DK2539326T3 - Bis-arylforbundne aryltriazoloner og anvendelse heraf - Google Patents

Bis-arylforbundne aryltriazoloner og anvendelse heraf Download PDF

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DK2539326T3
DK2539326T3 DK11704637.5T DK11704637T DK2539326T3 DK 2539326 T3 DK2539326 T3 DK 2539326T3 DK 11704637 T DK11704637 T DK 11704637T DK 2539326 T3 DK2539326 T3 DK 2539326T3
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mmol
compound
methyl
formula
triazol
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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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Claims (9)

1. Forbindelse med formel (I) hvor
R1 står for (C1-C6)-alkyl, som kan være substitueret en til tre gange, ens eller forskelligt, med grupper udvalgt af rækken fluor, trifluormethyl, oxo, hydroxy, methoxy, ethoxy, (C3-C6) -cycloalkyl og phenyl, idet (C3-C6)-cycloalkyl kan være substitueret op til to gange, ens eller forskelligt, med grupper udvalgt af rækken fluor, methyl, trifluormethyl, ethyl og hydroxy, og idet phenyl kan være substitueret op til to gange, ens eller forskelligt, med grupper udvalgt af rækken fluor, chlor, cyano, methyl, difluormethyl, trifluormethyl, ethyl, hydroxy, methoxy, trifluormethoxy, ethoxy, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl og aminocarbonyl, eller står for (Cd-Ce) -alkenyl eller står for (C3-C6)-cycloalkyl, som kan være substitueret en eller to gange, ens eller forskelligt, med grupper udvalgt af rækken fluor, methyl, trifluormethyl, ethyl og hydroxy, Ar1 står for phenyl eller thienyl, som hver især kan være substitueret en eller to gange, ens eller forskelligt, med grupper udvalgt af rækken fluor, chlor, cyano, methyl, trifluormethyl, ethyl, hydroxy, methoxy, trifluormethoxy og ethoxy, L1 står for gruppen -CH2- eller -SO2-, Q står for en 5-leddet heteroaryl-ring med op til tre ring-heteroatomer fra rækken N, 0 og/eller S eller en 6-leddet heteroaryl-ring med op til to ring-nitrogenatomer eller står for en i givet fald substitueret phenyl-ring med formel
hvor * markerer forbindelsesstedet med gruppen L1 og ** markerer forbindelsesstedet med gruppen L2, og R2A betegner hydrogen, fluor, chlor, brom, methyl, trifluormethyl, hydroxymethyl, carbamoyloxymethyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, methylaminocarbonyl eller tert- butylaminocarbonyl, R2 står for en substituent udvalgt af rækken fluor, chlor, brom, (C1-C4)-alkyl, (C3-C6) -cycloalkyl, phenyl, (C1-C4) -alkoxy, hydroxycarbonyl, (C1-C4)-alkoxycarbonyl, aminocarbonyl og mono-(C1-C4) -alkylaminocarbonyl, idet (C1-C4)-alkyl-substituenten på sin side kan være substitueret med hydroxy, (C1-C4)-alkoxy, carbamoyloxy, hydroxycarbonyl, (C1-C4)-alkoxycarbonyl eller aminocarbonyl eller op til tre gange med fluor, og idet phenyl-substituenten på sin side kan være substitueret med fluor, chlor, methyl eller trifluormethyl, n står for tallet 0 eller 1, L2 står for en binding eller for en gruppe med formel -(CR3aR3b) P-, hvor R3A betegner hydrogen eller methyl, R3B betegner hydrogen, (C1-C4) -alkyl, hydroxycarbonyl, (C1-C4)-alkoxycarbonyl eller aminocarbonyl, idet (C1-C4)-alkyl kan være substitueret med hydroxy eller carbamoyloxy, og p betegner tallet 1 eller 2, idet de enkelte betegnelser af R3A og R3B, i det tilfælde at gruppen -CR3AR3B- optræder to gange, hver gang kan være ens eller forskellige, og Ar2 står for phenyl, som kan være substitueret en eller to gange, ens eller forskelligt, med grupper udvalgt af rækken fluor, chlor, cyano, difluormethyl, trifluormethyl, (C1-C4)- alkyl, methoxy, difluormethoxy, trifluormethoxy og ethoxy, samt deres salte, solvater og solvater af saltene.
2. Forbindelse med formel (I) ifølge krav 1, hvor R1 står for (C1-C4) -alkyl, som kan være substitueret en eller to gange, ens eller forskelligt, med grupper udvalgt af rækken fluor, trifluormethyl, oxo, hydroxy og phenyl, idet phenyl på sin side kan være substitueret med en gruppe udvalgt af rækken fluor, chlor, methyl, trifluormethyl, methoxy, hydroxycarbonyl og methoxycarbonyl eller står for allyl eller cyclopropyl, Ar1 står for phenyl eller thienyl, som hver især er substitueret med en gruppe udvalgt af rækken fluor og chlor, L1 står for gruppen -CH2-, Q står for en pyridyl-, pyrimidinyl- eller i givet fald substitueret phenyl-ring med formel
for en i givet fald substitueret 5-leddet heteroaryl-ring med formel
* markerer forbindelsesstedet med gruppen L1, og ** markerer forbindelsesstedet med gruppen L2, R2A betegner hydrogen, fluor, chlor, brom, methyl, trifluormethyl, hydroxymethyl, carbamoyloxymethyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, methylaminocarbonyl eller tert- butylaminocarbonyl, R2B betegner hydrogen, methyl eller trifluormethyl, og R2C betegner hydrogen eller methyl, som kan være substitueret med hydroxycarbonyl, methoxycarbonyl eller aminocarbonyl, L2 står for en binding eller gruppen -CH2-, og Ar2 står for phenyl, som er substitueret en eller to gange, ens eller forskelligt, med grupper udvalgt af rækken fluor, chlor, methyl, trifluormethyl, methoxy og trifluormethoxy, samt deres salte, solvater og solvater af saltene.
3. Forbindelse med formel (I) ifølge krav 1 eller 2, hvor R1 står for (C1-C4) -alkyl, som kan være substitueret en eller to gange, ens eller forskelligt, med grupper udvalgt af rækken fluor, trifluormethyl og hydroxy eller står for cyclopropyl, Ar1 står for p-chlorphenyl, L1 står for gruppen -CH2-, Q står for en pyrimidinyl-ring med formel
for en i givet fald substitueret 5-leddet heteroaryl-ring med formel
* markerer forbindelsesstedet med gruppen L1, og ** markerer forbindelsesstedet med gruppen L2, R2B betegner hydrogen, methyl eller trifluormethyl, og R2C betegner hydrogen eller methyl, som kan være substitueret med hydroxycarbonyl, methoxycarbonyl eller aminocarbonyl, L2 står for en binding eller for gruppen -CH2-, og Ar2 står for phenyl, som er substitueret en eller to gange, ens eller forskelligt, med grupper udvalgt af rækken fluor, chlor, methyl, trifluormethyl, methoxy og trifluormethoxy, samt deres salte, solvater og solvater af saltene.
4. Fremgangsmåde til fremstilling af forbindelser med formel (I) som defineret i kravene 1 til 3, kendetegnet ved, at man omsætter et 5-aryl-l,2,4-triazolon-derivat med formel (II)
hvor Ar1 og R1 har de i kravene 1 til 3 anførte betegnelser, i nærvær af en base enten [A] med en forbindelse med formel (III)
hvor Ar2, L1, L2, Q, R2 og n har de i kravene 1 til 3 anførte betegnelser, og X1 står for en fraspaltelig gruppe såsom chlor, brom, iod, mesylat eller tosylat, til en forbindelse med formel (I), eller [B] som et alternativ i det tilfælde, at L2 i formel (I) står for en binding, og gruppen Ar2 er bundet til et carbonatom i ringen Q, med en forbindelse med formel (IV)
hvor L1, Q, R2 og n har de i kravene 1 til 3 anførte betegnelser, X1 står for en fraspaltelig gruppe såsom chlor, brom, iod, mesylat eller tosylat, og X2 står for en til carbonatomet i ringen Q bundet fraspaltelig gruppe såsom chlor, brom, lod, mesylat eller triflat, til et intermediat med formel (V)
hvor Ar1, L1, Q, R1, R2, X2 og n har de ovenfor anførte betegnelser, og i nærvær af en egnet overgangsmetalkatalysator derefter kobler denne sammen med en forbindelse med formel (VI) Ar2-M (VI), hvor Ar2 har den i kravene 1 til 3 anførte betegnelse, og M står for en gruppe med formel -B(OR4)2, -MgHal, -ZnHal eller -Sn (R5) 3, hvor Hal betegner halogen, navnlig chlor, brom eller iod, R4 betegner hydrogen eller (C1-C4)-alkyl, eller begge grupper R4 er forbundet med hinanden og tilsammen danner en -(CH2)2-, (CH2)3-, -C (CH3) 2-C (CH3) 2- eller -CH2-C (CH3) 2-CH2-bro, og R5 betegner (C1-C4) -alkyl, til en forbindelse med formel (I-A)
hvor Ar1, Ar2, L1, Q, R1, R2 og n har de ovenfor anførte betegnelser, eller [C] som et alternativ i det tilfælde, at L2 i formel (I) står for gruppen -(CR3AR3B)P- som defineret i kravene 1 til 3 og er bundet til et nitrogenatom i ringen Q, omsætter med en forbindelse med formel (VII)
hvor L1, R2 og n har de i kravene 1 til 3 anførte betegnelser, Q' står for en 5-leddet heteroaryl-ring som defineret i kravene 1 til 3 under Q, som indeholder et med det viste hydrogenatom forbundet, trivalent ring-nitrogenatom, og X1 står for en fraspaltelig gruppe såsom chlor, brom, iod, mesylat eller tosylat, til et intermediat med formel (VIII) ' ΊΙ
· · · hvor Ar1, L1, Q', R1, R2 og n har de ovenfor anførte betegnelser, og i nærvær af en base derefter N-alkylerer denne med en forbindelse med formel (IX)
hvor Ar2 har den i kravene 1 til 3 anførte betegnelse, L2A står for gruppen -(CR3AR3B)P- som defineret i kravene 1 til 3, og X3 står for en fraspaltelig gruppe såsom chlor, brom, rod, mesylat eller tosylat, til en forbindelse med formel (I-B)
hvor Ar1, Ar2, L1, L2A, Q', R1, R2 og n har de ovenfor anførte betegnelser, og udskiller de således opnåede forbindelser med formel (I), (I-A) eller (I-B) i givet fald i deres enantiomerer og/eller diastereomerer og/eller omdanner dem med de tilsvarende (i) opløsningsmidler og/eller (ii) baser eller syrer til deres solvater, salte og/eller solvater af saltene.
5. Forbindelse med formel (I) som defineret i et af kravene 1 til 3 til anvendelse i behandling og/eller prævention af sygdomme.
6. Forbindelse med formel (I) som defineret i et af kravene 1 til 3 til anvendelse i en fremgangsmåde til behandling og/eller prævention af akut og kronisk hjerteinsufficiens, hypervolæmisk og euvolæmisk hyponatriæmi, levercirrose, ascites, ødemer og syndrom for ukorrekt ADH-sekretion (SIADH).
7. Lægemiddel indeholdende en forbindelse med formel (I) som defineret i et af kravene 1 til 3 i kombination med et eller flere inerte, ikke-toksiske, farmaceutisk egnede hjælpestoffer.
8. Lægemiddel indeholdende en forbindelse med formel (I) som defineret i et af kravene 1 til 3 i kombination med et eller flere yderligere aktivstoffer udvalgt af gruppen bestående af diuretika, angiotensin ΑΙΙ-antagonister, ACE-hæmmere, betarecept or-blokkere, mineralocorticoid-receptor-antagonister, organiske nitrater, NO-donatorer og positive inotrop aktive substanser.
9. Lægemiddel ifølge krav 7 eller 8 til anvendelse i behandling og/eller prævention af akut og kronisk hjerteinsufficiens, hypervolæmisk og euvolæmisk hyponatriæmi, levercirrose, ascites, ødemer og af syndromet for ukorrekt ADH-sekretion (SIADH).
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