DK2526093T3 - Omvendte amidforbindelser som proteindeacetylasehæmmere og fremgangsmåder til anvendelse deraf - Google Patents
Omvendte amidforbindelser som proteindeacetylasehæmmere og fremgangsmåder til anvendelse deraf Download PDFInfo
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- DK2526093T3 DK2526093T3 DK11735212.0T DK11735212T DK2526093T3 DK 2526093 T3 DK2526093 T3 DK 2526093T3 DK 11735212 T DK11735212 T DK 11735212T DK 2526093 T3 DK2526093 T3 DK 2526093T3
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- optionally substituted
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Claims (24)
1. Forbindelse med formlen I:
eller et farmaceutisk acceptabelt salt eller ester deraf, hvori, Z er N eller CR*, hvori R* er en valgfrit substitueret alkyl, en valgfrit substitueret acyl, en valgfrit substitueret aryl eller en valgfrit substitueret heteroaryl; ring A er en valgfrit substitueret aryl eller en valgfrit substitueret heteroaryl; ring B er en valgfrit substitueret aryl eller en valgfrit substitueret heteroaryl; R1 er (i) H, alkyl, halogenalkyl, alkenyl, aryl, arylalkyl, heteroaryl, heterocyklisk, carbocyklisk, C(0)-R2, C(0)0-R2, eller S(0)p, der hver især valgfrit kan være substitueret; eller (ii) når Z er CR*, kan R^ valgfrit være substitueret forgrenet alkyl, OR3, eller N(R3)(R3)-CH2CH2OH, OCH2CH2OH, SH eller thioalkoxy; R er H eller en valgfrit substitueret alkyl; hvert R2 er uafhængigt alkyl, cycloalkyl, heterocycloalkyl, aryl eller heteroaryl, der hver især er valgfrit substitueret; hvert R3 uafhængigt er alkyl, cycloalkyl, heterocycloalkyl, aryl eller heteroaryl, der hver især valgfrit er substitueret; n er 4, 5, 6, 7 eller 8; og p er 0, 1 eller 2.
2. Forbindelse ifølge krav 1, hvori ring A er phenyl, naphthyl, anthracenyl, pyridinyl, pyrimidinyl, pyrazinyl, indolyl, imidazolyl, oxazolyl, furyl, thienyl, thiazolyl, triazolyl, isoxazolyl, quinolinyl, pyrrolyl, pyrazolyl, eller 5,6,7,8-tetrahydroisoquinolin; der hver især valgfrit kan være substitueret, eller hvori ring B er phenyl, naphthyl, anthracenyl, pyridinyl, pyrimidinyl, pyrazinyl, indolyl, imidazolyl, oxazolyl, furyl, thienyl, thiazolyl, triazolyl, isoxazolyl, quinolinyl, pyrrolyl, pyrazolyl, eller 5,6,7,8-tetrahydroisoquinolin; der hver især valgfrit kan være substitueret, eller hvori R-ι er OH, alkoxy, NH2, NH(alkyl), N(alkyl)(alkyl), NH-aryl, NH-heteroaryl, N(aryl)(aryl), N(aryl)(heteroaryl) eller N(heteroaryl)(heteroaryl).
3. Forbindelse ifølge krav 1, hvori er H, valgfrit substitueret alkyl, valgfrit substitueret aryl eller valgfrit substitueret heteroaryl, eller er OH eller alkoxy, fortrinsvis hvori Fk er H, methyl, ethyl, propyl, i-propyl, butyl, i-butyl, t-butyl, pentyl, hexyl, phenyl, naphthyl, pyridinyl, OH eller OCH3; der hver især valgfrit kan være substitueret.
4. Forbindelse ifølge krav 1, hvori carbonyl og Z-gruppen, der er bundne til ring A, er anbragte para til hinanden, eller hvori carbonyl og Z-gruppen, der er bundne til ring A, er anbragte meta til hinanden, eller hvori carbonyl og Z-gruppen, der er bundne til ring A, er anbragte ortho til hinanden.
5. Forbindelse ifølge krav 1, med formlen II:
eller et farmaceutisk acceptabelt salt eller ester deraf, hvori, hver af Xi, X2, X3 eller X4 uafhængigt er N, CFT, O, S, NCR', CR'CR’, OCR', SCR’; eller fraværende hvori op til tre af Xi, X2, X3 eller X4 kan være N; ring B er en valgfrit substitueret aryl eller en valgfrit substitueret heteroaryl; Ri er H, alkyl, halogenalkyl, alkenyl, aryl, arylalkyl, heteroaryl, heterocyklisk, carbocyklisk, C(0)-R2 eller C(0)0-R2, der hver især kan være valgfrit substitueret; R er H eller en valgfrit substitueret alkyl; hvert R’ uafhængigt er H, valgfrit substitueret alkyl, halogen, OH, NH2, NHR", halogenalkyl, CN, N3, N02; R" er H eller alkyl, og R2 er alkyl, cycloalkyl, heterocycloalkyl, aryl eller heteroaryl, der hver især valgfrit er substitueret.
6. Forbindelse ifølge krav 5, hvori X^ X2, X3, og X4 alle er CR’, eller hvori X2 og X3 er N, og X! og X4 er CR’, eller hvori X2 og X3 er CR’ og X! og X4 er N, eller hvori X2 er N; X3 er S, N eller O; X! er CR’ og X4 er fraværende, eller hvori R, er H, alkyl, aryl, arylalkyl eller heteroaryl, der hver især valgfrit kan være substitueret.
7. Forbindelse ifølge krav 5, hvori ring B er phenyl, pyridinyl, pyrimidinyl eller pyrazinyl; der hver især valgfrit kan være substitueret, fortrinsvis hvori ring B er substitueret med alkyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, aralkyl, halogenalkyl, halogen, OH, NH2, NHR", CN, N3, eller N02.
8. Forbindelse ifølge krav 1, med formlen III:
eller et farmaceutisk acceptabelt salt eller ester deraf, hvori, ring B er en valgfrit substitueret aryl eller en valgfrit substitueret heteroaryl; R, er H, alkyl, halogenalkyl, alkenyl, aryl, arylalkyl, heteroaryl, heterocyklisk, carbocyklisk, C(0)-R2 eller C(0)0-R2, der hver især valgfrit kan være substitueret; R2 valgfrit er substitueret heteroaryl, og R er H eller en valgfrit substitueret alkyl.
9. Forbindelse ifølge krav 8, hvori ring B er phenyl, pyridinyl, pyrimidinyl eller pyrazinyl; der hver især valgfrit kan være substitueret, fortrinsvis hvori ring B er substitueret med alkyl, aryl, aralkyl, halogenalkyl, halogen, OH, NH2, CN, eller N02.
10. Forbindelse ifølge krav 8, hvori Ri er H, alkyl, aryl, arylalkyl, heteroaryl, C(0)-R2 eller C(0)0-R2, der hver især valgfrit kan være substitueret, fortrinsvis hvori R2 valgfrit er substitueret pyridinyl.
11. Forbindelse ifølge krav 1, med formlen IV:
eller et farmaceutisk acceptabelt salt eller ester deraf, hvori, ring B er en valgfrit substitueret aryl eller en valgfrit substitueret heteroaryl; Ri er H, alkyl, halogenalkyl, alkenyl, aryl, arylalkyl, heteroaryl, heterocyklisk eller carbocyklisk, der hver især kan valgfrit være substitueret; og R er H eller en valgfrit substitueret alkyl.
12. Forbindelse ifølge krav 11, hvori ring B er phenyl, pyridinyl, pyrimidinyl eller pyrazinyl; der hver især valgfrit kan være substitueret, fortrinsvis hvori ring B er substitueret med alkyl, aryl, aralkyl, halogenalkyl, halogen, OH, NH2, CN, eller N02.
13. Forbindelse ifølge krav 11, hvori Ri er H, alkyl, aryl, arylalkyl eller heteroaryl, der hver især valgfrit kan være substitueret, fortrinsvis hvori Ri er substitueret med OH eller halogen.
14. Forbindelse ifølge krav 11, hvori forbindelsen med formlen IV er
eller et farmaceutisk acceptabelt salt deraf.
15. Forbindelse ifølge krav 11, hvori forbindelsen med formlen IV er
eller et farmaceutisk acceptabelt salt deraf.
16. Forbindelse ifølge krav 11, hvori forbindelsen med formlen IV er
eller et farmaceutisk acceptabelt salt deraf.
17. Forbindelse ifølge krav 1, med formlen VI:
eller et farmaceutisk acceptabelt salt eller ester deraf, hvori, ring B er en valgfrit substitueret aryl eller en valgfrit substitueret heteroaryl; R* er en valgfrit substitueret alkyl, en valgfrit substitueret aryl eller en valgfrit substitueret heteroaryl; Ri er H, alkyl, aryl, arylalkyl, heteroaryl, heterocyklisk, carbocyklisk, OH, alkoxy, NH2, NH(alkyl) eller N(alkyl)(alkyl); og R er H eller en valgfrit substitueret alkyl.
18. Forbindelse ifølge krav 1, valgt blandt følgende:
19. Farmaceutisk sammensætning omfattende en forbindelse ifølge ethvert af kravene 1-18, eller en farmaceutisk acceptabel ester eller salt deraf sammen med en farmaceutisk acceptabel bærer.
20. Forbindelse ifølge ethvert af kravene 1 til 18 eller farmaceutisk sammensætning ifølge krav 19 til anvendelse som et medikament.
21. Forbindelse ifølge ethvert af kravene 1 til 18 eller farmaceutisk sammensætning ifølge krav 19 til anvendelse i behandling af cancer eller en sygdom med proliferation, fortrinsvis hvori sygdommen er lungecancer, coloncancer, brystcancer, prostatacancer, levercancer, bugspytkirtelscancer, hjernecancer, nyrecancer, ovariecancer, mavecancer, hudcancer, knoglecancer, gastrisk cancer, brystcancer, pancreascancer, gliom, gliobastom, hepatocellulært carcinom, papillært renalcarcinom, pladeepithelcarcinom ved hoved og hals, leukæmier, lymfomer, myelomer, og faste tumorer, eller hvori canceren er myelomatose.
22. Forbindelse ifølge ethvert af kravene 1 til 18 eller farmaceutisk sammensætning ifølge krav 19 til anvendelse i behandling af Wilsons sygdom, spinocerebellær ataksi, prionsygdom, Parkinsons sygdom, Huntingtons sygdom, amytrofisk lateral sklerose, amyloidose, Alzheimers sygdom, Alexanders sygdom, alkoholisk leversygdom, cystisk fibrose, Picks sygdom, spinal muskulær dystrofi eller Lewy body-demens.
23. Forbindelse ifølge ethvert af kravene 1 til 18 eller den farmaceutiske sammensætning ifølge krav 19 til anvendelse ved behandling af rheumatoid arthritis, osteoarthritis; rheumatoid spondylitis; psoriasis; post-iskæmisk perfusionsskade; inflammatorisk tarmsygdom; kronisk inflammatorisk lungesygdom, eksem, astma, psoriasis, iskæmi/reperfusionsskade, ulcerøs colitis, acute respiratory distress syndrome, psoriatisk arthritis, infektiøs arthritis, progressiv kronisk arthritis, deformerende arthritis, osteoarthritis, traumatisk arthritis, urinsur arthritis, Reiters syndrom, polychondritis, akut synovitis og spondylitis, glomerulonephritis, hæmolytisk anæmi, aplastisk anæmi, idiopatisk trombocytopeni, neutropeni, ulcerøs colitis, Crohns sygdom, vært versus transplantatsygdom, allotransplantatafstødning, kronisk thyroiditis, Graves’ sygdom, sklerodermi, diabetes, aktiv hepatitis, primær biliær cirrhose, myasthenia gravis, multipel sklerose (MS), systemisk lupus erythematosus, atopisk dermatitis, kontaktdermatitis, solskoldning af hud, kronisk nyreinsufficiens, Stevens-Johnson’s syndrom, idiopatisk sprue, sarkoidose, Guillain-Barrés syndrom, uveitis, conjunctivitis, keratoconjunctivitis, otitis media, periodontal sygdom, pulmonær interstitiel fibrose af lunge, astma, bronkitis, rhinitis, sinusitis, pneumoconiosis, lungeinsufficienssyndrom, lungeemfysem, lungefibrose, silikose, eller kronisk inflammatorisk lungesygdom.
24. Kit omfattende en forbindelse, der kan inhibere HDAC-aktivitet, hvor forbindelsen er valgt blandt en eller flere forbindelser med formlen I:
eller et farmaceutisk acceptabelt salt eller ester deraf, hvori, Z er N eller CR*, hvori R* er en valgfrit substitueret alkyl, en valgfrit substitueret acyl, en valgfrit substitueret aryl eller en valgfrit substitueret heteroaryl; ring A er en valgfrit substitueret aryl eller en valgfrit substitueret heteroaryl; ring B er en valgfrit substitueret aryl eller en valgfrit substitueret heteroaryl; Ri er (i) H, alkyl, halogenalkyl, alkenyl, aryl, arylalkyl, heteroaryl, heterocyklisk, carbocyklisk, C(0)-R2, C(0)0-R2, eller S(0)p, der hver især valgfrit kan være substitueret; eller (ii) når Z er CR*, kan R! være valgfrit substitueret forgrenet alkyl, OR3 eller N(R3)(R3), -CH2CH2OH, OCH2CH2OH, SH eller thioalkoxy; R er H eller en valgfrit substitueret alkyl; hvert R2 uafhængigt er alkyl, cycloalkyl, heterocycloalkyl, aryl eller heteroaryl, der hver især valgfrit er substitueret; hvert R3 uafhængigt er alkyl, cycloalkyl, heterocycloalkyl, aryl eller heteroaryl, der hver især valgfrit er substitueret; n er 4, 5, 6, 7 eller 8; og p er 0, 1 eller 2; og instruktioner til anvendelse ved behandling af myelom.
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