DK2748149T5 - Pyridazinonforbindelser og deres anvendelse som DAAO-inhibitorer - Google Patents

Pyridazinonforbindelser og deres anvendelse som DAAO-inhibitorer Download PDF

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DK2748149T5
DK2748149T5 DK12753164.8T DK12753164T DK2748149T5 DK 2748149 T5 DK2748149 T5 DK 2748149T5 DK 12753164 T DK12753164 T DK 12753164T DK 2748149 T5 DK2748149 T5 DK 2748149T5
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formula
compound
ethyl
hydroxy
bis
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DK2748149T3 (da
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William Farnaby
Charlotte Fieldhouse
Katherine Hazel
David Livermore
Kevin Merchant
David Miller
Catrina Kerr
Natasha Kinsella
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Takeda Pharmaceuticals Co
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Priority claimed from GBGB1203533.3A external-priority patent/GB201203533D0/en
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Claims (16)

1. Forbindelse ifølge formel (I)
hvor R1 betegner et hydrogen- eller fluoratom eller en trifluormethylgruppe; R2 betegner en gruppe -X-Y-R3; X og Y hver uafhængigt af hinanden betegner en binding, et oxygenatom eller en gruppe -C(O), -S(0)n, -C(0)NR4, -S(0)2NR4, -NR4,
eller -CR4R5-, forudsat at X og Y ikke begge samtidigt kan betegne en binding, og forudsat at hvis X og Y begge er andet end en binding, så vil mindst én af X og Y betegne -CR4R5-; n er 0, 1 eller 2; hver R4 uafhængigt af hinanden betegner et hydrogenatom eller en Ci-C6-alkyl-eller Ci-C6-haloalkylgruppe; hver R5 uafhængigt af hinanden betegner et hydrogenatom, en Ci-C6-alkyl- eller Ci-C6-haloalkylgruppe eller =CH-; R3 betegner et 3- til 10-leddet mættet eller umættet carbocyklisk eller heterocyklisk ringsystem, hvor selve ringsystemet eventuelt substitueres af mindst én substituent valgt blandt halogen, hydroxyl, cyan, oxo, Ci-C6-alkyl, C2-C6-alkenyl, Ci-C6-haloalkyl, Ci-C6-hydroxyalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Q-Ce-alkylsulphinyl, Ci-C6-alkylsulphonyl, Ci-C6-alkylcarbonyl, CrC6-alkylcarbonyloxy, Ci-C6-alkoxycarbonyl, amino(-NH2), -CON(R6)2, CrCø-alkylamino, di-(Ci-C6-alkyl)amino, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkylmethyl, -[0]p-(CH2)q-0-R7 og en 4- til 6-leddet mættet eller umættet heterocyklisk ring (eventuelt substitueret af mindst én substituent valgt blandt Ci-C4-alkyl og CrQ-alkoxy); hver R6 uafhængigt af hinanden betegner et hydrogenatom eller en C1-C6- alkylgruppe; p er 0 eller 1; q er 1, 2, 3 eller 4; og R7 betegner en C!-C6-alkylgruppe; eller et farmaceutisk acceptabelt salt deraf.
2. Forbindelse ifølge krav 1, hvor R1 betegner et hydrogenatom.
3. Forbindelse ifølge krav 1 eller krav 2, hvor X betegner en binding, et oxygenatom eller en gruppe -C(O), -S(0)n, -C(0)NR4, -S(0)2NR4, -NR4,
eller -CR4R5-, og Y betegner en binding eller -CR4R5-.
4. Forbindelse ifølge krav 3, hvor X betegner en gruppe -S(0)n , - NR4, -CHR4 eller
og Y betegner en binding eller en gruppe -CHR4.
5. Forbindelse ifølge krav 4, hvor hver R4 uafhængigt af hinanden betegner et hydrogenatom eller en methylgruppe.
6. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, hvor, i R3, det 3- til 10-leddede mættede eller umættede carbocykliske eller heterocykliske ringsystem vælges blandt phenyl, pyridinyl, oxazolyl, pyrazinyl, cyclopropyl, cyclopentyl, cyclohexyl, tetrahydropyranyl, 2,3-dihydrobenzofuranyl, pyrimidinyl, imidazo[l,2-a]pyridinyl, pyrazolyl, thiazolyl og piperidinyl.
7. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, hvor R3 betegner et eventuelt substitueret 3- til 6-leddet mættet eller umættet carbocyklisk eller heterocyklisk ringsystem.
8. Forbindelse ifølge krav 7, hvor R3 betegner et 5- eller 6-leddet umættet carbocyklisk eller heterocyklisk ringsystem, hvor det heterocykliske ringsystem omfatter en eller to ringheteroatomer, som uafhængigt af hinanden er valgt blandt nitrogen og oxygen, hvor det carbocykliske eller heterocykliske ringsystem eventuelt er substitueret af en, to, tre eller fire substituenter, som uafhængigt af hinanden er valgt blandt fluor, chlor, brom, hydroxyl, cyan, oxo, Ci-C4-alkyl, C2-C4-alkenyl, Ci-C2-haloalkyl, Ci-C2-hydroxyalkyl, Ci-C4-alkoxy, Ci-C2-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulphinyl, Ci-C4-alkylsulphonyl, Ci-C4-alkylcarbonyl, Ci-C4-alkylcarbonyloxy, Ci-C4-alkoxycarbonyl, amino, carboxamido, Ci-C4-alkylamino, di-(Ci-C4-alkyl)amino, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkylmethyl, -[0]p-(CH2V0-R7 og en 4- til 6-leddet mættet eller umættet heterocyklisk ring, som eventuelt er substitueret af methyl eller methoxy.
9. Forbindelse ifølge krav 7 eller krav 8, hvor de eventuelle substituenter er valgt blandt cyan, fluor, chlor, difluormethyl, difluormethoxy, trifluormethyl, trifluormethoxy, methyl og methoxy.
10. Forbindelse ifølge formel (I) som defineret i krav 1 valgt fra gruppen bestående af:
4-Hydroxy-6-(2-phenylethyl)pyridazin-3(2H)-on, 6-[2-(4-Fluorphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on,
4-Hydroxy-6-{2-[5-(trifluormethyl)pyridin-2-yl]ethyl}pyridazin-3(2H)-on, 6-[(4-Chlorbenzyl)sulfanyl]-4-hydroxypyridazin-3(2H)-on,
4-Hydroxy-6-{2-[6-(trifluormethyl)pyridin-3-yl]ethyl}pyridazin-3(2H)-on, 6-[2-(3-Fluorphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on, 6-[2-(2-Fluorphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on, 6-[2-(3,5-Difluorphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on, 6-[2-(3,4-Difluorphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on,
4-Hydroxy-6-{2-[3-(trifluormethoxy)phenyl]ethyl}pyridazin-3(2H)-on,
4-Hydroxy-6-{2-[3-(trifluormethyl)phenyl]ethyl}pyridazin-3(2H)-on,
4-Hydroxy-6-{2-[5-(trifluormethyl)pyridin-3-yl]ethyl}pyridazin-3(2H)-on, 6-(2-Cyclohexylethyl)-4-hydroxypyridazin-3(2H)-on, 6-(2-Cyclopropylethyl)-4-hydroxypyridazin-3(2H)-on, 6-(2-Cyclopentylethyl)-4-hydroxypyridazin-3(2H)-on,
4-Hydroxy-6-[2-(4-methoxycyclohexyl)ethyl]pyridazin-3(2H)-on, 6-[2-(2,4-Difluorphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on, 6-{2-[3-(Difluormethyl)phenyl]ethyl}-4-hydroxypyridazin-3(2H)-on,
6-Benzyl-4-hydroxypyridazin-3(2H)-on, 6-[2-(3-Chlorphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on,
4-Hydroxy-6-(l-phenylcyclopropyl)pyridazin-3(2H)-on, 4-[2-(5-Hydroxy-6-oxo-l,6-dihydropyridazin-3-yl)ethyl]benzonitril, 6-[2-(3-Fluor-4-methylphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on, 6-[2-(4-Fluor-3-methylphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on, 6-[2-(3f4-Dimethoxyphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on,
4-Flydroxy-6-{2-[3-(trifluormethoxy)phenyl]ethyl}pyridazin-3(2FI)-on, 6-[2-(4-Chlorphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on, 6-[2-(2-Chlorphenyl)ethyl]-4-hydroxypyridazin-3(2H)-on,
4-Flydroxy-6-{2-[2-(trifluormethyl)phenyl]ethyl}pyridazin-3(2H)-on, 6-(4-(Difluormethoxy)phenethyl)-4-hydroxypyridazin-3(2H)-on, 6-(4-(Trifluormethoxy)phenethyl)-4-hydroxypyridazin-3(2H)-on( 6-(3-(Difluormethoxy)phenethyl)-4-hydroxypyridazin-3(2H)-on, 6-[l-(4-Fluorphenyl)cyclopropyl]-4-hydroxypyridazin-3(2H)-on, 6-[l-(4-Fluorphenyl)ethyl]-4-hydroxypyridazin-3(2FI)-on,
4-Hydroxy-6-{l-[3-(trifluormethyl)phenyl]ethyl}pyridazin-3(2FI)-on,
4-Hydroxy-6-{2-[4-(trifluormethyl)phenyl]ethyl}pyridazin-3(2H)-on, 6-((Cyclopropylmethyl)(methyl)amino)-4-hydroxypyridazin-3(2H)-on, 6-((Cyclohexylmethyl)(methyl)amino)-4-hydroxypyridazin-3(2H)-on, 6-(3-Chlorbenzyl)-4-hydroxypyridazin-3(2H)-on, 6-(4-Chlorbenzyl)-4-hydroxypyndazin-3(2H)-on, 6-(Cyclohexylmethyl)-4-hydroxypyridazin-3(2H)-on, 6-(4-Fluorbenzyl)-4-hydroxypyridazin-3(2H)-on, 6-(2-Chlor-6-fluorbenzyl)-4-hydroxypyridazin-3(2H)-on, 6-(2-Chlorbenzyl)-4-hydroxypyridazin-3(2H)-on, 6-(3-Fluorbenzyl)-4-hydroxypyridazin-3(2H)-on, 6-(2-Fluorbenzyl)-4-hydroxypyridazin-3(2H)-on, 6-(4-Methylbenzyl)-4-hydroxypyridazin-3(2H)-on, 6-(3-Methylbenzyl)-4-hydroxypyridazin-3(2H)-on,
4-Hydroxy-6-(3-(trifluormethyl)benzyl)pyndazin-3(2H)-on,
4-Hydroxy-6-{2-[5-(trifluormethyl)pyndin-3-yl]ethyl}pyndazin-3(2H)-on,
4-Hydroxy-6-[2-(oxan-4-yl)ethyl]pyridazin-3(2H)-on, 6-C[(4-Fluorphenyl)methyl](methyl)amino}-4-hydroxy-pyridazin-3(2H)-on, 6-[2-(2,6-Difluorphenyl)ethyl]-4-hydroxy-pyridazin-3(2H)-on, 6-[2-(2-Chlor-6-fluorphenyl)ethyl]-4-hydroxy-pyridazin-3(2H)-on, 6-{ [3,5-bis(Trifluormethy I) phenyl] methyl}-4-hydroxypyridazin-3(2H)-on, 6-(l-Phenylethyl)-4-hydroxypyridazin-3(2H)-on, 6-(Cyclopropylmethyl)-4-hydroxy-2,3-dihydropyridazin-3-on,
4-Hydroxy-6-{l-[4-(trifluormethyl)phenyl]cyclopropyl}-2,3-dihydropyridazin-3- on, 6-{2-[2-Chlor-4-(trifluormethyl)phenyl]ethyl}-4-hydroxy-2,3-dihydropyridazin-3- on, 6-{2-[2-Fluor-4-(tnfluormethyl)phenyl]ethyl}-4-hydroxy-2,3-dihydropyridazin-3- on, 6-{2-[3,5-bis(Trifluormethyl)phenyl]ethyl}-4-hydroxy-2,3-dihydropyridazin-3-on, 6-{2-[2,4-bis(Trifluormethyl)phenyl]ethyl}-4-hydroxy-2,3-dihydro-pyridazin-3- on, 6-{2-[3,4-bis(Trifluormethyl)phenyl]ethyl}-4-hydroxy-2,3-dihydropyridazin-3-on,
4-Hydroxy-6-(3-methyl-4-(trifluormethyl)phenethyl)pyridazin-3(2H)-on, 3,4-bis(Benzyloxy)-6-((3-chlor-4-(trifluormethyl)phenyl)ethyl)-pyridazin,
4-Hydroxy-6-{2-[2-methyl-4-(trifluormethyl)phenyl]ethyl}-2,3-dihydropyridazin- 3-on, 6-{2-[3,5-Difluor-4-(trifluormethyl)phenyl]ethyl}-4-hydroxy-2,3- dihydropyridazin-3-on, 6-{2-[3-Fluor-4-(trifluormethyl)phenyl]ethyl}-4-hydroxy-2,3-dihydropyridazin-3- on, og farmaceutisk acceptable salte deraf.
11. Fremgangsmåde til fremstilling af en forbindelse ifølge formel (I) eller et farmaceutisk acceptabelt salt deraf som defineret i krav 1, hvilken fremgangsmåde omfatter (i) når X betegner et svovlatom, eller når X er en binding, og Y betegner et svovlatom, reaktion af en forbindelse ifølge formel (II)
hvor Hal betegner et halogenatom, og R1 er som defineret i formel (I), med en forbindelse ifølge formel (III), HS-[Y]t-R3, hvor t er 0 eller 1, og Y og R3 er som defineret i formel (I); eller (ii) når X betegner SO, eller når X er en binding, og Y betegner SO, oxidering af en forbindelse ifølge formel (IV)
hvor P1 betegner en beskyttelsesgruppe, og R1 er som defineret i formel (I), med et velegnet oxideringsmiddel, efterfulgt af reaktion med en forbindelse ifølge formel (V), L1 -[Y]w_R3, hvor w er 0 eller 1, L1 betegner en fraspaltelig gruppe, og Y og R3 er som defineret i formel (I); eller (iii) når X betegner S02, eller når X er en binding, og Y betegner S02, oxidering af en forbindelse ifølge formel (IV) som defineret i (ii) ovenfor med et velegnet oxideringsmiddel, efterfulgt af reaktion med en forbindelse ifølge formel (V) som defineret i (ii) ovenfor; eller (iv) når X betegner et oxygenatom, eller når X er en binding, og Y betegner et oxygenatom, reaktion af en forbindelse ifølge formel (II) som defineret i (i) ovenfor med en forbindelse ifølge formel (VI), HO-[Y]z-R3, hvor z er 0 eller 1, og Y og R3 er som defineret i formel (I); eller (v) når X betegner C(0), eller når X er en binding, og Y betegner C(O), reaktion af en forbindelse ifølge formel (II) som defineret i (i) ovenfor med carbondioxid, efterfulgt af tilsætning af et aktiveringsmiddel og reaktion med en forbindelse ifølge formel (Va), M-[Y]W-R3, hvor M er Li eller MgR20, R20 betegner et halogenatom, og w, Y og R3 er som defineret i formel (V) i (ii) ovenfor; eller (vi) når X betegner -C(0)NR4, eller når X er en binding, og Y betegner -C(0)NR4, reaktion afen forbindelse ifølge formel (VII)
hvor R1 er som defineret i formel (I), med en forbindelse ifølge formel (VIII), R4HN-[Y]g-R3, hvor g er 0 eller 1, og Y, R3 og R4 er som defineret i formel (I); eller (vii) når X betegner -S(0)2NR4, eller når X er en binding, og Y betegner -S(0)2NR4, reaktion af en forbindelse ifølge formel (II) som defineret i (i) ovenfor med svovdioxid, efterfulgt af tilsætning af et oxiderings-kloreringsmiddel og dernæst reaktion med en forbindelse ifølge formel (VIII) som defineret i (vi) ovenfor; eller (viii) når X betegner -NR4, eller når X er en binding, og Y betegner -NR4, reaktion af en forbindelse ifølge formel (II) som defineret i (i) ovenfor, med en forbindelse ifølge formel (VIII) som defineret i (vi) ovenfor; eller (ix) når X betegner -CR4R5-, eller når X er en binding, og Y betegner -CR4R5-, og R4 og R5 hver uafhængigt af hinanden betegner en Ci-C6-alkylgruppe, reaktion af en forbindelse ifølge formel (II) som defineret i (i) ovenfor med en forbindelse ifølge formel (IX), L2-CR4'R5'-[Y]h-R3, hvor h er 0 eller 1, L2 betegner en fraspaltelig gruppe, R4' og R5' hver uafhængigt af hinanden betegner en Ci-C6-alkylgruppe, og Y og R3 er som defineret i formel (I); eller (x) når X betegner -CR4R5-, eller når X er en binding, og Y betegner -CR4R5-, og R4 og R5 hver uafhængigt af hinanden betegner et hydrogenatom eller en Ci-C6-alkylgruppe, men ikke begge samtidigt betegner en Ci-C6-alkylgruppe, reaktion af en forbindelse ifølge formel (II) som defineret i (i) ovenfor med en forbindelse ifølge formel (IXa), R4C(0)-[Y]h-R3, hvor h, Y og R3 er som defineret i formel (IX) i (ix) ovenfor, og R4 er som defineret i formel (I) ovenfor, efterfulgt af en hydrogeneringsreaktion; eller (xi) når X og Y hver betegner -CHR4, hydrogenering af en forbindelse ifølge formel (X)
hvor R1, R3 og R4 er som defineret i formel (I); eller (xii) når X betegner -CR4R5-, eller når X er en binding, og Y betegner -CR4R5-, og R5 er =CH, reaktion af en forbindelse ifølge formel (XI)
hvor R22 betegner et hydrogenatom eller en Ci-C6-alkylgruppe, og R1 er som defineret i formel (I), med en forbindelse ifølge formel (IXb), R24-CH(R25)-[Y]h-R3, hvor R24 betegner en phosphonatgruppe, R26 betegner et hydrogenatom eller en Ci-C6-alkylgruppe, og h, Y og R3 er som defineret i formel (IX) i (ix) ovenfor; eller (xiii) når X betegner en gruppe
eller når X er en binding, og Y betegner en gruppe
reaktion afen forbindelse ifølge formel (XII)
hvor k er 0 eller 1, og Y, R1 og R3 er som defineret i formel (I), med diiodomethan og zink-kobber-par; eller (xiv) når X betegner en gruppe
eller når X er en binding, og Y betegner en gruppe
reaktion med en forbindelse ifølge formel (XIII)
hvor I er 0 eller 1, og Y, R1 og R3 er som defineret i formel (I), med diiodomethan og zink-kobber-par; og eventuelt derefter udførelse af én eller flere af følgende procedurer: • konvertering af en forbindelse ifølge formel (I) til en anden forbindelse ifølge formel (I) • fjernelse afalle beskyttelsesgrupper • dannelse af et farmaceutisk acceptabelt salt.
12. Farmaceutisk sammensætning omfattende en forbindelse ifølge formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 10, i kombination med et farmaceutisk acceptabelt hjælpestof, fortyndingsmiddel eller bærestof.
13. Forbindelse ifølge formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 10 til anvendelse ved behandling af en lidelse, hvis udvikling eller symptomer er forbundet med D-aminosyreoxidase (DAAO)-enzymaktivitet.
14. Forbindelse ifølge formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 10 til anvendelse ved behandling af schizophreni, schizophreniform lidelse, schizo-affektiv lidelse, kognitive lidelser eller smerte.
15. Kombination af en forbindelse ifølge formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 10 og ét eller flere midler valgt blandt carbamazepin, olanzapin, quetiapin, verapamil, lamotrigin, oxcarbazepin, risperidon, aripiprazol, ziprasidon og lithium.
16. Mellemprodukt ifølge formel (XXX)
hvor P1 og P2 hver uafhængigt af hinanden betegner en benzyl-beskyttelsesgruppe, R20 betegner et hydrogenatom eller en fraspaltelig trimethylsilangruppe, og R1 er som defineret i formel (I) ifølge krav 1.
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