-fluorfenil, 3,4-difluorfenil, 2-klorfenil, 3-klorfenil, 4-klorfenil, 3,4-diklorfenil, 4-klor-3-fluorfenil, 3-klor-4-fluorfenil, 4-trifluormetilfenil, 3-fluor-4-fluormetilfenil, 3-trifluormetilfenil, 2,6-diklorfenil, 2,4-diklorfenil, 3-metoksifenil, 4-metoksifenil, 4-tertbutilfenil, 3-fluorfenil i 4-metilfenil, 1,2,3,4-tetrahidronaft-2-il ili 6-metoksi-1,2,3,4-tetrahidronaft-2-il.
6. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-5, naznačen time što je 6-eročlana heteroarilna skupina u hetAr1 piridilna skupina, a 5-6-eročlani heteroaril u hetAr2 je imidazolilna ili piridilna skupina.
7. Spoj u skladu s patentnim zahtjevom 6, naznačen time što je R5 C1-C6 alkil; C1-C6, alkoksi; C3-C6 cikloalkil; piridil, koji je nesupstituiran ili je supstituiran s atomom halogena ili skupinom formule -NR5aR5b, u kojoj svaki od R5a i R5b neovisno predstavlja atom vodika ili (1-4C) alkilnu skupinu, ili, zajedno s atomom dušika na gojeg su vezani, tvore pirolidinilnu, piperidinilnu ili morfolino skupinu; ili fenilna skupina, koja je nesupstituirana ili je supstituirana s jednim ili dva atoma halogena, a R6 je C1-C6 alkil, NH(C1-C6 alkil), N(C1-C6 alkil)2, fenilna skupina, koja je nesupstituirana ili je supstituirana s jednim ili dva atoma halogena, piridil ili imidazolil, koji je nesupstituiran ili je supstituiran s C1-C3 alkilnom skupinom.
8. Spoj u skladu s patentnim zahtjevom 7, naznačen time što je R5 metil, metoksi, cikloheksil, pirid-2-il, pirid-3-il, pirid-4-il, 6-klorpirid-3-il, 6-aminopirid-3-il, 6-pirolidin-1-ilpirid-3-il ili 4-fluorfenil, a R6 je metil, dimetilamino, 4-fluorfenil, 2,4-diklorfenil, pirid-3-il, 1-metilimidazol-5-il ili 6-dimetilaminopirid-3-il.
9. Spoj u skladu s patentnim zahtjevima 1 ili 3-5, naznačen time što se A bira između cijano, acetamidometila, cikloheksilamidometila, metoksikarbonilaminometila, pikolinamidometila, nikotinamidometila, izonikotinamidometila, 6-klorpirid-3-ilamidometila, 6-aminopirid-3-ilamidometila, 6-pirolidin-1-ilpirid-3-ilamidometila, 4-fluorbenzamidometila, metilsulfonamidometila, N,N-dimetilsulfamoilamino, 4-fluorfenilsulfonamidometila, 2,4-diklorfenilsulfononamidometila, 1-metilimidazol-5-ilsulfonamidometila, pirid-3-ilsulfonamidometila, 6-dimetilaminopirid-3-ilamidometila, 2-(4-fluorfenilsulfonamido)acetamidometila, dimetilaminometil, (N-metilmetilsulfonamido)metil, H, F, Br, Cl, metila, etila, ciklopropila, CH2NH2, CH2NMe2, tienila, fenila, 3-metilsulfonilfenila i 4-metilsulfonilfenila.
10. Spoj u skladu s patentnim zahtjevom 9, naznačen time što se A bira između cijano, acetamidometila, cikloheksilamidometila, metoksikarbonilaminometila, pikolinamidometila, nikotinamidometila, izonikotinamidometila, 4-fluorbenzamidometila, metilsulfonamidometila, N,N-dimetilsulfamoilamino, 4-fluorfenilsulfonamidometila, 2,4-diklorfenilsulfonamidometila, pirid-3-ilsulfonamidometila, 6-dimetilaminopirid-3-ilamidometila, 2-(4-fluorfenilsulfonamido)acetamidometila, dimetilaminometila, (N-metilmetilsulfonamido)metila, H, F, Br, Cl, metila, etila, ciklopropila, CH2NH2, CH2NMe2, tienila, SO2Me, fenila, 3-metilsulfonilfenila i 4-metilsulfonilfenila.
11. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 10, naznačen time što R2 je vodik.
12. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 11, naznačen time što R7 i R8 su H.
13. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 ili 3-12, naznačen time što R9 je H.
14. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 ili 3-13, naznačen time što R10 je H.
15. Farmaceutski pripravak, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 14, ili njegovu farmaceutski prihvatljivu sol, te farmaceutski prihvatljiv razrjeđivač ili podlogu.
16. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 14, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u terapiji.
17. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 14, ili njegove farmaceutski prihvatljive soli, naznačena time što je navedeni spoj namijenjen proizvodnji medikamenta za liječenje imunološkog poremećaja.
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