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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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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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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|---|---|
| US (1) | US6964960B2 (enExample) |
| EP (1) | EP1303517B1 (enExample) |
| JP (1) | JP3939246B2 (enExample) |
| CN (1) | CN1183136C (enExample) |
| AR (1) | AR031379A1 (enExample) |
| AT (1) | ATE262530T1 (enExample) |
| AU (1) | AU2001279754A1 (enExample) |
| BR (1) | BR0112521A (enExample) |
| CA (1) | CA2415683C (enExample) |
| DE (1) | DE60102473T2 (enExample) |
| DK (1) | DK1303517T3 (enExample) |
| ES (1) | ES2218439T3 (enExample) |
| 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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| US6956035B2 (en) | 2001-08-31 | 2005-10-18 | Inotek Pharmaceuticals Corporation | Isoquinoline derivatives and methods of use thereof |
| CN100398519C (zh) | 2003-02-28 | 2008-07-02 | 伊诺泰克制药公司 | 四环苯甲酰胺衍生物及其用法 |
| RU2007135362A (ru) | 2005-02-25 | 2009-03-27 | Инотек Фармасьютикалз Корпорейшн (Us) | Тетрациклические амино- и карбоксамидосоединения и способ их применения |
| CN101316592A (zh) | 2005-08-24 | 2008-12-03 | 伊诺泰克制药公司 | 茚并异喹啉酮类似物及其用法 |
| EP2069351B1 (en) | 2006-06-20 | 2015-10-28 | AbbVie Inc. | 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 |
| MX2009009183A (es) | 2007-02-28 | 2009-09-07 | Inotek Pharmaceuticals Corp | Analogos de indenoisoquinolinona y metodos de utilizacion de los mismos. |
| CA2686848A1 (en) | 2007-05-08 | 2008-11-20 | Schering Corporation | Methods of treatment using intravenous formulations comprising temozolomide |
| ES2562903T3 (es) | 2011-07-13 | 2016-03-09 | Santen Pharmaceutical Co., Ltd | Nuevo compuesto que tiene actividad inhibidora de PARP |
| 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 |
| WO2017013237A1 (en) | 2015-07-23 | 2017-01-26 | Institut Curie | 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 |
| WO2019175132A1 (en) | 2018-03-13 | 2019-09-19 | Onxeo | A dbait molecule against acquired resistance in the treatment of cancer |
| US20220073531A1 (en) * | 2018-11-30 | 2022-03-10 | Merck Patent Gmbh | Compounds for electronic devices |
| 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 |
Family Cites Families (4)
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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
- 2000-07-17 GB GBGB0017508.3A patent/GB0017508D0/en not_active Ceased
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2001
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- 2001-07-13 MY MYPI20013343 patent/MY133969A/en unknown
- 2001-07-16 ES ES01957972T patent/ES2218439T3/es not_active Expired - Lifetime
- 2001-07-16 US US10/333,186 patent/US6964960B2/en not_active Expired - Fee Related
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- 2001-07-16 DE DE60102473T patent/DE60102473T2/de not_active Expired - Lifetime
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- 2001-07-16 CN CNB018126995A patent/CN1183136C/zh not_active Expired - Fee Related
- 2001-07-16 BR BR0112521-4A patent/BR0112521A/pt not_active Application Discontinuation
- 2001-07-16 TR TR2004/01026T patent/TR200401026T4/xx unknown
- 2001-07-16 JP JP2002512186A patent/JP3939246B2/ja not_active Expired - Fee Related
- 2001-07-16 EP EP01957972A patent/EP1303517B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE262530T1 (de) | 2004-04-15 |
| JP2004504323A (ja) | 2004-02-12 |
| AU2001279754A1 (en) | 2002-01-30 |
| DE60102473D1 (de) | 2004-04-29 |
| BR0112521A (pt) | 2003-07-01 |
| HK1055426A1 (en) | 2004-01-09 |
| EP1303517A1 (en) | 2003-04-23 |
| PE20020210A1 (es) | 2002-04-04 |
| HK1056872A1 (en) | 2004-03-05 |
| DK1303517T3 (da) | 2004-06-21 |
| GB0017508D0 (en) | 2000-08-30 |
| US6964960B2 (en) | 2005-11-15 |
| JP3939246B2 (ja) | 2007-07-04 |
| TR200401026T4 (tr) | 2004-07-21 |
| WO2002006284A1 (en) | 2002-01-24 |
| AR031379A1 (es) | 2003-09-24 |
| CN1441803A (zh) | 2003-09-10 |
| DE60102473T2 (de) | 2005-02-03 |
| CN1183136C (zh) | 2005-01-05 |
| CA2415683A1 (en) | 2002-01-24 |
| US20030199502A1 (en) | 2003-10-23 |
| EP1303517B1 (en) | 2004-03-24 |
| PT1303517E (pt) | 2004-07-30 |
| MY133969A (en) | 2007-11-30 |
| ES2218439T3 (es) | 2004-11-16 |
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