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
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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
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- 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
- 210000001550 testis Anatomy 0.000 claims 1
- 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 |
|---|---|---|---|
| IN2230CH2008 | 2008-09-15 | ||
| IN2230/CHE/08 | 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 |
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| JP2012502900A JP2012502900A (ja) | 2012-02-02 |
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| EP (1) | EP2324006B1 (https=) |
| JP (1) | JP2012502900A (https=) |
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| CA (1) | CA2736732A1 (https=) |
| IL (1) | IL211366A0 (https=) |
| NZ (1) | NZ591394A (https=) |
| WO (1) | WO2010029577A2 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2424351B1 (en) * | 2009-04-27 | 2015-10-21 | Kasina Laila Innova Pharmaceuticals Private Ltd. | Anti-cancer drugs, and uses relating for malignant melanoma and other cancers |
| NO2686520T3 (https=) | 2011-06-06 | 2018-03-17 | ||
| WO2012170439A1 (en) * | 2011-06-06 | 2012-12-13 | The Ohio State University | Methods for stabilizing hypoxia inducible factor-2 alpha as a method for treating cancer |
| JP2016521747A (ja) | 2013-06-13 | 2016-07-25 | アケビア セラピューティクス インコーポレイテッドＡｋｅｂｉａ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｉｎｃ． | 貧血治療のための組成物及び方法 |
| US9593095B2 (en) | 2013-06-14 | 2017-03-14 | Duke University | Methods for the treatment of bacterial infections |
| DE112014006766T5 (de) * | 2014-06-27 | 2017-04-27 | Ecole Polytechnique Federale De Lausanne (Epfl) Epfl-Tto | Herstellung und medizinische Verwendung von Triazenen |
| US10150734B2 (en) | 2015-01-23 | 2018-12-11 | 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 |
| AU2016265922B2 (en) | 2015-05-18 | 2021-05-20 | Syn-Nat Products Enterprise LLC | A pharmaceutical co-crystal and use thereof |
| 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? |
| BR112017027285A2 (pt) | 2015-06-19 | 2018-09-11 | Syn Nat Products Entpr Llc | ?cocristal, composição farmacêutica e método para o tratamento de uma doença? |
| US10428099B2 (en) | 2015-06-25 | 2019-10-01 | Syn-Nat Products Enterprise LLC | Pharmaceutical co-crystal composition and use thereof |
| US11713298B2 (en) | 2018-05-09 | 2023-08-01 | Akebia Therapeutics, Inc. | Process for preparing 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid |
| WO2021117767A1 (ja) | 2019-12-10 | 2021-06-17 | 田辺三菱製薬株式会社 | 含窒素ヘテロアリールカルボキサミド酢酸誘導体の製造方法 |
| 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 |
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- 2009-09-14 JP JP2011526634A patent/JP2012502900A/ja active Pending
- 2009-09-14 NZ NZ591394A patent/NZ591394A/xx not_active IP Right Cessation
- 2009-09-14 CN CN200980135652.3A patent/CN102149703B/zh not_active Expired - Fee Related
- 2009-09-14 BR BRPI0913485A patent/BRPI0913485A2/pt not_active IP Right Cessation
- 2009-09-14 AU AU2009290365A patent/AU2009290365B2/en not_active Ceased
- 2009-09-14 EP EP09760623.0A patent/EP2324006B1/en not_active Not-in-force
- 2009-09-14 WO PCT/IN2009/000504 patent/WO2010029577A2/en not_active Ceased
- 2009-09-14 CA CA2736732A patent/CA2736732A1/en not_active Abandoned
- 2009-09-15 US US12/559,811 patent/US8258119B2/en not_active Expired - Fee Related
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2011
- 2011-02-23 IL IL211366A patent/IL211366A0/en unknown
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