NO322475B1 - Tricykliske inhibitorer av poly(ADP-ribose)-polymeraser, anvendelser derav, samt et farmasoytisk materiale fremstilt derfra. - Google Patents

Info

Publication number

NO322475B1

NO322475B1 NO20020421A NO20020421A NO322475B1 NO 322475 B1 NO322475 B1 NO 322475B1 NO 20020421 A NO20020421 A NO 20020421A NO 20020421 A NO20020421 A NO 20020421A NO 322475 B1 NO322475 B1 NO 322475B1

Authority

NO

Norway

Prior art keywords

ring structure

fused ring

aromatic

alkyl

monocyclic

Prior art date

1999-08-31

Links

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• 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 title claims description 71
• 239000000463 material Substances 0.000 title claims description 16
• 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 title description 68
• 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 title description 67
• 239000003112 inhibitor Substances 0.000 title description 13
• 150000001875 compounds Chemical class 0.000 claims abstract description 197
• 230000000694 effects Effects 0.000 claims abstract description 24
• 239000003814 drug Substances 0.000 claims abstract description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 361
• 125000000217 alkyl group Chemical group 0.000 claims description 215
• 125000003118 aryl group Chemical group 0.000 claims description 196
• 229910052739 hydrogen Inorganic materials 0.000 claims description 194
• 229910052799 carbon Inorganic materials 0.000 claims description 188
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 186
• 229910052760 oxygen Inorganic materials 0.000 claims description 186
• 239000001301 oxygen Chemical group 0.000 claims description 186
• 125000005842 heteroatom Chemical group 0.000 claims description 184
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 184
• 125000002950 monocyclic group Chemical group 0.000 claims description 183
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 178
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 153
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 147
• 125000000304 alkynyl group Chemical group 0.000 claims description 147
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 133
• 125000004354 sulfur functional group Chemical group 0.000 claims description 113
• -1 nitro, cyano, amino Chemical group 0.000 claims description 96
• 229910052736 halogen Inorganic materials 0.000 claims description 70
• 150000002367 halogens Chemical class 0.000 claims description 70
• 229910052717 sulfur Chemical group 0.000 claims description 70
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 68
• 239000011593 sulfur Chemical group 0.000 claims description 64
• 125000001424 substituent group Chemical group 0.000 claims description 56
• 150000003839 salts Chemical class 0.000 claims description 54
• 239000012453 solvate Substances 0.000 claims description 41
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
• 239000003795 chemical substances by application Substances 0.000 claims description 33
• 125000003545 alkoxy group Chemical group 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
• 230000002401 inhibitory effect Effects 0.000 claims description 28
• 238000002360 preparation method Methods 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
• 125000004104 aryloxy group Chemical group 0.000 claims description 22
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 22
• 230000005764 inhibitory process Effects 0.000 claims description 20
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 102000004190 Enzymes Human genes 0.000 claims description 9
• 108090000790 Enzymes Proteins 0.000 claims description 9
• 229940079593 drug Drugs 0.000 claims description 8
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
• 238000003556 assay Methods 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 108090000623 proteins and genes Proteins 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 231100000433 cytotoxic Toxicity 0.000 claims description 5
• 230000001472 cytotoxic effect Effects 0.000 claims description 5
• 239000005864 Sulphur Chemical group 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 238000012360 testing method Methods 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 101710179684 Poly [ADP-ribose] polymerase Proteins 0.000 claims 9
• 102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 claims 9
• 230000003013 cytotoxicity Effects 0.000 claims 3
• 231100000135 cytotoxicity Toxicity 0.000 claims 3
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• 206010028980 Neoplasm Diseases 0.000 abstract description 3
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• 239000003558 transferase inhibitor Substances 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 448
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 276
• 239000007787 solid Substances 0.000 description 254
• 238000005481 NMR spectroscopy Methods 0.000 description 211
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• 238000000034 method Methods 0.000 description 134
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 110
• 239000000047 product Substances 0.000 description 88
• 238000006243 chemical reaction Methods 0.000 description 81
• 239000000243 solution Substances 0.000 description 79
• 239000002904 solvent Substances 0.000 description 79
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• 238000010898 silica gel chromatography Methods 0.000 description 51
• 229910001868 water Inorganic materials 0.000 description 50
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
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• 235000002639 sodium chloride Nutrition 0.000 description 29
• 238000005160 1H NMR spectroscopy Methods 0.000 description 28
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
• 150000004985 diamines Chemical class 0.000 description 26
• 238000004128 high performance liquid chromatography Methods 0.000 description 25
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 24
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
• 239000012044 organic layer Substances 0.000 description 22
• 150000001299 aldehydes Chemical class 0.000 description 21
• 239000000203 mixture Substances 0.000 description 21
• 238000000746 purification Methods 0.000 description 21
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
• 150000001412 amines Chemical class 0.000 description 19
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 230000035484 reaction time Effects 0.000 description 18
• 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 17
• ARDQOKBQXMKAJW-UHFFFAOYSA-N 5h-azulen-6-one Chemical compound C1=CC(=O)CC=C2C=CC=C21 ARDQOKBQXMKAJW-UHFFFAOYSA-N 0.000 description 17
• 239000012267 brine Substances 0.000 description 17
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 16
• 241000124008 Mammalia Species 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
• 239000012043 crude product Substances 0.000 description 15
• 238000004809 thin layer chromatography Methods 0.000 description 15
• XQVZDADGTFJAFM-UHFFFAOYSA-N Indole-7-carboxaldehyde Chemical compound O=CC1=CC=CC2=C1NC=C2 XQVZDADGTFJAFM-UHFFFAOYSA-N 0.000 description 14
• ZGLDQGIONSGJCN-UHFFFAOYSA-N diazepin-5-one Chemical compound O=C1C=CN=NC=C1 ZGLDQGIONSGJCN-UHFFFAOYSA-N 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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• 239000002253 acid Substances 0.000 description 11
• 150000002576 ketones Chemical class 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 235000019198 oils Nutrition 0.000 description 11
• 239000012661 PARP inhibitor Substances 0.000 description 10
• 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 10
• 229960000583 acetic acid Drugs 0.000 description 10
• 238000004440 column chromatography Methods 0.000 description 10
• 230000018109 developmental process Effects 0.000 description 10
• 238000006268 reductive amination reaction Methods 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
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• 125000001588 azulen-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C([H])C2=C1* 0.000 description 4
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
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• 238000002953 preparative HPLC Methods 0.000 description 4
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