SI3075726T1 - Derivati sečnine ali njenih farmakološko sprejemljivih soli uporabnih kot formil peptidni receptor podobnih 1 (fprl-1) agonistov - Google Patents

Derivati sečnine ali njenih farmakološko sprejemljivih soli uporabnih kot formil peptidni receptor podobnih 1 (fprl-1) agonistov Download PDF

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SI3075726T1
SI3075726T1 SI201430579T SI201430579T SI3075726T1 SI 3075726 T1 SI3075726 T1 SI 3075726T1 SI 201430579 T SI201430579 T SI 201430579T SI 201430579 T SI201430579 T SI 201430579T SI 3075726 T1 SI3075726 T1 SI 3075726T1
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optionally
substituent
urea
alkyl group
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SI201430579T
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Hiroyasu Takahashi
Yoshifumi Saito
Kosuke Tsuda
Mitsuhito Shibasaki
Kohei Ohata
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Kyorin Pharmaceutical Co., Ltd.
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Publication of SI3075726T1 publication Critical patent/SI3075726T1/sl

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Claims (27)

  1. DERIVATI SEČNINE ALI NJENIH FARMAKOLOŠKO SPREJEMLJIVIH SOLI UPORABNIH KOT FORMIL PEPTIDNI RECEPTOR PODOBNIH 1 (FPRL-1) AGONISTOV EP 3 075 726 B1 PATENTNI ZAHTEVKI
    1. Spojina, prikazana s splošno formulo (I), ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat [Chemical Formula 1]
    (I) kjer je v formuli (I) Ar1 fenilna skupina, ki ima po izbiri substituent (e), 5-členska aromatska heterociklično skupina, ki ima po izbiri substituent (e), 6-členska aromatska heterociklična skupina, ki ima po izbiri substituent (e) ali biciklična aromatska heterociklična skupina z 8 ali 9 atomi in po izbiri ima substituent (e); Ar2 je fenilna skupina, ki ima po izbiri substituent(e) (razen fenilne skupine, substituirane samo z atomi halogena), 5-členska aromatska heterociklična skupina, ki ima po izbiri substituent(e), 6-členska aromatska heterociklična skupina, ki ima po izbiri substituent(e) ali biciklična aromatska heterociklična skupina z 8 ali 9 atomi in po izbiri ima substituent(e); X je skupina, izbrana iz skupine, ki jo sestavljajo naslednji: a), b) in c), a) kisikov atom ali atom žvepla, b) NR4 in c) NOR4, kjer, kadar je X b) ali c), je R4 atom vodika, fenilna skupina, ki ima po izbiri substituent(e), heterociklična skupina, ki ima po izbiri substituent(e) ali Ci do Ce alkilna skupina, ki ima po izbiri substituent(e); R1 je atom vodika, hidroksi skupina, Ci do Ce alkoksi skupina, ki ima po izbiri substituent (e) ali Ci do C6 alkilna skupina, ki ima po izbiri substituent (e); R2 in R3 sta vsak neodvisno atom vodika ali Ci do C6 alkilna skupina, ki ima po izbiri substituent(e) ali skupaj tvorita C2 do Οβ alkilensko skupino; in vsak atom ogljika, označen z zvezdico, je asimetrični atom ogljika; pri čemer izraz "po izbiri ima substituent(e)" pomeni po izbiri substituiran z enim ali večimi substituenti, izbranimi iz skupine, ki jo sestavljajo: atomi halogena, amino skupina, hidroksi skupina, dano skupina, nitro skupina, karboksi skupina, Ci do C6 alkoksikarbonilne skupine, formilna skupina, Ci do Ce acilne skupine, Ci do C6 alkilne skupine, Ci do Οβ alkilamino skupine , di-Ci do Οβ alkilamino skupine, Ci do Οβ alkoksi skupine, Ci do Ce alkiltio skupine, C3 do Ce cikloalkilne skupine, 4- do 10-členske heterocikloalkilne skupine, ciklične skupine z aromatskimi ogljikovodiki, ki imajo po izbiri atom halogena, aromatske heterociklične skupine, Ci do Ce alkilkarbonilamino skupine, C3 do C6 cikloalkilkarbonilamino skupine, 4- do 10-členske heterocikloalkilkarbonilamino skupine, aromatske ogljikovodikove ciklične karbonilamino skupine in aromatske heterociklične karbonilamino skupine, s pridržkom, da kadar ima skupina opcijsko substituent(e), so izbrani iz skupine, ki jo sestavljajo fenil, 5-členska aromatska heterociklična skupina, 6-členska aromatska heterociklična skupina, biciklična aromatska heterociklična skupina z 8 ali 9 atomi in heterociklična skupina, po izbiri substituent ni di-Ci do C6 alkilamino skupina.
  2. 2. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer ima izraz "po izbiri ima substituent(e)" pomen, definiran v zahtevku 1, in kjer je v formuli (I) Ar2 skupina, izbrana iz skupine, ki jo sestavljajo naslednji A1), A2), A3), A4), A5), A6), A7), A8), A9) in Α10): [Chemical Formula 2]
    kjer, kadar je Ar2 A2), je W1 atom dušika ali CH, po izbiri substituiran z atomom vodika, z atomom halogena ali s Ci do C6 alkilno skupino, ki ima po izbiri substituent(e); kadar je Ar2 A2), je VV2 CH ali atom dušika; kadar je Ar2 A3), A4), A5) ali A6), je W3 atom kisika, atom žvepla ali NH, po izbiri substituiran s Ci do Ce alkilno skupino; kadar je Ar2 A3), A4) ali A6), je W4 CH ali atom dušika; kadar je Ar2 A7), je W5 CH2, atom kisika ali atom žvepla; kadar je Ar2 A7), je W6 C = O, CH2, CF2, CHOH, NH, po izbiri substituiran s C1 do Ce alkilno skupino, SO, SO2, atomom kisika ali atomom žvepla; kadar je Ar2 A8), je W7 NH, po izbiri substituiran s C1 do C6 alkilno skupino ali C = O; kadar je Ar2 A8), je W8 C = O, pri čemer je W7 NH, po izbiri substituiran s C1 do C6 alkilno skupino in je W8 NH, po izbiri substituiran s C1 do C6 alkilno skupino, pri čemer je W7 C = O; kadar je Ar2 A10), je W9 atom dušika ali N = O; kadar je Ar2 A1), A2), A3), A4) ali A5), je R6 atom vodika, atom halogena, hidroksi skupina, ciano skupina, C1 do C6 alkilna skupina, ki ima po izbiri substituent(e) C1 do C6 alkoksi skupina, ki ima po izbiri substituent(e), C1 do Ce acilna skupina, ki ima po izbiri substituent(e), C1 do C6 alkilsulfanilna skupina, ki ima po izbiri substituent(e), C1 do C6 alkilsulfinilna skupina, ki ima po izbiri substituent(e), C1 do C6 alkilsulfonilna skupina, ki ima po izbiri substituent(e), heterociklična skupina, ki ima po izbiri substituent(e), -CONR10R11 ali -NR10R11, kjer kadar je R6-CON10R11 ali -NR10R11 , R10 je atom vodika, C1 do C6 alkilna skupina, ki ima po izbiri substituent (e), C1 do C6 acilna skupina, ki ima po izbiri substituent (e) ali C1 do C6 alkilsulfonilna skupina, ki ima po izbiri substituent(e) in je R11 atom vodika ali C1 do C6 alkil skupina, ki ima po izbiri substituent(e), ali R10 in R11 skupaj tvorita C3 do C10 heterocikloalkilno skupino; kadar je Ar2 A1), A2), A3), A4), A5), A6), A7), A8), A9) ali A10), je R7 atom vodika, atom halogena, Ci do C6 alkilna skupina, ki ima po izbiri substituent(e), ali Ci do C6 alkokis skupina, ki ima po izbiri substituent (e); kadar je Ar2 A1), A7), A8) ali A10), je R8 atom vodika, atom halogena ali Ci do Ce alkilna skupina, ki ima po izbiri substituent(e); kadar je Ar2 A9), je R9 atom vodika ali Ci do Ce alkilna skupina; kadar je Ar2 A7), je m 0 ali 1; in kadar je Ar2 A8), je n 0 ali 1; pod pogojem, da kadar je Ar2 A1), kombinacije substituentov R6, R7 in R8 izključujejo kombinacijo vodikovega atoma in atoma halogena.
  3. 3. Spojina po zahtevku 2 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, pri čemer ima izraz "po izbiri substituent(e)" pomen, kot je definiran v zahtevku 1, in kjer je v formuli (I) Ar1 skupina, izbrana iz skupine, ki jo sestavljajo naslednji B1), B2), B3), B4), B5), B6), B7), B8), B9), B10), B11) in Β12): [Chemical Formula 31
    kadar je Ar1 B2), B3), B7), B8), B10), B11) ali B12), je R12 atom vodika, atom halogena, hidroksi skupina, ciano skupina, Ci do Ce alkilna skupina, ki ima po izbiri substituent(e), Ci do Οθ alkoksi skupina, ki ima po izbiri substituent(e), C3 do Ce cikloalkilna skupina, ki ima po izbiri substituent (e), C3 do C6 cikloalkoksi skupina, ki ima po izbiri substituent(e), Ci do C6 acilna skupina, ki ima po izbiri substituent(e), C2 do Ce alkenilna skupina, ki ima po izbiri substituent(e), C2 do Οβ alkinilna skupina, Ci do Οβ alkoksikarbonilna skupina, Ci do Οβ alkilsulfanilna skupina, ki ima po izbiri substituent(e), Ci do Οβ alkilsulfinilna skupina, ki ima po izbiri substituent (e), Ci do Ce alkilsulfonilna skupina, ki ima po izbiri substituent(e), -CONR10R11, -NR10R11, ariloksi skupina ali heterociklična skupina, ki ima po izbiri substituent(e), kjer je, kadar je R12 -CONR10R11 ali -NR10R11, je R10 atom vodika, Ci do C6 alkilna skupina, ki ima po izbiri substituent(e), Ci do C6 acilna skupina, ki ima po izbiri substituent(e), ali Ci do Οβ alkilsulfonilna skupina, ki ima po izbiri substituent(e) in je R11 atom vodika ali Ci do C6 alkilna skupina, ki ima po izbiri substituent(e), ali R10 in R11 skupaj tvorita C3 do C10 heterocikloalkilno skupino; kadar je Ar1 B1), je R12 atom vodika, atom halogena, hidroksi skupina, ciano skupina, Ci do C6 alkilna skupina, ki ima po izbiri substituent(e), Ci do Ce alkoksi skupina, ki ima po izbiri substituent(e), C3 do C6 cikloalkilna skupina, ki ima po izbiri substituent(e), C3 do Ce cikloalkoksi skupina, ki ima po izbiri substituent(e), Ci do C6 acilna skupina, ki ima po izbiri substituent(e), C2 do C6 alkenilna skupina, ki ima po izbiri substituent(e), C2 do C6 alkinilna skupina, Ci do C6 alkoksikarbonilna skupina, Ci do C6 alkilsulfanilna skupina, ki ima po izbiri substituent(e), Ci do C6 alkilsulfinilna skupina, ki ima po izbiri substituent(e), Ci do C6 alkilsulfonilna skupina, ki ima po izbiri substituent(e), -CONR10R11, -NR10R11, ariloksi skupina ali heterociklična skupina, ki ima po izbiri substituent (e), kadar je R12-CONR10R11 ali -NR10R11, R10je atom vodika, Ci do Ce alkilna skupina, ki ima po izbiri substituent(e), Ci do C6 acilna skupina, ki ima po izbiri substituent(e) ali Ci do C6 alkilsulfonilna skupina, ki ima po izbiri substituent(e) in je R11 atom vodika ali Ci do C6 alkilna skupina, ki ima po izbiri substituent(e) ali R10 in R11 skupaj tvorita C3 do C10 heterocikloalkilno skupino in R13 je atom vodika, atom halogena, hidroksi skupina, ciano skupina ali Ci do Ce alkilna skupina ali R12 in R13 lahko skupaj tvorita C3 do C5 alkilensko skupino ali Ci do C2 alkilendioksi skupino; kadar je Ar1 B6), je R13 atom vodika, atom halogena, hidroksi skupina, ciano skupina ali Ci do C6 alkilna skupina; kadar je Ar1 B9), sta R14 in R15 vsak neodvisno atom vodika, atom halogena, ciano skupina, Ci do C6 alkilna skupina ali Ci do C6 alkoksi skupina; kadar je Ar1 B2), je eden od W10 in W11 atom dušika, drugi od njiju je CH ali atom dušika; kadar je Ar1 B6), B7), B8), B9), B10), B11) ali B12), je W12 atom kisika, atom žvepla ali N-R16, kadar je W12 N-R16, je R16 atom vodika ali Ci do C6 alkilna skupina; in kadar je Ar1 B6), B7), B8) ali B9), je W13 CH ali atom dušika.
  4. 4. Spojina po zahtevku 3 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, pri čemer ima izraz "po izbiri substituent(e)" pomen, kot je definiran v zahtevku 1, in kjer kadar je Ar2 A1), A2), A3), A4) ali A5), je R6 je atom vodika, atom halogena, hidroksi skupina, ciano skupina, Ci do C6 alkilna skupina, Ci do C6 alkoksi skupina, halo-Ci do Ce alkoksi skupina, Ci do Ce acilna skupina, Ci do Ce alkilsulfanilna skupina, Ci do Ce alkilsulfinilna skupina, Ci do Ce alkilsulfonilna skupina, heterociklična skupina, ki ima po izbiri substituent (e), -CONR10R11 ali -NR10R11, kjer je, kadar je R6 -CONR10R11 ali -NR10R11, je R10 atom vodika, Ci do C6 alkilna skupina, Ci do Ce acilna skupina ali Ci do C6 alkilsulfonilna skupina in R11 je atom vodika ali Ci do C6 alkilna skupina ali R10 in R11 skupaj tvorita C3 do C10 heterocikloalkilno skupino; kadar je Ar2 A1), A2), A3), A4), A5), A6), A7), A8), A9) ali A10), je R7 atom vodika, atom halogena, Ci do C6 alkilna skupina ali Ci do C6 alkoksi skupina; kadar je Ar2 A1), A7), A8) ali A10), je R8 je atom vodika, atom halogena ali Ci do C6 alkilna skupina; in kadar je Ar2 A9), je R9 atom vodika ali Ci do C6 alkilna skupina; pod pogojem, da kadar je Ar2 A1), kombinacije substituentov R6, R7 in R8 izključujejo kombinacijo atoma vodika in atoma halogena.
  5. 5. Spojina po zahtevku 4 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, pri čemer ima izraz "po izbiri substituent (e)" pomen, kot je definiran v zahtevku 1, in kjer je R1 vodikov atom, hidroksi skupina, Ci do C6 alkilna skupina, Ci do Ce alkoksi skupina, halo-Ci do Ce alkilna skupina, hidroksi Ci do C6 alkilna skupina, karboksi Ci do C6 alkilna skupina, karbamoil Ci do C6 alkilna skupina, mono Ci do C6 alkilkarbamoil Ci do C6 alkilna skupina, di-Ci do C6 alkilkarbamoil Ci do C6 alkilna skupina, aminosulfonil Ci do C6 alkilna skupina, aromatska heterociklična Ci do C3 alkilna skupina, ki ima po izbiri substituent(e) ali fenilno C1 do C3 alkilna skupina, ki ima po izbiri substituent (e); R2 in R3 sta vsak neodvisno atom vodika ali C1 do C3 alkilna skupina ali skupaj tvorita C2 do C6 alkilensko skupino; kadar je Ar1 B2), B3), B7), B8), B10), B11) ali B12), je R12je atom vodika, atom halogena, hidroksi skupina, ciano skupina, C1 do C6 alkilna skupina, halo-Ci do C6 alkilna skupinao, hidroksi C1 do C6 alkilna skupina, C1 do C6 alkoksi skupina, C3 do Ce cikloalkilna skupina, C3 do C6 cikloalkoksi skupina, C1 do C6 acilna skupina, C2 do Ce alkenilna skupina, C2 do C6 alkinilna skupina, C1 do C6 alkoksikarbonilna skupina, C1 do Ce alkilsulfanilna skupina, C1 do C6 alkilsulfinilna skupina, C1 do C6 alkilsulfonilna skupina, - CONR10R11, -NR10R11, ariloksi skupina ali heterociklična skupina, ki ima po izbiri substituent(e), pri čemer je, kadar je R12 -CONR10R11 ali -NR10R11, je R10 atom vodika, C1 do Ce alkilna skupina, C1 do Ce acilna skupina ali C1 do Ce alkilsulfonilna skupina in R11 je atom vodika ali C1 do C6 alkilna skupina, ali R10 in R11 skupaj tvorita C3 do C10 heterocikloalkilno skupino; kadar je Ar1 B1), je R12 atom vodika, atom halogena, hidroksi skupina, ciano skupina, C1 do C6 alkilna skupina, halo-Ci do C6 alkilna skupina, hidroksi C1 do C6 alkilna skupina, C1 do C6 alkoksi skupina, C3 do Ce cikloalkilna skupina, C3 do C6 cikloalkoksi skupina, C1 do C6 acilna skupina, C2 do Οβ alkenilna skupina, C2 do C6 alkinilna skupina, C1 do C6 alkoksikarbonilna skupina, C1 do C6 alkilsulfanilna skupina, C1 do C6 alkilsulfinilna skupina, C1 do C6 alkilsulfonilna skupina, -CONR10R11, -NR10R11, ariloksi skupina ali heterociklična skupina, ki ima po izbiri substituent(e), pri čemer, kadar je R12 -CONR10R11 ali -NR10R11, je R10 atom vodika, C1 do C6 alkilna skupina, C1 do C6 acilna skupina ali C1 do C6 alkilsulfonilna skupina in je R11 atom vodika ali Ci do Ce alkilna skupina ali R10 in R11 skupaj tvorita C3 do C10 heterocikloalkilno skupino in je R13 atom vodika, atom halogena, hidroksi skupina, ciano skupina ali C1 do C6 alkilna skupina, ali R12 in R13 lahko skupaj tvorita C3 do Cs alkilensko skupino ali C1 do C2 alkilendioksi skupino; in X je skupina, izbrana iz skupine, ki jo sestavljajo naslednji: a), b) in c) a) atom kisika, b) NR4 in c) NOR4, kjer, kadar X je b) ali c), je R4 atom vodika, hidroksi C1 do Ce alkilna skupina, fenilna skupina, heterociklična skupina ali C1 do C6 alkilna skupina.
  6. 6. Spojina po zahtevku 5 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je v formuli (I) Ar2 skupina, izbrana iz skupine, ki jo sestavljajo A1), A2a), A3) in A7a): [Chemical Formula 4]
    kjer, kadar je Ar2 A2a), je W2 enak kot je definiran v zahtevku 2, kadar je Ar2 A2); kadar je Ar2 A3), je W4 enak tistemu, kot je definiran v zahtevku 2, kadar je Ar2 A3); kadar je Ar2 A7a), je W® enak tistemu, kot je definiran v zahtevku 2, kadar je Ar2 A7); kadar je Ar2 A1), A2a), A3) ali A7a), je R7 enak, kot je definiran v zahtevku 4, kadar je Ar2 A1), A2), A3) ali A7); kadar je Ar2 A1) ali A7a), je R8 enak kot je definiran v zahtevku 4, kadar je Ar2 A1) ali A7); kadar je Ar2 A7a), je m enak kot je definiran v zahtevku 2, kadar je Ar2 A7); kadar je Ar2 A1), A2a) ali A3), je R6 atom vodika, atom halogena, ciano skupina, Ci do C6 alkilna skupina, Ci do Ce alkoksi skupina, halo-Ci do Ce alkoksi skupina, Ci do Ce acilna skupina, Ci do Οβ alkilsulfanilna skupina, Ci do C6 alkilsulfinilna skupina, -CONR10R11 ali -NR10R11, kjer, kadar je R6 -CONR10R11 ali -NR10R11, je R10 atom vodika, Ci do C6 alkilna skupina ali Ci do Ce acilna skupina in R11 je atom vodika ali Ci do C6 alkilna skupina ali R10 in R11 skupaj lahko tvorita pirolidinilno skupino, piperidinilno skupino, piperazinilno skupino ali morfolinilno skupino; in kadar je Ar2 A3), je W3 atom kisika ali atom žvepla; pod pogojem, da kadar je Ar2 A1), kombinacije substituentov R6, R7 in R8 izključujejo kombinacijo atom vodika in atom halogena.
  7. 7. Spojina po zahtevku 6 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, pri čemer ima izraz "po izbiri substituent(e)" pomen, kot je definiran v zahtevku 1, in kjer je v formuli (I) Ar1 skupina, izbrana iz skupine, ki jo sestavljajo B1), B2), B6a), B9a) in B9b); [Chemical Formula 5]
    kjer, kadar je Ar1 B6a), je R13 enak kot je definiran v zahtevku 3, kadar je Ar1 B6); kadar je Ar1 B9a) ali B9b), sta R14 in R15 enaka tistima, ki sta definirana v zahtevku 3, kadar je Ar1 B9); kadar je Ar1 B2), sta W10 in W11 enaka tistima, ki sta definirana v zahtevku 3, kadar je Ar1 B2); kadar je Ar1 B2), je R12 atom vodika, atom halogena, hidroksi skupina, ciano skupina, Ci do C6 alkilna skupina, halo-Ci do C6 alkilna skupina, hidroksi Ci do C6 alkilna skupina, Ci do C6 alkoksi skupina, C3 do C6 cikloalkilna skupina, C3 do C6 cikloalkoksi skupina, Ci do Ce acilna skupina, C2 do Οβ alkenilna skupina, Ci do Ce alkoksikarbonilna skupina, Ci do C6 alkilsulfanilna skupina, Ci do C6 alkilsulfinilna skupina, Ci do C6 alkilsulfonilna skupina, -CONR10R11, -NR10R11, ariloksi skupina ali heterociklična skupina, ki ima po izbiri substituent(e), kjer, kadar je R12 -CONR10R11 ali -NR10R11, je R10 atom vodika, Ci do C6 alkilna skupina ali Ci do C6 acilna skupina in R11 je atom vodika ali Ci do Ce alkilna skupina ali R10 in R11 lahko skupaj tvorita pirolidinilno skupino, piperidinilno skupino, piperazinilno skupino ali morfolinilno skupino; kadar je Ar1 B1), je R12 atom vodika, atom halogena, hidroksi skupina, ciano skupina, Ci do C6 alkilna skupina, halo-Ci do C6 alkilna skupina, hidroksi Ci do Οβ alkilna skupina, Ci do Ce alkoksi skupina, C3 do C6 cikloalkilna skupina, C3 do C6 cikloalkoksi skupina, Ci do C6 acilna skupina, C2 do Ce alkenilna skupina, Ci do C6 alkoksikarbonilna skupina, Ci do C6 alkilsulfanilna skupina, Ci do C6 alkilsulfinilna skupina, Ci do C6 alkilsulfonilna skupina, -CONR10R11, -NR10R11, ariloksi skupina ali heterociklična skupina, ki ima po izbiri substituent(e), kjer, kadar je R12 - CONR10R11 ali -NR10R11, je R10 atom vodika, Ci do Ce alkilna skupina ali Ci do Ce acilna skupina in je R11 atom vodika ali Ci do Ce alkilna skupina ali R10 in R11 lahko skupaj tvorita pirolidinilno skupino, piperidinilno skupino, piperazinilno skupino ali morfolinilno skupino in je R13 atom vodika, atom halogena, hidroksi skupina, ciano skupina ali Ci do C6 alkilna skupina ali R12 in R13 lahko skupaj tvorita C3 do Cs alkilensko skupino ali Ci do C2 alkilendioksi skupino; in kadar je Ar1 B6a), B9a) ali B9b), je W12 je atom kisika ali atom žvepla.
  8. 8. Spojina po zahtevku 7 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer v formuli (I) je Ar2 skupina, izbrana iz skupine, ki jo sestavljajo A1a), A2b), A3a) in A7b): [Chemical Formula 6]
    kjer, kadar je Ar2 A1a), je R6 enak kot je definiran v zahtevku 6, kadar je Ar2 A1); kadar je Ar2 A1a) ali A7b), je R8 enak, kot je definiran v zahtevku 4, kadar je Ar2 A1) ali A7); kadar je Ar2 A7b), je m enak kot je definiran v zahtevku 2, kadar je Ar2 A7); R1 je atom vodika, hidroksi skupina, Ci do C3 alkilna skupina, Ci do C3 alkoksi skupina, hidroksi Ci do C4 alkilna skupina, karboksi Ci do C3 alkilna skupina, karbamoil Ci do C3 alkilna skupina, mono-Ci do C2 alkilkarbamoil C1 do C3 alkilna skupina ali di-Ci do C2 alkilkarbamoil C1 do C3 alkilna skupina; R2 in R3 sta vsak neodvisno atom vodika ali C1 do C3 alkilna skupina; kadar je X b) ali c), je R4 atom vodika, hidroksi C1 do C4 alkilna skupina ali C1 do C3 alkilna skupina; kadar je Ar2 A2b) ali A3a), je R6a C1 do C3 alkoksi skupina; kadar je Ar2 A1a), A2b), A3a) ali A7b), je R7 je atom vodika, atom fluora, atom klora ali C1 do C3 alkilna skupina; in kadar je Ar2 A7b), je W6 C = O, CH2, CF2, CHOH ali atom kisika; pod pogojem, da kadar je Ar1 A1a), kombinacije substituentov R6, R7 in R8 izključujejo kombinacijo atoma vodika in atoma halogena.
  9. 9. Spojina po zahtevku 8 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer v formuli (I) je Ar2 skupina, izbrana iz skupine, ki jo sestavljajo A1a), A2b) in A7c [Chemical Formula 7]
    kjer, kadar je Ar2 A2b), je R6a enak kot je definiran v zahtevku 8, kadar je Ar2 A2b); kadar je Ar2 A1a) ali A7c), je R8 enak, kot je definiran v zahtevku 4, kadar je Ar2 A1) ali A7); kadar je Ar2 A7c), je m enak tistemu, kot je definiran v zahtevku 8, kadar je Ar2 A7b); kadar je Ar2 A1a), je R6 atom vodika, atom fluora, atom klora, ciano skupina, Ci do C6 alkilna skupina, Ci do Ce alkoksi skupina, halo-Ci do Ce alkoksi skupina, Ci do Ce alkilsulfanilna skupina, Ci do C6 alkilsulfinilna skupina ali -CONR10R11, kjer, kadar je R6 -CONR10R11, je R10 atom vodika, Ci do Ce alkilna skupina ali Ci do C6 acilna skupina in R11 je atom vodika ali Ci do C6 alkilna skupina ali R10 in R11 lahko skupaj tvorita pirolidinilno skupino, piperidinilno skupino, piperazinilno skupino ali morfolinilno skupino; in kadar je Ar2 A1a), A2b) ali A7c), je R7 atom vodika, atom fluora ali atom klora; pod pogojem, da kadar je Ar2 A1a), kombinacije substituentov R6, R7 in R8 izključujejo kombinacijo atoma vodika in atoma halogena.
  10. 10. Spojina po zahtevku 9 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer v formuli (I) je Ar1 skupina, izbrana iz skupine, ki jo sestavljajo B1), B2), B6b), B9c) in B9d [Chemical Formula 8]
    kjer R1 je atom vodika, hidroksi skupina, Ci do C3 alkilna skupina, Ci do C3 alkoksi skupina ali hidroksi Ci do C4 alkilna skupina; kadar je Ar1 B1) ali B2), je R12 atom vodika, atom fluora, atom klora, ciano skupina, Ci do C3 alkilna skupino ali Ci do C6 alkoksi skupina; kadar je Ar1 B1) ali B6b), je R13 atom vodika, hidroksi skupina, atom fluora ali atom klora; kadar je Ar1 B9c) ali B9d), je R14 je atom vodika, atom fluora, atom klora, Ci do C3 alkilna skupina, metoksi skupina ali etoksi skupina; kadar je Ar1 B9c) ali B9d), je R15 atom vodika, atom fluora ali atom klora; in kadar je Ar1 B2), je eden od W10 in W11 N, drugi od njiju je CH.
  11. 11. Spojina po zahtevku 10 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer v formuli (I) j e Ar1 skupina, izbrana iz skupine, ki jo sestavljajo B1), B6b) in B9c1); [Chemical Formula 9]
    kjer, kadar je Ar1 B1), je R12 enak kot je definiran v zahtevku 10, kadar je Ar1 B1); kadar je Ar1 B1) ali B6b), je R13 enak tistemu, ki je definiran v zahtevku 10, kadar je Ar1 B1) ali B6b); in kadar je Ar1 B9c1), je R14 enak, kot je definiran v zahtevku 10, kadar je Ar1 B9c).
  12. 12. Spojina po zahtevku 11 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer v formuli (I) je Ar2 skupina, izbrana iz skupine, ki jo sestavljajo A1b), A2b) in A7c [Chemical Formula 10]
    kjer, kadar je Ar2 A2b), je R6a enak kot je definiran v zahtevku 8, kadar je Ar2 A2b); kadar je Ar2 A7c), je m enak tistemu, kot je definiran v zahtevku 8, kadar je Ar2 A7b); kadar je Ar2 A1b), je R6 dano skupina, etilna skupina ali Ci do C3 alkoksi skupina; R7 je atom fluora ali atom klora; in kadar je Ar2 A1b) ali A7c), je R8 atom vodika, atom fluora, atom klora ali C1 do C3 alkilna skupina.
  13. 13. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina, predstavljena s formulo (1), je (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-2-oksopirolidin-3-il] sečnina, (-)-1 -(4-klorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-2-oksopirolidin-3-il] sečnina, (-)-1-(3,4-difluorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-2-oksopirolidin-3-il] sečnina, (-)-1 -(4-cianofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-2-oksopirolidin-3-il] sečnina, (-)-1-(4-klorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-1-metil-2-oksopirolidin-3-Ν] sečnina, (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-1-metil-2-oksopirolidin-3-il] sečnina, (-)-1-[(3S*,4R*)-4-(3-fluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil) sečnina, (-)-1-[(3S*,4R*)-4-(2-fluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil) sečnina, 1-[(3S*,4R*)-4-(2-kloro-4-metoksifenil)-2-oksopirolidin-3-il]-3- (4-fluorofenil) sečnina, (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-4-(4-metoksi-2-metilfenil)-2-oksopirolidin-3-il] sečnina, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil) sečnina, (-)-1-[(3S*,4R*)-4-(2,5-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil) sečnina, (-)-1-[(3S*,4R*)-4-(3,5-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil) sečnina, (-)-1-[(3S*,4R*)-4-(6-fluoro-2,3-dihidrobenzofuran-5-il)-2-oksopirolidin-3-il] -3-(4-fluorofenil) sečnina, (-)-1-[(3S*,4R*)-4-(3-fIuoro-5-metoksipiridin-2-il)-2-oksopirolidin-3-il]-3-(4-fluorofenil) sečnina, (-)-1-(4-fluorofenil)-3-[(3S*,4R*)-4-(5-metoksi-tiofen-2-il)-2-oksopirolidin-3-Ν] sečnina, (-)-1 -(4-fluorofenil)-3-[(3S*,4R*)-4-(4-metiltiofenil)-2-oksopirolidin-3-il] sečnina, (-)-1-(4-klorofenil)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il] sečnina, (-)-1-(4-cianofenil)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-Π] sečnina, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-metoksifenil) sečnina, (-)-1-(5-klorotiiazol-2-il)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il] sečnina , (-)-1-(6-kloropiridin-3-il)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il] sečnina, (-)-1-(5-kloropiridin-2-il)-3-[(3S*,4R*)-4-(2,6-difluoiO-4-metoksifenil)-2-oksopirolidin-3-il] sečnina , (-)-1-(benzo[b]tiofen-2-il)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-Π] sečnina, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(5-metiltiofen-2-il) sečnina, (-)-1 -(4-fluorofenil)-3-[(3S*,4R*)-4-(4-metoksifenil)-5-rnetil-2-oksopirolidin-3-il] sečnina, (-)-1-(4-fluorofenil)-3-[(3S*,4R*,5R*)-4-(4-metoksifenil)-5-metil-2-oksopirolidin-3-il] sečnina, (+)-1- (4-klorofenil)-3-[(3S*,4R*)-2-okso-4-fenilpirolidin-3-il] sečnina, (+)-trans-1-(4-klorofenil)-3-[4-(4-metoksifenil)-1-metil-2-oksopirolidin-3-il] sečnina, (+)-trans-1-(4-fluorofenil)-3-[4-(4-metoksifenil)-2-oksopirolidin-3-il] sečnina, (+)-trans-1-(4-klorofenil)-3-[4-(4-metoksifenil)-1-metil-2-oksopirolidin-3-il] sečnina, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-[4-(trifluorometoksi) fenil] sečnina, (-)-1-[(3S*,4R*)-4-(2,6-clifluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-fenil sečnina, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fenoksifenil) sečnina, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(3-fluorofenil) sečnina, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(3,4-difluorofenil) sečnina, (-)-1-(5-klorotiopen-2-il)-3-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il] sečnina, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(p-tolil) sečnina, (-)-1-[(3S*,4R*)-1-etil-4-(4-metoksifenil)-2-oksopirolidin-3-il]-3-(4-fluorofenil) sečnina, (-)-1 -(4-fluorofenil)-3-[(3S*,4R*)-1 -(1 -hidroksi-2-metilpropan-2-il)-4-(4-metoksifenil) -2-oksopirolidin-3-il] sečnina, (+)-trans-1-(4-klorofenil)-3-[1-(2-hidroksietil)-4-(4-metoksifenil)-2-oksopirolidin-3-ίΙ] sečnina, (+)-trans-1-(4-klorofenil)-3-[1-(2-hidroksietil)-4-(4-metoksifenil)-2-oksopirolidin-3-ϋ] sečnina, (-)-trans-1-(4-klorofenil)-3-[1-(2-hidroksietil)-4-(4-metoksifenil)-2-oksopirolidin-3-il] sečnina, (-)-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} propionske kisline 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} propionske kisline (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-(2I6-difluoro-4-metoksifenil)-1-metil-2-oksopirolidin-3-il]-3-(4-fluorofenil) sečnina, (-)-1-[(3S*,4R*)-4-(2-fluoro-4-metoksifenil)-1-(2-hidroksietil)-2-oksopirolidin-3-il] -3-(4-fluorofenil) sečnina, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-1-(2-hidroksietil)-2-oksopirolidin-3-Π] -3-(4 -fluorofenil) sečnina, (+)-1-(4-fluorofenil)-3-[(3R*,4S*)-1-metoksi-4-(4-metoksifenil)-2-oksopirolidin-3-Ν] sečnina, (-)-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-Η] sečnina, (-)-1-[(3S*,4R*)-4-(2-fluoro-4-metoksifenil)-2-(metoksiimino) pirolidin-3-il] -3-(4-fluorofenil) sečnina, (-)-1-[(3S*,4R*,Z)-4-(2,6-difluoro-4-metoksifenil)-2-(metoksiimino) pirolidin-3-il] -3-(4-fluorofenil) sečnina, (-)-1-(4-fluorofenil)-3-{(3S*,4R*,Z)-2-[(2-hidroksietoksi)imino]-4-(4-metoksifenil) pirolidin-3-il} sečnina, (-)-1-{(3S*,4R*lZ)-4-(2l6-difluoro-4-metoksifenil)-2-[(2-hidroksietoksi) imino] pirolidin-3-il} (4-fluorofenil) sečnina, (-)-1 -[(3S*,4R*. Z)-4- (2,6-difluoro-4-metoksifenil)-2-(metilimino) pirolidin-3-Ν] -3- (4-fluorofenil) sečnina, (-)-1-(4-fluorofenil)-3-[(3S*,4R*,Z)-2-(2-hidroksiimino)-4-(4-metoksifenil) pirolidin-3-il] sečnina, (-)-1-[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-2-oksopirolidin-3-il]-3-(3-hidroksi-4-metilfenil) sečnina, (-)-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-ίΙ] sečnina, (-)-1-(4-cianofenil)-3-[(3S*,4R*)-4-(6-fluoro-2,3-dihidrobenzofuran-5-il)-2-oksopirolidin-3-il] sečnina , (-)-1-{(3S*,4R*,Z)-4-(2,6-difluoro-4-metoksifenil)-2-[(2-hidroksietoksi) imino] pirolidin-3-il} (p-tolil) sečnina, ali (-)-1 -[(3S*,4R*)-4-(2,6-difluoro-4-metoksifenil)-1 -(2-hidroksietil)-2-oksopirolidin-3-il] -3-fenil sečnina.
  14. 14. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina
  15. 15. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina
  16. 16. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina:
  17. 17. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina:
  18. 18. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina:
  19. 19. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina:
  20. 20. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina:
  21. 21. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina:
  22. 22. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina:
  23. 23. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina:
  24. 24. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina:
  25. 25. Spojina po zahtevku 1 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat, kjer je spojina:
  26. 26. Farmacevtski sestavek, ki obsega kot aktivno sestavino spojine po katerem koli od zahtevkov 1 do 25 ali njena farmakološko sprejemljiva sol ali njen solvat ali hidrat.
  27. 27. Farmacevtski sestavek, ki vsebuje spojino po katerem koli od zahtevkov 1 do 25 ali njeno farmakološko sprejemljivo sol, solvat ali hidrat, in farmacevtsko sprejemljiv nosilec, za uporabo pri preprečevanju ali zdravljenju vnetnih bolezni, kroničnih bolezni dihalnih poti, raka, septikemije, alergijskih simptomov, okužbe z virusom HIV, motnje v cirkulaciji, nevroinflamacije, živčnih motenj, bolečine, prionske bolezni, amiloidoze in imunskih motnenj.
SI201430579T 2013-11-28 2014-11-27 Derivati sečnine ali njenih farmakološko sprejemljivih soli uporabnih kot formil peptidni receptor podobnih 1 (fprl-1) agonistov SI3075726T1 (sl)

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