AU2010326727B2 - Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases - Google Patents
Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases Download PDFInfo
- Publication number
- AU2010326727B2 AU2010326727B2 AU2010326727A AU2010326727A AU2010326727B2 AU 2010326727 B2 AU2010326727 B2 AU 2010326727B2 AU 2010326727 A AU2010326727 A AU 2010326727A AU 2010326727 A AU2010326727 A AU 2010326727A AU 2010326727 B2 AU2010326727 B2 AU 2010326727B2
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- amino
- sulfonyl
- benzamide
- chlorophenyl
- 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.)
- Ceased
Links
- 206010028980 Neoplasm Diseases 0.000 title claims description 16
- 201000011510 cancer Diseases 0.000 title claims description 11
- 208000023275 Autoimmune disease Diseases 0.000 title description 3
- 208000026278 immune system disease Diseases 0.000 title description 3
- 230000006907 apoptotic process Effects 0.000 title 1
- 230000001939 inductive effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 968
- -1 4-fluorotetrahydro-2H-pyran-4-yl Chemical group 0.000 claims description 653
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 388
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 216
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 169
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 140
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 92
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 53
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 33
- 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 description 23
- 239000003814 drug Substances 0.000 claims description 21
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 14
- 201000000050 myeloid neoplasm Diseases 0.000 claims description 14
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 13
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 13
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 13
- 208000003747 lymphoid leukemia Diseases 0.000 claims description 12
- 206010005003 Bladder cancer Diseases 0.000 claims description 11
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 11
- 206010006187 Breast cancer Diseases 0.000 claims description 11
- 208000026310 Breast neoplasm Diseases 0.000 claims description 11
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 11
- 206010009944 Colon cancer Diseases 0.000 claims description 11
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 11
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 11
- 208000003445 Mouth Neoplasms Diseases 0.000 claims description 11
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 11
- 206010033128 Ovarian cancer Diseases 0.000 claims description 11
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 11
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 11
- 206010060862 Prostate cancer Diseases 0.000 claims description 11
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 11
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 11
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 11
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 11
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 11
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 11
- 201000010881 cervical cancer Diseases 0.000 claims description 11
- 201000004101 esophageal cancer Diseases 0.000 claims description 11
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 11
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims description 11
- 208000014018 liver neoplasm Diseases 0.000 claims description 11
- 230000036210 malignancy Effects 0.000 claims description 11
- 201000001441 melanoma Diseases 0.000 claims description 11
- 208000025113 myeloid leukemia Diseases 0.000 claims description 11
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 11
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 11
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 11
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 11
- 208000000277 Splenic Neoplasms Diseases 0.000 claims description 10
- 201000006491 bone marrow cancer Diseases 0.000 claims description 10
- 201000003444 follicular lymphoma Diseases 0.000 claims description 10
- 201000002471 spleen cancer Diseases 0.000 claims description 10
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims 1
- 108010090931 Proto-Oncogene Proteins c-bcl-2 Proteins 0.000 abstract description 12
- 102000013535 Proto-Oncogene Proteins c-bcl-2 Human genes 0.000 abstract description 12
- 230000002424 anti-apoptotic effect Effects 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
- 201000010099 disease Diseases 0.000 abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 519
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 437
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 437
- 150000001925 cycloalkenes Chemical class 0.000 description 171
- 150000002390 heteroarenes Chemical class 0.000 description 169
- 150000001924 cycloalkanes Chemical class 0.000 description 163
- 239000000460 chlorine Substances 0.000 description 112
- 125000000753 cycloalkyl group Chemical group 0.000 description 109
- 229910052801 chlorine Inorganic materials 0.000 description 108
- 229910052731 fluorine Inorganic materials 0.000 description 108
- 229910052794 bromium Inorganic materials 0.000 description 107
- 229910052740 iodine Inorganic materials 0.000 description 106
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 97
- 125000000217 alkyl group Chemical group 0.000 description 92
- 229910004013 NO 2 Inorganic materials 0.000 description 91
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 89
- 101150009274 nhr-1 gene Proteins 0.000 description 80
- 125000003342 alkenyl group Chemical group 0.000 description 71
- 125000000392 cycloalkenyl group Chemical group 0.000 description 67
- 125000001072 heteroaryl group Chemical group 0.000 description 65
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 61
- 229910052739 hydrogen Inorganic materials 0.000 description 54
- OTXBWGUYZNKPMG-UHFFFAOYSA-N isofulminic acid Chemical compound O[N+]#[C-] OTXBWGUYZNKPMG-UHFFFAOYSA-N 0.000 description 52
- 125000000304 alkynyl group Chemical group 0.000 description 50
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 44
- 229910052757 nitrogen Inorganic materials 0.000 description 41
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 39
- 229940002612 prodrug Drugs 0.000 description 37
- 239000000651 prodrug Substances 0.000 description 37
- 125000004429 atom Chemical group 0.000 description 33
- 125000004432 carbon atom Chemical group C* 0.000 description 26
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 24
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 20
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 18
- 125000002757 morpholinyl group Chemical group 0.000 description 16
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 description 15
- 239000002207 metabolite Substances 0.000 description 15
- 229910052717 sulfur Inorganic materials 0.000 description 15
- 125000004122 cyclic group Chemical group 0.000 description 14
- 125000002950 monocyclic group Chemical group 0.000 description 14
- 101100516561 Caenorhabditis elegans nhr-68 gene Proteins 0.000 description 13
- 125000003386 piperidinyl group Chemical group 0.000 description 13
- 229940079593 drug Drugs 0.000 description 12
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 12
- 125000004957 naphthylene group Chemical group 0.000 description 12
- 125000001422 pyrrolinyl group Chemical group 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 11
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 11
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 description 10
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 10
- 101100516557 Caenorhabditis elegans nhr-62 gene Proteins 0.000 description 9
- VEAUDLLZYJVHRI-UHFFFAOYSA-N Trichlormethine Chemical compound Cl.ClCCN(CCCl)CCCl VEAUDLLZYJVHRI-UHFFFAOYSA-N 0.000 description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 101100516560 Caenorhabditis elegans nhr-67 gene Proteins 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 125000005549 heteroarylene group Chemical group 0.000 description 8
- OMJKVIFSWSQTGQ-UHFFFAOYSA-N 6,7-bis(aziridin-1-yl)quinazoline-5,8-dione Chemical compound C1CN1C=1C(=O)C2=NC=NC=C2C(=O)C=1N1CC1 OMJKVIFSWSQTGQ-UHFFFAOYSA-N 0.000 description 7
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 125000004450 alkenylene group Chemical group 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 description 6
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 description 6
- 101100294121 Caenorhabditis elegans nhr-57 gene Proteins 0.000 description 6
- 102220507282 Rab11 family-interacting protein 1_R27A_mutation Human genes 0.000 description 6
- 102220507264 Rab11 family-interacting protein 1_R29A_mutation Human genes 0.000 description 6
- 125000004419 alkynylene group Chemical group 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 125000005724 cycloalkenylene group Chemical group 0.000 description 6
- 125000002993 cycloalkylene group Chemical group 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 125000006588 heterocycloalkylene group Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229930195734 saturated hydrocarbon Natural products 0.000 description 6
- 101100294108 Caenorhabditis elegans nhr-41 gene Proteins 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 102220497337 14-3-3 protein zeta/delta_R59A_mutation Human genes 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 4
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 description 4
- 102220518322 Casein kinase I isoform gamma-2_R60A_mutation Human genes 0.000 description 4
- 102220473072 Chemerin-like receptor 2_R14Q_mutation Human genes 0.000 description 4
- 102220586235 Chemerin-like receptor 2_R63A_mutation Human genes 0.000 description 4
- 102220586050 Chemerin-like receptor 2_R64A_mutation Human genes 0.000 description 4
- 102220586191 Chemerin-like receptor 2_R65A_mutation Human genes 0.000 description 4
- 102220474817 Chemerin-like receptor 2_R69A_mutation Human genes 0.000 description 4
- 102220503968 Endogenous retrovirus group K member 6 Rec protein_R20A_mutation Human genes 0.000 description 4
- 102220625700 FAD-linked sulfhydryl oxidase ALR_R48A_mutation Human genes 0.000 description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
- 102220507253 Rab11 family-interacting protein 1_R42A_mutation Human genes 0.000 description 4
- 102220470367 Thymosin beta-10_R28A_mutation Human genes 0.000 description 4
- 102220572809 Uridylate-specific endoribonuclease_R25A_mutation Human genes 0.000 description 4
- 102220475445 Vacuolar protein sorting-associated protein 33A_R24A_mutation Human genes 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 4
- 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 0.000 description 4
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- PUPRYKVOWVDCIS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=CC(Cl)=CC=2)=CC=C1NCCCN1CCOCC1 PUPRYKVOWVDCIS-UHFFFAOYSA-N 0.000 description 3
- LYHTVEABEFTCIZ-UHFFFAOYSA-N 2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[4-[(4-morpholin-4-ylcyclohexyl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC=CC=2)OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1NC(CC1)CCC1N1CCOCC1 LYHTVEABEFTCIZ-UHFFFAOYSA-N 0.000 description 3
- MXFOQZLUCVHVRD-UHFFFAOYSA-N 2-methylsulfonyloxyethyl-[2,3,4,5-tetrahydroxy-6-(2-methylsulfonyloxyethylamino)hexyl]azanium;chloride Chemical compound [Cl-].CS(=O)(=O)OCCNCC(O)C(O)C(O)C(O)C[NH2+]CCOS(C)(=O)=O MXFOQZLUCVHVRD-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 102220598631 5-hydroxytryptamine receptor 1E_R49A_mutation Human genes 0.000 description 3
- 102220506029 Adenylyl-sulfate kinase_R40A_mutation Human genes 0.000 description 3
- 101100240518 Caenorhabditis elegans nhr-12 gene Proteins 0.000 description 3
- 102220586055 Chemerin-like receptor 2_R70A_mutation Human genes 0.000 description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
- 102220516986 Double homeobox protein 4_R23A_mutation Human genes 0.000 description 3
- 102220608655 Methyl-CpG-binding domain protein 1_R47A_mutation Human genes 0.000 description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 3
- 102220604339 Protein shisa-4_R43A_mutation Human genes 0.000 description 3
- 102220507255 Rab11 family-interacting protein 1_R39K_mutation Human genes 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 102220470414 Thymosin beta-10_R26A_mutation Human genes 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 229910052805 deuterium Inorganic materials 0.000 description 3
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- GCVFCUPRTZORNH-UHFFFAOYSA-N n,n-dimethyl-3-[4-(1,10-phenanthrolin-4-yl)butoxy]aniline;2-pyridin-2-ylpyridine;ruthenium Chemical compound [Ru].N1=CC=CC=C1C1=CC=CC=N1.N1=CC=CC=C1C1=CC=CC=N1.CN(C)C1=CC=CC(OCCCCC=2C3=C(C4=NC=CC=C4C=C3)N=CC=2)=C1 GCVFCUPRTZORNH-UHFFFAOYSA-N 0.000 description 3
- BFZJREFBBCEROH-UHFFFAOYSA-N n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C=CC=CC=2)=CC=C1NCC1CCOCC1 BFZJREFBBCEROH-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 2
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 2
- WSURVZMJBWPPEV-UHFFFAOYSA-N 2-(2-bromophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)Br)C=C1[N+]([O-])=O WSURVZMJBWPPEV-UHFFFAOYSA-N 0.000 description 2
- ZRSZDZAKYYMDOG-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC(F)=CC=2)Cl)C=C1[N+]([O-])=O ZRSZDZAKYYMDOG-UHFFFAOYSA-N 0.000 description 2
- SREBAAOBARFNMD-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[1-[2-(4-chlorophenyl)phenyl]ethyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C=1C=CC=C(C=2C=CC(Cl)=CC=2)C=1C(C)N(CC1)CCN1C(C=C1OC=2C(=CC=CC=2)Cl)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 SREBAAOBARFNMD-UHFFFAOYSA-N 0.000 description 2
- BEUMSXQACLMJNW-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-(trifluoromethylsulfonyl)phenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)Cl)C=C1S(=O)(=O)C(F)(F)F BEUMSXQACLMJNW-UHFFFAOYSA-N 0.000 description 2
- XQZGZOOZKRXZLK-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)Cl)=CC=C1NCC1CCOCC1 XQZGZOOZKRXZLK-UHFFFAOYSA-N 0.000 description 2
- JHYAFUUOUQVMFQ-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)Cl)=CC=C1NCCCN1CCOCC1 JHYAFUUOUQVMFQ-UHFFFAOYSA-N 0.000 description 2
- BOYLYRKJYWJQKB-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-[3-(dimethylamino)propylamino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1=C([N+]([O-])=O)C(NCCCN(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC=CC=C1Cl BOYLYRKJYWJQKB-UHFFFAOYSA-N 0.000 description 2
- RVGVURSFDHZITP-UHFFFAOYSA-N 2-(3-aminophenoxy)-4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound NC1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NCC3CCOCC3)=CC=2)[N+]([O-])=O)=C1 RVGVURSFDHZITP-UHFFFAOYSA-N 0.000 description 2
- DBKAZDQBIPEOGV-UHFFFAOYSA-N 2-(3-bromophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Br)C=CC=2)C=C1[N+]([O-])=O DBKAZDQBIPEOGV-UHFFFAOYSA-N 0.000 description 2
- GPQCKPDSCZTKAA-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C=CC=2)=CC=C1NCC1CCOCC1 GPQCKPDSCZTKAA-UHFFFAOYSA-N 0.000 description 2
- CGCOBDOAXOWJOD-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C=CC=2)=CC=C1NCCCN1CCOCC1 CGCOBDOAXOWJOD-UHFFFAOYSA-N 0.000 description 2
- KCAHUJYBBGPSIC-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-[3-(dimethylamino)propylamino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1=C([N+]([O-])=O)C(NCCCN(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC=CC(Cl)=C1 KCAHUJYBBGPSIC-UHFFFAOYSA-N 0.000 description 2
- DKSBZPMDKRHXCD-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[4-(4-chlorophenyl)-6,6-dimethyl-2,5-dihydropyran-3-yl]methyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3COC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C=CC=2)C=C1[N+]([O-])=O DKSBZPMDKRHXCD-UHFFFAOYSA-N 0.000 description 2
- AZXAYANTZWHYLK-UHFFFAOYSA-N 2-(4-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=CC(Cl)=CC=2)=CC=C1NCC1CCOCC1 AZXAYANTZWHYLK-UHFFFAOYSA-N 0.000 description 2
- YEIWAVAEKOVCIJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-[3-(dimethylamino)propylamino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1=C([N+]([O-])=O)C(NCCCN(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC=C(Cl)C=C1 YEIWAVAEKOVCIJ-UHFFFAOYSA-N 0.000 description 2
- PCNIJOJMNDQAQX-UHFFFAOYSA-N 2-(6-amino-5-chloropyridin-3-yl)oxy-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-(1,4-dioxan-2-ylmethoxy)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Cl)C(N)=NC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1OCC1COCCO1 PCNIJOJMNDQAQX-UHFFFAOYSA-N 0.000 description 2
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 2
- HOAJPWHTPSJTHV-UHFFFAOYSA-N 2-[(6-fluoro-1H-indol-5-yl)oxy]-N-[3-nitro-4-[[4-[4-(oxan-4-yl)piperazin-1-yl]cyclohexyl]amino]phenyl]sulfonylbenzamide Chemical compound FC1=C(C=C2C=CNC2=C1)OC1=C(C(=O)NS(=O)(=O)C2=CC(=C(C=C2)NC2CCC(CC2)N2CCN(CC2)C2CCOCC2)[N+](=O)[O-])C=CC=C1 HOAJPWHTPSJTHV-UHFFFAOYSA-N 0.000 description 2
- HUAVJMPYTUFNRN-UHFFFAOYSA-N 2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[3-nitro-4-[[4-(oxan-4-ylamino)cyclohexyl]amino]phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC=CC=2)OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1NC(CC1)CCC1NC1CCOCC1 HUAVJMPYTUFNRN-UHFFFAOYSA-N 0.000 description 2
- SMKCFWBTIJEHBH-UHFFFAOYSA-N 2-[(6-fluoro-1h-indol-5-yl)oxy]benzamide Chemical compound NC(=O)C1=CC=CC=C1OC(C(=C1)F)=CC2=C1NC=C2 SMKCFWBTIJEHBH-UHFFFAOYSA-N 0.000 description 2
- XURXKNCRRGRFER-UHFFFAOYSA-N 3-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]benzamide Chemical compound C1C(C)(C)CCC(CN2CCN(CC2)C=2C(=C(C(N)=O)C=CC=2)OC=2C(=CC=3NC=CC=3C=2)F)=C1C1=CC=C(Cl)C=C1 XURXKNCRRGRFER-UHFFFAOYSA-N 0.000 description 2
- 125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 2
- ZRPDBJRWYSBBFN-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2,3-difluorophenoxy)-n-[4-(2-morpholin-4-ylethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=C(F)C=CC=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCN1CCOCC1 ZRPDBJRWYSBBFN-UHFFFAOYSA-N 0.000 description 2
- LHDDUICMCKRJEK-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2,3-difluorophenoxy)-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=C(F)C=CC=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCOCC1 LHDDUICMCKRJEK-UHFFFAOYSA-N 0.000 description 2
- WTKDSAMKGRYZBZ-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2,3-difluorophenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=C(F)C=CC=2)F)C=C1[N+]([O-])=O WTKDSAMKGRYZBZ-UHFFFAOYSA-N 0.000 description 2
- DESPEKQEDGYMPF-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2,3-difluorophenoxy)-n-[4-[[1-(2-fluoroethyl)piperidin-4-yl]amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=C(F)C=CC=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC1CCN(CCF)CC1 DESPEKQEDGYMPF-UHFFFAOYSA-N 0.000 description 2
- YYCPSYXLUCFFKA-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2,5-dichlorophenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=C(Cl)C=2)Cl)C=C1[N+]([O-])=O YYCPSYXLUCFFKA-UHFFFAOYSA-N 0.000 description 2
- DSOKCXNWQCUKIG-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2-fluorophenoxy)-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=CC=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCOCC1 DSOKCXNWQCUKIG-UHFFFAOYSA-N 0.000 description 2
- PDRCAMAVQKGGRS-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2-fluorophenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)F)C=C1[N+]([O-])=O PDRCAMAVQKGGRS-UHFFFAOYSA-N 0.000 description 2
- IWKQZUKHSTZEOH-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2-methoxyphenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound COC1=CC=CC=C1OC1=CC(N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC1CCN(C)CC1 IWKQZUKHSTZEOH-UHFFFAOYSA-N 0.000 description 2
- FFHRCTIMPMTQPK-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2-methylphenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)C)C=C1[N+]([O-])=O FFHRCTIMPMTQPK-UHFFFAOYSA-N 0.000 description 2
- JGJXIUVOYVRLEH-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(3,4-dichlorophenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C(Cl)=CC=2)C=C1[N+]([O-])=O JGJXIUVOYVRLEH-UHFFFAOYSA-N 0.000 description 2
- JDYJMJDGDGXGEE-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(3,5-dichlorophenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C=C(Cl)C=2)C=C1[N+]([O-])=O JDYJMJDGDGXGEE-UHFFFAOYSA-N 0.000 description 2
- SDFDMUACMZSBJA-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(3-fluorophenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(F)C=CC=2)C=C1[N+]([O-])=O SDFDMUACMZSBJA-UHFFFAOYSA-N 0.000 description 2
- TXJZKVMXSRESBL-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(3-methylphenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(C)C=CC=2)C=C1[N+]([O-])=O TXJZKVMXSRESBL-UHFFFAOYSA-N 0.000 description 2
- PKQMBONILLGOGB-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(3-methyl-2h-indazol-4-yl)oxy]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=12C(C)=NNC2=CC=CC=1OC1=CC(N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCOCC1 PKQMBONILLGOGB-UHFFFAOYSA-N 0.000 description 2
- NPQNOIKFAPBOBM-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-4-yl)oxy]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=3C=CNC=3C=C(F)C=2)C=C1[N+]([O-])=O NPQNOIKFAPBOBM-UHFFFAOYSA-N 0.000 description 2
- JOEVLLFEVQWMAN-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[4-[(4-methylpiperazin-1-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCN1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=3NC=CC=3C=2)F)C=C1[N+]([O-])=O JOEVLLFEVQWMAN-UHFFFAOYSA-N 0.000 description 2
- XJKTYLRFRLPIFM-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-(1,4-dioxan-2-ylmethylamino)-3-nitrophenyl]sulfonyl-2-[(6-fluoro-1h-indol-5-yl)oxy]benzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1COCCO1 XJKTYLRFRLPIFM-UHFFFAOYSA-N 0.000 description 2
- XANATGAMHCVCFJ-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-cyclopentylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonyl-2-(2,3-difluorophenoxy)benzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=C(F)C=CC=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CCCC1 XANATGAMHCVCFJ-UHFFFAOYSA-N 0.000 description 2
- ZWWCHSHXRSKHAF-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-cyclopropylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonyl-2-(2,3-difluorophenoxy)benzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=C(F)C=CC=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CC1 ZWWCHSHXRSKHAF-UHFFFAOYSA-N 0.000 description 2
- CGLBRIDBQZVEDF-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-cyclopropylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonyl-2-(2-fluorophenoxy)benzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=CC=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CC1 CGLBRIDBQZVEDF-UHFFFAOYSA-N 0.000 description 2
- YUMBQIKWPGBNMQ-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-cyclopropylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonyl-2-(3-fluorophenoxy)benzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(F)C=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CC1 YUMBQIKWPGBNMQ-UHFFFAOYSA-N 0.000 description 2
- NSZGQMXEWICLQV-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[3-(dimethylamino)propylamino]-3-nitrophenyl]sulfonyl-2-(3-fluorophenoxy)benzamide Chemical compound C1=C([N+]([O-])=O)C(NCCCN(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC=CC(F)=C1 NSZGQMXEWICLQV-UHFFFAOYSA-N 0.000 description 2
- NQFYRHPUCJHAMA-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[3-(dimethylamino)propylamino]-3-nitrophenyl]sulfonyl-2-(4-fluorophenoxy)benzamide Chemical compound C1=C([N+]([O-])=O)C(NCCCN(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC=C(F)C=C1 NQFYRHPUCJHAMA-UHFFFAOYSA-N 0.000 description 2
- OGNYCHOYJFWHQX-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-(4-cyanophenoxy)-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=CC(=CC=2)C#N)=CC=C1NCC1CCOCC1 OGNYCHOYJFWHQX-UHFFFAOYSA-N 0.000 description 2
- ADLAQQUJLCOZFD-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C2SC(C)=NC2=CC=1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCOCC1 ADLAQQUJLCOZFD-UHFFFAOYSA-N 0.000 description 2
- GWEDSUABCBFJQR-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[(2-methyl-1,3-benzothiazol-6-yl)oxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C1=C2SC(C)=NC2=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 GWEDSUABCBFJQR-UHFFFAOYSA-N 0.000 description 2
- AXUDACBZMRXPAD-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[(4-methoxyphenyl)methoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C1=CC(OC)=CC=C1COC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 AXUDACBZMRXPAD-UHFFFAOYSA-N 0.000 description 2
- VJCZNEKJICWQHM-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[2-(dimethylcarbamoyl)phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 VJCZNEKJICWQHM-UHFFFAOYSA-N 0.000 description 2
- MRPDMKKBINQBTE-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[2-[2-(dimethylamino)-2-oxoethyl]phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound CN(C)C(=O)CC1=CC=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 MRPDMKKBINQBTE-UHFFFAOYSA-N 0.000 description 2
- SNHOTWHDGAPHKQ-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[2-[2-(dimethylamino)ethyl]phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound CN(C)CCC1=CC=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 SNHOTWHDGAPHKQ-UHFFFAOYSA-N 0.000 description 2
- MYKHIGRHKBIENV-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[2-[3-(dimethylamino)-3-oxopropyl]phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound CN(C)C(=O)CCC1=CC=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 MYKHIGRHKBIENV-UHFFFAOYSA-N 0.000 description 2
- LXPFXDMUHMUYCP-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[3-(2,4-dimethyl-1,3-thiazol-5-yl)phenoxy]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound S1C(C)=NC(C)=C1C1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NCCCN3CCOCC3)=CC=2)[N+]([O-])=O)=C1 LXPFXDMUHMUYCP-UHFFFAOYSA-N 0.000 description 2
- PRBILEOLCWMOIB-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[3-(ethylaminomethyl)phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound CCNCC1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NCC3CCOCC3)=CC=2)[N+]([O-])=O)=C1 PRBILEOLCWMOIB-UHFFFAOYSA-N 0.000 description 2
- HCTZRKODQWYUGE-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[3-(methylcarbamoyl)phenoxy]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound CNC(=O)C1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NCCCN3CCOCC3)=CC=2)[N+]([O-])=O)=C1 HCTZRKODQWYUGE-UHFFFAOYSA-N 0.000 description 2
- MSAOQUZODVOGFA-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[3-[(dimethylamino)methyl]phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound CN(C)CC1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NCC3CCOCC3)=CC=2)[N+]([O-])=O)=C1 MSAOQUZODVOGFA-UHFFFAOYSA-N 0.000 description 2
- OVIALSXXPNHRHC-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[3-[2-(dimethylamino)ethoxy]phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound CN(C)CCOC1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NCC3CCOCC3)=CC=2)[N+]([O-])=O)=C1 OVIALSXXPNHRHC-UHFFFAOYSA-N 0.000 description 2
- CFIGLQFXRIMZOI-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[4-[(dimethylamino)methyl]phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C1=CC(CN(C)C)=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 CFIGLQFXRIMZOI-UHFFFAOYSA-N 0.000 description 2
- BPXGNQYGSWWVJR-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[4-[2-(dimethylamino)-2-oxoethoxy]phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C1=CC(OCC(=O)N(C)C)=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 BPXGNQYGSWWVJR-UHFFFAOYSA-N 0.000 description 2
- NIFBBACLSOYKBZ-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[4-[2-(dimethylamino)ethyl]phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C1=CC(CCN(C)C)=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 NIFBBACLSOYKBZ-UHFFFAOYSA-N 0.000 description 2
- MFSKLDLKLFAFDF-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[[3-(3-morpholin-4-ylpropyl)-1h-indol-5-yl]oxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=C3C(CCCN4CCOCC4)=CNC3=CC=2)=CC=C1NCC1CCOCC1 MFSKLDLKLFAFDF-UHFFFAOYSA-N 0.000 description 2
- NOFFILAMNKEITG-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[[3-[3-(dimethylamino)propyl]-1h-indol-5-yl]oxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C1=C2C(CCCN(C)C)=CNC2=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 NOFFILAMNKEITG-UHFFFAOYSA-N 0.000 description 2
- BXLPJFGFQMYWKI-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-(2-phenylphenoxy)benzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)C=2C=CC=CC=2)=CC=C1NCC1CCOCC1 BXLPJFGFQMYWKI-UHFFFAOYSA-N 0.000 description 2
- LBMAXJNQTZXIHH-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-(3-nitrophenoxy)benzamide Chemical compound [O-][N+](=O)C1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NCC3CCOCC3)=CC=2)[N+]([O-])=O)=C1 LBMAXJNQTZXIHH-UHFFFAOYSA-N 0.000 description 2
- JHWFCLCTRHBZPT-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-(3-phenylmethoxyphenoxy)benzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(OCC=3C=CC=CC=3)C=CC=2)=CC=C1NCC1CCOCC1 JHWFCLCTRHBZPT-UHFFFAOYSA-N 0.000 description 2
- BRMQGKZSKUVPIA-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-(3-phenylphenoxy)benzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(C=CC=2)C=2C=CC=CC=2)=CC=C1NCC1CCOCC1 BRMQGKZSKUVPIA-UHFFFAOYSA-N 0.000 description 2
- MGKYSNQBRQILBG-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-(4-phenylmethoxyphenoxy)benzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=CC(OCC=3C=CC=CC=3)=CC=2)=CC=C1NCC1CCOCC1 MGKYSNQBRQILBG-UHFFFAOYSA-N 0.000 description 2
- QMCUWDYOAIVMKE-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonyl-2-(3-phenylmethoxyphenoxy)benzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(OCC=3C=CC=CC=3)C=CC=2)=CC=C1NCCCN1CCOCC1 QMCUWDYOAIVMKE-UHFFFAOYSA-N 0.000 description 2
- GHCRUXUJIZLSSS-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonyl-2-(3-pyridin-4-ylphenoxy)benzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(C=CC=2)C=2C=CN=CC=2)=CC=C1NCCCN1CCOCC1 GHCRUXUJIZLSSS-UHFFFAOYSA-N 0.000 description 2
- HQCWGUYCBLPPAT-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonyl-2-(4-phenylmethoxyphenoxy)benzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=CC(OCC=3C=CC=CC=3)=CC=2)=CC=C1NCCCN1CCOCC1 HQCWGUYCBLPPAT-UHFFFAOYSA-N 0.000 description 2
- UKKWZWXZPANFRX-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonyl-2-(4-pyridin-4-ylphenoxy)benzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=CC(=CC=2)C=2C=CN=CC=2)=CC=C1NCCCN1CCOCC1 UKKWZWXZPANFRX-UHFFFAOYSA-N 0.000 description 2
- NPDQAGJTPQJTAB-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-[3-(dimethylamino)propylamino]-3-nitrophenyl]sulfonyl-2-(3-phenylmethoxyphenoxy)benzamide Chemical compound C1=C([N+]([O-])=O)C(NCCCN(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC=CC(OCC=2C=CC=CC=2)=C1 NPDQAGJTPQJTAB-UHFFFAOYSA-N 0.000 description 2
- RTKGTVKXZHDBRI-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-[3-(dimethylamino)propylamino]-3-nitrophenyl]sulfonyl-2-[3-(methylcarbamoyl)phenoxy]benzamide Chemical compound CNC(=O)C1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NCCCN(C)C)=CC=2)[N+]([O-])=O)=C1 RTKGTVKXZHDBRI-UHFFFAOYSA-N 0.000 description 2
- SECABGRQRSUIKF-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-[3-(dimethylamino)propylamino]-3-nitrophenyl]sulfonyl-2-[[3-(3-morpholin-4-yl-3-oxopropyl)-1h-indol-5-yl]oxy]benzamide Chemical compound C1=C([N+]([O-])=O)C(NCCCN(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC=C(NC=C2CCC(=O)N3CCOCC3)C2=C1 SECABGRQRSUIKF-UHFFFAOYSA-N 0.000 description 2
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 2
- 101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 description 2
- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 101000971171 Homo sapiens Apoptosis regulator Bcl-2 Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 102220521661 Ribosome biogenesis protein NSA2 homolog_R71A_mutation Human genes 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000006317 cyclopropyl amino group Chemical group 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000000532 dioxanyl group Chemical group 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
- 230000000155 isotopic effect Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 2
- BHLHFLZCAWDBKS-UHFFFAOYSA-N n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C=CC=CC=2)=CC=C1NCCCN1CCOCC1 BHLHFLZCAWDBKS-UHFFFAOYSA-N 0.000 description 2
- FDLQSMDEYKZDSP-UHFFFAOYSA-N n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C=CC=CC=2)C=C1[N+]([O-])=O FDLQSMDEYKZDSP-UHFFFAOYSA-N 0.000 description 2
- LBYCVZLEVNMKMZ-UHFFFAOYSA-N n-[5-ethynyl-6-(oxan-4-ylmethoxy)pyridin-3-yl]sulfonyl-2-[(6-fluoro-1h-indol-5-yl)oxy]benzamide Chemical compound FC1=CC=2NC=CC=2C=C1OC1=CC=CC=C1C(=O)NS(=O)(=O)C(C=C1C#C)=CN=C1OCC1CCOCC1 LBYCVZLEVNMKMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 235000005152 nicotinamide Nutrition 0.000 description 2
- 239000011570 nicotinamide Substances 0.000 description 2
- 229960003966 nicotinamide Drugs 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 125000003566 oxetanyl group Chemical group 0.000 description 2
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- MWVJXHVMBZIHOT-UHFFFAOYSA-N tert-butyl n-[4-[5-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylcarbamoyl]phenoxy]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 MWVJXHVMBZIHOT-UHFFFAOYSA-N 0.000 description 2
- OINNEKFOBWWTFT-UHFFFAOYSA-N tert-butyl n-[[3-[5-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylcarbamoyl]phenoxy]phenyl]methyl]-n-ethylcarbamate Chemical compound CC(C)(C)OC(=O)N(CC)CC1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NCC3CCOCC3)=CC=2)[N+]([O-])=O)=C1 OINNEKFOBWWTFT-UHFFFAOYSA-N 0.000 description 2
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 2
- 125000005455 trithianyl group Chemical group 0.000 description 2
- YJEVAUSLDPCMNO-UHFFFAOYSA-N 1,6-dihydropentalene Chemical compound C1C=CC2=C1CC=C2 YJEVAUSLDPCMNO-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000003562 2,2-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- 125000003660 2,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- OSUKZGNSPHZXJN-UHFFFAOYSA-N 2-(2,3-difluorophenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC=CC=2)OC=2C(=C(F)C=CC=2)F)C=C1[N+]([O-])=O OSUKZGNSPHZXJN-UHFFFAOYSA-N 0.000 description 1
- IEFJYLADWSVUQA-UHFFFAOYSA-N 2-(2,3-difluorophenoxy)-n-[4-[(4-methylpiperazin-1-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCN1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC=CC=2)OC=2C(=C(F)C=CC=2)F)C=C1[N+]([O-])=O IEFJYLADWSVUQA-UHFFFAOYSA-N 0.000 description 1
- WXYGKYZQVDDFIJ-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-[[1-(oxan-4-yl)piperidin-4-yl]amino]phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=CC=2F)Cl)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CCOCC1 WXYGKYZQVDDFIJ-UHFFFAOYSA-N 0.000 description 1
- AYWAJRGONJEFHW-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[1-[2-(4-chlorophenyl)phenyl]ethyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=CC=C(C=2C=CC(Cl)=CC=2)C=1C(C)N(CC1)CCN1C(C=C1OC=2C(=CC=CC=2)Cl)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC1CCN(C)CC1 AYWAJRGONJEFHW-UHFFFAOYSA-N 0.000 description 1
- AXKVBATZWNGBIV-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-[(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]phenyl]sulfonylbenzamide Chemical compound C1C(C)(C)N(C)C(C)(C)CC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)Cl)C=C1[N+]([O-])=O AXKVBATZWNGBIV-UHFFFAOYSA-N 0.000 description 1
- WWMRKVILIDOUEB-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-[(1-propan-2-ylpiperidin-4-yl)amino]phenyl]sulfonylbenzamide Chemical compound C1CN(C(C)C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)Cl)C=C1[N+]([O-])=O WWMRKVILIDOUEB-UHFFFAOYSA-N 0.000 description 1
- KMKVOTAKIPPJHO-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=CC=2)Cl)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCOCC1 KMKVOTAKIPPJHO-UHFFFAOYSA-N 0.000 description 1
- GZTLWGJQUKCSBU-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-cyclopentylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=CC=2)Cl)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CCCC1 GZTLWGJQUKCSBU-UHFFFAOYSA-N 0.000 description 1
- KUOSOOQEKILFFK-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-cyclopropylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=CC=2)Cl)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CC1 KUOSOOQEKILFFK-UHFFFAOYSA-N 0.000 description 1
- UFQDCOHRBYPDMC-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-ethylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(CC)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)Cl)C=C1[N+]([O-])=O UFQDCOHRBYPDMC-UHFFFAOYSA-N 0.000 description 1
- LQQHVPMJVMWKHR-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclopenten-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)Cl)C=C1[N+]([O-])=O LQQHVPMJVMWKHR-UHFFFAOYSA-N 0.000 description 1
- INGVYUGKKHWQHN-UHFFFAOYSA-N 2-(2-chlorophenoxy)-4-[4-[[4-(4-chlorophenyl)-6,6-dimethyl-2,5-dihydropyran-3-yl]methyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3COC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=CC=2)Cl)C=C1[N+]([O-])=O INGVYUGKKHWQHN-UHFFFAOYSA-N 0.000 description 1
- FMVSRXGETZOGCF-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-[(1-propan-2-ylpiperidin-4-yl)amino]phenyl]sulfonylbenzamide Chemical compound C1CN(C(C)C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C=CC=2)C=C1[N+]([O-])=O FMVSRXGETZOGCF-UHFFFAOYSA-N 0.000 description 1
- VVUIIGFUKPTYGY-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-(2-morpholin-4-ylethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Cl)C=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCN1CCOCC1 VVUIIGFUKPTYGY-UHFFFAOYSA-N 0.000 description 1
- AYQIXHUOFUKTMW-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Cl)C=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCOCC1 AYQIXHUOFUKTMW-UHFFFAOYSA-N 0.000 description 1
- VPBUUHQAGNSKMO-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-cyclopentylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Cl)C=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CCCC1 VPBUUHQAGNSKMO-UHFFFAOYSA-N 0.000 description 1
- VOARCKBFFLKLHA-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(4-methylpiperazin-1-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCN1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C=CC=2)C=C1[N+]([O-])=O VOARCKBFFLKLHA-UHFFFAOYSA-N 0.000 description 1
- SLQMAACJVUBOLV-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[3-(dimethylamino)propylamino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1=C([N+]([O-])=O)C(NCCCN(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC=CC(Cl)=C1 SLQMAACJVUBOLV-UHFFFAOYSA-N 0.000 description 1
- BUHXVQINRDNBIZ-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[[1-(2-morpholin-4-ylethyl)piperidin-4-yl]amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Cl)C=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1CCN1CCOCC1 BUHXVQINRDNBIZ-UHFFFAOYSA-N 0.000 description 1
- PMINCQYESRJIDQ-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[[1-(cyclopropylmethyl)piperidin-4-yl]amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Cl)C=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1CC1CC1 PMINCQYESRJIDQ-UHFFFAOYSA-N 0.000 description 1
- GDPNFIRVRCMZKJ-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[[1-[2-(dimethylamino)-2-oxoethyl]piperidin-4-yl]amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(CC(=O)N(C)C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C=CC=2)C=C1[N+]([O-])=O GDPNFIRVRCMZKJ-UHFFFAOYSA-N 0.000 description 1
- RCRBNQFJQSXLFX-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[[4-(diethylamino)cyclohexyl]amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CC(N(CC)CC)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C=CC=2)C=C1[N+]([O-])=O RCRBNQFJQSXLFX-UHFFFAOYSA-N 0.000 description 1
- RFCKKCWXUBGYTF-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[[4-(dimethylamino)cyclohexyl]amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CC(N(C)C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C=CC=2)C=C1[N+]([O-])=O RFCKKCWXUBGYTF-UHFFFAOYSA-N 0.000 description 1
- FRDJSMNTLGNGLR-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-5-(2-pyrrolidin-1-ylethyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=C(CCN4CCCC4)C=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C=CC=2)=CC=C1NCC1CCOCC1 FRDJSMNTLGNGLR-UHFFFAOYSA-N 0.000 description 1
- DFNUARNZOOSDCG-UHFFFAOYSA-N 2-(3-chlorophenoxy)-4-[4-[[4-(4-chlorophenyl)-6,6-dimethyl-2,5-dihydropyran-3-yl]methyl]piperazin-1-yl]-n-[4-[(4-methylpiperazin-1-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCN1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3COC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C=CC=2)C=C1[N+]([O-])=O DFNUARNZOOSDCG-UHFFFAOYSA-N 0.000 description 1
- CDVWMDPYYMXWHV-UHFFFAOYSA-N 2-(3-iodophenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC=CC=2)OC=2C=C(I)C=CC=2)C=C1[N+]([O-])=O CDVWMDPYYMXWHV-UHFFFAOYSA-N 0.000 description 1
- VFGMVAYWKXSHMK-UHFFFAOYSA-N 2-(4-amino-3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Cl)C(N)=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCOCC1 VFGMVAYWKXSHMK-UHFFFAOYSA-N 0.000 description 1
- SZGVKZVZARHZQT-UHFFFAOYSA-N 2-(4-amino-3-chlorophenoxy)-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(Cl)C(N)=CC=2)C=C1[N+]([O-])=O SZGVKZVZARHZQT-UHFFFAOYSA-N 0.000 description 1
- IUVGTMVWFCZRNT-UHFFFAOYSA-N 2-(4-aminophenoxy)-4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C1=CC(N)=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 IUVGTMVWFCZRNT-UHFFFAOYSA-N 0.000 description 1
- WGROXGHNUVUPMN-UHFFFAOYSA-N 2-(5-aminopyridin-3-yl)oxy-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(N)C=NC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 WGROXGHNUVUPMN-UHFFFAOYSA-N 0.000 description 1
- IIRYSMKOWIBMRW-UHFFFAOYSA-N 2-(6-amino-5-bromopyridin-3-yl)oxy-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-(1,4-dioxan-2-ylmethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Br)C(N)=NC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1COCCO1 IIRYSMKOWIBMRW-UHFFFAOYSA-N 0.000 description 1
- ATFRAPMNMWJHAH-UHFFFAOYSA-N 2-(6-amino-5-chloropyridin-3-yl)oxy-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxolan-3-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Cl)C(N)=NC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOC1 ATFRAPMNMWJHAH-UHFFFAOYSA-N 0.000 description 1
- KGUXCZYCMLBTGT-UHFFFAOYSA-N 2-(6-amino-5-chloropyridin-3-yl)oxy-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-(1,4-dioxan-2-ylmethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Cl)C(N)=NC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1COCCO1 KGUXCZYCMLBTGT-UHFFFAOYSA-N 0.000 description 1
- DDXDYVPPATUKQR-UHFFFAOYSA-N 2-(6-aminopyridin-3-yl)oxy-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=NC(N)=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 DDXDYVPPATUKQR-UHFFFAOYSA-N 0.000 description 1
- ZBAQFCMHSJJENN-UHFFFAOYSA-N 2-(6-aminopyridin-3-yl)oxy-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-[[1-(oxan-4-yl)piperidin-4-yl]amino]phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=NC(N)=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CCOCC1 ZBAQFCMHSJJENN-UHFFFAOYSA-N 0.000 description 1
- YFZFZCGOIRDADE-UHFFFAOYSA-N 2-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C3SC(N)=NC3=CC=2)C=C1[N+]([O-])=O YFZFZCGOIRDADE-UHFFFAOYSA-N 0.000 description 1
- NYABBLWESZVFFM-UHFFFAOYSA-N 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OCC=2N=C(N)SC=2)C=C1[N+]([O-])=O NYABBLWESZVFFM-UHFFFAOYSA-N 0.000 description 1
- YVRDIUJGGBRKJO-UHFFFAOYSA-N 2-[(2-oxo-1,3-dihydroindol-4-yl)oxy]benzamide Chemical compound O=C1NC2=CC=CC(=C2C1)OC1=C(C(=O)N)C=CC=C1 YVRDIUJGGBRKJO-UHFFFAOYSA-N 0.000 description 1
- PWJLVGVBQSFROP-UHFFFAOYSA-N 2-[(6,7-difluoro-1H-indol-5-yl)oxy]-N-[4-[(4-morpholin-4-ylcyclohexyl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound FC1=C(C=C2C=CNC2=C1F)OC1=C(C(=O)NS(=O)(=O)C2=CC(=C(C=C2)NC2CCC(CC2)N2CCOCC2)[N+](=O)[O-])C=CC=C1 PWJLVGVBQSFROP-UHFFFAOYSA-N 0.000 description 1
- JEQKKQNMXMYVJJ-UHFFFAOYSA-N 2-[(6-chloro-1h-indol-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-(1,4-dioxan-2-ylmethoxy)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)Cl)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1OCC1COCCO1 JEQKKQNMXMYVJJ-UHFFFAOYSA-N 0.000 description 1
- RRYGPCXBWCOPMJ-UHFFFAOYSA-N 2-[(6-chloro-1h-indol-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-(1,4-dioxan-2-ylmethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)Cl)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1COCCO1 RRYGPCXBWCOPMJ-UHFFFAOYSA-N 0.000 description 1
- MIIGFLOAHPEXAQ-UHFFFAOYSA-N 2-[(6-chloro-1h-indol-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(4-methylpiperazin-1-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCN1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=3NC=CC=3C=2)Cl)C=C1[N+]([O-])=O MIIGFLOAHPEXAQ-UHFFFAOYSA-N 0.000 description 1
- HAFUQLKWFYRLOR-UHFFFAOYSA-N 2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC=CC=2)OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1NCC1CCOCC1 HAFUQLKWFYRLOR-UHFFFAOYSA-N 0.000 description 1
- QXLOSFWLOZYMOO-UHFFFAOYSA-N 2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[4-[(4-fluorooxan-4-yl)methoxy]-3-nitrophenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC=CC=2)OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1OCC1(F)CCOCC1 QXLOSFWLOZYMOO-UHFFFAOYSA-N 0.000 description 1
- FYAPAHGELGSKKV-UHFFFAOYSA-N 2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[4-[(4-methylpiperazin-1-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCN1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC=CC=2)OC=2C(=CC=3NC=CC=3C=2)F)C=C1[N+]([O-])=O FYAPAHGELGSKKV-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- AKWZZLMFWQFLGA-UHFFFAOYSA-N 3-[4-[[4-(dicyclopropylamino)cyclohexyl]amino]-3-nitrophenyl]sulfonyl-2-[(6-fluoro-1H-indol-5-yl)oxy]benzamide Chemical compound C1(CC1)N(C1CCC(CC1)NC1=C(C=C(C=C1)S(=O)(=O)C=1C(=C(C(=O)N)C=CC1)OC=1C=C2C=CNC2=CC1F)[N+](=O)[O-])C1CC1 AKWZZLMFWQFLGA-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- JRBAQAMOIBHJRP-UHFFFAOYSA-N 4,5,6,7-tetrahydro-3ah-indene Chemical group C1CCCC2=CC=CC21 JRBAQAMOIBHJRP-UHFFFAOYSA-N 0.000 description 1
- GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 description 1
- AUYKPNUIDBOGSJ-UHFFFAOYSA-N 4-[4-[1-[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]ethyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1C(C)N(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 AUYKPNUIDBOGSJ-UHFFFAOYSA-N 0.000 description 1
- UCMCYXLHZVKZKQ-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2,3-dichlorophenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=C(Cl)C=CC=2)Cl)C=C1[N+]([O-])=O UCMCYXLHZVKZKQ-UHFFFAOYSA-N 0.000 description 1
- YBLSPBYZIBHERU-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2,3-difluorophenoxy)-n-[3-nitro-4-[[1-(oxan-4-yl)piperidin-4-yl]amino]phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=C(F)C=CC=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CCOCC1 YBLSPBYZIBHERU-UHFFFAOYSA-N 0.000 description 1
- UXVGPIPSPTWEJQ-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2,3-difluorophenoxy)-n-[4-[(1-methylpiperidin-4-yl)methylamino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1CNC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=C(F)C=CC=2)F)C=C1[N+]([O-])=O UXVGPIPSPTWEJQ-UHFFFAOYSA-N 0.000 description 1
- BHKWLOZUFJZREO-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2,5-dichlorophenoxy)-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=C(Cl)C=2)Cl)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCOCC1 BHKWLOZUFJZREO-UHFFFAOYSA-N 0.000 description 1
- PNYDGZJNRYPTNY-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2-fluorophenoxy)-n-[3-nitro-4-[[1-(oxan-4-yl)piperidin-4-yl]amino]phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=CC=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CCOCC1 PNYDGZJNRYPTNY-UHFFFAOYSA-N 0.000 description 1
- MOZKIBRJBOUYEF-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(2-fluorophenoxy)-n-[4-(2-morpholin-4-ylethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=CC=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCN1CCOCC1 MOZKIBRJBOUYEF-UHFFFAOYSA-N 0.000 description 1
- MAVGZBDRHKUVID-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(3-fluorophenoxy)-n-[3-nitro-4-[[1-(oxan-4-yl)piperidin-4-yl]amino]phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(F)C=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(CC1)CCN1C1CCOCC1 MAVGZBDRHKUVID-UHFFFAOYSA-N 0.000 description 1
- BKBNCJRKLJICNI-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(3-fluorophenoxy)-n-[4-(2-morpholin-4-ylethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(F)C=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCN1CCOCC1 BKBNCJRKLJICNI-UHFFFAOYSA-N 0.000 description 1
- QLUVULHNKYGZEM-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(3-fluorophenoxy)-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(F)C=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCOCC1 QLUVULHNKYGZEM-UHFFFAOYSA-N 0.000 description 1
- IUJCHTBPLWDSCP-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(3-hydroxy-2-methylphenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=C(O)C=CC=2)C)C=C1[N+]([O-])=O IUJCHTBPLWDSCP-UHFFFAOYSA-N 0.000 description 1
- ZGAHLFBYZGUOJA-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(3-hydroxyphenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(O)C=CC=2)C=C1[N+]([O-])=O ZGAHLFBYZGUOJA-UHFFFAOYSA-N 0.000 description 1
- SAZVZHLHOFBCAR-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(3-methoxyphenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound COC1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NC3CCN(C)CC3)=CC=2)[N+]([O-])=O)=C1 SAZVZHLHOFBCAR-UHFFFAOYSA-N 0.000 description 1
- YAGUDAARBDRLDQ-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(4-fluorophenoxy)-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=CC(F)=CC=2)C=C1[N+]([O-])=O YAGUDAARBDRLDQ-UHFFFAOYSA-N 0.000 description 1
- JCHOJWHRTHVGDM-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(3-methyl-1h-indol-4-yl)oxy]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=12C(C)=CNC2=CC=CC=1OC1=CC(N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCOCC1 JCHOJWHRTHVGDM-UHFFFAOYSA-N 0.000 description 1
- YYQKXBHTNKGKMK-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(4-fluoro-1h-indol-5-yl)oxy]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=C3C=CNC3=CC=2)F)C=C1[N+]([O-])=O YYQKXBHTNKGKMK-UHFFFAOYSA-N 0.000 description 1
- HRIKCEUAFHZGRV-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6,7-difluoro-1h-indol-5-yl)oxy]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=C(F)C=3NC=CC=3C=2)F)C=C1[N+]([O-])=O HRIKCEUAFHZGRV-UHFFFAOYSA-N 0.000 description 1
- YAFMDPTZQCVKDG-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1H-indol-5-yl)oxy]-N-[4-[(4-hydroxycyclohexyl)methylamino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCC(O)CC1 YAFMDPTZQCVKDG-UHFFFAOYSA-N 0.000 description 1
- QLMFYFBJKINBLD-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indazol-4-yl)oxy]-n-[4-[(4-fluorooxan-4-yl)methoxy]-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=3C=NNC=3C=C(F)C=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1OCC1(F)CCOCC1 QLMFYFBJKINBLD-UHFFFAOYSA-N 0.000 description 1
- QODAWCXSYSLWDU-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-4-yl)oxy]-n-[3-nitro-4-[3-(3-oxopiperazin-1-yl)propylamino]phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=3C=CNC=3C=C(F)C=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCNC(=O)C1 QODAWCXSYSLWDU-UHFFFAOYSA-N 0.000 description 1
- NXLYDCOXWNYQIW-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-4-yl)oxy]-n-[4-(2-methoxyethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C1=C([N+]([O-])=O)C(NCCOC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC(F)=CC2=C1C=CN2 NXLYDCOXWNYQIW-UHFFFAOYSA-N 0.000 description 1
- LKJYIFUOZOLGNE-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[3-nitro-4-(oxan-4-ylamino)phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC1CCOCC1 LKJYIFUOZOLGNE-UHFFFAOYSA-N 0.000 description 1
- NMYZWNHCUHNJBC-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[3-nitro-4-(oxan-4-ylmethoxy)phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1OCC1CCOCC1 NMYZWNHCUHNJBC-UHFFFAOYSA-N 0.000 description 1
- DLDPTIUKWVBKFO-SSEXGKCCSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[3-nitro-4-[[(3r)-oxan-3-yl]methylamino]phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC[C@H]1CCCOC1 DLDPTIUKWVBKFO-SSEXGKCCSA-N 0.000 description 1
- DLDPTIUKWVBKFO-PMERELPUSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[3-nitro-4-[[(3s)-oxan-3-yl]methylamino]phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC[C@@H]1CCCOC1 DLDPTIUKWVBKFO-PMERELPUSA-N 0.000 description 1
- WMVXEZJLUZPMLU-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[3-nitro-4-[[4-(oxetan-3-yl)morpholin-2-yl]methylamino]phenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC(OCC1)CN1C1COC1 WMVXEZJLUZPMLU-UHFFFAOYSA-N 0.000 description 1
- XEYAEYWFXJRGRL-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[4-(2-methoxyethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C1=C([N+]([O-])=O)C(NCCOC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)C=C1OC(C(=C1)F)=CC2=C1NC=C2 XEYAEYWFXJRGRL-UHFFFAOYSA-N 0.000 description 1
- SJQYGOQAKXTPDE-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[4-(4-morpholin-4-ylbut-2-ynoxy)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1OCC#CCN1CCOCC1 SJQYGOQAKXTPDE-UHFFFAOYSA-N 0.000 description 1
- DFIUOZBODVKENQ-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[4-(morpholin-4-ylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NN1CCOCC1 DFIUOZBODVKENQ-UHFFFAOYSA-N 0.000 description 1
- UIMGXUZJOZNIRN-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=CC=3NC=CC=3C=2)F)C=C1[N+]([O-])=O UIMGXUZJOZNIRN-UHFFFAOYSA-N 0.000 description 1
- ZKQHVESAQKHQQK-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(7-fluoro-1h-indol-5-yl)oxy]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C3C=CNC3=C(F)C=2)C=C1[N+]([O-])=O ZKQHVESAQKHQQK-UHFFFAOYSA-N 0.000 description 1
- WITALSTUWOTYER-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[2-chloro-3-(trifluoromethyl)phenoxy]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C(=C(C=CC=2)C(F)(F)F)Cl)C=C1[N+]([O-])=O WITALSTUWOTYER-UHFFFAOYSA-N 0.000 description 1
- DXSIROTUPAUIPH-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[3-(methoxymethoxy)-2-methylphenoxy]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonylbenzamide Chemical compound COCOC1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NC3CCN(C)CC3)=CC=2)[N+]([O-])=O)=C1C DXSIROTUPAUIPH-UHFFFAOYSA-N 0.000 description 1
- LOEDGICPNFWGGT-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-[(2-oxo-1,3-dihydroindol-4-yl)oxy]benzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=3CC(=O)NC=3C=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 LOEDGICPNFWGGT-UHFFFAOYSA-N 0.000 description 1
- ROMNWHAFULEVBG-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-[(2-oxo-1,3-dihydroindol-5-yl)oxy]benzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C3CC(=O)NC3=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 ROMNWHAFULEVBG-UHFFFAOYSA-N 0.000 description 1
- DTDOPDTZFYNOOE-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-[2-(1h-pyrazol-5-yl)phenoxy]benzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=CC=2)C=2NN=CC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 DTDOPDTZFYNOOE-UHFFFAOYSA-N 0.000 description 1
- PJOKOHCOMHEROG-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-(2-methoxyethylamino)-3-nitrophenyl]sulfonyl-2-[(2-oxo-1,3-dihydroindol-4-yl)oxy]benzamide Chemical compound C1=C([N+]([O-])=O)C(NCCOC)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC=CC2=C1CC(=O)N2 PJOKOHCOMHEROG-UHFFFAOYSA-N 0.000 description 1
- JHBAMTIBWTZZMX-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(1-methylpiperidin-4-yl)amino]-3-nitrophenyl]sulfonyl-2-[3-(trifluoromethyl)phenoxy]benzamide Chemical compound C1CN(C)CCC1NC1=CC=C(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)OC=2C=C(C=CC=2)C(F)(F)F)C=C1[N+]([O-])=O JHBAMTIBWTZZMX-UHFFFAOYSA-N 0.000 description 1
- MCEJBRBKHBZOAK-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[(4,4-difluorocyclohexyl)methylamino]-3-nitrophenyl]sulfonyl-2-[(6-fluoro-1h-indol-5-yl)oxy]benzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCC(F)(F)CC1 MCEJBRBKHBZOAK-UHFFFAOYSA-N 0.000 description 1
- XRBVTNUARSPHNE-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[3-(dimethylamino)propylamino]-3-nitrophenyl]sulfonyl-2-(2-fluorophenoxy)benzamide Chemical compound C1=C([N+]([O-])=O)C(NCCCN(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3CCC(C)(C)CC=3C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC=CC=C1F XRBVTNUARSPHNE-UHFFFAOYSA-N 0.000 description 1
- LJIFUMIJYSRNJT-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[5-cyano-6-(oxan-4-ylmethoxy)pyridin-3-yl]sulfonyl-2-[(6-fluoro-1h-indol-5-yl)oxy]benzamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1C#N)=CN=C1OCC1CCOCC1 LJIFUMIJYSRNJT-UHFFFAOYSA-N 0.000 description 1
- QOIMULLTRNQFCS-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)-5,5-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-[(6-fluoro-1h-indol-5-yl)oxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C1C(C)(C)CCC(C=2C=CC(Cl)=CC=2)=C1CN(CC1)CCN1C(C=C1OC=2C(=CC=3NC=CC=3C=2)F)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 QOIMULLTRNQFCS-UHFFFAOYSA-N 0.000 description 1
- BMTAZHFNFVYYBP-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-(1-methylbenzimidazol-5-yl)oxy-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=C2N(C)C=NC2=CC=1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCCCN1CCOCC1 BMTAZHFNFVYYBP-UHFFFAOYSA-N 0.000 description 1
- JPTFPGHJBJAWQL-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-(3-methoxyphenoxy)-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound COC1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NCC3CCOCC3)=CC=2)[N+]([O-])=O)=C1 JPTFPGHJBJAWQL-UHFFFAOYSA-N 0.000 description 1
- RSHWKIXZALCTPW-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-(3-nitrophenoxy)-n-[4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=CC(NCC3CCOCC3)=CC=2)=C1 RSHWKIXZALCTPW-UHFFFAOYSA-N 0.000 description 1
- ZMCAQKBWFMOQOT-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound C=1C=C2SC(C)=NC2=CC=1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 ZMCAQKBWFMOQOT-UHFFFAOYSA-N 0.000 description 1
- XMVCYDCKJFMKJV-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[2-[(dimethylamino)methyl]phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound CN(C)CC1=CC=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 XMVCYDCKJFMKJV-UHFFFAOYSA-N 0.000 description 1
- YOKPFNMXROIGQN-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[2-[3-(dimethylamino)propyl]phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound CN(C)CCCC1=CC=CC=C1OC1=CC(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 YOKPFNMXROIGQN-UHFFFAOYSA-N 0.000 description 1
- PQKYIXQQSLPZAE-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[3-[2-(dimethylamino)-2-oxoethoxy]phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound CN(C)C(=O)COC1=CC=CC(OC=2C(=CC=C(C=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C(=O)NS(=O)(=O)C=2C=C(C(NCC3CCOCC3)=CC=2)[N+]([O-])=O)=C1 PQKYIXQQSLPZAE-UHFFFAOYSA-N 0.000 description 1
- DLWPWHHSDVYXCO-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[4-(2-morpholin-4-ylethoxy)phenoxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=CC(OCCN3CCOCC3)=CC=2)=CC=C1NCC1CCOCC1 DLWPWHHSDVYXCO-UHFFFAOYSA-N 0.000 description 1
- KJGBJADBAVJRGM-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-2-[[3-(3-morpholin-4-yl-3-oxopropyl)-1h-indol-5-yl]oxy]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=C3C(CCC(=O)N4CCOCC4)=CNC3=CC=2)=CC=C1NCC1CCOCC1 KJGBJADBAVJRGM-UHFFFAOYSA-N 0.000 description 1
- JTHPVBULJQVKHF-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonyl-2-[(2-oxo-3,4-dihydro-1h-quinolin-5-yl)oxy]benzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=3CCC(=O)NC=3C=CC=2)=CC=C1NCC1CCOCC1 JTHPVBULJQVKHF-UHFFFAOYSA-N 0.000 description 1
- HZMVWMGETPHMFD-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-(3-morpholin-4-ylpropylamino)-3-nitrophenyl]sulfonyl-2-(4-pyridin-3-ylphenoxy)benzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C(=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)OC=2C=CC(=CC=2)C=2C=NC=CC=2)=CC=C1NCCCN1CCOCC1 HZMVWMGETPHMFD-UHFFFAOYSA-N 0.000 description 1
- VKHGIGLNVONZFR-UHFFFAOYSA-N 4-[4-[[2-(4-chlorophenyl)phenyl]methyl]piperazin-1-yl]-n-[4-[3-(dimethylamino)propylamino]-3-nitrophenyl]sulfonyl-2-[(2-oxo-3,4-dihydro-1h-quinolin-5-yl)oxy]benzamide Chemical compound C1=C([N+]([O-])=O)C(NCCCN(C)C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(N2CCN(CC=3C(=CC=CC=3)C=3C=CC(Cl)=CC=3)CC2)C=C1OC1=CC=CC2=C1CCC(=O)N2 VKHGIGLNVONZFR-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 102220506028 Adenylyl-sulfate kinase_R37A_mutation Human genes 0.000 description 1
- 102100021569 Apoptosis regulator Bcl-2 Human genes 0.000 description 1
- 239000012664 BCL-2-inhibitor Substances 0.000 description 1
- 229940123711 Bcl2 inhibitor Drugs 0.000 description 1
- 206010048396 Bone marrow transplant rejection Diseases 0.000 description 1
- RVNVXMDWDGWDEF-WXUXXXNLSA-N CC1(C)CCC(CN2CCN(CC2)c2ccc(C(=O)NS(=O)(=O)c3ccc(NC[C@H]4CC[C@@H](CC4)C#N)c(c3)[N+]([O-])=O)c(Oc3cnc(N)c(Cl)c3)c2)=C(C1)c1ccc(Cl)cc1 Chemical compound CC1(C)CCC(CN2CCN(CC2)c2ccc(C(=O)NS(=O)(=O)c3ccc(NC[C@H]4CC[C@@H](CC4)C#N)c(c3)[N+]([O-])=O)c(Oc3cnc(N)c(Cl)c3)c2)=C(C1)c1ccc(Cl)cc1 RVNVXMDWDGWDEF-WXUXXXNLSA-N 0.000 description 1
- QBJWZAPZKXXERY-GTXVXJEKSA-N CC1(C)CCC(CN2CCN(CC2)c2ccc(C(=O)NS(=O)(=O)c3ccc(N[C@H]4CC[C@@H](CC4)N4CCOCC4)c(c3)[N+]([O-])=O)c(Oc3cc4cc[nH]c4cc3F)c2)=C(C1)c1ccc(Cl)cc1 Chemical compound CC1(C)CCC(CN2CCN(CC2)c2ccc(C(=O)NS(=O)(=O)c3ccc(N[C@H]4CC[C@@H](CC4)N4CCOCC4)c(c3)[N+]([O-])=O)c(Oc3cc4cc[nH]c4cc3F)c2)=C(C1)c1ccc(Cl)cc1 QBJWZAPZKXXERY-GTXVXJEKSA-N 0.000 description 1
- PPYSTORXYCWCKI-GTXVXJEKSA-N CC1(C)CCC(CN2CCN(CC2)c2ccc(C(=O)NS(=O)(=O)c3ccc(N[C@H]4CC[C@@H](CC4)N4CCOCC4)c(c3)[N+]([O-])=O)c(Oc3cccc(Cl)c3)c2)=C(C1)c1ccc(Cl)cc1 Chemical compound CC1(C)CCC(CN2CCN(CC2)c2ccc(C(=O)NS(=O)(=O)c3ccc(N[C@H]4CC[C@@H](CC4)N4CCOCC4)c(c3)[N+]([O-])=O)c(Oc3cccc(Cl)c3)c2)=C(C1)c1ccc(Cl)cc1 PPYSTORXYCWCKI-GTXVXJEKSA-N 0.000 description 1
- BDKQYNYDZZQMFN-AQIHZXJDSA-N CC1(C)CCC(CN2CCN(CC2)c2ccc(C(=O)NS(=O)(=O)c3ccc(O[C@H]4CC[C@@H](CC4)N4CCOCC4)c(c3)[N+]([O-])=O)c(Oc3cc4cc[nH]c4cc3F)c2)=C(C1)c1ccc(Cl)cc1 Chemical compound CC1(C)CCC(CN2CCN(CC2)c2ccc(C(=O)NS(=O)(=O)c3ccc(O[C@H]4CC[C@@H](CC4)N4CCOCC4)c(c3)[N+]([O-])=O)c(Oc3cc4cc[nH]c4cc3F)c2)=C(C1)c1ccc(Cl)cc1 BDKQYNYDZZQMFN-AQIHZXJDSA-N 0.000 description 1
- UEAZWXHTWQQGJE-REKUNCKWSA-N CC1(C)CCC(CN2CCN(CC2)c2ccc(C(=O)NS(=O)(=O)c3cnc(O[C@H]4CC[C@@H](CC4)N4CCOCC4)c(Br)c3)c(Oc3cc4cc[nH]c4cc3F)c2)=C(C1)c1ccc(Cl)cc1 Chemical compound CC1(C)CCC(CN2CCN(CC2)c2ccc(C(=O)NS(=O)(=O)c3cnc(O[C@H]4CC[C@@H](CC4)N4CCOCC4)c(Br)c3)c(Oc3cc4cc[nH]c4cc3F)c2)=C(C1)c1ccc(Cl)cc1 UEAZWXHTWQQGJE-REKUNCKWSA-N 0.000 description 1
- 101100294103 Caenorhabditis elegans nhr-31 gene Proteins 0.000 description 1
- 101100294120 Caenorhabditis elegans nhr-55 gene Proteins 0.000 description 1
- 101100079979 Caenorhabditis elegans nhr-90 gene Proteins 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102220608648 Methyl-CpG-binding domain protein 1_R30A_mutation Human genes 0.000 description 1
- 102220608644 Methyl-CpG-binding domain protein 1_R44K_mutation Human genes 0.000 description 1
- FAVILPQOIVPCBJ-UHFFFAOYSA-N OC1(CCN(CC1)C)CNC1=C(C=C(C=C1)S(=O)(=O)C1=C(C(=O)N)C=CC=C1)[N+](=O)[O-] Chemical compound OC1(CCN(CC1)C)CNC1=C(C=C(C=C1)S(=O)(=O)C1=C(C(=O)N)C=CC=C1)[N+](=O)[O-] FAVILPQOIVPCBJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- XZUDGJUYBJOZDW-YBEWYAPJSA-N [O-][N+](=O)c1cc(ccc1N[C@H]1CC[C@@H](CC1)N1CCOCC1)S(=O)(=O)NC(=O)c1ccc(cc1Oc1cc2cc[nH]c2cc1Cl)N1CCN(CC2=C(CCOCC2)c2ccc(Cl)cc2)CC1 Chemical compound [O-][N+](=O)c1cc(ccc1N[C@H]1CC[C@@H](CC1)N1CCOCC1)S(=O)(=O)NC(=O)c1ccc(cc1Oc1cc2cc[nH]c2cc1Cl)N1CCN(CC2=C(CCOCC2)c2ccc(Cl)cc2)CC1 XZUDGJUYBJOZDW-YBEWYAPJSA-N 0.000 description 1
- WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000007854 aminals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000003725 azepanyl group Chemical group 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- SHOMMGQAMRXRRK-UHFFFAOYSA-N bicyclo[3.1.1]heptane Chemical compound C1C2CC1CCC2 SHOMMGQAMRXRRK-UHFFFAOYSA-N 0.000 description 1
- GNTFBMAGLFYMMZ-UHFFFAOYSA-N bicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CCC2 GNTFBMAGLFYMMZ-UHFFFAOYSA-N 0.000 description 1
- WNTGVOIBBXFMLR-UHFFFAOYSA-N bicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1C2 WNTGVOIBBXFMLR-UHFFFAOYSA-N 0.000 description 1
- KVLCIHRZDOKRLK-UHFFFAOYSA-N bicyclo[4.2.1]nonane Chemical compound C1C2CCC1CCCC2 KVLCIHRZDOKRLK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000005959 diazepanyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 230000005750 disease progression Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 125000005883 dithianyl group Chemical group 0.000 description 1
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 description 1
- 238000004980 dosimetry Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000003325 follicular Effects 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 150000002374 hemiaminals Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000005969 isothiazolinyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 238000001948 isotopic labelling Methods 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000003971 isoxazolinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
- VQWNELPXJLCING-UHFFFAOYSA-N n-[4-[[2-(6-amino-5-chloropyridin-3-yl)oxy-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]benzoyl]sulfamoyl]-2-nitrophenyl]-4-cyanopiperidine-1-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Cl)C(N)=NC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(=O)N1CCC(C#N)CC1 VQWNELPXJLCING-UHFFFAOYSA-N 0.000 description 1
- XDOCKJXYYKYDQV-UHFFFAOYSA-N n-[4-[[2-(6-amino-5-chloropyridin-3-yl)oxy-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]benzoyl]sulfamoyl]-2-nitrophenyl]morpholine-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C=1CC(C)(C)CCC=1CN(CC1)CCN1C(C=C1OC=2C=C(Cl)C(N)=NC=2)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NC(=O)N1CCOCC1 XDOCKJXYYKYDQV-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 125000005963 oxadiazolidinyl group Chemical group 0.000 description 1
- 125000005882 oxadiazolinyl group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000008039 phosphoramides Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- NVPICXQHSYQKGM-UHFFFAOYSA-N piperidine-1-carbonitrile Chemical compound N#CN1CCCCC1 NVPICXQHSYQKGM-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005304 thiadiazolidinyl group Chemical group 0.000 description 1
- 125000005305 thiadiazolinyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PCFIPYFVXDCWBW-UHFFFAOYSA-N tricyclo[3.3.1.03,7]nonane Chemical compound C1C(C2)C3CC2CC1C3 PCFIPYFVXDCWBW-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/30—Nitrogen atoms non-acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Indole Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/631,367 | 2009-12-04 | ||
| US12/631,367 US20100160322A1 (en) | 2008-12-04 | 2009-12-04 | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| PCT/US2010/036844 WO2011068560A1 (en) | 2009-12-04 | 2010-06-01 | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2010326727A1 AU2010326727A1 (en) | 2012-06-07 |
| AU2010326727B2 true AU2010326727B2 (en) | 2014-05-29 |
Family
ID=42463423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2010326727A Ceased AU2010326727B2 (en) | 2009-12-04 | 2010-06-01 | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
Country Status (30)
| Country | Link |
|---|---|
| US (5) | US20100160322A1 (enExample) |
| EP (1) | EP2507211B1 (enExample) |
| JP (1) | JP5589090B2 (enExample) |
| CN (2) | CN106397418A (enExample) |
| AR (1) | AR076946A1 (enExample) |
| AU (1) | AU2010326727B2 (enExample) |
| BR (1) | BR112012012918A8 (enExample) |
| CA (1) | CA2781521A1 (enExample) |
| CL (1) | CL2012001421A1 (enExample) |
| CO (1) | CO6571908A2 (enExample) |
| CR (1) | CR20120347A (enExample) |
| CY (1) | CY1115502T1 (enExample) |
| DK (1) | DK2507211T3 (enExample) |
| DO (1) | DOP2012000154A (enExample) |
| EC (1) | ECSP12012020A (enExample) |
| ES (1) | ES2487617T3 (enExample) |
| IL (1) | IL219991A (enExample) |
| MX (1) | MX2012006391A (enExample) |
| MY (1) | MY161340A (enExample) |
| NZ (1) | NZ600084A (enExample) |
| PE (1) | PE20121496A1 (enExample) |
| PH (1) | PH12012501071A1 (enExample) |
| PL (1) | PL2507211T3 (enExample) |
| PT (1) | PT2507211E (enExample) |
| RU (1) | RU2535203C2 (enExample) |
| SG (1) | SG181506A1 (enExample) |
| SI (1) | SI2507211T1 (enExample) |
| TW (1) | TWI473801B (enExample) |
| UA (1) | UA106403C2 (enExample) |
| WO (1) | WO2011068560A1 (enExample) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9259399B2 (en) | 2007-11-07 | 2016-02-16 | Cornell University | Targeting CDK4 and CDK6 in cancer therapy |
| US20100160322A1 (en) | 2008-12-04 | 2010-06-24 | Abbott Laboratories | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| US8557983B2 (en) * | 2008-12-04 | 2013-10-15 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| US8586754B2 (en) * | 2008-12-05 | 2013-11-19 | Abbvie Inc. | BCL-2-selective apoptosis-inducing agents for the treatment of cancer and immune diseases |
| US8563735B2 (en) | 2008-12-05 | 2013-10-22 | Abbvie Inc. | Bcl-2-selective apoptosis-inducing agents for the treatment of cancer and immune diseases |
| NZ593594A (en) | 2009-01-19 | 2013-08-30 | Abbvie Inc | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| HUE025527T2 (en) * | 2009-01-19 | 2016-04-28 | Abbvie Inc | Apoptosis inducers for the treatment of cancer, immune and autoimmune diseases |
| US20220315555A1 (en) | 2009-05-26 | 2022-10-06 | Abbvie Inc. | Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases |
| PH12015500297B1 (en) * | 2009-05-26 | 2023-10-20 | Abbvie Ireland Unlimited Co | Adoptosis-inducing agents for the treatment of cancer and immune and automoimmune disease |
| US9034875B2 (en) | 2009-05-26 | 2015-05-19 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| US8546399B2 (en) | 2009-05-26 | 2013-10-01 | Abbvie Inc. | Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases |
| DK2550258T3 (en) | 2010-03-25 | 2015-12-07 | Abbvie Inc | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| TWI520960B (zh) * | 2010-05-26 | 2016-02-11 | 艾伯維有限公司 | 用於治療癌症及免疫及自體免疫疾病之細胞凋亡誘導劑 |
| NZ717373A (en) | 2010-06-03 | 2017-11-24 | Pharmacyclics Llc | The use of inhibitors of bruton’s tyrosine kinase (btk) |
| UA113500C2 (xx) * | 2010-10-29 | 2017-02-10 | Одержані екструзією розплаву тверді дисперсії, що містять індукуючий апоптоз засіб | |
| KR20180059560A (ko) * | 2010-10-29 | 2018-06-04 | 애브비 인코포레이티드 | 아폽토시스―유도제를 포함하는 고체 분산체 |
| PH12013501006A1 (en) | 2010-11-23 | 2022-03-30 | Abbvie Ireland Unlimited Co | Methods of treatment using selective bcl-2 inhibitors |
| PT2643322T (pt) | 2010-11-23 | 2017-11-13 | Abbvie Inc | Sais e formas cristalinas de um agente indutor de apoptose |
| CN103958508B (zh) | 2011-10-14 | 2019-02-12 | 艾伯维公司 | 用于治疗癌症以及免疫与自身免疫性疾病的细胞凋亡诱导剂 |
| US20140303191A1 (en) * | 2011-10-19 | 2014-10-09 | Pharmacyclics, Inc. | Use of inhibitors of bruton's tyrosine kinase (btk) |
| US10954567B2 (en) | 2012-07-24 | 2021-03-23 | Pharmacyclics Llc | Mutations associated with resistance to inhibitors of Bruton's Tyrosine Kinase (BTK) |
| CN105164128B (zh) * | 2013-03-13 | 2017-12-12 | 艾伯维公司 | 制备细胞凋亡诱导剂的方法 |
| US20140275082A1 (en) | 2013-03-14 | 2014-09-18 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| US20170216286A1 (en) | 2014-01-28 | 2017-08-03 | Mayo Foundation For Medical Education And Research | Killing senescent cells and treating senescence-associated conditions using a src inhibitor and a flavonoid |
| IL311537A (en) | 2014-01-28 | 2024-05-01 | Mayo Found Medical Education & Res | Methods and preparations for killing aging cells and for the treatment of diseases and disorders related to aging |
| US10328058B2 (en) | 2014-01-28 | 2019-06-25 | Mayo Foundation For Medical Education And Research | Treating atherosclerosis by removing senescent foam cell macrophages from atherosclerotic plaques |
| US20190269675A1 (en) | 2014-01-28 | 2019-09-05 | Buck Institute for Research and Aging | Treatment of parkinson's disease and other conditions caused or mediated by senescent astrocytes using small molecule senolytic agents |
| CA2942528A1 (en) | 2014-03-20 | 2015-09-24 | Pharmacyclics Inc. | Phospholipase c gamma 2 and resistance associated mutations |
| AU2015240465B2 (en) | 2014-04-04 | 2020-02-27 | Del Mar Pharmaceuticals | Use of dianhydrogalactitol and analogs or derivatives thereof to treat non-small-cell carcinoma of the lung and ovarian cancer |
| US20170231986A1 (en) | 2014-08-11 | 2017-08-17 | Acerta Pharma B.V. | Therapeutic Combinations of a BTK Inhibitor, a PI3K Inhibitor, a JAK-2 Inhibitor, and/or a BCL-2 Inhibitor |
| SG10201902963PA (en) | 2014-10-06 | 2019-05-30 | Vertex Pharma | Modulators of cystic fibrosis transmembrane conductance regulator |
| US10195213B2 (en) | 2015-03-13 | 2019-02-05 | Unity Biotechnology, Inc. | Chemical entities that kill senescent cells for use in treating age-related disease |
| AU2017240685B2 (en) | 2016-03-31 | 2021-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| GEP20217329B (en) | 2016-09-30 | 2021-12-10 | Vertex Pharma | Modulator of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| HUE052205T2 (hu) * | 2016-12-09 | 2021-04-28 | Vertex Pharma | Cisztás fibrózis transzmembrán vezetõképesség szabályzó modulátora, gyógyszerészeti készítmények, kezelési eljárások és eljárás a modulátor elõállítására |
| BR112019025801A2 (pt) | 2017-06-08 | 2020-07-07 | Vertex Pharmaceuticals Incorporated | métodos de tratamento para fibrose cística |
| CN110759908B (zh) * | 2017-06-26 | 2021-03-12 | 深圳市塔吉瑞生物医药有限公司 | 用于抑制Bcl-2蛋白的N-苯磺酰基苯甲酰胺类化合物及其组合物及应用 |
| BR112020000941A2 (pt) | 2017-07-17 | 2020-07-21 | Vertex Pharmaceuticals Incorporated | métodos de tratamento para fibrose cística |
| US11434201B2 (en) | 2017-08-02 | 2022-09-06 | Vertex Pharmaceuticals Incorporated | Processes for preparing pyrrolidine compounds |
| ES2948287T3 (es) | 2017-08-23 | 2023-09-07 | Guangzhou Lupeng Pharmaceutical Company Ltd | Derivados heterocíclicos condensados como inhibidores de Bcl-2 para el tratamiento de enfermedades neoplásicas |
| CA3078893A1 (en) | 2017-10-19 | 2019-04-25 | Vertex Pharmaceuticals Incorporated | Crystalline forms and compositions of cftr modulators |
| CA3085006A1 (en) | 2017-12-08 | 2019-06-13 | Vertex Pharmaceuticals Incorporated | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
| SG11202005785XA (en) | 2018-01-10 | 2020-07-29 | Recurium Ip Holdings Llc | Benzamide compounds |
| TWI810243B (zh) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | 用於治療囊腫纖化症之醫藥組合物 |
| EP3774825A1 (en) | 2018-04-13 | 2021-02-17 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| US12220419B2 (en) | 2018-08-22 | 2025-02-11 | Newave Pharmaceutical Inc. | BCL-2 inhibitors |
| CN109851535A (zh) * | 2019-01-30 | 2019-06-07 | 天津现代职业技术学院 | 一种制备4-氟-3-(三氟甲磺酰基)苯磺酰胺的方法 |
| CN113444078B (zh) * | 2020-03-25 | 2023-07-07 | 中国科学院上海有机化学研究所 | 抗凋亡蛋白Bcl-2抑制剂及其制备方法和应用 |
| CN111978246A (zh) * | 2020-09-26 | 2020-11-24 | 安徽金禾实业股份有限公司 | 一种2-甲基-3-甲氧基-4-氯吡啶的纯化合成方法 |
| CN117616023A (zh) * | 2021-04-13 | 2024-02-27 | 爱新医药科技(香港)有限公司 | Bcl-2或bcl-2/bcl-xl调节剂及其用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005049593A2 (en) * | 2003-11-13 | 2005-06-02 | Abbott Laboratories | N-acylsulfonamide apoptosis promoters |
Family Cites Families (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4126937A1 (de) | 1991-08-10 | 1993-02-11 | Basf Ag | Salicyl(thio)etherderivate, verfahren und zwischenprodukte zu ihrer herstellung |
| JPH06510763A (ja) | 1991-08-19 | 1994-12-01 | イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー | アンジオテンシン2受容体遮断イミダゾリノン誘導体 |
| GB9203798D0 (en) | 1992-02-21 | 1992-04-08 | Fujisawa Pharmaceutical Co | Quinolylbenzofuran derivatives,processes for preparation thereof and pharmaceutical composition comprising the same |
| MY115155A (en) | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| PT1019385E (pt) | 1995-09-15 | 2004-06-30 | Upjohn Co | N-oxidos de aminoaril-oxazolidinona |
| CN1265669A (zh) | 1997-07-31 | 2000-09-06 | 伊兰药品公司 | 抑制由vla-4介导的白细胞粘着的化合物 |
| US20030220234A1 (en) * | 1998-11-02 | 2003-11-27 | Selvaraj Naicker | Deuterated cyclosporine analogs and their use as immunodulating agents |
| US6410584B1 (en) | 1998-01-14 | 2002-06-25 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells with indole derivatives |
| IL137465A0 (en) | 1998-02-04 | 2001-07-24 | Novartis Ag | Sulfonylamino derivatives which inhibit matrix-degrading metalloproteinases |
| KR20010083092A (ko) | 1998-07-06 | 2001-08-31 | 스티븐 비. 데이비스 | 이중 안지오텐신 엔도텔린 수용체 길항제로서의 비페닐술폰아미드 |
| DE19830430A1 (de) * | 1998-07-08 | 2000-01-13 | Hoechst Marion Roussel De Gmbh | Schwefelsubstituierte Sulfonylamino-carbonsäure-N-arylamide, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| YU44901A (sh) | 1998-12-22 | 2003-12-31 | F. Hofmann-La Roche Ag. | Sulfonamid hidroksamati |
| GB9918037D0 (en) * | 1999-07-30 | 1999-09-29 | Biochemie Gmbh | Organic compounds |
| BR0013143A (pt) | 1999-08-12 | 2002-06-11 | Pharmacia Italia Spa | Derivados de 3 (5) amino pirazol, processo para sua preparação e uso dos mesmos como agentes antitumorais |
| CN1425004A (zh) | 2000-03-21 | 2003-06-18 | 宝洁公司 | 含杂环侧链的n-取代的金属蛋白酶抑制剂 |
| WO2001070693A2 (en) | 2000-03-21 | 2001-09-27 | The Procter & Gamble Company | Difluorobutyric acid derivatives and their use as metalloprotease inhibitors |
| AR031130A1 (es) * | 2000-09-20 | 2003-09-10 | Abbott Lab | N-acilsulfonamidas promotoras de la apoptosis |
| US6720338B2 (en) * | 2000-09-20 | 2004-04-13 | Abbott Laboratories | N-acylsulfonamide apoptosis promoters |
| US20020055631A1 (en) * | 2000-09-20 | 2002-05-09 | Augeri David J. | N-acylsulfonamide apoptosis promoters |
| US6995162B2 (en) | 2001-01-12 | 2006-02-07 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
| JP4167173B2 (ja) * | 2001-06-06 | 2008-10-15 | イーライ リリー アンド カンパニー | 抗腫瘍剤としての使用のためのベンゾイルスルホンアミドおよびスルホンベンズアミジン |
| UY27450A1 (es) | 2001-09-24 | 2003-04-30 | Bayer Corp | Preparación y uso de derivados de imidazol para el tratamiento de la obesidad |
| AR043059A1 (es) | 2002-11-12 | 2005-07-13 | Bayer Pharmaceuticals Corp | Derivados de indolil pirazinona utiles para el tratamiento de trastornos hiper-proliferativos |
| DE60316984T2 (de) | 2002-11-22 | 2008-07-17 | Eli Lilly And Co., Indianapolis | Benzoylsulfonamide als antitumor-mittel |
| WO2005024636A1 (ja) | 2003-09-04 | 2005-03-17 | Hitachi Ulsi Systems Co., Ltd. | 半導体装置 |
| US7642260B2 (en) * | 2003-11-13 | 2010-01-05 | Abbott Laboratories, Inc. | Apoptosis promoters |
| US7973161B2 (en) * | 2003-11-13 | 2011-07-05 | Abbott Laboratories | Apoptosis promoters |
| US8614318B2 (en) * | 2003-11-13 | 2013-12-24 | Abbvie Inc. | Apoptosis promoters |
| US7767684B2 (en) * | 2003-11-13 | 2010-08-03 | Abbott Laboratories | Apoptosis promoters |
| EP1697738A1 (en) * | 2003-11-20 | 2006-09-06 | Freshpoint Holdings Sa | Method and system for determining the condition of a time-temperature indicator |
| RU2263666C1 (ru) | 2004-04-08 | 2005-11-10 | Общество с ограниченной ответственностью "Исследовательский Институт Химического Разнообразия" (ООО "Исследовательский Институт Химического Разнообразия") | Гетероциклилсульфиновые кислоты и их производные, фокусированная библиотека и фармацевтическая композиция |
| US7307163B2 (en) | 2004-04-19 | 2007-12-11 | Symed Labs Limited | Process for the preparation of linezolid and related compounds |
| CN101006065B (zh) | 2004-06-17 | 2012-07-11 | 英菲尼蒂发现公司 | 抑制bcl蛋白与结合伴侣的相互作用的化合物和方法 |
| PL1768967T3 (pl) | 2004-07-20 | 2009-09-30 | Symed Labs Ltd | Nowe związki pośrednie do wytwarzania linezolidu oraz związki pokrewne |
| US7511013B2 (en) * | 2004-09-29 | 2009-03-31 | Amr Technology, Inc. | Cyclosporin analogues and their pharmaceutical uses |
| TWI337608B (en) * | 2005-05-12 | 2011-02-21 | Abbott Lab | Apoptosis promoters |
| US8624027B2 (en) | 2005-05-12 | 2014-01-07 | Abbvie Inc. | Combination therapy for treating cancer and diagnostic assays for use therein |
| TW200716636A (en) | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Heterocyclic spiro-compounds |
| US7514068B2 (en) * | 2005-09-14 | 2009-04-07 | Concert Pharmaceuticals Inc. | Biphenyl-pyrazolecarboxamide compounds |
| MX2009002422A (es) | 2006-09-05 | 2009-03-20 | Abbott Lab | Inhibidores bcl para tratar exceso de plaquetas. |
| US8796267B2 (en) | 2006-10-23 | 2014-08-05 | Concert Pharmaceuticals, Inc. | Oxazolidinone derivatives and methods of use |
| US20100087436A1 (en) | 2006-11-16 | 2010-04-08 | Abbott Laboratories | Method of preventing or treating organ, hematopoietic stem cell or bone marrow transplant rejection |
| US20080182845A1 (en) | 2006-11-16 | 2008-07-31 | Abbott Laboratories | Method of preventing or treating organ, hematopoietic stem cell or bone marrow transplant rejection |
| JP5130305B2 (ja) | 2007-02-15 | 2013-01-30 | エフ.ホフマン−ラ ロシュ アーゲー | Taar1リガンドとしての2−アミノオキサゾリン |
| CN101687824A (zh) * | 2007-04-19 | 2010-03-31 | 康塞特医药品公司 | 氘化吗啉基化合物 |
| US7531685B2 (en) * | 2007-06-01 | 2009-05-12 | Protia, Llc | Deuterium-enriched oxybutynin |
| WO2009035598A1 (en) | 2007-09-10 | 2009-03-19 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
| US20090118238A1 (en) | 2007-09-17 | 2009-05-07 | Protia, Llc | Deuterium-enriched alendronate |
| US20090082471A1 (en) | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched fingolimod |
| US20090088416A1 (en) | 2007-09-26 | 2009-04-02 | Protia, Llc | Deuterium-enriched lapaquistat |
| JP2010540635A (ja) | 2007-10-02 | 2010-12-24 | コンサート ファーマシューティカルズ インコーポレイテッド | ピリミジンジオン誘導体 |
| US20090105338A1 (en) | 2007-10-18 | 2009-04-23 | Protia, Llc | Deuterium-enriched gabexate mesylate |
| EP2212298B1 (en) | 2007-10-18 | 2013-03-27 | Concert Pharmaceuticals Inc. | Deuterated etravirine |
| WO2009055006A1 (en) | 2007-10-26 | 2009-04-30 | Concert Pharmaceuticals, Inc. | Deuterated darunavir |
| KR101585848B1 (ko) | 2007-11-16 | 2016-01-15 | 애브비 인코포레이티드 | 관절염의 치료 방법 |
| US8557983B2 (en) * | 2008-12-04 | 2013-10-15 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| UA108193C2 (uk) | 2008-12-04 | 2015-04-10 | Апоптозіндукуючий засіб для лікування раку і імунних і аутоімунних захворювань | |
| US20100160322A1 (en) | 2008-12-04 | 2010-06-24 | Abbott Laboratories | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| US8563735B2 (en) | 2008-12-05 | 2013-10-22 | Abbvie Inc. | Bcl-2-selective apoptosis-inducing agents for the treatment of cancer and immune diseases |
| US8586754B2 (en) * | 2008-12-05 | 2013-11-19 | Abbvie Inc. | BCL-2-selective apoptosis-inducing agents for the treatment of cancer and immune diseases |
| CN106008322B (zh) * | 2008-12-05 | 2018-09-04 | Abbvie 公司 | 作为用于治疗癌症和免疫疾病的bcl-2-选择性诱发细胞凋亡药剂的磺酰胺衍生物 |
| NZ593594A (en) | 2009-01-19 | 2013-08-30 | Abbvie Inc | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| HUE025527T2 (en) | 2009-01-19 | 2016-04-28 | Abbvie Inc | Apoptosis inducers for the treatment of cancer, immune and autoimmune diseases |
| PH12015500297B1 (en) | 2009-05-26 | 2023-10-20 | Abbvie Ireland Unlimited Co | Adoptosis-inducing agents for the treatment of cancer and immune and automoimmune disease |
| US8546399B2 (en) | 2009-05-26 | 2013-10-01 | Abbvie Inc. | Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases |
| US9034875B2 (en) | 2009-05-26 | 2015-05-19 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
-
2009
- 2009-12-04 US US12/631,367 patent/US20100160322A1/en not_active Abandoned
-
2010
- 2010-06-01 CA CA2781521A patent/CA2781521A1/en not_active Abandoned
- 2010-06-01 RU RU2012127790/04A patent/RU2535203C2/ru active
- 2010-06-01 JP JP2012541997A patent/JP5589090B2/ja active Active
- 2010-06-01 UA UAA201208181A patent/UA106403C2/ru unknown
- 2010-06-01 SI SI201030743T patent/SI2507211T1/sl unknown
- 2010-06-01 CN CN201610801580.3A patent/CN106397418A/zh active Pending
- 2010-06-01 CN CN201080065339XA patent/CN103097352A/zh active Pending
- 2010-06-01 SG SG2012041018A patent/SG181506A1/en unknown
- 2010-06-01 WO PCT/US2010/036844 patent/WO2011068560A1/en not_active Ceased
- 2010-06-01 AU AU2010326727A patent/AU2010326727B2/en not_active Ceased
- 2010-06-01 BR BR112012012918A patent/BR112012012918A8/pt not_active Application Discontinuation
- 2010-06-01 ES ES10722500.5T patent/ES2487617T3/es active Active
- 2010-06-01 MY MYPI2012700318A patent/MY161340A/en unknown
- 2010-06-01 DK DK10722500.5T patent/DK2507211T3/da active
- 2010-06-01 PT PT107225005T patent/PT2507211E/pt unknown
- 2010-06-01 PE PE2012000765A patent/PE20121496A1/es active IP Right Grant
- 2010-06-01 PL PL10722500T patent/PL2507211T3/pl unknown
- 2010-06-01 MX MX2012006391A patent/MX2012006391A/es unknown
- 2010-06-01 NZ NZ600084A patent/NZ600084A/en not_active IP Right Cessation
- 2010-06-01 PH PH1/2012/501071A patent/PH12012501071A1/en unknown
- 2010-06-01 EP EP10722500.5A patent/EP2507211B1/en active Active
- 2010-06-02 TW TW99117829A patent/TWI473801B/zh not_active IP Right Cessation
- 2010-06-02 AR ARP100101936A patent/AR076946A1/es unknown
-
2012
- 2012-05-24 IL IL219991A patent/IL219991A/en active IP Right Grant
- 2012-05-31 CL CL2012001421A patent/CL2012001421A1/es unknown
- 2012-06-01 DO DO2012000154A patent/DOP2012000154A/es unknown
- 2012-06-07 CO CO12096369A patent/CO6571908A2/es active IP Right Grant
- 2012-06-25 CR CR20120347A patent/CR20120347A/es unknown
- 2012-07-03 EC ECSP12012020 patent/ECSP12012020A/es unknown
-
2013
- 2013-07-26 US US13/952,278 patent/US8952157B2/en active Active
-
2014
- 2014-08-27 CY CY20141100684T patent/CY1115502T1/el unknown
- 2014-12-23 US US14/582,144 patent/US9303025B2/en active Active
-
2016
- 2016-02-19 US US15/048,901 patent/US20160304451A1/en not_active Abandoned
-
2017
- 2017-10-13 US US15/783,993 patent/US20180251426A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005049593A2 (en) * | 2003-11-13 | 2005-06-02 | Abbott Laboratories | N-acylsulfonamide apoptosis promoters |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2010326727B2 (en) | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases | |
| US9029404B2 (en) | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases | |
| AU2009322269B2 (en) | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases | |
| US9315488B2 (en) | Bcl-2-selective apoptosis-inducing agents for the treatment of cancer and immune diseases | |
| DK2376480T3 (en) | Sulfonamide derivatives AS BCL-2-selective apoptosis inducing agents for the treatment of cancer and immune diseases | |
| AU2015221495B2 (en) | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases | |
| HK1177202B (en) | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases | |
| HK1231044A1 (en) | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: ABBVIE INC. Free format text: FORMER APPLICANT(S): ABBOTT LABORATORIES |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |