JP2012502900A5 - - Google Patents
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- Publication number
- JP2012502900A5 JP2012502900A5 JP2011526634A JP2011526634A JP2012502900A5 JP 2012502900 A5 JP2012502900 A5 JP 2012502900A5 JP 2011526634 A JP2011526634 A JP 2011526634A JP 2011526634 A JP2011526634 A JP 2011526634A JP 2012502900 A5 JP2012502900 A5 JP 2012502900A5
- Authority
- JP
- Japan
- Prior art keywords
- diazenyl
- dimethylamino
- formula
- nhch
- carboxamide
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- -1 CF 3 Inorganic materials 0.000 claims 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical class C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 229930012538 Paclitaxel Natural products 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 229940127089 cytotoxic agent Drugs 0.000 claims 3
- 229960001592 paclitaxel Drugs 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 3
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical group CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims 2
- BRKSHTFZKOTZGD-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)thiophene-2-carboxylic acid Chemical compound CN(C)N=NC=1C=CSC=1C(O)=O BRKSHTFZKOTZGD-UHFFFAOYSA-N 0.000 claims 2
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims 2
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 230000008512 biological response Effects 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 229960003668 docetaxel Drugs 0.000 claims 2
- 238000007918 intramuscular administration Methods 0.000 claims 2
- 238000001990 intravenous administration Methods 0.000 claims 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical class C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 150000003577 thiophenes Chemical class 0.000 claims 2
- XCNVKXHFBYRXOX-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-4-methoxythiophene-2,5-dicarboxamide Chemical compound COC1=C(C(N)=O)SC(C(N)=O)=C1N=NN(C)C XCNVKXHFBYRXOX-UHFFFAOYSA-N 0.000 claims 1
- BGWLAAMXLGLLOX-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-5-nitrothiophene-2-carboxamide Chemical compound CN(C)N=NC=1C=C([N+]([O-])=O)SC=1C(N)=O BGWLAAMXLGLLOX-UHFFFAOYSA-N 0.000 claims 1
- IHXVULHYZAGNOQ-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-5-nitrothiophene-2-carboxylic acid Chemical compound CN(C)N=NC=1C=C([N+]([O-])=O)SC=1C(O)=O IHXVULHYZAGNOQ-UHFFFAOYSA-N 0.000 claims 1
- JODOHQOKFYCSLT-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-5-phenylthiophene-2-carboxamide Chemical compound S1C(C(N)=O)=C(N=NN(C)C)C=C1C1=CC=CC=C1 JODOHQOKFYCSLT-UHFFFAOYSA-N 0.000 claims 1
- FFIINGQLYOWBQU-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(O)=O)=C(N=NN(C)C)C=C1C1=CC=CC=C1 FFIINGQLYOWBQU-UHFFFAOYSA-N 0.000 claims 1
- SRONACWOWHDIFG-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-n-(2-hydroxyethyl)thiophene-2-carboxamide Chemical compound CN(C)N=NC=1C=CSC=1C(=O)NCCO SRONACWOWHDIFG-UHFFFAOYSA-N 0.000 claims 1
- AFBXRCSQERBLCD-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-n-methylthiophene-2-carboxamide Chemical compound CNC(=O)C=1SC=CC=1N=NN(C)C AFBXRCSQERBLCD-UHFFFAOYSA-N 0.000 claims 1
- JEKTZIPLXIBRFH-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)thiophene-2-carboxamide Chemical compound CN(C)N=NC=1C=CSC=1C(N)=O JEKTZIPLXIBRFH-UHFFFAOYSA-N 0.000 claims 1
- GBBZWFPJGBPQDG-UHFFFAOYSA-N 3-methyl-6-nitrothieno[2,3-d]triazin-4-one Chemical compound O=C1N(C)N=NC2=C1C=C([N+]([O-])=O)S2 GBBZWFPJGBPQDG-UHFFFAOYSA-N 0.000 claims 1
- LBSBADCUEOPGFV-UHFFFAOYSA-N 3-methyl-6-phenylthieno[3,2-d]triazin-4-one Chemical compound S1C=2C(=O)N(C)N=NC=2C=C1C1=CC=CC=C1 LBSBADCUEOPGFV-UHFFFAOYSA-N 0.000 claims 1
- MPZVKKVKDAMAKY-UHFFFAOYSA-N 3-methylthieno[2,3-d]triazin-4-one Chemical compound O=C1N(C)N=NC2=C1C=CS2 MPZVKKVKDAMAKY-UHFFFAOYSA-N 0.000 claims 1
- KMFWOYBEAVLDNW-UHFFFAOYSA-N 3-methylthieno[3,2-d]triazin-4-one Chemical compound O=C1N(C)N=NC2=C1SC=C2 KMFWOYBEAVLDNW-UHFFFAOYSA-N 0.000 claims 1
- LFITZROYUAUXCO-UHFFFAOYSA-N 4-(dimethylaminodiazenyl)thiophene-3-carboxamide Chemical compound CN(C)N=NC1=CSC=C1C(N)=O LFITZROYUAUXCO-UHFFFAOYSA-N 0.000 claims 1
- JIXFBKMQZSOWLN-UHFFFAOYSA-N 4-bromo-3-(dimethylaminodiazenyl)thiophene-2-carboxamide Chemical compound CN(C)N=NC=1C(Br)=CSC=1C(N)=O JIXFBKMQZSOWLN-UHFFFAOYSA-N 0.000 claims 1
- VNDSXZWEYBFGHD-UHFFFAOYSA-N 6-amino-3-methylthieno[2,3-d]triazin-4-one Chemical compound O=C1N(C)N=NC2=C1C=C(N)S2 VNDSXZWEYBFGHD-UHFFFAOYSA-N 0.000 claims 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims 1
- 108010006654 Bleomycin Proteins 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims 1
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 102000007644 Colony-Stimulating Factors Human genes 0.000 claims 1
- 108010071942 Colony-Stimulating Factors Proteins 0.000 claims 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
- 208000006168 Ewing Sarcoma Diseases 0.000 claims 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 claims 1
- 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 claims 1
- 102000004457 Granulocyte-Macrophage Colony-Stimulating Factor Human genes 0.000 claims 1
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 claims 1
- 102000008070 Interferon-gamma Human genes 0.000 claims 1
- 108010074328 Interferon-gamma Proteins 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 108010002352 Interleukin-1 Proteins 0.000 claims 1
- 108090000177 Interleukin-11 Proteins 0.000 claims 1
- 108010065805 Interleukin-12 Proteins 0.000 claims 1
- 108010002350 Interleukin-2 Proteins 0.000 claims 1
- 108010002335 Interleukin-9 Proteins 0.000 claims 1
- 108010063738 Interleukins Proteins 0.000 claims 1
- 102000015696 Interleukins Human genes 0.000 claims 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims 1
- 239000005411 L01XE02 - Gefitinib Substances 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 206010027480 Metastatic malignant melanoma Diseases 0.000 claims 1
- 206010031112 Oropharyngeal squamous cell carcinoma Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 claims 1
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 claims 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims 1
- 230000001919 adrenal effect Effects 0.000 claims 1
- 229940009456 adriamycin Drugs 0.000 claims 1
- 229960000548 alemtuzumab Drugs 0.000 claims 1
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 claims 1
- 229960001220 amsacrine Drugs 0.000 claims 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 229960001561 bleomycin Drugs 0.000 claims 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 229960004117 capecitabine Drugs 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 229960004562 carboplatin Drugs 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
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- 230000022534 cell killing Effects 0.000 claims 1
- 210000003679 cervix uteri Anatomy 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 229940047120 colony stimulating factors Drugs 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229960003901 dacarbazine Drugs 0.000 claims 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims 1
- 229960000975 daunorubicin Drugs 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229960004679 doxorubicin Drugs 0.000 claims 1
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 210000003238 esophagus Anatomy 0.000 claims 1
- 229960005420 etoposide Drugs 0.000 claims 1
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims 1
- 229960002949 fluorouracil Drugs 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 229960002584 gefitinib Drugs 0.000 claims 1
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims 1
- 229960005277 gemcitabine Drugs 0.000 claims 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
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- 229940022353 herceptin Drugs 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 229960003130 interferon gamma Drugs 0.000 claims 1
- 229960004768 irinotecan Drugs 0.000 claims 1
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
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- 229960001924 melphalan Drugs 0.000 claims 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims 1
- 229960001428 mercaptopurine Drugs 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 208000021039 metastatic melanoma Diseases 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- 229960004857 mitomycin Drugs 0.000 claims 1
- 239000003607 modifier Substances 0.000 claims 1
- FRBXIGJRDSLZSX-UHFFFAOYSA-N n-(2-aminoethyl)-3-(dimethylaminodiazenyl)thiophene-2-carboxamide Chemical compound CN(C)N=NC=1C=CSC=1C(=O)NCCN FRBXIGJRDSLZSX-UHFFFAOYSA-N 0.000 claims 1
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- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims 1
- 229960001756 oxaliplatin Drugs 0.000 claims 1
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- 230000001817 pituitary effect Effects 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 239000003087 receptor blocking agent Substances 0.000 claims 1
- 229960004641 rituximab Drugs 0.000 claims 1
- 208000011581 secondary neoplasm Diseases 0.000 claims 1
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- 210000000952 spleen Anatomy 0.000 claims 1
- 229960001052 streptozocin Drugs 0.000 claims 1
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 claims 1
- 229960004964 temozolomide Drugs 0.000 claims 1
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- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 1
- 229960000303 topotecan Drugs 0.000 claims 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims 1
- 229960003048 vinblastine Drugs 0.000 claims 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims 1
- 229960004528 vincristine Drugs 0.000 claims 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2230/CHE/08 | 2008-09-15 | ||
| IN2230CH2008 | 2008-09-15 | ||
| PCT/IN2009/000504 WO2010029577A2 (en) | 2008-09-15 | 2009-09-14 | Anti-cancer drugs and uses relating thereto for metastatic malignant melanoma and other cancers |
Publications (2)
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| JP2012502900A JP2012502900A (ja) | 2012-02-02 |
| JP2012502900A5 true JP2012502900A5 (https=) | 2012-10-25 |
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| JP2011526634A Pending JP2012502900A (ja) | 2008-09-15 | 2009-09-14 | 抗癌剤並びにそれに関する転移性悪性黒色腫及び他の癌についての使用 |
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| US (1) | US8258119B2 (https=) |
| EP (1) | EP2324006B1 (https=) |
| JP (1) | JP2012502900A (https=) |
| KR (1) | KR20110063537A (https=) |
| CN (1) | CN102149703B (https=) |
| AU (1) | AU2009290365B2 (https=) |
| BR (1) | BRPI0913485A2 (https=) |
| CA (1) | CA2736732A1 (https=) |
| IL (1) | IL211366A0 (https=) |
| NZ (1) | NZ591394A (https=) |
| WO (1) | WO2010029577A2 (https=) |
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| KR20120006554A (ko) * | 2009-04-27 | 2012-01-18 | 카시나 라일라 이노바 파마슈티칼스 프라이빗 리미티드 | 항암 약물, 및 악성 흑색종 및 다른 암에 대한 용도 |
| NO2686520T3 (https=) | 2011-06-06 | 2018-03-17 | ||
| EP2717870B1 (en) * | 2011-06-06 | 2017-09-27 | Akebia Therapeutics Inc. | Composition for stabilizing hypoxia inducible factor-2 alpha useful for treating cancer |
| SG10201910773VA (en) | 2013-06-13 | 2020-01-30 | Akebia Therapeutics Inc | Compositions and methods for treating anemia |
| US9593095B2 (en) | 2013-06-14 | 2017-03-14 | Duke University | Methods for the treatment of bacterial infections |
| US10221198B2 (en) | 2014-06-27 | 2019-03-05 | Ecole Polytechnique Federale De Lausanne (Epfl) | Preparation and medical use of triazenes |
| AU2016209126A1 (en) | 2015-01-23 | 2017-08-10 | Akebia Therapeutics, Inc. | Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof |
| US11324734B2 (en) | 2015-04-01 | 2022-05-10 | Akebia Therapeutics, Inc. | Compositions and methods for treating anemia |
| EP3297624B1 (en) | 2015-05-18 | 2021-03-03 | Syn-Nat Products Enterprise LLC | A pharmaceutical co-crystal and use thereof |
| KR20180018800A (ko) | 2015-06-19 | 2018-02-21 | 신-낫 프로덕츠 엔터프라이즈 엘엘씨 | 카보플라틴 계 공-결정의 약제학적 조성물 및 이의 용도 |
| BR112017027277A2 (pt) | 2015-06-19 | 2018-09-04 | Syn Nat Products Entpr Llc | ?método para o tratamento ou prevenção de uma doença e métodos para matar uma célula? |
| CA2989001A1 (en) | 2015-06-25 | 2016-12-29 | Syn-Nat Products Enterprise LLC | Pharmaceutical co-crystal composition and use thereof |
| EP3790863A1 (en) | 2018-05-09 | 2021-03-17 | Akebia Therapeutics Inc. | Process for preparing 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid |
| KR102648781B1 (ko) | 2021-11-09 | 2024-03-19 | 국립공주대학교 산학협력단 | 항암 활성을 갖는 인데노피라졸론 유도체 화합물, 그의 제조방법 및 그의 용도 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1020641B (de) | 1955-10-15 | 1957-12-12 | Basf Ag | Verfahren zur Herstellung von Derivaten der 3-Oxythiophen-2-carbonsaeure |
| CA968347A (en) | 1968-09-09 | 1975-05-27 | John F. Gerster | Substituted pyrazoles and process |
-
2009
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- 2009-09-14 NZ NZ591394A patent/NZ591394A/xx not_active IP Right Cessation
- 2009-09-14 AU AU2009290365A patent/AU2009290365B2/en not_active Ceased
- 2009-09-14 CN CN200980135652.3A patent/CN102149703B/zh not_active Expired - Fee Related
- 2009-09-14 KR KR1020117008490A patent/KR20110063537A/ko not_active Ceased
- 2009-09-14 BR BRPI0913485A patent/BRPI0913485A2/pt not_active IP Right Cessation
- 2009-09-14 CA CA2736732A patent/CA2736732A1/en not_active Abandoned
- 2009-09-14 WO PCT/IN2009/000504 patent/WO2010029577A2/en not_active Ceased
- 2009-09-14 EP EP09760623.0A patent/EP2324006B1/en not_active Not-in-force
- 2009-09-15 US US12/559,811 patent/US8258119B2/en not_active Expired - Fee Related
-
2011
- 2011-02-23 IL IL211366A patent/IL211366A0/en unknown
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