DK2566847T3 - Hidtil ukendt immunmodulator og antiinflammatoriske forbindelser - Google Patents

Hidtil ukendt immunmodulator og antiinflammatoriske forbindelser Download PDF

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DK2566847T3
DK2566847T3 DK11738472.7T DK11738472T DK2566847T3 DK 2566847 T3 DK2566847 T3 DK 2566847T3 DK 11738472 T DK11738472 T DK 11738472T DK 2566847 T3 DK2566847 T3 DK 2566847T3
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ylcarbamoyl
benzoic acid
chloro
difluorobiphenyl
difluoro
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DK11738472.7T
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English (en)
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Meyyappan Muthuppalaniappan
Prashnant Kashinath Bhavar
Srikant Viswanadha
Swaroop Kumar V S Vakkalanka
Gayatri Swaroop Merikapudi
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Icozen Therapeutics Pvt Ltd
Rhizen Pharmaceuticals S A
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
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    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
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Claims (15)

1. Forbindelse med formlen (I)
(I) eller en tautomer, stereoisomer (såsom en enantiomer eller diastereomer), et farmaceutisk acceptabelt salt eller en N-oxid deraf, hvor Ring A er uafhængigt udvalgt fra en substitueret eller ikke-substitueret monocyklisk aryl og en substitueret eller ikke-substitueret monocyklisk heteroaryl, hvor hver forekomst af X uafhængigt er CR4 eller N; Ring B er uafhængigt udvalgt fra
Rer hydrogen; R1 er-COOH,-; L1 mangler; L2 mangler eller er -OCRaRb-; Cy er udvalgt fra substitueret eller ikke-substitueret cycloalkyl, substitueret eller ikke-substitueret heterocyklisk gruppe, substitueret eller ikke-substitueret aryl og substitueret eller ikke-substitueret heteroaryl; R4 er uafhængigt udvalgt fra hydrogen, hydroxy, halogen, cyano, -ORa, -S(=O)q-Ra,-NRaRb, -C(=Y)-Ra, -C(=Y)-ORa, -C(=Y)-NRaRb,-S(=O)q-NRaRb, substitueret eller ikke-
substitueret alkyl, substitueret eller ikke-substitueret alkenyl, substitueret eller ikke-substitueret alkynyl, substitueret eller ikke-substitueret cycloalkyl, substitueret eller ikke-substitueret cycloalkylakyl, substitueret eller ikke-substitueret cycloalkenyl, eller hvor to R4-substituenter, når de er til stede, kan være forbundet, så de danner en substitueret eller ikke-substitueret mættet eller umættet 3-10-leddet ring, som eventuelt kan indbefatte heteroatomer, der kan være de samme eller forskellige og er udvalgt fra O, NRa eller S, eller alternativt hvor to R4 substituenter, når de er orto i forhold til hinanden på en aromatisk ring, kan være forbundet, så de danner en substitueret eller ikke-substitueret mættet eller umættet 4-10-leddet ring, som eventuelt kan indbefatte et eller flere heteroatomer, der kan være de samme eller forskellige og er udvalgt fra O, NRa eller S; hver forekomst af Ra og Rb kan være den samme eller forskellige og er uafhængigt udvalgt fra hydrogen, halogen, hydroxy, cyano, substitueret eller ikke-substitueret Ci_ 6aIkyl, -ORC, hvor Rc er substitueret eller ikke-substitueret Ci_6alkyl) eller Ra og Rb, når de er direkte bundet til et fælles atom, kan være forbundet, så de danner en oxo-gruppe (=0) eller danner en substitueret eller ikke-substitueret mættet eller umættet 3-10-leddet ring, som eventuelt kan indbefatte heteroatomer, der kan være de samme eller forskellige og er udvalgt fra O, NRa eller S; hver forekomst af Y er O.
2. Forbindelse ifølge krav 1, hvor ring A er udvalgt fra
hvor Ri og R4 er som defineret i krav 1.
3. Forbindelse ifølge krav 1, hvor hver forekomst af X er CH, C-CI, C-F eller N.
4. Forbindelse ifølge krav 1 hvor ring A inklusive X er udvalgt fra
hvor Ri og R4 er som defineret i krav 1; Ring B er udvalgt fra
L2 mangler eller er -O-CRaRb-.; hvor hver forekomst af Ra og Rb kan være de samme eller forskellige og er uafhængigt udvalgt fra hydrogen eller substitueret eller ikke-substitueret Ci_6alkyl; Cy er uafhængigt udvalgt fra substitueret eller ikke-substitueret cycloalkyl, substitueret eller ikke-substitueret heterocyklisk gruppe, substitueret eller ikke-substitueret aryl og substitueret eller ikke-substitueret heteroaryl.
5. Forbindelse ifølge krav 1 udvalgt fra 2-(3,5-Difluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2- (3'-Ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 3- (3,5-Difluor-3'-methoxybiphenyl-4-ylcarbamoyl)pyrazin-2-carboxylsyre 3-(3,5-Difluor-3'-ethoxybiphenyl-4-ylcarbamoyl)pyrazin-2-carboxylsyre 2- (2'-Chlor-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 3- [3'-(Benzyloxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]pyrazin-2-carboxylsyre 2- (3,5-Difluorbiphenyl-4-ylcarbamoyl)benzoesyre 3- (3-Chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)pyrazin-2-carboxylsyre
2-[3,5-Difluor-3'-(trifluormethoxy)biphenyl-4-ylcarbamoyl]benzoesyre 2-[3'-(Benzyloxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 4.5- Dichlor-2-(3-chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(3,5-difluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Dichlor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-5-fluor-3'-propoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-2',5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Dichlor-3'-ethoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[2'-Fluor-3-(trifluormethoxy)biphenyl-4-ylcarbamoyl] benzoesyre 2-(3,5-Dichlor-2'-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Difluor-3'-isopropoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Difluor-3'-propoxybiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(2',3-dichlor-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4,5-Dichlor-2-(2',3-dichlor-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(2',3-dichlor-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(2'-chlor-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-5-fluor-3'-isobutoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3,5-Trifluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3,5-Trichlorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Difluor-3'-isobutoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-Butoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)-6-fluorbenzoesyre 2-[3-Chlor-5-fluor-3'-(trifluormethoxy)biphenyl-4-ylcarbamoyl] benzoesyre 2-[4-(Benzyloxy)-2,6-difluorphenylcarbamoyl]benzoesyre 2-[3'-(Cyclopentyloxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-(3-Chlor-3'-(cyclopentyloxy)-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-[3'-(Difluormethoxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-[3-Chlor-3'-(difluormethoxy)-5-fluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-(2'-Chlor-3,5-difluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,3',5-Trifluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[4-(Benzo[d][l,3]dioxol-5-yl)-2,6-difluorphenylcarbamoyl]benzoesyre 2-[4-(Benzo[d][l,3]dioxol-5-yl)-2-chlor-6-fluorphenylcarbamoyl]benzoesyre 2-(3,5-Difluor-3',4'-dimethoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,3',5-Trifluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,3'-Dichlor-5-fluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[4-(2,3-Dihydrobenzofuran-5-yl)-2,6-difluorphenylcarbamoyl]benzoesyre 2-[2-Chlor-4-(2,3-dihydrobenzofuran-5-yl)-6-fluorphenylcarbamoyl]benzoesyre 2-[4-(l,3-Dimethyl-lH-indazol-5-yl)-2,6-difluorphenylcarbamoyl]benzoesyre 2-(3'-Chlor-3,5-difluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-5-fluor-3',4'-dimethoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3-Dichlor-5-fluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3,5-Trifluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(4'-Chlor-3,5-difluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(33,4'-Dichlor-5-fluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-chlor-2',5-difluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,4',5-trifluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[2,6-difluor-4-(3-methyl-lH-indol-5-yl)phenylcarbamoyl]benzoesyre 2-[2,6-difluor-4-(3-methyl-lH-indazol-5-yl)phenylcarbamoyl]benzoesyre 2-(3-chlor-3'-ethyl-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-chlor-3'-ethoxy-2',5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-[2-chlor-4-(2,3-dihydrobenzo[b][l,4]dioxin-6-yl)-6-fluorphenylcarbamoyl] benzoesyre 2-[3-chlor-5-fluor-3'-(2,2,2-trifluorethoxy)biphenyl-4-ylcarbamoyl]benzoesyre 2-[3'-(ethylthio)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-[3'-(ethylsulfinyl)-3,5-difluorbiphenyl-4-ylcarbamoyl] benzoesyre 2-(3'-cyclopropoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)-6(5)-methylbenzoesyre 2-[4-(3-ethyl-lH-indol-5-yl)-2,6-difluorphenylcarbamoyl] benzoesyre 2-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)nicotinsyre 4-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)nicotinsyre 2-[3,5-difluor-3'-(2,2,2-trifluorethoxy)biphenyl-4-ylcarbamoyl]benzoesyre 2-(3'-ethyl-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-[3,5-difluor-3'-(trifluormethoxy)biphenyl-4-ylcarbamoyl]benzoesyre 2-[2,6-Difluor-4-(3-propyl-lH-indol-5-yl)phenylcarbamoyl] benzoesyre 2-[2-Chlor-4-(3-ethyl-lH-indol-5-yl)-6-fluorphenylcarbamoyl]benzoesyre og farmaceutisk acceptable salte deraf.
6. Forbindelse med formlen (IA)
eller en tautomer, stereoisomer (såsom en enantiomer eller diastereomer), et farmaceutisk acceptabelt salt eller en N-oxid deraf, hvor Ring A inklusive R1 er udvalgt fra
Ring B er udvalgt fra
I_2 mangler eller er O-CH2-; og Cy er substitueret eller ikke-substitueret phenyl, indol eller indazol.
7. Forbindelse ifølge et hvilket som helst af de foregående krav, hvor Cy er
8. Forbindelse ifølge krav 6 udvalgt fra 2-(3,5-Difluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Difluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzensulfonsyre 2- (3'-Ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 3- (3,5-Difluor-3'-methoxybiphenyl-4-ylcarbamoyl)pyrazin-2-carboxylsyre 3-(3,5-Difluor-3'-ethoxybiphenyl-4-ylcarbamoyl)pyrazin-2-carboxylsyre 2-(2'-Chlor-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre
3-[3'-(Benzyloxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]pyrazin-2-carboxylsyre 2- (3,5-Difluorbiphenyl-4-ylcarbamoyl)benzoesyre 3- (3-Chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)pyrazin-2-carboxylsyre 2-[3,5-Difluor-3'-(trifluormethoxy)biphenyl-4-ylcarbamoyl]benzoesyre 2-[3'-(Benzyloxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 4.5- Dichlor-2-(3-chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(3,5-difluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Dichlor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-5-fluor-3'-propoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-2',5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Dichlor-3'-ethoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Dichlor-2'-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Difluor-3'-isopropoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Difluor-3'-propoxybiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(2',3-dichlor-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4,5-Dichlor-2-(2',3-dichlor-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(2',3-dichlor-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(2'-chlor-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-5-fluor-3'-isobutoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3,5-Trifluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3,5-Trichlorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Difluor-3'-isobutoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-Butoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre N-(3-Chlor-3'-ethoxy-5-fluorbiphenyl-4-yl)-2-(hydroxymethyl)benzamid N-(3'-Ethoxy-3,5-difluorbiphenyl-4-yl)-2-(hydroxymethyl)benzamid 2-(3-Chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)-6-fluorbenzoesyre 2-[3-Chlor-5-fluor-3'-(trifluormethoxy)biphenyl-4-ylcarbamoyl] benzoesyre 2-[4-(Benzyloxy)-2,6-difluorphenylcarbamoyl]benzoesyre 2-[3'-(Cyclopentyloxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-(3-Chlor-3'-(cyclopentyloxy)-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-[3'-(Difluormethoxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-[3-Chlor-3'-(difluormethoxy)-5-fluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-(2'-Chlor-3,5-difluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,3',5-Trifluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[4-(Benzo[d][l,3]dioxol-5-yl)-2,6-difluorphenylcarbamoyl]benzoesyre 2-[4-(Benzo[d][l,3]dioxol-5-yl)-2-chlor-6-fluorphenylcarbamoyl]benzoesyre 2-(3,5-Difluor-3',4'-dimethoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,3',5-Trifluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,3'-Dichlor-5-fluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[4-(2,3-Dihydrobenzofuran-5-yl)-2,6-difluorphenylcarbamoyl]benzoesyre 2-[2-Chlor-4-(2,3-dihydrobenzofuran-5-yl)-6-fluorphenylcarbamoyl]benzoesyre 2-[4-(l,3-Dimethyl-lH-indazol-5-yl)-2,6-difluorphenylcarbamoyl]benzoesyre 2-(3'-Chlor-3,5-difluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-5-fluor-3',4'-dimethoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3-Dichlor-5-fluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3,5-Trifluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(4'-Chlor-3,5-difluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(33,4'-Dichlor-5-fluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-chlor-2',5-difluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,4',5-trifluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[2,6-difluor-4-(3-methyl-lH-indol-5-yl)phenylcarbamoyl]benzoesyre 2-[2,6-difluor-4-(3-methyl-lH-indazol-5-yl)phenylcarbamoyl]benzoesyre 2-(3-chlor-3'-ethyl-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-chlor-3'-ethoxy-2',5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-[2-chlor-4-(2,3-dihydrobenzo[b][l,4]dioxin-6-yl)-6-fluorphenylcarbamoyl] benzoesyre 2-[3-chlor-5-fluor-3'-(2,2,2-trifluorethoxy)biphenyl-4-ylcarbamoyl]benzoesyre 2-[3'-(ethylthio)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-[3'-(ethylsulfinyl)-3,5-difluorbiphenyl-4-ylcarbamoyl] benzoesyre 2-(3'-cyclopropoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)-6(5)-methylbenzoesyre 2-[4-(3-ethyl-lH-indol-5-yl)-2,6-difluorphenylcarbamoyl] benzoesyre 2-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)nicotinsyre 4-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)nicotinsyre 2-[3,5-difluor-3'-(2,2,2-trifluorethoxy)biphenyl-4-ylcarbamoyl] benzoesyre 2-(3'-ethyl-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-[3,5-difluor-3'-(trifluormethoxy)biphenyl-4-ylcarbamoyl]benzoesyre 2-[2,6-Difluor-4-(3-propyl-lH-indol-5-yl)phenylcarbamoyl]benzoesyre 2-[2-Chlor-4-(3-ethyl-lH-indol-5-yl)-6-fluorphenylcarbamoyl] benzoesyre og farmaceutisk acceptable salte deraf.
9. Forbindelse udvalgt fra 2-(3,5-Difluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Difluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzensulfonsyre 2-(6-(3-Methoxyphenyl)pyridin-3-ylcarbamoyl)benzoesyre 2-(3'-Ethoxy-3-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2- (3'-Ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 3- (3,5-Difluor-3'-methoxybiphenyl-4-ylcarbamoyl)pyrazin-2-carboxylsyre 3-(3,5-Difluor-3'-ethoxybiphenyl-4-ylcarbamoyl)pyrazin-2-carboxylsyre 2- (2'-Chlor-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 3- [3'-(Benzyloxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]pyrazin-2-carboxylsyre 2- (3,5-Difluorbiphenyl-4-ylcarbamoyl)benzoesyre 3- (3-Chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)pyrazin-2-carboxylsyre 2-[3,5-Difluor-3'-(trifluormethoxy)biphenyl-4-ylcarbamoyl]benzoesyre 2-[3'-(Benzyloxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 4.5- Dichlor-2-(3-chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(3,5-difluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Dichlor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-5-fluor-3'-propoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-2',5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Dichlor-3'-ethoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[3-Fluor-3'-(trifluormethoxy)biphenyl-4-ylcarbamoyl] benzoesyre 2-[2'-Fluor-3-(trifluormethoxy)biphenyl-4-ylcarbamoyl] benzoesyre 2-(3,5-Dichlor-2'-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Difluor-3'-isopropoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Difluor-3'-propoxybiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(2',3-dichlor-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4,5-Dichlor-2-(2',3-dichlor-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(2',3-dichlor-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 4.5- Dichlor-2-(2'-chlor-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-5-fluor-3'-isobutoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3,5-Trifluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3,5-Trichlorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,5-Difluor-3'-isobutoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-Butoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre N-(3-Chlor-3'-ethoxy-5-fluorbiphenyl-4-yl)-2-(hydroxymethyl)benzamid N-(3'-Ethoxy-3,5-difluorbiphenyl-4-yl)-2-(hydroxymethyl)benzamid 2-(3-Chlor-3'-ethoxy-5-fluorbiphenyl-4-ylcarbamoyl)-6-fluorbenzoesyre 2-[3-Chlor-5-fluor-3'-(trifluormethoxy)biphenyl-4-ylcarbamoyl] benzoesyre 2-[4-(Benzyloxy)-2,6-difluorphenylcarbamoyl]benzoesyre 2-[3'-(Cyclopentyloxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-(3-Chlor-3'-(cyclopentyloxy)-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-[3'-(Difluormethoxy)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-[3-Chlor-3'-(difluormethoxy)-5-fluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-(2'-Chlor-3,5-difluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,3',5-Trifluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[4-(Benzo[d][l,3]dioxol-5-yl)-2,6-difluorphenylcarbamoyl]benzoesyre 2-[4-(Benzo[d][l,3]dioxol-5-yl)-2-chlor-6-fluorphenylcarbamoyl]benzoesyre 2-(3,5-Difluor-3',4'-dimethoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,3',5-Trifluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,3'-Dichlor-5-fluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[4-(2,3-Dihydrobenzofuran-5-yl)-2,6-difluorphenylcarbamoyl]benzoesyre 2-[2-Chlor-4-(2,3-dihydrobenzofuran-5-yl)-6-fluorphenylcarbamoyl]benzoesyre 2-[4-(l,3-Dimethyl-lH-indazol-5-yl)-2,6-difluorphenylcarbamoyl]benzoesyre 2-(3'-Chlor-3,5-difluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-Chlor-5-fluor-3',4'-dimethoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3-Dichlor-5-fluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(2',3,5-Trifluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(4'-Chlor-3,5-difluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(33,4'-Dichlor-5-fluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-chlor-2',5-difluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3,4',5-trifluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[2,6-difluor-4-(3-methyl-lH-indol-5-yl)phenylcarbamoyl]benzoesyre 2-[2,6-difluor-4-(3-methyl-lH-indazol-5-yl)phenylcarbamoyl]benzoesyre 2-(3-chlor-3'-ethyl-5-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-chlor-3'-ethoxy-2',5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-[2-chlor-4-(2,3-dihydrobenzo[b][l,4]dioxin-6-yl)-6-fluorphenylcarbamoyl] benzoesyre 2-[3-chlor-5-fluor-3'-(2,2,2-trifluorethoxy)biphenyl-4-ylcarbamoyl]benzoesyre 2-(3-fluor-3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-ethoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[3'-(ethylthio)-3,5-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-[3'-(ethylsulfinyl)-3,5-difluorbiphenyl-4-ylcarbamoyl] benzoesyre 2-(3'-cyclopropoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)-6(5)-methylbenzoesyre 2-[4-(3-ethyl-lH-indol-5-yl)-2,6-difluorphenylcarbamoyl] benzoesyre 2-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)nicotinsyre 4-(3'-ethoxy-3,5-difluorbiphenyl-4-ylcarbamoyl)nicotinsyre 2-[3'-(ethylthio)-2,3,5,6-tetrafluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-(2'-chlor-2-fluor-5'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3-fluor-3'-propoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-propoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[3'-(ethylthio)-2-fluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-[3,5-difluor-3'-(2,2,2-trifluorethoxy)biphenyl-4-ylcarbamoyl] benzoesyre 2-(3'-ethyl-3,5-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(2'-chlorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-methoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-[3'-(trifluormethoxy)biphenyl-4-ylcarbamoyl]benzoesyre 2-[3'-(ethylthio)-2,6-difluorbiphenyl-4-ylcarbamoyl]benzoesyre 2-(3'-ethylbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-butoxy-2,3,5,6-tetrafluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-butoxy-3-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-[3,5-difluor-3'-(trifluormethoxy)biphenyl-4-ylcarbamoyl]benzoesyre 2-(3'-cyclopropoxy-3-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-cyclopropoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-butoxybiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-butoxy-2-fluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-(3'-Butoxy-2,6-difluorbiphenyl-4-ylcarbamoyl)benzoesyre 2-[2,6-Difluor-4-(3-propyl-lH-indol-5-yl)phenylcarbamoyl]benzoesyre 2-[2-Chlor-4-(3-ethyl-lH-indol-5-yl)-6-fluorphenylcarbamoyl] benzoesyre og farmaceutisk acceptable salte deraf.
10. Farmaceutisk sammensætning omfattende en forbindelse ifølge et hvilket som helst af kravene 1-9 og en farmaceutisk acceptabel bærer.
11. Farmaceutisk sammensætning ifølge krav 10, der endvidere omfatter en eller flere yderligere terapeutiske midler udvalgt fra anti-inflammatorisk middel, immunsupprimerende og/eller immunmodulerende midler, steroider, ikke-steroide anti-inflammatoriske midler, antihistaminer, analgetika og egnede blandinger deraf.
12. Forbindelse ifølge et hvilket som helst af kravene 1-9 til anvendelse til behandling af en sygdom, forstyrrelse eller tilstand, der ville have fordel af hæmning af enten dihydrooratatdehydrogenase (DHODH) eller IL 17 cytokin eller dem begge.
13. Forbindelse ifølge et hvilket som helst af kravene 1-9 til anvendelse til behandling af autoimmune sygdomme, immun- og inflammationssygdomme, destruktive knogleforstyrrelser, forskellige cancersygdomme og maligne neoplastiske sygdomme, angiogeneserelaterede forstyrrelser, virussygdomme eller infektionssygdomme via hæmning af DHODH eller IL17, eller en kombination deraf.
14. Forbindelse ifølge et hvilket som helst af kravene 1-9 til anvendelse til behandling af rheumatoid arthritis, arthritis psoriatica, systemisk lupus erythematosus, multipel sklerose, psoriasis, ankyloserende spondylitis, Wegeners granulomatose, polyartikulær juvenil idiopatisk arthritis, inflammatorisk tarmsygdom, Crohns sygdom, Reiters syndrom, fibromyalgi, kronisk pancreatitis, graft-versus-host-sygdom, kronisk sarcoidose, transplantatafstødning, kontaktdermatitis, atopisk dermatitis, allergisk rhinitis, allergisk konjunktivitis, Beh^ets syndrom, inflammatoriske øjentilstande såsom konjunktivitis, uveitis, osteoporose, osteoarthritis, hæmangiomer, okulær neovaskularisering, maculadegeneration, HIV-infektion, hepatitis og cytomegalovirusinfektion, sepsis, septisk shock, endotoksisk shock, Gram-negativ sepsis, toksisk shocksyndrom, Shigellose og andre protozo-infestationer såsom malaria, kronisk obstruktiv lungesygdom, astma, colitis, ulcerativ colitis, arthritis, knoglesygdomme, der er associeret med forhøjet knogleresorption, eller kronisk obstruktiv luftvejssygdom, Feltys syndrom, sarcoidose, Stills sygdom, pemfigoid, Takayasu-arteritis, systemisk sklerose, recidiverende polychondritis, refraktær IgA-nefropati, SAPHO2-syndrom (SAS), cytomegalovirusinfektion inklusive rhinitis eller cyste.
15. Forbindelse ifølge et hvilket som helst af kravene 1-9 til anvendelse til behandling af rheumatoid arthritis, multipel sklerose eller inflammatorisk tarmsygdom.
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AU2011249546A1 (en) 2012-12-20
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