JP2012525364A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012525364A5 JP2012525364A5 JP2012507812A JP2012507812A JP2012525364A5 JP 2012525364 A5 JP2012525364 A5 JP 2012525364A5 JP 2012507812 A JP2012507812 A JP 2012507812A JP 2012507812 A JP2012507812 A JP 2012507812A JP 2012525364 A5 JP2012525364 A5 JP 2012525364A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pharmaceutically acceptable
- amide
- ester
- solvate
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims description 84
- 150000001408 amides Chemical class 0.000 claims description 65
- 150000002148 esters Chemical class 0.000 claims description 63
- 239000012453 solvate Substances 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 54
- -1 amino, hydroxy, thio Chemical group 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000012636 effector Substances 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 201000011510 cancer Diseases 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- 125000005165 aryl thioxy group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 230000002062 proliferating effect Effects 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 230000000144 pharmacologic effect Effects 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229940127089 cytotoxic agent Drugs 0.000 claims description 4
- 239000002254 cytotoxic agent Substances 0.000 claims description 4
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000020084 Bone disease Diseases 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010038389 Renal cancer Diseases 0.000 claims description 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 210000001072 colon Anatomy 0.000 claims description 2
- 229960000956 coumarin Drugs 0.000 claims description 2
- 235000001671 coumarin Nutrition 0.000 claims description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- 239000000824 cytostatic agent Substances 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000893 fibroproliferative effect Effects 0.000 claims description 2
- 210000003128 head Anatomy 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 210000003734 kidney Anatomy 0.000 claims description 2
- 201000010982 kidney cancer Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 230000003211 malignant effect Effects 0.000 claims description 2
- 208000026037 malignant tumor of neck Diseases 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 210000003739 neck Anatomy 0.000 claims description 2
- 210000001672 ovary Anatomy 0.000 claims description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 2
- 210000002307 prostate Anatomy 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 210000003932 urinary bladder Anatomy 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims 2
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin 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-VTZDEGQISA-N 0.000 claims 2
- 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 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 229960005277 gemcitabine Drugs 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 2
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims 1
- YZBAXVICWUUHGG-UHFFFAOYSA-N 2-[[4-[2-[dimethyl(oxido)azaniumyl]ethylamino]-5,8-dihydroxy-9,10-dioxoanthracen-1-yl]amino]-n,n-dimethylethanamine oxide Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCC[N+](C)(C)[O-])=CC=C2NCC[N+](C)([O-])C YZBAXVICWUUHGG-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
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims 1
- HVXBOLULGPECHP-WAYWQWQTSA-N Combretastatin A4 Chemical compound C1=C(O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-WAYWQWQTSA-N 0.000 claims 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 1
- 108010092160 Dactinomycin Proteins 0.000 claims 1
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 claims 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 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
- 229930126263 Maytansine Natural products 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 229930192392 Mitomycin Natural products 0.000 claims 1
- 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 1
- 229940123237 Taxane Drugs 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
- 229940122803 Vinca alkaloid Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 claims 1
- RGHILYZRVFRRNK-UHFFFAOYSA-N anthracene-1,2-dione Chemical compound C1=CC=C2C=C(C(C(=O)C=C3)=O)C3=CC2=C1 RGHILYZRVFRRNK-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 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
- HXCHCVDVKSCDHU-LULTVBGHSA-N calicheamicin Chemical compound C1[C@H](OC)[C@@H](NCC)CO[C@H]1O[C@H]1[C@H](O[C@@H]2C\3=C(NC(=O)OC)C(=O)C[C@](C/3=C/CSSSC)(O)C#C\C=C/C#C2)O[C@H](C)[C@@H](NO[C@@H]2O[C@H](C)[C@@H](SC(=O)C=3C(=C(OC)C(O[C@H]4[C@@H]([C@H](OC)[C@@H](O)[C@H](C)O4)O)=C(I)C=3C)OC)[C@@H](O)C2)[C@@H]1O HXCHCVDVKSCDHU-LULTVBGHSA-N 0.000 claims 1
- 229930195731 calicheamicin Natural products 0.000 claims 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims 1
- 229940127093 camptothecin Drugs 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 229960004562 carboplatin Drugs 0.000 claims 1
- 230000010261 cell growth Effects 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
- 229960001338 colchicine Drugs 0.000 claims 1
- 229960005537 combretastatin A-4 Drugs 0.000 claims 1
- HVXBOLULGPECHP-UHFFFAOYSA-N combretastatin A4 Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-UHFFFAOYSA-N 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 229960004397 cyclophosphamide Drugs 0.000 claims 1
- 229960000684 cytarabine Drugs 0.000 claims 1
- 229960003901 dacarbazine Drugs 0.000 claims 1
- 229960000640 dactinomycin 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
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims 1
- 229960004679 doxorubicin Drugs 0.000 claims 1
- 229960005501 duocarmycin Drugs 0.000 claims 1
- VQNATVDKACXKTF-XELLLNAOSA-N duocarmycin Chemical compound COC1=C(OC)C(OC)=C2NC(C(=O)N3C4=CC(=O)C5=C([C@@]64C[C@@H]6C3)C=C(N5)C(=O)OC)=CC2=C1 VQNATVDKACXKTF-XELLLNAOSA-N 0.000 claims 1
- 229930184221 duocarmycin Natural products 0.000 claims 1
- 229960001904 epirubicin Drugs 0.000 claims 1
- 229930013356 epothilone Natural products 0.000 claims 1
- 150000003883 epothilone derivatives Chemical class 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
- 229960005420 etoposide Drugs 0.000 claims 1
- 229960000390 fludarabine Drugs 0.000 claims 1
- GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 claims 1
- 229960002949 fluorouracil Drugs 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004969 haloethyl group Chemical group 0.000 claims 1
- 229960001330 hydroxycarbamide Drugs 0.000 claims 1
- WKPWGQKGSOKKOO-RSFHAFMBSA-N maytansine Chemical compound CO[C@@H]([C@@]1(O)C[C@](OC(=O)N1)([C@H]([C@@H]1O[C@@]1(C)[C@@H](OC(=O)[C@H](C)N(C)C(C)=O)CC(=O)N1C)C)[H])\C=C\C=C(C)\CC2=CC(OC)=C(Cl)C1=C2 WKPWGQKGSOKKOO-RSFHAFMBSA-N 0.000 claims 1
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 claims 1
- 229960004961 mechlorethamine Drugs 0.000 claims 1
- 229960001428 mercaptopurine Drugs 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- 229960004857 mitomycin Drugs 0.000 claims 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims 1
- 229960001156 mitoxantrone Drugs 0.000 claims 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical class CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical group 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003871 sulfonates Chemical class 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims 1
- 229960003087 tioguanine Drugs 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
- 150000003672 ureas Chemical class 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 11
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 11
- RZKNKVRCIXKLBQ-UHFFFAOYSA-N 2-hydroxy-3,5-dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(O)C(C=O)=C1 RZKNKVRCIXKLBQ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 6
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- 239000000284 extract Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 230000002265 prevention Effects 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SOKPGTRDTOKLPD-UHFFFAOYSA-N 2-bromo-3,5-dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(Br)C(C=O)=C1 SOKPGTRDTOKLPD-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- 102100027417 Cytochrome P450 1B1 Human genes 0.000 description 1
- 102100026515 Cytochrome P450 2S1 Human genes 0.000 description 1
- 102100026518 Cytochrome P450 2W1 Human genes 0.000 description 1
- 102100022034 Cytochrome P450 4Z1 Human genes 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 101000725164 Homo sapiens Cytochrome P450 1B1 Proteins 0.000 description 1
- 101000855328 Homo sapiens Cytochrome P450 2S1 Proteins 0.000 description 1
- 101000855334 Homo sapiens Cytochrome P450 2W1 Proteins 0.000 description 1
- 101000896935 Homo sapiens Cytochrome P450 4Z1 Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical group OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Chemical group 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- HSSLDCABUXLXKM-UHFFFAOYSA-N resorufin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3N=C21 HSSLDCABUXLXKM-UHFFFAOYSA-N 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LURSQGOJGVDZFI-UHFFFAOYSA-N sulfino hydrogen sulfate Chemical group OS(=O)OS(O)(=O)=O LURSQGOJGVDZFI-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17488409P | 2009-05-01 | 2009-05-01 | |
| GB0907551.6 | 2009-05-01 | ||
| US61/174,884 | 2009-05-01 | ||
| GBGB0907551.6A GB0907551D0 (en) | 2009-05-01 | 2009-05-01 | Treatment or prophylaxis of proliferative conditions |
| PCT/GB2010/000860 WO2010125350A1 (en) | 2009-05-01 | 2010-04-30 | Treatment or prophylaxis of proliferative conditions |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015032957A Division JP2015117248A (ja) | 2009-05-01 | 2015-02-23 | 増殖性状態の処置または予防 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012525364A JP2012525364A (ja) | 2012-10-22 |
| JP2012525364A5 true JP2012525364A5 (https=) | 2013-06-20 |
Family
ID=40792133
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012507812A Withdrawn JP2012525364A (ja) | 2009-05-01 | 2010-04-30 | 増殖性状態の処置または予防 |
| JP2015032957A Pending JP2015117248A (ja) | 2009-05-01 | 2015-02-23 | 増殖性状態の処置または予防 |
| JP2016104884A Withdrawn JP2016153428A (ja) | 2009-05-01 | 2016-05-26 | 増殖性状態の処置または予防 |
| JP2018098050A Pending JP2018141007A (ja) | 2009-05-01 | 2018-05-22 | 増殖性状態の処置または予防 |
| JP2020173553A Withdrawn JP2021006583A (ja) | 2009-05-01 | 2020-10-14 | 増殖性状態の処置または予防 |
| JP2023010993A Withdrawn JP2023038370A (ja) | 2009-05-01 | 2023-01-27 | 増殖性状態の処置または予防 |
| JP2024192787A Pending JP2025013454A (ja) | 2009-05-01 | 2024-11-01 | 増殖性状態の処置または予防 |
| JP2025196835A Pending JP2026020235A (ja) | 2009-05-01 | 2025-11-17 | 増殖性状態の処置または予防 |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015032957A Pending JP2015117248A (ja) | 2009-05-01 | 2015-02-23 | 増殖性状態の処置または予防 |
| JP2016104884A Withdrawn JP2016153428A (ja) | 2009-05-01 | 2016-05-26 | 増殖性状態の処置または予防 |
| JP2018098050A Pending JP2018141007A (ja) | 2009-05-01 | 2018-05-22 | 増殖性状態の処置または予防 |
| JP2020173553A Withdrawn JP2021006583A (ja) | 2009-05-01 | 2020-10-14 | 増殖性状態の処置または予防 |
| JP2023010993A Withdrawn JP2023038370A (ja) | 2009-05-01 | 2023-01-27 | 増殖性状態の処置または予防 |
| JP2024192787A Pending JP2025013454A (ja) | 2009-05-01 | 2024-11-01 | 増殖性状態の処置または予防 |
| JP2025196835A Pending JP2026020235A (ja) | 2009-05-01 | 2025-11-17 | 増殖性状態の処置または予防 |
Country Status (12)
| Country | Link |
|---|---|
| US (9) | US8283340B2 (https=) |
| EP (3) | EP4691558A3 (https=) |
| JP (8) | JP2012525364A (https=) |
| KR (4) | KR20120042733A (https=) |
| CN (1) | CN102458394A (https=) |
| AU (1) | AU2010243388A1 (https=) |
| CA (1) | CA2759883C (https=) |
| ES (1) | ES3053101T3 (https=) |
| GB (1) | GB0907551D0 (https=) |
| HK (1) | HK1209056A1 (https=) |
| RU (2) | RU2019133319A (https=) |
| WO (1) | WO2010125350A1 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0907551D0 (en) * | 2009-05-01 | 2009-06-10 | Univ Dundee | Treatment or prophylaxis of proliferative conditions |
| PL223225B1 (pl) * | 2012-02-21 | 2016-10-31 | Centrum Badań Molekularnych i Makromolekularnych Polskiej Akademii Nauk | Halogenopochodne benzo[b]furanów, ewentualnie w postaci farmaceutycznie dopuszczalnej soli oraz zastosowanie halogenopochodnych benzo[b]furanów |
| CN102993157B (zh) * | 2012-11-21 | 2015-04-01 | 上海交通大学 | α-萘黄酮衍生物及其制备方法、用途 |
| CA2926771C (en) * | 2013-10-11 | 2022-07-05 | Beyondspring Pharmaceuticals, Inc. | Cancer treatment with combination of plinabulin and taxane |
| WO2015160664A1 (en) | 2014-04-15 | 2015-10-22 | Dow Agrosciences Llc | Metalloenzyme inhibitor compounds as fungicides |
| WO2015160665A1 (en) | 2014-04-15 | 2015-10-22 | Dow Agrosciences Llc | Metalloenzyme inhibitor compounds as fungicides |
| AU2016229294B2 (en) | 2015-03-06 | 2021-11-04 | Beyondspring Pharmaceuticals, Inc. | Method of treating cancer associated with a RAS mutation |
| SG11201707128TA (en) | 2015-03-06 | 2017-09-28 | Beyondspring Pharmaceuticals Inc | Method of treating a brain tumor |
| JP6969848B2 (ja) | 2015-07-13 | 2021-11-24 | ビヨンドスプリング ファーマシューティカルズ，インコーポレイテッド | プリナブリン組成物 |
| KR20180105685A (ko) | 2016-02-08 | 2018-09-28 | 비욘드스프링 파마수티컬스, 인코포레이티드. | 투카레솔 또는 이의 유사체를 함유하는 조성물 |
| JP7025416B2 (ja) | 2016-06-06 | 2022-02-24 | ビヨンドスプリング ファーマシューティカルズ，インコーポレイテッド | 好中球減少症を低減させるための組成物および方法 |
| EP3525786A4 (en) * | 2016-10-12 | 2020-03-18 | Merck Sharp & Dohme Corp. | KDM5 INHIBITORS |
| WO2018129381A1 (en) | 2017-01-06 | 2018-07-12 | Beyondspring Pharmaceuticals, Inc. | Tubulin binding compounds and therapeutic use thereof |
| BR112019015974A2 (pt) | 2017-02-01 | 2020-03-31 | Beyondspring Pharmaceuticals, Inc. | Método para reduzir neutropenia |
| KR20200112881A (ko) | 2018-01-24 | 2020-10-05 | 비욘드스프링 파마수티컬스, 인코포레이티드. | 플리나불린의 투여를 통해 혈소판감소증을 감소시키는 조성물 및 방법 |
| CA3090272A1 (en) * | 2018-02-02 | 2019-08-08 | Maverix Oncology, Inc. | Novel small molecule drug conjugates of gemcitabine derivatives |
| AU2019216531A1 (en) * | 2018-02-02 | 2020-09-24 | Maverix Oncology, Inc. | Small molecule drug conjugates of gemcitabine monophosphate |
| GR1009958B (el) * | 2019-04-24 | 2021-03-18 | ΕΝΟΡΑΣΙΣ ΑΝΩΝΥΜΗ ΕΜΠΟΡΙΚΗ ΕΤΑΙΡΕΙΑ ΦΑΡΜΑΚΕΥΤΙΚΩΝ ΚΑΙ ΙΑΤΡΙΚΩΝ ΥΛΙΚΩΝ ΚΑΙ ΜΗΧΑΝΗΜΑΤΩΝ με δ.τ. "ΕΝΟΡΑΣΙΣ Α.Ε." | Παραγωγα γεμσιταβινης και μεθοδοι δημιουργιας παραγωγων γεμσιταβινης |
| JP7739051B2 (ja) * | 2020-06-10 | 2025-09-16 | アムジエン・インコーポレーテツド | シクロブチルジヒドロキノリンスルホンアミド化合物 |
| US11691971B2 (en) | 2020-06-19 | 2023-07-04 | Incyte Corporation | Naphthyridinone compounds as JAK2 V617F inhibitors |
| WO2021257863A1 (en) | 2020-06-19 | 2021-12-23 | Incyte Corporation | Pyrrolotriazine compounds as jak2 v617f inhibitors |
| CR20230057A (es) | 2020-07-02 | 2023-08-15 | Incyte Corp | Compuestos tríciclicos de urea como inhibidores de jak2 v617f |
| US11767323B2 (en) | 2020-07-02 | 2023-09-26 | Incyte Corporation | Tricyclic pyridone compounds as JAK2 V617F inhibitors |
| US11661422B2 (en) | 2020-08-27 | 2023-05-30 | Incyte Corporation | Tricyclic urea compounds as JAK2 V617F inhibitors |
| CN112409368B (zh) * | 2020-11-23 | 2021-10-01 | 昆明医科大学 | 一类c-4位取代香豆素类化合物及其制备方法和应用 |
| US11919908B2 (en) | 2020-12-21 | 2024-03-05 | Incyte Corporation | Substituted pyrrolo[2,3-d]pyrimidine compounds as JAK2 V617F inhibitors |
| AR125273A1 (es) | 2021-02-25 | 2023-07-05 | Incyte Corp | Lactamas espirocíclicas como inhibidores de jak2 v617f |
| CA3215047A1 (en) | 2021-04-09 | 2022-10-13 | Lan Huang | Therapeutic compositions and methods for treating tumors |
| AU2023235313A1 (en) | 2022-03-17 | 2024-10-03 | Incyte Corporation | Tricyclic urea compounds as jak2 v617f inhibitors |
| TW202508560A (zh) * | 2023-08-15 | 2025-03-01 | 美商史考皮恩治療有限公司 | 製備ｐ１３ｋ抑制劑之方法 |
Family Cites Families (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU389090A1 (ru) * | 1971-05-17 | 1973-07-05 | Ташкентский государственный медицинский институт | Библиотека |
| US4526988A (en) | 1983-03-10 | 1985-07-02 | Eli Lilly And Company | Difluoro antivirals and intermediate therefor |
| US5229272A (en) | 1989-04-25 | 1993-07-20 | Igen, Inc. | Catalytic antibody components |
| EP0184365B1 (en) | 1984-12-04 | 1993-08-04 | Eli Lilly And Company | Improvements in the treatment of tumors in mammals |
| ZA859008B (en) | 1984-12-04 | 1987-07-29 | Lilly Co Eli | The treatment of tumors in mammals |
| DE3786834T2 (de) * | 1986-04-30 | 1994-03-03 | Otsuka Pharma Co Ltd | 5-Fluoro-Uracil-Derivate. |
| US6702705B1 (en) | 1988-05-04 | 2004-03-09 | Igen International, Inc. | Prodrugs activated by targeted catalytic proteins |
| JPH04501253A (ja) * | 1988-05-25 | 1992-03-05 | リサーチ コーポレーシヨン テクノロジーズ インコーポレーテツド | 抗腫瘍剤として有用なホスホラミド |
| DE3834861A1 (de) * | 1988-10-13 | 1990-04-19 | Basf Ag | Arylalkoxycumarine, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| DE3834860A1 (de) * | 1988-10-13 | 1990-04-19 | Basf Ag | Heterocyclisch substituierte alkoxycumarine, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| US6258360B1 (en) | 1989-05-04 | 2001-07-10 | Igen International, Inc. | Prodrugs activated by targeted catalytic proteins |
| US6060592A (en) | 1990-01-11 | 2000-05-09 | Isis Pharmaceuticals, Inc. | Pyrimidine nucleoside compounds and oligonucleoside compounds containing same |
| US5401838A (en) | 1992-06-22 | 1995-03-28 | Eli Lilly And Company | Stereoselective fusion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides |
| HU217779B (hu) * | 1993-06-08 | 2000-04-28 | Cancer Research Campaign Technology Limited | O6-Helyettesített guaninszármazékok, ezeket tartalmazó gyógyászati készítmények, valamint eljárás e vegyületek előállítására |
| EP0795334B1 (de) * | 1996-03-12 | 2006-02-01 | Sanofi-Aventis Deutschland GmbH | Neuartige Prodrugs für die Therapie von Tumoren und entzündlichen Erkrankungen |
| WO1998011484A1 (fr) | 1996-09-13 | 1998-03-19 | Hitachi, Ltd. | Processeur de commande a memoire d'historique |
| CA2278056C (en) | 1997-01-24 | 2006-12-12 | Norsk Hydro Asa | Gemcitabine derivatives |
| NZ330360A (en) | 1997-06-02 | 1999-03-29 | Hoffmann La Roche | 5'-deoxy-cytidine derivatives, their manufacture and use as antitumoral agents |
| TW434252B (en) | 1997-07-23 | 2001-05-16 | Univ Georgia Res Found | Process for the preparation of 2'-fluoro-5-methyl-β-L-arabino-furanosyluridine |
| JP4642226B2 (ja) | 1998-02-06 | 2011-03-02 | デ モントフォート ユニヴァーシティ | ヒドロキシル化により活性化されたプロドラッグ |
| GB2334256A (en) * | 1998-02-12 | 1999-08-18 | Univ Montfort | Hydroxylation activated prodrugs |
| WO1999040944A2 (en) | 1998-02-12 | 1999-08-19 | De Montfort University | Hydroxylation activated drug release |
| DE19834751A1 (de) | 1998-08-01 | 2000-02-03 | Boehringer Ingelheim Pharma | Disubstituierte bicyclische Heterocyclen, ihre Herstellung und ihre Verwendung als Arzneimittel |
| US6175001B1 (en) | 1998-10-16 | 2001-01-16 | The Scripps Research Institute | Functionalized pyrimidine nucleosides and nucleotides and DNA's incorporating same |
| KR100523119B1 (ko) * | 2000-03-16 | 2005-10-20 | 에프. 호프만-라 로슈 아게 | Ｉｐ 길항제로서의 카복실산 유도체 |
| GB0007401D0 (en) | 2000-03-27 | 2000-05-17 | Cancer Res Campaign Tech | Substituted chalcones as therapeeutic compounds |
| US6875751B2 (en) | 2000-06-15 | 2005-04-05 | Idenix Pharmaceuticals, Inc. | 3′-prodrugs of 2′-deoxy-β-L-nucleosides |
| US7115585B2 (en) | 2000-08-21 | 2006-10-03 | Inspire Pharmaceuticals, Inc. | Compositions for treating epithelial and retinal tissue diseases |
| JP3692927B2 (ja) | 2000-11-07 | 2005-09-07 | 日本電気株式会社 | ファクシミリ装置 |
| UA74852C2 (en) * | 2000-12-08 | 2006-02-15 | 3M Innovative Properties Co | Urea-substituted imidazoquinoline ethers |
| CA2438737A1 (en) * | 2001-03-02 | 2002-09-12 | F. Hoffmann-La Roche Ag | Alkoxycarbonylamino benzoic acid or alkoxycarbonylamino tetrazolyl phenyl derivatives as ip antagonists |
| US6780859B2 (en) * | 2001-09-14 | 2004-08-24 | Bayer Pharmaceuticals Corporation | Benzofuran and dihydrobenzofuran derivatives useful as beta-3 adrenoreceptor agonists |
| EP1300403A1 (en) * | 2001-10-02 | 2003-04-09 | Aventis Pharma S.A. | Process for the manufacture of hypoxyxylerone derivatives |
| GB0123780D0 (en) | 2001-10-03 | 2001-11-21 | Cancer Res Ventures Ltd | Substituted chalcones as therapeutic agents |
| GB0123777D0 (en) | 2001-10-03 | 2001-11-21 | Cancer Res Ventures Ltd | Substituted chalcones as therapeutic agents |
| WO2004041203A2 (en) | 2002-11-04 | 2004-05-21 | Xenoport, Inc. | Gemcitabine prodrugs, pharmaceutical compositions and uses thereof |
| CN102174038A (zh) | 2003-02-19 | 2011-09-07 | 耶鲁大学 | 用于治疗病毒感染的抗病毒核苷 |
| ZA200507752B (en) | 2003-03-28 | 2007-01-31 | Threshold Pharmaceuticals Inc | Compositions and methods for treating cancer |
| CA2548513A1 (en) * | 2003-12-04 | 2005-07-07 | Wyeth | Biaryl sulfonamides and methods for using same |
| CA2550299C (en) | 2003-12-22 | 2010-03-30 | Christopher R. Roberts | Process for fluorocytidine derivatives |
| WO2005072061A2 (en) | 2004-02-02 | 2005-08-11 | Biosight Ltd. | Conjugates for cancer therapy and diagnosis |
| US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| GB0421294D0 (en) | 2004-09-24 | 2004-10-27 | Angiogene Pharm Ltd | Bioreductively-activated prodrugs |
| CA2589850C (en) | 2004-12-17 | 2012-05-01 | Eli Lilly And Company | Amide prodrug of gemcitabine, compositions and use thereof |
| EP1676834A1 (en) * | 2004-12-30 | 2006-07-05 | Sanofi-Aventis Deutschland GmbH | Fused bicyclic carboxamide derivates for use as CXCR2 inhibitors in the treatment of inflammation |
| NO322682B1 (no) | 2005-03-18 | 2006-11-27 | Clavis Pharma Asa | Anvendelse av gemcitabinderivater for fremstilling av orale doseringsformer ved kreftbehandling, samt slike orale doseringsformer |
| EP1937658A1 (en) * | 2005-10-06 | 2008-07-02 | Sanofi-Aventis | 4-oxy-n-[1 ,3,4]-thiadiazol-2-yl-benzene sulfonamides, processes for their preparation and their use as pharmaceuticals |
| US20090069557A1 (en) | 2006-02-06 | 2009-03-12 | Dr. Reddy's Laboratories Ltd. | Preparation of gemcitabine |
| US20080004237A1 (en) | 2006-02-23 | 2008-01-03 | Tam Joemy C | Polysacchocride prodrug of 5-fluorouracil (5-FU) with enhanced target specificity for galectin-3 expressing cancers |
| US20070225248A1 (en) | 2006-03-21 | 2007-09-27 | Clavis Pharma As | Oral dosage forms of gemcitabine derivatives |
| GB0722769D0 (en) * | 2007-11-21 | 2008-01-02 | Biolipox Ab | New compounds |
| EP2136626A4 (en) | 2007-03-19 | 2011-02-23 | Oregon State | Mannich base n-oxide drugs |
| CN100475832C (zh) | 2007-05-31 | 2009-04-08 | 南京卡文迪许生物工程技术有限公司 | 一种新颖的高立体选择性合成吉西他滨工艺及中间体 |
| JO2778B1 (en) | 2007-10-16 | 2014-03-15 | ايساي انك | Certain Compounds, Compositions and Methods |
| KR20100102107A (ko) | 2007-11-06 | 2010-09-20 | 파마이센시아 코퍼레이션 | β-뉴클레오시드의 새로운 합성 방법 |
| GB0907551D0 (en) | 2009-05-01 | 2009-06-10 | Univ Dundee | Treatment or prophylaxis of proliferative conditions |
-
2009
- 2009-05-01 GB GBGB0907551.6A patent/GB0907551D0/en not_active Ceased
-
2010
- 2010-04-30 EP EP25199504.9A patent/EP4691558A3/en active Pending
- 2010-04-30 KR KR1020117026418A patent/KR20120042733A/ko not_active Ceased
- 2010-04-30 ES ES14194445T patent/ES3053101T3/es active Active
- 2010-04-30 KR KR1020217012850A patent/KR20210100598A/ko not_active Ceased
- 2010-04-30 KR KR1020177012122A patent/KR102248044B1/ko active Active
- 2010-04-30 US US12/771,923 patent/US8283340B2/en active Active - Reinstated
- 2010-04-30 EP EP10719367A patent/EP2424524A1/en not_active Withdrawn
- 2010-04-30 EP EP14194445.4A patent/EP2857018B1/en active Active
- 2010-04-30 US US13/318,321 patent/US20120190639A1/en not_active Abandoned
- 2010-04-30 JP JP2012507812A patent/JP2012525364A/ja not_active Withdrawn
- 2010-04-30 CN CN2010800288714A patent/CN102458394A/zh active Pending
- 2010-04-30 RU RU2019133319A patent/RU2019133319A/ru unknown
- 2010-04-30 WO PCT/GB2010/000860 patent/WO2010125350A1/en not_active Ceased
- 2010-04-30 KR KR1020227005644A patent/KR20220025949A/ko not_active Ceased
- 2010-04-30 RU RU2011148945A patent/RU2705548C2/ru active
- 2010-04-30 CA CA2759883A patent/CA2759883C/en active Active
- 2010-04-30 AU AU2010243388A patent/AU2010243388A1/en not_active Abandoned
-
2012
- 2012-02-28 US US13/407,436 patent/US20120302748A1/en not_active Abandoned
-
2014
- 2014-09-12 US US14/485,122 patent/US20150011512A1/en not_active Abandoned
-
2015
- 2015-02-23 JP JP2015032957A patent/JP2015117248A/ja active Pending
- 2015-10-08 HK HK15109841.5A patent/HK1209056A1/en unknown
-
2016
- 2016-05-26 JP JP2016104884A patent/JP2016153428A/ja not_active Withdrawn
-
2017
- 2017-02-06 US US15/425,758 patent/US9919060B2/en active Active
-
2018
- 2018-03-19 US US15/924,520 patent/US20190060472A1/en not_active Abandoned
- 2018-05-22 JP JP2018098050A patent/JP2018141007A/ja active Pending
-
2019
- 2019-12-11 US US16/710,711 patent/US20200360521A1/en not_active Abandoned
-
2020
- 2020-10-14 JP JP2020173553A patent/JP2021006583A/ja not_active Withdrawn
-
2021
- 2021-03-12 US US17/200,065 patent/US20220031852A1/en not_active Abandoned
-
2023
- 2023-01-27 JP JP2023010993A patent/JP2023038370A/ja not_active Withdrawn
-
2024
- 2024-11-01 US US18/934,886 patent/US20250295789A1/en active Pending
- 2024-11-01 JP JP2024192787A patent/JP2025013454A/ja active Pending
-
2025
- 2025-11-17 JP JP2025196835A patent/JP2026020235A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012525364A5 (https=) | ||
| TWI723047B (zh) | 抗真菌化合物方法 | |
| RU2019133319A (ru) | Лечение или профилактика пролиферативных состояний | |
| KR102305710B1 (ko) | Gpr84 수용체 길항제 및 이의 용도 | |
| ZA200405175B (en) | Coumarines useful as biomarkers. | |
| JP2006511587A (ja) | アデニンヌクレオチドトランスロカーゼ（ａｎｔ）リガンドならびにそれに関連する組成物および方法 | |
| UA46821C2 (uk) | Заміщені n-[(аміноімінометил або амінометил)феніл]пропіламіди, фармацевтична композиція, способи лікування та проміжні сполуки | |
| RU2011148945A (ru) | Лечение или профилактика пролиферативных состояний | |
| JP2024073414A (ja) | ゲムシタビン誘導体の新規小分子薬物コンジュゲート | |
| US20160289204A1 (en) | Griseofulvin derivatives | |
| US11135209B2 (en) | Compositions and methods for inhibiting protein kinases | |
| CA3012812A1 (en) | Heterocyclic sulfonamide derivative and medicine containing same | |
| CA2910177A1 (en) | Antibacterial phthalide derivatives | |
| US8106186B2 (en) | Transition metal phosphine complex, method for producing same, and anticancer agent containing transition metal phospine complex | |
| KR101876750B1 (ko) | 신규한 2-아민 치환 1,4-나프토퀴논 화합물 및 이를 포함하는 암의 예방 또는 치료용 약제학적 조성물 | |
| EP1897880A1 (en) | 1,3-benzothiazinone derivative and use thereof | |
| KR20200118827A (ko) | 젬시타빈 모노포스페이트의 소분자 약물 컨쥬게이트 | |
| CN106061948A (zh) | 水溶性的4‑氮杂鬼臼毒素类似物 | |
| IL262151A (en) | Processes for making oxytazine-like compounds | |
| PL239208B1 (pl) | Sposób otrzymywania pochodnych dibenzo[b,f]oksepiny | |
| JP2024512388A (ja) | 酸化ストレスに関連する状態を処置するための化合物 | |
| AU2024220205A1 (en) | Solid forms of a macrocyclic farnesyltransferase inhibitor and formulations thereof, and methods of preparing and using the macrocyclic compound and its solid forms | |
| WO2006088080A1 (ja) | シクロヘプタ［ｂ］ピリジン－３－カルボニルグアニジン誘導体およびそれを含有する医薬品 | |
| US20080096973A1 (en) | Z-stilbenes derivatives and the pharmaceutical composition thereof | |
| KR20240057820A (ko) | 신규 피라졸로-옥소티아졸리딘 유도체 및 이를 포함하는 알칼리성 포스파타제 억제제 |