HRP20050624A2 - Diazepinoindole derivatives as kinaze inhibitors - Google Patents

Info

Publication number

HRP20050624A2

HRP20050624A2 HR20050624A HRP20050624A HRP20050624A2 HR P20050624 A2 HRP20050624 A2 HR P20050624A2 HR 20050624 A HR20050624 A HR 20050624A HR P20050624 A HRP20050624 A HR P20050624A HR P20050624 A2 HRP20050624 A2 HR P20050624A2

Authority

HR

Croatia

Prior art keywords

diazepino

dihydro

oxo

indol

alkyl

Prior art date

2003-01-09

Links

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• Global Dossier
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• 239000003112 inhibitor Substances 0.000 title description 31
• BSYFXFLGOGQHFU-UHFFFAOYSA-N pyrrolo[2,3-g][1,2]benzodiazepine Chemical class N1=NC=CC=C2C3=NC=CC3=CC=C21 BSYFXFLGOGQHFU-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 306
• 150000003839 salts Chemical class 0.000 claims abstract description 67
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 48
• 108060006633 protein kinase Proteins 0.000 claims abstract description 48
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 44
• 239000002246 antineoplastic agent Substances 0.000 claims abstract description 40
• 229940034982 antineoplastic agent Drugs 0.000 claims abstract description 38
• 238000011282 treatment Methods 0.000 claims abstract description 31
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
• 230000001225 therapeutic effect Effects 0.000 claims abstract description 17
• 101150050673 CHK1 gene Proteins 0.000 claims abstract 3
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 152
• -1 [2-(3-dimethylaminomethylphenyl)-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl]amide (1R,2R)-2 -phenylcyclopropane carboxylic acid Chemical compound 0.000 claims description 125
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 102
• 125000001424 substituent group Chemical group 0.000 claims description 71
• 125000006694 (C2-C10) heterocyclyl group Chemical group 0.000 claims description 65
• 238000002360 preparation method Methods 0.000 claims description 64
• 125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims description 61
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 60
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 53
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 48
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 33
• 229910052731 fluorine Inorganic materials 0.000 claims description 32
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 29
• 229910052801 chlorine Inorganic materials 0.000 claims description 29
• 229910052794 bromium Inorganic materials 0.000 claims description 28
• 239000012453 solvate Substances 0.000 claims description 28
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 26
• 230000000118 anti-neoplastic effect Effects 0.000 claims description 26
• CRSYCFLQNTZJCV-UHFFFAOYSA-N 6-amino-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-9-one Chemical compound C1=2C=3C=NNC(=O)C1=CC(N)=CC=2NC=3C1=CC=CC=C1 CRSYCFLQNTZJCV-UHFFFAOYSA-N 0.000 claims description 24
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• 150000001408 amides Chemical class 0.000 claims description 18
• CHGGMSOIXXKNLD-UHFFFAOYSA-N 6-amino-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-9-one Chemical compound C1=NNC(=O)C2=CC(N)=CC3=C2C1=CN3 CHGGMSOIXXKNLD-UHFFFAOYSA-N 0.000 claims description 16
• 241000124008 Mammalia Species 0.000 claims description 16
• 230000005855 radiation Effects 0.000 claims description 15
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
• 230000002401 inhibitory effect Effects 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 229910052740 iodine Inorganic materials 0.000 claims description 11
• BOBRJSOBPBRADS-UHFFFAOYSA-N 6-amino-2-ethyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-9-one Chemical compound N1C(CC)=C2C=NNC(=O)C3=C2C1=CC(N)=C3 BOBRJSOBPBRADS-UHFFFAOYSA-N 0.000 claims description 10
• 208000035269 cancer or benign tumor Diseases 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 10
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
• CBMISDSKWRMBFB-OAQYLSRUSA-N (2R)-2-amino-2-cyclohexyl-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)acetamide Chemical compound C1([C@@H](N)C(=O)NC=2C=C3C(=O)NN=CC4=C(C=5C=CC=CC=5)NC(=C34)C=2)CCCCC1 CBMISDSKWRMBFB-OAQYLSRUSA-N 0.000 claims description 8
• CZLDSCXHCDKQFT-UHFFFAOYSA-N 2-fluoro-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)-3-(trifluoromethyl)benzamide Chemical compound C1=CC=C(C(F)(F)F)C(F)=C1C(=O)NC1=CC(NC(C=2C=CC=CC=2)=C2C=NNC3=O)=C2C3=C1 CZLDSCXHCDKQFT-UHFFFAOYSA-N 0.000 claims description 8
• WQUBEIMCFHCJCO-AWCRTANDSA-N 4-amino-n-{4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-1-isobutyl-5-phenyl-pentyl}-benzamide Chemical compound C([C@@H]([C@@H](O)C[C@H](CC(C)C)NC(=O)C=1C=C(N)C=CC=1)NC(=O)COC=1C(=CC=CC=1C)C)C1=CC=CC=C1 WQUBEIMCFHCJCO-AWCRTANDSA-N 0.000 claims description 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
• GMKWPGWMJVVGMR-UHFFFAOYSA-N N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)-4-thiophen-2-ylbutanamide Chemical compound C=1C(=C23)NC(C=4C=CC=CC=4)=C3C=NNC(=O)C2=CC=1NC(=O)CCCC1=CC=CS1 GMKWPGWMJVVGMR-UHFFFAOYSA-N 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• VWJCDWQVWASWJL-ZWKOTPCHSA-N (1R,2R)-N-(9-oxo-2-pyridin-3-yl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](C1)C=1C=CC=CC=1)NC(C=C1C(=O)NN=CC=2C=31)=CC=3NC=2C1=CC=CN=C1 VWJCDWQVWASWJL-ZWKOTPCHSA-N 0.000 claims description 6
• NFXMJZRICBRUKE-UHFFFAOYSA-N 2-(3,4-dihydro-1H-isoquinolin-2-yl)-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)acetamide Chemical compound C1CC2=CC=CC=C2CN1CC(=O)NC(C=C1C(=O)NN=CC=2C=31)=CC=3NC=2C1=CC=CC=C1 NFXMJZRICBRUKE-UHFFFAOYSA-N 0.000 claims description 6
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 6
• SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 claims description 5
• AGSJKWXDOAYRNN-ZWKOTPCHSA-N (1R,2R)-N-(9-oxo-2-pyridin-4-yl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](C1)C=1C=CC=CC=1)NC(C=C1C(=O)NN=CC=2C=31)=CC=3NC=2C1=CC=NC=C1 AGSJKWXDOAYRNN-ZWKOTPCHSA-N 0.000 claims description 4
• TWYJYUIFEPPLLC-ZMBIFBSDSA-N (2R)-2-amino-2-(4-hydroxyphenyl)-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)acetamide hydrochloride Chemical compound Cl.O=C([C@H](N)C=1C=CC(O)=CC=1)NC(C=C1C(=O)NN=CC=2C=31)=CC=3NC=2C1=CC=CC=C1 TWYJYUIFEPPLLC-ZMBIFBSDSA-N 0.000 claims description 4
• YYGGXZXUNVOQQE-HXUWFJFHSA-N (2R)-2-amino-2-cyclohexyl-N-[2-[3-(methylamino)prop-1-ynyl]-9-oxo-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl]acetamide Chemical compound C1([C@@H](N)C(=O)NC=2C=C3NC(=C4C3=C(C(NN=C4)=O)C=2)C#CCNC)CCCCC1 YYGGXZXUNVOQQE-HXUWFJFHSA-N 0.000 claims description 4
• DPKSIAPPUDIZGD-JOCHJYFZSA-N (2R)-2-hydroxy-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)-2-phenylacetamide Chemical compound O=C([C@H](O)C=1C=CC=CC=1)NC(C=C1C(=O)NN=CC=2C=31)=CC=3NC=2C1=CC=CC=C1 DPKSIAPPUDIZGD-JOCHJYFZSA-N 0.000 claims description 4
• VITIFWNDQJDHNJ-QGZVFWFLSA-N (2R)-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)piperidine-2-carboxamide Chemical compound O=C([C@@H]1NCCCC1)NC(C=C1C(=O)NN=CC=2C=31)=CC=3NC=2C1=CC=CC=C1 VITIFWNDQJDHNJ-QGZVFWFLSA-N 0.000 claims description 4
• DQCWXAWRJUKYAS-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-yl)-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)acetamide Chemical compound C1C2=CC=CC=C2CC1CC(=O)NC(C=C1C(=O)NN=CC=2C=31)=CC=3NC=2C1=CC=CC=C1 DQCWXAWRJUKYAS-UHFFFAOYSA-N 0.000 claims description 4
• PZPSDFSECCUDTC-UHFFFAOYSA-N 3-fluoro-2-methyl-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)benzamide Chemical compound CC1=C(F)C=CC=C1C(=O)NC1=CC(NC(C=2C=CC=CC=2)=C2C=NNC3=O)=C2C3=C1 PZPSDFSECCUDTC-UHFFFAOYSA-N 0.000 claims description 4
• GJPXCWIXYLXMOB-UHFFFAOYSA-N 6-amino-9-oxo-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaene-2-carbonitrile Chemical compound Nc1cc2[nH]c(C#N)c3cn[nH]c(=O)c(c1)c23 GJPXCWIXYLXMOB-UHFFFAOYSA-N 0.000 claims description 4
• PYBVOEZXMNJRMK-UHFFFAOYSA-N N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)-2-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)NC1=CC(NC(C=2C=CC=CC=2)=C2C=NNC3=O)=C2C3=C1 PYBVOEZXMNJRMK-UHFFFAOYSA-N 0.000 claims description 4
• SOXNMWXZIMFNRZ-UHFFFAOYSA-N N-[2-[3-[(dimethylamino)methyl]phenyl]-9-oxo-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl]-2-fluoro-3-(trifluoromethyl)benzamide Chemical compound CN(C)CC1=CC=CC(C2=C3C4=C(C(NN=C3)=O)C=C(NC(=O)C=3C(=C(C=CC=3)C(F)(F)F)F)C=C4N2)=C1 SOXNMWXZIMFNRZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
• CCSIOWCWLDQOEJ-OAQYLSRUSA-N (2R)-2-amino-2-(4-hydroxyphenyl)-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)acetamide Chemical compound O=C([C@H](N)C=1C=CC(O)=CC=1)NC(C=C1C(=O)NN=CC=2C=31)=CC=3NC=2C1=CC=CC=C1 CCSIOWCWLDQOEJ-OAQYLSRUSA-N 0.000 claims description 2
• AHRFABYUKRWAOZ-ZMBIFBSDSA-N (2R)-2-amino-2-cyclohexyl-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)acetamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1([C@@H](N)C(=O)NC=2C=C3C(=O)NN=CC4=C(C=5C=CC=CC=5)NC(=C34)C=2)CCCCC1 AHRFABYUKRWAOZ-ZMBIFBSDSA-N 0.000 claims description 2
• VLDYABHEVXJJLD-OAQYLSRUSA-N (2R)-2-amino-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)-2-phenylacetamide Chemical compound O=C([C@H](N)C=1C=CC=CC=1)NC(C=C1C(=O)NN=CC=2C=31)=CC=3NC=2C1=CC=CC=C1 VLDYABHEVXJJLD-OAQYLSRUSA-N 0.000 claims description 2
• VQRXBGRDQVEAFV-HXUWFJFHSA-N (2R)-2-amino-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)-3-phenylpropanamide Chemical compound C([C@@H](N)C(=O)NC=1C=C2C(=O)NN=CC3=C(C=4C=CC=CC=4)NC(=C23)C=1)C1=CC=CC=C1 VQRXBGRDQVEAFV-HXUWFJFHSA-N 0.000 claims description 2
• KAUOHOGBMDOVSK-JOCHJYFZSA-N (2R)-3-(4-hydroxyphenyl)-2-(methylamino)-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)propanamide Chemical compound C([C@@H](NC)C(=O)NC=1C=C2C(=O)NN=CC3=C(C=4C=CC=CC=4)NC(=C23)C=1)C1=CC=C(O)C=C1 KAUOHOGBMDOVSK-JOCHJYFZSA-N 0.000 claims description 2
• BQWYCFJIZBUBFX-UHFFFAOYSA-N 1-acetyl-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)piperidine-4-carboxamide Chemical compound C1CN(C(=O)C)CCC1C(=O)NC1=CC(NC(C=2C=CC=CC=2)=C2C=NNC3=O)=C2C3=C1 BQWYCFJIZBUBFX-UHFFFAOYSA-N 0.000 claims description 2
• WUEPMEXUMQVEGN-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;2,2,2-trifluoro-n-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(=O)NCCNCCNC(=O)C(F)(F)F WUEPMEXUMQVEGN-UHFFFAOYSA-N 0.000 claims description 2
• NLACXWLLGSREFR-UHFFFAOYSA-N 2,3-difluoro-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=C3C(=O)NN=CC4=C(C=5C=CC=CC=5)NC(=C34)C=2)=C1F NLACXWLLGSREFR-UHFFFAOYSA-N 0.000 claims description 2
• PJAKNKJLTGSWTL-UHFFFAOYSA-N 2-(3-chlorophenyl)-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)acetamide Chemical compound ClC1=CC=CC(CC(=O)NC=2C=C3C(=O)NN=CC4=C(C=5C=CC=CC=5)NC(=C34)C=2)=C1 PJAKNKJLTGSWTL-UHFFFAOYSA-N 0.000 claims description 2
• DCKHISWFPXBWQG-UHFFFAOYSA-N 2-cyclohexyl-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)acetamide Chemical compound C=1C(=C23)NC(C=4C=CC=CC=4)=C3C=NNC(=O)C2=CC=1NC(=O)CC1CCCCC1 DCKHISWFPXBWQG-UHFFFAOYSA-N 0.000 claims description 2
• LFWZIYXJGBCGSY-UHFFFAOYSA-N 2-ethylsulfanyl-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)pyridine-3-carboxamide Chemical compound CCSC1=NC=CC=C1C(=O)NC1=CC(NC(C=2C=CC=CC=2)=C2C=NNC3=O)=C2C3=C1 LFWZIYXJGBCGSY-UHFFFAOYSA-N 0.000 claims description 2
• JDBKWCJYBZAJQF-UHFFFAOYSA-N 3-(2-methylphenyl)-N-(9-oxo-2-phenyl-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-6-yl)propanamide Chemical compound CC1=CC=CC=C1CCC(=O)NC1=CC(NC(C=2C=CC=CC=2)=C2C=NNC3=O)=C2C3=C1 JDBKWCJYBZAJQF-UHFFFAOYSA-N 0.000 claims description 2
• RKALKJBJXGHOLL-UHFFFAOYSA-N 6-amino-2-[(dimethylamino)methyl]-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-9-one Chemical compound CN(C)Cc1[nH]c2cc(N)cc3c2c1cn[nH]c3=O RKALKJBJXGHOLL-UHFFFAOYSA-N 0.000 claims description 2
• SAQQSGJIBBKFIB-UHFFFAOYSA-N 6-amino-2-[3-(methylamino)prop-1-ynyl]-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-9-one Chemical compound CNCC#Cc1[nH]c2cc(N)cc3c2c1cn[nH]c3=O SAQQSGJIBBKFIB-UHFFFAOYSA-N 0.000 claims description 2
• OBHVRQRJONHVOF-UHFFFAOYSA-N 6-amino-2-bromo-3,10,11-triazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13),11-pentaen-9-one Chemical compound C1=NNC(=O)C2=CC(N)=CC3=C2C1=C(Br)N3 OBHVRQRJONHVOF-UHFFFAOYSA-N 0.000 claims description 2
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