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DK2860179T3 - Pyrazolopyridinderivater som NADPH-oxidase-hæmmere - Google Patents

Pyrazolopyridinderivater som NADPH-oxidase-hæmmere Download PDF

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DK2860179T3
DK2860179T3 DK14190340.1T DK14190340T DK2860179T3 DK 2860179 T3 DK2860179 T3 DK 2860179T3 DK 14190340 T DK14190340 T DK 14190340T DK 2860179 T3 DK2860179 T3 DK 2860179T3
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optionally substituted
pyrazolo
methyl
alkyl
pyridine
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DK14190340.1T
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Patrick Page
Mike Orchard
Francesca Gaggini
Benoît Laleu
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Genkyotex Suisse Sa
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Claims (21)

1. Pyrazolopyridinderivat med formlen I:
hvor Gi er H; G2 er valgt blandt eventuelt substitueret aryl og eventuelt substitueret heteroaryl; G3 er valgt blandt H; eventuelt substitueret amino; eventuelt substitueret aminoalkyl; eventuelt substitueret aminocarbonyl; eventuelt substitueret alkoxy; eventuelt substitueret alkoxy C1-C6 alkyl; eventuelt substitueret carbonyl; eventuelt substitueret C1-C6 alkyl; eventuelt substitueret C2-C6 alkenyl; eventuelt substitueret C2-C6 alkynyl; eventuelt substitueret aryl; eventuelt substitueret aryl C1-C6 alkyl; eventuelt substitueret heteroaryl; eventuelt substitueret C1-C6 alkyl heteroaryl; eventuelt substitueret heteroaryl C1-C6 alkyl; eventuelt substitueret C2-C6 alkenyl aryl; eventuelt substitueret aryl C2-C6 alkenyl; eventuelt substitueret C2-C6 alkenyl heteroaryl; eventuelt substitueret heteroaryl C2-C6 alkenyl; eventuelt substitueret Cs-Ce-cycloalkyl; eventuelt substitueret heterocycloalkyl; eventuelt substitueret C1-C6 alkyl Cs-Ce-cycloalkyl; eventuelt substitueret Cs-Ce-cycloalkyl C1-C6 alkyl; eventuelt substitueret C1-C6 alkyl heterocycloalkyl and eventuelt substitueret heterocycloalkyl C1-C6 alkyl; G4 er valgt blandt -NR2-C(0)-R1 og -(CHR3)m-(CH2)n-R4, hvor R1 er valgt blandt H; amino; -NR5R6; eventuelt substitueret alkoxy; eventuelt substitueret alkoxy C1-C6 alkyl; eventuelt substitueret aryl; eventuelt substitueret C1-C6 alkyl aryl; eventuelt substitueret aryl C1-C6 alkyl; heteroaryl; eventuelt substitueret C1-C6 alkyl heteroaryl; eventuelt substitueret heteroaryl C1-C6 alkyl; eventuelt substitueret Cs-Ce-cycloalkyl; eventuelt substitueret C1-C6 alkyl Cs-Ce-cycloalkyl; eventuelt substitueret C3-Ce-cycloalkyl C1-C6 alkyl; eventuelt substitueret heterocycloalkyl; eventuelt substitueret C1-C6 alkyl heterocycloalkyl; og eventuelt substitueret heterocycloalkyl C1-C6 alkyl; R2 er valgt blandt H; eventuelt substitueret alkoxy C1-C6 alkyl; eventuelt substitueret aryl; eventuelt substitueret C1-C6 alkyl aryl; eventuelt substitueret aryl C1-C6 alkyl; eventuelt substitueret heteroaryl; eventuelt substitueret C1-C6 alkyl heteroaryl; eventuelt substitueret heteroaryl C1-C6 alkyl; eventuelt substitueret Cs-Cs-cycloalkyl; eventuelt substitueret C1-C6 alkyl Cs-Ce-cycloalkyl; eventuelt substitueret Cs-Ce-cycloalkyl C1-C6 alkyl; eventuelt substitueret heterocycloalkyl; eventuelt substitueret C1-C6 alkyl heterocycloalkyl; eventuelt substitueret heterocycloalkyl C1-C6 alkyl; R3 er valgt blandt H; halogen; eventuelt substitueret alkoxy; eventuelt substitueret alkoxy C1-C6 alkyl aryl; eventuelt substitueret C1-C6 alkyl aryl; eventuelt substitueret aryl C1-C6 alkyl; substitueret heteroaryl; eventuelt substitueret C1-C6 alkyl heteroaryl; eventuelt substitueret heteroaryl C1-C6 alkyl; eventuelt substitueret Cs-Cs-cycloalkyl; eventuelt substitueret C1-C6 alkyl Cs-Cs-cycloalkyl; eventuelt substitueret Cs-Cs-cycloalkyl C1-C6 alkyl; eventuelt substitueret heterocycloalkyl; eventuelt substitueret C1-C6 alkyl heterocycloalkyl; og eventuelt substitueret heterocycloalkyl C1-C6 alkyl; R4 er valgt blandt H;-C(0)R7; -A-B; -CHR8R9 og -(CH2)q-E; R5 og R6 er uafhængigt valgt blandt H; eventuelt substitueret alkoxy C1-C6 alkyl; eventuelt substitueret aryl; eventuelt substitueret C1-C6 alkyl aryl; eventuelt substitueret aryl C1-C6 alkyl; eventuelt substitueret heteroaryl; eventuelt substitueret C1-C6 alkyl heteroaryl; eventuelt substitueret heteroaryl C1-C6 alkyl; eventuelt substitueret Cs-Cs-cycloalkyl; eventuelt substitueret C1-C6 alkyl Cs-Cs-cycloalkyl; eventuelt substitueret Cs-Cs-cycloalkyl C1-C6 alkyl; eventuelt substitueret heterocycloalkyl; eventuelt substitueret C1-C6 alkyl heterocycloalkyl; og eventuelt substitueret heterocycloalkyl C1-C6 alkyl eller-NR5R6 danner sammen en ring valgt blandt eventuelt substitueret heteroaryl og eventuelt substitueret heterocycloalkyl; R7 er valgt blandt eventuelt substitueret amino; eventuelt substitueret alkoxy; eventuelt substitueret aminoalkyl; eventuelt substitueret alkoxy C1-C6 alkyl; eventuelt substitueret C1-C6 alkyl; eventuelt substitueret C2-C6 alkenyl; eventuelt substitueret C2-C6 alkynyl; -NR5R6; eventuelt substitueret aryl; eventuelt substitueret C1-C6 alkyl aryl; eventuelt substitueret aryl C1-C6 alkyl; eventuelt substitueret heteroaryl; eventuelt substitueret C1-C6 alkyl heteroaryl; eventuelt substitueret heteroaryl C1-C6 alkyl; eventuelt substitueret Cs-Ce-cycloalkyl; eventuelt substitueret C1-C6 alkyl Cs-Ce-cycloalkyl; eventuelt substitueret C3-Ce-cycloalkyl C1-C6 alkyl; eventuelt substitueret heterocycloalkyl; eventuelt substitueret C1-C6 alkyl heterocycloalkyl; og eventuelt substitueret heterocycloalkyl C1-C6 alkyl; R8 og R9 er uafhængigt valgt blandt eventuelt substitueret aryl; eventuelt substitueret heteroaryl; eventuelt substitueret Cs-Ce-cycloalkyl og eventuelt substitueret heterocycloalkyl; R10 er valgt blandt H; hydroxyl; eventuelt substitueret amino C1-C6 alkyl; eventuelt substitueret alkoxy C1-C6 alkyl; eventuelt substitueret aryl; eventuelt substitueret C1-C6 alkyl aryl; eventuelt substitueret aryl C1-C6 alkyl; heteroaryl; eventuelt substitueret C1-C6 alkyl heteroaryl; eventuelt substitueret heteroaryl Ci-Ce alkyl; eventuelt substitueret Cs-Ce-cycloalkyl; eventuelt substitueret C1-C6 alkyl Cs-Ce-cycloalkyl; eventuelt substitueret C3-Ce-cyclo-alkyl C1-C6 alkyl; eventuelt substitueret heterocycloalkyl; eventuelt substitueret C1-C6 alkyl heterocycloalkyl; og eventuelt substitueret heterocycloalkyl C1-C6 alkyl; R11 og R12 er uafhængigt valgt blandt H; eventuelt substitueret acyl; eventuelt substitueret CrCe alkyl; eventuelt substitueret C2-C6 alkenyl; eventuelt substitueret C2-C6 alkynyl; eventuelt substitueret aryl; eventuelt substitueret CrCe alkyl aryl; eventuelt substitueret aryl C1-C6 alkyl; eventuelt substitueret heteroaryl; eventuelt substitueret C1-C6 alkyl hetero-aryl; eventuelt substitueret heteroaryl CrCe alkyl; eventuelt substitueret Cs-Ce-cycloalkyl; eventuelt substitueret CrCe alkyl Cs-Ce-cycloalkyl; eventuelt substitueret Cs-Ce-cycloalkyl C1-C6 alkyl; eventuelt substitueret heterocycloalkyl; eventuelt substitueret C1-C6 alkyl heterocycloalkyl; og eventuelt substitueret heterocycloalkyl C1-C6 alkyl eller -NR11R12 danner sammen en ring valgt blandt eventuelt substitueret heteroaryl og eventuelt substitueret heterocycloalkyl; R13 er valgt blandt eventuelt substitueret aryl; eventuelt substitueret heteroaryl; eventuelt substitueret C3-C8-cycloalkyl og eventuelt substitueret heterocycloalkyl; R14, R15 og R16 er uafhængigt valgt blandt H og eventuelt substitueret C1-C6 alkyl; R17 er valgt blandt eventuelt substitueret C1-C6 alkyl; eventuelt substitueret C2-C6 alkenyl; eventuelt substitueret C2-C6 alkynyl; eventuelt substitueret aryl; eventuelt substitueret Ci-C6 alkyl aryl; eventuelt substitueret aryl CrCe alkyl; eventuelt substitueret heteroaryl; eventuelt substitueret CrCe alkyl heteroaryl; eventuelt substitueret heteroaryl CrC6 alkyl; eventuelt substitueret Cs-Ce-cycloalkyl; eventuelt substitueret CrC6 alkyl C3-C8-cycloalkyl; eventuelt substitueret Cs-Ce-cycloalkyl Ci-C6 alkyl; eventuelt substitueret heterocycloalkyl; eventuelt substitueret Ci-C6 alkyl heterocycloalkyl; og eventuelt substitueret heterocycloalkyl Ci-C6 alkyl; A er valgt blandt eventuelt substitueret aryl, og eventuelt substitueret heteroaryl; B er valgt blandt-OR10, -NR11R12 og -(CH2)p-R13; E er valgt blandt eventuelt substitueret C3-Ce-cycloalkyl; eventuelt substitueret C2-Ce alkynyl; -NR14R15; -(CH2)r-OR15 og -NR16C(0)-R17; m, n, p og q er heltal valgt blandt 0 til 5; r er et heltal valgt blandt 3 til 5; G5 er valgt blandt H; eventuelt substitueret CrC6 alkyl; eventuelt substitueret C2-C6 alkenyl; eventuelt substitueret C2-Ce alkynyl; eventuelt substitueret aryl; eventuelt substitueret C1-C6 alkyl aryl; eventuelt substitueret aryl C1-C6 alkyl; eventuelt substitueret heteroaryl; eventuelt substitueret C1-C6 alkyl heteroaryl; eventuelt substitueret heteroaryl Ci-C6 alkyl; eventuelt substitueret C2-C6 alkenyl aryl; eventuelt substitueret aryl C2-C6 alkenyl; eventuelt substitueret C2-Ce alkenyl heteroaryl; eventuelt substitueret heteroaryl C2-C6 alkenyl; eventuelt substitueret Cs-Ce-cycloalkyl; eventuelt substitueret heterocycloalkyl; eventuelt substitueret CrCe alkyl C3-Ce-cyclo-alkyl; eventuelt substitueret Cs-Ce-cycloalkyl Ci-Ce alkyl; eventuelt substitueret Ci-Ce alkyl heterocycloalkyl og eventuelt substitueret heterocycloalkyl Ci-Ce alkyl; tauto-merer, geometriske isomerer, optisk aktive former som enantiomerer, diastereomerer og racematformer, samt farmaceutisk acceptable salte deraf.
2. Derivat ifølge krav 1, hvor G2 er eventuelt substitueret phenyl.
3. Derivat ifølge krav 1 eller 2, hvor G3 er eventuelt substitueret aryl.
4. Derivat ifølge ethvert af kravene 1 til 3, hvor G4 er-(CHR3)m-(CH2)n-R4; R3, R4, m og n er som angivet i ethvert af de foregående krav.
5. Derivat ifølge ethvert af de foregående krav, hvor R4 er -(Chbjq-E; E og q er definerede i ethvert af de foregående krav.
6. Derivat ifølge ethvert af de foregående krav, hvor Gs er H.
7. Farmaceutisk sammensætning indeholdende i det mindste ét derivat ifølge ethvert af kravene 1 til 6 og et farmaceutisk acceptabelt bærestof, fortyndingsmiddel eller excipiens for dette.
8. Derivat ifølge ethvert af kravene 1 til 6 til anvendelse som et medikament.
9. Pyrazolopyridinderivat ifølge ethvert af kravene 1 til 6 til anvendelse ved profylakse og/eller behandling af en sygdom eller tilstand valgt blandt hjertekarsygdomme, sygdomme i åndedrætsvejene, stofskifteforstyrrelser, hudlidelser, knoglelidelser, neuro-inflammatoriske og/eller neurodegenerative lidelser, nyresygdomme, forplantningssygdomme, sygdomme, der rammer øjet og/eller linsen og/eller tilstande, der rammer det indre øre, inflammatoriske lidelser, leversygdomme, smerte, cancere, allergiske lidelser, traumatiseringer, septisk, hæmorrhagisk og anafylaktisk chok, sygdomme eller lidelser i mave-tarmsystemet, angiogenese, angiogenese-afhængige tilstande og andre sygdomme og/eller lidelser der står i forbindelse med nikotinamid-adenin-di-nucleotidphosphatoxidase (NADPH Oxidase).
10. Pyrazolopyridinderivat til anvendelse ifølge krav 9, hvor nyrelidelsen eller lidelserne er valgt blandt diabetisk nephropati, nyresvigt, glomerulonephritis, nephro-toksicitet af aminoglycosider og platinforbindelser og hyperaktiv blære.
11. Pyrazolopyridinderivat til anvendelse ifølge krav 9, hvor leversygdommen eller lidelsen er valgt blandt leverfibrose, alkoholinduceret fibrose, steatose og ikke-alko-holisk steatohepatitis.
12. Pyrazolopyridinderivat til anvendelse ifølge krav 9, hvor åndedrætslidelsen er valgt blandt bronchial astma, bronchitis, allergisk rhinitis, voksen respirationssyndrom, viral lungeinfektion (influenza), pulmonær hypertension og kronisk obstruktiv pulmonær lidelse (COPD).
13. Pyrazolopyridinderivat til anvendelse ifølge krav 9, hvor lidelsen knyttet til niko-tinamid-adenin-dinucleotidphosphatoxidase (NADPH Oxidase) er idiopatisk pulmonær fibrose.
14. Pyrazolopyridinderivat til anvendelse ifølge krav 9, hvor forplantningslidelsen eller sygdommen er valgt blandt erektil dysfunktion, fertilitetslidelser, prostatahypertrofi og ondartet prostatahypertrofi.
15. Pyrazolopyridinderivat til anvendelse ifølge krav 9, hvor canceren er valgt blandt fibrosarcoma, myxosarcoma, liposarcoma, chondrosarcoma, osteogenisk sarcoma, chordoma, angiosarcoma, endotheliumsarcoma, lymphangiosarcoma, lymphangioendothelioma, periosteoma, mesothelioma, Ewing's tumor, leiomyosarcoma, rhabdomyosarcoma, colon carcinoma, pankreatisk cancer, brystcancer, ovariecancer, nyrecancer, prostatacarcinoma, pladecellecarcinoma, basal cellecarcinoma, adenocarcinoma, svedkirtelcarcinoma, talgcellecarcinoma, papillær carcinoma, papillær adenocarcinoma, cystadenocarcinoma, medullær carcinoma, bronchogenisk carcinoma, nyrecellecarcinoma, levercellecarcinoma, cholangiocarcinoma, choriocarcinoma, seminoma, embryonal carcinoma, Wilms' tumor, cervical cancer, orchioncus, lungecancer, småcellet lungecancer, lungeadenocarcinoma, blærecancer og epithelial cancer.
16. Pyrazolopyridinderivat til anvendelse ifølge krav 9, hvor smerten er en hyperalgesi associeret med inflammatorisk smerte.
17. Pyrazolopyridinderivat til anvendelse ifølge krav 9, hvor knoglelidelsen er valgt blandt osteoporose, osteoporase, osteosclerose, periodontitis og hyperparathyroi-disme.
18. Pyrazolopyridinderivat til anvendelse ifølge krav 9, hvor sygdommen eller lidelsen, som påvirker øjet og/eller linsen er valgt blandt katarakt omfattende diabetisk katarakt, gen-opacificering af linsen efter katarakt kirurgi, diabetisk og andre former for retino-pati.
19. Pyrazolopyridinderivat til anvendelse ifølge krav 9, hvor den kardiovaskulære lidelse eller sygdom er valgt blandt atherosclerose, især sygdomme eller lidelser knyttet til endothelial dysfunktion inkl. men ikke begrænset til hypertension, kardiovaskulær komplikationer af Type I eller Type II diabetes, intim hyperplasi, koronær hjertesygdom, cerebral, koronær og arterial vasospasme, endothelial dysfunktion, hjerteinsufiens inkl. kongestiv hjerteinsufiens, perifere arteriesygdom, restenose, trauma forårsaget af en stent, slagtilfælde, iskæmisk attack, vaskulære komplikation, såsom efter organtransplantation, myokardiel infarkt, hypertension, dannelse af atherosclerotisk plaq, pladeaggregation, angina pectoris, aneurisme, aortisk dissektion, iskæmisk hjertesygdom, kardial hypertrofi, pulmonær embolus, thrombotiske begivenheder, inkl. dyb venethrombose, skade forårsaget efter iskæmi ved genetablering af blodstrømning eller oxygentilførsel som ved organtransplantation, åben hjertekirurgi, angioplasti, hæmorrhagisk chok, angioplasti af iskæmiske organer inkl. hjerte, hjerne, lever, nyre, nethinde og tarm.
20. Pyrazolopyridinderivat til anvendelse ifølge ethvert af kravene 10 til 19, hvor pyrazolopyridinderivatet er valgt fra følgende gruppe: 2-(2-chlorphenyl)-4-methyl-5-(2-morpholin-4-ylbenzyl)-1H-pyrazolo[4,3-c]pyridin- 3,6(2H,5H)-dion; 2-(2-chlorphenyl)-4-methyl-5-{4-[(4-methylpiperazin-1-yl)methyl]benzyl}-1H-pyrazolo- [4,3-c]pyridin-3,6(2H,5H)-dion; 2-(2-chlorphenyl)-4-methyl-5-(2-morpholin-4-yl-2-phenylethyl)-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2-(2-chlorphenyl)-5-[2-(4-hydroxyphenyl)ethyl]-4-methyl-1H-pyrazolo[4,3-c]pyridin-3,6- (2H,5H)-dion; 5-(3-ethoxypropyl)-4-methyl-2-(4-phenyl-1,3-thiazol-2-yl)-1 H-pyrazolo[4,3-c]pyridin- 3,6-(2H,5H)-dion; 2-(2-chlorphenyl)-4,5-dimethyl-1 H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(2-fluorphenyl)-4,5-dimethyl-1H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 4- methyl-5-(3-phenoxybenzyl)-2-(4-phenyl-1,3-thiazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 4,5-dimethyl-2-(4-phenyl-1,3-thiazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(3-chlorphenyl)-4,5-dimethyl-1 H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; N-[2-(2-chlorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin- 5- yl]-2-(4-fluorphenoxy)acetamid; 2-(2-chlorphenyl)-4-methyl-5-(3-phenoxybenzyl)-1 H-pyrazolo[4,3-c]pyridin-3,6-(2H,5H)-dion; 5-(3-ethoxypropyl)-2-(2-fluorphenyl)-4-methyl-1 H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(3-chlorphenyl)-5-(3-ethoxypropyl)-4-methyl-1 H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(3-chlorphenyl)-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2-(2-fluorphenyl)-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2-(2-fluorphenyl)-4-methyl-5-[(6-morpholin-4-ylpyridin-2-yl)methyl]-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2-(2-fluorphenyl)-4-methyl-5-[4-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2- (3-chlorphenyl)-4-methyl-5-[(6-morpholin-4-ylpyridin-2-yl)methyl]-1 H-pyrazolo-[4,3-c]pyridin-3,6(2H,5H)-dion; 3- (4,5-dimethyl-3,6-dioxo-1,3,5,6-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl)benzonitril; 2-(2-fluorphenyl)-4-methyl-5-(3-phenoxybenzyl)-1H-pyrazolo[4,3-c]pyridin-3,6 (2H,5H)-dion; 2-(3-chlorphenyl)-4-methyl-5-(3-phenoxybenzyl)-1 H-pyrazolo[4,3-c]pyridin-3,6-(2H,5H)-dion; 2-(2-chlorphenyl)-5-(3-ethoxypropyl)-4-methyl-1 H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(2-chlorphenyl)-4-methyl-5-[(6-morpholin-4-ylpyridin-2-yl)methyl]-1 H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; 2-(3-chlorphenyl)-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1 H-pyrazolo- [4,3-c]pyndin-3,6(2H,5H)-dion; 2-(3-chlorphenyl)-4-methyl-5-[4-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2-[2-(2-fluorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]-N-(pyridin-2-ylmethyl)acetamid; 2-(2-chlorphenyl)-4-methyl-5-[4-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2- (2-chlorphenyl)-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; 4- methyl-5-(3-phenoxybenzyl)-2-[1,2,4]triazolo[4,3-b]pyridazin-6-yl-1 H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; 3- [5-(3-ethoxypropyl)-4-methyl-3,6-dioxo-1,3,5,6-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl]benzonitril; 2-[4-(benzyloxy)phenyl]-4,5-dimethyl-1H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-[4-(benzyloxy)phenyl]-4-methyl-5-(3-phenoxybenzyl)-1H-pyrazolo[4,3-c]pyridin- 3,6(2H,5H)-dion; 2- [4-(benzyloxy)phenyl]-5-(3-ethoxypropyl)-4-methyl-1H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 3- 4-methyl-5-[4-(morpholin-4-ylmethyl)benzyl]-3,6-dioxo-1,3,5,6-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl}benzonitril; 2-(2-chlorphenyl)-5-(3-hydroxypropyl)-4-methyl-1H-pyrazolo[4,3-c]pyridin-3,6 (2H,5H)-dion; 2-[2-(2-chlorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]-N-(pyridin-2-ylmethyl)acetamid; 2-[2-(3-cyanophenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin- 5- yl]-N-(pyridin-2-ylmethyl)acetamid; 2-[2-(3-chlorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]-N-(pyridin-2-ylmethyl)acetamid; 2-(2-chlorphenyl)-5-[3-(diethylamino)propyl]-4-methyl-1H-pyrazolo[4,3-c]pyridin-3,6- (2H,5H)-dion; 2-(2-chlorphenyl)-5-(cyclohexylmethyl)-4-methyl-1H-pyrazolo[4,3-c]pyridin-3,6- (2H,5H)-dion; 2-(3-chlorphenyl)-5-(3-hydroxypropyl)-4-methyl-1H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)- dion; 2-(2-chlorphenyl)-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1 H-pyrazolo-[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(2-chlorphenyl)-5-(3-phenoxybenzyl)-1 H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(3-chlorphenyl)-4-methyl-5-(3-morpholin-4-yl-3-phenylpropyl)-1 H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; 2-(3-chlorphenyl)-4-methyl-5-(3-phenylprop-2-yn-1-yl)-1H-pyrazolo[4,3-c]pyridin-3,6- (2H,5H)-dion; 2-(2-chlor-4-fluorphenyl)-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo- [4,3-c]pyridin-3,6(2H,5H)-dion; 4,5-dimethyl-2-{5-[(4-methylpiperazin-1-yl)sulfonyl]pyridin-2-yl}-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2-(2-fluorphenyl)-4-methyl-5-(3-morpholin-4-yl-3-phenylpropyl)-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2-(2,5-dichlorphenyl)-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1 H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; 2-[2-(benzyloxy)phenyl]-5-(3-ethoxypropyl)-4-methyl-1H-pyrazolo[4,3-c]pyridin-3,6- (2H,5H)-dion; 2-(2,5-dichlorphenyl)-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1 H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; N-{2-[2-(2,5-dichlorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]- pyridin-5-yl]ethyl{acetamid; 2-(2-chlor-4-fluorphenyl)-4-(methoxymethyl)-5-[2-(morpholin-4-ylmethyl)benzyl]-1 H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(2-chlorphenyl)-5-[2-(dimethylamino)ethyl]-4-methyl-1 H-pyrazolo[4,3-c]pyridin-3,6-(2H,5H)-dion; 2-[4-(benzyloxy)phenyl]-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1 H-pyrazolo-[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(3-chlorphenyl)-4-methyl-5-[2-(4-methylpiperazin-1-yl)benzyl]-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2-(3,4-dichlorphenyl)-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1H-pyrazolo- [4,3-c]pyridin-3,6(2H,5H)-dion; 5-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]-2-(2,5-dichlorphenyl)-4-methyl-1 H-pyrazolo-[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(2-chlorphenyl)-4-methyl-5-(3-phenylprop-2-yn-1-yl)-1H-pyrazolo[4,3-c]pyridin-3,6- (2H,5H)-dion; N-{3-[5-(3-ethoxypropyl)-4-methyl-3,6-dioxo-1,3,5,6-tetrahydro-2H-pyrazolo[4,3-c]- pyridin-2-yl]phenyl}acetamid; 2-benzyl-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1 H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(3,4-dichlorphenyl)-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1 H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; 2-(2-chlor-4-fluorphenyl)-4,5-dimethyl-1 H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-[4-(benzyloxy)phenyl]-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2-(3,4-dichlorphenyl)-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1 H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; methyl [2-(2,5-dichlorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]-pyridin-5-yl]; N-{3-[2-(2,3-dichlorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]- pyridin-5-yl]phenyl}acetamid; 2-(2,3-dichlorphenyl)-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1H-pyrazolo- [4,3-c]pyridin-3,6(2H,5H)-dion; N-{3-[2-(3-chlor-4-fluorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo-[4,3-c]pyridin-5-yl]phenyl}acetamid; 5-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]-2-(3,4-dichlorphenyl)-4-methyl-1 H-pyra-zolo[4,3-c]pyridin-3,6(2H,5H)-dion; N-{3-[2-(2-chlor-4-fluorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo-[4,3-c]pyridin-5-yl]phenyl}acetamid; 2-(3-chlorphenyl)-5-(3-ethoxypropyl)-4-(3-methoxybenzyl)-1 H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(3-chlor-4-fluorphenyl)-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1 H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; 2-(3-chlor-4-fluorphenyl)-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1H- pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(2-chlor-4-fluorphenyl)-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1 H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; 5-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]-2-(2-chlor-4-fluorphenyl)-4-methyl-1H-pyra- zolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-[4-(benzyloxy)phenyl]-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1 H-pyra-zolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(2,3-dichlorphenyl)-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1 H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; 2-(2-chlor-4-fluorphenyl)-4-methyl-5-[2-(4-methylpiperazin-1-yl)benzyl]-1 H-pyra-zolo[4,3-c]pyridin-3,6(2H,5H)-dion; N-(3-{[2-(3-chlor-4-fluorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]methyl}phenyl)acetamid; 5-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]-2-(3-chlor-4-fluorphenyl)-4-methyl-1H-pyra- zolo[4,3-c]pyridin-3,6(2H,5H)-dion N-(3-{[2-(2-chlor-4-fluorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo-[4,3-c]pyridin-5-yl]methyl}phenyl)acetamid; 2- (2-chlor-4-fluorphenyl)-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1H-pyra-zolo[4,3-c]pyridin-3,6(2H,5H)-dion; 3- {4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-3,6-dioxo-1,3,5,6-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl}benzonitril; N-{2-[2-(3-chlor-4-fluorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo-[4,3-c]pyridin-5-yl]ethyl}-4-fluorbenzamid; N-{2-[2-(2-chlor-4-fluorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo-[4,3-c]pyridin-5-yl]ethyl}-4-fluorbenzamid; 2-[2-(2-chlor-4-fluorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]- pyridin-5-yl]-N-(pyridin-2-ylmethyl)acetamid; N-(2-{2-[4-(benzyloxy)phenyl]-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo- [4,3-c]pyridin-5-yl{ethyl)-4-fluorbenzamid; 2-(3-chlor-4-fluorphenyl)-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo- [4,3-c]pyridin-3,6(2H,5H)-dion; N-(3-{4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-3,6-dioxo-1,3,5,6-tetrahydro-2H- pyrazolo[4,3-c]pyridin-2-yl}phenyl)acetamid; 2-(4-chlorphenyl)-4-methyl-5-(3-phenoxybenzyl)-1 H-pyrazolo[4,3-c]pyridin-3,6-(2H,5H)-dion; 2-[2-(3-chlor-4-fluorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]- pyridin-5-yl]-N-(pyridin-2-ylmethyl)acetamid; 2-[4-butyl-2-(3-chlor-4-fluorphenyl)-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]- pyridin-5-yl]-N-(pyridin-2-ylmethyl)acetamid; 2-[2-(2,3-dichlorphenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]-pyridin-5-yl]-N-(pyridin-2-ylmethyl)acetamid; 2-[2,4-bis(3-chlorphenyl)-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]-N-(pyridin-2-ylmethyl)acetamid; 2,4-bis(3-chlorphenyl)-5-(3-hydroxypropyl)-1H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(2-chlorphenyl)-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1 H-pyrazolo[4,3-c]-pyridin-3,6(2H,5H)-dion; N-{3-[4-(3-chlorphenyl)-5-(3-hydroxypropyl)-3,6-dioxo-1,3,5,6-tetrahydro-2H-pyra- zolo[4,3-c]pyridin-2-yl]phenyl}acetamid; 2-(2-chlorphenyl)-4-methyl-5-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1 H-pyrazolo-[4,3-c]pyridin-3,6(2H,5H)-dion; 2-(2-chlorphenyl)-4-(4-chlorphenyl)-5-(3-ethoxypropyl)-1H-pyrazolo[4,3-c]pyridin- 3,6(2H,5H)-dion; 2-(2-chlorphenyl)-4-(4-chlorphenyl)-5-methyl-1H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)- dion; 2-(2-chlorphenyl)-4-(2-fluorphenyl)-5-methyl-1H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)- dion; 2-(2-chlorphenyl)-4-(4-chlorphenyl)-5-[3-(dimethylamino)propyl]-1H-pyrazolo[4,3-c]- pyridin-3,6(2H,5H)-dion; 2-(2-chlorphenyl)-4-[3-(dimethylamino)phenyl]-5-methyl-1H-pyrazolo[4,3-c]pyridin- 3,6(2H,5H)-dion; 2-(2-chlorphenyl)-5-methyl-4-(3-morpholin-4-ylphenyl)-1H-pyrazolo[4,3-c]pyridin- 3,6(2H,5H)-dion; 2-(2-chlorphenyl)-4-[1-(3,4-difluorphenoxy)ethyl]-5-methyl-1H-pyrazolo[4,3-c]pyridin- 3,6(2H,5H)-dion; 4-[1-(benzyloxy)ethyl]-2-(2-chlorphenyl)-5-methyl-1 H-pyrazolo[4,3-c]pyridin-3,6-(2H,5H)-dion; og 4-[3-(dimethylamino)phenyl]-2-(2-methoxyphenyl)-5-methyl-1H-pyrazolo[4,3-c]pyridin- 3,6(2H,5H)-dion.
21. Pyrazolopyridinderivat til anvendelse ifølge krav 20, hvor pyrazolopyridinderivatet er 2-(2-chlorphenyl)-4-[3-(dimethylamino)phenyl]-5-methyl-1H-pyrazolo[4,3-c]pyridin-3,6(2H,5H)-dion.
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