DK2069352T5 - Bestemte kemiske enheder, sammensætninger og fremgangsmåder - Google Patents

Bestemte kemiske enheder, sammensætninger og fremgangsmåder Download PDF

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DK2069352T5
DK2069352T5 DK07810993.1T DK07810993T DK2069352T5 DK 2069352 T5 DK2069352 T5 DK 2069352T5 DK 07810993 T DK07810993 T DK 07810993T DK 2069352 T5 DK2069352 T5 DK 2069352T5
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imidazo
pyrazin
phenylethyl
pentan
enyl
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DK2069352T3 (da
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Alex Muci
Jeffrey T Finer
Pu-Ping Lu
Alan James Russell
Bradley P Morgan
David J Morgans Jr
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Cytokinetics Inc
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    • A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
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Claims (14)

1. Mindst én kemisk enhed valgt fra forbindelser med Formel I og forbindelser med Formel II:
og farmaceutisk acceptable salte deraf, hvor Ri er valgt blandt acyl, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, amino-carbonyl, sulfonyl, sulfanyl, sulfinyl, carboxy og alkoxycarbonyl; R2 er valgt blandt 1-(R)-phenylethyl, 1-(S)-phenylethyl, benzyl, 3-pentyl, 4-heptyl, 4-methyl-1-morpholinopentan-2-yl, isobutyl, cyclohexyl, cyclopropyl, sec-butyl, tert-butyl, isopropyl, 1-hydroxybutan-2-yl, tetrahydro-2H-pyran-4-yl, 1-methoxybutan-2-yl, 1-aminobutan-2-yl og 1-morpholinobutan-2-yl; og R4er H; forudsat, at R1 ikke er hex-1-enyl, hvor "cycloalkyl" refererer til en ikke-aromatisk carbocyklisk ring, som kan være mættet eller have én eller flere carbon-carbon-dobbeltbindinger.
2. Mindst én kemisk enhed ifølge krav 1, hvor Ri er valgt fra acyl, lavere alkyl, alkenyl, alkynyl, lavere alkoxy, og -S-(lavere alkyl), Ri især er valgt fra methyl, ethyl, propyl, hexenyl, butenyl, propenyl, vinyl, ethynyl, methoxy, ethoxy og methylsulfanyl, R^ endnu mere specielt er valgt fra methyl, ethyl, n-propyl, isopropyl, isobuten-1-yl, (Z)-propen-l-yl, (E)-propen-l-yl, propen-2-yl, vinyl, ethynyl, methoxy, ethoxy og methylsulfanyl, hvor "lavere alkyl" refererer til alkylgrupper med 1-7 carbonatomer, og "lavere alkoxy" refererer til alkoxygrupper indeholdende et til seks carbonatomer.
3. Mindst én kemisk enhed valgt fra 1-(ethylpropyl)-6-ethynylimidazo[4,5-b]pyrazin-2-ol; 1 -(ethylpropyl)-6-methoxyimidazo[4,5-b]pyrazin-2-ol; 1-(ethylpropyl)-6-(trifluormethyl)imidazo[4,5-b]pyrazin-2-ol; 1 -[(1 R)-1 -(morpholin-4-ylmethyl)propyl]-6-ethynylimidazo[4,5-b]pyrazin-2-ol; 1-(ethylpropyl)-6-{2-[1-(ethylpropyl)-2-hydroxyimidazo[4,5-e]pyrazin-6-yl]ethynyl}imidazo[4,5-b]pyrazin-2-ol; 6-ethyl-1-(ethylpropyl)imidazo[4,5-b]pyrazin-2-ol; (E)-1-(pentan-3-yl)-6-(prop-1-enyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (E)-1-(pentan-3-yl)-6-(prop-1-enyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (E)-1 -cyclohexyl-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (E)-1-cyclopropyl-6-(prop-1-enyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (E)-1-isopropyl-6-(prop-1-enyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (E)-6-(prop-1 -enyl)-1 -(tetrahydro-2H-pyran-4-yl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (R) -6-(methylthio)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S) -(2-hydroxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-yl)(4-methylpiperazin-1 -yl)methanon; (S)-(2-hydroxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-yl)(morpholino)methanon; (S)-(2-hydroxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-yl)(piperidin-1 -yl)methanon; (S)-1 -(1 -phenylethyl)-6-(piperidin-1 -ylmethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-1 -(1 -phenylethyl)-6-propyl-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-1 -(1 -phenylethyl)-6-vinyl-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-1 -(2-hydroxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-yl)ethanon; (S)-2-hydroxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-carbonitril; (S)-2-hydroxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-carboxamid; (S)-2-hydroxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-carboxylsyre; (S)-2-hydroxy-N,N-dimethyl-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-carboxamid; (S)-2-hydroxy-N-methyl-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-carboxamid; (S)-6-((4-methylpiperazin-1 -yl)methyl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-((dimethylamino)methyl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-(2-hydroxypropan-2-yl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-(2-methylprop-1-enyl)-1-(1-phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-(methylsulfonyl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-(methylthio)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-(morpholinomethyl)-1-(1-phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-cyclohexenyl-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-cyclohexyl-1-(1-phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-ethoxy-1 -{1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-ethyl-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-hexyl-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-isobutyl-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-6-methoxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S)-methyl-2-hydroxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-carboxylat; (S)-N,N-diethyl-2-hydroxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-carboxamid; (S)-N-benzyl-2-hydroxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-6-carboxamid; (S,E)-1 -(1 -phenylethyl)-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S,Z)-1-(1-phenylethyl)-6-(prop-1-enyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (S,Z)-6-(hex-2-enyl)-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol; (Z)-1-(pentan-3-yl)-6-(prop-1-enyl)-1H-imidazo[4,5-b]pyrazin-2-ol; (Z)-1 -cyclohexyl-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (Z)-1 -cyclopropyl-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; (Z)-1-isopropyl-6-(prop-1-enyl)-1H-imidazo[4,5-b]pyrazin-2-ol; (Z)-6-(prop-1 -enyl)-1 -(tetrahydro-2H-pyran-4-yl)-1 H-imidazo[4,5-b]pyrazin-2- ol; 1-(pentan-3-yl)-6-(prop-1-ynyl)-1H-imidazo[4,5-b]pyrazin-2-ol; 1-(pentan-3-yl)-6-(trifluormethyl)-1 H-imidazo[4,5-b]pyrazin-2-ol; 1 -benzyl-6-(methylthio)-1 H-imidazo[4,5-b]pyrazin-2-ol; 1-cyclohexyl-6-(methylthio)-1H-imidazo[4,5-b]pyrazin-2-ol; 1-cyclopropyl-6-(methylthio)-1H-imidazo[4,5-b]pyrazin-2-ol; 1- isopropyl-6-(methylthio)-1H-imidazo[4,5-b]pyrazin-2-ol; 2- hydroxy-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyrazin-6-carbonitril; 6-(methylsulfinyl)-1-((S)-1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol; 6-(methylthio)-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2-ol; 6-(methylthio)-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazo[4,5-b]pyrazin-2-ol; 6-cyclopropyl-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2-ol; 6-ethynyl-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2-ol; 6-methoxy-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2-ol; 6-methyl-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyrazin-2-ol; 1-(ethylpropyl)-6-vinylimidazo[4,5-b]pyrazin-2-ol; 1-(ethylpropyl)-6-(1-methylvinyl)imidazo[4,5-b]pyrazin-2-ol; og 1-(ethylpropyl)-6-(methylethyl)imidazo[4,5-b]pyrazin-2-ol; og farmaceutisk acceptable salte deraf.
4. Mindst én kemisk enhed valgt fra 6-ethynyl-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 6-methoxy-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 1-(pentan-3-yl)-6-(trifluormethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (R)-6-ethynyl-1 -(1 -morpholinobutan-2-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 6-((2-hydroxy-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-6-yl)ethynyl)-1 -pentan-3-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-on; 6-ethyl-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (E)-1-(pentan-3-yl)-6-(prop-1-enyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-on; (E)-1 -cyclohexyl-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (E)-1 -cyclopropyl-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (E)-1 -isopropyl-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (E)-6-(prop-1 -enyl)-1 -(tetrahydro-2H-pyran-4-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (R) -6-(methylthio)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S) -1 -(1 -phenylethyl)-6-(piperidin-1 -ylmethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-1 -(1 -phenylethyl)-6-(piperidin-1 -carbonyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-1-(1-phenylethyl)-6-propyl-1H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-1-(1-phenylethyl)-6-vinyl-1H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-((4-methylpiperazin-1 -yl)methyl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-((dimethylamino)methyl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-(2-hydroxypropan-2-yl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-(2-methylprop-1 -enyl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin- 2(3H)-on; (S)-6-(4-methylpiperazin-1 -carbonyl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-(methylsulfonyl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-(methylthio)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-(morpholin-4-carbonyl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-(morpholinomethyl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-acetyl-1-(1-phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-cyclohexenyl-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-cyclohexyl-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-ethoxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-ethyl-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-hexyl-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-isobutyl-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S)-6-methoxy-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S,E)-1 -(1 -phenylethyl)-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S,Z)-1 -(1 -phenylethyl)-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (S,Z)-6-(hex-2-enyl)-1 -(1 -phenylethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (Z)-1 -(pentan-3-yl)-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (Z)-1 -cyclohexyl-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (Z)-1 -cyclopropyl-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (Z)-1 -isopropyl-6-(prop-1 -enyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; (Z)-6-(prop-1 -enyl)-1 -(tetrahydro-2H-pyran-4-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 1 -(1 -morpholinobutan-2-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 1 -(pentan-3-yl)-6-(prop-1 -ynyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 1-(pentan-3-yl)-6-(trifluormethyl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 1 -benzyl-6-(methylthio)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 1-cyclohexyl-6-(methylthio)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 1-cyclopropyl-6-(methylthio)-1H-imidazo[4,5-b]pyrazin-2(3H)-on; 1-isopropyl-6-(methylthio)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 6-(methylsulfinyl)-1-((S)-1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-on; 6-(methylthio)-1-(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 6-(methylthio)-1-(tetrahydro-2H-pyran-4-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)- on; 6-cyclopropyl-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 6-ethynyl-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 6-methoxy-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 6-methyl-1 -(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 1-(pentan-3-yl)-6-vinyl-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; 1 -(pentan-3-yl)-6-(prop-1 -en-2-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; og 6-isopropyl-1-(pentan-3-yl)-1 H-imidazo[4,5-b]pyrazin-2(3H)-on; og farmaceutisk acceptable salte deraf.
5. Kemisk enhed ifølge krav 3 valgt fra 6-ethynyl-1-(pentan-3-yl)-1H- imidazo[4,5-b]pyrazin-2-ol
og farmaceutisk acceptable salte deraf.
6. Kemisk enhed ifølge krav 4 valgt fra 6-ethynyl-1-(pentan-3-yl)-1H- imidazo[4,5-b]pyrazin-2(3H)-on og farmaceutisk acceptable salte deraf.
7. Farmaceutisk acceptabelt sammensætning, omfattende en farmaceutisk acceptabel bærer og mindst én kemisk enhed ifølge et hvilket som helst af kravene 1 til 6.
8. Farmaceutisk sammensætning ifølge krav 7, hvor sammensætningen er formuleret i en form valgt blandt tabletter, kapsler, pulvere, væsker, suspensioner, suppositorier og aerosoler.
9. Emballeret farmaceutisk sammensætning, omfattende en farmaceutisk sammensætning ifølge krav 7 eller 8 og instruktioner til anvendelse af sammensætningen til behandling af en patient, der lider af en sygdom valgt fra obesitet overvægt, sarkopeni, wasting-syndrom, skrøbelighed, kakeksi, muskelspasme, post-operativ og post-traumatisk muskelsvaghed og en neuromuskulær sygdom.
10. Mindst én kemisk enhed ifølge et hvilket som helst af kravene 1 til 6 til anvendelse ved behandling af en patient med en sygdom valgt fra obesitet, sarkopeni, wasting-syndrom, skrøbelighed, kakeksi, muskelspasme, postoperativ og post-traumatisk muskelsvaghed og en neuromuskulær sygdom.
11. Emballeret farmaceutisk sammensætning ifølge krav 9 eller mindst én kemisk enhed ifølge krav 10 til anvendelse ved behandling af en neuromuskulær sygdom.
12. Anvendelse af en emballeret farmaceutisk sammensætning ifølge krav 9 eller mindst én kemisk enhed ifølge krav 8 til fremstilling af et medikament til behandling af en neuromuskulær sygdom.
13. Emballeret farmaceutisk sammensætning eller mindst én kemisk enhed til anvendelse ifølge krav 11 eller anvendelse ifølge krav 12, hvor den neuromuskulære sygdom er valgt fra gruppen bestående af critical-illness-polyneuropati, prolongeret neuromuskulær blokade, akut myopati, akut inflammatorisk demyeliniserende polyradikuloneuropati, amyotrofisk lateral sklerose, autonom neuropati, Charcot-Marie-Tooth-sygdom, kronisk inflammatorisk demyeliniserende polyradikuloneuropati, dermatomyositis/ polymyositis, diabetisk neuropati, dystrophinopatier, endokrine myopatier, fokale muskelatrofier, hemifaciale spasmer, arvelige neuropatier af typen Charcot-Marie-Tooth-sygdom, inklusionslegememyositis, Kennedy-sygdom, Lambert-Eaton-myasteni-syndrom, muskeldystrofi, metaboliske myopatier, metabolisk neuropati, multifokal motorneuropati med konduktionsblokke, myasthenia gravis, neuropati af Friedreichs ataksi, neuropati af spedalskhed, næringsmæssig neuropati, periodiske paralyser, primær lateral sklerose, restriktiv lungesygdom, sarkoidose og neuropati, Schwartz-Jampel-syndrom, spinal muskelatrofi, stiv-person-syndrom, skjoldbruskkirtelsygdom, traumatiske perifere nervelæsioner og vaskulitisk neuropati.
14. Emballeret farmaceutisk sammensætning eller mindst én kemisk enhed til anvendelse ifølge krav 13 eller anvendelse ifølge krav 13, hvor den neuromuskulære sygdom er valgt fra gruppen bestående af myasthenia gravis og amyotrofisk lateral sklerose.
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