DK2552890T3 - Polycycliske tetracyclinforbindelser - Google Patents

Polycycliske tetracyclinforbindelser Download PDF

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DK2552890T3
DK2552890T3 DK11715112.6T DK11715112T DK2552890T3 DK 2552890 T3 DK2552890 T3 DK 2552890T3 DK 11715112 T DK11715112 T DK 11715112T DK 2552890 T3 DK2552890 T3 DK 2552890T3
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alkyl
ring
mmol
alkylene
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Xiao-Yi Xiao
Roger Clark
Diana Hunt
Magnus RÖNN
Louis Plamondon
Minsheng He
Joyce Sutcliffe
Trudy Grossman
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Tetraphase Pharmaceuticals Inc
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Claims (21)

1. Forbindelse med strukturformel I:
eller et farmaceutisk acceptabelt salt deraf, hvor: X er valgt fra halo, -R, -OR, -SR, -S(0)mR, -N(R)2, -N(R)C(0)R, N(R)C(0)0R', og N(R)S(0)mR', hvor: hver R er uafhængigt valgt fra H, (Ci-C6)alkyl, carbocyclyl, eller heterocyclyl; eller to R-grupper taget sammen med det atom eller atomer til hvilke de er bundet danner en 4-7-leddet ikke-aromatisk heterocyclyl; og R' er (Ci-Ce)alkyl, carbocyclyl, eller heterocyclyl; ring A er valgt fra:
R1 er valgt fra hydrogen, -(Ci-Cs)alkyl, -(Co-C6)alkylen-carbocyclyl, -(Co-C6)alkylen-heterocyclyl, -(Ci-C6)alkylen-0-(Ci-C6)alkyl, -(C2-C6)alkylen-0-carbocyclyl, -(C2-C6)alkylen-0-heterocyclyl, -S(0)m-(Ci-C6)alkyl, -S(0)m-carbocyclyl, -S(0)m-heterocyclyl, -(C2-C4)alkylen-S(0)m-carbocyclyl, -(C2-C4)alkylen-S(0)m-heterocyclyl, -C(0)-[C(R4)(R4)]o-4-N(R2)(R3), -C(0)-(Ci-Ce)alkyl, -C(0)-heterocyclyl, -C(0)-carbocyclyl, -S(0)m-[C(R4)(R4)]o-4-N(R2)(R3), og -S(0)m-(Ci-C4)alkylen-carbocyclyl, -S(0)m-(Ci-C4)alkylen-heterocyclyl; eller R1 taget sammen med et ringatom tilgrænsende nitrogenatomet til hvilket R1 er bundet danner en mættet heterocyclisk ring kondenseret til ring A; R6a er valgt fra hydrogen og methyl; og R6 er valgt fra hydrogen, (Ci-C4)alkyl eventuelt substitueret med hydroxy eller phenyl; eller R6 taget sammen med R1 og nitrogenatomet og carbonatomet til hvilke de respektivt er bundet danner en pyrrolidinyl- eller piperidinylring kondenseret til ring A, hvor pyrrolidinyl- eller piperidinylringen eventuelt er substitueret med -OH eller -F; eller R6 og R6a er taget sammen med carbonatomet til hvilket de begge er bundet for at danne en cyclopropylring; og R7a og R7b hver er hydrogen eller taget sammen danner =0 hver af R2 og R3 er uafhængigt valgt fra hydrogen, (Ci-Cs)alkyl, -(C0-C6) alkylen-carbocyclyl, -(Co-C6)alkylen-heterocyclyl, -(C2-Ce)alkylen-0-carbocyclyl, -(C2-C6)alkylen-0-heterocyclyl, -S(0)m-(Ci-C6)alkyl, -S(0)m-carbocyclyl, -S(0)m-heterocyclyl, -(C2-C4)alkylen-S(0)m-carbocyclyl, og -(C2-C4)alkylen-S(0)m-heterocyclyl; eller R2 og R3, taget sammen med nitrogenatomet til hvilket de er bundet danner heterocyclyl, hvor heterocyclylen eventuelt omfatter 1 til 4 yderligere heteroatomer uafhængigt valgt fra N, S og O; hver R4 er uafhængigt valgt fra hydrogen, (Ci-Ce)alkyl, carbocyclyl, heterocyclyl eller en naturligt forekommende aminosyresidekædeenhed, eller to R4 taget sammen med et fælles carbonatom til hvilket de er bundet danner 3-7-leddet ikke-aromatisk carbocyclyl eller en 4-7-leddet ikke-aromatisk heterocyclyl, hvor heterocyclylen dannet af to R4 omfatter et til tre heteroatomer uafhængigt valgt fra N, S og O; et hvilket som helst substituerbart carbonatom på ring A er eventuelt: (i) mættet med en eller to substituenter uafhængigt valgt fra -(Ci-C4)alkyl, og -(Co-C4)alkylen-carbocyclyl; eller (ii) mættet med =0; (iii) taget sammen med et tilgrænsende ringatom for at danne en 3-7-leddet mættet carbocyclyl eller en 4-7-leddet mættet heterocyclylring; eller (iv) spirokondenseret til en 3-7-leddet mættet carbocyclyl; en hvilken som helst yderligere N-heteroatom på ring A er mættet med hydrogen, (Ci-Ce) alkyl, carbocyclyl, eller heterocyclyl; hver alkyl eller alkylen i strukturformel I er eventuelt og uafhængigt substitueret med én eller flere substituenter uafhængigt valgt fra halo, -OH, =0, -0-(Ci-C4)alkyl, fluor-mættet-(Ci-C4)alkyl, -S(0)m-(Ci-C4)alkyl og -N(R5)(R5); hver carbocyclyl eller heterocyclyldel af en substituent af ring A eller den mættede heterocycliske ring kondenseret til ring A er eventuelt og uafhængigt substitueret med én eller flere substituenter uafhængigt valgt fra halo, -(Ci-C4)alkyl, -OH, =0, -0-(Ci-C4)alkyl, -(Ci-C4)alkylen-0-(Ci-C4)alkyl, halo-mættet-(Ci-C4)alkyl, halo-mættet-0-(Ci-C4)alkyl, -C(0)-(Ci-C4)alkyl, -C(0)-(fluor-mættet-(Ci-C4)alkyl), -S(0)m-(Ci-C4)alkyl, -N(R5)(R5) og CN; hver R5 er uafhængigt valgt fra hydrogen og (Ci-C4)alkyl, hvor hver alkyl i gruppen vist med R5 er eventuelt er og uafhængigt substitueret med én eller flere substituenter uafhængigt valgt fra -(Ci-C4)alkyl, (C3-C6)cycloalkyl, halo, -OH, -0-(Ci-C4)alkyl, og -(Ci-C4)alkylen-0-(Ci-C4)alkyl; og hver m er uafhængigt 1 eller 2, med det forbehold at når X er hydrogen, er ring A ikke et usubstitueret bivalent piperidinradikal.
2. Forbindelsen ifølge krav 1, hvor: X er valgt fra halo, -R', -OR, -SR, -S(0)mR, -N(R)2, -N(R)C(0)R, N(R)C(0)0R', og N(R)S(0)mR'; X er valgt fra fluor, chlor, hydrogen, methoxy, methyl, trifluormethyl, trifluormethoxy og dimethylamino; eller X er valgt fra fluor, chlor, methoxy, methyl, trifluormethyl, trifluormethoxy og dimethylamino.
3. Forbindelsen ifølge et hvilket som helst af kravene 1-2, hvor R1 er valgt fra hydrogen, - (Ci-Ce)alkyl, -(C2-C4)alkylen-0-(Ci-C4)alkyl, -(Co-C3)alkylen-(mættet heterocykel), -(Co-C3)alkylen-(C3-C7)cycloalkyl, -C(0)-(CH2)i-3-N(R2)(R3); eller R1 taget sammen med et ringatom tilgrænsende nitrogenatomet til hvilket R1 er bundet danner en mættet heterocyclisk ring kondenseret til ring A; hvor: en hvilken som helst alkyl- eller alkylendel af R1 eller den mættede heterocycliske ring kondenseret til ring A eventuelt er substitueret med fluor eller hydroxy; R2 er valgt fra hydrogen og (Ci-C3)alkyl; R3 er valgt fra (Ci-C3)alkyl og (C3-C7)cycloalkyl, eller R2 og R3, taget sammen med nitrogenatomet til hvilket de er bundet danner 4-7-leddet mættet heterocyclyl, hvor heterocyclylen eventuelt er substitueret med fluor.
4. Forbindelsen ifølge krav 3, hvor R1 er valgt fra hydrogen; (Ci-Cs)lige alkyl eventuelt substitueret med én eller flere af: 1 til 5 methylgrupper, en enkelt hydroxygruppe, og 1 til 3 fluorgrupper; (C3-C7)cycloalkyl; tetrahydrofuranyl; og -C(0)-CH2-N(R2)(R3)f hvor R2 og R3 er simultant methyl; R2 er hydrogen og R3 er C3-C7 cycloalkyl; eller R2 og R3, taget sammen med nitrogenatomet til hvilket de er bundet danner pyrrolidinylring eventuelt substitueret med fluor, eller R1 taget sammen med et ringatom tilgrænsende nitrogenatomet til hvilket R1 er bundet danner en pyrrolidinyl- eller piperidinylring kondenseret til ring A, hvor pyrrolidinyl- eller piperidinylringen kondenseret til ring A eventuelt er substitueret med hydroxy eller fluor.
5. Forbindelsen ifølge krav 1, hvor: ring A er valgt fra
6. Forbindelsen ifølge krav 1, hvor: ring A er
X er valgt fra fluor, chlor, methoxy, trifluormethyl, og dimethylamino; og R1 er valgt fra ethyl, propyl, (C3-C5)forgrenet alkyl, (C3-C5)cycloalkyl, (Ci-C3)alkylen-cyclopropyl, -C(0)CH2NH-cyclopentyl, og -C(0)CH2-pyrrolidin-l-yl, hvor R1 eventuelt er substitueret med fluor.
7. Forbindelsen ifølge krav 1, hvor: ring A er
X er fluor; og R1 er valgt fra hydrogen, (Ci-C4)alkyl; eventuelt hvor R1 er valgt fra isopropyl, propyl eller ethyl.
8. Forbindelsen ifølge krav 1, hvor: ring A er
X er fluor; R1 er valgt fra hydrogen, (Ci-C4)alkyl; R6 er valgt fra hydrogen, (R)-(Ci-C4)alkyl, eller -Chte-phenyl, eller R1 og R6 taget sammen med nitrogenatomet og carbonatomet til hvilket de respektivt er bundet danner en pyrrolidinylring kondenseret til ring A; R7a og R7b hver er hydrogen eller taget sammen danner =0; hvor mindst én af R1, og R6 er en anden end hydrogen; eventuelt hvor: R1 er valgt fra hydrogen, methyl, isobutyl, og tert-butyl; og R6 er valgt fra hydrogen, (R)-methyl, (R)-isobutyl, (R)-sec-butyl, (/?)-isopropyl, og -Chb-phenyl, eller R1 og R6 taget sammen med nitrogenatomet og carbonatomet til hvilket de respektivt er bundet danner en pyrrolidinylring kondenseret til ring A.
9. Forbindelsen ifølge krav 1, hvor forbindelsen er valgt fra en hvilken som helst af
eller et farmaceutisk acceptabelt salt ifølge et hvilket som helst af de foregående; eller forbindelsen ifølge krav 1, vist med strukturformlen:
eller et farmaceutisk acceptabelt salt deraf.
10. Farmaceutisk sammensætning omfattende en farmaceutisk acceptabel bærer eller fortyndingsmiddel og en forbindelse ifølge et hvilket som helst af kravene 1-9.
11. Forbindelsen ifølge et hvilket som helst af kravene 1-9 eller et farmaceutisk acceptabelt salt deraf til anvendelse i behandling eller forebyggelse af en infektion eller kolonisering i et individ.
12. Anvendelse af en forbindelse ifølge et hvilket som helst af kravene 1-9 eller et farmaceutisk acceptabelt salt deraf i fremstillingen af et medikament til behandling eller forebyggelse af en infektion eller kolonisering i et individ.
13. Forbindelsen til anvendelse ifølge krav 11, eller anvendelse ifølge krav 12, hvor infektionen er forårsaget af: a) en organisme der vokser intracellulært som del af dens infektionsproces; eller b) gram-positiv organisme, såsom en gram-positiv organisme valgt fra klassen Bacilli, phylum Actinobacteria, og klasse Clostridia; eller c) gram-negativ organisme, såsom en gram-negativ organisme valgt fra gruppen bestående af Enterobactericeae, Bacteroidetes, Vibrionaceae, Pasteurellaceae, Pseudomonadaceae, Neisseriaceae, Rickettsiae, Moraxellaceae hvilke som helst arter af Proteeae, Acinetobacter spp., Helicobacter spp., og Campylobacter spp.
14. Anvendelsen eller forbindelse til anvendelse ifølge krav 13, hvor infektionen er forårsaget af: a) Bacilli-organisme valgt fra Staphylococcus spp., Streptococcus spp., Enterococcus spp., Bacillus spp., og Listeria spp.; eller b) Actinobacteria-organisme valgt fra Propionibacterium spp., Corynebacterium spp., Nocardia spp., og Actinobacteria spp.1, eller c) Clostridia-organisme valgt fra Clostridium spp.
15. Forbindelsen til anvendelse ifølge krav 11, eller anvendelse ifølge krav 12, hvor infektionen er forårsaget af an organisme valgt fra ordenen Rickettsiales og ordenen Chlamydiales, eller af en organisme valgt fra phylum Chlamydiae og phylum Spriochaetales; eventuelt hvor phylum Spriochaetales-organismen er fra en organisme valgt fra Borrelia spp. og Treponema spp.
16. Forbindelsen til anvendelse ifølge krav 11, eller anvendelse ifølge krav 12, hvor infektionen er forårsaget af en organisme valgt fra klassen Mollicutes, såsom en Mollicutes organisme valgt fra Mycoplasma spp.; eventuelt hvor Mycoplasma spp. er Mycoplasma pneumonia.
17. Forbindelsen til anvendelse ifølge krav 11, eller anvendelse ifølge krav 12, hvor infektionen er forårsaget af en organisme valgt fra Legionella spp. og Mycobacterium spp., såsom en Mycobacterium spp organisme valgt fra Mycobacterium tuberculosis.
18. Forbindelsen til anvendelse ifølge krav 11, eller anvendelse ifølge krav 12, hvor infektionen er forårsaget af: a) mere end én organisme; eller b) en organisme der er resistent over for ét eller flere antibiotika; eller c) en organisme der er resistent over for tetracyclin eller en hvilken som helst første og anden generation af tetracyclinantibiotika; eller d) en organisme der er resistent over for methicillin eller et hvilket som helst antibiotina i β-lactamklassen, herunder anden-, tredje- og fjerde-generationscephalosporiner; eller e) en organisme der er der er resistent over for en quinolon eller fluorquinolon; eller f) en organisme der er resistent over for tigecyclin; eller g) en organisme der er resistent over for tetracyclin; eller h) en organisme der er resistent over for methicillin; eller i) en organisme der er resistent over for vancomycin; eller j) en organisme der er resistent over for et antimikrobielt peptid eller en biosimilær terapeutisk behandling.
19. Anvendelsen eller forbindelse til anvendelse ifølge krav 13, hvor den grampositive organisme er valgt fra S. aureus, CoNS, S. pneumoniae, S. pyogenes, S. agalactiae, E. faecalis og E. faecium; eventuelt hvor den gram-negative organisme er valgt fra H. influenza, M. catarrbalis og Legionella pneumophila.
20. Forbindelsen ifølge et hvilket som helst af kravene 1-9 eller et farmaceutisk acceptabelt salt deraf eller den farmaceutiske sammensætning ifølge krav 10 til anvendelse i behandling eller forebyggelse afen respiratorisk infektion hos et individ; eventuelt hvor den respiratoriske infektion er samfundserhvervet bakteriel pneumoni (CABP), såsom en respiratorisk infektion forårsaget af en bakterie valgt fra S. aureus, S. pneumoniae, S. pyogenes, H. influenza, M. catarrhalis og Legionella pneumophila; eller forbindelsen ifølge et hvilket som helst af kravene 1-9 eller et farmaceutisk acceptabelt salt deraf eller den farmaceutiske sammensætning ifølge krav 10 til anvendelse i behandling eller forebyggelse af en hudinfektion hos et individ; eventuelt hvor hudinfektionen er en akut bakteriel hud- og hudstruktur-infektion (ABSSSI), såsom en hudinfektion forårsaget af en bakterie valgt fra S. aureus, CoNS, S. pyogenes, S. agalactiae, E faecalis og E. faecium.
21. Anvendelse af en forbindelse ifølge et hvilket som helst af kravene 1-9 eller et farmaceutisk acceptabelt salt deraf eller farmaceutisk sammensætning ifølge krav 10 i fremstillingen af et medikament til behandling eller forebyggelse af en respiratorisk infektion hos et individ; eventuelt hvor den respiratoriske infektion er samfundserhvervet bakteriel pneumoni (CABP), såsom en respiratorisk infektion forårsaget af en bakterie valgt fra S. aureus, S. pneumoniae, S. pyogenes, H. influenza, M. catarrhalis og Legionella pneumophila·, eller anvendelse af en forbindelse ifølge et hvilket som helst af kravene 1-9 eller et farmaceutisk acceptabelt salt deraf eller farmaceutisk sammensætning ifølge krav 10 i fremstillingen af et medikament til behandling eller forebyggelse af en hudinfektion hos et individ; eventuelt hvor hudinfektionen er en akut bakteriel hud- og hudstruktur-infektion (ABSSSI), såsom en hudinfektion forårsaget afen bakterie valgt fra S. aureus, CoNS, S. pyogenes, S. agalactiae, E. faecalis og E. faecium.
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