CA2353369A1 - Novel heteroaryl derivatives and their use as medicaments - Google Patents
Novel heteroaryl derivatives and their use as medicaments Download PDFInfo
- Publication number
- CA2353369A1 CA2353369A1 CA002353369A CA2353369A CA2353369A1 CA 2353369 A1 CA2353369 A1 CA 2353369A1 CA 002353369 A CA002353369 A CA 002353369A CA 2353369 A CA2353369 A CA 2353369A CA 2353369 A1 CA2353369 A1 CA 2353369A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- mono
- radical
- alkylamino
- aryl
- 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.)
- Abandoned
Links
- 239000003814 drug Substances 0.000 title claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 title claims description 6
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims abstract description 19
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 8
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 5
- -1 phenylethyloxy, nitro, amino Chemical group 0.000 claims description 333
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 175
- 229910052736 halogen Inorganic materials 0.000 claims description 131
- 150000002367 halogens Chemical class 0.000 claims description 131
- 125000001424 substituent group Chemical group 0.000 claims description 112
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 71
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 239000001257 hydrogen Substances 0.000 claims description 70
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 62
- 125000004043 oxo group Chemical group O=* 0.000 claims description 60
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 59
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 58
- 125000001153 fluoro group Chemical group F* 0.000 claims description 56
- 229910052731 fluorine Inorganic materials 0.000 claims description 53
- 239000011737 fluorine Substances 0.000 claims description 53
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 49
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 46
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 31
- 150000003248 quinolines Chemical class 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 22
- 241001484259 Lacuna Species 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 4
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 4
- 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- RPBWZBPLNQWXMX-UHFFFAOYSA-N [C].N1=CC=CC2=CC=CC=C21 Chemical group [C].N1=CC=CC2=CC=CC=C21 RPBWZBPLNQWXMX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 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
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims 29
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
- 206010011416 Croup infectious Diseases 0.000 claims 2
- 201000010549 croup Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- 210000004027 cell Anatomy 0.000 description 11
- 239000000203 mixture Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Natural products CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 5
- 230000001028 anti-proliverative effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- COWMQOCYJSUFSB-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)piperazine Chemical compound COC1=CC(OC)=CC(N2CCNCC2)=C1 COWMQOCYJSUFSB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 101100111947 Arabidopsis thaliana CYP72C1 gene Proteins 0.000 description 1
- 102100026189 Beta-galactosidase Human genes 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 101100439244 Glycine max CHI2-A gene Proteins 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 108010059881 Lactase Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012042 active reagent Substances 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 108010005774 beta-Galactosidase Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 201000008274 breast adenocarcinoma Diseases 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 101150071577 chi2 gene Proteins 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940116108 lactase Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
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- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SRZWJXLDVCHJGO-UHFFFAOYSA-N methyl hydrogen sulfate;10-methyl-5h-phenazine Chemical compound COS(O)(=O)=O.C1=CC=C2N(C)C3=CC=CC=C3NC2=C1 SRZWJXLDVCHJGO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000021603 oncosis Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 208000013371 ovarian adenocarcinoma Diseases 0.000 description 1
- 201000006588 ovary adenocarcinoma Diseases 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
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- 230000003389 potentiating effect Effects 0.000 description 1
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- 230000035755 proliferation Effects 0.000 description 1
- 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229940055764 triaz Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10035928.0 | 2000-07-21 | ||
| DE10035928A DE10035928A1 (de) | 2000-07-21 | 2000-07-21 | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2353369A1 true CA2353369A1 (en) | 2002-01-21 |
Family
ID=7649980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002353369A Abandoned CA2353369A1 (en) | 2000-07-21 | 2001-07-20 | Novel heteroaryl derivatives and their use as medicaments |
Country Status (23)
| Country | Link |
|---|---|
| US (5) | US6890926B2 (enExample) |
| EP (1) | EP1305290A1 (enExample) |
| JP (1) | JP2004504381A (enExample) |
| KR (1) | KR20030022287A (enExample) |
| CN (1) | CN1443171A (enExample) |
| AR (1) | AR033678A1 (enExample) |
| AU (2) | AU2001279757B2 (enExample) |
| BG (1) | BG107508A (enExample) |
| BR (1) | BR0112589A (enExample) |
| CA (1) | CA2353369A1 (enExample) |
| CZ (1) | CZ2003415A3 (enExample) |
| DE (1) | DE10035928A1 (enExample) |
| HU (1) | HUP0300838A2 (enExample) |
| IL (1) | IL153361A0 (enExample) |
| MX (1) | MXPA02012565A (enExample) |
| NO (1) | NO20030298L (enExample) |
| NZ (1) | NZ524154A (enExample) |
| PL (1) | PL358788A1 (enExample) |
| RU (1) | RU2265602C2 (enExample) |
| SK (1) | SK1842003A3 (enExample) |
| TW (1) | TWI228505B (enExample) |
| WO (1) | WO2002008192A1 (enExample) |
| ZA (1) | ZA200210180B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018033918A1 (en) * | 2016-08-18 | 2018-02-22 | Vidac Pharma Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20050092A2 (en) * | 2002-06-29 | 2005-02-28 | Zentaris Gmbh | Arylcarbonylpiperazines and heteroarylcarbonylpiperazines and the use thereof for treating benign and malignant tumour diseases |
| WO2004007470A1 (de) * | 2002-07-17 | 2004-01-22 | Zentaris Gmbh | Neue anthracen-derivate und deren verwendung als arzneimittel |
| MXPA05008099A (es) * | 2003-01-28 | 2005-09-21 | Aventis Pharma Sa | Productos n-aril-heteroaromaticos, composiciones que los contienen y su utilizacion. |
| AR044586A1 (es) * | 2003-06-04 | 2005-09-21 | Aventis Pharma Sa | Productos aril - heteroaromaticos, composiciones que los contienen y su utilizacion |
| FR2855825B1 (fr) * | 2003-06-04 | 2008-08-22 | Aventis Pharma Sa | Produits aryl-heteroaromatiques, compositions les contenant et utilisation |
| WO2005068445A2 (en) * | 2004-01-08 | 2005-07-28 | Syngenta Participations Ag | Pesticidal heterocyclic dihaloallyl compounds |
| DE102004003428A1 (de) * | 2004-01-23 | 2005-08-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue langwirksame Beta-2-Agonisten, und deren Verwendung als Arzneimittel |
| FR2871157A1 (fr) * | 2004-06-04 | 2005-12-09 | Aventis Pharma Sa | Produits biaryl aromatiques, compositions les contenant et utilisation |
| CN1830964B (zh) * | 2005-03-11 | 2011-06-15 | 中国科学院上海药物研究所 | 4-取代苯氨基-3-硝基喹啉类化合物及其制备方法和用途 |
| KR101139413B1 (ko) * | 2006-12-07 | 2012-06-22 | 차이나 메디컬 유니버시티 | 항암제로서 새로운 2-아릴-4-퀴놀론의 친수성 유도체 |
| US8835426B2 (en) * | 2007-02-26 | 2014-09-16 | Vitae Pharmaceuticals, Inc. | Cyclic urea and carbamate inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| JP5470557B2 (ja) * | 2007-07-26 | 2014-04-16 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | １１β−ヒドロキシステロイドデヒドロゲナーゼ１型の阻害剤の合成 |
| AR069207A1 (es) * | 2007-11-07 | 2010-01-06 | Vitae Pharmaceuticals Inc | Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1 |
| CA2708303A1 (en) | 2007-12-11 | 2009-06-18 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1 |
| TW200934490A (en) * | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| CA2712500A1 (en) * | 2008-01-24 | 2009-07-30 | Vitae Pharmaceuticals, Inc. | Cyclic carbazate and semicarbazide inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| CA2714532A1 (en) * | 2008-02-11 | 2009-08-20 | Vitae Pharmaceuticals, Inc. | 1,3-oxazepan-2-one and 1,3-diazepan-2-one inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1 |
| CA2715290A1 (en) * | 2008-02-15 | 2009-08-20 | Vitae Pharmaceuticals, Inc. | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| JP5538356B2 (ja) * | 2008-03-18 | 2014-07-02 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | １１β−ヒドロキシステロイドデヒドロゲナーゼ１型の阻害剤 |
| EP2300461B1 (en) * | 2008-05-01 | 2013-04-17 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| CA2723039A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2009134387A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| CA2723032A1 (en) * | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| TW201016691A (en) | 2008-07-25 | 2010-05-01 | Boehringer Ingelheim Int | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2010127237A2 (en) * | 2009-04-30 | 2010-11-04 | Boehringer Ingelheim International Gmbh | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| PL2324018T3 (pl) | 2008-07-25 | 2014-02-28 | Boehringer Ingelheim Int | Cykliczne inhibitory dehydrogenazy 11 beta-hydroksysteroidowej typu 1 |
| WO2010089303A1 (en) | 2009-02-04 | 2010-08-12 | Boehringer Ingelheim International Gmbh | CYCLIC INHIBITORS OF 11 β-HYDROXYSTEROID DEHYDROGENASE 1 |
| TW201039034A (en) * | 2009-04-27 | 2010-11-01 | Chunghwa Picture Tubes Ltd | Pixel structure and the method of forming the same |
| UA109255C2 (ru) | 2009-04-30 | 2015-08-10 | Берінгер Інгельхайм Інтернешнл Гмбх | Циклические ингибиторы 11бета-гидроксистероиддегидрогеназы 1 |
| US8927539B2 (en) | 2009-06-11 | 2015-01-06 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 based on the 1,3-oxazinan-2-one structure |
| EP2448928B1 (en) | 2009-07-01 | 2014-08-13 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2582698B1 (en) | 2010-06-16 | 2016-09-14 | Vitae Pharmaceuticals, Inc. | Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use |
| WO2011161128A1 (en) | 2010-06-25 | 2011-12-29 | Boehringer Ingelheim International Gmbh | Azaspirohexanones as inhibitors of 11-beta-hsd1 for the treatment of metabolic disorders |
| CN103179960A (zh) | 2010-11-02 | 2013-06-26 | 贝林格尔.英格海姆国际有限公司 | 治疗代谢疾病的药物组合 |
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|---|---|---|---|---|
| GR79603B (enExample) * | 1982-07-24 | 1984-10-31 | Pfizer | |
| FR2538388B1 (fr) | 1982-12-24 | 1985-06-21 | Pharmuka Lab | Nouveaux derives de naphtalene- ou azanaphtalenecarboxamide, leurs procedes de preparation et leur utilisation comme medicaments |
| EP0318235A3 (en) * | 1987-11-25 | 1991-05-02 | Takeda Chemical Industries, Ltd. | Paf antagonist, 1,4-disubstituted piperazine compounds and production thereof |
| HUT66081A (en) | 1990-10-10 | 1994-09-28 | Schering Corp | Process for preparing pyridine and pyridine n-oxide derivatives of diaryl methyl piperidines or piperazines and pharmaceutical compositions containing them |
| CA2165176A1 (en) * | 1993-06-18 | 1995-01-05 | Samuel L. Graham | Inhibitors of farnesyl-protein transferase |
| CA2256492C (en) | 1996-05-20 | 2006-04-04 | Teijin Limited | Diarylalkyl cyclic diamine derivatives as chemokine receptor antagonists |
| RU2170730C2 (ru) * | 1996-05-20 | 2001-07-20 | Дарвин Дискавери Лимитед | Хинолиновые карбоксамиды и фармацевтическая композиция на их основе |
| ATE241600T1 (de) * | 1996-06-29 | 2003-06-15 | Samjin Pharm Co Ltd | Piperazin-derivate und verfahren zu ihrer herstellung |
| US5861395A (en) | 1996-09-13 | 1999-01-19 | Schering Corporation | Compounds useful for inhibition of farnesyl proteins transferase |
| FR2753706B1 (fr) | 1996-09-20 | 1998-10-30 | Nouvelles amines cycliques n-substituees, leur procede de preparation et les compositions pharmaceutiques les renfermant | |
| KR100538152B1 (ko) * | 1997-07-07 | 2005-12-21 | 코와 가부시키가이샤 | 디아민 유도체 및 이를 함유하는 의약 |
| DE19743435A1 (de) | 1997-10-01 | 1999-04-08 | Merck Patent Gmbh | Benzamidinderivate |
| CA2342251A1 (en) * | 1998-08-28 | 2000-03-09 | Scios Inc. | Use of piperidines and/or piperazines as inhibitors of p38-alpha kinase |
| WO2000051614A1 (en) | 1999-03-03 | 2000-09-08 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferases |
| DE10035927A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| US6610274B1 (en) * | 2000-12-22 | 2003-08-26 | Wallace J. Gardner | Anti-inflammatory composition comprising tetracycline |
-
2000
- 2000-07-21 DE DE10035928A patent/DE10035928A1/de not_active Withdrawn
-
2001
- 2001-07-18 PL PL01358788A patent/PL358788A1/xx not_active Application Discontinuation
- 2001-07-18 MX MXPA02012565A patent/MXPA02012565A/es unknown
- 2001-07-18 NZ NZ524154A patent/NZ524154A/en unknown
- 2001-07-18 WO PCT/EP2001/008261 patent/WO2002008192A1/de not_active Ceased
- 2001-07-18 BR BR0112589-3A patent/BR0112589A/pt not_active IP Right Cessation
- 2001-07-18 IL IL15336101A patent/IL153361A0/xx unknown
- 2001-07-18 RU RU2003105278/04A patent/RU2265602C2/ru not_active IP Right Cessation
- 2001-07-18 CZ CZ2003415A patent/CZ2003415A3/cs unknown
- 2001-07-18 AU AU2001279757A patent/AU2001279757B2/en not_active Ceased
- 2001-07-18 CN CN01813158A patent/CN1443171A/zh active Pending
- 2001-07-18 HU HU0300838A patent/HUP0300838A2/hu unknown
- 2001-07-18 JP JP2002514099A patent/JP2004504381A/ja active Pending
- 2001-07-18 KR KR10-2003-7000707A patent/KR20030022287A/ko not_active Withdrawn
- 2001-07-18 EP EP01957978A patent/EP1305290A1/de not_active Withdrawn
- 2001-07-18 SK SK1842003A patent/SK1842003A3/sk not_active Application Discontinuation
- 2001-07-18 AU AU7975701A patent/AU7975701A/xx active Pending
- 2001-07-20 AR ARP010103481A patent/AR033678A1/es not_active Application Discontinuation
- 2001-07-20 US US09/910,141 patent/US6890926B2/en not_active Expired - Fee Related
- 2001-07-20 CA CA002353369A patent/CA2353369A1/en not_active Abandoned
- 2001-07-23 TW TW090117947A patent/TWI228505B/zh not_active IP Right Cessation
-
2002
- 2002-12-17 ZA ZA200210180A patent/ZA200210180B/xx unknown
-
2003
- 2003-01-20 NO NO20030298A patent/NO20030298L/no unknown
- 2003-01-30 BG BG107508A patent/BG107508A/bg unknown
- 2003-11-14 US US10/713,859 patent/US7056912B2/en not_active Expired - Fee Related
- 2003-12-19 US US10/741,310 patent/US6936615B2/en not_active Expired - Fee Related
-
2005
- 2005-04-14 US US11/105,622 patent/US7026310B2/en not_active Expired - Fee Related
- 2005-06-14 US US11/152,599 patent/US20050245523A1/en not_active Abandoned
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018033918A1 (en) * | 2016-08-18 | 2018-02-22 | Vidac Pharma Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
| CN109641884A (zh) * | 2016-08-18 | 2019-04-16 | 维达克制药有限公司 | 哌嗪衍生物、其药物组合物及其使用方法 |
| US11084807B2 (en) | 2016-08-18 | 2021-08-10 | Vidac Pharama Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
| CN109641884B (zh) * | 2016-08-18 | 2024-01-02 | 维达克制药有限公司 | 哌嗪衍生物、其药物组合物及其使用方法 |
| US12162868B2 (en) | 2016-08-18 | 2024-12-10 | Vidac Pharma Ltd.. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US6936615B2 (en) | 2005-08-30 |
| DE10035928A1 (de) | 2002-03-07 |
| US7056912B2 (en) | 2006-06-06 |
| US7026310B2 (en) | 2006-04-11 |
| CN1443171A (zh) | 2003-09-17 |
| US20050176744A1 (en) | 2005-08-11 |
| US6890926B2 (en) | 2005-05-10 |
| MXPA02012565A (es) | 2003-09-22 |
| NZ524154A (en) | 2005-02-25 |
| US20040132747A1 (en) | 2004-07-08 |
| EP1305290A1 (de) | 2003-05-02 |
| US20020103214A1 (en) | 2002-08-01 |
| US20040097530A1 (en) | 2004-05-20 |
| AR033678A1 (es) | 2004-01-07 |
| AU2001279757B2 (en) | 2005-05-26 |
| SK1842003A3 (en) | 2004-10-05 |
| CZ2003415A3 (cs) | 2004-05-12 |
| NO20030298D0 (no) | 2003-01-20 |
| TWI228505B (en) | 2005-03-01 |
| RU2265602C2 (ru) | 2005-12-10 |
| HUP0300838A2 (hu) | 2003-07-28 |
| US20050245523A1 (en) | 2005-11-03 |
| KR20030022287A (ko) | 2003-03-15 |
| ZA200210180B (en) | 2003-02-12 |
| BG107508A (bg) | 2003-09-30 |
| NO20030298L (no) | 2003-01-20 |
| BR0112589A (pt) | 2003-05-20 |
| PL358788A1 (en) | 2004-08-23 |
| WO2002008192A1 (de) | 2002-01-31 |
| IL153361A0 (en) | 2003-07-06 |
| JP2004504381A (ja) | 2004-02-12 |
| AU7975701A (en) | 2002-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |