SI3018132T1 - Kondenzirani derivati imidazola, uporabni kot IDO inhibitorji - Google Patents
Kondenzirani derivati imidazola, uporabni kot IDO inhibitorji Download PDFInfo
- Publication number
- SI3018132T1 SI3018132T1 SI201231193T SI201231193T SI3018132T1 SI 3018132 T1 SI3018132 T1 SI 3018132T1 SI 201231193 T SI201231193 T SI 201231193T SI 201231193 T SI201231193 T SI 201231193T SI 3018132 T1 SI3018132 T1 SI 3018132T1
- Authority
- SI
- Slovenia
- Prior art keywords
- imidazo
- isoindol
- ethyl
- hydroxy
- ethanol
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title claims abstract 3
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims 2
- 150000002460 imidazoles Chemical class 0.000 title 1
- 102000006639 indoleamine 2,3-dioxygenase Human genes 0.000 claims abstract 8
- 108020004201 indoleamine 2,3-dioxygenase Proteins 0.000 claims abstract 8
- 206010062016 Immunosuppression Diseases 0.000 claims abstract 4
- 206010028980 Neoplasm Diseases 0.000 claims abstract 4
- 230000001506 immunosuppresive effect Effects 0.000 claims abstract 4
- 201000011510 cancer Diseases 0.000 claims abstract 3
- 230000001404 mediated effect Effects 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- -1 2-Bromostyryl Chemical group 0.000 claims 141
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 82
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 55
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 36
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 20
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 20
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical group 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- YGACXVRLDHEXKY-LHPNLFKDSA-N 4-[(1r)-2-[(5s)-6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl]-1-hydroxyethyl]cyclohexan-1-ol Chemical compound C1([C@@H](C[C@@H]2N3C=NC=C3C3=C2C(=CC=C3)F)O)CCC(O)CC1 YGACXVRLDHEXKY-LHPNLFKDSA-N 0.000 claims 6
- YGACXVRLDHEXKY-VDPJLGHJSA-N 4-[(1s)-2-[(5s)-6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl]-1-hydroxyethyl]cyclohexan-1-ol Chemical compound C1([C@H](C[C@@H]2N3C=NC=C3C3=C2C(=CC=C3)F)O)CCC(O)CC1 YGACXVRLDHEXKY-VDPJLGHJSA-N 0.000 claims 6
- GGPLEOHHSWNDKN-UHFFFAOYSA-N n-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]cyclohexyl]benzamide Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCC1NC(=O)C1=CC=CC=C1 GGPLEOHHSWNDKN-UHFFFAOYSA-N 0.000 claims 6
- YEBWNEBTTYUFMD-LADGPHEKSA-N 1-[4-[(1r)-1-hydroxy-2-[(5s)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]piperidin-1-yl]-2-phenylethanone Chemical compound C1CC([C@@H](C[C@@H]2N3C=NC=C3C3=CC=CC=C32)O)CCN1C(=O)CC1=CC=CC=C1 YEBWNEBTTYUFMD-LADGPHEKSA-N 0.000 claims 5
- SCWXAHFBXGCWHC-UHFFFAOYSA-N 2-(6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)-1-(4-phenylmethoxycyclohexyl)ethanol Chemical compound C1=CC=C(F)C2=C1C1=CN=CN1C2CC(O)C(CC1)CCC1OCC1=CC=CC=C1 SCWXAHFBXGCWHC-UHFFFAOYSA-N 0.000 claims 5
- YGACXVRLDHEXKY-LHLWNEDTSA-N 4-[(1s)-2-[(5r)-6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl]-1-hydroxyethyl]cyclohexan-1-ol Chemical compound C1([C@H](C[C@H]2N3C=NC=C3C3=C2C(=CC=C3)F)O)CCC(O)CC1 YGACXVRLDHEXKY-LHLWNEDTSA-N 0.000 claims 5
- YGACXVRLDHEXKY-UHFFFAOYSA-N 4-[2-(6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)-1-hydroxyethyl]cyclohexan-1-ol Chemical compound C1=CC=C(F)C2=C1C1=CN=CN1C2CC(O)C1CCC(O)CC1 YGACXVRLDHEXKY-UHFFFAOYSA-N 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims 5
- YTRRAUACYORZLX-WMZOPIPTSA-N (1s)-1-cyclohexyl-2-[(5s)-5h-imidazo[5,1-a]isoindol-5-yl]ethanol Chemical compound C1([C@H](C[C@@H]2N3C=NC=C3C3=CC=CC=C32)O)CCCCC1 YTRRAUACYORZLX-WMZOPIPTSA-N 0.000 claims 4
- TZLKQKCGJBWURI-UHFFFAOYSA-N 1-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 TZLKQKCGJBWURI-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- YTRRAUACYORZLX-SJLPKXTDSA-N (1r)-1-cyclohexyl-2-[(5r)-5h-imidazo[5,1-a]isoindol-5-yl]ethanol Chemical compound C1([C@@H](C[C@H]2N3C=NC=C3C3=CC=CC=C32)O)CCCCC1 YTRRAUACYORZLX-SJLPKXTDSA-N 0.000 claims 3
- YTRRAUACYORZLX-DAFXYXGESA-N (1s)-1-cyclohexyl-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1([C@H](CC2N3C=NC=C3C3=CC=CC=C32)O)CCCCC1 YTRRAUACYORZLX-DAFXYXGESA-N 0.000 claims 3
- YTRRAUACYORZLX-AEFFLSMTSA-N (1s)-1-cyclohexyl-2-[(5r)-5h-imidazo[5,1-a]isoindol-5-yl]ethanol Chemical compound C1([C@H](C[C@H]2N3C=NC=C3C3=CC=CC=C32)O)CCCCC1 YTRRAUACYORZLX-AEFFLSMTSA-N 0.000 claims 3
- KVZKINKUBBROSQ-ICXLUZGWSA-N (2s)-2-amino-1-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-3-phenylpropan-1-one Chemical compound C([C@H](N)C(=O)N1CCC(CC1)C(O)CC1N2C=NC=C2C2=CC=CC=C21)C1=CC=CC=C1 KVZKINKUBBROSQ-ICXLUZGWSA-N 0.000 claims 3
- JYHYESPWJNAVOK-YBEGLDIGSA-N (2z)-1-cyclohexyl-2-imidazo[1,5-b]isoindol-5-ylideneethanol Chemical compound C/12=CC=CC=C2C2=CN=CN2C\1=C/C(O)C1CCCCC1 JYHYESPWJNAVOK-YBEGLDIGSA-N 0.000 claims 3
- FRFMOJJXJLFIDQ-UHFFFAOYSA-N (3-fluoro-2-hydroxyphenyl)-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]methanone Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1C(=O)C1=CC=CC(F)=C1O FRFMOJJXJLFIDQ-UHFFFAOYSA-N 0.000 claims 3
- SBGDHJQZWJCENG-UHFFFAOYSA-N (4-fluorophenyl)-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]methanone Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1C(=O)C1=CC=C(F)C=C1 SBGDHJQZWJCENG-UHFFFAOYSA-N 0.000 claims 3
- RRQRZNAPWJNCHH-MBIQTGHCSA-N (5s)-5-(2-cyclohexyl-2-hydroxyethyl)-5h-imidazo[5,1-a]isoindol-6-ol Chemical compound C([C@@H]1N2C=NC=C2C2=C1C(=CC=C2)O)C(O)C1CCCCC1 RRQRZNAPWJNCHH-MBIQTGHCSA-N 0.000 claims 3
- PPEUMDWFICZDCN-SILNSSARSA-N (nz)-n-[1-cyclohexyl-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethylidene]hydroxylamine Chemical compound C12=CC=CC=C2C2=CN=CN2C1C/C(=N/O)C1CCCCC1 PPEUMDWFICZDCN-SILNSSARSA-N 0.000 claims 3
- APZFWCOFDKAMPQ-UHFFFAOYSA-N 1-(1,4-dioxaspiro[4.5]decan-8-yl)-2-(6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1=CC=C(F)C2=C1C1=CN=CN1C2CC(O)C(CC1)CCC21OCCO2 APZFWCOFDKAMPQ-UHFFFAOYSA-N 0.000 claims 3
- QJJZDVYBJWAXFJ-UHFFFAOYSA-N 1-(1-benzylsulfonylpiperidin-4-yl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1S(=O)(=O)CC1=CC=CC=C1 QJJZDVYBJWAXFJ-UHFFFAOYSA-N 0.000 claims 3
- PESZLYAORBUEKU-UHFFFAOYSA-N 1-(2,4-dimethylfuran-3-yl)-2-(6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound CC1=COC(C)=C1C(O)CC1N2C=NC=C2C2=C1C(F)=CC=C2 PESZLYAORBUEKU-UHFFFAOYSA-N 0.000 claims 3
- BMDIVHVHCUXCED-UHFFFAOYSA-N 1-(2-aminophenyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanone Chemical compound NC1=CC=CC=C1C(=O)CC1N2C=NC=C2C2=CC=CC=C21 BMDIVHVHCUXCED-UHFFFAOYSA-N 0.000 claims 3
- TTXRSWJNADPSSS-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C1=CC=CC=C1Cl TTXRSWJNADPSSS-UHFFFAOYSA-N 0.000 claims 3
- FCJBROSAFICRIB-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanone Chemical compound ClC1=CC=CC=C1C(=O)CC1N2C=NC=C2C2=CC=CC=C21 FCJBROSAFICRIB-UHFFFAOYSA-N 0.000 claims 3
- AEXLPMGBOMVETQ-UHFFFAOYSA-N 1-(3-aminocyclohexyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1C(N)CCCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 AEXLPMGBOMVETQ-UHFFFAOYSA-N 0.000 claims 3
- XKHZICCQURTELE-UHFFFAOYSA-N 1-(3-aminophenyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound NC1=CC=CC(C(O)CC2N3C=NC=C3C3=CC=CC=C32)=C1 XKHZICCQURTELE-UHFFFAOYSA-N 0.000 claims 3
- VVIHJLDHSORWDP-UHFFFAOYSA-N 1-(3-chlorophenyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanone Chemical compound ClC1=CC=CC(C(=O)CC2N3C=NC=C3C3=CC=CC=C32)=C1 VVIHJLDHSORWDP-UHFFFAOYSA-N 0.000 claims 3
- BBYFCKZHLMMOBN-UHFFFAOYSA-N 1-(4,4-difluorocyclohexyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C1CCC(F)(F)CC1 BBYFCKZHLMMOBN-UHFFFAOYSA-N 0.000 claims 3
- FPKRCRNJVIHTNG-UHFFFAOYSA-N 1-(4,4-difluorocyclohexyl)-2-(6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1=CC=C(F)C2=C1C1=CN=CN1C2CC(O)C1CCC(F)(F)CC1 FPKRCRNJVIHTNG-UHFFFAOYSA-N 0.000 claims 3
- OWKPEYRNGTVBEN-UHFFFAOYSA-N 1-(4-aminocyclohexyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1CC(N)CCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 OWKPEYRNGTVBEN-UHFFFAOYSA-N 0.000 claims 3
- CCWQDYPXEQFDAH-UHFFFAOYSA-N 1-(4-aminophenyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1=CC(N)=CC=C1C(O)CC1N2C=NC=C2C2=CC=CC=C21 CCWQDYPXEQFDAH-UHFFFAOYSA-N 0.000 claims 3
- UDZRVINHNLAGCI-UHFFFAOYSA-N 1-(5H-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C=1N=CN2C1C1=CC=CC=C1C2C(C)O UDZRVINHNLAGCI-UHFFFAOYSA-N 0.000 claims 3
- JNNMYZDYWKIDMJ-UHFFFAOYSA-N 1-(5h-imidazo[5,1-a]isoindol-5-yl)-2-methylpropan-2-ol Chemical compound C1=CC=C2C3=CN=CN3C(CC(C)(O)C)C2=C1 JNNMYZDYWKIDMJ-UHFFFAOYSA-N 0.000 claims 3
- SXBYEDHYJLPXEQ-UHFFFAOYSA-N 1-(5h-imidazo[5,1-a]isoindol-5-yl)-3-methylbutan-2-ol Chemical compound C1=CC=C2C3=CN=CN3C(CC(O)C(C)C)C2=C1 SXBYEDHYJLPXEQ-UHFFFAOYSA-N 0.000 claims 3
- MRJBMWLOCDYCAN-UHFFFAOYSA-N 1-(cyclohexen-1-yl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C1=CCCCC1 MRJBMWLOCDYCAN-UHFFFAOYSA-N 0.000 claims 3
- XCPKPBVNKDRBNO-UHFFFAOYSA-N 1-[3-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]azetidin-1-yl]-2-phenylethanone Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(C1)CN1C(=O)CC1=CC=CC=C1 XCPKPBVNKDRBNO-UHFFFAOYSA-N 0.000 claims 3
- ORGKDAJDXPSGMH-UHFFFAOYSA-N 1-[4-(2-hydroxyethylidene)cyclohexyl]-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1CC(=CCO)CCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 ORGKDAJDXPSGMH-UHFFFAOYSA-N 0.000 claims 3
- ATEZPMBIQPSAPX-UHFFFAOYSA-N 1-[4-(aminomethyl)cyclohexyl]-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1CC(CN)CCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 ATEZPMBIQPSAPX-UHFFFAOYSA-N 0.000 claims 3
- SPKYNRBBSWXNES-JTHBVZDNSA-N 1-[4-[(1r)-1-hydroxy-2-[(5s)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]piperidin-1-yl]-2-(oxan-4-yl)ethanone Chemical compound C1CC([C@@H](C[C@@H]2N3C=NC=C3C3=CC=CC=C32)O)CCN1C(=O)CC1CCOCC1 SPKYNRBBSWXNES-JTHBVZDNSA-N 0.000 claims 3
- CFSKVFWSULUVNP-LADGPHEKSA-N 1-[4-[(1r)-1-hydroxy-2-[(5s)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]piperidin-1-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C1CC([C@@H](C[C@@H]2N3C=NC=C3C3=CC=CC=C32)O)CCN1C(=O)CC1=CC=C(C(F)(F)F)C=C1 CFSKVFWSULUVNP-LADGPHEKSA-N 0.000 claims 3
- YEBWNEBTTYUFMD-UPVQGACJSA-N 1-[4-[(1s)-1-hydroxy-2-[(5s)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]piperidin-1-yl]-2-phenylethanone Chemical compound C1CC([C@H](C[C@@H]2N3C=NC=C3C3=CC=CC=C32)O)CCN1C(=O)CC1=CC=CC=C1 YEBWNEBTTYUFMD-UPVQGACJSA-N 0.000 claims 3
- BHPMBGLATDMBIK-UHFFFAOYSA-N 1-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-2,2-dimethylpropan-1-one Chemical compound C1CN(C(=O)C(C)(C)C)CCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 BHPMBGLATDMBIK-UHFFFAOYSA-N 0.000 claims 3
- JTROHOGCUWMDID-UHFFFAOYSA-N 1-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-2-(2-methyl-1,3-thiazol-5-yl)ethanone Chemical compound S1C(C)=NC=C1CC(=O)N1CCC(C(O)CC2N3C=NC=C3C3=CC=CC=C32)CC1 JTROHOGCUWMDID-UHFFFAOYSA-N 0.000 claims 3
- GRTMSCAOJVEIAZ-UHFFFAOYSA-N 1-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-2-(3-hydroxyphenyl)ethanone Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1C(=O)CC1=CC=CC(O)=C1 GRTMSCAOJVEIAZ-UHFFFAOYSA-N 0.000 claims 3
- YEBWNEBTTYUFMD-UHFFFAOYSA-N 1-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-2-phenylethanone Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1C(=O)CC1=CC=CC=C1 YEBWNEBTTYUFMD-UHFFFAOYSA-N 0.000 claims 3
- ADXRHXZIAQWYPA-UHFFFAOYSA-N 1-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-2-pyridin-4-ylethanone Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1C(=O)CC1=CC=NC=C1 ADXRHXZIAQWYPA-UHFFFAOYSA-N 0.000 claims 3
- TXXNCTKTORUINM-UHFFFAOYSA-N 1-cyclohex-3-en-1-yl-2-(6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1=CC=C(F)C2=C1C1=CN=CN1C2CC(O)C1CCC=CC1 TXXNCTKTORUINM-UHFFFAOYSA-N 0.000 claims 3
- OCMQWRLTHDLIRS-UHFFFAOYSA-N 1-cyclohexyl-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanamine Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(N)C1CCCCC1 OCMQWRLTHDLIRS-UHFFFAOYSA-N 0.000 claims 3
- YTRRAUACYORZLX-UHFFFAOYSA-N 1-cyclohexyl-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C1CCCCC1 YTRRAUACYORZLX-UHFFFAOYSA-N 0.000 claims 3
- LXUFCLWCRAGUAS-UHFFFAOYSA-N 1-cyclohexyl-2-(5h-imidazo[5,1-a]isoindol-5-yl)propan-1-ol Chemical compound C12=CC=CC=C2C2=CN=CN2C1C(C)C(O)C1CCCCC1 LXUFCLWCRAGUAS-UHFFFAOYSA-N 0.000 claims 3
- AKOIXTSNUPHRQM-UHFFFAOYSA-N 1-cyclohexyl-2-(6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1=CC=C(F)C2=C1C1=CN=CN1C2CC(O)C1CCCCC1 AKOIXTSNUPHRQM-UHFFFAOYSA-N 0.000 claims 3
- IDAMUBBXWPKKDM-UHFFFAOYSA-N 1-cyclohexyl-2-(6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)ethanone Chemical compound C1=2C(F)=CC=CC=2C2=CN=CN2C1CC(=O)C1CCCCC1 IDAMUBBXWPKKDM-UHFFFAOYSA-N 0.000 claims 3
- GZLGDNBVPZDDHN-UHFFFAOYSA-N 1-cyclohexyl-2-(8-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C12=CC=C(F)C=C2C2=CN=CN2C1CC(O)C1CCCCC1 GZLGDNBVPZDDHN-UHFFFAOYSA-N 0.000 claims 3
- OSGALIUMFAKSAR-UHFFFAOYSA-N 1-cyclohexyl-2-(9-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C12=CC=CC(F)=C2C2=CN=CN2C1CC(O)C1CCCCC1 OSGALIUMFAKSAR-UHFFFAOYSA-N 0.000 claims 3
- IKPLNLUUWHVZPW-UHFFFAOYSA-N 1-cyclohexyl-2-(9-methoxy-5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound N12C=NC=C2C=2C(OC)=CC=CC=2C1CC(O)C1CCCCC1 IKPLNLUUWHVZPW-UHFFFAOYSA-N 0.000 claims 3
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- XKYDXVDTWDQCAV-JSOIOWGOSA-N [4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-[(2s)-pyrrolidin-2-yl]methanone Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1C(=O)[C@@H]1CCCN1 XKYDXVDTWDQCAV-JSOIOWGOSA-N 0.000 claims 3
- HIFKHTGNHWXMNH-UHFFFAOYSA-N [4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-thiophen-2-ylmethanone Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1C(=O)C1=CC=CS1 HIFKHTGNHWXMNH-UHFFFAOYSA-N 0.000 claims 3
- NTBNOWXFZMDXDZ-UHFFFAOYSA-N [4-[2-(6-fluoro-5H-imidazo[5,1-a]isoindol-5-yl)-1-hydroxyethyl]cyclohexyl] benzoate Chemical compound C1=CC=C(F)C2=C1C1=CN=CN1C2CC(O)C(CC1)CCC1OC(=O)C1=CC=CC=C1 NTBNOWXFZMDXDZ-UHFFFAOYSA-N 0.000 claims 3
- FDUHADIZUWTWAZ-UHFFFAOYSA-N cyclohexyl-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]methanone Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1C(=O)C1CCCCC1 FDUHADIZUWTWAZ-UHFFFAOYSA-N 0.000 claims 3
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- WRFXUJBZOJLWBB-UHFFFAOYSA-N ethyl 2-(5h-imidazo[5,1-a]isoindol-5-yl)acetate Chemical compound C1=CC=C2C3=CN=CN3C(CC(=O)OCC)C2=C1 WRFXUJBZOJLWBB-UHFFFAOYSA-N 0.000 claims 3
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- PJZVULFUQSLZMW-UHFFFAOYSA-N methyl 4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 PJZVULFUQSLZMW-UHFFFAOYSA-N 0.000 claims 3
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- MMUUOCZEFMSKGV-UHFFFAOYSA-N n-[2-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]cyclohexyl]acetamide Chemical compound CC(=O)NC1CCCCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 MMUUOCZEFMSKGV-UHFFFAOYSA-N 0.000 claims 3
- XGXIYSFXMYLWCL-UHFFFAOYSA-N n-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)C)CCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 XGXIYSFXMYLWCL-UHFFFAOYSA-N 0.000 claims 3
- IEHATHSCQGVOMX-UHFFFAOYSA-N n-[4-[2-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-2-oxoethyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CC(=O)N1CCC(C(O)CC2N3C=NC=C3C3=CC=CC=C32)CC1 IEHATHSCQGVOMX-UHFFFAOYSA-N 0.000 claims 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
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- QYRWUEOAQAHUBN-UYAOXDASSA-N tert-butyl 4-[(1r)-1-hydroxy-2-[(5r)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1[C@H](O)C[C@H]1N2C=NC=C2C2=CC=CC=C21 QYRWUEOAQAHUBN-UYAOXDASSA-N 0.000 claims 3
- QYRWUEOAQAHUBN-AZUAARDMSA-N tert-butyl 4-[(1r)-1-hydroxy-2-[(5s)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1[C@H](O)C[C@@H]1N2C=NC=C2C2=CC=CC=C21 QYRWUEOAQAHUBN-AZUAARDMSA-N 0.000 claims 3
- QYRWUEOAQAHUBN-QUCCMNQESA-N tert-butyl 4-[(1s)-1-hydroxy-2-[(5r)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1[C@@H](O)C[C@H]1N2C=NC=C2C2=CC=CC=C21 QYRWUEOAQAHUBN-QUCCMNQESA-N 0.000 claims 3
- QYRWUEOAQAHUBN-ICSRJNTNSA-N tert-butyl 4-[(1s)-1-hydroxy-2-[(5s)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1[C@@H](O)C[C@@H]1N2C=NC=C2C2=CC=CC=C21 QYRWUEOAQAHUBN-ICSRJNTNSA-N 0.000 claims 3
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- XSCIACOBOYKTCG-UHFFFAOYSA-N tert-butyl n-[2-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=C1C(O)CC1N2C=NC=C2C2=CC=CC=C21 XSCIACOBOYKTCG-UHFFFAOYSA-N 0.000 claims 3
- BLMRVWKNYYFJNH-UHFFFAOYSA-N tert-butyl n-[2-[2-(5h-imidazo[5,1-a]isoindol-5-yl)acetyl]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=C1C(=O)CC1N2C=NC=C2C2=CC=CC=C21 BLMRVWKNYYFJNH-UHFFFAOYSA-N 0.000 claims 3
- ZOYUNVHKXHQRTI-UHFFFAOYSA-N tert-butyl n-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C(O)CC1N2C=NC=C2C2=CC=CC=C21 ZOYUNVHKXHQRTI-UHFFFAOYSA-N 0.000 claims 3
- YTRRAUACYORZLX-FUHWJXTLSA-N (1r)-1-cyclohexyl-2-[(5s)-5h-imidazo[5,1-a]isoindol-5-yl]ethanol Chemical compound C1([C@@H](C[C@@H]2N3C=NC=C3C3=CC=CC=C32)O)CCCCC1 YTRRAUACYORZLX-FUHWJXTLSA-N 0.000 claims 2
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- QRYSBXVPYUPWPS-UHFFFAOYSA-N 1-(2-aminophenyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound NC1=CC=CC=C1C(O)CC1N2C=NC=C2C2=CC=CC=C21 QRYSBXVPYUPWPS-UHFFFAOYSA-N 0.000 claims 2
- KYSMLSSHZDKYMC-UHFFFAOYSA-N 1-(3-chlorophenyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C1=CC=CC(Cl)=C1 KYSMLSSHZDKYMC-UHFFFAOYSA-N 0.000 claims 2
- JDTLXYAWWCQLKO-UHFFFAOYSA-N 1-(4-aminophenyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanone Chemical compound C1=CC(N)=CC=C1C(=O)CC1N2C=NC=C2C2=CC=CC=C21 JDTLXYAWWCQLKO-UHFFFAOYSA-N 0.000 claims 2
- ISCDNERVCHFOSZ-UHFFFAOYSA-N 1-[1-(2-aminopyrimidin-4-yl)piperidin-4-yl]-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound NC1=NC=CC(N2CCC(CC2)C(O)CC2N3C=NC=C3C3=CC=CC=C32)=N1 ISCDNERVCHFOSZ-UHFFFAOYSA-N 0.000 claims 2
- ZBLUTUCNUZUDLC-UHFFFAOYSA-N 1-[1-(4-aminopyrimidin-2-yl)piperidin-4-yl]-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound NC1=CC=NC(N2CCC(CC2)C(O)CC2N3C=NC=C3C3=CC=CC=C32)=N1 ZBLUTUCNUZUDLC-UHFFFAOYSA-N 0.000 claims 2
- YEBWNEBTTYUFMD-ISKFKSNPSA-N 1-[4-[(1r)-1-hydroxy-2-[(5r)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]piperidin-1-yl]-2-phenylethanone Chemical compound C1CC([C@@H](C[C@H]2N3C=NC=C3C3=CC=CC=C32)O)CCN1C(=O)CC1=CC=CC=C1 YEBWNEBTTYUFMD-ISKFKSNPSA-N 0.000 claims 2
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- KNCOURWLVNPTET-UHFFFAOYSA-N 1-[4-[2-(6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)-1-hydroxyethyl]cyclohexyl]-3-phenylurea Chemical compound C1=CC=C(F)C2=C1C1=CN=CN1C2CC(O)C(CC1)CCC1NC(=O)NC1=CC=CC=C1 KNCOURWLVNPTET-UHFFFAOYSA-N 0.000 claims 2
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- QYPGWMMBPPVTDC-UHFFFAOYSA-N 1-cyclohexyl-3-(5h-imidazo[5,1-a]isoindol-5-yl)propan-1-ol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CCC(O)C1CCCCC1 QYPGWMMBPPVTDC-UHFFFAOYSA-N 0.000 claims 2
- RLXCXBWRZHJHBP-UHFFFAOYSA-N 2-(5h-imidazo[5,1-a]isoindol-5-yl)-1-(3-nitrophenyl)ethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C1=CC=CC([N+]([O-])=O)=C1 RLXCXBWRZHJHBP-UHFFFAOYSA-N 0.000 claims 2
- OHBRKNAYFFVLGG-UHFFFAOYSA-N 2-(5h-imidazo[5,1-a]isoindol-5-yl)-1-(oxan-3-yl)ethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C1CCCOC1 OHBRKNAYFFVLGG-UHFFFAOYSA-N 0.000 claims 2
- QSCNULJNJWIRQZ-UHFFFAOYSA-N 2-(5h-imidazo[5,1-a]isoindol-5-yl)-1-piperidin-3-ylethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C1CCCNC1 QSCNULJNJWIRQZ-UHFFFAOYSA-N 0.000 claims 2
- FNGDHPYZIOFVLB-UHFFFAOYSA-N 2-(5h-imidazo[5,1-a]isoindol-5-yl)-1-pyridin-2-ylethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C1=CC=CC=N1 FNGDHPYZIOFVLB-UHFFFAOYSA-N 0.000 claims 2
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- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 2
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- HVZJGGWTHITDQX-UHFFFAOYSA-N [1-cyclohexyl-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl] acetate Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(OC(=O)C)C1CCCCC1 HVZJGGWTHITDQX-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
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- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
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- HTQALUPYXXELOZ-UHFFFAOYSA-N n-cyclohexyl-n-hydroxy-4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidine-1-carboxamide Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1C(=O)N(O)C1CCCCC1 HTQALUPYXXELOZ-UHFFFAOYSA-N 0.000 claims 2
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- HMWJTYJOWMVDLR-UHFFFAOYSA-N tert-butyl n-[4-[2-(5h-imidazo[5,1-a]isoindol-5-yl)acetyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C(=O)CC1N2C=NC=C2C2=CC=CC=C21 HMWJTYJOWMVDLR-UHFFFAOYSA-N 0.000 claims 2
- OZPZBFLBHBJLPJ-UHFFFAOYSA-N 1-(5H-imidazo[5,1-a]isoindol-5-yl)propan-1-ol Chemical compound C=1N=CN2C=1C1=CC=CC=C1C2C(CC)O OZPZBFLBHBJLPJ-UHFFFAOYSA-N 0.000 claims 1
- PRUMALLZQVUWMP-UHFFFAOYSA-N 1-[4-(cyclopropylmethylidene)cyclohexyl]-2-(6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1=CC=C(F)C2=C1C1=CN=CN1C2CC(O)C(CC1)CCC1=CC1CC1 PRUMALLZQVUWMP-UHFFFAOYSA-N 0.000 claims 1
- BVPPFWQOSBAAQQ-UHFFFAOYSA-N 1-[4-(hydroxymethyl)cyclohexyl]-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound C1CC(CO)CCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 BVPPFWQOSBAAQQ-UHFFFAOYSA-N 0.000 claims 1
- YEBWNEBTTYUFMD-VWNXMTODSA-N 1-[4-[(1s)-1-hydroxy-2-[(5r)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]piperidin-1-yl]-2-phenylethanone Chemical compound C1CC([C@H](C[C@H]2N3C=NC=C3C3=CC=CC=C32)O)CCN1C(=O)CC1=CC=CC=C1 YEBWNEBTTYUFMD-VWNXMTODSA-N 0.000 claims 1
- RHYNNJXEEIIUOZ-UHFFFAOYSA-N 1-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-2-(4-methylsulfonylphenyl)ethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CC(=O)N1CCC(C(O)CC2N3C=NC=C3C3=CC=CC=C32)CC1 RHYNNJXEEIIUOZ-UHFFFAOYSA-N 0.000 claims 1
- MQBRBOPIMMPJSH-UHFFFAOYSA-N 1-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-3,3-dimethylbutan-1-one Chemical compound C1CN(C(=O)CC(C)(C)C)CCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 MQBRBOPIMMPJSH-UHFFFAOYSA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- XGPDPODYEGNQHX-UHFFFAOYSA-N 2-(5h-imidazo[5,1-a]isoindol-5-yl)-1-(1,3-thiazol-5-yl)ethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C1=CN=CS1 XGPDPODYEGNQHX-UHFFFAOYSA-N 0.000 claims 1
- SMPOUDVZNQHGAJ-UHFFFAOYSA-N 2-(5h-imidazo[5,1-a]isoindol-5-yl)-1-spiro[2.5]octan-6-ylethanol Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCC21CC2 SMPOUDVZNQHGAJ-UHFFFAOYSA-N 0.000 claims 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- CRPBNHZIHKRNAA-UNMCSNQZSA-N 4-[(1s)-1-hydroxy-2-[(5s)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]-n-(oxan-4-yl)piperidine-1-carboxamide Chemical compound C1CC([C@H](C[C@@H]2N3C=NC=C3C3=CC=CC=C32)O)CCN1C(=O)NC1CCOCC1 CRPBNHZIHKRNAA-UNMCSNQZSA-N 0.000 claims 1
- VISMIBIBEYHWCU-UHFFFAOYSA-N 4-[2-(6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl)-1-hydroxyethyl]-n-phenylcyclohexane-1-carboxamide Chemical compound C1=CC=C(F)C2=C1C1=CN=CN1C2CC(O)C(CC1)CCC1C(=O)NC1=CC=CC=C1 VISMIBIBEYHWCU-UHFFFAOYSA-N 0.000 claims 1
- LBQMOMOJHCUWOK-UHFFFAOYSA-N 4-[2-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-2-oxoethyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CC(=O)N1CCC(C(O)CC2N3C=NC=C3C3=CC=CC=C32)CC1 LBQMOMOJHCUWOK-UHFFFAOYSA-N 0.000 claims 1
- NSQXEQFBHZFTES-UHFFFAOYSA-N 4-[2-[4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidin-1-yl]-2-oxoethyl]benzoic acid Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1C(=O)CC1=CC=C(C(O)=O)C=C1 NSQXEQFBHZFTES-UHFFFAOYSA-N 0.000 claims 1
- DFYHDIYAMRTKAI-ZHACJKMWSA-N 5-[(e)-2-cyclohexylethenyl]-5h-imidazo[5,1-a]isoindole Chemical compound C1CCCCC1\C=C\C1N2C=NC=C2C2=CC=CC=C21 DFYHDIYAMRTKAI-ZHACJKMWSA-N 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 210000003679 cervix uteri Anatomy 0.000 claims 1
- RHJVIGLEIFVHIJ-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1[CH]CCCC1 RHJVIGLEIFVHIJ-UHFFFAOYSA-N 0.000 claims 1
- 208000037765 diseases and disorders Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000003128 head Anatomy 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- BNOFPRYSRGTLOU-UHFFFAOYSA-N n-cyclopropyl-4-[1-hydroxy-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethyl]piperidine-1-carboxamide Chemical compound C12=CC=CC=C2C2=CN=CN2C1CC(O)C(CC1)CCN1C(=O)NC1CC1 BNOFPRYSRGTLOU-UHFFFAOYSA-N 0.000 claims 1
- 210000003739 neck Anatomy 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 abstract 1
- 238000011394 anticancer treatment Methods 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
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Claims (14)
- KONDENZIRANI DERIVATI IMIDAZOLA, UPORABNI KOT IDO INHIBITORJI EP3018132 Patentni zahtevki1. Farmacevtski sestavek, obsegajoč spojino, ki je S2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; etil 2-(5H-imidazo[5,1 -a]izoindol-5-il)acetat; (E)-5-(2-bromostiril)-5H-imidazo[5,1 -ajizoindol; 2-(6-kloro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -cikloheksiletanol; 2-(6-kloro-5H-imidazo[5,1 -ajizoindol-5-il)-1 -cikloheksiletanon; 2-(5H-imidazo[5,1-a]izomdol-5-il)etil2-(((1R,2R,5S)-2-izopropil-5-metilcikloheksil)oksi)acetat; tert-butil (4-(2-(SH-imidazo[5,1 -a]izoindol-5-il)acetil)fenil)karbamat; 1 -(4-aminofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanon; tert-butil (4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)fenil)karbamat; 1 -(4-aminofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-l-(3-nitrofenil)etanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(3-nitrofenil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(2-nitrofenil)etanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(2-nitrofenil)etanol; tert-butil (2-(2-(5H-imidazo[5,1 -a]izoindol-5-il)acetil)fenil)karbamat; tert-butil (2-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)fenil)karbamat; 1 -(2-aminofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanon; 1- (2-aminofenil)-2-(5H-imidazo[5,1-ajizoindol-5-il)etanol; 1 -(2-klorofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanon; 1 -(5H-imidazo[5,1 -a]izoindol-5-il)-2-metilpropan-2-ol; 1 -(2-klorofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -(3-klorofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1-a]izoindol-5-il)-1-feniletanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -feniletanol; 1-(2,4-dimetilfuran-3-il)-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; 1-(3-klorofenil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanon; 1-cikloheksil-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanon; 1- cikloheksil-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1-a]izoindol-5-il)-1-(tetrahidro-2H-piran-4-il)etanol; 2-(7-kloro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -cikloheksiletanol; (Z)-1-cikloheksil-2-(5H-imidazo[5,1-a]izoindol-5-il)etanon oksim; 1 -ciklopentil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; tert-butil 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 - karboksilat; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanamin; tert-butil (3-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)fenil)karbamat; 1 -(3-aminofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 4- (2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-hidroksietil)cikloheksanol; 1 -cikloheksil-2-(9-methoxy-5H-imidazo[5,1 -a]izoindol-5-il)etanol; 5- (2-cikloheksil-2-hidroksietil)-5H-imidazo[5,1-a]izoindol-9-ol; 2-(8-kloro-5H-imidazo[5,1-a]izoindol-5-il)-1-cikloheksiletanol; 1 -(cikloheks-1 -en-1 -il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1- cikloheksil-2-(8-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; 2- (6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-(1,4-dioksaspiro[4.5]dekan-8-il)etanol; 4- (2-(6-ftuoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanone; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-metilencikloheksil)etanol; 1 -(cikloheks-3-en-1 -il)-2-(5H-imidazo [5,1 -a]izoindol-5-il)etanol; 1 -(4-(hidroksimetil)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; (4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)(thiophen-2-il)metanon; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)etanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-metilencikloheksil)etanol; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-metilcikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(tiazol-4-il)etanol; 2-(5H-imidazo[5,1 -ajizoindol-5-il)-1 -(tiazol-5-il)etanol; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2,2-dimetilpropan-1-on; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(furan-2-il)etanol; (1 S)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; (1 R)-1 -cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(jodometilen)cikloheksil)etanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)propan-1 -ol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)acetonitril; 1 -cikloheksil-3-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)propan-2-ol; 1 -cikloheksil-3-(5H-imidazo[5,1 -a]izoindol-5-il)propan-2-ol; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon; 1- (4,4-difluorocikloheksil)-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; 1 -(4,4-difluorocikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2- (6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1 -metil-1 H-imidazol-5-il)etanol; 1 -(4-(ciklopropilmetilen)cikloheksil)-2-(6-fluoro-5H-imidazo[5,1 -ajizoindol- 5- il)etanol; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(propan-2-iliden)cikloheksil)etanol; (E)-5-(2-cikloheksilvinil)-5H-imidazo[5,1 -ajizoindol; 2-(9-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-metilcikloheksil)etanol; 1-(cikloheks-3-en-1-il)-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; (S)-1 -cikloheksil-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; (R)-1 -cikloheksil-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; (R) -1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; (S) -1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-iliden)etanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -ajizoindol-5-il)etil acetat; 1 -(4-(2-(benziloksi)etiliden)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -(1 -(benzilsulfonil)piperidin-4-il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)-2-(pirimidin-5-il)etanon; 2-(3,4-difluorofenil)-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)etanon; cikloheksil(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)metanon; metil 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksankarboksilat; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]isoindal-5-il)etil fenilkarbamat; 4-(1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindal-5-il)ethoksi)-4-oksobutanojska kislina; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksanol; 1- cikloheksil-2-(5H-imidazo[5,1-a]izoindol-5-il)etil benzoat; 4-(1-hidroksi-2-(5H-imidazo[5,1-al]izoindol-5-il)etil)-N-(2-(metilsulfonamido)etil)cikloheksankarboksamid; (2S)-1-cikloheksil-2-(5H-imidazo[5,1-a]-izoindol-5-il)etil-2-amino-3-metilbutanoat; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil divodik fosfat; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksankarboksilna kislina; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(piridin-4-il)etanon; 2- (5H-imidazo[5,1-a]izoindol-5-il)-1-(spiro[2.5]octan-6-il)etanol; 2-(4-fluorofenil)-1-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1 -il)etanon; (2S)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil 2-aminopropanoate; 1 -(4-(2-hidroksietiliden)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; (2S)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil pirolidin-2-karboksilat; (2S)-5-(1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil) 1 -metil 2-aminopentanedioat; 1 -(4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon; (3-fluoro-2-hidroksifenil)(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izomdoli-5- il)etil)piperidin-1-il)metanon; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1 -karboksamid; (4-fluorofenil)(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin- 1-il)metanon; (2S)-2-amino-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-3-fenilpropan-1 -on; (4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)((S)-pirolidin-2-il) metanon; (1 R,4s)-4-(2-((S)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-hidroksietil) cikloheksil benzoat; (1 R,4s)-4-(2-((S)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil) cikloheksanol; 1 -(3-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)azetidin-1 -il)-2-feniletanon; 3- (1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilazetidin-1 -karboksamid; tert-butil 3-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)azetidin-1 -karboksilat 1 -(azetidin-3-il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; tert-butil 4-((S)-1-hidroksi-2-((R)-5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1 -karboksilat; tert-butil 4-((R)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksilat; tert-butil 4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,l-a]izoindol-5-il)etil)piperidin-1 -karboksilat; tert-butil 4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1-a]izomdol-5-il)etil)piperidin-1 -karboksilat; 1- ((1s,4s)-4-(benziloksi)cikloheksil)-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1 -a]izoindol-5-il)-1 -(piridin-3-il)etanol; (1r,4r)-4-(2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-hidroksietil)cikloheksanol; 4- ((S)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1-karboksamid; 4-((R)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1-karboksamid; 4-((R)-1 -hidroksi-2-((S)-5H-imidiazo[5,1 -a]izoindol-5-il)elhil)-N-fenilpiperidin-1-karboksamid; 4-((S)-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)-N-fenilpiperidin- 1- karboksamid; 1 -(4((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)- 2- feniletanon; (1R,4s)-4-((S)-2-((R)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1- hidroksietil)cikloheksanol; (1S,4s)-4-((R)-2-((R)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1- hidroksietil)cikloheksanol; (1S,4s)-4-((R)-2-((S)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1- hidroksietil)cikloheksanol; (1 R,4s)-4-((S)-2-((S)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; (1S,4r)-4-((S)-2-((S)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1- hidroksietil)cikloheksanol; (1 S,4r)-4-((S)-2-((R)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietiljcikloheksanol; (1 R,4r)-4-((R)-2-((S)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; (1 R,4r)-4-((R)-2-((R)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietiljcikloheksanol; 1 -(4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(tetrahidro-2H-piran-4-il)etanon; 1 -(4-((R)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon; N-((1s,4s)-4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5- il)etil)cikloheksil)benzamid; 1 -(4-((S)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1 -(fenilcarbamoyl)piperidin-4-il)etil fenilkarbamat; 4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-((1 r,4R)-4-hidroksicikloheksil)piperidin-1-karboksamid; 4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(tetrahidro-2H-piran-4-il)piperidin-1-karboksamid; 4- ((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-((1 r,4S)-4-hidroksicikloheksil)piperidin-1-karboksamid; 1 -((1 r,4r)-4-(benziloksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -((1 r,4r)-4-(benziloksi)cikloheksil)-2-(6-fluoro-5H-imidazo[5,1 -a]izoindol- 5- il)etanol; 1 -(4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(tetrahidro-2H-piran-4-il)etanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(piridin-4-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(piridin-2-il)etanol; 4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(tetrahidro-2H-piran-4-il)piperidin-1-karboksamid; N-cikloheksil-4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; N-((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)benzamid; N-ciklopentil-4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(trifluorometil)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(trifluorometil)cikloheksil)etanol; 1 -(4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(4-(trifluorometil)fenil)etanon; 4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-A/-(4-(trifluorometil)fenil)piperidin-1-karboksamid; (4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)(1H-imidazol-1-il)metanon; 1 -(5H-imidazo[5,1 -a]izoindol-5-il)-3-metilbutan-2-ol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(tetrahidro-2H-piran-3-il)etanol; 2-(5H-imidazo[5,1 -ajizoindol-5-il)-1 -(piperidin-3-il)etanol; 1-cikloheksil-2-((R)-5H-imidazo[5,1-a]izoindol-5-il)etanol; 1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -cikloheksil-3-(5H-imidazo[5,1 -a]izoindol-5-il)propan-1 -ol; 1- cikloheksil-2-(9-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; N-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)fenil)-2-(tetrahidro-2H-piran-il)acetamid; 2- (5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1 H-imidazol-2-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1 H-imidazol-4-il)etanol; 2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-(tiazol-2-il)etanol; (5S)-5-(2-cikloheksil-2-hidroksietil)-5H-imidazo[5,1-a]izoindol-6-ol; 1- (2-amocikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; N-(1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)acetamid; N-(2-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)acetamid; 1 -cikloheksil^SH-imidazoIS, 1 -a]izoindol-5-il)-N-metilethanamin; 2- ((1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)amino)etansulfonamid; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1 -metilpiperidin-4-il)etanol; 1 -(4-aminocikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; N-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)acetamid; 1- (4-(aminometil)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)cikloheksankarboksamid; 1 -(3-aminocikloheksil)2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1-a]izoindol-5-il)-1-((1r,4r)-4-(piridin-2-ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1-a]izoindol-5-il)-1-((1r,4r)-4-(piridin-3- ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(piridin-4-ilmetoksi)cikloheksil)etanol; 1 -((1 r,4r)-4-((2-aminopiridin-4-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(pyrazin-2-ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(pirimidin-5-ilmetoksi)cikloheksil)etanol; 1-((1 r,4r)-4-((6-aminopiridin-2-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 1 -((1 ^^-((e-aminopiridin-S-ilJmetoksOcikloheksil^-iSH-imidazotS, 1 -a]izoindol-5-il)etanol; 1 -((1 rI4r)-4-((3-aminopiridin-2-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1-((1 r,4r)-4-((2-aminopirimidin-5-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1- ((1 r, 4r)-4-((4-aminopirimidin-5-il)metoksi)cikloheksil)-2-(5H-imidazofS, 1 -a]izoindol-5-il)etanol; 1 -((1 r,4r)-4-((5-aminopiridin-2-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1 -aJizoindol-5-il)etanol; 4-((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)-N,N-dimetilbenzamid; 3- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)cikloheksil)oksi)metil)-N,N-dimetilbenzamid; 2- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)-N,N-dimetilbenzamid; 4- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 3- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 2- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 4- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzamid; 3- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzamid; 2-((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5- il)etil)cikloheksil)oksi)metil)benzamid; metil 4-((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5- il)etil)cikloheksil)oksi)metil)benzoat; metil 3-((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5- il)etil)cikloheksil)oksi)metil)benzoat; metil 2-((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5- il)etil)cikloheksil)oksi)metil)benzoat; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-methoxycikloheksil)etanol; 1 -((1 r,4r)-4-ethoxycikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(5H-imidazo[5,1-a]izoindol-5-il)-1-((1r,4r)-4-izopropoksicikloheksil)etanol; 1- ((1r,4r)-4-(ciklopropilmetoksi)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol- 5- il)etanol; 1 -((1 r,4r)-4-(ciklopentilmetoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol- 5- il)etanol; 2- (5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(thiophen-2-ilmetoksi)cikloheksil)etanol; 1- ((1 rl4r)-4-((1H-indol-3-il)oksi)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol- 5-il)etanol; 1 -((1 r,4r)-4-((1 H-indol-5-il)oksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1-a]izoindol-5-il)-1-(4-((tetrahidro-2H-piran-4-il)metoksi)cikloheksil)etanol; 4- (((4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(oxazol-2-ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(tiazol-2-ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1-a]izoindol-5-il)-1-(1-(1-imino-2-feniletil)piperidin-4-il)etanol; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1 -karboksimidamid; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(piridin-4-il)piperidin-1 -karboksimidamid; 4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)-N-(tetrahidro-2H- piran-4-il)piperidin-1-karboksimidamid; N-(4-cianofenil)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; N-(tert-butil)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; N-(tert-butil)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin- 1- sulfonamid; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(3-hidroksifenil)etanon; 2- (1 -(azetidin-1 -ogljikyl)piperidin-4-il)-2-hidroksi-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)etanon; 2-ciklopentil-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -iljetanon; 1- (4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)-2-(2-metiltiazol-5-il)etanon; N-cikloheksil-N-hidroksi-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; N-(4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)- 2- oksoetil)fenil)metansulfonamid; N-ciklopropil-N-hidroksi-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; 3,3-difluoro-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-il)butan-1-on; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(p-tolyl)etanon; 1 -(1 -(4-aminopirimidin-2-il)piperidin-4-il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -(1 -(2-aminopirimidin-4-il)piperidin-4-il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; N-ciklopropil-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a] izoi nd ol-5-i l)eti I) pi perid i n- 1- karboksamid; 2- ciklopropil-1 -(4-(1 -hidroksi-2-(5H-imidazo [5,1 -a]izoindol-5-il)etil)piperidin-1-il)etanon; 2-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)cikloheksilidene)acetonitril; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(4-(trifIuorometil)tiazol-2-il)piperidin-1-karboksamid; 4-(2-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)-2-oksoetiljbenzamid; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(4-(metilsulfonil)fenil)etanon; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-((1 r,4r)-4-metilcikloheksil)piperidin-1-karboksamid; 1- (4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)-3,3-dimetilbutan-1-on; 4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)-2-oksoetiljbenzenesulfonamid ; N-(tert-butil)-4-(2-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5- il)etil)piperidin-1-il)-2-oksoetil)benzenesulfonamid; 4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-oksoetil)benzojska kislina; 1 -(4-(difluorometilen)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1-a]izoindol-5-il)-1-(4-(2,2,2-trifluoroetiliden)cikloheksil)etanol; N-benzil-4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksankarboksamid; 4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)-N-fenilcikloheksankarboksamid; N-(4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksil)benzamid; 1 -(4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksil)- 3- fenilurea; N-(4-(2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-hidroksietil)cikloheksil)- 2-fenilacetamid; ali njega farmacevtsko sprejemljiva sol.
- 2. Sestavek po zahtevku 1, pri čemer je spojina 4-((R)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)-N-fenilpiperidin-1-karboksamid ali njega farmacevtsko sprejemljiva sol.
- 3. Sestavek po zahtevku 1, pri čemer je spojina 1-(4-((R)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il))piperidin-1-il)-2-feniletanon ali njega farmacevtsko sprejemljiva sol.
- 4. Sestavek po zahtevku 1, pri čemer je spojina 1-(4-((S)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il))piperidin-1-il)-2-feniletanon ali njega farmacevtsko sprejemljiva sol.
- 5. Sestavek po zahtevku 1, pri čemer je spojina (S)-1-cikloheksil-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etanol ali njega farmacevtsko sprejemljiva sol.
- 6. Sestavek po zahtevku 1, pri čemer je spojina (1 R,4r)-4-((R)-2-((S)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol ali njega farmacevtsko sprejemljiva sol.
- 7. Spojina po formuliali nje farmacevtsko sprejemljiva sol za uporabo pri zdravljenju bolezni in motenj, ki jih mediira indoleamin-2,3-dioksigenaza, pri čemer vez a je enojna ali dvojna vez; nje 0, 1,2, 3, ali 4; vsak R1 je neodvisno halogen, ciano, nitro, Ci-ealkil, Ci-6haloalkil, -OR, -N(R)2, -SR, -C(0)0R, -C(0)N(R)2i -C(0)R, -S(0)R, -S(0)OR, -S(0)N(R)2, -S(0)2R, -S(0)20R, -S(0)2N(R)2i -OC(0)R, -0C(0)0R, -0C(0)N(R)2, -N(R)C(0)R, -N(R)C(0)0R, ali -N(R)C(0)N(R)2; R2 je -Ci^alkil-RA ali -C2-4alkenil-R3 kadar vez a je enojna vez; in R2 je =C(H)RA kadar vez a je dvojna vez; pri čemer RA je -CN, -C(0)R3, -C(0)0R3, -C(0)N(R3)(Rc), -C(ORB)(R3)(Rc), -C(NHRB)(R3)(Rc), ali -C(=N-ORc)R3, pri čemer RB je vodik, Ci-ealkil, Ci-ehaloalkil, -Ci-ealkil-RB1, -C(0)R3, -C(0)N(H)R3, ali -S(0)2R3, -C(0)(CH2)i-4COOR, -C(0)(CH2)i-4(NR)C00R, -C(0)CH(NH2)(Rd), -S(0)20R3, -S(0)2N(R3)2, -CH2-0P(0)2(0R)2, ali -P(0)(0R3)2, pri čemer RB1 je ciano, nitro, Ci-ealkil, Ci-6haloalkil, -OR, -N(R)2, -SR, -C(0)0R, -C(0)N(R)2i -C(0)R, -S(0)R, -S(0)0R, -S(0)N(R)2, -S(0)2R, -S(0)20R, -S(0)2N(R)2, -0C(0)R, -0C(0)0R, -0C(0)N(R)2, -N(R)C(0)R, -N(R)C(0)0R, ali -N(R)C(0)N(R)2; RD je vodik, metil, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)(CH2CH3), benzil, 4-hidroksibenzil, -CH2(3-indolil), -CH2SH, -CH2CH2SCH3, -CH2OH, -CH(CH3)OH, -(CH2)4-NH2i -(CH2)3-N(H)C(=NH)NH2, -CH2(4-imidazolil), -CH2COOH, -CH2CH2COOH,-CH2CONH2, -CH2CH2CONH2; vsak R3 je neodvisno vodik, Ci-6alkil, Ci-6haloalkil, aril, heteroaril, C3-ecikloalkil, C3-8Cikloalkenil, 3-10 članski heterociklil, arilCi-ealkil-, heteroarilCi-6 alkil-, C3-ecikloalkilCi-6alkil-, C3-8CikloalkenilCi-ealkil-, (3-10 članski heterociklil)Ci-6alkil-, ali (heteroaril)-(3-10 članski heterociklil)-, pri čemer alkil, C3-8Cikloalkil, C3-scikloalkenil, 3-10 članski heterociklil, C3-ecikloalkilCi-ealkil-, C3-8CikloalkenilCi-6alkil-, (3-10 članski heterociklil)Ci-6alkil-, in (heteroaril)-(3-10 članski heterociklil)-, so vsak opcijsko in neodvisno substituirani z eno =R32 skupino in vsak opcijsko substituirani in neodvisno z eno, dvema, tremi, ali štirimi R31 skupinami; aril, heteroaril, arilCi-ealkil-, in heteroarilCi-6alkil- skupine so vsaka opcijsko substituirane z eno, dvema, tremi, ali štirimi R31 skupinami; pri čemer vsak R31 je neodvisno halogen, ciano, nitro, Ci-ealkil, -Ci-6alkil-R33, Ci-ehaloalkil, -OR, -N(R)2, -SR, -C(0)OR, -C(0)N(R)2i -C(0)N(OH)R, -C(0)R, -C(NR11)R, -C(NR11)N(R11)R, -S(0)R, -S(0)OR, -S(0)N(R)2, - S(0)2R, -S(0)20R, -S(0)2N(R)2, -0C(0)R, -0C(0)0R, -0C(0)N(R)2i - N(R)C(0)R, -N(R)C(0)0R, -N(R)C(0)N(R)2i pri čemer R33 je ciano, -OR, -N(R)2, -SR, -C(0)0R, -C(0)N(R)2, -C(0)R, -S(0)R, - S(0)0R, -S(0)N(R)2, -S(0)2R, -S(0)20R, -S(0)2N(R)2i -0C(0)R, - 0C(0)0R, -0C(0)N(R)2, -N(R)C(0)R, -N(R)C(0)0R, ali - N(R)C(0)N(R)2; R32 je =0, =S, =N(R), =N(OR), =C(R34)2, =(spiro-C3-8Cikloalkil), ali =(spiro-(3-10 članski heterociklil)), pri čemer vsak R34 je neodvisno vodik, halogen, ciano, Ci-ealkil, - Ci-ealkil-OR, Ci-ehaioalkil, C3-8cikloalkil, ali 3-10 članski heterociklil; ali obe R34 vzeti skupaj z atomom, h kateremu sta obe pripeti tvorita monociklični C3-8cikloalkil ali monociklični 3-8 članski heterociklil; Rc je vodik ali Ci-ealkil; in vsak R je neodvisno vodik ali R10, pri čemer R10 je Ci-ealkil, Ci-ehaloalkil, aril, heteroaril, C3-8dkloalkil, C3-8cikloalkenil, 3-10 članski heterociklil, arilCi-ealkil, heteroarilCi-ealkil-, C3-8 cikloalkilCi-ealkil-, C3-8cikloalkenilCi-6alkil-, ali (3-10 članski heterociklil)Ci-6alkil-, vsak R10 opcijsko substituiran z eno, dvema, tremi, ali štirimi skupinami, ki so vsak neodvisno halogen, ciano, nitro, Ci-ealkil, Ci-6haloalkil, -OR11, -N(R11)2, -SR11, -C(0)0R11, -C(0)N(R11)2, -C(0)R11, -S(0)R11, -S(0)0R11, -S(0)N(R11)2, -S(0)2R11, -S(0)20R11, -S(0)2N(R11)2i -0C(0)R11, -OC(0)OR11, -0C(0)N(R11)2, -N(R11)C(0)R11, -N(R11)C(0)0R11, -N(R11)C(0)N(R11)2i-N(R11)S(0)2R11, ali -C(O)-(3-10 članski heterociklil), pri čemer je vsak R11 neodvisno vodik ali Ci-ealkil.
- 8. Spojina za uporabo po zahtevku 7, ki je 2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; etil 2-(5H-imidazo[5,1-a]izoindol-5-il)acetat; (E)-5-(2-bromostiril)-5H-imidazo[5,1 -ajizoindol; 2-(6-kloro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -cikloheksiletanol; 2-(6-kloro-5H-imidazo[5,1-a]izoindol-5-il)-1-cikloheksiletanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)etil2-(((1 R,2R,5S)-2-izopropil-5-metilcikloheksil)oksi)acetat; tert-butil (4-(2-(5H-imidazo[5,1 -a]izoindol-5-il)acetil)fenil)karbamat; 1-(4-amofenil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanon; tert-butil (4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)fenil)karbamat; 1- (4-aminofenil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1 -a]izoindol-5-il)-1 -(3-nitrofenil)etanon; 2-(5H-imidazo[5,1 -ajizoindol-5-il)-1 -(3-nitrofenil)etanol; 2-(5H-imidazo[5,1 -a] izoi ndol-5-i I)-1 -(2-nitrofenil)etanon; 2-(5H-imidazo[5,1 -a] izoi ndol-5-i I)-1 -(2-nitrofenil)etanol; tert-butil (2-(2-(5H-imidazo[5,1 -a]izoindol-5-il)acetil)fenil)karbamat; tert-butil (2-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)fenil)karbamat; 1 -(2-aminofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanon; 1 -(2-aminofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1-(2-klorofenil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanon; 1 -(5H-imidazo[5,1 -a]izoindol-5-il)-2-metilpropan-2-ol; 1-(2-klorofenil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 1- (3-klorofenil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1 -a]izoindol-5-il)-1 -feniletanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -feniletanol; 1-(2,4-dimetilfuran-3-il)-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; 1-(3-klorofenil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanon; 1- cikloheksil-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanon; 1 -cikloheksil-2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1-a]izoindol-5-il)-1-(tetrahidro-2H-piran-4-il)etanol; 2-(7-kloro-5H-imidazo[5,1-a]izoindol-5-il)-1-cikloheksiletanol; (Z)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanon oksim; 1 -ciklopentil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; tert-butil 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 - karboksilat; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanamin; tert-butil (3-(1-hidroksi-2-(5H-imidazo[5,1-a3izoindol-5-il)etil)fenil)karbamat; 1-(3-aminofenil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 4- (2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; 1- cikloheksil-2-(9-methoxy-5H-imidazo[5,1-a]izoindol-5-il)etanol; 5- (2-cikloheksil-2-hidroksietil)-5H-imidazo[5,1-a]izoindol-9-ol; 2- (8-kloro-5H-imidazo[5,1 -a]izoi ndol-5-i I)-1 -cikloheksiletanol; 1 -(cikloheks-1 -en-1 -il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1- cikloheksil-2-(8-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; 2- (6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1-(1,4-dioksaspiro[4.5]dekan-8-il)etanol; 4-(2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1- hidroksietil)cikloheksanone; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-metilencikloheksil)etanol; 1 -(cikloheks-3-en-1 -il)-2-(5H-imidazo [5,1 -a]izoindol-5-il)etanol; 1 -(4-(hidroksimetil)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; (4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)(thiophen-2-il)metanon; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)etanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-metilencikloheksil)etanol; 2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-(4-metilcikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(tiazol-4-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(tiazol-5-il)etanol; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2,2-dimetilpropan-1-on; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(furan-2-il)etanol; (1 S)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; (1R)-1-cikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(jodometilen)cikloheksil)etanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)propan-1 -ol; 2-(5H-imidazo[5,1-a]izoindol-5-il)acetonitril; 1 -cikloheksil-3-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)propan-2-ol; 1 -cikloheksil-3-(5H-imidazo[5,1 -a]izoindol-5-il)propan-2-ol; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon; 1 -(4,4-difluorocikloheksil)-2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -(4,4-difluorocikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1 -metil-1 H-imidazol-5-il)etanol; 1 -(4-(ciklopropilmetilen)cikloheksil)-2-(6-fluoro-5H-imidazo[5,1 -ajizoindol- 5-il)etanol; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(propan-2-iliden)cikloheksil)etanol; (E)-5-(2-cikloheksilvinil)-5H-imidazo[5,1 -a]izoindol; 2-(9-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-metilcikloheksil)etanol; 1-(cikloheks-3-en-1-il)-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; (S)-1 -cikloheksil-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; (R)-1 -cikloheksil-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; (R) -1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; (S) -1-cikloheksil-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-iliden)etanol; 1-cikloheksil-2-(5H-imidazo[5,1-a]izoindol-5-il)etil acetat; 1 -(4-(2-(benziloksi)etiliden)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1- (1-(benzilsulfonil)piperidin-4-il)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoind ol-5-i l)eti I) p ipe rid i n-1 -il)-2-(pirimidin-5-il)etanon; 2- (3,4-difluorofenil)-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)etanon; cikloheksil(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)metanon; metil 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksankarboksilat; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]isoindal-5-il)etil fenilkarbamat; 4-(1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindal-5-il)ethoksi)-4-oksobutanojska kislina; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil benzoat; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -al]izoindol-5-il)etil)-N-(2-(metilsulfonamido)etil)cikloheksankarboksamid; (2S)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]-izoindol-5-il)etil-2-amino-3-metilbutanoat; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil divodik fosfat; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksankarboksilna kislina; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(piridin-4-il)etanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(spiro[2.5]octan-6-il)etanol; 2- (4-fluorofenil)-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-il)etanon; (2S)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil 2-aminopropanoate; 1 -(4-(2-hidroksietiliden)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; (2S)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil pirolidin-2-karboksilat; (2S)-5-(1 -cik1 oheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil) 1 -metil 2-aminopentanedioat; 1 -(4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon; (3-fluoro-2-hidroksifenil)(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-il)metanon; 4- ( 1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1 -karboksamid; (4-fluorofenil)(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-il)metanon; (2S)-2-amino-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-3-fenilpropan-1 -on; (4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)((S)-pirolidin-2-il) metanon; (1 R,4s)-4-(2-((S)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-hidroksietil) cikloheksil benzoat; (1R,4s)-4-(2-((S)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-hidroksietil) cikloheksanol; 1-(3-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)azetidin-1-il)-2- feniletanon; 3- (1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilazetidin-1 -karboksamid; tert-butil 3-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)azetidin-1 -karboksilat 1- (azetidin-3-il)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; tert-butil 4-((S)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksilat; tert-butil 4-((R)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -karboksilat; tert-butil 4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,l-a]izoindol-5-il)etil)piperidin-1 -karboksilat; tert-butil 4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -karboksilat; 1 -((1 s,4s)-4-(benziloksi)cikloheksil)-2-(6-fluoro-5H-imidazo[5,1 -a]izoindol- 5- il)etanol; 2- (5H-imidazo[5,1-a]izoindol-5-il)-1-(piridin-3-il)etanol; (1 rt4r)-4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; 4-((S)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1-karboksamid; 4-((R)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1-karboksamid; 4-((R)-1 -hidroksi-2-((S)-5H-imidiazo[5,1 -a]izoindol-5-il)elhil)-N-fenilpiperidin-1-karboksamid; 4-((S)-hidroksi-2-((S)-5H-imidazo[5)1-a]izoindol-5-il)etil)-N-fenilpiperidin- 1- karboksamid; 1 -(4((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)- 2- feniletanon; (1 R,4s)-4-((S)-2-((R)-6-fluoro-5H-imidazo[511 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; (1 S,4s)-4-((R)-2-((R)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; (1 S,4s)-4-((R)-2-((S)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -h id roksietil)cikloheksanol; (1 R,4s)-4-((S)-2-((S)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; (1 S,4r)-4-((S)-2-((S)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -h id roksietil)cikloheksanol; (1S,4r)-4-((S)-2-((R)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1- hidroksietil)cikloheksanol; (1R,4r)-4-((R)-2-((S)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1- hidroksietil)cikloheksanol; (1 R^O^-^RJ^-iiRJ-e-fluoro-SH-imidazoiS, 1 -a]izoindol-5-il)-1 -hidroksietiljcikloheksanol; 1-(4-((S)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1- il)-2-(tetrahidro-2H-piran-4-il)etanon; 1 -(4-((R)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon; N-((1s,4s)-4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5- il)etil)cikloheksil)benzamid; 1- (4-((S)-1-hidroksi-2-((R)-5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)-2-feniletanon; 2- (5H-imidazo[5,1-a]izoindol-5-il)-1-(1-(fenilcarbamoyl)piperidin-4-il)etil fenilkarbamat; 4-((R)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)-N-((1r,4R)-4- hidroksicikloheksil)piperidin-1-karboksamid; 4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(tetrahidro-2H-piran-4-il)piperidin-1-karboksamid; 4- ((S)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)-N-((1r)4S)-4-hidroksicikloheksil)piperidin-1-karboksamid; 1 -((1 r,4r)-4-(benziloksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1-((1 r,4r)-4-(benziloksi)cikloheksil)-2-(6-fluoro-5H-imidazo[5,1 -a]izoindol- 5- il)etanol; 1 -(4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(tetrahidro-2H-piran-4-il)etanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(piridin-4-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1-(piridin-2-il)etanol; 4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(tetrahidro-2H-piran-4-il)piperidin-1-karboksamid; N-cikloheksil-4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; N-((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)benzamid; N-ciklopentil-4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; 2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-(4-(trifluorometil)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(trifluorometil)cikloheksil)etanol; 1 -(4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(4-(trifluorometil)fenil)etanon; 4-((R)-1 -hidroksi-2-((S)-5/-/-imidazo[5,1 -a]izoindol-5-il)etil)-/S/-(4-(trifluorometil)fenil)piperidin-1-karboksamid; (4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)(1 H-imidazol-1 -il)metanon; 1 -(5H-imidazo[5,1 -a]izoindol-5-il)-3-metilbutan-2-ol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(tetrahidro-2H-piran-3-il)etanol; 2-(5H-imidazo[5,1-a]izoindol-5-il)-1-(piperidin-3-il)etanol; 1 -cikloheksil-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -cikloheksil-3-(5H-imidazo[5,1 -a]izoindol-5-il)propan-1 -ol; 1 -cikloheksil-2-(9-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)etanol; N-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)fenil)-2-(tetrahidro- 2H-piran-il)acetamid; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1 H-imidazol-2-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1 H-imidazol-4-il)etanol; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(tiazol-2-il)etanol; (5S)-5-(2-cikloheksil-2-hidroksietil)-5H-imidazo[5,1-a]izoindol-6-ol; 1 -(2-aminocikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; N-(1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)acetamid; N-(2-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5- il)etil)cikloheksil)acetamid; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)-N-metilethanamin; 2-((1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)amino)etansulfonamid; 2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-(1-metilpiperidin-4-il)etanol; 1 -(4-aminocikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; N-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)cikloheksil)acetamid; 1 -(4-(aminometil)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksankarboksamid; 1 -(3-aminocikloheksil)2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(5H-imidazo[5,1-a]izoindol-5-il)-1-((1r,4r)-4-(piridin-2- ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(piridin-3-ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(piridin-4-ilmetoksi)cikloheksil)etanol; 1 -((1 r,4r)-4-((2-aminopiridin-4-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(pyrazin-2-ilmetoksi)cikloheksil)etanol; 2- (5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(pirimidin-5-ilmetoksi)cikloheksil)etanol; 1 -((1 r,4r)-4-((6-aminopiridin-2-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -((1 r,4r)-4-((6-aminopiridin-3-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -((1 r,4r)-4-((3-aminopiridin-2-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1-((1 r, 4r)-4-((2-aminopirimidin-5-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 1- ((1 r,4r)-4-((4-aminopirimidin-5-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 1 -((1 r,4r)-4-((5-aminopiridin-2-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 4-((((1 r,4r)-4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)cikloheksil)oksi)metil)-N,N-dimetilbenzamid; 3- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)-N,N-dimetilbenzamid; 2- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)-N,N-dimetilbenzamid; 4- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 3- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 2- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 4- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzamid; 3- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzamid; 2-((((1 r,4r)-4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5- il)etil)cikloheksil)oksi)metil)benzamid; metil 4-((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5- il)etil)cikloheksil)oksi)metil)benzoat; metil 3-((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzoat; metil 2-((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzoat; 2-(5H-imidazo[5,1-a]izoindol-5-il)-1-((1r,4r)-4-methoxycikloheksil)etanol; 1 -((1 r,4r)-4-ethoxycikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-izopropoksicikloheksil)etanol; 1 -((1 r,4r)-4-(ciklopropilmetoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol- 5-il)etanol; 1 -((1 r,4r)-4-(ciklopentilmetoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol- 5-il)etanol; 2-(5H-imidazo[5,1-a]izoindol-5-il)-1-((1r,4r)-4-(thiophen-2- ilmetoksi)cikloheksil)etanol; 1 -((1 r,4r)-4-((1 H-indol-3-il)oksi)cikloheksil)-2-(5H-imidazo[5,1 -ajizoindol-5-il)etanol; 1 -((1 r,4r)-4-((1 H-indol-5-il)oksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-((tetrahidro-2H-piran-4-il)metoksi)cikloheksil)etanol; 4-(((4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(oxazol-2-ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(tiazol-2-ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1 -(1 -imino-2-feniletil)piperidin-4-il)etanol; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1 -karboksimidamid; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(piridin-4-il)piperidin-1 -karboksimidamid; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(tetrahidro-2H-piran-4-il)piperidin-1-karboksimidamid; N-(4-cianofenil)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; N-(tert-butil)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; N-(tert-butil)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin- 1- sulfonamid; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(3-hidroksifenil)etanon; 2- (1 -(azetidin-1 -ogljikyl)piperidin-4-il)-2-hidroksi-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)etanon; 2-ciklopentil-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)etanon; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(2-metiltiazol-5-il)etanon; N-cikloheksil-N-hidroksi-4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5- il)etil)piperidin-1-karboksamid; N-(4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-oksoetil)fenil)metansulfonamid; N-ciklopropil-N-hidroksi-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -karboksamid; 3,3-difluoro-1-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1 -il)butan-1 -on; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(p-tolyl)etanon; 1 -(1 -(4-aminopirimidin-2-il)piperidin-4-il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -(1 -(2-aminopirimidin-4-il)piperidin-4-il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; N-ciklopropil-4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin- 1- karboksamid; 2- ciklopropil-1 -(4-(1 -hidroksi-2-(5H-imidazo [5,1 -a]izoindol-5-il)etil)piperidin-1-il)etanon; 2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-ii)etii)cikloheksiiidene)acetonitril; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(4-(trifluorometil)tiazol-2-il)piperidin-1-karboksamid; 4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-oksoetil)benzamid; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(4-(metilsulfonil)fenil)etanon; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-((1 r,4r)-4-metilcikloheksil)piperidin-1-karboksamid; 1-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)-3,3- dimetilbutan-1-on; 4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-oksoetiljbenzenesulfonamid ; N-(tert-butil)-4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-il)-2-oksoetil)benzenesulfonamid; 4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-oksoetiljbenzojska kislina; 1- (4-(difluorometilen)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1-a]izoindol-5-il)-1-(4-(2,2,2-trifluoroetiliden)cikloheksil)etanol; N-benzil-4-(2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-hidroksietil)cikloheksankarboksamid; 4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)-N-fenilcikloheksankarboksamid; N-(4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksil)benzamid; 1 -(4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksil)- 3- fenilurea; N-(4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksil)-2-fenilacetamid; ali nje farmacevtsko sprejemljiva sol.
- 9. Spojina za uporabo po zahtevku 7, ki je 4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1 -karboksamid, 1-(4-((R)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)-2- feniletanon, 1 -(4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon, (S)-1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etanol(1 R,4r)-4-((R)-2-((S)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol, ali nje farmacevtsko sprejemljiva sol.
- 10. Spojina po formuliali nje farmacevtsko sprejemljiva sol za uporabo pri zdravljenju z indoleamin 2,3-dioksigenazo (IDO) mediirano imunosupresijo, pri čemer vez a je enojna ali dvojna vez; n je 0,1, 2, 3, ali 4; vsak R1 je neodvisno halogen, ciano, nitro, Ci-6alkil, Ci-ehaloalkil, -OR, -N(R)2, -SR, -C(0)0R, -C(0)N(R)2i -C(0)R, -S(0)R, -S(0)0R, -S(0)N(R)2, -S(0)2R, -S(0)20R, -S(0)2N(R)2, -0C(0)R, -0C(0)0R, -0C(0)N(R)2, -N(R)C(0)R, -N(R)C(0)0R, ali -N(R)C(0)N(R)2; R2 je -Ci-4alkil-RA ali -C2^alkenil-R3 kadar vez a je enojna vez; in R2 je =C(H)RA kadar vez a je dvojna vez; pri čemer RA je -CN, -C(0)R3, -C(0)0R3, -0(O)N(R3)(Rc), -C(ORB)(R3)(Rc), -C(NHRB)(R3)(Rc), ali -C(=N-ORc)R3, pri čemer RB je vodik, Ci-ealkil, Ci-ehaloalkil, -Ci-6alkil-RB1, -C(0)R3, -C(0)N(H)R3, ali -S(0)2R3, -C(0)(CH2)i-4C00R, -C(0)(CH2)i-4(NR)COOR, -C(0)CH(NH2)(Rd), -S(0)20R3, -S(0)2N(R3)2i -CH2-OP(0)2(OR)2, ali -P(0)(0R3)2, pri čemer RB1 je ciano, nitro, Ci-ealkil, Ci-6haloalkil, -OR, -N(R)2, -SR, -C(0)0R, -C(0)N(R)2, -C(0)R, -S(0)R, -S(0)0R, -S(0)N(R)2i -S(0)2R, -S(0)20R, -S(0)2N(R)2, -0C(0)R, -0C(0)0R, -0C(0)N(R)2, -N(R)C(0)R, -N(R)C(0)0R, ali -N(R)C(0)N(R)2; RD je vodik, metil, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)(CH2CH3), benzil, 4-hidroksibenzil, -CH2(3-indolil), -CH2SH, -CH2CH2SCH3, -CH2OH, -CH(CH3)OH, -(CH2)4-NH2, -(CH2)3-N(H)C(=NH)NH2, -CH2(4-imidazolil), -CH2COOH, -CH2CH2COOH,-CH2CONH2, -CH2CH2CONH2; vsak R3 je neodvisno vodik, Ci-ealkil, Ci-6haloalkil, aril, heteroaril, C3-ecikloalkil, Cs-scikloalkenil, 3-10 članski heterociklil, arilCi-6alkil-, heteroarilCi-6 alkil-, C3-8CikloalkilCi-6alkil-, C3-8cikloalkenilCi-6alkil-, (3-10 članski heterociklil)Ci-ealkil-, ali (heteroaril)-(3-10 članski heterociklil)-, pri čemer aikil, C3-8Cikloalkil, C^cikloalkenil, 3-10 članski heterociklil, C3-ecikloalkilCi-ealkil-, C3-ecikloalkenilCi-6alkil-, (3-10 članski heterociklil)Ci-ealkil-, in (heteroaril)-(3-10 članski heterociklil)-, so vsak opcijsko in neodvisno substituirani z eno =R32 skupino in vsak opcijsko substituirani in neodvisno z eno, dvema, tremi, ali štirimi R31 skupinami; aril, heteroaril, arilCi-ealkil-, in heteroarilCi-ealkil- skupine so vsaka opcijsko substituirane z eno, dvema, tremi, ali štirimi R31 skupinami; pri čemer vsak R31 je neodvisno halogen, ciano, nitro, Ci-ealkil, -Ci-ealkil-R33, C1-ehaloalkil, -OR, -N(R)2, -SR, -C(0)0R, -C(0)N(R)2, -C(0)N(0H)R, -C(0)R, -C(NR11)R, -C(NR11)N(R11)R, -S(0)R, -S(0)OR, -S(0)N(R)2, -S(0)2R, -S(0)2OR, -S(0)2N(R)2, -0C(0)R, -0C(0)0R, -0C(0)N(R)2i -N(R)C(0)R, -N(R)C(0)0R, -N(R)C(0)N(R)2, pri čemer R33 je ciano, -OR, -N(R)2, -SR, -C(0)0R, -C(0)N(R)2, -C(0)R, -S(0)R, -S(0)0R, -S(0)N(R)2, -S(0)2R, -S(0)20R, -S(0)2N(R)2i -OC(0)R, -OC(0)OR, -0C(0)N(R)2, -N(R)C(0)R, -N(R)C(0)0R, ali -N(R)C(0)N(R)2; R32 je =0, =S, =N(R), =N(OR), =C(R34)2, =(spiro-C3-8Cikloalkil), ali =(spiro-(3-10 članski heterociklil)), pri čemer vsak R34 je neodvisno vodik, halogen, ciano, Ci-ealkif, - Ci-ealkil-OR, C1-ehaloalkil, C3-8cikloalkil, ali 3-10 članski heterociklil; ali obe R34 vzeti skupaj z atomom, h kateremu sta obe pripeti tvorita monociklični C3-8Cikloalkil ali monociklični 3-8 članski heterociklil; Rc je vodik ali Ci-ealkil; in vsak R je neodvisno vodik ali R10, pri čemer R10 je Ci-ealkil, Ci-ehaloalkil, aril, heteroaril, C3-8Cikloalkil, C3-8Cikloalkenil, 3-10 članski heterociklil, arilCi-ealkil, heteroarilCi-ealkil-, C3-8 cikloalkilCi-ealkil-, C3-8CikloalkenilCi-6alkil-, ali (3-10 članski heterociklil)Ci-6alki!-, vsak R10 opcijsko substituiran z eno, dvema, tremi, ali štirimi skupinami, ki so vsak neodvisno halogen, ciano, nitro, Ci-ealkil, Ci-6haloalkil, -OR11, -N(R11)2, -SR11, -C(0)OR11, -C(0)N(R11)2i -C(0)R11, -S(0)R11, -S(0)OR11, -S(0)N(R11)2, -S(0)2R11, -S(0)2OR11, -S(0)2N(R11)2, -OC(0)R11, -OC(0)OR11, -OC(0)N(R11)2, -N(R11)C(0)R11, -N(R11)C(0)OR11, -N(R11)C(0)N(R11)2,-N(R11)S(0)2R11, ali -C(O)-(3-10 članski heterociklil), pri čemer je vsak R11 neodvisno vodik ali Ci-ealkil.
- 11. Spojina za uporabo po zahtevku 10, ki je 2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; etil 2-(5H-imidazo[5,1 -a]izoindol-5-il)acetat; (E)-5-(2-bromostiril)-5H-imidazo[5,1 -ajizoindol; 2-(6-kloro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -cikloheksiletanol; 2-(6-kloro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -cikloheksiletanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)etil2-(((1 R,2R,5S)-2-izopropil-5-metilcikloheksil)oks i)acetat; tert-butil (4-(2-(5H-imidazo[5,1 -a]izoindol-5-il)acetil)fenil)karbamat; 1 -(4-aminofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanon; tert-butil (4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)fenil)karbamat; 1 -(4-aminofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(5H-imidazo[5,1-a]izoindol-5-il)-1-(3-nitrofenil)etanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(3-nitrofenil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(2-nitrofenil)etanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(2-nitrofenil)etanol; tert-butil (2-(2-(5H-imidazo[5,1-a]izoindol-5-il)acetil)fenil)karbamat; tert-butil (2-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)fenil)karbamat; 1 -(2-aminofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanon; 1 -(2-aminofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -(2-klorofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanon; 1 -(5H-imidazo[5,1 -a]izoindol-5-il)-2-metilpropan-2-ol; 1 -(2-klorofenil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -(3-klorofenil)-2-(5H-imidazo[5,1 -ajizoindol-5-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -feniletanon; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -feniletanol; 1-(2,4-dimetilfuran-3-il)-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; 1-(3-klorofenil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanon; 1-cikloheksil-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanon; 1- cikloheksil-2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1 -a]izoindol-5-il)-1 -(tetrahidro-2H-piran-4-il)etanol; 2-(7-kloro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -cikloheksiletanol; (Z)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]izomdol-5-il)etanon oksim; 1 -ciklopentil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; tert-butil 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 - karboksilat; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanamin; tert-butil (3-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)fenil)karbamat; 1- (3-aminofenil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 4- (2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; 1 -cikloheksil-2-(9-methoxy-5H-imidazo[5,1 -a]izoindol-5-il)etanol; 5- (2-cikloheksil-2-hidroksietil)-5H-imidazo[5,1-a]izoindol-9-ol; 2- (8-kloro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -cikloheksiletanol; 1 -(cikloheks-1 -en-1 -il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1- cikloheksil-2-(8-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; 2- (6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1,4-dioksaspiro[4.5]dekan-8-il)etanol; 4-(2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-l-hidroksietil)cikloheksanon; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-metilencikloheksil)etanol; 1 -(cikloheks-3-en-1 -il)-2-(5H-imidazo [5,1 -a]izoindo1 -5-il)etanol; 1 -(4-(hidroksimetil)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; (4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)(thiophen-2-il)metanon; 1-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)etanon; 2-(5H-imidazo[5,1-a]izoindol-5-il)-1-(4-metilencikloheksil)etanol; 2-(6-fluoro-5H-imidazo[5,1 -a]izomdol-5-il)-1 -(4-metilcikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izomdol-5-il)-1 -(tiazol-4-il)etanol; 2-(5H-imidazo[5,1 -ajizomdol-5-il)-1 -(tiazol-5-il)etanol; 1- (4-(1-hidroksi-2-(5H-imidazo[5,1-a]izomdol-5-il)etil)piperidin-1-il)-2,2-dimetilpropan-1-on; 2- (6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(furan-2-il)etanol; (1S)-1-cikloheksil-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; (1 R)-1 -cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(6-fluoro-5H-imidazo[5,1 -a]izomdol-5-il)-1 -(4-(jodometilen)cikloheksil)etanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)propan-1 -ol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)acetonitril; 1-cikloheksil-3-(6-fluoro-5H-imidazo[5,1-a]izomdol-5-il)propan-2-ol; 1 -cikloheksil-3-(5H-imidazo[5,1 -a]izoindol-5-il)propan-2-ol; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izomdol-5-il)etil)piperidin-1 -il)-2-feniletanon; 1 -(4,4-difluorocikloheksil)-2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1- (4,4-difluorocikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 2- (6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1 -metil-1 H-imidazol-5-il)etanol; 1 -(4-(ciklopropilmetilen)cikloheksil)-2-(6-fluoro-5H-imidazo[5,1 -a]izoindol- 5-il)etanol; 2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-(4-(propan-2-iliden)cikloheksil)etanol; (E)-5-(2-cikloheksilvinil)-5H-imidazo[5,1 -ajizoindol; 2-(9-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-metilcikloheksil)etanol; 1 -(cikloheks-3-en-1 -il)-2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)etanol; (S)-1 -cikloheksil-2-((R)-5H-imidazo[5,1 -a]izomdol-5-il)etanol; (R)-1 -cikloheksil-2-((R)-5H-imidazo[5,1 -a]izomdol-5-il)etanol; (R) -1 -cikloheksil-2-((S)-5H-imidazo[5,1 -ajizoindol-5-il)etanol; (S) -1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-iliden)etanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil acetat; 1 -(4-(2-(benziloksi)etiliden)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1- (1-(benzilsulfonil)piperidin-4-il)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,l-a]izoindol-5-il)etil)piperidin-1 -il)-2-(pirimidin-5-il)etanon; 2- (3,4-difluorofenil)-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)etanon; cikloheksil(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1- il)metanon; metil 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksankarboksilat; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]isoindal-5-il)etilfenilkarbamat; 4-(1-cikloheksil-2-(5H-imidazo[5,1-a]izoindal-5-il)ethoksi)-4-oksobutanojska kislina; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksanol; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil benzoat; 4-(1-hidroksi-2-(5H-imidazo[5,1-al]izoindol-5-il)etil)-N-(2- (metilsulfonamido)etil)cikloheksankarboksamid; (2S)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]-izoindol-5-il)etil-2-amino-3-metilbutanoat; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil divodik fosfat; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksankarboksilna kislina; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izomdol-5-il)etil)piperidin-1 -il)-2-(piridin-4-il)etanon; 2-(5H-imidazo[5,1-a]izoindol-5-il)-1-(spiro[2.5]octan-6-il)etanol; 2- (4-fluorofenil)-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-il)etanon; (2S)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil 2-aminopropanoate; 1 -(4-(2-hidroksietiliden)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; (2S)-1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil pirolidin-2-karboksilat; (2S)-5-(1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil) 1 -metil 2-aminopentanedioat; 1 -(4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon; (3-fluoro-2-hidroksifenil)(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)metanon; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1 -karboksamid; (4-fluorofenil)(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-il)metanon; (2S)-2-amino-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-3-fenilpropan-1 -on; (4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)((S)-pirolidin-2-il) metanon; (1 R,4s)-4-(2-((S)-6-fluoro-5H-imidazo[5,1 -a] izoi nd o l-5-i I)-1 -hidroksietil) cikloheksil benzoat; (1R,4s)-4-(2-((S)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-hidroksietil) cikloheksanol; 1 -(3-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)azetidin-1 -il)-2-feniletanon; 3- (1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilazetidin-1 -karboksamid; tert-butil 3-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)azetidin-1 -karboksilat 1 -(azetidin-3-il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; tert-butil 4-((S)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -karboksilat; tert-butil 4-((R)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -karboksilat; tert-butil 4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,l-a]izoindol-5-il)etil)piperidin-1-karboksilat; tert-butil 4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izomdol-5-il)etil)piperidin-1-karboksilat; 1 -((1 s,4s)-4-(benziloksi)cikloheksil)-2-(6-fluoro-5H-imidazo[5,1 -a]izoindol- 5-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1-(piridin-3-il)etanol; (1 r,4r)-4-(2-(6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-hidroksietil)cikloheksanol; 4-((S)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1-karboksamid; 4-((R)-1-hidroksi-2-((R)-5H-imidazo[5,1-a]izoindol-5-il)etil)-N- fenilpiperidin-1-karboksamid; 4-((R)-1 -hidroksi-2-((S)-5H-imidiazo[5,1 -a]izoindol-5-il)elhil)-N-fenilpiperidin-1-karboksamid; 4-((S)-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)-N-fenilpiperidin- 1- karboksamid; 1 -(4((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)- 2- feniletanon; (1 R,4s)-4-((S)-2-((R)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; (1 S,4s)-4-((R)-2-((R)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; (1S,4s)-4-((R)-2-((S)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1-hid roksietil)cikloheksanol; (1R,4s)-4-((S)-2-((S)-6-fluoro-5H-imidazo[5,1-a]izoindol-5-il)-1- hidroksietil)cikloheksanol; (1 S,4r)-4-((S)-2-((S)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; (1 S,4r)-4-((S)-2-((R)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksanol; (1 R,4r)-4-((R)-2-((S)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietiljcikloheksanol; (1 R,4r)-4-((R)-2-((R)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietiljcikloheksanol; 1 -(4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(tetrahidro-2H-piran-4-il)etanon; 1-(4-((R)-1-hidroksi-2-((R)-5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1- il)-2-feniletanon; N-((1 s,4s)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)benzamid; 1 -(4-((S)-1 -hidroksi-2-((R)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon; 2-(5H-imidazo[5,1-a]izoindol-5-il)-1-(1-(fenilcarbamoyl)piperidin-4-il)etil fenilkarbamat; 4-((R)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)-N-((1r,4R)-4- hidroksicikloheksil)piperidin-1-karboksamid; 4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izomdol-5-il)etil)-N-(tetrahidro-2H-piran-4-il)piperidin-1-karboksamid; 4- ((S)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)-N-((1r,4S)-4-hidroksicikloheksil)piperidin-1-karboksamid; 1- ((1r,4r)-4-(benziloksi)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 1 -((1 r,4r)-4-(benziloksi)cikloheksil)-2-(6-fluoro-5H-imidazo[5,1 -ajizoindol- 5- il)etanol; 1 -(4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(tetrahidro-2H-piran-4-il)etanon; 2- (5H-imidazo[5,1-a]izoindol-5-il)-1-(piridin-4-il)etanol; 2-(5H-imidazo[5,1 -ajizomdol-5-il)-1 -(piridin-2-il)etanol; 4-((R)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)-N-(tetrahidro- 2H-piran-4-il)piperidin-1-karboksamid; N-cikloheksil-4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; N-((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)benzamid; N-ciklopentil-4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izomdol-5-il)etil)piperidin-1-karboksamid; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(trifluorometil)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(trifluorometil)cikloheksil)etanol; 1 -(4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(4-(trifluorometil)fenil)etanon; 4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)-/V-(4-(trifluorometil)fenil)piperidin-1-karboksamid; (4-((R)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)(1 H-imidazol-1-il)metanon; 1 -(5H-imidazo[5,1 -a]izomdol-5-il)-3-metilbutan-2-ol; 2-(5H-imidazo[5,1 -ajizoindol-5-il)-1 -(tetrahidro-2H-piran-3-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(piperidin-3-il)etanol; 1-cikloheksil-2-((R)-5H-imidazo[5,1-a3izoindol-5-il)etanol; 1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -cikloheksil-3-(5H-imidazo[5,1 -a]izoindol-5-il)propan-1 -ol; 1- cikloheksil-2-(9-fluoro-5H-imidazo[5,1-a]izoindol-5-il)etanol; N-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)fenil)-2-(tetrahidro-2H-piran-il)acetamid; 2- (5H-imidazo[5,1 -a]izomdol-5-il)-1 -(1 H-imidazol-2-il)etanol; 2-(5H-imidazo[5,1-a]izomdol-5-il)-1-(1H-imidazol-4-il)etanol; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(tiazol-2-il)etanol; (5S)-5-(2-cikloheksil-2-hidroksietil)-5H-imidazo[5,1-a]izoindol-6-ol; 1-(2-aminocikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; N-(1-cikloheksil-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)acetamid; N-(2-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)acetamid; 1 -cikloheksil-2-(5H-imidazo[5,1 -a]izoindol-5-il)-N-metilethanamin; 2-((1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)amino)etansulfonamid; 2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1 -metilpiperidin-4-il)etanol; 1- (4-aminocikloheksil)-2-(5H-imidazo[5,1-a]izomdol-5-il)etanol; N-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)cikloheksil)acetamid; 1 -(4-(aminometil)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izomdol-5-il)etil)cikloheksankarboksamid; 1 -(3-aminocikloheksil)2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(piridin-2-ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(piridin-3-ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(piridin-4-ilmetoksi)cikloheksil)etanol; 1- ((1r,4r)-4-((2-aminopiridin-4-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1 -a]izomdol-5-il)-1 -((1 r,4r)-4-(pyrazin-2-ilmetoksi)cikloheksil)etanol; 2- (5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(pirimidin-5-ilmetoksi)cikloheksil)etanol; 1-((1r,4r)-4-((6-aminopiridin-2-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1- a]izoindol-5-il)etanol; 1-((1r,4r)-4-((6-aminopiridin-3-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1- a]izoindol-5-il)etanol; 1-((1 r^r^-iiS-aminopiridin^-iOmetoksOcikloheksil^-iSH-imidazoIS.I-a]izoindol-5-il)etanol; 1-((1 r,4r)-4-((2-aminopirimidin-5-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 1 -((1 r,4r)-4-((4-amopirimidin-5-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1- ((1r,4r)-4-((5-aminopiridin-2-il)metoksi)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 4-((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)-N,N-dimetilbenzamid; 3- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)-N,N-dimetilbenzamid; 2- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)-N,N-dimetilbenzamid; 4- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 3- ((((1 r,4r)-4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 2- ((((1 r,4r)-4-(1-hidroksi-2-(5H-imidazo[5,1-a]izomdol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 4- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzamid; 3- ((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzamid; 2-((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5- il)etil)cikloheksil)oksi)metil)benzamid; metil 4-((((1 r,4r)-4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5- il)etil)cikloheksil)oksi)metil)benzoat; metil 3-((((1 r,4r)-4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzoat; metil 2-((((1 r,4r)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzoat; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-methoxycikloheksil)etanol; 1 -((1 r,4r)-4-ethoxycikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-izopropoksicikloheksil)etanol; 1 -((1 r,4r)-4-(ciklopropilmetoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol- 5- il)etanol; 1 -((1 r,4r)-4-(ciklopentilmetoksi)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol- 5-il)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -((1 r,4r)-4-(thiophen-2-ilmetoksi)cikloheksil)etanol; 1- ((1r,4r)-4-((1H-indol-3-il)oksi)cikloheksil)-2-(5H-imidazo[5,1-a]izoindol-5-il)etanol; 1 -((1 r,4r)-4-((1 H-indol-5-il)oksi)cikloheksi|)-2-(5H-imidazo[5,1 -ajizoindol-5-il)etanol; 2- (5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-((tetrahidro-2H-piran-4-il)metoksi)cikloheksil)etanol; 4- (((4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)cikloheksil)oksi)metil)benzenesulfonamid; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(oxazol-2-ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(4-(tiazol-2-ilmetoksi)cikloheksil)etanol; 2-(5H-imidazo[5,1 -a]izoindol-5-il)-1 -(1-(1 -imino-2-feniletil)piperidin-4-il)etanol; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-fenilpiperidin-1 -karboksimidamid; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(piridin-4-il)piperidin-1-karboksimidamid; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(tetrahidro-2H-piran-4-il)piperidin-1-karboksimidamid; N-(4-cianofenil)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; N-(tert-butil)-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a] izoi nd ol-5-i l)etil)p ipe rid i n-1-karboksamid; N-(tert-butil)-4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin- 1- sulfonamid; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(3-hidroksifenil)etanon; 2- (1-(azetidin-1-ogljikyl)piperidin-4-il)-2-hidroksi-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)pipericlin-1-il)etanon; 2-ciklopentil-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-il)etanon; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(2-metiltiazol-5-il)etanon; N-cikloheksil-N-hidroksi-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-karboksamid; N-(4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-oksoetil)fenil)metansulfonamid; N-cidopropil-N-hidroksi-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -karboksamid; 3,3-difluoro-1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)butan-1 -on; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(p-tolyl)etanon; 1 -(1 -(4-aminopirimidin-2-il)piperidin-4-il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 1 -(1 -(2-aminopirimidin-4-il)piperidin-4-il)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; N-ciklopropil-4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin- 1- karboksamid; 2- ciklopropil-1 -(4-(1 -hidroksi-2-(5H-imidazo [5,1 -a]izoindol-5-il)etil)piperidin-1-il)etanon; 2-(4-(1-hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)cikloheksilidene)acetonitril; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-(4-(trifluorometil)tiazol-2-il)piperidin-1-karboksamid; 4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1-a]izoindol-5-il)etil)piperidin-1-il)-2-oksoetiljbenzamid; 1 -(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-(4-(metilsulfonil)fenil)etanon; 4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)-N-((1 r,4r)-4-metilcikloheksil)piperidin-1-karboksamid; 1 -(4-(1-hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-3,3-dimetilbutan-1-on; 4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-oksoetiljbenzenesulfonamid ; N-(tert-butil)-4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1-il)-2-oksoetil)benzenesulfonamid; 4-(2-(4-(1 -hidroksi-2-(5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-oksoetiljbenzojska kislina; 1 -(4-(difluorometilen)cikloheksil)-2-(5H-imidazo[5,1 -a]izoindol-5-il)etanol; 2- (5H-imidazo[5,1 -a] izoi nd ol-5-i I)-1 -(4-(2,2,2-trifluoroetiliden)cikloheksil)etanol; N-benzil-4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksankarboksamid; 4-(2-(6-fluoro-5H-imidazo[5,1 -ajizoindol-5-il)-1 -hidroksietil)-N-fenilcikloheksankarboksamid; N-(4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksil)benzamid; 1 -(4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksil)- 3- fenilurea; N-(4-(2-(6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-1 -hidroksietil)cikloheksil)-2-fenilacetamid; ali nje farmacevtsko sprejemljiva sol.
- 12. Spojina za uporabo po zahtevku 10, ki je 4-((R)-1-hidroksi-2-((S)-5H-imidazo[5,1-a]izoindol-5-il)etil)-N-fenilpiperidin-1- karboksamid, 1 -(4-((R)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon, 1 -(4-((S)-1 -hidroksi-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etil)piperidin-1 -il)-2-feniletanon, (S)-1 -cikloheksil-2-((S)-5H-imidazo[5,1 -a]izoindol-5-il)etanol(1 R,4r)-4-((R)-2-((S)-6-fluoro-5H-imidazo[5,1 -a]izoindol-5-il)-l-hidroksietil)cikloheksanol, ali nje farmacevtsko sprejemljiva sol.
- 13. Spojina za uporabo po kateremkoli od zahtevkov 10-12, pri čemer je imunosupresija povezana z rakom.
- 14. Spojina za uporabo po zahtevku 13, pri čemer je rak rak debelega črevesa, trebušne slinavke, prsi, prostate, pljuč, možganov, jajčnikov, materničnega vratu, testisa, ledvic, glave ali vratu ali limfoma, levkemija ali melanoma.
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| EP15197593.5A EP3018132B1 (en) | 2011-04-15 | 2012-04-12 | Fused imidazole derivatives useful as ido inhibitors |
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