NO328500B1 - Polymorfer av en epothilon-analog - Google Patents
Polymorfer av en epothilon-analog Download PDFInfo
- Publication number
- NO328500B1 NO328500B1 NO20030707A NO20030707A NO328500B1 NO 328500 B1 NO328500 B1 NO 328500B1 NO 20030707 A NO20030707 A NO 20030707A NO 20030707 A NO20030707 A NO 20030707A NO 328500 B1 NO328500 B1 NO 328500B1
- Authority
- NO
- Norway
- Prior art keywords
- approx
- solution
- hours
- formula
- mixture
- Prior art date
Links
- 229930013356 epothilone Natural products 0.000 title claims description 33
- 150000003883 epothilone derivatives Chemical class 0.000 title claims description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 89
- 239000013078 crystal Substances 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 38
- 239000002002 slurry Substances 0.000 claims description 35
- 239000000243 solution Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 21
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- 229910016523 CuKa Inorganic materials 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000001237 Raman spectrum Methods 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 230000002062 proliferating effect Effects 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000002178 crystalline material Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims 2
- 229920000053 polysorbate 80 Polymers 0.000 claims 2
- 229940068968 polysorbate 80 Drugs 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 235000019439 ethyl acetate Nutrition 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 208000035475 disorder Diseases 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000013014 purified material Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 230000006907 apoptotic process Effects 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 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 3
- 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 3
- LZWPOLSJFGLQCE-UHFFFAOYSA-N heptadecane-5,9-dione Chemical compound CCCCCCCCC(=O)CCCC(=O)CCCC LZWPOLSJFGLQCE-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 208000015122 neurodegenerative disease Diseases 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-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
- 206010025323 Lymphomas Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010029260 Neuroblastoma Diseases 0.000 description 2
- 229930012538 Paclitaxel Natural products 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
- 208000036142 Viral infection Diseases 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- LNAMMBFJMYMQTO-FNEBRGMMSA-N chloroform;(1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].ClC(Cl)Cl.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 LNAMMBFJMYMQTO-FNEBRGMMSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 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 2
- 239000000706 filtrate Substances 0.000 description 2
- 201000005787 hematologic cancer Diseases 0.000 description 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 2
- 208000017169 kidney disease Diseases 0.000 description 2
- 201000001441 melanoma Diseases 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 210000002346 musculoskeletal system Anatomy 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229960001592 paclitaxel Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 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 2
- 208000001608 teratocarcinoma Diseases 0.000 description 2
- 210000001685 thyroid gland Anatomy 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-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
- 208000024827 Alzheimer disease Diseases 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
- 208000003950 B-cell lymphoma Diseases 0.000 description 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- 101100242814 Caenorhabditis elegans parg-1 gene Proteins 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 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
- 241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 206010023347 Keratoacanthoma Diseases 0.000 description 1
- 102000029749 Microtubule Human genes 0.000 description 1
- 108091022875 Microtubule Proteins 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
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 208000007014 Retinitis pigmentosa Diseases 0.000 description 1
- 241000710960 Sindbis virus Species 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 206010042971 T-cell lymphoma Diseases 0.000 description 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 201000006083 Xeroderma Pigmentosum Diseases 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 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
- 230000003527 anti-angiogenesis Effects 0.000 description 1
- 230000005775 apoptotic pathway Effects 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 208000025434 cerebellar degeneration Diseases 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000003325 follicular Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 208000014951 hematologic disease Diseases 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 208000037906 ischaemic injury Diseases 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 208000017445 musculoskeletal system disease Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 208000007538 neurilemmoma Diseases 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 208000002320 spinal muscular atrophy Diseases 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- GMRIOAVKKGNMMV-UHFFFAOYSA-N tetrabutylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC GMRIOAVKKGNMMV-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 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
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22559000P | 2000-08-16 | 2000-08-16 | |
| PCT/US2001/024540 WO2002014323A2 (en) | 2000-08-16 | 2001-08-01 | Polymorphs of an epothilone analog |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20030707D0 NO20030707D0 (no) | 2003-02-14 |
| NO20030707L NO20030707L (no) | 2003-04-15 |
| NO328500B1 true NO328500B1 (no) | 2010-03-01 |
Family
ID=22845469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20030707A NO328500B1 (no) | 2000-08-16 | 2003-02-14 | Polymorfer av en epothilon-analog |
Country Status (42)
| Country | Link |
|---|---|
| US (4) | US6689802B2 (is) |
| EP (1) | EP1309597B1 (is) |
| JP (1) | JP5046467B2 (is) |
| KR (1) | KR100810342B1 (is) |
| CN (1) | CN1269821C (is) |
| AR (1) | AR034259A1 (is) |
| AT (1) | ATE366735T1 (is) |
| AU (2) | AU2001281082B2 (is) |
| BG (1) | BG66132B1 (is) |
| BR (1) | BR0113234A (is) |
| CA (1) | CA2418109C (is) |
| CY (1) | CY1107758T1 (is) |
| CZ (1) | CZ305523B6 (is) |
| DE (1) | DE60129334T2 (is) |
| DK (1) | DK1309597T3 (is) |
| EE (1) | EE05273B1 (is) |
| ES (1) | ES2288518T3 (is) |
| GE (1) | GEP20053495B (is) |
| HK (1) | HK1052010A1 (is) |
| HR (1) | HRP20030190B1 (is) |
| HU (1) | HU229314B1 (is) |
| IL (2) | IL153993A0 (is) |
| IS (1) | IS2845B (is) |
| LT (1) | LT5138B (is) |
| LV (1) | LV13032B (is) |
| MX (1) | MXPA03001431A (is) |
| MY (1) | MY134129A (is) |
| NO (1) | NO328500B1 (is) |
| NZ (1) | NZ523722A (is) |
| PE (1) | PE20020290A1 (is) |
| PL (1) | PL205628B1 (is) |
| PT (1) | PT1309597E (is) |
| RO (1) | RO123296B1 (is) |
| RU (1) | RU2272039C2 (is) |
| SI (1) | SI21100B (is) |
| SK (1) | SK287876B6 (is) |
| TW (1) | TWI320040B (is) |
| UA (1) | UA75365C2 (is) |
| UY (1) | UY26886A1 (is) |
| WO (1) | WO2002014323A2 (is) |
| YU (1) | YU12103A (is) |
| ZA (1) | ZA200300522B (is) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050043376A1 (en) * | 1996-12-03 | 2005-02-24 | Danishefsky Samuel J. | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
| DE69734362T2 (de) | 1996-12-03 | 2006-07-20 | Sloan-Kettering Institute For Cancer Research | Synthese von epothilonen, zwischenprodukte dazu, analoga und verwendungen davon |
| US6605599B1 (en) | 1997-07-08 | 2003-08-12 | Bristol-Myers Squibb Company | Epothilone derivatives |
| US6194181B1 (en) * | 1998-02-19 | 2001-02-27 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| US20020058286A1 (en) * | 1999-02-24 | 2002-05-16 | Danishefsky Samuel J. | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US6518421B1 (en) * | 2000-03-20 | 2003-02-11 | Bristol-Myers Squibb Company | Process for the preparation of epothilone analogs |
| MXPA03006412A (es) * | 2001-01-25 | 2003-10-15 | Bristol Myers Squibb Co | Metodos para administrar analogos de epotilona para tratamiento de cancer. |
| SK8552003A3 (en) * | 2001-01-25 | 2004-06-08 | Bristol Myers Squibb Co | Parenteral formulation containing epothilone analogs |
| HUP0303175A2 (hu) | 2001-02-20 | 2003-12-29 | Bristol-Myers Squibb Co. | Epotilonszármazékok alkalmazása makacs tumorok kezelésére alkalmas gyógyszerkészítmény előállítására |
| CA2440555A1 (en) * | 2001-03-14 | 2002-09-19 | Bristol-Myers Squibb Company | Combination of epothilone analogs and chemotherapeutic agents for the treatment of proliferative diseases |
| MXPA04008707A (es) * | 2002-03-08 | 2006-03-08 | Novartis Ag | Combinaciones que comprenden derivados de epotilona y agentes de alquilacion. |
| ES2281692T3 (es) * | 2002-08-23 | 2007-10-01 | Sloan-Kettering Institute For Cancer Research | Sintesis de epotilones, sus intermediarios, sus analogos y sus usos. |
| US7649006B2 (en) | 2002-08-23 | 2010-01-19 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US6921769B2 (en) | 2002-08-23 | 2005-07-26 | 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 |
| ITMI20032144A1 (it) * | 2003-11-07 | 2005-05-08 | Alfa Wassermann Spa | Forme polimorfe di rifaximina, processi per ottenerle e |
| US20090004277A1 (en) * | 2004-05-18 | 2009-01-01 | Franchini Miriam K | Nanoparticle dispersion containing lactam compound |
| EP1640004A1 (en) * | 2004-09-24 | 2006-03-29 | Schering Aktiengesellschaft | Use of epothilones in the treatment of bone metastases and bone tumors or cancers |
| KR20070084325A (ko) * | 2004-11-18 | 2007-08-24 | 브리스톨-마이어스 스큅 컴퍼니 | 익사베필론을 포함하는 장용성 코팅된 비드 및 그의 제조방법 |
| EP1824458A1 (en) * | 2004-11-18 | 2007-08-29 | Bristol-Myers Squibb Company | Enteric coated bead comprising epothilone or an epothilone analog, and preparation and administration thereof |
| US20060121511A1 (en) | 2004-11-30 | 2006-06-08 | Hyerim Lee | Biomarkers and methods for determining sensitivity to microtubule-stabilizing agents |
| 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 |
| SI1698630T1 (sl) * | 2005-03-03 | 2015-01-30 | Alfa Wassermann S.P.A. | Nove polimorfne oblike rifaksimina, postopki za njihovo pripravo in njihova uporaba v medicinskih pripravkih |
| EP1883627B1 (en) | 2005-05-18 | 2018-04-18 | Pharmascience Inc. | Bir domain binding compounds |
| US7693596B2 (en) | 2005-12-14 | 2010-04-06 | Dell Products L.P. | System and method for configuring information handling system integrated circuits |
| US20080286325A1 (en) * | 2006-01-05 | 2008-11-20 | Med Institute, Inc. | Cyclodextrin elution media for medical device coatings comprising a taxane therapeutic agent |
| US7919108B2 (en) * | 2006-03-10 | 2011-04-05 | Cook Incorporated | Taxane coatings for implantable medical devices |
| US7875284B2 (en) * | 2006-03-10 | 2011-01-25 | Cook Incorporated | Methods of manufacturing and modifying taxane coatings for implantable medical devices |
| EP1994412A2 (en) | 2006-03-31 | 2008-11-26 | Brystol-Myers Squibb Company | Biomarkers and methods for determining sensitivity to microtubule-stabilizing agents |
| US8008256B2 (en) | 2006-05-01 | 2011-08-30 | University Of Southern California | Combination therapy for treatment of cancer |
| NZ572836A (en) | 2006-05-16 | 2011-12-22 | Pharmascience Inc | Iap bir domain binding compounds |
| KR20090038902A (ko) * | 2006-08-16 | 2009-04-21 | 노파르티스 아게 | 에포틸론 ｂ의 결정 형태 및 제약 조성물에서의 용도 |
| US8463852B2 (en) * | 2006-10-06 | 2013-06-11 | Oracle International Corporation | Groupware portlets for integrating a portal with groupware systems |
| US20110124690A1 (en) * | 2007-02-23 | 2011-05-26 | Danishefsky Samuel J | Compositions and methods for treating cancer or a neurotrophic disorder |
| EP2065054A1 (en) | 2007-11-29 | 2009-06-03 | Bayer Schering Pharma Aktiengesellschaft | Combinations comprising a prostaglandin and uses thereof |
| DE102007059752A1 (de) | 2007-12-10 | 2009-06-18 | Bayer Schering Pharma Aktiengesellschaft | Funktionalisierte, feste Polymernanopartikel enthaltend Epothilone |
| EP2070521A1 (en) | 2007-12-10 | 2009-06-17 | Bayer Schering Pharma Aktiengesellschaft | Surface-modified nanoparticles |
| US8802394B2 (en) | 2008-11-13 | 2014-08-12 | Radu O. Minea | Method of expressing proteins with disulfide bridges with enhanced yields and activity |
| EP2210584A1 (en) | 2009-01-27 | 2010-07-28 | Bayer Schering Pharma Aktiengesellschaft | Stable polymeric composition comprising an epothilone and an amphiphilic block copolymer |
| SG10201501095WA (en) | 2010-02-12 | 2015-04-29 | Pharmascience Inc | Iap bir domain binding compounds |
| IT1398550B1 (it) | 2010-03-05 | 2013-03-01 | Alfa Wassermann Spa | Formulazioni comprendenti rifaximina utili per ottenere un effetto prolungato nel tempo |
| WO2011153221A1 (en) * | 2010-06-01 | 2011-12-08 | Plus Chemicals Sa | Solid state forms of ixabepilone |
| EP2793949B1 (en) | 2011-12-23 | 2018-08-22 | Innate Pharma | Enzymatic conjugation of antibodies |
| ITBO20120368A1 (it) | 2012-07-06 | 2014-01-07 | Alfa Wassermann Spa | Composizioni comprendenti rifaximina e amminoacidi, cristalli di rifaximina derivanti da tali composizioni e loro uso. |
| EP2872894B1 (en) | 2012-07-13 | 2019-04-17 | Innate Pharma | Screening of conjugated antibodies |
| EP2916872B1 (en) | 2012-11-09 | 2019-02-27 | Innate Pharma | Recognition tags for tgase-mediated conjugation |
| CN103183681B (zh) * | 2013-03-06 | 2016-01-13 | 浙江海正药业股份有限公司 | 伊沙匹隆的新晶型及其制备方法 |
| EP2968582B1 (en) | 2013-03-15 | 2020-07-01 | Innate Pharma | Solid phase tgase-mediated conjugation of antibodies |
| EP3010547B1 (en) | 2013-06-20 | 2021-04-21 | Innate Pharma | Enzymatic conjugation of polypeptides |
| CN105517577A (zh) | 2013-06-21 | 2016-04-20 | 先天制药公司 | 多肽的酶促偶联 |
| WO2019092148A1 (en) | 2017-11-10 | 2019-05-16 | Innate Pharma | Antibodies with functionalized glutamine residues |
| EP4097245A1 (en) | 2020-01-31 | 2022-12-07 | Allarity Therapeutics Europe ApS | Methods for predicting ixabepilone responsiveness in cancer patients |
| CN112409366A (zh) * | 2020-11-30 | 2021-02-26 | 湖北宏中药业股份有限公司 | 一种伊沙匹隆二聚体的高收率制备方法 |
| CN112457320A (zh) * | 2020-11-30 | 2021-03-09 | 湖北宏中药业股份有限公司 | 一种提高伊沙匹隆合成反应速率的方法 |
| CN112375085A (zh) * | 2020-11-30 | 2021-02-19 | 湖北宏中药业股份有限公司 | 一种伊沙匹隆反应液的高收率高纯度处理方法 |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1000809A (en) * | 1960-11-02 | 1965-08-11 | James Oakes & Company Riddings | Pipe manufacture |
| DE2308418B2 (de) * | 1972-06-21 | 1976-04-08 | Petzetakis, Aristovoulos George, Moschaton, Piräus (Griechenland) | Verfahren und vorrichtung zum herstellen eines insbesondere grosskalibrigen rohres aus thermoplastischem kunststoff |
| JPS5240337B2 (is) * | 1973-01-29 | 1977-10-12 | ||
| SE386365B (sv) * | 1973-07-25 | 1976-08-09 | L Brendling | Behallare av plast, gummi eller annat bojligt material, spec. avsedd for uppsamling av urin och/eller fekalier |
| JPS6398413A (ja) * | 1986-10-15 | 1988-04-28 | Smc Corp | 二重管およびその連続製造法 |
| DE3927569A1 (de) * | 1989-08-21 | 1991-02-28 | Fritz Egger Gmbh | Elektroabscheider zum abscheiden von schwebstoffen aus gasen |
| DE3939714A1 (de) * | 1989-12-01 | 1991-06-06 | Baedje K H Meteor Gummiwerke | Schlauch |
| AU6431790A (en) * | 1990-01-05 | 1991-08-05 | Orscheln Co. | Flexible synthetic plastic conduit |
| DE4138042C2 (de) | 1991-11-19 | 1993-10-14 | Biotechnolog Forschung Gmbh | Epothilone, deren Herstellungsverfahren sowie diese Verbindungen enthaltende Mittel |
| DE4206096A1 (de) * | 1992-02-27 | 1993-09-02 | Wolf Woco & Co Franz J | Koaxialrohr |
| 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 |
| DE19645361A1 (de) | 1996-08-30 | 1998-04-30 | Ciba Geigy Ag | Zwischenprodukte innerhalb der Totalsynthese von Epothilon A und B, Teil II |
| DE19636343C1 (de) | 1996-08-30 | 1997-10-23 | Schering Ag | Zwischenprodukte innerhalb der Totalsynthese von Epothilon A und B |
| JP2001500851A (ja) | 1996-08-30 | 2001-01-23 | ノバルティス アクチエンゲゼルシャフト | エポシロンの製造法および製造過程中に得られる中間生産物 |
| DE19645362A1 (de) | 1996-10-28 | 1998-04-30 | Ciba Geigy Ag | Verfahren zur Herstellung von Epothilon A und B und Derivaten |
| HU229833B1 (en) | 1996-11-18 | 2014-09-29 | Biotechnolog Forschung Gmbh | Epothilone d production process, and its use as cytostatic as well as phytosanitary agents |
| US6515016B2 (en) | 1996-12-02 | 2003-02-04 | Angiotech Pharmaceuticals, Inc. | Composition and methods of paclitaxel for treating psoriasis |
| DE69734362T2 (de) | 1996-12-03 | 2006-07-20 | Sloan-Kettering Institute For Cancer Research | Synthese von epothilonen, zwischenprodukte dazu, analoga und verwendungen davon |
| 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 |
| DE19701758A1 (de) | 1997-01-20 | 1998-07-23 | Wessjohann Ludgar A Dr | Epothilone-Synthesebausteine |
| CA2281105A1 (en) | 1997-02-25 | 1998-09-03 | Gesellschaft Fur Biotechnologische Forschung Mbh (Gbf) | Epothilones with a modified side chain |
| DE19713970B4 (de) | 1997-04-04 | 2006-08-31 | R&D-Biopharmaceuticals Gmbh | Epothilone-Synthesebausteine II - Prenylderivate |
| US6348551B1 (en) | 1997-04-18 | 2002-02-19 | Studiengesellschaft Kohle Mbh | Selective olefin metathesis of bifunctional or polyfunctional substrates in compressed carbon dioxide as reaction medium |
| 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 |
| JP2001510189A (ja) | 1997-07-16 | 2001-07-31 | シエーリング アクチエンゲゼルシヤフト | チアゾール誘導体、その製造法および使用 |
| DE59814067D1 (de) | 1997-08-09 | 2007-09-06 | Bayer Schering Pharma Ag | Neue epothilon-derivate, verfahren zu deren herstellung und ihre pharmazeutische verwendung |
| DE19747580A1 (de) | 1997-10-28 | 1999-04-29 | Siemens Ag | Rangierfeld mit Anschlußleiste |
| 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 |
| BR9907647B1 (pt) | 1998-02-05 | 2014-04-01 | Novartis Ag Novartis S A Novartis Inc | Formulação farmacêutica na forma de um concentrado para infusão, o qual deve ser diluído antes da administração, e solução para infusão |
| US6194181B1 (en) | 1998-02-19 | 2001-02-27 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| DE19807505A1 (de) | 1998-02-21 | 1999-08-26 | Roland Man Druckmasch | Bogenrotationsdruckmaschine mit Druckeinheiten für den Mehrfarbendruck und wenigstens einer Beschichtungseinheit |
| 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 |
| NZ506742A (en) | 1998-02-25 | 2003-09-26 | Sloan Kettering Inst Cancer | Synthesis of desoxyepothilones and hydroxy acid derivative intermediates |
| WO2000000485A1 (de) | 1998-06-30 | 2000-01-06 | Schering Aktiengesellschaft | Epothilon-derivate, verfahren zu deren herstellung, zwischenprodukte und ihre pharmazeutische verwendung |
| AU5325699A (en) * | 1998-08-12 | 2000-03-06 | Proteus Inc. | Ribbed core dual wall structure |
| AU2795000A (en) | 1998-12-22 | 2000-07-12 | Novartis Ag | Epothilone derivatives and their use as antitumor agents |
| PE20010116A1 (es) | 1999-04-30 | 2001-02-15 | Schering Ag | Derivados de 6-alquenil-, 6-alquinil- y 6-epoxi-epotilona, procedimientos para su preparacion |
| US6605559B1 (en) * | 1999-09-29 | 2003-08-12 | Daihatsu Motor Co., Ltd. | Dimethyl ether reforming catalyst |
| US6518421B1 (en) | 2000-03-20 | 2003-02-11 | Bristol-Myers Squibb Company | Process for the preparation of epothilone analogs |
| SK8552003A3 (en) * | 2001-01-25 | 2004-06-08 | Bristol Myers Squibb Co | Parenteral formulation containing epothilone analogs |
| NZ526870A (en) | 2001-01-25 | 2005-11-25 | Bristol Myers Squibb Co | Methods of administering epothilone analogs for the treatment of cancer |
| US9317043B2 (en) | 2013-12-19 | 2016-04-19 | Google Inc. | Path based power generation control for an aerial vehicle |
-
2001
- 2001-01-08 UA UA2003032259A patent/UA75365C2/uk unknown
- 2001-07-26 MY MYPI20013545 patent/MY134129A/en unknown
- 2001-08-01 BR BR0113234-2A patent/BR0113234A/pt active Search and Examination
- 2001-08-01 WO PCT/US2001/024540 patent/WO2002014323A2/en active IP Right Grant
- 2001-08-01 CZ CZ2003-418A patent/CZ305523B6/cs not_active IP Right Cessation
- 2001-08-01 AU AU2001281082A patent/AU2001281082B2/en not_active Ceased
- 2001-08-01 RO ROA200300114A patent/RO123296B1/ro unknown
- 2001-08-01 SI SI200120055A patent/SI21100B/sl not_active IP Right Cessation
- 2001-08-01 GE GE5091A patent/GEP20053495B/en unknown
- 2001-08-01 YU YU12103A patent/YU12103A/sh unknown
- 2001-08-01 JP JP2002519462A patent/JP5046467B2/ja not_active Expired - Fee Related
- 2001-08-01 KR KR1020037002256A patent/KR100810342B1/ko not_active IP Right Cessation
- 2001-08-01 DK DK01959536T patent/DK1309597T3/da active
- 2001-08-01 ES ES01959536T patent/ES2288518T3/es not_active Expired - Lifetime
- 2001-08-01 AT AT01959536T patent/ATE366735T1/de active
- 2001-08-01 RU RU2003106431/04A patent/RU2272039C2/ru active
- 2001-08-01 MX MXPA03001431A patent/MXPA03001431A/es active IP Right Grant
- 2001-08-01 EE EEP200300063A patent/EE05273B1/xx not_active IP Right Cessation
- 2001-08-01 AU AU8108201A patent/AU8108201A/xx active Pending
- 2001-08-01 EP EP01959536A patent/EP1309597B1/en not_active Expired - Lifetime
- 2001-08-01 SK SK134-2003A patent/SK287876B6/sk not_active IP Right Cessation
- 2001-08-01 DE DE60129334T patent/DE60129334T2/de not_active Expired - Lifetime
- 2001-08-01 IL IL15399301A patent/IL153993A0/xx unknown
- 2001-08-01 CA CA2418109A patent/CA2418109C/en not_active Expired - Lifetime
- 2001-08-01 PT PT01959536T patent/PT1309597E/pt unknown
- 2001-08-01 NZ NZ523722A patent/NZ523722A/en not_active IP Right Cessation
- 2001-08-01 PL PL365610A patent/PL205628B1/pl unknown
- 2001-08-01 CN CNB018170641A patent/CN1269821C/zh not_active Expired - Lifetime
- 2001-08-01 HU HU0300826A patent/HU229314B1/hu not_active IP Right Cessation
- 2001-08-09 US US09/925,112 patent/US6689802B2/en not_active Ceased
- 2001-08-10 TW TW090119585A patent/TWI320040B/zh not_active IP Right Cessation
- 2001-08-15 AR ARP010103901A patent/AR034259A1/es not_active Application Discontinuation
- 2001-08-15 UY UY26886A patent/UY26886A1/es not_active Application Discontinuation
- 2001-08-16 PE PE2001000818A patent/PE20020290A1/es not_active Application Discontinuation
-
2003
- 2003-01-16 IL IL153993A patent/IL153993A/en not_active IP Right Cessation
- 2003-01-16 BG BG107467A patent/BG66132B1/bg unknown
- 2003-01-20 ZA ZA200300522A patent/ZA200300522B/en unknown
- 2003-02-11 IS IS6714A patent/IS2845B/is unknown
- 2003-02-14 NO NO20030707A patent/NO328500B1/no not_active IP Right Cessation
- 2003-02-25 LT LT2003017A patent/LT5138B/lt not_active IP Right Cessation
- 2003-03-07 LV LVP-03-28A patent/LV13032B/en unknown
- 2003-03-14 HR HR20030190A patent/HRP20030190B1/xx not_active IP Right Cessation
- 2003-06-17 HK HK03104338A patent/HK1052010A1/xx not_active IP Right Cessation
-
2004
- 2004-02-06 US US10/773,819 patent/US6982276B2/en not_active Expired - Lifetime
-
2005
- 2005-03-09 US US11/076,589 patent/USRE39251E1/en not_active Expired - Lifetime
- 2005-11-10 US US11/271,456 patent/US7153879B2/en not_active Expired - Lifetime
-
2007
- 2007-10-11 CY CY20071101304T patent/CY1107758T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO328500B1 (no) | Polymorfer av en epothilon-analog | |
| AU2001281082A1 (en) | Polymorphs of an epothilone analog | |
| EP3557998B1 (en) | Compouns, compositions and methods of use | |
| CA2737055C (en) | Crystalline forms of a 2-thiazolyl- 4-quinolinyl-oxy derivative, a potent hcv inhibitor | |
| DE69832294T2 (de) | Epothilonderivate | |
| DE60132309T2 (de) | Amin-derivate zur behandlung von apoptosis | |
| EP3917616A1 (en) | Heterocyclic compound and use thereof | |
| CN104114542B (zh) | 三唑并嘧啶化合物的合成 | |
| CN115443129A (zh) | Kcnt1抑制剂和使用方法 | |
| JP2020536898A (ja) | スピロ誘導体を調製するためのプロセス |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |