HUE025905T2 - Non-symmetric pyrrolobenzodiazepine dimers for the treatment of proliferative diseases - Google Patents

Info

Publication number

HUE025905T2

HUE025905T2 HUE09740185A HUE09740185A HUE025905T2 HU E025905 T2 HUE025905 T2 HU E025905T2 HU E09740185 A HUE09740185 A HU E09740185A HU E09740185 A HUE09740185 A HU E09740185A HU E025905 T2 HUE025905 T2 HU E025905T2

Authority

HU

Hungary

Prior art keywords

group

compound

mmol

methoxy

compound according

Prior art date

2008-10-17

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• 238000011282 treatment Methods 0.000 title claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 10
• 230000002062 proliferating effect Effects 0.000 title claims description 10
• 201000010099 disease Diseases 0.000 title claims description 9
• 239000000539 dimer Substances 0.000 title description 6
• -1 cyano cation Chemical class 0.000 claims description 103
• 150000001875 compounds Chemical class 0.000 claims description 101
• 125000000217 alkyl group Chemical group 0.000 claims description 98
• 125000003118 aryl group Chemical group 0.000 claims description 74
• 125000000623 heterocyclic group Chemical group 0.000 claims description 55
• 125000001424 substituent group Chemical group 0.000 claims description 37
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
• 229910052727 yttrium Inorganic materials 0.000 claims description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 239000000203 mixture Substances 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 5
• 125000002252 acyl group Chemical group 0.000 claims description 4
• BCDGQXUMWHRQCB-UHFFFAOYSA-N aminoacetone Chemical compound CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 claims 2
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
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• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims 1
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
• 125000004404 heteroalkyl group Chemical group 0.000 claims 1
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• 239000000243 solution Substances 0.000 description 53
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• 235000019439 ethyl acetate Nutrition 0.000 description 40
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 40
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
• 238000000034 method Methods 0.000 description 34
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 30
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 25
• 239000012267 brine Substances 0.000 description 25
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
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• 239000002904 solvent Substances 0.000 description 24
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 23
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 23
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 22
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
• 125000003277 amino group Chemical group 0.000 description 20
• 238000003818 flash chromatography Methods 0.000 description 20
• 239000012043 crude product Substances 0.000 description 19
• 125000006413 ring segment Chemical group 0.000 description 19
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 125000002947 alkylene group Chemical group 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
• 239000012299 nitrogen atmosphere Substances 0.000 description 16
• 239000012044 organic layer Substances 0.000 description 16
• 150000001768 cations Chemical class 0.000 description 15
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• 150000003839 salts Chemical class 0.000 description 14
• 239000006260 foam Substances 0.000 description 13
• 239000001257 hydrogen Substances 0.000 description 13
• 238000002390 rotary evaporation Methods 0.000 description 13
• 241000790917 Dioxys <bee> Species 0.000 description 12
• 238000001914 filtration Methods 0.000 description 12
• 125000005843 halogen group Chemical group 0.000 description 12
• 125000006239 protecting group Chemical group 0.000 description 12
• 238000000746 purification Methods 0.000 description 12
• YMXFJTUQQVLJEN-UHFFFAOYSA-N pyrimidine Chemical compound C1=CN=CN=C1.C1=CN=CN=C1 YMXFJTUQQVLJEN-UHFFFAOYSA-N 0.000 description 12
• 229920006395 saturated elastomer Polymers 0.000 description 12
• 238000004809 thin layer chromatography Methods 0.000 description 12
• 239000003480 eluent Substances 0.000 description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
• 125000004043 oxo group Chemical group O=* 0.000 description 11
• 229910000029 sodium carbonate Inorganic materials 0.000 description 11
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 239000003242 anti bacterial agent Substances 0.000 description 10
• 229940088710 antibiotic agent Drugs 0.000 description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
• 238000001704 evaporation Methods 0.000 description 10
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• 239000012071 phase Substances 0.000 description 10
• 239000003643 water by type Substances 0.000 description 10
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
• 238000004896 high resolution mass spectrometry Methods 0.000 description 9
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 230000008878 coupling Effects 0.000 description 8
• 238000010168 coupling process Methods 0.000 description 8
• 238000005859 coupling reaction Methods 0.000 description 8
• 125000004093 cyano group Chemical group *C#N 0.000 description 8
• QWHNJUXXYKPLQM-UHFFFAOYSA-N dimethyl cyclopentane Natural products CC1(C)CCCC1 QWHNJUXXYKPLQM-UHFFFAOYSA-N 0.000 description 8
• 238000010828 elution Methods 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 8
• 239000012453 solvate Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 8
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 8
• 238000003556 assay Methods 0.000 description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
• 125000005842 heteroatom Chemical group 0.000 description 7
• 150000002431 hydrogen Chemical class 0.000 description 7
• 235000019341 magnesium sulphate Nutrition 0.000 description 7
• 239000002244 precipitate Substances 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
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• OMRPLUKQNWNZAV-CONSDPRKSA-N (6as)-3-[3-[[(6as)-2-methoxy-8-(4-methoxyphenyl)-11-oxo-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]propoxy]-8-(4-aminophenyl)-2-methoxy-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-11-one Chemical group C1=CC(OC)=CC=C1C1=CN2C(=O)C3=CC(OC)=C(OCCCOC=4C(=CC=5C(=O)N6C=C(C[C@H]6C=NC=5C=4)C=4C=CC(N)=CC=4)OC)C=C3N=C[C@@H]2C1 OMRPLUKQNWNZAV-CONSDPRKSA-N 0.000 description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
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• 125000004104 aryloxy group Chemical group 0.000 description 5
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• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
• 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 5
• VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 4
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• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
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• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
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• ZORHSASAYVIBLY-UHNVWZDZSA-N methyl (2s,4r)-4-hydroxypyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1C[C@@H](O)CN1 ZORHSASAYVIBLY-UHNVWZDZSA-N 0.000 description 4
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• ZJAMQQKWGIFYDP-LQJZCPKCSA-N (6as)-3-[5-[[(6as)-2-methoxy-8-(4-methoxyphenyl)-11-oxo-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]pentoxy]-8-(4-aminophenyl)-2-methoxy-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-11-one Chemical compound C1=CC(OC)=CC=C1C1=CN2C(=O)C3=CC(OC)=C(OCCCCCOC=4C(=CC=5C(=O)N6C=C(C[C@H]6C=NC=5C=4)C=4C=CC(N)=CC=4)OC)C=C3N=C[C@@H]2C1 ZJAMQQKWGIFYDP-LQJZCPKCSA-N 0.000 description 3
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 3
• SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 3
• 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 3
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
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