DK2590647T3 - Pro-neurogene forbindelser - Google Patents

Pro-neurogene forbindelser Download PDF

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DK2590647T3
DK2590647T3 DK11804335.5T DK11804335T DK2590647T3 DK 2590647 T3 DK2590647 T3 DK 2590647T3 DK 11804335 T DK11804335 T DK 11804335T DK 2590647 T3 DK2590647 T3 DK 2590647T3
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alkyl
carbazol
dibromo
independently selected
propan
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DK11804335.5T
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Steven L Mcknight
Andrew A Pieper
Joseph M Ready
Brabander Jef K De
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Univ Texas
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Priority claimed from US12/832,056 external-priority patent/US8362277B2/en
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    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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Claims (15)

1. Forbindelse med formel (I), eller et farmaceutisk acceptabelt salt deraf, til anvendelse ved behandling af fysisk vægttab, som er fortrinsvis associeret med en eller flere af normal aldring, kemoterapi, stråleterapi, stress, stofmisbrug, anoreksi, kakeksi, diabetes, demens, slagtilfælde, cancer og infektion:
O) hvor: hver af R1, R2 og R4 er hydrogen; R3 er udvalgt blandt hydrogen, halo, hydroxyl, sulfhydryl, CrC6-alkoxy, Cr Ce-thioalkoxy, CrC6-haloalkoxy, CrC6-thiohaloalkoxy, CrC6-alkyl, CrC6-ha-loalkyl, C2-C6-alkynyl, cyclopropyl, -N3, cyano, -NH2, -NH(CrC6-alkyl), -N(Cr C6-alkyl)2,-NHC(0)(CrC6-alkyl) og nitro; R og R' sammen med C2 og C3, respektivt, danner en kondenseret phenyl-ring med formel (II):
(ii) hvor hver af R5, R7 og R8 er hydrogen; R6 er udvalgt blandt hydrogen, halo, hydroxyl, sulfhydryl, CrC6-alkoxy, Cr Ce-thioalkoxy, CrC6-haloalkoxy, CrC6-thiohaloalkoxy, CrC6-alkyl, CrC6-ha- loalkyl, C2-C6-alkynyl, cyclopropyl, -N3, cyano, -NH2, -NH(CrC6-alkyl), -N(Cr C6-alkyl)2, -NHC(0)(Ci-C6-alkyl) og nitro; L1 er: en ligekædet CrC3-alkylen; L2 er: en ligekædet CrC3-alkylen; A er: CRA1RA2, hvor en af RA1 og RA2 er udvalgt blandt hydrogen, halo, CrC3-alkyl, og OR9; og den anden af RA1 og RA2 er udvalgt blandt halo, CrC3-alkyl og OR9; Z er: (i) -NR10R11; eller (iii) -OR12; eller (iv) -S(0)nR13, hvor n er 0, 1 eller 2; R9 er hydrogen eller CrC3-alkyl, som er eventuelt substitueret med hydroxyl eller CrC3-alkoxy; hver af R10 og R11 er uafhængigt udvalgt blandt substituenterne anført kollektivt i (a) til (f) nedenfor: (a) hydrogen; (b) Ce-C-io-aryl, som er eventuelt substitueret med fra 1-4 Rb; (c) heteroaryl indeholdende fra 5-14 ringatomer, hvor fra 1-6 af ringatomerne er uafhængigt udvalgt blandt N, NH, N(CrC3-alkyl), O og S; og hvor hetero-arylen er eventuelt substitueret med fra 1-4 Rb; (d) CrC6-alkyl eller CrC6-haloalkyl, hvoraf hver er eventuelt substitueret med fra 1-3 Rd; (e) -C(0)(CrC6-alkyl), -C(0)(CrC6-haloalkyl) eller -C(0)0(CrC6-alkyl); og (f) C2-C6-alkenyl eller C2-C6-alkynyl; hvor en af R10 og R11 er (b) eller (c); R12 er: (i) Ce-C-io-aryl, som er eventuelt substitueret med fra 1-4 Rb; eller (ii) heteroaryl indeholdende fra 5-14 ringatomer, hvor fra 1-6 af ringatomerne er uafhængigt udvalgt blandt N, NH, N(CrC3-alkyl), O og S; og hvor hetero-arylen er eventuelt substitueret med fra 1-4 Rb; R13 er: (i) Ce-C-io-aryl, som er eventuelt substitueret med fra 1-4 Rb; eller (ii) heteroaryl indeholdende fra 5-14 ringatomer, hvor fra 1-6 af ringatomerne er uafhængigt udvalgt blandt N, NH, N(CrC3-alkyl), O og S; og hvor hetero-arylen er eventuelt substitueret med fra 1-4 Rb; Ra ved hver forekomst er uafhængigt udvalgt blandt halo, hydroxyl, CrC6-alkoxy, CrC6-thioalkoxy, C-|-C6-haloalkoxy, CrC6-thiohaloalkoxy, oxo, thioxo, =NH, =N(CrC6-alkyl), CrC6-alkyl, CrC6-haloalkyl, -NH2, -NH(CrC6-alkyl), -N(CrC6-alkyl)2, -NHC(0)(CrC6-alkyl) og cyano; Rb ved hver forekomst er uafhængigt udvalgt blandt substituenterne anført i (aa) til (dd) nedenfor: (aa) CrC6-alkoxy; CrC6-haloalkoxy; CrC6-thioalkoxy; Ci-C6-thiohaloalkoxy; -0-(CH2)1.3-[0(CH2)1.3]1.3-H; Ci-C6-alkyl, CrC6-haloalkyl, -NH(Ci-C6-alkyl), -N(CrC6-alkyl)2, -NHC(0)(CrC6-alkyl), hvor alkyldelen af hver er eventuelt substitueret med fra 1-3 uafhængigt udvalgte Re; (bb) halo; hydroxyl; cyano; nitro; -NH2; azido; sulfhydryl; C2-C6 alkenyl; C2-C6-alkynyl; -C(0)H; -C(0)(CrC6-alkyl); -C(0)(CrC6-haloalkyl); -C(0)0H; -C(0)0(CrC6-alkyl); -C(0)NH2; -C(0)NH(CrC6-alkyl); -C(0)N(CrC6-alkyl)2; -S02(CrC6-alkyl); -S02NH2; -S02NH(CrC6-alkyl); -S02N(CrC6-alkyl)2; (cc) C3-C6-cycloalkyl eller heterocyclyl indeholdende fra 5-6 ringatomer, hvor fra 1-2 af ringatomerne af heterocyclylen er uafhængigt udvalgt blandt N, NH, N(CrC6-alkyl), NC(0)(Ci-C6-alkyl), O og S; og hvor hver af cycloalkylen og heterocyclylen er eventuelt substitueret med fra 1-3 uafhængigt udvalgte Ra; og (dd) phenyl eller heteroaryl indeholdende fra 5-6 ringatomer, hvor fra 1-2 af ringatomerne af heteroarylen er uafhængigt udvalgt blandt N, NH, N(CrC3-alkyl), O og S; hvor hver af nævnte phenyl og heteroaryl er eventuelt substitueret med fra 1-3 substituenter uafhængigt udvalgt blandt halo; hydroxyl; cyano; nitro; -NH2; -NH(Ci-C6-alkyl), -N(Ci-C6-alkyl)2, -NHC(0)(CrC6-alkyl), C-i-Ce-alkoxy; CrC6-haloalkoxy; CrC6-thioalkoxy; CrC6-thiohaloalkoxy; Cr Ce-alkyl og Ci-C6-haloalkyl; Rd ved hver forekomst er uafhængigt udvalgt blandt hydroxyl, CrC6-alkoxy, C-i-Ce-thioalkoxy, CrC6-haloalkoxy, CrC6-thiohaloalkoxy, CrC6-alkyl, CrC6-haloalkyl, -NH2, -NH(CrC6-alkyl), -N^-Ce-alkylfe, -NHC(0)(CrC6-alkyl) og cyano;og Re ved hver forekomst er uafhængigt udvalgt blandt hydroxyl, CrC6-alkoxy; C-i-Ce-thioalkoxy; CrC6-haloalkoxy; CrC6-thiohaloalkoxy; -NH2; -NH(CrC6- alkyl); -N(CrC6-alkyl)2; -NHC(0)(CrC6-alkyl); cyano; -C(0)H; -C(0)(CrC6-alkyl); -C(0)(CrC6-haloalkyl); -C(0)0H; -C(0)0(CrC6-alkyl); -C(0)NH2; -C(0)NH(C1-C6-alkyl);-C(0)N(C1-C6-alkyl)2; -802(0!-C6-alkyl); -S02NH2; -S02NH(CrC6-alkyl); -S02N(C-i-C6-alkyl)2; og L3-(CrC6-alkylen)-Cy, hvor L3 er en -O-, -NH-, -NCH3-, -C(0)-, -C(0)NH-, -C(0)NCH3-, -NHC(O)- eller -NCH3C(0)-, og Cy er et mættet, delvist umættet eller aromatisk carbocyklisk eller heterocyklisk ringsystem; forudsat at R3 og R6 ikke begge kan være hydrogen, når A er CH(CH3), R og R' er defineret i henhold til definition (1), Z er NR10R11, R10 er CH3, og R11 er usubstitueret phenyl.
2. Forbindelse til anvendelse ifølge krav 1, hvor A er CRA1RA2; hvor fortrinsvis en af RA1 og RA2 er halo, og den anden af RA1 og RA2 er hydrogen, halo eller CrC3-alkyl; hvor fortrinsvis en af RA1 og RA2 er fluor, og den anden af RA1 og RA2 er hydrogen eller fluor; hvor fortrinsvis en af RA1 og RA2 er OR9; og den anden af RA1 og RA2 er Cr C3-alkyl; eller hvor fortrinsvis en af RA1 og RA2 er OH; og den anden af RA1 og R^ er CH3.
3. Forbindelse til anvendelse ifølge krav 1 eller 2, hvor carbon bundet til RA1 og RA2 er substitueret med fire forskellige substitu-enter; hvor fortrinsvis carbon bundet til RA1 og RA2 er (F?)-konfigureret; hvor fortrinsvis carbon bundet til RA1 og RA2 er (S)-konfigureret; hvor fortrinsvis formel (l)-forbindelsen er (+) (dextrorotatorisk); eller hvor fortrinsvis formel (l)-forbindelsen er (-) (levororotatorisk).
4. Forbindelse til anvendelse ifølge krav 1, hvor R3 er udvalgt blandt halo, hydroxyl, sulfhydryl, CrC6-alkoxy, C-i-C6-thioalkoxy, CrC6-haloalkoxy, CrC6-thiohaloalkoxy, CrC6-alkyl, CrC6-halo-alkyl, C2-C6-alkynyl, cyclopropyl, -N3, cyano, -NH2, -NH(CrC6-alkyl), -N(Cr C6-alkyl)2,-NHC(0)(CrC6-alkyl) og nitro; hvor fortrinsvis R3 er halo og mere fortrinsvis brom; hvor fortrinsvis hver af R1, R2 og R4 er hydrogen.
5. Forbindelse til anvendelse ifølge krav 1, hvor R og R' sammen med C2 og C3, respektivt, danner en kondenseret phenylring med formel (II):
(II) hvor fortrinsvis R6 er udvalgt blandt halo, hydroxyl, sulfhydryl, CrC6-alkoxy, CrC6-thioalkoxy, CrC6-haloalkoxy, CrC6-thiohaloalkoxy, CrC6-alkyl, C-|-C6-haloalkyl, C2-C6-alkynyl, cyclopropyl, -N3, cyano, -NH2, -NH(CrC6-alkyl), -N(CrC6-alkyl)2, -NHC(0)(CrC6-alkyl) og nitro; hvor fortrinsvis R6 er halo eller CrC6-alkyl; hvor fortrinsvis hver af R5, R7 og R8 er hydrogen.
6. Forbindelse til anvendelse ifølge krav 1, hvor R og R' sammen med C2 og C3, respektivt, danner en kondenseret heteroarylring indeholdende fra 5-6 ringatomer, hvor fra 1-2 af ringatomerne er uafhængigt udvalgt blandt N, NH, N(CrC3-alkyl), O, og S; og hvor heteroarylringen er eventuelt substitueret med fra 1-3 uafhængigt udvalgte Rb
7. Forbindelse til anvendelse ifølge krav 1, hvor Z er -NR10R11.
8. Forbindelse til anvendelse ifølge krav 1, hvor Z er -NR10R11, hvor en af R10 og R11 er: (b) Ce-C-io-aryl, som er eventuelt substitueret med fra 1-4 Rb; eller (c) heteroaryl indeholdende fra 5-14 ringatomer, hvor fra 1-6 af ringatomerne er uafhængigt udvalgt blandt N, NH, N(CrC3-alkyl), O, og S; og hvor hetero-arylen er eventuelt substitueret med fra 1-4 Rb; og den anden af R10 og R11 er hydrogen eller CrC6-alkyl.
9. Forbindelse til anvendelse ifølge krav 1, hvor A er CHOH og Z er NR10R11, og hvor eventuelt en eller flere af følgende gælder: hver af R3 og R6 er uafhængigt CH3, brom eller chlor; hvor fortrinsvis en af R3 og R6 er CH3 og den anden af R3 og R6 er brom; hvor fortrinsvis R6 er CH3 og R3 er brom; hver af R10 og R11 er andet end hydrogen; hver af R10 og R11 er hydrogen; en af R10 og R11 er heteroaryl; L1 og/eller L2 er C2-C3 eventuelt substitueret alkylen; og/eller hver af R10 og R11 kan ikke være eventuelt substitueret naphthyl.
10. Forbindelse udvalgt blandt: 3.6- dibrom-9-(2-fluor-3-phenoxypropyl)-9H-carbazol; 1- (3,6-dibrom-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)-2-methylpropan- 2- ol; 1-(2,8-dimethyl-3,4-dihydro-1 H-pyrido[4,3-b]indol-5(2H)-yl)-3-(3-methoxyphenylamino)propan-2-ol; 1-(4-azidophenylamino)-3-(3,6-dibrom-9H-carbazol-9-yl)propan-2-ol; 1-(3-azido-6-brom-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol; 1 -(3,6-dibrom-9H-carbazol-9-yl)-3-(4-methoxyphenoxy) propan-2-ol; 1-(3,6-dichlor-9H-carbazol-9-yl)-3-(phenylsulfonyl)propan-2-ol; 3.6- dibrom-9-(2-fluor-3-(phenylsulfonyl)propyl)-9H-carbazol; (S)-1-(3,6-dibrom-9H-carbazol-9-yl)-3-(phenylsulfonyl) propan-2-ol; (R)-1-(3,6-dibrom-9H-carbazol-9-yl)-3-(phenylsulfonyl) propan-2-ol; 1-(3,6-dicyclopropyl-9H-carbazol-9-yl)-3-(phenylamino) propan-2-ol; 1-(3,6-diiodo-9H-carbazol-9-yl)-3-(phenylamino)propan-2-ol; 1-(3,6-diethynyl-9H-carbazol-9-yl)-3-(3-methoxyphenylamino) propan-2-ol; 9-(2-hydroxy-3-(3-methoxyphenylamino)propyl)-9H-carbazol-3,6-dicarbonitril; N-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropyl)anilin; 3.6- dibrom-9-(2,2-difluor-3-phenoxypropyl)-9H-carbazol; N-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropyl)-4-methoxyanilin; N-(2-brom-3-(3,6-dibrom-9H-carbazol-9-yl)propyl)-N-(4-methoxyphenyl)-4-nitrobenzensulfonamid; Ethyl2-(4-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropylamino)phenoxy)- acetat; N-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropyl)-4-(2-(2-methoxyethoxy)ethoxy)anilin; og N-(2-(2-(4-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropylamino)phenoxy)-acetamido)ethyl)-5-(2-oxohexahydro-1 H-thieno [3,4-d]imidazol-4-yl)pentan-amid; eller et farmaceutisk acceptabelt salt deraf.
11. Farmaceutisk sammensætning omfattende en forbindelse eller et salt ifølge krav 10 og en farmaceutisk acceptabel bærer.
12. Forbindelse eller salt ifølge krav 10, til anvendelse ved fremmelse af post-natal pattedyrsneurogenese og/eller reducering af neuronal celledød hos et individ med behov herfor, og fortrinsvis ved behandling af en sygdom, lidelse, forstyrrelse eller tilstand forårsaget af uønsket neuronal celledød eller associeret med utilstrækkelig neurogenese hos et individ med behov herfor.
13. Forbindelse eller salt ifølge krav 12, hvor individet har en sygdom eller tilstand udvalgt fra gruppen bestående af: skizofreni, større depression, bipolar lidelse, normal aldring, epilepsi, traumatisk hjerneskade, post-traumatisk stresslidelse, Parkinsons sygdom, Alzheimers sygdom, Downs syndrom, spinocerebellar ataksi, amyotrofisk lateral sklerose, Fluntingtons sygdom, slagtilfælde, strålebehandling, kronisk stress, misbrug af et neuroaktivt lægemiddel, retinal degenerering, rygmarvsskade, perifer nerveskade, fysiologisk vægttab og kognitivt tilbagefald associeret med normal aldring, og kemoterapi.
14. Forbindelse eller salt ifølge krav 12, hvor den post-natale pattedyrsnero-genese omfatter hippocampal og/eller hypothalamisk neurogenese, og hvor den neuronale celledød omfatter hippocampal og/eller hypothalamisk neuronal celledød.
15. Forbindelse til anvendelse ifølge krav 1, udvalgt blandt: FM-(3,6-dibrom-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)-propan-2-ol; S-1-(3,6-dibrom-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)-propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(2-iminopyridin-1 (2FI)-yl)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(phenylthio)propan-2-ol; N-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3- methoxyphenyl)acetamid; N-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropyl)-3-methoxyanilin; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)-propan-2-on; N-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-methoxypropyl)-3-methoxyanilin; 1-(3,6-dimethyl-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol; 1-(3-brom-6-methyl-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)-propan-2- ol; 1-(3,6-dichlor-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol; 1-(3-azidophenylamino)-3-(3,6-dibrom-9H-carbazol-9-yl)propan-2-ol; 3- (3,6-dibrom-9H-carbazol-9-yl)-2-hydroxy-N-(3-methoxyphenyl)-propan-amid; 4- (3,6-dibrom-9H-carbazol-9-yl)-1-(phenylamino)butan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-4-(phenylamino)butan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(pyridin-2-ylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-((3-methoxyphenyl)(methyl)-amino)propan-2-ol; 3-(3,6-dibrom-9H-carbazol-9-yl)-1 -(3-methoxyphenylamino)-1 -(methylthio)propan-2-on; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(pyrimidin-2-ylamino)propan-2-ol; N-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropyl)-3-methoxy-N-methylanilin; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(3-ethoxyphenylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(phenylsulfinyl)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(phenylsulfonyl)propan-2-ol; 1-(3-brom-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol; N-(5-(3-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropylamino)phenoxy)- pentyl)-2-(7-(dimethylamino)-2-oxo-2H-chromen-4-yl)acetamid; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-phenoxypropan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(pyridin-3-ylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(pyridin-4-ylamino)propan-2-ol; N-(3-(3,6-dibrom-9H-carbazol-9-yl)-2,2-difluorpropyl)-3-methoxyanilin; 1 -(3,6-dibrom-9H-carbazol-9-yl)-3-phenoxypropan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(phenylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(o-tolylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(m-tolylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(2-methoxyphenylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(naphthalen-1-ylamino)propan-2-ol; 1-(4-bromphenylamino)-3-(3,6-dichlor-9H-carbazol-9-yl)propan-2-ol; 1-(4-bromphenylamino)-3-(3,6-dibrom-9H-carbazol-9-yl)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(4-ethoxyphenylamino)propan-2-ol; 1-(4-chlorphenylamino)-3-(3,6-dibrom-9H-carbazol-9-yl)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(2,4-dimethoxyphenylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(2,3-dimethylphenylamino)propan-2-ol; 1-(2-chlorphenylamino)-3-(3,6-dibrom-9H-carbazol-9-yl)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(4-methoxyphenylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(m-tolylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(3,5-dimethylphenylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(3,4-dimethylphenylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(3,4-dimethylphenylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(2,5-dimethylphenylamino)propan-2-ol; 1-(9H-carbazol-9-yl)-3-(phenylamino)propan-2-ol; 1-(3,6-dichlor-9H-carbazol-9-yl)-3-(phenylamino)propan-2-ol; 1-(9H-carbazol-9-yl)-3-(p-tolylamino)propan-2-ol; 1-(3,6-dichlor-9H-carbazol-9-yl)-3-(p-tolylamino)propan-2-ol; N-(4-(3-(9H-carbazol-9-yl)-2-hydroxypropoxy)phenyl)acetamid; 1 -(9H-carbazol-9-yl)-3-phenoxypropan-2-ol; 1-(9H-carbazol-9-yl)-3-(4-methoxyphenylamino)propan-2-ol; methyl 4-(3-(9H-carbazol-9-yl)-2-hydroxypropoxy)benzoat; 1 -(9H-carbazol-9-yl)-3-(4-methoxyphenoxy)propan-2-ol; (S)-1-(3,6-dibrom-9H-carbazol-9-yl)-3-phenoxypropan-2-ol; (R) -1-(3,6-dibrom-9H-carbazol-9-yl)-3-phenoxypropan-2-ol; 3.6- dibrom-9-(2-fluor-3-phenoxypropyl)-9H-carbazol; 1- (3,6-dibrom-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)-2-methylpropan- 2- ol; 1-(4-azidophenylamino)-3-(3,6-dibrom-9H-carbazol-9-yl)propan-2-ol; 1-(3-azido-6-brom-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol; 1 -(3,6-dibrom-9H-carbazol-9-yl)-3-(4-methoxyphenoxy) propan-2-ol; 1-(3,6-dichlor-9H-carbazol-9-yl)-3-(phenylsulfonyl)propan-2-ol; 3.6- dibrom-9-(2-fluor-3-(phenylsulfonyl)propyl)-9H-carbazol; (S) -1-(3,6-dibrom-9H-carbazol-9-yl)-3-(phenylsulfonyl) propan-2-ol; (R)-1-(3,6-dibrom-9H-carbazol-9-yl)-3-(phenylsulfonyl) propan-2-ol; 1-(3,6-dicyclopropyl-9H-carbazol-9-yl)-3-(phenylamino) propan-2-ol; 1-(3,6-diiodo-9H-carbazol-9-yl)-3-(phenylamino)propan-2-ol; 1- (3,6-diethynyl-9H-carbazol-9-yl)-3-(3-methoxyphenylamino) propan-2-ol; 9-(2-hydroxy-3-(3-methoxyphenylamino)propyl)-9H-carbazol-3,6-dicarbonitril; N-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropyl)anilin; 3.6- dibrom-9-(2,2-difluor-3-phenoxypropyl)-9H-carbazol; N-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropyl)-4-methoxyanilin; N-(2-brom-3-(3,6-dibrom-9H-carbazol-9-yl)propyl)-N-(4-methoxyphenyl)-4-nitrobenzensulfonamid; Ethyl 2-(4-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropylamino)phenoxy)ace-tat; N-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropyl)-4-(2-(2- methoxyethoxy)ethoxy)anilin; N-(2-(2-(4-(3-(3,6-dibrom-9H-carbazol-9-yl)-2- fluorpropylamino)phenoxy)acetamido)ethyl)-5-(2-oxohexahydro-1 H-thieno [3,4-d]imidazol-4-yl)pentanamid; 2- (4-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropylamino)phenoxy)-N,N-dimethylacetamid; 2- (4-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropylamino)phenoxy)-N-(2-hydroxyethyl)acetamid; 1-(3,6-bis(trifluormethyl)-9/-/-carbazol-9-yl)-3-(phenylamino)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(3-methoxyphenylthio)propan-2-ol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(4-methoxyphenylthio)propan-2-ol; 3.6- dibrom-9-(2-fluor-3-(3-methoxyphenylthio)propyl)-9H-carbazol; 3.6- dibrom-9-(2-fluor-3-(4-methoxyphenylthio)propyl)-9H-carbazol; 3.6- dibrom-9-(2-fluor-3-(3-methoxyphenylsulfonyl)propyl)-9H-carbazol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(3-methoxyphenylsulfonyl)propan-2-ol; 3.6- dibrom-9-(2-fluor-3-(4-methoxyphenylsulfonyl)propyl)-9H-carbazol; 1-(3,6-dibrom-9H-carbazol-9-yl)-3-(4-methoxyphenylsulfonyl)propan-2-ol; 3- (3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropylthio)phenol; 4- (3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropylthio)phenol; 3- (3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropylsulfonyl)phenol; 4- (3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropylsulfonyl)phenol; 1-(3-aminophenylthio)-3-(3,6-dibrom-9H-carbazol-9-yl)propan-2-ol; 1-(4-aminophenylthio)-3-(3,6-dibrom-9H-carbazol-9-yl)propan-2-ol; 1-(3,6-dibrom-9/-/-carbazol-9-yl)-3-phenoxypropan-2-amin; A/-benzyl-2-(3-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropylthio)- phenoxy)acetamid; A/-benzyl-2-(4-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropylthio)- phenoxy)acetamid; 3- (3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropylsulfonyl)phenol; /V-benzyl-2-(3-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropylsulfonyl)-phenoxy)acetamid; 4- (3-(3,6-dibrom-9H-carbazol-9-yl)-2-fluorpropylsulfonyl)phenol; 5- (5-(3-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropylamino)phenoxy)-pentylcarbamoyl)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoesyre; (9-(2-hydroxy-3-(phenylthio)propyl)-9/-/-carbazol-3,6-dicarbonitril; 9-(2-hydroxy-3-phenoxypropyl)-9/-/-carbazol-3,6-dicarbonitril; Æ-N-(3-(3,6-dibrom-9/-/-carbazol-9-yl)-2-fluorpropyl)-3-methoxyanilin; S-N-(3-(3,6-dibrom-9/-/-carbazol-9-yl)-2-fluorpropyl)-3-methoxyanilin; 2-(6-amino-3-imino-3H-xanthen-9-yl)-4-(6-(5-(3-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropylamino)phenoxy)pentylamino)-6-oxohexylcarbamoyl)-benzoesyre; 2-(6-amino-3-imino-3H-xanthen-9-yl)-5-(6-(5-(3-(3-(3,6-dibrom-9H-carbazol-9-yl)-2-hydroxypropylamino)phenoxy)pentylamino)-6-oxohexylcarbamoyl)-benzoesyre; og 1-(3-(3,6-dibrom-9/-/-carbazol-9-yl)-2-hydroxypropyl)pyridin-2(1 /-/)-on; eller et farmaceutisk acceptabelt salt deraf.
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