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ME02809B - Ariltriazoloni spojeni sa bis-arilom i njihova upotreba - Google Patents

Ariltriazoloni spojeni sa bis-arilom i njihova upotreba

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Publication number
ME02809B
ME02809B MEP-2017-165A MEP16517A ME02809B ME 02809 B ME02809 B ME 02809B ME P16517 A MEP16517 A ME P16517A ME 02809 B ME02809 B ME 02809B
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ME
Montenegro
Prior art keywords
denotes
group
formula
trifluoromethyl
substituted
Prior art date
Application number
MEP-2017-165A
Other languages
German (de)
English (en)
French (fr)
Inventor
Chantal Fürstner
Jörg Keldenich
Martina Delbeck
Peter Kolkhof
Axel Kretschmer
Ingo Pluschkell
Elisabeth Pook
Carsten Schmeck
Hubert Trübel
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Bayer Ip Gmbh
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Publication of ME02809B publication Critical patent/ME02809B/me

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Claims (9)

1. Jedinjenje formule (I)naznačeno time štoR1 označava (C1-C6)-alkil, koji može biti supstituisan jednostruko do trostruko, isto ili različito, sa ostacima izabranim iz niza fluor, trifluormetil, okso, hidroksi, metoksi, etoksi, (C3-C6)-cikloalkil i fenil,pri čemu (C3-C6)-cikloalkil može biti supstituisan maksimalno dvostruko, isto ili različito, sa ostacima izabranim iz niza fluor, metil, trifluormetil, etil i hidroksiipri čemu fenil može biti supstituisan do dva puta, isto ili različito, sa ostacima izabranim iz niza fluor, hlor, cijano, metil, difluormetil, trifluormetil, etil, hidroski, metoksi, trifluormetoksi, etoksi, hidroksikarbonil, metoksikarbonil, etoksikarbonil i aminokarbonil,ili označava (C2-C6)-alkenil,ilioznačava (C3-C6)-cikloalkil, koji može biti supstituisan jednostruko ili dvostruko, isto ili različito, sa ostacima izabranim iz niza fluor, metil, trifluormetil, etil i hidroksi,Ar1 označava fenil ili tienil, koji mogu biti supstituisani jednostruko ili dvostruko, isto ili različito, sa ostacima izabranim iz niza fluor, hlor, cijano, metil, trifluormetil, etil, hidroksi, metoksi, trifluormetoksi i etoksi,L1 označava grupu -CH2- ili -SO2-,Q označava 5-člani prsten heteroarila sa do tri prstenasta heteroatoma iz niza N, O i/ili S ili jednim 6-članim prstenom heteroarila sa do dva atoma prstena azota ilieventualno supstituisani fenilni prsten sa formulomili, gde* označava mesto spoja sa grupom L1a ** označava mesto spoja sa grupom L2,a R2A znači vodonik, fluor, hlor, brom, metil, trifluormetil, hodroksimetil, karbamoiloksimetil, hidroksicarbonil, metoksikarbonil, etoksikarbonil, aminokarbonil, metilaminokarbonil ili tert.-butilaminokarbonil,R2 označava supstituent izabran iz niza fluor, hlor, brom, (C1-C4)-alkil, (C3-C6)-cikloalkil, fenil, (C1-C4)-alkoksi, hidroksikarbonil, (C1-C4)-alkoksikarbonil, aminokarbonil i mono-(C1-C4)-alkilaminokarbonil,pri čemu supstituent (C1-C4)-alkila može biti supstituisan sa hidroksi, (C1-C4)-alkoksi, karbamoiloksi, hiodroksikarbonilom, (C1-C4)-alkokskarbonilom ili aminokarbonilom ili do tri puta fluoromipri čemu supstituent fenila može biti supstituisan fluorom, hlorom, metilom ili trifluormetilom,n označava broj 0 ili 1,L2 označava vezu ili grupu sa formulom -(CR3AR3B)p-, gdeR3A označava vodonik ili metil, R3B vodonik, (C1-C4)-alkil, hidroskikarbonil, (C1-C4)-alkoksikarbonil ili aminokarbonil,pri čemu (C1-C4)-alkil može biti supstituisan sa hidroksi ili karbamoiloksi,ip označava broj 1 ili 2,pri čemu u slučaju da se grupa -CR3AR3B- pojavljuje dva puta, pojedinačna značenja R3A i R3B mogu biti ista ili različita,iAr2 označava fenil, koji može biti supstituisan jednostruko ili dvostruko, isto ili različito, sa ostacima izabranim iz niza fluor, hlor, cijano, difluormetil, trifluormetil, (C1-C4)-alkil, metoksi, difluormetoksi, trifluormetoksi i etoksi,kao i njegove soli, solvate i solvate soli.
2. Jedinjenje formule (I) prema zahtevu 1, naznačeno time što R1 označava (C1-C4)-alkil, koji može biti supstituisan jednostruko ili dvostruko, isto ili različito, sa ostacima izabranim iz niza fluor, trifluormetil, okso, hidroksi i fenil, pri čemu fenil može biti supstituisan ostatkom izabranim iz niza fluor, hlor, metil, trifluormetil, metoksi, hidroksikarbonil i metoksikarbonil, ili označava alil ili ciklopropil, Ar1 označava fenil ili tijenil, koji su supstituisani sa po jednim ostatkom iz niza fluor i hlor, L1 označava grupu -CH2-, Q označava piridil, pirimidinil ili eventualno supstituisani fenilni prsten sa formulom ili ili označava eventualno supstituisani 5-člani heteroarilni prsten sa formulom ili , gde * označava mesto spoja sa grupom L1 i ** označava mesto spoja sa grupom L2, R2A znači vodonik, fluor, hlor, brom, metil, trifluormetil, hodroksimetil, karbamoiloksimetil, hidroksicarbonil, metoksikarbonil, etoksikarbonil, aminokarbonil, metilaminokarbonil ili tert.-butilaminokarbonil, R2B označava vodonik, metil ili trifluormetil i R2C označava vodonik ili metil, koji može biti supstituisan hidroksikarbonilom, metoksikarbonilom ili aminokarbonilom, L2 označava vezu ili grupu -CH2-, i Ar2 označava fenil, koji može biti supstituisan jednostruko ili dvostruko, isto ili različito, sa ostacima izabranim iz niza fluor, hlor, metil, trifluormetil, metoksi i trifluormetoksi, kao i njegove soli, solvate i solvate soli.
3. Jedinjenje formule (I) prema zahtevu 1 ili 2, naznačeno time što R1 označava (C1-C4)-alkil, koji može biti supstituisan jednostruko ili dvostruko, isto ili različito, sa ostacima izabranim iz niza fluor, trifluormetil i hidroksi ili označava ciklopropil, Ar1 označava p-hlorfenil, L1 označava grupu -CH2-, Q označava pirimidinilni prsten sa formulom ili ili označava eventualno supstituisani 5-člani heteroarilni prsten sa formulom ili , gde * označava mesto spoja sa grupom L1 i ** označava mesto spoja sa grupom L2, R2B označava vodonik, metil ili trifluormetil i R2C označava vodonik ili metil, koji može biti supstituisan hidroksikarbonilom, metoksikarbonilom ili aminokarbonilom, L2 označava vezu ili grupu -CH2-, i Ar2 označava fenil, koji može biti supstituisan jednostruko ili dvostruko, isto ili različito, sa ostacima izabranim iz niza fluor, hlor, metil, trifluormetil, metoksi i trifluormetoksi, kao i njegove soli, solvate i solvate soli.
4. Postupak za proizvodnju jedinjenja formule (I), kao što je definisano u zahtevima 1 do 3, naznačen time što se derivat 5-aril-1,2,4-triazolona formule (II) u kojoj Ar1 i R1 imaju značenja navedena u zahtevima 1 do 3, u prisustvu baze ili [A] sa jedinjenjem formule (III) u kojoj Ar2, L1, L2, Q, R2 i n imaju značenja navedena u zahtevima 1 do 3, i X1 označava odlazeću grupu poput na primer hlora, broma, joda, mezilata, ili tozilata, pretvara u jedinjenje formule (I) ili [B] alternativno u slučaju da L2 u formuli (I) označava vezu i da je grupa Ar2 vezana za atom ugljenika prstena Q, sa jedinjenjem formule (IV) u kojoj L1, Q, R2 i n imaju značenja navedena u zahtevima 1 do 3, X1 predstavlja odlazeću grupu poput na primer hlora, broma, joda, mezilata ili tozilata, i X2 predstavlja za atom ugljenika prstena Q vezanu odlazeću grupu poput na primer hlora, broma, joda, mezilata ili triflata, pretvara u intermedijar formule (XV) u kojoj Ar1, L1, Q, R1, R2, X2 i n imaju gore navedena unačenja i gde se intermedijar zatim u prisustvu pogodnog katalizatora prelaznog metala povezuje sa jedinjenjem formule (VI)         Ar2-M     (VI), u kojoj Ar2 ima značenje navedeno u zahtevima 1 do 3 i M označava grupu formule -B(OR4)2, -MgHal, -ZnHal ili -Sn(R5)3, gde Hal označava halogen, posebno hlor, brom ili jod, R4 označava vodonik ili (C1-C4)-alkil ili gde su oba ostatka R4 povezana međusobno i zajedno čine -(CH2)2-, -(CH2)3-, -C(CH3)2-C(CH3)2- ili -CH2-C(CH3)2-CH2-most i R5 označava (C1-C4)-alkil, spaja u jedinjenje formule (I-A) u kojem Ar1, Ar2, L1, Q, R1, R2 i n imaju gore navedena značenja ili [C] alternativno za slučaj da L2 u formuli (I) označava grupu -(CR3AR3B)p-, kao što je definisano u zahtevima 1 do 3, i vezano je za atom azota prstena Q, sa jedinjenjem formule (VII) u kojoj L1, R2 i n imaju značenja navedena u zahtevima 1 do 3, Q' označava 5-člani heteroarilni prsten, kao što je definisan u zahtevima 1 do 3 pod Q, koji sadrži trivalentni atom prstena azota koji je povezan sa prikazanim atomom vodonika, i X1 označava odlazeću grupu poput na primer hlora, broma, joda, mezilata, ili tozilata, pretvara u intermedijar formule (VIII) u kojoj Ar1, L1, Q', R1, R2 i n imaju gore navedena značenja i njega zatim se u prisustvu baze sa jedinjenjem formule (IX) u kojoj Ar2 ima značenje navedeno u zahtevima 1 do 3, L2A označava grupu -(CR3AR3B)p-, kao što je definisano u zahtevima 1 do 3 i X3 označava odlazeću grupu poput na primer hlora, broma, joda, mezilata, ili tozilata, N-alkilira u jedinjenje formule (I-B) u kojoj Ar1, Ar2, L1, L2A, Q', R1, R2 i n imaju gore navedena značenja, i tako dobijena jedinjenja formule (I), (I-A) odn. (I-B) se eventualno razdvaja na njihove enantiomere i/ili diastereomere i/ili uz pomoć odgovarajućih (i) rastvarača i/ili (ii) baza ili kiselina pretvara u njihove solvate, soli i/ili solvate soli.
5. Jedinjenje formule (I), kao što je definisano u jednom od zahteva 1 do 3, naznačeno time što je za upotrebu u lečenju i/ili prevenciji bolesti.
6. Jedinjenje formule (I), kao što je definisano u jednom od zahteva 1 do 3, naznačeno time što je za primenu u postupku za lečenje i/ili prevenciju akutne i hronične insufucijencije srca, hipervolemijske i euvolemijske hipomatremije, ciroze jetre, ascitesa, edema i sindroma neadekvatne ADH-sekrecije (SIADH).
7. Lek naznačen time što sadrži jedinjenje formule (I), kao što je definisano u jednom od zahteva 1 do 3, u kombinaciji sa jednim ili više inertnih, netoksičnih, farmaceutski prikladnih pomoćnih sredstava.
8. Lek naznačen time što sadrži jedinjenje formule (I), kao što je definisano u jednom od zahteva 1 do 3, u kombinaciji sa jednom ili više dodatnih aktivnih supstanci izabranih iz grupe koja se sastoji od diuretika, angiotensinsinskih AII-antagonista, ACE-blokatora, beta-receptorskih blokatora, antagonista mineralokortikoidnih receptora, organskih nitrata, NO-donatora i pozitivno-inotropno aktivnih supstanci.
9. Lek prema jednom od zahteva 7 do 8, naznačeno time što je za primenu u postupku za lečenje i/ili prevenciju akutne i hronične insufucijencije srca, hipervolemijske i euvolemijske hipomatremije, ciroze jetre, ascitesa, edema i sindroma neadekvatne ADH-sekrecije (SIADH).
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JP6623220B2 (ja) 2014-11-03 2019-12-18 バイエル ファーマ アクチエンゲゼルシャフト ヒドロキシアルキル置換フェニルトリアゾール誘導体およびその使用

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