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HRP20180199T1 - Urea derivati ili njihove farmakološki prihvatljive soli korisni kao agonisti formil peptidnom receptoru-sličnom i (fprl-1) - Google Patents

Urea derivati ili njihove farmakološki prihvatljive soli korisni kao agonisti formil peptidnom receptoru-sličnom i (fprl-1) Download PDF

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Publication number
HRP20180199T1
HRP20180199T1 HRP20180199TT HRP20180199T HRP20180199T1 HR P20180199 T1 HRP20180199 T1 HR P20180199T1 HR P20180199T T HRP20180199T T HR P20180199TT HR P20180199 T HRP20180199 T HR P20180199T HR P20180199 T1 HRP20180199 T1 HR P20180199T1
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HR
Croatia
Prior art keywords
group
substituent
optionally
methoxyphenyl
urea
Prior art date
Application number
HRP20180199TT
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English (en)
Inventor
Hiroyasu Takahashi
Yoshifumi Saito
Kosuke Tsuda
Mitsuhito SHIBASAKI
Kohei Ohata
Original Assignee
Kyorin Pharmaceutical Co., Ltd.
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Publication date
Application filed by Kyorin Pharmaceutical Co., Ltd. filed Critical Kyorin Pharmaceutical Co., Ltd.
Publication of HRP20180199T1 publication Critical patent/HRP20180199T1/hr

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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
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    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
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Claims (27)

1. Spoj predstavljen općom formulom (I) ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat: [image] gdje, u formuli(I), Ar1 je fenil grupa koja po izboru ima supstituent(e), 5-očlana aromatična heterociklična grupa koja po izboru ima supstituent(e), 6-očlana aromatična heterociklična grupa koja po izboru ima supstituent(e), ili biciklička aromatična heterociklična grupa koja ima 8 ili 9 atoma i po izboru ima supstituent(e); Ar2 je fenil grupa koja po izboru ima supstituent(e) (izuzev za fenil grupu supstituiranu samo sa halogenim atomom (atomima)), 5-očlana aromatična heterociklična grupa koja po izboru ima supstituent(e), 6-očlana aromatična heterociklična grupa koja po izboru ima supstituent(e), ili biciklička aromatična heterociklična grupa koja ima 8 ili 9 atoma i po izboru ima supstituent(e); X je grupa odabrana iz grupe koja se sastoji od sljedećih a), b), i c), a) atom kisika ili atom sumpora, b) NR4, i c) NOR4, gdje, kada X je b) ili c), R4 je atom vodika, fenil grupa koja po izboru ima supstituent(e), heterociklična grupa koja po izboru ima supstituent(e), ili C1 do C6 alkil grupa koja po izboru ima supstituent(e); R1 je atom vodika, hidroksigrupa, C1 do C6 alkoksi grupa koja po izboru ima supstituent(e), ili C1 do C6 alkil grupa koja po izboru ima supstituent(e); R2 i R3 su svaki zasebno atom vodika ili C1 do C6 alkil grupa koja po izboru ima supstituent(e) ili zajedno formiraju C2 do C6 alkilen grupu; i svaki atom ugljika obilježen sa zvjezdicom je asimetrični atom ugljika; gdje izraz "po izboru ima supstituent(e)" znači po izboru supstituiran sa jednim ili više supstituenata odabranih iz grupe koja se sastoji od: halogen atoma, amino grupe, hidroksi grupe, cijano grupe, nitro grupe, karboksi grupe, C1 do C6 alkoksikarbonil grupa, formil grupe, C1 do C6 acil grupa, C1 do C6 alkil grupa, C1 do C6 alkilamino grupa, di-C1 do C6 alkilamino grupa, C1 do C6 alkoksi grupa, C1 do C6 alkiltio grupa, C3 do C6 cikloalkil grupa, 4- do 10-očlanih heterocikloalkil grupa, aromatičnih hidrokarbon cikličnih grupa koje po izboru imaju halogen atom, aromatičnih heterocikličkih grupa, C1 do C6 alkilkarbonilamino grupa, C3 do C6 cikloalkilkarbonilamino grupa, 4- do 10-očlanih heterocikloalkilkarbonilamino grupa, aromatičnih hidrokarbon cikličnih karbonilamino grupa, i aromatičnih heterocikličkih karbonilamino grupa, pod uvjetom da kada grupa po izboru ima supstituent(e) je odabrana iz grupe koja se sastoji od fenil, 5-očlane aromatične heterociklične grupe, 6-očlane aromatične heterociklične grupe, bicikličke aromatične heterociklične grupe koja ima 8 ili 9 atoma i heterociklične grupe, izborni supstituent nije di-C1 do C6 alkilamino grupa.
2. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje izraz "po izboru ima supstituent(e)" ima značenje definirano u patentnom zahtjevu 1, i gdje u formuli (I), Ar2 je grupa odabrana iz grupe koja se sastoji od sljedećih A1), A2), A3), A4), A5), A6), A7), A8), A9), i A10): [Kemijska formula 2] [image] gdje, kada Ar2 je A2), W1 je atom dušika ili CH po izboru supstituiran sa atomom vodika, sa halogenim atomom, ili sa C1 do C6 alkil grupom koja po izboru ima supstituent(e); kada Ar2 je A2), W2 je CH ili atom dušika; kada Ar2 je A3), A4), A5), ili A6), W3 je atom kisika, atom sumpora, ili NH po izboru supstituiran sa C1 do C6 alkil grupom; kada Ar2 je A3), A4), ili A6), W4 je CH ili atom dušika; kada Ar2 je A7), W5 je CH2, atom kisika, ili atom sumpora; kada Ar2 je A7), W6 je C=O, CH2, CF2, CHOH, NH po izboru supstituiran sa C1 do C6 alkil grupom, SO, SO2, atomom kisika, ili atomom sumpora; kada Ar2 je A8), W7 je NH po izboru supstituiran sa C1 do C6 alkil grupom ili C=O; kada Ar2 je A8), W8 je C=O sa W7 koji je NH po izboru supstituiran sa C1 do C6 alkil grupom i W8 je NH po izboru supstituiran sa C1 do C6 alkil grupom sa W7 koji je C=O; kada Ar2 je A10), W9 je atom dušika ili N=O; kada Ar2 je A1), A2), A3), A4), ili A5), R6 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, C1 do C6 alkil grupa koja po izboru ima supstituent(e), C1 do C6 alkoksi grupa koja po izboru ima supstituent(e), C1 do C6 acil grupa koja po izboru ima supstituent(e), C1 do C6 alkilsulfanil grupa koja po izboru ima supstituent(e), C1 do C6 alkilsulfinil grupa koja po izboru ima supstituent(e), C1 do C6 alkilsulfonil grupa koja po izboru ima supstituent(e), heterociklična grupa koja po izboru ima supstituent(e), -CONR10R11, ili -NR10R11, gdje, kada R6 je - CONR10R11 ili -NR10R11, R10 je atom vodika, C1 do C6 alkil grupa koja po izboru ima supstituent(e), C1 do C6 acil grupa koja po izboru ima supstituent(e), ili C1 do C6 alkilsulfonil grupa koja po izboru ima supstituent(e) i R11 je atom vodika ili C1 do C6 alkil grupa koja po izboru ima supstituent(e), ili R10 i R11 zajedno formiraju C3 do C10 heterocikloalkil grupu; kada Ar2 je A1), A2), A3), A4), A5), A6), A7), A8), A9), ili A10), R7 je atom vodika, halogen atom, C1 do C6 alkil grupa koja po izboru ima supstituent(e), ili C1 do C6 alkoksi grupa koja po izboru ima supstituent(e); kada Ar2 je A1), A7), A8), ili A10), R8 je atom vodika, halogen atom, ili C1 do C6 alkil grupa koja po izboru ima supstituent(e); kada Ar2 je A9), R9 je atom vodika ili C1 do C6 alkil grupa; kada Ar2 je A7), m je 0 ili 1; i kada Ar2 je A8), n je 0 ili 1; tako da, kada Ar2 je A1), kombinacije supstituenata R6, R7 i R8 isključuju kombinaciju atoma vodika i halogen atom.
3. Spoj u skladu sa patentnim zahtjevom 2 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje izraz "po izboru ima supstituent(e) ima značenje definirano u patentnom zahtjevu 1, i gdje u formuli (I), Ar1 je grupa odabrana iz grupe koja se sastoji od sljedećih B1), B2), B3), B4), B5), B6), B7), B8), B9), B10), B11), i B12): [Kemijska formula 3] [image] gdje, kada Ar1 je B2), B3), B7), B8), B10), B11), ili B12), R12 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, C1 do C6 alkil grupa koja po izboru ima supstituent(e), C1 do C6 alkoksi grupa koja po izboru ima supstituent(e), C3 do C6 cikloalkil grupa koja po izboru ima supstituent(e), C3 do C6 cikloalkoksi grupa koja po izboru ima supstituent(e), C1 do C6 acil grupa koja po izboru ima supstituent(e), C2 do C6 alkenil grupa koja po izboru ima supstituent(e), C2 do C6 alkinil grupa, C1 do C6 alkoksikarbonil grupa, C1 do C6 alkilsulfanil grupa koja po izboru ima supstituent(e), C1 do C6 alkilsulfinil grupa koja po izboru ima supstituent(e), C1 do C6 alkilsulfonil grupa koja po izboru ima supstituent(e), - CONR10R11, -NR10R11, ariloksi grupa, ili heterociklična grupa koja po izboru ima supstituent(e), gdje, kada R12 je -CONR10R11 ili -NR10R11, R10 je atom vodika, C1 do C6 alkil grupa koja po izboru ima supstituent(e), C1 do C6 acil grupa koja po izboru ima supstituent(e), ili C1 do C6 alkilsulfonil grupa koja po izboru ima supstituent(e) i R11 je atom vodika ili C1 do C6 alkil grupa koja po izboru ima supstituent(e), ili R10 i R11 zajedno formiraju C3 do C10 heterocikloalkil grupu; kada Ar1 je B1), R12 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, C1 do C6 alkil grupa koja po izboru ima supstituent(e), C1 do C6 alkoksi grupa koja po izboru ima supstituent(e), C3 do C6 cikloalkil grupa koja po izboru ima supstituent(e), C3 do C6 cikloalkoksi grupa koja po izboru ima supstituent(e), C1 do C6 acil grupa koja po izboru ima supstituent(e), C2 do C6 alkenil grupa koja po izboru ima supstituent(e), C2 do C6 alkinil grupa, C1 do C6 alkoksikarbonil grupa, C1 do C6 alkilsulfanil grupa koja po izboru ima supstituent(e), C1 do C6 alkilsulfinil grupa koja po izboru ima supstituent(e), C1 do C6 alkilsulfonil grupa koja po izboru ima supstituent(e), -CONR10R11, -NR10R11, ariloksi grupa, ili heterociklična grupa koja po izboru ima supstituent(e), gdje, kada R12 je - CONR10R11 ili -NR10R11, R10 je atom vodika, C1 do C6 alkil grupa koja po izboru ima supstituent(e), C1 do C6 acil grupa koja po izboru ima supstituent(e), ili C1 do C6 alkilsulfonil grupa koja po izboru ima supstituent(e) i R11 je atom vodika ili C1 do C6 alkil grupa koja po izboru ima supstituent(e), ili R10 i R11 zajedno formiraju C3 do C10 heterocikloalkil grupu, i R13 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, ili C1 do C6 alkil grupa, ili R12 i R13 mogu zajedno formirati C3 do C5 alkilen grupu ili C1 do C2 alkilendioksi grupu; kada Ar1 je B6), R13 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, ili C1 do C6 alkil grupa; kada Ar1 je B9), R14 i R15 su svaki zasebno atom vodika, halogen atom, cijano grupa, C1 do C6 alkil grupa, ili C1 do C6 alkoksi grupa; kada Ar1 je B2), jedan od W10 i W11 je atom dušika, i drugi od njih je CH ili atom dušika; kada Ar1 je B6), B7), B8), B9), B10), B11), ili B12), W12 je atom kisika, atom sumpora, ili N-R16, gdje, kada W12 je N-R16, R16 je atom vodika ili C1 do C6 alkil grupa; i kada Ar1 je B6), B7), B8), ili B9), W13 je CH ili atom dušika.
4. Spoj u skladu sa patentnim zahtjevom 3 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje izraz "po izboru ima supstituent(e)" ima značenje definirano u patentnom zahtjevu 1, i gdje kada Ar2 je A1), A2), A3), A4), ili A5), R6 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, C1 do C6 alkil grupa, C1 do C6 alkoksi grupa, halo-C1 do C6 alkoksi grupa, C1 do C6 acil grupa, C1 do C6 alkilsulfanil grupa, C1 do C6 alkilsulfinil grupa, C1 do C6 alkilsulfonil grupa, heterociklična grupa koja po izboru ima supstituent(e), -CONR10R11, ili -NR10R11, gdje, kada R6 je -CONR10R11 ili -NR10R11, R10 je atom vodika, C1 do C6 alkil grupa, C1 do C6 acil grupa, ili C1 do C6 alkilsulfonil grupa i R11 je atom vodika ili C1 do C6 alkil grupa, ili R10 i R11 zajedno formiraju C3 do C10 heterocikloalkil grupu; kada Ar2 je A1), A2), A3), A4), A5), A6), A7), A8), A9), ili A10), R7 je atom vodika, halogen atom, C1 do C6 alkil grupa, ili C1 do C6 alkoksi grupa; kada Ar2 je A1), A7), A8), ili A10), R8 je atom vodika, halogen atom, ili C1 do C6 alkil grupa; i kada Ar2 je A9), R9 je atom vodika ili C1 do C6 alkil grupa; tako da, kada Ar2 je A1), kombinacije supstituenata R6, R7 i R8 isključuju kombinaciju atoma vodika i halogenog atoma.
5. Spoj u skladu sa patentnim zahtjevom 4 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje izraz "po izboru ima supstituent(e)" ima značenje definirano u patentnom zahtjevu 1, i gdje R1 je atom vodika, hidroksi grupa, C1 do C6 alkil grupa, C1 do C6 alkoksi grupa, halo-C1 do C6 alkil grupa, hidroksi C1 do C6 alkil grupa, karboksi C1 do C6 alkil grupa, karbamoil C1 do C6 alkil grupa, mono C1 do C6 alkilkarbamoil C1 do C6 alkil grupa, di-C1 do C6 alkilkarbamoil C1 do C6 alkil grupa, aminosulfonil C1 do C6 alkil grupa, aromatična heterociklična C1 do C3 alkil grupa koja po izboru ima supstituent(e), ili fenil C1 do C3 alkil grupa koja po izboru ima supstituent(e); R2 i R3 su svaki zasebno atom vodika ili C1 do C3 alkil grupa ili zajedno formiraju C2 do C6 alkilen grupu; kada Ar1 je B2), B3), B7), B8), B10), B11), ili B12), R12 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, C1 do C6 alkil grupa, halo-C1 do C6 alkil grupa, hidroksi C1 do C6 alkil grupa, C1 do C6 alkoksi grupa, C3 do C6 cikloalkil grupa, C3 do C6 cikloalkoksi grupa, C1 do C6 acil grupa, C2 do C6 alkenil grupa, C2 do C6 alkinil grupa, C1 do C6 alkoksikarbonil grupa, C1 do C6 alkilsulfanil grupa, C1 do C6 alkilsulfinil grupa, C1 do C6 alkilsulfonil grupa, - CONR10R11, -NR10R11, ariloksi grupa, ili heterociklična grupa koja po izboru ima supstituent(e), gdje, kada R12 je -CONR10R11 ili -NR10R11, R10 je atom vodika, C1 do C6 alkil grupa, C1 do C6 acil grupa, ili C1 do C6 alkilsulfonil grupa i R11 je atom vodika ili C1 do C6 alkil grupa, ili R10 i R11 zajedno formiraju C3 do C10 heterocikloalkil grupu; kada Ar1 je B1), R12 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, C1 do C6 alkil grupa, halo-C1 do C6 alkil grupa, hidroksi C1 do C6 alkil grupa, C1 do C6 alkoksi grupa, C3 do C6 cikloalkil grupa, C3 do C6 cikloalkoksi grupa, C1 do C6 acil grupa, C2 do C6 alkenil grupa, C2 do C6 alkinil grupa, C1 do C6 alkoksikarbonil grupa, C1 do C6 alkilsulfanil grupa, C1 do C6 alkilsulfinil grupa, C1 do C6 alkilsulfonil grupa, -CONR10R11, -NR10R11, ariloksi grupa, ili heterociklična grupa koja po izboru ima supstituent(e), gdje, kada R12 je - CONR10R11 ili -NR10R11, R10 je atom vodika, C1 do C6 alkil grupa, C1 do C6 acil grupa, ili C1 do C6 alkilsulfonil grupa i R11 je atom vodika ili C1 do C6 alkil grupa, ili R10 i R11 zajedno formiraju C3 do C10 heterocikloalkil grupu, i R13 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, ili C1 do C6 alkil grupa, ili R12 i R13 mogu zajedno formirati C3 do C5 alkilen grupu ili C1 do C2 alkilendioksi grupu; i X je grupa odabrana iz grupe koja se sastoji od sljedećih a), b), i c), a) atom kisika, b) NR4, i c) NOR4, gdje, kada X je b) ili c), R4 je atom vodika, hidroksi C1 do C6 alkil grupa, fenil grupa, heterociklična grupa, ili C1 do C6 alkil grupa.
6. Spoj u skladu sa patentnim zahtjevom 5 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje u formuli (I), Ar2 je grupa odabrana iz grupe koja se sastoji od A1), A2a), A3), i A7a): [Kemijska formula 4] [image] gdje, kada Ar2 je A2a), W2 je isto kao što je definirano u patentnom zahtjevu 2 kada Ar2 je A2); kada Ar2 je A3), W4 je isto kao što je definirano u patentnom zahtjevu 2 kada Ar2 je A3); kada Ar2 je A7a), W6 je isto kao što je definirano u patentnom zahtjevu 2 kada Ar2 je A7); kada Ar2 je A1), A2a), A3), ili A7a), R7 je isto kao što je definirano u patentnom zahtjevu 4 kada Ar2 je A1), A2), A3), ili A7); kada Ar2 je A1) ili A7a), R8 je isto kao što je definirano u patentnom zahtjevu 4 kada Ar2 je A1) ili A7); kada Ar2 je A7a), m je isto kao što je definirano u patentnom zahtjevu 2 kada Ar2 je A7); kada Ar2 je A1), A2a), ili A3), R6 je atom vodika, halogen atom, cijano grupa, C1 do C6 alkil grupa, C1 do C6 alkoksi grupa, halo-C1 do C6 alkoksi grupa, C1 do C6 acil grupa, C1 do C6 alkilsulfanil grupa, C1 do C6 alkilsulfinil grupa, -CONR10R11, ili -NR10R11, gdje, kada R6 je -CONR10R11 ili -NR10R11, R10 je atom vodika, C1 do C6 alkil grupa, ili C1 do C6 acil grupa i R11 je atom vodika ili C1 do C6 alkil grupa, ili R10 i R11 mogu zajedno formirati pirolidinil grupu, piperidinil grupu, piperazinil grupu, ili morfolinil grupu; i kada Ar2 je A3), W3 je atom kisika ili atom sumpora; osiguravaju da, kada Ar2 je A1), kombinacije supstituenata R6, R7 i R8 isključuju kombinaciju atoma vodika i halogenog atoma.
7. Spoj u skladu sa patentnim zahtjevom 6 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje izraz "po izboru ima supstituent(e)" ima značenje definirano u patentnom zahtjevu 1, i gdje u formuli (I), Ar1 je grupa odabrana iz grupe koja se sastoji od B1), B2), B6a), B9a), i B9b): [image] gdje, kada Ar1 je B6a), R13 je isto kao što je definirano u patentnom zahtjevu 3 kada Ar1 je B6); kada Ar1 je B9a) ili B9b), R14 i R15 su isti kao oni definirani u patentnom zahtjevu 3 kada Ar1 je B9); kada Ar1 je B2), W10 i W11 su isti kao oni definirani u patentnom zahtjevu 3 kada Ar1 je B2); kada Ar1 je B2), R12 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, C1 do C6 alkil grupa, halo-C1 do C6 alkil grupa, hidroksi C1 do C6 alkil grupa, C1 do C6 alkoksi grupa, C3 do C6 cikloalkil grupa, C3 do C6 cikloalkoksi grupa, C1 do C6 acil grupa, C2 do C6 alkenil grupa, C1 do C6 alkoksikarbonil grupa, C1 do C6 alkilsulfanil grupa, C1 do C6 alkilsulfinil grupa, C1 do C6 alkilsulfonil grupa, -CONR10R11, -NR10R11, ariloksi grupa, ili heterociklična grupa koja po izboru ima supstituent(e), gdje, kada R12 je - CONR10R11 ili -NR10R11, R10 je atom vodika, C1 do C6 alkil grupa, ili C1 do C6 acil grupa i R11 je atom vodika ili C1 do C6 alkil grupa, ili R10 i R11 mogu zajedno formirati pirolidinil grupu, piperidinil grupu, piperazinil grupu, ili morfolinil grupu; kada Ar1 je B1), R12 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, C1 do C6 alkil grupa, halo-C1 do C6 alkil grupa, hidroksi C1 do C6 alkil grupa, C1 do C6 alkoksi grupa, C3 do C6 cikloalkil grupa, C3 do C6 cikloalkoksi grupa, C1 do C6 acil grupa, C2 do C6 alkenil grupa, C1 do C6 alkoksikarbonil grupa, C1 do C6 alkilsulfanil grupa, C1 do C6 alkilsulfinil grupa, C1 do C6 alkilsulfonil grupa, -CONR10R11, -NR10R11, ariloksi grupa, ili heterociklična grupa koja po izboru ima supstituent(e), gdje, kada R12 je - CONR10R11 ili -NR10R11, R10 je atom vodika, C1 do C6 alkil grupa, ili C1 do C6 acil grupa i R11 je atom vodika ili C1 do C6 alkil grupa, ili R10 i R11 mogu zajedno formirati pirolidinil grupu, piperidinil grupu, piperazinil grupu, ili morfolinil grupu, i R13 je atom vodika, halogen atom, hidroksi grupa, cijano grupa, ili C1 do C6 alkil grupa, ili R12 i R13 mogu zajedno formirati C3 do C5 alkilen grupu ili C1 do C2 alkilendioksi grupu; i kada Ar1 je B6a), B9a), ili B9b), W12 je atom kisika ili atom sumpora.
8. Spoj u skladu sa patentnim zahtjevom 7 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje u formuli (I), Ar2 je grupa odabrana iz grupe koja se sastoji od A1a), A2b), A3a), i A7b): [image] gdje, kada Ar2 je A1a), R6 je isto kao što je definirano u patentnom zahtjevu 6 kada Ar2 je A1); kada Ar2 je A1a) ili A7b), R8 je isto kao što je definirano u patentnom zahtjevu 4 kada Ar2 je A1) ili A7); kada Ar2 je A7b), m je isto kao što je definirano u patentnom zahtjevu 2 kada Ar2 je A7); R1 je atom vodika, hidroksi grupa, C1 do C3 alkil grupa, C1 do C3 alkoksi grupa, hidroksi C1 do C4 alkil grupa, karboksi C1 do C3 alkil grupa, karbamoil C1 do C3 alkil grupa, mono-C1 do C2 alkilkarbamoil C1 do C3 alkil grupa, ili di-C1 do C2 alkilkarbamoil C1 do C3 alkil grupa; R2 i R3 su svaki zasebno atom vodika ili C1 do C3 alkil grupa; kada X je b) ili c), R4 je atom vodika, hidroksi C1 do C4 alkil grupa, ili C1 do C3 alkil grupa; kada Ar2 je A2b) ili A3a), R6a je C1 do C3 alkoksi grupa; kada Ar2 je A1a), A2b), A3a), ili A7b), R7 je atom vodika, atom fluora, atom klora, ili C1 do C3 alkil grupa; i kada Ar2 je A7b), W6 je C=O, CH2, CF2, CHOH, ili atom kisika; tako da, kada Ar1 je A1a), kombinacije supstituenata R6, R7 i R8 isključuju kombinaciju atoma vodika i halogenog atoma.
9. Spoj u skladu sa patentnim zahtjevom 8 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje u formuli (I), Ar2 je grupa odabrana iz grupe koja se sastoji od A1a), A2b), i A7c): [image] gdje, kada Ar2 je A2b), R6a je isto kao što je definirano u patentnom zahtjevu 8 kada Ar2 je A2b); kada Ar2 je A1a) ili A7c), R8 je isto kao što je definirano u patentnom zahtjevu 4 kada Ar2 je A1) ili A7); kada Ar2 je A7c), m je isto kao što je definirano u patentnom zahtjevu 8 kada Ar2 je A7b); kada Ar2 je A1a), R6 je atom vodika, atom fluora, atom klora, cijano grupa, C1 do C6 alkil grupa, C1 do C6 alkoksi grupa, halo-C1 do C6 alkoksi grupa, C1 do C6 alkilsulfanil grupa, C1 do C6 alkilsulfinil grupa, ili -CONR10R11, gdje, kada R6 je -CONR10R11, R10 je atom vodika, C1 do C6 alkil grupa, ili C1 do C6 acil grupa i R11 je atom vodika ili C1 do C6 alkil grupa, ili R10 i R11 mogu zajedno formirati pirolidinil grupu, piperidinil grupu, piperazinil grupu, ili morfolinil grupu; i kada Ar2 je A1a), A2b), ili A7c), R7 je atom vodika, atom fluora, ili atom klora; tako da, kada Ar2 je A1a), kombinacije supstituenata R6, R7 i R8 isključuju kombinaciju atoma vodika i halogenog atoma.
10. Spoj u skladu sa patentnim zahtjevom 9 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje u formuli (I), Ar1 je grupa odabrana iz grupe koja se sastoji od B1), B2), B6b), B9c), i B9d): [image] gdje R1 je atom vodika, hidroksi grupa, C1 do C3 alkil grupa, C1 do C3 alkoksi grupa, ili hidroksi C1 do C4 alkil grupa; kada Ar1 je B1) ili B2), R12 je atom vodika, atom fluora, atom klora, cijano grupa, C1 do C3 alkil grupa, ili C1 do C6 alkoksi grupa; kada Ar1 je B1) ili B6b), R13 je atom vodika, hidroksi grupa, atom fluora, ili atom klora; kada Ar1 je B9c) ili B9d), R14 je atom vodika, atom fluora, atom klora, C1 do C3 alkil grupa, metoksi grupa, ili etoksi grupa; kada Ar1 je B9c) ili B9d), R15 je atom vodika, atom fluora, ili atom klora; i kada Ar1 je B2), jedan od W10 i W11 je N, i drugi od njih je CH.
11. Spoj u skladu sa patentnim zahtjevom 10 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje u formuli (I), Ar1 je grupa odabrana iz grupe koja se sastoji od B1), B6b), i B9c1): [image] gdje kada Ar1 je B1), R12 je isto kao što je definirano u patentnom zahtjevu 10 kada Ar1 je B1); kada Ar1 je B1) ili B6b), R13 je isto kao što je definirano u patentnom zahtjevu 10 kada Ar1 je B1) ili B6b); i kada Ar1 je B9c1), R14 je isto kao što je definirano u patentnom zahtjevu 10 kada Ar1 je B9c).
12. Spoj u skladu sa patentnim zahtjevom 11 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje u formuli (I), Ar2 je grupa odabrana iz grupe koja se sastoji od A1b), A2b), i A7c): [image] gdje, kada Ar2 je A2b), R6a je isto kao što je definirano u patentnom zahtjevu 8 kada Ar2 je A2b); kada Ar2 je A7c), m je isto kao što je definirano u patentnom zahtjevu 8 kada Ar2 je A7b); kada Ar2 je A1b), R6 je cijano grupa, etil grupa, ili C1 do C3 alkoksi grupa; R7 je atom fluora ili atom klora; i kada Ar2 je A1 b) ili A7c), R8 je atom vodika, atom fluora, atom klora, ili C1 do C3 alkil grupa.
13. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje spoj predstavljen formulom (1) je (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-(4-klorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-(3,4-difluorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-(4-cijanofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-(4-klorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-1-metil-2-oksopirolidin-3-il]urea, (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-1-metil-2-oksopirolidin-3-il]urea, (-)-1-[(3S*,4R*)-4-(3-fluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-[(3S*,4R*)-4-(2-fluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, 1-[(3S*,4R*)-4-(2-kloro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-4-(4-metoksi-2-metilfenil)-2-oksopirolidin-3-il]urea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-[(3S*,4R*)-4-(2,5-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-[(3S*,4R*)-4-(3,5-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-[(3S*,4R*)-4-(6-fluoro-2,3-dihidrobenzofuran-5-il)-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-[(3S*,4R*)-4-(3-fluoro-5-metoksipiridin-2-il)-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-4-(5-metoksitiofen-2-il)-2-oksopirolidin-3-il]urea, (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-4-(4-metiltiofenil)-2-oksopirolidin-3-il]urea, (-)-1-(4-klorofenil)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-(4-cijanofenil)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-metoksifenil)urea, (-)-1-(5-klorotiazol-2-il)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-(6-kloropiridin-3-il)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-(5-kloropiridin-2-il)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-(benzo[b]tiofen-2-il)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(5-metiltiofen-2-il)urea, (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-5-metil-2-oksopirolidin-3-il]urea, (-)-1-(4-fluorofenil)-3-[(3S*,4R*,5R*)-4-(4-metoksifenil)-5-metil-2-oksopirolidin-3-il]urea, (+)-1-(4-klorofenil)-3-[(3S*,4R*)-2-okso-4-fenilpirolidin-3-il]urea, (±)-trans-1-(4-klorofenil)-3-[4-(4-metoksifenil)-1-metil-2-oksopirolidin-3-il]urea, (±)-trans-1-(4-fluorofenil)-3-[4-(4-metoksifenil)-2-oksopirolidin-3-il]urea, (±)-trans-1-(4-klorofenil)-3-[4-(4-metoksifenil)-1-metil-2-oksopirolidin-3-il]urea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-[4-(trifluorometoksi)fenil]urea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-fenilurea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fenoksifenil)urea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(3-fluorofenil)urea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(3,4-difluorofenil)urea, (-)-1-(5-klorotiofen-2-il)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(p-tolil)urea, (-)-1-[(3S*,4R*)-1-etil-4-(4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-1-(1-hidroksi-2-metilpropan-2-il)-4-(4-metoksifenil)-2-oksopirolidin-3-il]urea, (±)-trans-1-(4-klorofenil)-3-[1-(2-hidroksietil)-4-(4-metoksifenil)-2-oksopirolidin-3-il]urea, (+)-trans-1-(4-klorofenil)-3-[1-(2-hidroksietil)-4-(4-metoksifenil)-2-oksopirol idin-3-il]urea, (-)-trans-1-(4-klorofenil)-3-[1-(2-hidroksietil)-4-(4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-2-{(3S*,4R*)-3-[3-(4-fluorofenil)ureido]-4-(4-metoksifenil)-2-oksopirolidin-1-il}-N-metilacetamid, (-)-2-{(3S*,4R*)-3-[3-(4-fluorofenil)ureido]-4-(4-metoksifenil)-2-oksopirolidin-1-il}propionska kiselina (izomer A), (-)-2-{(3S*,4R*)-3-[3-(4-fluorofenil)ureido]-4-(4-metoksifenil)-2-oksopirolidin-1-il}-N-metilpropionamid (izomer A), (-)-2-{(3S*,4R*)-3-[3-(4-fluorofenil)ureido]-4-(4-metoksifenil)-2-oksopirolidin-1-il}propionska kiselina (izomer B), (-)-2-{(3S*,4R*)-3-[3-(4-fluorofenil)ureido]-4-(4-metoksifenil)-2-oksopirolidin-1-il}-N-metilpropionamid (izomer B), (-)-2-{(3S*,4R*)-3-[3-(4-fluorofenil)ureido]-4-(4-metoksifenil)-2-oksopirolidin-1-il}-N,2-dimetilpropionamid, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-1-metil-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-[(3S*,4R*)-4-(2-fluoro-4-metoksifenil)-1-(2-hidroksietil)-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-1-(2-hidroksietil)-2-oksopirolidin-3-il]-3-(4-fluorofenil)urea, (+)-1-(4-fluorofenil)-3-[(3R*,4S*)-1-metoksi-4-(4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-3,5-difluoro-4-{(3R*,4R*)-4-[3-(4-fluorofenil)ureido]-5-oksopirolidin-3-ilbenzamid, (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-2-(metoksiimino)-4-(4-metoksifenil)pirolidin-3-il]urea, (-)-1-[(3S*,4R*)-4-(2-fluoro-4-metoksifenil)-2-(metoksiimino)pirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-[(3S*,4R*,Z)-4-(2,6-difluoro-4-metoksifenil)-2-(metoksiimino)pirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-(4-fluorofenil)-3-{(3S*,4R*,Z)-2-[(2-hidroksietoksi)imino]-4-(4-metoksifenil)pirolidin-3-il}urea, (-)-1-{(3S*,4R*,Z)-4-(2,6-difluoro-4-metoksifenil)-2-[(2-hidroksietoksi)imino]pirolidin-3-il}-3-(4-fluorofenil)urea, (-)-1-[(3S*,4R*,Z)-4-(2,6-difluoro-4-metoksifenil)-2-(metilimino)pirolidin-3-il]-3-(4-fluorofenil)urea, (-)-1-(4-fluorofenil)-3-[(3S*,4R*,Z)-2-(2-hidroksiimino)-4-(4-metoksifenil)pirolidin-3-il]urea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(3-hidroksi-4-metilfenil)urea, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluoro-3-hidroksifenil)urea, (-)-1-(4-kloro-3-hidroksifenil)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]urea, (-)-1-(4-cijanofenil)-3-[(3S*,4R*)-4-(6-fluoro-2,3-dihidrobenzofuran-5-il)-2-oksopirolidin-3-il]urea, (-)-1-{(3S*,4R*,Z)-4-(2,6-difluoro-4-metoksifenil)-2-[(2-hidroksietoksi)imino]pirolidin-3-il}-3-(p-tolil)urea, ili (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-1-(2-hidroksietil)-2-oksopirolidin-3-il]-3-fenilurea.
14. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
15. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
16. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
17. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
18. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
19. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
20. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
21. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
22. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
23. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
24. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
25. Spoj u skladu sa patentnim zahtjevom 1 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, gdje je spoj: [image]
26. Farmaceutski preparat koji sadrži, kao aktivni sastojak, spoj u skladu sa bilo kojim od patentnih zahtjeva 1 do 25 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat.
27. Farmaceutska kompozicija koja sadrži spoj u skladu sa bilo kojim od patentnih zahtjeva 1 do 25 ili njegova farmakološki prihvatljiva sol, ili njegov solvat ili hidrat, i farmaceutski prihvatljiv nosač, za primjenu u prevenciji ili liječenju upalnih bolesti, kroničnih bolesti dišnih puteva, raka, septikemije, alergijskih simptoma, HIV retrovirus infekcije, poremećaja cirkulacije, neuroinflamacije, nervnih poremećaja, bolova, prionskih bolesti, amiloidoze, i imunoloških poremećaja.
HRP20180199TT 2013-11-28 2018-02-02 Urea derivati ili njihove farmakološki prihvatljive soli korisni kao agonisti formil peptidnom receptoru-sličnom i (fprl-1) HRP20180199T1 (hr)

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EP14865553.3A EP3075726B1 (en) 2013-11-28 2014-11-27 Urea derivatives or pharmacologically acceptable salts thereof useful as formyl peptide receptor like 1 (fprl-1) agonists
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