CA2415683C - Indoloquinazolinones - Google Patents
Indoloquinazolinones Download PDFInfo
- Publication number
- CA2415683C CA2415683C CA002415683A CA2415683A CA2415683C CA 2415683 C CA2415683 C CA 2415683C CA 002415683 A CA002415683 A CA 002415683A CA 2415683 A CA2415683 A CA 2415683A CA 2415683 C CA2415683 C CA 2415683C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- compound
- acid addition
- free base
- addition salt
- 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.)
- Expired - Fee Related
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- RFPSQXNAKXLFMW-UHFFFAOYSA-N pyrimido[5,4-c]carbazol-2-one Chemical class N1=C2C=CC=CC2=C2C1=CC=C1C=NC(=O)N=C12 RFPSQXNAKXLFMW-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 16
- 150000003839 salts Chemical group 0.000 claims description 14
- 239000012458 free base Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- -1 cyano, tetrazolyl Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- MUCVVURUYXBTPX-UHFFFAOYSA-N 7-(2h-tetrazol-5-ylmethyl)-6h-indolo[1,2-a]quinazolin-5-one Chemical compound C12=CC=CC=C2N2C3=CC=CC=C3C(=O)NC2=C1CC1=NN=NN1 MUCVVURUYXBTPX-UHFFFAOYSA-N 0.000 claims 1
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 70
- 239000013078 crystal Substances 0.000 description 48
- 239000007787 solid Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000012512 characterization method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OZXFNWPZRZATNT-UHFFFAOYSA-N 5-oxo-6,11-dihydrobenzo[b][1]benzazepine-6-carbonitrile Chemical compound O=C1C(C#N)C2=CC=CC=C2NC2=CC=CC=C12 OZXFNWPZRZATNT-UHFFFAOYSA-N 0.000 description 3
- JUGKQCJQHACNBE-UHFFFAOYSA-N 5-oxo-6h-benzo[b][1]benzazepine-11-carbonitrile Chemical compound O=C1CC2=CC=CC=C2N(C#N)C2=CC=CC=C12 JUGKQCJQHACNBE-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 208000010125 myocardial infarction Diseases 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
- OHBFRBSVXWHHOS-UHFFFAOYSA-N 2-(5-oxo-6h-indolo[1,2-a]quinazolin-7-yl)acetonitrile Chemical compound C1=CC=C2C(=O)NC3=C(CC#N)C4=CC=CC=C4N3C2=C1 OHBFRBSVXWHHOS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 206010061216 Infarction Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 239000012661 PARP inhibitor Substances 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010063837 Reperfusion injury Diseases 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000003293 cardioprotective effect Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical class Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000007574 infarction Effects 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 150000002826 nitrites Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000000451 tissue damage Effects 0.000 description 2
- 231100000827 tissue damage Toxicity 0.000 description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- IWGDCYSIZRGZLS-UHFFFAOYSA-N 7-ethyl-6h-indolo[1,2-a]quinazolin-5-one Chemical compound C1=CC=C2N3C4=CC=CC=C4C(CC)=C3NC(=O)C2=C1 IWGDCYSIZRGZLS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- PWJFNRJRHXWEPT-UHFFFAOYSA-N ADP ribose Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OCC(O)C(O)C(O)C=O)C(O)C1O PWJFNRJRHXWEPT-UHFFFAOYSA-N 0.000 description 1
- SRNWOUGRCWSEMX-KEOHHSTQSA-N ADP-beta-D-ribose Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C=2N=CN=C(C=2N=C1)N)OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O SRNWOUGRCWSEMX-KEOHHSTQSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010002388 Angina unstable Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010027202 Meningitis bacterial Diseases 0.000 description 1
- 206010027260 Meningitis viral Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 208000007201 Myocardial reperfusion injury Diseases 0.000 description 1
- 206010028851 Necrosis Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 description 1
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 206010064930 age-related macular degeneration Diseases 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 201000009904 bacterial meningitis Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000002612 cardiopulmonary effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- 208000037887 cell injury Diseases 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- 238000000099 in vitro assay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 208000028867 ischemia Diseases 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
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- 208000002780 macular degeneration Diseases 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000003328 mesylation reaction Methods 0.000 description 1
- LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 201000006938 muscular dystrophy Diseases 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 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 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 230000008943 replicative senescence Effects 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
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- 238000010583 slow cooling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 239000012730 sustained-release form Substances 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
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| GBGB0017508.3A GB0017508D0 (en) | 2000-07-17 | 2000-07-17 | Antimicrobials |
| GB0017508.3 | 2000-07-17 | ||
| PCT/EP2001/008192 WO2002006284A1 (en) | 2000-07-17 | 2001-07-16 | Indoloquinazolinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2415683A1 CA2415683A1 (en) | 2002-01-24 |
| CA2415683C true CA2415683C (en) | 2009-12-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002415683A Expired - Fee Related CA2415683C (en) | 2000-07-17 | 2001-07-16 | Indoloquinazolinones |
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| EP (1) | EP1303517B1 (enExample) |
| JP (1) | JP3939246B2 (enExample) |
| CN (1) | CN1183136C (enExample) |
| AR (1) | AR031379A1 (enExample) |
| AT (1) | ATE262530T1 (enExample) |
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| GB (1) | GB0017508D0 (enExample) |
| MY (1) | MY133969A (enExample) |
| PE (1) | PE20020210A1 (enExample) |
| PT (1) | PT1303517E (enExample) |
| TR (1) | TR200401026T4 (enExample) |
| WO (1) | WO2002006284A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6956035B2 (en) | 2001-08-31 | 2005-10-18 | Inotek Pharmaceuticals Corporation | Isoquinoline derivatives and methods of use thereof |
| AU2004258801A1 (en) | 2003-02-28 | 2005-02-03 | Inotek Pharmaceuticals Corporation | Tetracyclic Benzamide Derivatives and methods of use thereof |
| JP2008531562A (ja) | 2005-02-25 | 2008-08-14 | イノテック ファーマシューティカルズ コーポレイション | 四環アミノ化合物および四環カルボキサミド化合物およびこれらの使用法 |
| KR20080039508A (ko) | 2005-08-24 | 2008-05-07 | 이노텍 파마슈티컬스 코포레이션 | 인데노이소퀴놀리논 유사체 및 이의 사용 방법 |
| WO2007149907A2 (en) * | 2006-06-20 | 2007-12-27 | Abbott Laboratories | Pyrazoloquinazolinones as parp inhibitors |
| GB0615809D0 (en) * | 2006-08-09 | 2006-09-20 | Istituto Di Ricerche D Biolog | Therapeutic compounds |
| GB0701273D0 (en) * | 2007-01-24 | 2007-02-28 | Angeletti P Ist Richerche Bio | New compounds |
| JP2010520220A (ja) | 2007-02-28 | 2010-06-10 | イノテック ファーマシューティカルズ コーポレイション | インデノイソキノリノン類似体およびその使用方法 |
| WO2008140724A1 (en) | 2007-05-08 | 2008-11-20 | Schering Corporation | Methods of treatment using intravenous formulations comprising temozolomide |
| EP2733144B1 (en) * | 2011-07-13 | 2016-01-06 | Santen Pharmaceutical Co., Ltd | Novel compound having parp inhibitory activity |
| CN102766144B (zh) * | 2012-07-10 | 2014-04-23 | 浙江大学 | 一种吲哚并[1,2-c]喹唑啉化合物的制备方法 |
| AU2016296905B2 (en) | 2015-07-23 | 2018-07-05 | Centre National De La Recherche Scientifique | Use of a combination of Dbait molecule and parp inhibitors to treat cancer |
| GB201519573D0 (en) | 2015-11-05 | 2015-12-23 | King S College London | Combination |
| WO2018162439A1 (en) | 2017-03-08 | 2018-09-13 | Onxeo | New predictive biomarker for the sensitivity to a treatment of cancer with a dbait molecule |
| JP7534218B2 (ja) | 2018-03-13 | 2024-08-14 | ヴァレリオ・セラピューティクス | がんの治療における獲得耐性に対抗するｄｂａｉｔ分子 |
| KR20210097733A (ko) * | 2018-11-30 | 2021-08-09 | 메르크 파텐트 게엠베하 | 전자 디바이스용 화합물 |
| CN113544132A (zh) * | 2019-03-12 | 2021-10-22 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
| CN110357892B (zh) * | 2019-07-10 | 2022-06-07 | 云南大学 | 四氢嘧啶并[1,2-a]吲哚衍生物及其合成方法与应用 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| CN114195789B (zh) * | 2021-12-15 | 2022-09-09 | 广东海洋大学 | 一种无金属参与的多环吲哚衍生物的制备方法 |
| WO2024261243A1 (en) | 2023-06-21 | 2024-12-26 | Hemispherian As | Combination comprising a deoxycytidine derivative and a parp inhibitor for use in a method of treating hr proficient cancer |
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| US3635966A (en) | 1969-10-22 | 1972-01-18 | Robins Co Inc A H | 6-substituted-indolo(1 2-c)quinazolines |
| DE2237372C3 (de) | 1972-07-29 | 1981-07-09 | Basf Ag, 6700 Ludwigshafen | Heterocyclische Farbstoffe, ihre Herstellung und ihre Verwendung |
| US5441955A (en) | 1993-11-19 | 1995-08-15 | Pathogenesis Corporation | Indolo[2,1-biquinazoline-6,12-dione antibacterial compounds and methods of use thereof |
| GB9404485D0 (en) * | 1994-03-09 | 1994-04-20 | Cancer Res Campaign Tech | Benzamide analogues |
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2000
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- 2001-07-16 AT AT01957972T patent/ATE262530T1/de not_active IP Right Cessation
- 2001-07-16 CN CNB018126995A patent/CN1183136C/zh not_active Expired - Fee Related
- 2001-07-16 US US10/333,186 patent/US6964960B2/en not_active Expired - Fee Related
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- 2001-07-16 PT PT01957972T patent/PT1303517E/pt unknown
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- 2001-07-16 DE DE60102473T patent/DE60102473T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1183136C (zh) | 2005-01-05 |
| JP2004504323A (ja) | 2004-02-12 |
| JP3939246B2 (ja) | 2007-07-04 |
| DK1303517T3 (da) | 2004-06-21 |
| DE60102473T2 (de) | 2005-02-03 |
| ATE262530T1 (de) | 2004-04-15 |
| HK1055426A1 (en) | 2004-01-09 |
| PE20020210A1 (es) | 2002-04-04 |
| AR031379A1 (es) | 2003-09-24 |
| WO2002006284A1 (en) | 2002-01-24 |
| PT1303517E (pt) | 2004-07-30 |
| MY133969A (en) | 2007-11-30 |
| DE60102473D1 (de) | 2004-04-29 |
| ES2218439T3 (es) | 2004-11-16 |
| BR0112521A (pt) | 2003-07-01 |
| EP1303517A1 (en) | 2003-04-23 |
| AU2001279754A1 (en) | 2002-01-30 |
| TR200401026T4 (tr) | 2004-07-21 |
| HK1056872A1 (en) | 2004-03-05 |
| CN1441803A (zh) | 2003-09-10 |
| US6964960B2 (en) | 2005-11-15 |
| US20030199502A1 (en) | 2003-10-23 |
| EP1303517B1 (en) | 2004-03-24 |
| CA2415683A1 (en) | 2002-01-24 |
| GB0017508D0 (en) | 2000-08-30 |
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