HUP0300838A2 - Új heteroarilszármazékok, eljárás az előállításukra és gyógyszerként való alkalmazásuk - Google Patents
Új heteroarilszármazékok, eljárás az előállításukra és gyógyszerként való alkalmazásuk Download PDFInfo
- Publication number
- HUP0300838A2 HUP0300838A2 HU0300838A HUP0300838A HUP0300838A2 HU P0300838 A2 HUP0300838 A2 HU P0300838A2 HU 0300838 A HU0300838 A HU 0300838A HU P0300838 A HUP0300838 A HU P0300838A HU P0300838 A2 HUP0300838 A2 HU P0300838A2
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- group
- amino
- aryl
- substituted
- Prior art date
Links
- 125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 13
- 239000003814 drug Substances 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 acetyl- Chemical group 0.000 claims abstract description 369
- 125000005843 halogen group Chemical group 0.000 claims abstract description 119
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 85
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 75
- 150000003248 quinolines Chemical class 0.000 claims abstract description 28
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011593 sulfur Substances 0.000 claims abstract description 4
- 239000000654 additive Substances 0.000 claims abstract description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 3
- 150000001412 amines Chemical class 0.000 claims abstract description 3
- 239000000969 carrier Substances 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims description 248
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 196
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 71
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 62
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 60
- 125000004043 oxo group Chemical group O=* 0.000 claims description 60
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 59
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 55
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 55
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 53
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 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
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000005842 heteroatom Chemical group 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
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 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
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 2
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000546 pharmaceutical excipient Substances 0.000 abstract description 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 238000004113 cell culture Methods 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 230000004663 cell proliferation Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000002401 inhibitory effect Effects 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
- 239000007787 solid Substances 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003556 assay Methods 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
- 239000007789 gas Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 101710088194 Dehydrogenase Proteins 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
- 241000282412 Homo Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 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
- 230000001464 adherent effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000008120 corn starch Substances 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
- 229940079593 drug Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000004615 ingredient 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
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- 208000036832 Adenocarcinoma of ovary Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 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
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010061328 Ovarian epithelial cancer Diseases 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
- 239000006146 Roswell Park Memorial Institute 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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 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
- 239000000443 aerosol Substances 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
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 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
- 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
- 239000006143 cell culture medium Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002784 cytotoxicity assay Methods 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 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
- IFYLVUHLOOCYBG-UHFFFAOYSA-N eticyclidine Chemical compound C=1C=CC=CC=1C1(NCC)CCCCC1 IFYLVUHLOOCYBG-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 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
- 239000006072 paste Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
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 |
|---|---|---|---|
| DE10035928A DE10035928A1 (de) | 2000-07-21 | 2000-07-21 | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| PCT/EP2001/008261 WO2002008192A1 (de) | 2000-07-21 | 2001-07-18 | Neue heteroaryl-derivate und deren verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0300838A2 true HUP0300838A2 (hu) | 2003-07-28 |
Family
ID=7649980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0300838A HUP0300838A2 (hu) | 2000-07-21 | 2001-07-18 | Új heteroarilszármazékok, eljárás az előállításukra és gyógyszerként való alkalmazásuk |
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) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1517898A1 (de) * | 2002-06-29 | 2005-03-30 | Zentaris GmbH | Aryl- und heteroarylcarbonylpiperazine und deren verwendung zur behandlung gutartiger und b sartiger tumorerkrankungen |
| JP2005537258A (ja) * | 2002-07-17 | 2005-12-08 | ツェンタリス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規アントラセン誘導体及び医薬品としてのその使用 |
| AU2004218260A1 (en) * | 2003-01-28 | 2004-09-16 | Aventis Pharma S.A. | N-aryl heteroaromatic products, compositions containing same and use thereof |
| FR2855825B1 (fr) * | 2003-06-04 | 2008-08-22 | Aventis Pharma Sa | Produits aryl-heteroaromatiques, compositions les contenant et utilisation |
| AR044586A1 (es) * | 2003-06-04 | 2005-09-21 | Aventis Pharma Sa | Productos aril - heteroaromaticos, composiciones que los contienen y su utilizacion |
| EP1706392A2 (en) * | 2004-01-08 | 2006-10-04 | 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 |
| EP2468747B1 (en) * | 2006-12-07 | 2014-09-03 | China Medical University | 2-Selenophene-4-quinolones as anticancer agents |
| CA2678577A1 (en) * | 2007-02-26 | 2008-09-04 | Vitae Pharmaceuticals, Inc. | Cyclic urea and carbamate inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1 |
| US8575156B2 (en) * | 2007-07-26 | 2013-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| AR069207A1 (es) * | 2007-11-07 | 2010-01-06 | Vitae Pharmaceuticals Inc | Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1 |
| WO2009075835A1 (en) | 2007-12-11 | 2009-06-18 | Vitae Pharmaceutical, Inc | CYCLIC UREA INHIBITORS OF 11β-HYDROXYSTEROID DEHYDROGENASE 1 |
| TW200934490A (en) * | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| JP5490020B2 (ja) * | 2008-01-24 | 2014-05-14 | 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の環状カルバゼート及びセミカルバジドインヒビター |
| EP2252598A2 (en) * | 2008-02-11 | 2010-11-24 | Vitae Pharmaceuticals, Inc. | 1,3-oxazepan-2-one and 1,3-diazepan-2-one inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| US8598160B2 (en) * | 2008-02-15 | 2013-12-03 | Vitae Pharmaceuticals, Inc. | Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| CA2718264A1 (en) * | 2008-03-18 | 2009-09-24 | Vitae Pharmaceuticals, Inc. | Inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| EP2291373B1 (en) * | 2008-05-01 | 2013-09-11 | 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 |
| NZ588954A (en) | 2008-05-01 | 2012-08-31 | Vitae Pharmaceuticals Inc | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| TW201004945A (en) | 2008-05-01 | 2010-02-01 | 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 |
| CN104327062A (zh) | 2008-07-25 | 2015-02-04 | 贝林格尔·英格海姆国际有限公司 | 11β-羟基类固醇脱氢酶1的环状抑制剂 |
| EP2393807B1 (en) | 2009-02-04 | 2013-08-14 | Boehringer Ingelheim International GmbH | Cyclic inhibitors of 11 -hydroxysteroid dehydrogenase 1 |
| TW201039034A (en) * | 2009-04-27 | 2010-11-01 | Chunghwa Picture Tubes Ltd | Pixel structure and the method of forming the same |
| MA33216B1 (fr) | 2009-04-30 | 2012-04-02 | Boehringer Ingelheim Int | Inhibiteurs cycliques de la 11béta-hydroxysteroïde déshydrogénase 1 |
| GEP20156309B (en) * | 2009-04-30 | 2015-07-10 | Vitae Pharmaceuticals Inc | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2011011123A1 (en) | 2009-06-11 | 2011-01-27 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-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 |
| JP5860042B2 (ja) | 2010-06-16 | 2016-02-16 | 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 | 置換５、６及び７員複素環、そのような化合物を含有する医薬及びそれらの使用 |
| EP2585444B1 (en) | 2010-06-25 | 2014-10-22 | Boehringer Ingelheim International GmbH | Azaspirohexanones as inhibitors of 11-beta-hsd1 for the treatment of metabolic disorders |
| EA201300522A1 (ru) | 2010-11-02 | 2013-11-29 | Бёрингер Ингельхайм Интернациональ Гмбх | Фармацевтические комбинации для лечения метаболических нарушений |
| JP7471818B2 (ja) * | 2016-08-18 | 2024-04-22 | ヴィダック ファーマ リミテッド | ピペラジン誘導体、医薬組成物、及びその使用方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656174A (en) * | 1982-07-24 | 1987-04-07 | Pfizer Inc. | Quinoline therapeutic agents |
| 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 |
| US4937246A (en) * | 1987-11-25 | 1990-06-26 | 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 |
| WO1997044329A1 (en) | 1996-05-20 | 1997-11-27 | Teijin Limited | Diarylalkyl cyclic diamine derivatives as chemokine receptor antagonists |
| TR199802385T2 (xx) * | 1996-05-20 | 1999-04-21 | Darwin Discovery Limited | TNF inhibit�rleri ve FDE-IV inhibit�rleri olarak kinolin karboksamidler. |
| DE69722360T2 (de) * | 1996-06-29 | 2003-11-27 | Samjin Pharm, Co. | 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 | |
| DE69827233T2 (de) * | 1997-07-07 | 2005-03-24 | Kowa Co., Ltd., Nagoya | Diaminderivate und diese enthaltende arzneimittel |
| DE19743435A1 (de) | 1997-10-01 | 1999-04-08 | Merck Patent Gmbh | Benzamidinderivate |
| IL141724A0 (en) * | 1998-08-28 | 2002-03-10 | Scios Inc | INHIBITORS OF P38-α KINASE |
| JP2002538121A (ja) | 1999-03-03 | 2002-11-12 | メルク エンド カムパニー インコーポレーテッド | プレニルタンパク質トランスフェラーゼの阻害剤 |
| 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 WO PCT/EP2001/008261 patent/WO2002008192A1/de not_active Ceased
- 2001-07-18 NZ NZ524154A patent/NZ524154A/en unknown
- 2001-07-18 BR BR0112589-3A patent/BR0112589A/pt not_active IP Right Cessation
- 2001-07-18 CN CN01813158A patent/CN1443171A/zh active Pending
- 2001-07-18 CZ CZ2003415A patent/CZ2003415A3/cs unknown
- 2001-07-18 AU AU2001279757A patent/AU2001279757B2/en not_active Ceased
- 2001-07-18 AU AU7975701A patent/AU7975701A/xx active Pending
- 2001-07-18 SK SK1842003A patent/SK1842003A3/sk not_active Application Discontinuation
- 2001-07-18 RU RU2003105278/04A patent/RU2265602C2/ru not_active IP Right Cessation
- 2001-07-18 MX MXPA02012565A patent/MXPA02012565A/es unknown
- 2001-07-18 IL IL15336101A patent/IL153361A0/xx unknown
- 2001-07-18 PL PL01358788A patent/PL358788A1/xx not_active Application Discontinuation
- 2001-07-18 JP JP2002514099A patent/JP2004504381A/ja active Pending
- 2001-07-18 EP EP01957978A patent/EP1305290A1/de not_active Withdrawn
- 2001-07-18 KR KR10-2003-7000707A patent/KR20030022287A/ko not_active Withdrawn
- 2001-07-18 HU HU0300838A patent/HUP0300838A2/hu unknown
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| NO20030298D0 (no) | 2003-01-20 |
| MXPA02012565A (es) | 2003-09-22 |
| RU2265602C2 (ru) | 2005-12-10 |
| US20050176744A1 (en) | 2005-08-11 |
| JP2004504381A (ja) | 2004-02-12 |
| US7056912B2 (en) | 2006-06-06 |
| EP1305290A1 (de) | 2003-05-02 |
| US20050245523A1 (en) | 2005-11-03 |
| WO2002008192A1 (de) | 2002-01-31 |
| ZA200210180B (en) | 2003-02-12 |
| AU7975701A (en) | 2002-02-05 |
| SK1842003A3 (en) | 2004-10-05 |
| DE10035928A1 (de) | 2002-03-07 |
| US7026310B2 (en) | 2006-04-11 |
| BG107508A (bg) | 2003-09-30 |
| CN1443171A (zh) | 2003-09-17 |
| US6936615B2 (en) | 2005-08-30 |
| BR0112589A (pt) | 2003-05-20 |
| CA2353369A1 (en) | 2002-01-21 |
| US6890926B2 (en) | 2005-05-10 |
| IL153361A0 (en) | 2003-07-06 |
| TWI228505B (en) | 2005-03-01 |
| US20040132747A1 (en) | 2004-07-08 |
| AR033678A1 (es) | 2004-01-07 |
| NO20030298L (no) | 2003-01-20 |
| US20020103214A1 (en) | 2002-08-01 |
| NZ524154A (en) | 2005-02-25 |
| AU2001279757B2 (en) | 2005-05-26 |
| US20040097530A1 (en) | 2004-05-20 |
| KR20030022287A (ko) | 2003-03-15 |
| CZ2003415A3 (cs) | 2004-05-12 |
| PL358788A1 (en) | 2004-08-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HUP0300838A2 (hu) | Új heteroarilszármazékok, eljárás az előállításukra és gyógyszerként való alkalmazásuk | |
| RU2267488C2 (ru) | Производные акридина, способ их получения и фармацевтическая композиция на их основе | |
| KR20030015894A (ko) | 신규한 헤테로아릴 유도체 및 약물로서의 이의 용도 | |
| EP1224172A1 (en) | Drugs for the treatment of malignant tumours | |
| HUP0204458A2 (hu) | Alfa-2-antagonista hatású kinolinszármazékok és ezeket tartalmazó gyógyszerkészítmények | |
| EP1939195A1 (de) | Neue Indolderivate und deren Verwendung als Arzneimittel | |
| US12324803B2 (en) | 3-(hydroxy)-pyridin-4(1H)-one compounds and methods of making and using the same | |
| JPH10511385A (ja) | 多薬剤耐性のモジュレーターとしてのピペラジン−２，５−ジオン誘導体 | |
| CA2859156C (en) | Treatment of type i and type ii diabetes | |
| CN109503478B (zh) | 2,3-二氢-1h-喹啉-4-酮类缩氨基硫脲衍生物及其制备方法和应用 | |
| RU2240313C2 (ru) | Лекарственные средства для лечения злокачественных опухолей | |
| WO2024148293A1 (en) | Charged pi-conjugated molecules for the treatment of microbial infections | |
| HK1057548A (en) | Novel heteroaryl derivatives and the use thereof as pharmaceuticals | |
| HK1058202A (en) | Novel heteroaryl derivatives and use thereof as medicaments | |
| JPH1029985A (ja) | 新規ニトロキノキサリンジオン誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD9A | Lapse of provisional protection due to non-payment of fees |