JP2017149769A5 - - Google Patents
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- Publication number
- JP2017149769A5 JP2017149769A5 JP2017096307A JP2017096307A JP2017149769A5 JP 2017149769 A5 JP2017149769 A5 JP 2017149769A5 JP 2017096307 A JP2017096307 A JP 2017096307A JP 2017096307 A JP2017096307 A JP 2017096307A JP 2017149769 A5 JP2017149769 A5 JP 2017149769A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazo
- isoindol
- ethyl
- hydroxy
- cyclohexyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- -1 3-indolyl Chemical group 0.000 claims 45
- 239000000203 mixture Substances 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 27
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 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 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 102000006639 indoleamine 2,3-dioxygenase Human genes 0.000 claims 8
- 108020004201 indoleamine 2,3-dioxygenase Proteins 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 229940124597 therapeutic agent Drugs 0.000 claims 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 4
- 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 3
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 3
- 206010062016 Immunosuppression Diseases 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 229940127089 cytotoxic agent Drugs 0.000 claims 3
- 238000009472 formulation Methods 0.000 claims 3
- 230000001506 immunosuppresive effect Effects 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 229940095102 methyl benzoate Drugs 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 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 2
- 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 2
- 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 2
- 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 2
- YQNFLDBZFLCLLR-JTHBVZDNSA-N 4-[(1r)-1-hydroxy-2-[(5s)-5h-imidazo[5,1-a]isoindol-5-yl]ethyl]-n-phenylpiperidine-1-carboxamide Chemical compound C1CC([C@@H](C[C@@H]2N3C=NC=C3C3=CC=CC=C32)O)CCN1C(=O)NC1=CC=CC=C1 YQNFLDBZFLCLLR-JTHBVZDNSA-N 0.000 claims 2
- YGACXVRLDHEXKY-LRBMDJJVSA-N 4-[(1r)-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-LRBMDJJVSA-N 0.000 claims 2
- 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 2
- 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 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims 2
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 102000004887 Transforming Growth Factor beta Human genes 0.000 claims 2
- 108090001012 Transforming Growth Factor beta Proteins 0.000 claims 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 201000010881 cervical cancer Diseases 0.000 claims 2
- 230000000139 costimulatory effect Effects 0.000 claims 2
- 229960004397 cyclophosphamide Drugs 0.000 claims 2
- 229940088598 enzyme Drugs 0.000 claims 2
- 229960004961 mechlorethamine Drugs 0.000 claims 2
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 claims 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 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 2
- 229940127084 other anti-cancer agent Drugs 0.000 claims 2
- FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 claims 2
- 229960002340 pentostatin Drugs 0.000 claims 2
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 claims 2
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 claims 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 2
- 229960005486 vaccine Drugs 0.000 claims 2
- YTRRAUACYORZLX-UHUGOGIASA-N (1r)-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-UHUGOGIASA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- WHXGLOURXNAWRM-UHFFFAOYSA-N 1-(2-aminocyclohexyl)-2-(5h-imidazo[5,1-a]isoindol-5-yl)ethanol Chemical compound NC1CCCCC1C(O)CC1N2C=NC=C2C2=CC=CC=C21 WHXGLOURXNAWRM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
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