ES2218439T3 - Indoloquinazolinonas. - Google Patents
Indoloquinazolinonas.Info
- Publication number
- ES2218439T3 ES2218439T3 ES01957972T ES01957972T ES2218439T3 ES 2218439 T3 ES2218439 T3 ES 2218439T3 ES 01957972 T ES01957972 T ES 01957972T ES 01957972 T ES01957972 T ES 01957972T ES 2218439 T3 ES2218439 T3 ES 2218439T3
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- alkyl
- atoms
- carbon
- cycloalkyl
- 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 - Lifetime
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 125000004429 atom Chemical group 0.000 claims abstract description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 30
- -1 cyano, tetrazolyl Chemical group 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
- 239000012458 free base Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims abstract description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 3
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 3
- 125000006542 morpholinylalkyl group Chemical group 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 3
- ATQUABCIJINPMX-UHFFFAOYSA-N quinazolin-5-ol Chemical compound C1=NC=C2C(O)=CC=CC2=N1 ATQUABCIJINPMX-UHFFFAOYSA-N 0.000 claims description 11
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 4
- WIVMUGHUEBLTBX-UHFFFAOYSA-N 7-(2H-tetrazol-5-ylmethyl)-6H-indole Chemical compound C=12N=CC=C2C=CCC=1CC=1N=NNN=1 WIVMUGHUEBLTBX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 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 2
- 101710179684 Poly [ADP-ribose] polymerase Proteins 0.000 claims 4
- 102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- VCRLGAIVQKJHFG-UHFFFAOYSA-N 1,6-dihydroindol-5-one Chemical compound N1C=CC2=CC(CC=C12)=O VCRLGAIVQKJHFG-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 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
- 239000012044 organic layer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000010410 reperfusion Effects 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
- 238000003756 stirring Methods 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 206010061216 Infarction Diseases 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 2
- 208000025966 Neurological disease Diseases 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 239000012661 PARP inhibitor Substances 0.000 description 2
- 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 2
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 description 2
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000003293 cardioprotective effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 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
- 239000003112 inhibitor Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 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 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- VQZRVPWIZFFSQD-UHFFFAOYSA-N 6h-quinazolin-5-one Chemical compound C1=NC=C2C(=O)CC=CC2=N1 VQZRVPWIZFFSQD-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
- 108010076525 DNA Repair Enzymes Proteins 0.000 description 1
- 102000011724 DNA Repair Enzymes Human genes 0.000 description 1
- 206010014824 Endotoxic shock Diseases 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 206010028851 Necrosis Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 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
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 150000003936 benzamides Chemical class 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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- 230000030833 cell death Effects 0.000 description 1
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- 238000006243 chemical reaction Methods 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
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- 230000007850 degeneration Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 150000002148 esters Chemical class 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 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 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- 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
- 230000002757 inflammatory effect Effects 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
- 230000000302 ischemic effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- 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
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
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- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 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
- 230000008943 replicative senescence Effects 0.000 description 1
- 208000032253 retinal ischemia Diseases 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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- 231100000827 tissue damage Toxicity 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
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- Medicinal Chemistry (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| GB0017508 | 2000-07-17 | ||
| GBGB0017508.3A GB0017508D0 (en) | 2000-07-17 | 2000-07-17 | Antimicrobials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2218439T3 true ES2218439T3 (es) | 2004-11-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01957972T Expired - Lifetime ES2218439T3 (es) | 2000-07-17 | 2001-07-16 | Indoloquinazolinonas. |
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| Country | Link |
|---|---|
| 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) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
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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
- 2001-07-16 CA CA002415683A patent/CA2415683C/en not_active Expired - Fee Related
- 2001-07-16 PT PT01957972T patent/PT1303517E/pt 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
- 2001-07-16 DK DK01957972T patent/DK1303517T3/da active
- 2001-07-16 AU AU2001279754A patent/AU2001279754A1/en not_active Abandoned
- 2001-07-16 WO PCT/EP2001/008192 patent/WO2002006284A1/en not_active Ceased
- 2001-07-16 TR TR2004/01026T patent/TR200401026T4/xx unknown
- 2001-07-16 ES ES01957972T patent/ES2218439T3/es not_active Expired - Lifetime
- 2001-07-16 BR BR0112521-4A patent/BR0112521A/pt not_active Application Discontinuation
- 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 |
| BR0112521A (pt) | 2003-07-01 |
| EP1303517A1 (en) | 2003-04-23 |
| AU2001279754A1 (en) | 2002-01-30 |
| TR200401026T4 (tr) | 2004-07-21 |
| CA2415683C (en) | 2009-12-29 |
| 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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