SK8552003A3 - Parenteral formulation containing epothilone analogs - Google Patents

Parenteral formulation containing epothilone analogs Download PDF

Info

Publication number: SK8552003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; group; aryl; substituted; hydrogen
Prior art date: 2001-01-25

Application number

SK855-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Rebanta Bandyopadhyay

Timothy M Malloy

Andrea Panaggio

Krishnaswamy Srinivas Raghavan

Sailesh Amilal Varia

Original Assignee

Bristol Myers Squibb Co

Priority date (The priority date 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 date listed.)

2001-01-25

Filing date

2002-01-16

Publication date

2004-06-08

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=23005123&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK8552003(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2002-01-16 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

2004-06-08 Publication of SK8552003A3 publication Critical patent/SK8552003A3/sk

Links

229930013356 epothilone Natural products 0.000 title claims abstract description 36
239000000203 mixture Substances 0.000 title claims abstract description 36
150000003883 epothilone derivatives Chemical class 0.000 title claims abstract description 35
238000009472 formulation Methods 0.000 title description 4
239000000243 solution Substances 0.000 claims abstract description 28
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 25
238000000034 method Methods 0.000 claims abstract description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
239000003085 diluting agent Substances 0.000 claims abstract description 11
BPKIGYQJPYCAOW-FFJTTWKXSA-I calcium;potassium;disodium;(2s)-2-hydroxypropanoate;dichloride;dihydroxide;hydrate Chemical group O.[OH-].[OH-].[Na+].[Na+].[Cl-].[Cl-].[K+].[Ca+2].C[C@H](O)C([O-])=O BPKIGYQJPYCAOW-FFJTTWKXSA-I 0.000 claims abstract description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
239000008389 polyethoxylated castor oil Substances 0.000 claims abstract description 7
230000008569 process Effects 0.000 claims abstract description 6
239000004094 surface-active agent Substances 0.000 claims abstract description 6
239000002736 nonionic surfactant Substances 0.000 claims abstract description 5
238000007911 parenteral administration Methods 0.000 claims abstract description 4
239000002904 solvent Substances 0.000 claims abstract 3
238000010253 intravenous injection Methods 0.000 claims abstract 2
125000000217 alkyl group Chemical group 0.000 claims description 32
125000000623 heterocyclic group Chemical group 0.000 claims description 25
125000003118 aryl group Chemical group 0.000 claims description 24
125000000547 substituted alkyl group Chemical group 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
150000002431 hydrogen Chemical class 0.000 claims description 12
125000003107 substituted aryl group Chemical group 0.000 claims description 12
239000007924 injection Substances 0.000 claims description 10
238000002347 injection Methods 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
230000000694 effects Effects 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
238000001035 drying Methods 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
238000004090 dissolution Methods 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
150000004677 hydrates Chemical class 0.000 claims 3
239000012453 solvate Substances 0.000 claims 3
238000007865 diluting Methods 0.000 claims 1
238000004806 packaging method and process Methods 0.000 claims 1
239000008156 Ringer's lactate solution Substances 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 27
-1 trifluoromethoxy, hydroxy Chemical group 0.000 description 22
206010028980 Neoplasm Diseases 0.000 description 13
239000003814 drug Substances 0.000 description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
229940079593 drug Drugs 0.000 description 9
201000010099 disease Diseases 0.000 description 8
125000004076 pyridyl group Chemical group 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
125000004568 thiomorpholinyl group Chemical group 0.000 description 8
125000003710 aryl alkyl group Chemical group 0.000 description 7
239000000047 product Substances 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
239000002254 cytotoxic agent Substances 0.000 description 6
229940127089 cytotoxic agent Drugs 0.000 description 6
238000004108 freeze drying Methods 0.000 description 6
125000001786 isothiazolyl group Chemical group 0.000 description 6
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 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
230000001093 anti-cancer Effects 0.000 description 5
239000012736 aqueous medium Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
231100000599 cytotoxic agent Toxicity 0.000 description 5
HESCAJZNRMSMJG-HGYUPSKWSA-N epothilone A Natural products O=C1[C@H](C)[C@H](O)[C@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C HESCAJZNRMSMJG-HGYUPSKWSA-N 0.000 description 5
125000005842 heteroatom Chemical group 0.000 description 5
238000001990 intravenous administration Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
102000029749 Microtubule Human genes 0.000 description 4
108091022875 Microtubule Proteins 0.000 description 4
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 description 4
239000002246 antineoplastic agent Substances 0.000 description 4
201000011510 cancer Diseases 0.000 description 4
125000001589 carboacyl group Chemical group 0.000 description 4
HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 description 4
210000004688 microtubule Anatomy 0.000 description 4
230000002062 proliferating effect Effects 0.000 description 4
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 4
230000009385 viral infection Effects 0.000 description 4
239000008215 water for injection Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
206010020751 Hypersensitivity Diseases 0.000 description 3
229930012538 Paclitaxel Natural products 0.000 description 3
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 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
230000006907 apoptotic process Effects 0.000 description 3
206010003246 arthritis Diseases 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
229960004857 mitomycin Drugs 0.000 description 3
208000015122 neurodegenerative disease Diseases 0.000 description 3
229960001592 paclitaxel Drugs 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 3
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 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 description 3
239000003981 vehicle Substances 0.000 description 3
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 description 2
208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 2
208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 2
208000032467 Aplastic anaemia Diseases 0.000 description 2
108010092160 Dactinomycin Proteins 0.000 description 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 description 2
QXRSDHAAWVKZLJ-OXZHEXMSSA-N Epothilone B Natural products O=C1[C@H](C)[C@H](O)[C@@H](C)CCC[C@@]2(C)O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C QXRSDHAAWVKZLJ-OXZHEXMSSA-N 0.000 description 2
201000008808 Fibrosarcoma Diseases 0.000 description 2
208000032612 Glial tumor Diseases 0.000 description 2
206010018338 Glioma Diseases 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
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 description 2
206010025323 Lymphomas Diseases 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 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 description 2
206010029260 Neuroblastoma Diseases 0.000 description 2
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
201000010208 Seminoma Diseases 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
208000036142 Viral infection Diseases 0.000 description 2
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 description 2
125000005236 alkanoylamino group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
229960000473 altretamine Drugs 0.000 description 2
125000001691 aryl alkyl amino group Chemical group 0.000 description 2
125000005110 aryl thio group Chemical group 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
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 description 2
125000002619 bicyclic group Chemical group 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229960004562 carboplatin Drugs 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
229960004316 cisplatin Drugs 0.000 description 2
125000000000 cycloalkoxy group Chemical group 0.000 description 2
125000006310 cycloalkyl amino group Chemical group 0.000 description 2
230000001472 cytotoxic effect Effects 0.000 description 2
229960000640 dactinomycin Drugs 0.000 description 2
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 description 2
229960000975 daunorubicin Drugs 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
QXRSDHAAWVKZLJ-PVYNADRNSA-N epothilone B Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 QXRSDHAAWVKZLJ-PVYNADRNSA-N 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
201000005787 hematologic cancer Diseases 0.000 description 2
208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 2
125000004470 heterocyclooxy group Chemical group 0.000 description 2
UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
125000001041 indolyl group Chemical group 0.000 description 2
208000017169 kidney disease Diseases 0.000 description 2
239000002609 medium Substances 0.000 description 2
201000001441 melanoma Diseases 0.000 description 2
229960001924 melphalan Drugs 0.000 description 2
SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 2
229960001428 mercaptopurine Drugs 0.000 description 2
229960000485 methotrexate Drugs 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
201000006417 multiple sclerosis Diseases 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
201000009410 rhabdomyosarcoma Diseases 0.000 description 2
241000894007 species Species 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
RCINICONZNJXQF-XAZOAEDWSA-N taxol® Chemical compound O([C@@H]1[C@@]2(CC(C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3(C21)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-XAZOAEDWSA-N 0.000 description 2
208000001608 teratocarcinoma Diseases 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
125000000335 thiazolyl group Chemical group 0.000 description 2
239000003558 transferase inhibitor Substances 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
229960003048 vinblastine Drugs 0.000 description 2
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 description 2
229960004528 vincristine Drugs 0.000 description 2
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 description 2
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 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 description 1
FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 1
102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 description 1
WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
KFXDYZXVIHNBFD-UHFFFAOYSA-N 2-(thian-2-ylsulfonyl)thiane Chemical compound C1CCCSC1S(=O)(=O)C1CCCCS1 KFXDYZXVIHNBFD-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
ZQXSFZAMFNRZOQ-UHFFFAOYSA-N 2-methylpropan-2-ol;hydrate Chemical compound O.CC(C)(C)O ZQXSFZAMFNRZOQ-UHFFFAOYSA-N 0.000 description 1
125000004635 2-oxazepinyl group Chemical group O1N(CC=CC=C1)* 0.000 description 1
125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 description 1
125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 description 1
125000004610 3,4-dihydro-4-oxo-quinazolinyl group Chemical group O=C1NC(=NC2=CC=CC=C12)* 0.000 description 1
NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
WUIABRMSWOKTOF-OYALTWQYSA-O 3-[[2-[2-[2-[[(2s,3r)-2-[[(2s,3s,4r)-4-[[(2s,3r)-2-[[6-amino-2-[(1s)-3-amino-1-[[(2s)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2r,3s,4s,5s,6s)-3-[(2r,3s,4s,5r,6r)-4-carbamoyloxy-3,5-dihydroxy-6-(hydroxymethyl)ox Chemical compound OS(O)(=O)=O.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 WUIABRMSWOKTOF-OYALTWQYSA-O 0.000 description 1
TVZGACDUOSZQKY-LBPRGKRZSA-N 4-aminofolic acid Chemical compound C1=NC2=NC(N)=NC(N)=C2N=C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 TVZGACDUOSZQKY-LBPRGKRZSA-N 0.000 description 1
125000005986 4-piperidonyl group Chemical group 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000030507 AIDS Diseases 0.000 description 1
206010065040 AIDS dementia complex Diseases 0.000 description 1
208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 1
208000010370 Adenoviridae Infections Diseases 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
108010024976 Asparaginase Proteins 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
206010003571 Astrocytoma Diseases 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
208000003950 B-cell lymphoma Diseases 0.000 description 1
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 1
108010006654 Bleomycin Proteins 0.000 description 1
201000004569 Blindness Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
FVLVBPDQNARYJU-XAHDHGMMSA-N C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O Chemical compound C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O FVLVBPDQNARYJU-XAHDHGMMSA-N 0.000 description 1
206010058019 Cancer Pain Diseases 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000010833 Chronic myeloid leukaemia Diseases 0.000 description 1
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
229930105110 Cyclosporin A Natural products 0.000 description 1
108010036949 Cyclosporine Proteins 0.000 description 1
201000003883 Cystic fibrosis Diseases 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
MWWSFMDVAYGXBV-RUELKSSGSA-N Doxorubicin hydrochloride Chemical compound Cl.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 MWWSFMDVAYGXBV-RUELKSSGSA-N 0.000 description 1
XXPXYPLPSDPERN-UHFFFAOYSA-N Ecteinascidin 743 Natural products COc1cc2C(NCCc2cc1O)C(=O)OCC3N4C(O)C5Cc6cc(C)c(OC)c(O)c6C(C4C(S)c7c(OC(=O)C)c(C)c8OCOc8c37)N5C XXPXYPLPSDPERN-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
206010053155 Epigastric discomfort Diseases 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
108010029961 Filgrastim Proteins 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
229940123414 Folate antagonist Drugs 0.000 description 1
206010016935 Follicular thyroid cancer Diseases 0.000 description 1
108700012941 GNRH1 Proteins 0.000 description 1
206010018364 Glomerulonephritis Diseases 0.000 description 1
239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 1
102100039619 Granulocyte colony-stimulating factor Human genes 0.000 description 1
102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
208000017604 Hodgkin disease Diseases 0.000 description 1
208000021519 Hodgkin lymphoma Diseases 0.000 description 1
208000010747 Hodgkins lymphoma Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
102000014150 Interferons Human genes 0.000 description 1
108010050904 Interferons Proteins 0.000 description 1
108010063738 Interleukins Proteins 0.000 description 1
102000015696 Interleukins Human genes 0.000 description 1
206010023347 Keratoacanthoma Diseases 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
JXLYSJRDGCGARV-PJXZDTQASA-N Leurosidine 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-PJXZDTQASA-N 0.000 description 1
LPGWZGMPDKDHEP-HLTPFJCJSA-N Leurosine Chemical compound C([C@]1([C@@H]2O1)CC)N(CCC=1C3=CC=CC=C3NC=11)C[C@H]2C[C@]1(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC LPGWZGMPDKDHEP-HLTPFJCJSA-N 0.000 description 1
LPGWZGMPDKDHEP-GKWAKPNHSA-N Leurosine 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@]6(CC)O[C@@H]6[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C LPGWZGMPDKDHEP-GKWAKPNHSA-N 0.000 description 1
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229930192392 Mitomycin Natural products 0.000 description 1
HRHKSTOGXBBQCB-UHFFFAOYSA-N Mitomycin E Natural products O=C1C(N)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)C3N(C)C3CN12 HRHKSTOGXBBQCB-UHFFFAOYSA-N 0.000 description 1
208000023178 Musculoskeletal disease Diseases 0.000 description 1
201000003793 Myelodysplastic syndrome Diseases 0.000 description 1
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
125000004633 N-oxo-pyridyl group Chemical group 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
ARLZGEXVMUDUQZ-UHFFFAOYSA-N O.O.[Ca] Chemical compound O.O.[Ca] ARLZGEXVMUDUQZ-UHFFFAOYSA-N 0.000 description 1
108010016076 Octreotide Proteins 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
208000001132 Osteoporosis Diseases 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
206010063837 Reperfusion injury Diseases 0.000 description 1
208000007014 Retinitis pigmentosa Diseases 0.000 description 1
230000018199 S phase Effects 0.000 description 1
229930183496 Safracin Natural products 0.000 description 1
229930190585 Saframycin Natural products 0.000 description 1
241000710960 Sindbis virus Species 0.000 description 1
206010042971 T-cell lymphoma Diseases 0.000 description 1
208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
229940123237 Taxane Drugs 0.000 description 1
FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
201000006083 Xeroderma Pigmentosum Diseases 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
JXLYSJRDGCGARV-KSNABSRWSA-N ac1l29ym 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-KSNABSRWSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
229960005310 aldesleukin Drugs 0.000 description 1
108700025316 aldesleukin Proteins 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000004075 alteration Effects 0.000 description 1
229960003896 aminopterin Drugs 0.000 description 1
206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
239000003098 androgen Substances 0.000 description 1
229940030486 androgens Drugs 0.000 description 1
208000007502 anemia Diseases 0.000 description 1
230000033115 angiogenesis Effects 0.000 description 1
239000004037 angiogenesis inhibitor Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
229940045799 anthracyclines and related substance Drugs 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000002280 anti-androgenic effect Effects 0.000 description 1
230000001772 anti-angiogenic effect Effects 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
229940046836 anti-estrogen Drugs 0.000 description 1
230000001833 anti-estrogenic effect Effects 0.000 description 1
230000000340 anti-metabolite Effects 0.000 description 1
239000000051 antiandrogen Substances 0.000 description 1
229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940125683 antiemetic agent Drugs 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940100197 antimetabolite Drugs 0.000 description 1
239000002256 antimetabolite Substances 0.000 description 1
229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 1
229940041181 antineoplastic drug Drugs 0.000 description 1
230000005775 apoptotic pathway Effects 0.000 description 1
125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
125000005239 aroylamino group Chemical group 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
125000004659 aryl alkyl thio group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000002785 azepinyl group Chemical group 0.000 description 1
150000001541 aziridines Chemical class 0.000 description 1
230000009286 beneficial effect Effects 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
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 description 1
125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 description 1
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N beta-hydroxyethanesulfonic acid Natural products OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
229960002537 betamethasone Drugs 0.000 description 1
UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical class 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 description 1
230000037396 body weight Effects 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229960002092 busulfan Drugs 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
125000004181 carboxyalkyl group Chemical group 0.000 description 1
239000003183 carcinogenic agent Substances 0.000 description 1
229930188550 carminomycin Natural products 0.000 description 1
XREUEWVEMYWFFA-CSKJXFQVSA-N carminomycin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XREUEWVEMYWFFA-CSKJXFQVSA-N 0.000 description 1
XREUEWVEMYWFFA-UHFFFAOYSA-N carminomycin I Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XREUEWVEMYWFFA-UHFFFAOYSA-N 0.000 description 1
229960005243 carmustine Drugs 0.000 description 1
229950001725 carubicin Drugs 0.000 description 1
230000022131 cell cycle Effects 0.000 description 1
230000030833 cell death Effects 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
201000004559 cerebral degeneration Diseases 0.000 description 1
210000003679 cervix uteri Anatomy 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229960004630 chlorambucil Drugs 0.000 description 1
JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 description 1
229960001265 ciclosporin Drugs 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
239000002875 cyclin dependent kinase inhibitor Substances 0.000 description 1
229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 description 1
125000005366 cycloalkylthio group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
229960004397 cyclophosphamide Drugs 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
229930182912 cyclosporin Natural products 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
229960003901 dacarbazine Drugs 0.000 description 1
230000003412 degenerative effect Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
125000004586 dihydrobenzopyranyl group Chemical group O1C(CCC2=C1C=CC=C2)* 0.000 description 1
125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 description 1
125000004597 dihydrobenzothiopyranyl group Chemical group S1C(CCC2=C1C=CC=C2)* 0.000 description 1
WOKPSXJEBSRSAT-UHFFFAOYSA-N dihydrobenzothiopyranyl sulfone group Chemical group S1C(CCC2=C1C=CC=C2)S(=O)(=O)C2SC1=C(CC2)C=CC=C1 WOKPSXJEBSRSAT-UHFFFAOYSA-N 0.000 description 1
125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
125000004609 dihydroquinazolinyl group Chemical group N1(CN=CC2=CC=CC=C12)* 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
229960003668 docetaxel Drugs 0.000 description 1
229960004679 doxorubicin Drugs 0.000 description 1
229960002918 doxorubicin hydrochloride Drugs 0.000 description 1
229940126534 drug product Drugs 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
150000003885 epothilone B derivatives Chemical class 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
229940011871 estrogen Drugs 0.000 description 1
239000000262 estrogen Substances 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
229960005420 etoposide Drugs 0.000 description 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 description 1
229960000752 etoposide phosphate Drugs 0.000 description 1
LIQODXNTTZAGID-OCBXBXKTSA-N etoposide phosphate Chemical compound COC1=C(OP(O)(O)=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 LIQODXNTTZAGID-OCBXBXKTSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
229960004177 filgrastim Drugs 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229960002949 fluorouracil Drugs 0.000 description 1
125000004615 furo[2,3-b]pyridinyl group Chemical group O1C(=CC=2C1=NC=CC2)* 0.000 description 1
125000004614 furo[3,1-b]pyridinyl group Chemical group 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 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 description 1
229960005144 gemcitabine hydrochloride Drugs 0.000 description 1
239000003862 glucocorticoid Substances 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
210000002768 hair cell Anatomy 0.000 description 1
208000014951 hematologic disease Diseases 0.000 description 1
LZWPOLSJFGLQCE-UHFFFAOYSA-N heptadecane-5,9-dione Chemical compound CCCCCCCCC(=O)CCCC(=O)CCCC LZWPOLSJFGLQCE-UHFFFAOYSA-N 0.000 description 1
125000004476 heterocycloamino group Chemical group 0.000 description 1
230000013632 homeostatic process Effects 0.000 description 1
229940125697 hormonal agent Drugs 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
230000003463 hyperproliferative effect Effects 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
229960001101 ifosfamide Drugs 0.000 description 1
HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
230000028993 immune response Effects 0.000 description 1
239000000367 immunologic factor Substances 0.000 description 1
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
229940079322 interferon Drugs 0.000 description 1
229940047122 interleukins Drugs 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229960000779 irinotecan hydrochloride Drugs 0.000 description 1
GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound Cl.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 GURKHSYORGJETM-WAQYZQTGSA-N 0.000 description 1
208000037906 ischaemic injury Diseases 0.000 description 1
125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
125000003971 isoxazolinyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000003902 lesion Effects 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
229960001614 levamisole Drugs 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
208000019423 liver disease Diseases 0.000 description 1
229960002247 lomustine Drugs 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000003120 macrolide antibiotic agent Substances 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
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229960002868 mechlorethamine hydrochloride Drugs 0.000 description 1
QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical class COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
HRHKSTOGXBBQCB-VFWICMBZSA-N methylmitomycin Chemical compound O=C1C(N)=C(C)C(=O)C2=C1[C@@H](COC(N)=O)[C@@]1(OC)[C@H]3N(C)[C@H]3CN12 HRHKSTOGXBBQCB-VFWICMBZSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
229960000350 mitotane Drugs 0.000 description 1
230000003020 moisturizing effect Effects 0.000 description 1
125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
210000002346 musculoskeletal system Anatomy 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
230000008693 nausea Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229960001494 octreotide acetate Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
201000008968 osteosarcoma Diseases 0.000 description 1
229940127084 other anti-cancer agent Drugs 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000003566 oxetanyl group Chemical group 0.000 description 1
QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229960003171 plicamycin Drugs 0.000 description 1
229950004406 porfiromycin Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000634 powder X-ray diffraction Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
229960000624 procarbazine Drugs 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
239000003528 protein farnesyltransferase inhibitor Substances 0.000 description 1
150000003195 pteridines Chemical class 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
230000004276 retinal vascularization Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
229960004641 rituximab Drugs 0.000 description 1
229960002530 sargramostim Drugs 0.000 description 1
108010038379 sargramostim Proteins 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
229960003440 semustine Drugs 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
208000002320 spinal muscular atrophy Diseases 0.000 description 1
206010041823 squamous cell carcinoma Diseases 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008227 sterile water for injection Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
229960001052 streptozocin Drugs 0.000 description 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 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
229940037128 systemic glucocorticoids Drugs 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
229940063683 taxotere Drugs 0.000 description 1
NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide 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](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
229960001278 teniposide Drugs 0.000 description 1
125000006092 tetrahydro-1,1-dioxothienyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000001730 thiiranyl group Chemical group 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 1
229940044693 topoisomerase inhibitor Drugs 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108700012359 toxins Proteins 0.000 description 1
PKVRCIRHQMSYJX-AIFWHQITSA-N trabectedin Chemical compound C([C@@]1(C(OC2)=O)NCCC3=C1C=C(C(=C3)O)OC)S[C@@H]1C3=C(OC(C)=O)C(C)=C4OCOC4=C3[C@H]2N2[C@@H](O)[C@H](CC=3C4=C(O)C(OC)=C(C)C=3)N(C)[C@H]4[C@@H]21 PKVRCIRHQMSYJX-AIFWHQITSA-N 0.000 description 1
229960000977 trabectedin Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229960001727 tretinoin Drugs 0.000 description 1
150000004654 triazenes Chemical class 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
210000003932 urinary bladder Anatomy 0.000 description 1
229960004355 vindesine Drugs 0.000 description 1
UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
229960002166 vinorelbine tartrate Drugs 0.000 description 1
GBABOYUKABKIAF-IWWDSPBFSA-N vinorelbinetartrate Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC(C23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IWWDSPBFSA-N 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oil, Petroleum & Natural Gas (AREA)
Dermatology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

SK855-2003A 2001-01-25 2002-01-16 Parenteral formulation containing epothilone analogs SK8552003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US26422801P	2001-01-25	2001-01-25
PCT/US2002/001102 WO2002062338A1 (en)	2001-01-25	2002-01-16	Parenteral formulation containing epothilone analogs

Publications (1)

Publication Number	Publication Date
SK8552003A3 true SK8552003A3 (en)	2004-06-08

Family

ID=23005123

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK855-2003A SK8552003A3 (en)	2001-01-25	2002-01-16	Parenteral formulation containing epothilone analogs

Country Status (24)

Country	Link
US (5)	US7022330B2 (pl)
EP (1)	EP1353667A1 (pl)
JP (1)	JP2004521122A (pl)
KR (1)	KR20030071853A (pl)
CN (2)	CN1489466A (pl)
AR (2)	AR032408A1 (pl)
BG (1)	BG108019A (pl)
BR (1)	BR0206511A (pl)
CA (2)	CA2434566A1 (pl)
CZ (1)	CZ20032022A3 (pl)
EE (1)	EE200300323A (pl)
HU (1)	HUP0302567A2 (pl)
IL (1)	IL156580A0 (pl)
IS (1)	IS6890A (pl)
MX (1)	MXPA03006485A (pl)
NO (1)	NO20033342L (pl)
PE (1)	PE20020733A1 (pl)
PL (1)	PL367260A1 (pl)
RU (1)	RU2003126171A (pl)
SI (1)	SI1353668T1 (pl)
SK (1)	SK8552003A3 (pl)
UY (1)	UY27134A1 (pl)
WO (1)	WO2002062338A1 (pl)
ZA (3)	ZA200305123B (pl)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6867305B2 (en)	1996-12-03	2005-03-15	Sloan-Kettering Institute For Cancer Research	Synthesis of epothilones, intermediates thereto and analogues thereof
JP4579351B2 (ja)	1996-12-03	2010-11-10	スローン−ケッタリングインスティトュートフォアキャンサーリサーチ	エポチロンの合成とその中間体及びその類似物並びにその使用
US6204388B1 (en)	1996-12-03	2001-03-20	Sloan-Kettering Institute For Cancer Research	Synthesis of epothilones, intermediates thereto and analogues thereof
US6605599B1 (en)	1997-07-08	2003-08-12	Bristol-Myers Squibb Company	Epothilone derivatives
UA75365C2 (en) *	2000-08-16	2006-04-17	Bristol Myers Squibb Co	Epothilone analog polymorph modifications, a method for obtaining thereof (variants), a pharmaceutical composition based thereon
SK8552003A3 (en) *	2001-01-25	2004-06-08	Bristol Myers Squibb Co	Parenteral formulation containing epothilone analogs
RU2003128311A (ru)	2001-02-20	2005-03-10	Бристол-Маерс Сквибб Компани (Us)	Способ лечения резистентных опухолей с применением аналогов эпотилона
HU230273B1 (hu) *	2001-03-14	2015-11-30	Bristol-Myers Squibb Company	Egy epotilon analóg és kemoterápiás szerek kombinációja proliferatív betegségek kezelésére
TW200400191A (en) *	2002-05-15	2004-01-01	Bristol Myers Squibb Co	Pharmaceutical compositions and methods of using C-21 modified epothilone derivatives
PT1506203E (pt)	2002-08-23	2007-04-30	Sloan Kettering Inst Cancer	Síntese de epotilonas, seus intermediários, seus análogos e suas utilizações
US6921769B2 (en)	2002-08-23	2005-07-26	Sloan-Kettering Institute For Cancer Research	Synthesis of epothilones, intermediates thereto and analogues thereof
US7649006B2 (en)	2002-08-23	2010-01-19	Sloan-Kettering Institute For Cancer Research	Synthesis of epothilones, intermediates thereto and analogues thereof
US20050171167A1 (en) *	2003-11-04	2005-08-04	Haby Thomas A.	Process and formulation containing epothilones and analogs thereof
US20050136105A1 (en) *	2003-12-22	2005-06-23	Allen Marni L.	Consumer customized dosage forms
CA3031283A1 (en) *	2004-01-22	2005-08-04	University Of Miami	Topical co-enzyme q10 formulations and methods of use
KR101188691B1 (ko) *	2004-10-29	2012-10-09	파르마 마르 에스.에이.	엑티나시딘 및 디사카라이드를 포함하는 제제
US20060134214A1 (en) *	2004-11-18	2006-06-22	Ismat Ullah	Enteric coated bead comprising epothilone or epothilone analog, and preparation and administration thereof
TW200631609A (en) *	2004-11-18	2006-09-16	Bristol Myers Squibb Co	Enteric coated bead comprising ixabepilone, and preparation and administration thereof
EP1674098A1 (en) *	2004-12-23	2006-06-28	Schering Aktiengesellschaft	Stable and tolerable parental formulations of highly reactive organic drug substances with low or no solubility in water
JP2008536479A (ja)	2005-02-11	2008-09-11	ユニバーシティオブサザンカリフォルニア	ジスルフィド架橋を有するタンパク質の発現法
GB0522082D0 (en)	2005-10-31	2005-12-07	Pharma Mar Sa	Formulations
US8158152B2 (en) *	2005-11-18	2012-04-17	Scidose Llc	Lyophilization process and products obtained thereby
US8008256B2 (en) *	2006-05-01	2011-08-30	University Of Southern California	Combination therapy for treatment of cancer
WO2007140299A2 (en) *	2006-05-25	2007-12-06	Bristol-Myers Squibb Company	Use of ixabepilone in combination with cyp3a4 inhibitors for pharmaceuticals
CN101732310B (zh) *	2006-07-12	2011-07-20	湖南迪诺制药有限公司	埃博霉素b的用途
TW201021855A (en) *	2008-11-13	2010-06-16	Taigen Biotechnology Co Ltd	Lyophilization formulation
US8802394B2 (en)	2008-11-13	2014-08-12	Radu O. Minea	Method of expressing proteins with disulfide bridges with enhanced yields and activity
BRPI1010576A2 (pt)	2009-05-11	2016-03-15	Berg Biosystems Llc	métodos para tratamento de distúrbios oncológicos usando transferidores epimetabólicos, moléculas intracelulares multidimensionais ou influenciadores ambientais.
CA2799202C (en)	2010-05-18	2016-07-05	Cerulean Pharma Inc.	Compositions and methods for treatment of autoimmune and other diseases
US8618146B2 (en)	2011-01-03	2013-12-31	Dr. Reddy's Laboratories Limited	Epothilone compound formulations
EP2694463B8 (en)	2011-04-04	2019-10-09	Berg LLC	Treating central nervous system tumors with coenzyme q10
WO2012170384A1 (en)	2011-06-06	2012-12-13	Chevron Phillips Chemical Company Lp	Use of metallocene compounds for cancer treatment
SG11201508272YA (en)	2013-04-08	2015-11-27	Berg Llc	Treatment of cancer using coenzyme q10 combination therapies
JP6595478B2 (ja)	2013-09-04	2019-10-23	バーグエルエルシー	コエンザイムｑ１０の連続注入によるがんの治療方法
WO2017087576A1 (en)	2015-11-16	2017-05-26	Berg Llc	Methods of treatment of temozolomide-resistant glioma using coenzyme q10
CN107041886A (zh)	2016-02-06	2017-08-15	北京华昊中天生物技术有限公司	脱环氧埃坡霉素衍生物制剂、制备及其治疗肿瘤的应用
TWI807411B (zh)	2017-04-27	2023-07-01	西班牙商瑪製藥股份有限公司	抗腫瘤化合物
BR112022013685A2 (pt)	2020-01-10	2022-09-06	R Pharm Us Operating Llc	Composições de ixabepilona
AU2021337086B2 (en)	2020-09-02	2024-02-29	Beijing Biostar Pharmaceuticals Co., Ltd.	Solid oral formulation of utidelone

Family Cites Families (55)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4950432A (en) *	1987-10-16	1990-08-21	Board Of Regents, The University Of Texas System	Polyene microlide pre-liposomal powders
DE4138042C2 (de)	1991-11-19	1993-10-14	Biotechnolog Forschung Gmbh	Epothilone, deren Herstellungsverfahren sowie diese Verbindungen enthaltende Mittel
EP1440973A3 (de)	1995-11-17	2004-10-20	Gesellschaft für biotechnologische Forschung mbH (GBF)	Epothilonderivate, Herstellung und Mittel
DE19542986A1 (de)	1995-11-17	1997-05-22	Biotechnolog Forschung Gmbh	Epothilon-Derivate und deren Verwendung
DE19639456A1 (de)	1996-09-25	1998-03-26	Biotechnolog Forschung Gmbh	Epothilon-Derivate, Herstellung und Mittel
JP3486283B2 (ja) *	1996-01-31	2004-01-13	三菱重工業株式会社	重質油の脱水方法
US6441025B2 (en)	1996-03-12	2002-08-27	Pg-Txl Company, L.P.	Water soluble paclitaxel derivatives
US5977163A (en)	1996-03-12	1999-11-02	Pg-Txl Company, L. P.	Water soluble paclitaxel prodrugs
DE19636343C1 (de)	1996-08-30	1997-10-23	Schering Ag	Zwischenprodukte innerhalb der Totalsynthese von Epothilon A und B
EP0923583A1 (de)	1996-08-30	1999-06-23	Novartis AG	Verfahren zur herstellung von epothilonen und zwischenprodukte innerhalb des verfahrens
DE19645361A1 (de)	1996-08-30	1998-04-30	Ciba Geigy Ag	Zwischenprodukte innerhalb der Totalsynthese von Epothilon A und B, Teil II
DE19645362A1 (de)	1996-10-28	1998-04-30	Ciba Geigy Ag	Verfahren zur Herstellung von Epothilon A und B und Derivaten
ES2312695T3 (es)	1996-11-18	2009-03-01	Gesellschaft Fur Biotechnologische Forschung Mbh (Gbf)	Epotilones e y f.
US6515016B2 (en)	1996-12-02	2003-02-04	Angiotech Pharmaceuticals, Inc.	Composition and methods of paclitaxel for treating psoriasis
JP4579351B2 (ja) *	1996-12-03	2010-11-10	スローン−ケッタリングインスティトュートフォアキャンサーリサーチ	エポチロンの合成とその中間体及びその類似物並びにその使用
US6204388B1 (en)	1996-12-03	2001-03-20	Sloan-Kettering Institute For Cancer Research	Synthesis of epothilones, intermediates thereto and analogues thereof
US6441186B1 (en)	1996-12-13	2002-08-27	The Scripps Research Institute	Epothilone analogs
US6380394B1 (en)	1996-12-13	2002-04-30	The Scripps Research Institute	Epothilone analogs
DE19701758A1 (de)	1997-01-20	1998-07-23	Wessjohann Ludgar A Dr	Epothilone-Synthesebausteine
DE19880193D2 (de)	1997-02-25	2000-08-24	Biotechnolog Forschung Gmbh	Seitenkettenmodifizierte Epothilone
DE19713970B4 (de)	1997-04-04	2006-08-31	R&D-Biopharmaceuticals Gmbh	Epothilone-Synthesebausteine II - Prenylderivate
WO1998047891A1 (de)	1997-04-18	1998-10-29	Studiengesellschaft Kohle Mbh	Selektive olefinmetathese von bi- oder polyfunktionellen substraten in komprimiertem kohlendioxid als reaktionsmedium
DE19821954A1 (de)	1997-05-15	1998-11-19	Biotechnolog Forschung Gmbh	Verfahren zur Herstellung eines Epothilon-Derivats
DE19720312A1 (de)	1997-05-15	1998-11-19	Hoechst Ag	Zubereitung mit erhöhter in vivo Verträglichkeit
DE19726627A1 (de)	1997-06-17	1998-12-24	Schering Ag	Zwischenprodukte, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Epothilon
US6605599B1 (en)	1997-07-08	2003-08-12	Bristol-Myers Squibb Company	Epothilone derivatives
US6384230B1 (en)	1997-07-16	2002-05-07	Schering Aktiengesellschaft	Thiazole derivatives, method for their production and use
ATE368036T1 (de)	1997-08-09	2007-08-15	Bayer Schering Pharma Ag	Neue epothilon-derivate, verfahren zu deren herstellung und ihre pharmazeutische verwendung
ES2175799T3 (es) *	1997-10-08	2002-11-16	Sepracor Inc	Forma de dosificacion para administracion en aerosol.
US6365749B1 (en)	1997-12-04	2002-04-02	Bristol-Myers Squibb Company	Process for the preparation of ring-opened epothilone intermediates which are useful for the preparation of epothilone analogs
AU1983099A (en)	1998-01-23	1999-08-09	Sanyo Electric Co., Ltd.	Reproducing method for magneto-optic recording medium, and magneto-optic disk device
HUP0101564A3 (en)	1998-02-05	2002-06-28	Novartis Ag	Compositions containing epothilone
US6683100B2 (en) *	1999-01-19	2004-01-27	Novartis Ag	Organic compounds
US6194181B1 (en)	1998-02-19	2001-02-27	Novartis Ag	Fermentative preparation process for and crystal forms of cytostatics
IL138113A0 (en)	1998-02-25	2001-10-31	Sloan Kettering Inst Cancer	Synthesis of epothilones, intermediates thereto and analogues thereof
FR2775187B1 (fr) *	1998-02-25	2003-02-21	Novartis Ag	Utilisation de l'epothilone b pour la fabrication d'une preparation pharmaceutique antiproliferative et d'une composition comprenant l'epothilone b comme agent antiproliferatif in vivo
US6380395B1 (en)	1998-04-21	2002-04-30	Bristol-Myers Squibb Company	12, 13-cyclopropane epothilone derivatives
WO2000000485A1 (de)	1998-06-30	2000-01-06	Schering Aktiengesellschaft	Epothilon-derivate, verfahren zu deren herstellung, zwischenprodukte und ihre pharmazeutische verwendung
US6303342B1 (en)	1998-11-20	2001-10-16	Kason Biosciences, Inc.	Recombinant methods and materials for producing epothilones C and D
BR9916833A (pt)	1998-12-22	2001-09-25	Novartis Ag	Derivados de epotilona e seu uso como agentes antitumor
US6780620B1 (en)	1998-12-23	2004-08-24	Bristol-Myers Squibb Company	Microbial transformation method for the preparation of an epothilone
SK11852001A3 (sk)	1999-02-18	2002-04-04	Schering Aktiengesellschaft	Deriváty epotiólonu, spôsoby ich výroby a ich farmaceutické použitie
SK287200B6 (sk)	1999-02-22	2010-03-08	Gesellschaft Fuer Biotechnologische Forschung Mbh (Gbf)	C-21 modifikované epotilóny, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a použitie
US6211412B1 (en)	1999-03-29	2001-04-03	The University Of Kansas	Synthesis of epothilones
PE20010116A1 (es)	1999-04-30	2001-02-15	Schering Ag	Derivados de 6-alquenil-, 6-alquinil- y 6-epoxi-epotilona, procedimientos para su preparacion
AU772750C (en) *	1999-04-30	2005-02-24	Schering Aktiengesellschaft	6-alkenyl-, 6-alkinyl- and 6-epoxy-epothilone derivatives, process for their production, and their use in pharmaceutical preparations
US6364749B1 (en) *	1999-09-02	2002-04-02	Micron Technology, Inc.	CMP polishing pad with hydrophilic surfaces for enhanced wetting
US6518421B1 (en)	2000-03-20	2003-02-11	Bristol-Myers Squibb Company	Process for the preparation of epothilone analogs
WO2001092255A2 (en)	2000-05-26	2001-12-06	Kosan Biosciences, Inc.	Epothilone derivatives and methods for making and using the same
UA75365C2 (en) *	2000-08-16	2006-04-17	Bristol Myers Squibb Co	Epothilone analog polymorph modifications, a method for obtaining thereof (variants), a pharmaceutical composition based thereon
US20030017169A1 (en) *	2000-12-29	2003-01-23	Sidney Pestka	Controlled release systems for polymers
WO2002058699A1 (en) *	2001-01-25	2002-08-01	Bristol-Myers Squibb Company	Pharmaceutical forms of epothilones for oral administration
SK8552003A3 (en) *	2001-01-25	2004-06-08	Bristol Myers Squibb Co	Parenteral formulation containing epothilone analogs
KR100851719B1 (ko) *	2001-01-25	2008-08-11	브리스톨-마이어스스퀴브컴파니	암 치료용 에포틸론 유사체의 투여 방법
RU2003128311A (ru)	2001-02-20	2005-03-10	Бристол-Маерс Сквибб Компани (Us)	Способ лечения резистентных опухолей с применением аналогов эпотилона

2002
- 2002-01-16 SK SK855-2003A patent/SK8552003A3/sk unknown
- 2002-01-16 RU RU2003126171/15A patent/RU2003126171A/ru not_active Application Discontinuation
- 2002-01-16 CA CA002434566A patent/CA2434566A1/en not_active Abandoned
- 2002-01-16 CZ CZ20032022A patent/CZ20032022A3/cs unknown
- 2002-01-16 EE EEP200300323A patent/EE200300323A/xx unknown
- 2002-01-16 MX MXPA03006485A patent/MXPA03006485A/es unknown
- 2002-01-16 KR KR10-2003-7009824A patent/KR20030071853A/ko not_active Withdrawn
- 2002-01-16 IL IL15658002A patent/IL156580A0/xx unknown
- 2002-01-16 CN CNA028041798A patent/CN1489466A/zh active Pending
- 2002-01-16 HU HU0302567A patent/HUP0302567A2/hu unknown
- 2002-01-16 EP EP02709040A patent/EP1353667A1/en not_active Withdrawn
- 2002-01-16 PL PL02367260A patent/PL367260A1/pl not_active Application Discontinuation
- 2002-01-16 BR BR0206511-8A patent/BR0206511A/pt not_active Application Discontinuation
- 2002-01-16 JP JP2002562345A patent/JP2004521122A/ja active Pending
- 2002-01-16 WO PCT/US2002/001102 patent/WO2002062338A1/en not_active Ceased
- 2002-01-17 US US10/051,727 patent/US7022330B2/en not_active Expired - Lifetime
- 2002-01-22 CN CN2007101422373A patent/CN101112373B/zh not_active Expired - Fee Related
- 2002-01-22 SI SI200230687T patent/SI1353668T1/sl unknown
- 2002-01-22 CA CA2681962A patent/CA2681962C/en not_active Expired - Lifetime
- 2002-01-25 AR ARP020100286A patent/AR032408A1/es unknown
- 2002-01-25 UY UY27134A patent/UY27134A1/es not_active Application Discontinuation
- 2002-01-25 PE PE2002000060A patent/PE20020733A1/es not_active Application Discontinuation
2003
- 2003-07-01 ZA ZA200305123A patent/ZA200305123B/en unknown
- 2003-07-01 ZA ZA200305126A patent/ZA200305126B/xx unknown
- 2003-07-17 ZA ZA200305536A patent/ZA200305536B/en unknown
- 2003-07-22 BG BG108019A patent/BG108019A/xx unknown
- 2003-07-24 IS IS6890A patent/IS6890A/is unknown
- 2003-07-24 NO NO20033342A patent/NO20033342L/no not_active Application Discontinuation
2005
- 2005-09-14 US US11/226,017 patent/US20060013836A1/en not_active Abandoned
2008
- 2008-11-04 US US12/264,375 patent/US8632788B2/en not_active Expired - Fee Related
2013
- 2013-12-19 US US14/134,172 patent/US20140107169A1/en not_active Abandoned
2014
- 2014-10-17 AR ARP140103915A patent/AR098109A2/es unknown
2015
- 2015-04-14 US US14/686,005 patent/US20150218179A1/en not_active Abandoned

Also Published As

Publication number	Publication date
SI1353668T1 (sl)	2008-08-31
US20090069393A1 (en)	2009-03-12
HUP0302567A2 (hu)	2003-12-29
US7022330B2 (en)	2006-04-04
ZA200305126B (en)	2004-10-01
US20020143038A1 (en)	2002-10-03
IL156580A0 (en)	2004-01-04
CZ20032022A3 (cs)	2004-04-14
EP1353667A1 (en)	2003-10-22
US20140107169A1 (en)	2014-04-17
AR098109A2 (es)	2016-05-04
CA2681962A1 (en)	2002-08-01
US20060013836A1 (en)	2006-01-19
MXPA03006485A (es)	2003-09-22
PE20020733A1 (es)	2002-08-11
ZA200305536B (en)	2004-09-06
CN101112373B (zh)	2012-06-20
CN101112373A (zh)	2008-01-30
NO20033342L (no)	2003-09-22
EE200300323A (et)	2003-10-15
US8632788B2 (en)	2014-01-21
NO20033342D0 (no)	2003-07-24
JP2004521122A (ja)	2004-07-15
CA2434566A1 (en)	2002-08-15
IS6890A (is)	2003-07-24
CA2681962C (en)	2012-06-12
WO2002062338A1 (en)	2002-08-15
BR0206511A (pt)	2003-10-21
ZA200305123B (en)	2004-10-01
AR032408A1 (es)	2003-11-05
UY27134A1 (es)	2002-08-30
BG108019A (en)	2004-09-30
CN1489466A (zh)	2004-04-14
US20150218179A1 (en)	2015-08-06
KR20030071853A (ko)	2003-09-06
RU2003126171A (ru)	2005-02-27
PL367260A1 (pl)	2005-02-21

Publication	Publication Date	Title
SK8552003A3 (en)	2004-06-08	Parenteral formulation containing epothilone analogs
US6670384B2 (en)	2003-12-30	Methods of administering epothilone analogs for the treatment of cancer
RS58203B1 (sr)	2019-03-29	Pirolobenzodiazepini i njihovi konjugati
US20040053978A1 (en)	2004-03-18	Pharmaceutical compositions and methods of using C-21 modified epothilone derivatives
AU2002245296B2 (en)	2006-12-21	Methods of administering epothilone analogs for the treatment of cancer
AU2002245296A1 (en)	2003-02-06	Methods of administering epothilone analogs for the treatment of cancer
US8871227B2 (en)	2014-10-28	Process and formulation containing epothilones and analogs thereof
AU2002243548A1 (en)	2002-08-19	Parenteral formulation containing epothilone analogs