FI117690B - Kasvainten vastaisten metyylitritioyhdisteiden konjugaatteja ja välituotteita niiden synteesiä varten - Google Patents
Kasvainten vastaisten metyylitritioyhdisteiden konjugaatteja ja välituotteita niiden synteesiä varten Download PDFInfo
- Publication number
- FI117690B FI117690B FI952720A FI952720A FI117690B FI 117690 B FI117690 B FI 117690B FI 952720 A FI952720 A FI 952720A FI 952720 A FI952720 A FI 952720A FI 117690 B FI117690 B FI 117690B
- Authority
- FI
- Finland
- Prior art keywords
- bond
- alkyl
- nconhr
- coor
- alkoxy
- Prior art date
Links
- -1 Methyl Tritium Compounds Chemical class 0.000 title claims description 123
- 230000015572 biosynthetic process Effects 0.000 title abstract description 14
- 238000003786 synthesis reaction Methods 0.000 title abstract description 14
- 230000000259 anti-tumor effect Effects 0.000 title abstract description 11
- 239000000543 intermediate Substances 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 132
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 229940079593 drug Drugs 0.000 claims abstract description 34
- 239000003814 drug Substances 0.000 claims abstract description 34
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 23
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 19
- 150000003431 steroids Chemical class 0.000 claims abstract description 11
- 239000012634 fragment Substances 0.000 claims abstract description 10
- 239000003102 growth factor Substances 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 96
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- 239000000243 solution Substances 0.000 claims description 67
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000003047 N-acetyl group Chemical group 0.000 claims description 59
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 150000002367 halogens Chemical class 0.000 claims description 58
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 54
- 210000004027 cell Anatomy 0.000 claims description 52
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 44
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 150000002148 esters Chemical class 0.000 claims description 32
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 108091007433 antigens Proteins 0.000 claims description 23
- 239000000427 antigen Substances 0.000 claims description 21
- 102000036639 antigens Human genes 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 229940127089 cytotoxic agent Drugs 0.000 claims description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 15
- 239000002254 cytotoxic agent Substances 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 229950000688 phenothiazine Drugs 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 230000027455 binding Effects 0.000 claims description 11
- 238000009739 binding Methods 0.000 claims description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 150000001408 amides Chemical class 0.000 claims description 10
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 10
- 125000001475 halogen functional group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 7
- 239000004472 Lysine Substances 0.000 claims description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000000571 coke Substances 0.000 claims description 6
- 230000001472 cytotoxic effect Effects 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 230000012010 growth Effects 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 231100000433 cytotoxic Toxicity 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 5
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 229960002317 succinimide Drugs 0.000 claims description 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 102100032306 Aurora kinase B Human genes 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- 101000798306 Homo sapiens Aurora kinase B Proteins 0.000 claims description 3
- 108010029180 Sialic Acid Binding Ig-like Lectin 3 Proteins 0.000 claims description 3
- 102000001555 Sialic Acid Binding Ig-like Lectin 3 Human genes 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000003966 growth inhibitor Substances 0.000 claims description 3
- 208000032839 leukemia Diseases 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 102000003886 Glycoproteins Human genes 0.000 claims description 2
- 108090000288 Glycoproteins Proteins 0.000 claims description 2
- 102000010789 Interleukin-2 Receptors Human genes 0.000 claims description 2
- 108010038453 Interleukin-2 Receptors Proteins 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 239000008363 phosphate buffer Substances 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 230000001502 supplementing effect Effects 0.000 claims 6
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
- 230000010261 cell growth Effects 0.000 claims 3
- 239000013589 supplement Substances 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims 2
- 101150072531 10 gene Proteins 0.000 claims 1
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 claims 1
- PBYIIRLNRCVTMQ-UHFFFAOYSA-N 2,3,5,6-tetrafluorophenol Chemical compound OC1=C(F)C(F)=CC(F)=C1F PBYIIRLNRCVTMQ-UHFFFAOYSA-N 0.000 claims 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 claims 1
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical compound ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 claims 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 102000015728 Mucins Human genes 0.000 claims 1
- 108010063954 Mucins Proteins 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 239000012062 aqueous buffer Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 239000008366 buffered solution Substances 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 238000004108 freeze drying Methods 0.000 claims 1
- 230000002068 genetic effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- DFIWJEVKLWMZBI-UHFFFAOYSA-M sodium;dihydrogen phosphate;phosphoric acid Chemical compound [Na+].OP(O)(O)=O.OP(O)([O-])=O DFIWJEVKLWMZBI-UHFFFAOYSA-M 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 14
- 229930195731 calicheamicin Natural products 0.000 abstract description 13
- 230000008685 targeting Effects 0.000 abstract description 9
- 239000003242 anti bacterial agent Substances 0.000 abstract description 7
- 229940088710 antibiotic agent Drugs 0.000 abstract description 7
- 239000000969 carrier Substances 0.000 abstract description 6
- 230000003389 potentiating effect Effects 0.000 abstract description 4
- HXCHCVDVKSCDHU-LULTVBGHSA-N calicheamicin Chemical compound C1[C@H](OC)[C@@H](NCC)CO[C@H]1O[C@H]1[C@H](O[C@@H]2C\3=C(NC(=O)OC)C(=O)C[C@](C/3=C/CSSSC)(O)C#C\C=C/C#C2)O[C@H](C)[C@@H](NO[C@@H]2O[C@H](C)[C@@H](SC(=O)C=3C(=C(OC)C(O[C@H]4[C@@H]([C@H](OC)[C@@H](O)[C@H](C)O4)O)=C(I)C=3C)OC)[C@@H](O)C2)[C@@H]1O HXCHCVDVKSCDHU-LULTVBGHSA-N 0.000 abstract description 3
- 150000002019 disulfides Chemical class 0.000 abstract description 3
- 229930189413 Esperamicin Natural products 0.000 abstract 1
- 239000000047 product Substances 0.000 description 88
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
- 238000004128 high performance liquid chromatography Methods 0.000 description 68
- 230000014759 maintenance of location Effects 0.000 description 66
- 238000002360 preparation method Methods 0.000 description 61
- 238000000338 in vitro Methods 0.000 description 60
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- 238000005481 NMR spectroscopy Methods 0.000 description 45
- 238000004458 analytical method Methods 0.000 description 34
- 239000000203 mixture Substances 0.000 description 32
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 30
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 28
- 229910000027 potassium carbonate Inorganic materials 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- FNHIEZKOCYDCOH-UHFFFAOYSA-N 4-(4-acetylphenoxy)butanoic acid Chemical compound CC(=O)C1=CC=C(OCCCC(O)=O)C=C1 FNHIEZKOCYDCOH-UHFFFAOYSA-N 0.000 description 24
- 230000005764 inhibitory process Effects 0.000 description 24
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 239000013078 crystal Substances 0.000 description 20
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 20
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 230000008018 melting Effects 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- QMJMMMFRTIBWEO-UHFFFAOYSA-N 3-[4-(2-oxoethoxy)phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=C(OCC=O)C=C1 QMJMMMFRTIBWEO-UHFFFAOYSA-N 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- VIBMSNLNURQOFL-UHFFFAOYSA-N ethyl 4-(4-acetylphenoxy)butanoate Chemical compound CCOC(=O)CCCOC1=CC=C(C(C)=O)C=C1 VIBMSNLNURQOFL-UHFFFAOYSA-N 0.000 description 14
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 14
- 125000005647 linker group Chemical group 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- ORVNCMYBCMQQSV-UHFFFAOYSA-N 2-(4-formyl-3-methoxyphenoxy)acetic acid Chemical compound COC1=CC(OCC(O)=O)=CC=C1C=O ORVNCMYBCMQQSV-UHFFFAOYSA-N 0.000 description 13
- XDFURLIDHXAXOX-UHFFFAOYSA-N 4-(4-acetyl-2-methylphenoxy)butanoic acid Chemical compound CC(=O)C1=CC=C(OCCCC(O)=O)C(C)=C1 XDFURLIDHXAXOX-UHFFFAOYSA-N 0.000 description 13
- SHFLOIUZUDNHFB-UHFFFAOYSA-N 6-formylnaphthalene-2-carboxylic acid Chemical compound C1=C(C=O)C=CC2=CC(C(=O)O)=CC=C21 SHFLOIUZUDNHFB-UHFFFAOYSA-N 0.000 description 12
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 12
- NRCCSDVEUWXOMG-UHFFFAOYSA-N 3-(4-formylphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(C=O)C=C1 NRCCSDVEUWXOMG-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
- 150000007857 hydrazones Chemical class 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 238000001727 in vivo Methods 0.000 description 10
- XVJCDBNIJPRALE-UHFFFAOYSA-N 3-(2-oxoethoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC(OCC=O)=C1 XVJCDBNIJPRALE-UHFFFAOYSA-N 0.000 description 9
- FAHSGPRRDXUKNV-UHFFFAOYSA-N 4-(2-acetylnaphthalen-1-yl)oxybutanoic acid Chemical compound C1=CC=CC2=C(OCCCC(O)=O)C(C(=O)C)=CC=C21 FAHSGPRRDXUKNV-UHFFFAOYSA-N 0.000 description 9
- ZAQGUGMNKZJMRN-UHFFFAOYSA-N 4-(2-chloro-4-formylphenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(C=O)C=C1Cl ZAQGUGMNKZJMRN-UHFFFAOYSA-N 0.000 description 9
- QHLKXVXBJDXSHQ-UHFFFAOYSA-N 4-(3-formylphenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=CC(C=O)=C1 QHLKXVXBJDXSHQ-UHFFFAOYSA-N 0.000 description 9
- AJSDTGPNCVIIFP-UHFFFAOYSA-N 4-(4-acetyl-2-methoxyphenoxy)butanoic acid Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCC(O)=O AJSDTGPNCVIIFP-UHFFFAOYSA-N 0.000 description 9
- WWIBPDXHHHXRCU-UHFFFAOYSA-N 4-(4-formyl-2-nitrophenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(C=O)C=C1[N+]([O-])=O WWIBPDXHHHXRCU-UHFFFAOYSA-N 0.000 description 9
- UQCWMYYXDKTJBT-UHFFFAOYSA-N 4-[4-(4-fluorobenzoyl)phenoxy]butanoic acid Chemical compound C1=CC(OCCCC(=O)O)=CC=C1C(=O)C1=CC=C(F)C=C1 UQCWMYYXDKTJBT-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 235000018102 proteins Nutrition 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- XCJOFTQRNQNUPS-UHFFFAOYSA-N 4-(2-acetyl-5-methoxyphenoxy)butanoic acid Chemical compound COC1=CC=C(C(C)=O)C(OCCCC(O)=O)=C1 XCJOFTQRNQNUPS-UHFFFAOYSA-N 0.000 description 8
- WKFFJPNYTCCXSM-UHFFFAOYSA-N 4-(4-formyl-2-methoxyphenoxy)butanoic acid Chemical compound COC1=CC(C=O)=CC=C1OCCCC(O)=O WKFFJPNYTCCXSM-UHFFFAOYSA-N 0.000 description 8
- GKECISRCTNHSNA-UHFFFAOYSA-N 4-(4-formylphenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(C=O)C=C1 GKECISRCTNHSNA-UHFFFAOYSA-N 0.000 description 8
- NGFMLSYWOOYFPR-UHFFFAOYSA-N 4-(5-formyl-2,3-dimethoxyphenoxy)butanoic acid Chemical compound COC1=CC(C=O)=CC(OCCCC(O)=O)=C1OC NGFMLSYWOOYFPR-UHFFFAOYSA-N 0.000 description 8
- QPLJEVMTRJAKKF-UHFFFAOYSA-N 4-[4-(3-oxopropyl)phenoxy]butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(CCC=O)C=C1 QPLJEVMTRJAKKF-UHFFFAOYSA-N 0.000 description 8
- YLUUREXLUWBLKT-UHFFFAOYSA-N 5-[4-(4-acetylphenyl)piperazin-1-yl]pentanoic acid Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(CCCCC(O)=O)CC1 YLUUREXLUWBLKT-UHFFFAOYSA-N 0.000 description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 150000001720 carbohydrates Chemical group 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000013612 plasmid Substances 0.000 description 8
- 235000009518 sodium iodide Nutrition 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- OYNIIKHNXNPSAG-UHFFFAOYSA-N 2-(4-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C=O)C=C1 OYNIIKHNXNPSAG-UHFFFAOYSA-N 0.000 description 7
- WCSGOUGRUOAKAE-UHFFFAOYSA-N 4-(4-acetyl-3-fluorophenoxy)butanoic acid Chemical compound CC(=O)C1=CC=C(OCCCC(O)=O)C=C1F WCSGOUGRUOAKAE-UHFFFAOYSA-N 0.000 description 7
- XPJPCHDGIXILNO-UHFFFAOYSA-N 6-(2-acetylphenothiazin-10-yl)hexanoic acid Chemical compound C1=CC=C2N(CCCCCC(O)=O)C3=CC(C(=O)C)=CC=C3SC2=C1 XPJPCHDGIXILNO-UHFFFAOYSA-N 0.000 description 7
- YWHLKYXPLRWGSE-UHFFFAOYSA-N Dimethyl trisulfide Chemical compound CSSSC YWHLKYXPLRWGSE-UHFFFAOYSA-N 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 235000018977 lysine Nutrition 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 7
- JJSYBHLDYYGVPN-UHFFFAOYSA-N 4-(4-acetyl-2-methoxycarbonylphenoxy)butanoic acid Chemical compound COC(=O)C1=CC(C(C)=O)=CC=C1OCCCC(O)=O JJSYBHLDYYGVPN-UHFFFAOYSA-N 0.000 description 6
- KYKPEIJBVFIUPI-UHFFFAOYSA-N 4-[4-(3-oxobutyl)phenoxy]butanoic acid Chemical compound CC(=O)CCC1=CC=C(OCCCC(O)=O)C=C1 KYKPEIJBVFIUPI-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 235000014633 carbohydrates Nutrition 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000021615 conjugation Effects 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 6
- OXZDQGRQLAXRRU-UHFFFAOYSA-N 11-(4-acetylphenoxy)undecanoic acid Chemical compound CC(=O)C1=CC=C(OCCCCCCCCCCC(O)=O)C=C1 OXZDQGRQLAXRRU-UHFFFAOYSA-N 0.000 description 5
- DQGDHZGCMKDNRW-UHFFFAOYSA-N 2-(4-acetylphenyl)acetic acid Chemical compound CC(=O)C1=CC=C(CC(O)=O)C=C1 DQGDHZGCMKDNRW-UHFFFAOYSA-N 0.000 description 5
- GKQDMBJOJUXRKT-UHFFFAOYSA-N 4-(2-acetylphenoxy)butanoic acid Chemical compound CC(=O)C1=CC=CC=C1OCCCC(O)=O GKQDMBJOJUXRKT-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- ZMEBKXNYMWXFEX-UHFFFAOYSA-N 3-prop-2-enoxybenzoic acid Chemical compound OC(=O)C1=CC=CC(OCC=C)=C1 ZMEBKXNYMWXFEX-UHFFFAOYSA-N 0.000 description 4
- WYBDRGCJOSNQRZ-UHFFFAOYSA-N 4-(4-acetyl-2,6-dimethoxyphenoxy)butanoic acid Chemical compound COC1=CC(C(C)=O)=CC(OC)=C1OCCCC(O)=O WYBDRGCJOSNQRZ-UHFFFAOYSA-N 0.000 description 4
- QMHJXTPQKASHRK-UHFFFAOYSA-N 4-[2-[(4-acetylanilino)methyl]-6-methoxyphenoxy]butanoic acid Chemical compound COC1=CC=CC(CNC=2C=CC(=CC=2)C(C)=O)=C1OCCCC(O)=O QMHJXTPQKASHRK-UHFFFAOYSA-N 0.000 description 4
- WMOTVRRRGWZNIA-UHFFFAOYSA-N 5-acetyl-2-(3-carboxypropoxy)benzoic acid Chemical compound CC(=O)C1=CC=C(OCCCC(O)=O)C(C(O)=O)=C1 WMOTVRRRGWZNIA-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 4
- 239000006184 cosolvent Substances 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 239000012038 nucleophile Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- COYYOMXYLXFEHS-UHFFFAOYSA-N 2-(2-acetylphenoxy)butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC=C1C(C)=O COYYOMXYLXFEHS-UHFFFAOYSA-N 0.000 description 3
- RUBFHRGMUPJXGP-UHFFFAOYSA-N 4-[4-(3-hydroxypropyl)phenoxy]butanoic acid Chemical compound OCCCC1=CC=C(OCCCC(O)=O)C=C1 RUBFHRGMUPJXGP-UHFFFAOYSA-N 0.000 description 3
- CDSCQUCBPNCYSM-UHFFFAOYSA-N 5-(4-acetylanilino)-5-oxopentanoic acid Chemical compound CC(=O)C1=CC=C(NC(=O)CCCC(O)=O)C=C1 CDSCQUCBPNCYSM-UHFFFAOYSA-N 0.000 description 3
- LPNANKDXVBMDKE-UHFFFAOYSA-N 5-bromopent-1-ene Chemical compound BrCCCC=C LPNANKDXVBMDKE-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012039 electrophile Substances 0.000 description 3
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 2
- NVLTWXMZECWWPC-UHFFFAOYSA-N 3-hydroxy-4,5-dimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(O)=C1OC NVLTWXMZECWWPC-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 108020004414 DNA Proteins 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- 241000400611 Eucalyptus deanei Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical class 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
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000012980 RPMI-1640 medium Substances 0.000 description 2
- 239000012506 Sephacryl® Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 241000863480 Vinca Species 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000000601 blood cell Anatomy 0.000 description 2
- 210000001185 bone marrow Anatomy 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- IYVFLUQQRRBHOV-UHFFFAOYSA-N ethyl 4-(2-acetylnaphthalen-1-yl)oxybutanoate Chemical compound C(C)OC(CCCOC1=C(C=CC2=CC=CC=C12)C(C)=O)=O IYVFLUQQRRBHOV-UHFFFAOYSA-N 0.000 description 2
- DQKZXCOPRAANIJ-UHFFFAOYSA-N ethyl 4-(3-formylphenoxy)butanoate Chemical compound CCOC(=O)CCCOC1=CC=CC(C=O)=C1 DQKZXCOPRAANIJ-UHFFFAOYSA-N 0.000 description 2
- BXVCUAVSVABDQS-UHFFFAOYSA-N ethyl 4-[4-(3-oxobutyl)phenoxy]butanoate Chemical compound CCOC(=O)CCCOC1=CC=C(CCC(C)=O)C=C1 BXVCUAVSVABDQS-UHFFFAOYSA-N 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- LBOUHDMYVURTMA-AATRIKPKSA-N (e)-3-(4-formylphenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(C=O)C=C1 LBOUHDMYVURTMA-AATRIKPKSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- PIRRWUMTIBFCCW-UHFFFAOYSA-N 1-(2-fluoro-4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(C)=O)C(F)=C1 PIRRWUMTIBFCCW-UHFFFAOYSA-N 0.000 description 1
- YYLCJWIQUFHYMY-UHFFFAOYSA-N 1-(4-butoxyphenyl)ethanone Chemical compound CCCCOC1=CC=C(C(C)=O)C=C1 YYLCJWIQUFHYMY-UHFFFAOYSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- PFMJODPCPZHPGB-UHFFFAOYSA-N 2-(3-formyl-5-methoxyphenoxy)acetic acid Chemical compound COc1cc(OCC(O)=O)cc(C=O)c1 PFMJODPCPZHPGB-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- DDDXIQDKNHOPJO-UHFFFAOYSA-N 2-pent-4-enoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCCC=C DDDXIQDKNHOPJO-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- QBJZQVXPGHFVAG-UHFFFAOYSA-N 3-(4-prop-2-enoxyphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(OCC=C)C=C1 QBJZQVXPGHFVAG-UHFFFAOYSA-N 0.000 description 1
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- VGSOCYWCRMXQAB-UHFFFAOYSA-N 3-chloro-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1Cl VGSOCYWCRMXQAB-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- WEKMUBUZJDWJIR-UHFFFAOYSA-N 4-(1-hydroxypropyl)phenol Chemical compound CCC(O)C1=CC=C(O)C=C1 WEKMUBUZJDWJIR-UHFFFAOYSA-N 0.000 description 1
- BLKZSCZBOQMBKO-UHFFFAOYSA-N 4-(4-acetylphenyl)butanoic acid Chemical compound CC(=O)C1=CC=C(CCCC(O)=O)C=C1 BLKZSCZBOQMBKO-UHFFFAOYSA-N 0.000 description 1
- IMLGJYRKLCMJPI-UHFFFAOYSA-N 4-(hydroxymethyl)-2-nitrophenol Chemical compound OCC1=CC=C(O)C([N+]([O-])=O)=C1 IMLGJYRKLCMJPI-UHFFFAOYSA-N 0.000 description 1
- MQSTYSBPYQKIHQ-UHFFFAOYSA-N 4-[4-(hydroxymethyl)-2-nitrophenoxy]butanoic acid Chemical compound OCC1=CC=C(OCCCC(O)=O)C([N+]([O-])=O)=C1 MQSTYSBPYQKIHQ-UHFFFAOYSA-N 0.000 description 1
- PRWSLLCPPUHCQG-UHFFFAOYSA-N 4-[4-acetyl-2-[2-(dimethylamino)ethylcarbamoyl]phenoxy]butanoic acid Chemical compound CN(C)CCNC(=O)C1=CC(C(C)=O)=CC=C1OCCCC(O)=O PRWSLLCPPUHCQG-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- XHWMNHADTZZHGI-UHFFFAOYSA-N 4-butoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C=C1 XHWMNHADTZZHGI-UHFFFAOYSA-N 0.000 description 1
- HLRVUOFDBXRZBI-UHFFFAOYSA-N 4-fluoro-4'-hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(F)C=C1 HLRVUOFDBXRZBI-UHFFFAOYSA-N 0.000 description 1
- LXBHHIZIQVZGFN-UHFFFAOYSA-N 4-hydroxy-3-methylacetophenone Chemical compound CC(=O)C1=CC=C(O)C(C)=C1 LXBHHIZIQVZGFN-UHFFFAOYSA-N 0.000 description 1
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 description 1
- CUARLQDWYSRQDF-UHFFFAOYSA-N 5-Nitroacenaphthene Chemical compound C1CC2=CC=CC3=C2C1=CC=C3[N+](=O)[O-] CUARLQDWYSRQDF-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- GJDAMLVEFRMIHZ-UHFFFAOYSA-N 5-acetyl-2-methoxybenzoic acid Chemical compound COC1=CC=C(C(C)=O)C=C1C(O)=O GJDAMLVEFRMIHZ-UHFFFAOYSA-N 0.000 description 1
- POBJSKMIBFQMSJ-UHFFFAOYSA-N 5-acetyl-2-pent-4-enoxybenzoic acid Chemical compound CC(=O)C1=CC=C(OCCCC=C)C(C(O)=O)=C1 POBJSKMIBFQMSJ-UHFFFAOYSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- PBKXRKYUUXKNSL-UHFFFAOYSA-N 6-bromohexoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCCCCCBr PBKXRKYUUXKNSL-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- 241000190711 Amapari mammarenavirus Species 0.000 description 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 208000011691 Burkitt lymphomas Diseases 0.000 description 1
- NJQWHFZBNUWKKP-UHFFFAOYSA-N C(C)(=O)OCC.BrCCCC(=O)O Chemical compound C(C)(=O)OCC.BrCCCC(=O)O NJQWHFZBNUWKKP-UHFFFAOYSA-N 0.000 description 1
- LETGBPQBGOKVSY-UHFFFAOYSA-N C1=CC=C2C(=C1)N(C3=CC=CC=C3S2)CCCCCC(=O)O Chemical compound C1=CC=C2C(=C1)N(C3=CC=CC=C3S2)CCCCCC(=O)O LETGBPQBGOKVSY-UHFFFAOYSA-N 0.000 description 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 1
- 108091026890 Coding region Proteins 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 description 1
- 101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 description 1
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 description 1
- 208000036566 Erythroleukaemia Diseases 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 description 1
- 241000943499 Gymnoglyphus osu Species 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
- ZAVVTMULLYNMOH-UHFFFAOYSA-N I.C(C1=CC=CC=C1)(=O)OC Chemical compound I.C(C1=CC=CC=C1)(=O)OC ZAVVTMULLYNMOH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- UILPJVPSNHJFIK-UHFFFAOYSA-N Paeonol Chemical compound COC1=CC=C(C(C)=O)C(O)=C1 UILPJVPSNHJFIK-UHFFFAOYSA-N 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- FRYDSOYOHWGSMD-UHFFFAOYSA-N [C].O Chemical compound [C].O FRYDSOYOHWGSMD-UHFFFAOYSA-N 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- OJOBTAOGJIWAGB-UHFFFAOYSA-N acetosyringone Chemical compound COC1=CC(C(C)=O)=CC(OC)=C1O OJOBTAOGJIWAGB-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 208000021841 acute erythroid leukemia Diseases 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000002798 bone marrow cell Anatomy 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- ZNTWHKMVUJAUKI-UHFFFAOYSA-N butanoic acid 1-phenylethanone Chemical compound CCCC(O)=O.CC(=O)C1=CC=CC=C1 ZNTWHKMVUJAUKI-UHFFFAOYSA-N 0.000 description 1
- XTEOJPUYZWEXFI-UHFFFAOYSA-N butyl n-[3-[4-(imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophen-2-yl]sulfonylcarbamate Chemical compound S1C(CC(C)C)=CC(C=2C=CC(CN3C=NC=C3)=CC=2)=C1S(=O)(=O)NC(=O)OCCCC XTEOJPUYZWEXFI-UHFFFAOYSA-N 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- JMFRWRFFLBVWSI-UHFFFAOYSA-N cis-coniferyl alcohol Natural products COC1=CC(C=CCO)=CC=C1O JMFRWRFFLBVWSI-UHFFFAOYSA-N 0.000 description 1
- 230000005757 colony formation Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 238000002784 cytotoxicity assay Methods 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003118 drug derivative Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- QPFNPHZHXXINRC-UHFFFAOYSA-N ethyl 2-(2-acetylphenoxy)butanoate Chemical compound CCOC(=O)C(CC)OC1=CC=CC=C1C(C)=O QPFNPHZHXXINRC-UHFFFAOYSA-N 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- NUBWWOUEFVZRFO-UHFFFAOYSA-N ethyl 4-(2-chloro-4-formylphenoxy)butanoate Chemical compound C(C)OC(CCCOC1=C(C=C(C=C1)C=O)Cl)=O NUBWWOUEFVZRFO-UHFFFAOYSA-N 0.000 description 1
- YPNQXNBSDGOISQ-UHFFFAOYSA-N ethyl 4-(4-acetyl-2,6-dimethoxyphenoxy)butanoate Chemical compound CCOC(=O)CCCOC1=C(OC)C=C(C(C)=O)C=C1OC YPNQXNBSDGOISQ-UHFFFAOYSA-N 0.000 description 1
- MKKVQFXWAOWFAQ-UHFFFAOYSA-N ethyl 4-(4-acetyl-2-methoxyphenoxy)butanoate Chemical compound CCOC(=O)CCCOC1=CC=C(C(C)=O)C=C1OC MKKVQFXWAOWFAQ-UHFFFAOYSA-N 0.000 description 1
- NTKSNOOBFLJMOE-UHFFFAOYSA-N ethyl 4-(4-formyl-2-nitrophenoxy)butanoate Chemical compound CCOC(=O)CCCOC1=CC=C(C=O)C=C1[N+]([O-])=O NTKSNOOBFLJMOE-UHFFFAOYSA-N 0.000 description 1
- ZJXCEHXWCWYIFA-UHFFFAOYSA-N ethyl 4-(5-formyl-2,3-dimethoxyphenoxy)butanoate Chemical compound CCOC(=O)CCCOC1=CC(C=O)=CC(OC)=C1OC ZJXCEHXWCWYIFA-UHFFFAOYSA-N 0.000 description 1
- SKALKWDLWMKOTE-UHFFFAOYSA-N ethyl 4-[2-[(4-acetylanilino)methyl]-6-methoxyphenoxy]butanoate Chemical compound C1=CC=C(OC)C(OCCCC(=O)OCC)=C1CNC1=CC=C(C(C)=O)C=C1 SKALKWDLWMKOTE-UHFFFAOYSA-N 0.000 description 1
- LIGLMLGNRWTJBX-UHFFFAOYSA-N ethyl 4-[4-(hydroxymethyl)-2-methoxyphenoxy]butanoate Chemical compound CCOC(=O)CCCOC1=CC=C(CO)C=C1OC LIGLMLGNRWTJBX-UHFFFAOYSA-N 0.000 description 1
- LPLPUZDQDMOIMN-UHFFFAOYSA-N ethyl 4-[4-(hydroxymethyl)phenoxy]butanoate Chemical compound CCOC(=O)CCCOC1=CC=C(CO)C=C1 LPLPUZDQDMOIMN-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002270 exclusion chromatography Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000002360 granulocyte-macrophage progenitor cell Anatomy 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 230000003394 haemopoietic effect Effects 0.000 description 1
- 229940028332 halog Drugs 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000004408 hybridoma Anatomy 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229940127121 immunoconjugate Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 150000002669 lysines Chemical class 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- FJAKFRLDCQWYFJ-UHFFFAOYSA-N methyl 4-(4-formyl-2-methoxyphenoxy)butanoate Chemical compound COC(=O)CCCOC1=CC=C(C=O)C=C1OC FJAKFRLDCQWYFJ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 231100000324 minimal toxicity Toxicity 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 201000000050 myeloid neoplasm Diseases 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012898 sample dilution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- RPENMORRBUTCPR-UHFFFAOYSA-M sodium;1-hydroxy-2,5-dioxopyrrolidine-3-sulfonate Chemical compound [Na+].ON1C(=O)CC(S([O-])(=O)=O)C1=O RPENMORRBUTCPR-UHFFFAOYSA-M 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
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000002992 thymic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000000954 titration curve Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 125000004954 trialkylamino group Chemical group 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- ZENOXNGFMSCLLL-UHFFFAOYSA-N vanillyl alcohol Chemical compound COC1=CC(CO)=CC=C1O ZENOXNGFMSCLLL-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/395—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/68—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
- A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
- A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
- A61K47/6807—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug or compound being a sugar, nucleoside, nucleotide, nucleic acid, e.g. RNA antisense
- A61K47/6809—Antibiotics, e.g. antitumor antibiotics anthracyclins, adriamycin, doxorubicin or daunomycin
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25387794 | 1994-06-03 | ||
| US08/253,877 US5773001A (en) | 1994-06-03 | 1994-06-03 | Conjugates of methyltrithio antitumor agents and intermediates for their synthesis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI952720A0 FI952720A0 (fi) | 1995-06-02 |
| FI952720A FI952720A (fi) | 1995-12-04 |
| FI117690B true FI117690B (fi) | 2007-01-31 |
Family
ID=22962074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI952720A FI117690B (fi) | 1994-06-03 | 1995-06-02 | Kasvainten vastaisten metyylitritioyhdisteiden konjugaatteja ja välituotteita niiden synteesiä varten |
Country Status (20)
| Country | Link |
|---|---|
| US (4) | US5773001A (ja) |
| EP (1) | EP0689845B1 (ja) |
| JP (2) | JP3650165B2 (ja) |
| KR (1) | KR100408376B1 (ja) |
| AT (1) | ATE223234T1 (ja) |
| AU (1) | AU697280B2 (ja) |
| BR (2) | BR1101078A (ja) |
| CA (1) | CA2150785C (ja) |
| CY (1) | CY2334B1 (ja) |
| DE (1) | DE69528016T2 (ja) |
| DK (1) | DK0689845T3 (ja) |
| ES (1) | ES2181752T3 (ja) |
| FI (1) | FI117690B (ja) |
| IL (1) | IL113984A (ja) |
| NO (1) | NO313617B1 (ja) |
| NZ (3) | NZ272274A (ja) |
| PT (1) | PT689845E (ja) |
| SI (1) | SI0689845T1 (ja) |
| TW (1) | TW394778B (ja) |
| ZA (1) | ZA954570B (ja) |
Families Citing this family (719)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5773001A (en) * | 1994-06-03 | 1998-06-30 | American Cyanamid Company | Conjugates of methyltrithio antitumor agents and intermediates for their synthesis |
| US5712374A (en) * | 1995-06-07 | 1998-01-27 | American Cyanamid Company | Method for the preparation of substantiallly monomeric calicheamicin derivative/carrier conjugates |
| US5714586A (en) * | 1995-06-07 | 1998-02-03 | American Cyanamid Company | Methods for the preparation of monomeric calicheamicin derivative/carrier conjugates |
| AU2335899A (en) * | 1998-01-29 | 1999-08-16 | Pharmacopeia, Inc. | Acid cleavable phenoxyalkyl linker for combinatorial synthesis |
| US6008321A (en) * | 1998-03-16 | 1999-12-28 | Pharmacopeia, Inc. | Universal linker for combinatorial synthesis |
| US6914130B2 (en) * | 1998-06-17 | 2005-07-05 | Genentech, Inc. | Compositions and methods for the diagnosis and treatment of tumor |
| US6733998B1 (en) | 1998-12-07 | 2004-05-11 | Sloan-Kettering Institute For Cancer Research | Micromonospora echinospora genes coding for biosynthesis of calicheamicin and self-resistance thereto |
| US20050159588A1 (en) * | 1999-06-02 | 2005-07-21 | Genentech, Inc. | Compositions and methods for the diagnosis and treatment of tumor |
| AU784045B2 (en) | 1999-06-25 | 2006-01-19 | Genentech Inc. | Humanized anti-ErbB2 antibodies and treatment with anti-ErbB2 antibodies |
| PT1240337E (pt) * | 1999-12-24 | 2007-01-31 | Genentech Inc | Métodos e composições para prolongar as meias-vidas de eliminação de compostos bioactivos |
| US20040001827A1 (en) * | 2002-06-28 | 2004-01-01 | Dennis Mark S. | Serum albumin binding peptides for tumor targeting |
| US20060228364A1 (en) * | 1999-12-24 | 2006-10-12 | Genentech, Inc. | Serum albumin binding peptides for tumor targeting |
| US20050287153A1 (en) * | 2002-06-28 | 2005-12-29 | Genentech, Inc. | Serum albumin binding peptides for tumor targeting |
| JP2003520828A (ja) * | 2000-01-27 | 2003-07-08 | ジェネティクス インスティテュート，エルエルシー | Ｃｔｌａ４（ｃｄ１５２）に対する抗体、これを含む結合体、およびその使用 |
| EP1272647B1 (en) | 2000-04-11 | 2014-11-12 | Genentech, Inc. | Multivalent antibodies and uses therefor |
| EP1355918B9 (en) | 2000-12-28 | 2012-01-25 | Wyeth LLC | Recombinant protective protein from $i(streptococcus pneumoniae) |
| US6652853B2 (en) * | 2001-03-08 | 2003-11-25 | Ludwig Institute For Cancer Research | Method for treating cancer using A33 specific antibodies and chemotherapeutic agents |
| NZ511705A (en) * | 2001-05-14 | 2004-03-26 | Horticulture & Food Res Inst | Methods and rapid immunoassay device for detecting progesterone and other steroids |
| AU2002303929B9 (en) * | 2001-05-31 | 2007-01-25 | E. R. Squibb & Sons, L.L.C. | Cytotoxins, prodrugs, linkers and stabilizers useful therefor |
| US20070160576A1 (en) | 2001-06-05 | 2007-07-12 | Genentech, Inc. | IL-17A/F heterologous polypeptides and therapeutic uses thereof |
| EP2000482A1 (en) | 2001-06-20 | 2008-12-10 | Genentech, Inc. | Compositions and methods for the diagnosis and treatment of tumor |
| US7803915B2 (en) | 2001-06-20 | 2010-09-28 | Genentech, Inc. | Antibody compositions for the diagnosis and treatment of tumor |
| US20050107595A1 (en) * | 2001-06-20 | 2005-05-19 | Genentech, Inc. | Compositions and methods for the diagnosis and treatment of tumor |
| US20040086504A1 (en) * | 2001-06-21 | 2004-05-06 | Deepak Sampath | Cyr61 as a target for treatment and diagnosis of breast cancer |
| US20040235068A1 (en) * | 2001-09-05 | 2004-11-25 | Levinson Arthur D. | Methods for the identification of polypeptide antigens associated with disorders involving aberrant cell proliferation and compositions useful for the treatment of such disorders |
| NZ531674A (en) | 2001-09-18 | 2009-03-31 | Genentech Inc | Compositions and methods for the diagnosis and treatment of tumor |
| US20040023910A1 (en) * | 2001-09-28 | 2004-02-05 | Zhiming Zhang | Use of cyr61 in the treatment and diagnosis of human uterine leiomyomas |
| US20110045005A1 (en) | 2001-10-19 | 2011-02-24 | Craig Crowley | Compositions and methods for the treatment of tumor of hematopoietic origin |
| KR100623128B1 (ko) | 2002-01-02 | 2006-09-14 | 제넨테크, 인크. | 종양의 진단 및 치료 방법 및 이를 위한 조성물 |
| US7662925B2 (en) * | 2002-03-01 | 2010-02-16 | Xencor, Inc. | Optimized Fc variants and methods for their generation |
| US20100311954A1 (en) * | 2002-03-01 | 2010-12-09 | Xencor, Inc. | Optimized Proteins that Target Ep-CAM |
| US20090042291A1 (en) * | 2002-03-01 | 2009-02-12 | Xencor, Inc. | Optimized Fc variants |
| US20040132101A1 (en) | 2002-09-27 | 2004-07-08 | Xencor | Optimized Fc variants and methods for their generation |
| AU2003230874A1 (en) | 2002-04-16 | 2003-11-03 | Genentech, Inc. | Compositions and methods for the diagnosis and treatment of tumor |
| EP2371392B1 (en) | 2002-05-02 | 2015-07-08 | Wyeth Holdings LLC | Calicheamicin derivative-carrier conjugates |
| ES2392525T3 (es) | 2002-07-15 | 2012-12-11 | F. Hoffmann-La Roche Ag | Tratamiento del cáncer con el anticuerpo dirigido contra ErbB2 rhuMAb 2C4 |
| EP3502133A1 (en) | 2002-09-27 | 2019-06-26 | Xencor, Inc. | Optimized fc variants and methods for their generation |
| PT2891666T (pt) | 2002-10-16 | 2017-09-22 | Purdue Pharma Lp | Anticorpos que se ligam ca 125/0722p associado a células e métodos para a sua utilização |
| US20040152632A1 (en) * | 2002-11-06 | 2004-08-05 | Wyeth | Combination therapy for the treatment of acute leukemia and myelodysplastic syndrome |
| US20090010920A1 (en) * | 2003-03-03 | 2009-01-08 | Xencor, Inc. | Fc Variants Having Decreased Affinity for FcyRIIb |
| US8388955B2 (en) * | 2003-03-03 | 2013-03-05 | Xencor, Inc. | Fc variants |
| MXPA06000347A (es) | 2003-07-08 | 2006-03-28 | Genentech Inc | Polipeptidos heterologos il-17 a/f y usos terapeuticos de los mismos. |
| KR101204247B1 (ko) | 2003-07-22 | 2012-11-22 | 아스텍스 테라퓨틱스 리미티드 | 3,4-이치환된 1ｈ-피라졸 화합물 및 그의 시클린 의존성키나제 (ｃｄｋ) 및 글리코겐 합성효소 키나제-3(ｇｓｋ-3) 조정제로서 용도 |
| WO2005086612A2 (en) * | 2003-07-29 | 2005-09-22 | Immunomedics, Inc. | Fluorinated carbohydrate conjugates |
| CA2534055A1 (en) * | 2003-08-01 | 2005-02-10 | Genentech, Inc. | Antibody cdr polypeptide sequences with restricted diversity |
| US8101720B2 (en) * | 2004-10-21 | 2012-01-24 | Xencor, Inc. | Immunoglobulin insertions, deletions and substitutions |
| US9714282B2 (en) | 2003-09-26 | 2017-07-25 | Xencor, Inc. | Optimized Fc variants and methods for their generation |
| US20050282168A1 (en) * | 2003-09-29 | 2005-12-22 | Wyeth | Cell surface molecules as markers and therapeutic agents against kidney cancers |
| BR122018071808B8 (pt) | 2003-11-06 | 2020-06-30 | Seattle Genetics Inc | conjugado |
| EP1689432B1 (en) | 2003-11-17 | 2009-12-30 | Genentech, Inc. | Compositions and methods for the treatment of tumor of hematopoietic origin |
| AU2004309347B2 (en) | 2003-12-19 | 2010-03-04 | Genentech, Inc. | Monovalent antibody fragments useful as therapeutics |
| TW200539855A (en) * | 2004-03-15 | 2005-12-16 | Wyeth Corp | Calicheamicin conjugates |
| JP5128935B2 (ja) | 2004-03-31 | 2013-01-23 | ジェネンテック， インコーポレイテッド | ヒト化抗ＴＧＦ−β抗体 |
| WO2005101017A1 (en) * | 2004-04-07 | 2005-10-27 | Genentech, Inc. | Mass spectrometry of antibody conjugates |
| US7691962B2 (en) * | 2004-05-19 | 2010-04-06 | Medarex, Inc. | Chemical linkers and conjugates thereof |
| JP4806680B2 (ja) * | 2004-05-19 | 2011-11-02 | メダレックス インコーポレイテッド | 自己犠牲リンカー及び薬剤複合体 |
| BRPI0510883B8 (pt) | 2004-06-01 | 2021-05-25 | Genentech Inc | composto conjugado de droga e anticorpo, composição farmacêutica, método de fabricação de composto conjugado de droga e anticorpo e usos de uma formulação, de um conjugado de droga e anticorpo e um agente quimioterapêutico e de uma combinação |
| EP2471813B1 (en) | 2004-07-15 | 2014-12-31 | Xencor, Inc. | Optimized Fc variants |
| BRPI0513534A (pt) | 2004-07-20 | 2008-05-06 | Genentech Inc | inibidores de proteìna 4 semelhante à angiopoietina, combinações, e seu uso |
| EP1774022B1 (en) | 2004-07-26 | 2014-12-31 | Genentech, Inc. | Methods and compositions for modulating hepatocyte growth factor activation |
| US20060045877A1 (en) * | 2004-08-30 | 2006-03-02 | Goldmakher Viktor S | Immunoconjugates targeting syndecan-1 expressing cells and use thereof |
| RU2453558C2 (ru) * | 2004-09-03 | 2012-06-20 | Дженентек, Инк. | Гуманизированные антагонистические антитела против бета7 и их применение |
| PE20060817A1 (es) * | 2004-09-10 | 2006-10-10 | Wyeth Corp | Anticuerpos anti-5t4 humanizados y conjugados anticuerpo anti-5t4/calicheamicina |
| CA2580141C (en) | 2004-09-23 | 2013-12-10 | Genentech, Inc. | Cysteine engineered antibodies and conjugates |
| BRPI0516577A (pt) * | 2004-10-05 | 2008-09-16 | Genentech Inc | agentes terapêuticos com toxicidade diminuìda |
| JO3000B1 (ar) | 2004-10-20 | 2016-09-05 | Genentech Inc | مركبات أجسام مضادة . |
| US8546543B2 (en) | 2004-11-12 | 2013-10-01 | Xencor, Inc. | Fc variants that extend antibody half-life |
| US8802820B2 (en) * | 2004-11-12 | 2014-08-12 | Xencor, Inc. | Fc variants with altered binding to FcRn |
| US20070135620A1 (en) * | 2004-11-12 | 2007-06-14 | Xencor, Inc. | Fc variants with altered binding to FcRn |
| EP2845865A1 (en) | 2004-11-12 | 2015-03-11 | Xencor Inc. | Fc variants with altered binding to FcRn |
| US8367805B2 (en) * | 2004-11-12 | 2013-02-05 | Xencor, Inc. | Fc variants with altered binding to FcRn |
| WO2006060533A2 (en) | 2004-12-01 | 2006-06-08 | Genentech, Inc. | Conjugates of 1, 8-bis-naphthalimides with an antibody |
| EP1841793B1 (en) | 2005-01-07 | 2010-03-31 | Diadexus, Inc. | Ovr110 antibody compositions and methods of use |
| AR054425A1 (es) | 2005-01-21 | 2007-06-27 | Astex Therapeutics Ltd | Sales de adicion de piperidin 4-il- amida de acido 4-(2,6-dicloro-benzoilamino) 1h-pirazol-3-carboxilico. |
| BRPI0518104B8 (pt) | 2005-01-21 | 2021-05-25 | Genentech Inc | artigo industrializado e uso de anticorpo her2 |
| JP5475235B2 (ja) | 2005-01-21 | 2014-04-16 | アステックス・セラピューティクス・リミテッド | 医薬化合物 |
| US8404718B2 (en) | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
| DK1851250T3 (da) * | 2005-02-18 | 2012-07-09 | Medarex Inc | Humant monoklonalt antistof mod prostataspecifikt membranantigen (psma) |
| UA95902C2 (ru) | 2005-02-23 | 2011-09-26 | Дженентек, Инк. | Способ увеличения времени развития заболевания или выживаемости у раковых пациентов |
| WO2006096861A2 (en) * | 2005-03-08 | 2006-09-14 | Genentech, Inc. | METHODS FOR IDENTIFYING TUMORS RESPONSIVE TO TREATMENT WITH HER DIMERIZATION INHIBITORS (HDIs) |
| WO2006110599A2 (en) | 2005-04-07 | 2006-10-19 | Novartis Vaccines And Diagnostics Inc. | Cacna1e in cancer diagnosis, detection and treatment |
| JP2008535853A (ja) | 2005-04-07 | 2008-09-04 | ノバルティス ヴァクシンズ アンド ダイアグノスティクス インコーポレイテッド | 癌関連遺伝子 |
| US7714016B2 (en) * | 2005-04-08 | 2010-05-11 | Medarex, Inc. | Cytotoxic compounds and conjugates with cleavable substrates |
| US7858843B2 (en) | 2005-06-06 | 2010-12-28 | Genentech, Inc. | Gene disruptions, compositions and methods relating thereto |
| US20070003559A1 (en) * | 2005-07-01 | 2007-01-04 | Wyeth | Methods of determining pharmacokinetics of targeted therapies |
| US7557190B2 (en) | 2005-07-08 | 2009-07-07 | Xencor, Inc. | Optimized proteins that target Ep-CAM |
| JP2009504183A (ja) | 2005-08-15 | 2009-02-05 | ジェネンテック・インコーポレーテッド | 遺伝子破壊、それに関連する組成物および方法 |
| EP1937311A2 (en) | 2005-09-30 | 2008-07-02 | The Government of the United States of America, as represented by the Secretary of the Department of Health and Human Services | Methods and compositions for modulating immune tolerance |
| CA2624189A1 (en) | 2005-10-03 | 2007-04-12 | Xencor, Inc. | Fc variants with optimized fc receptor binding properties |
| JP5116686B2 (ja) | 2005-10-26 | 2013-01-09 | メダレックス インコーポレイテッド | Ｃｃ−１０６５類似体の調製方法及び調製用化合物 |
| EP1957531B1 (en) | 2005-11-07 | 2016-04-13 | Genentech, Inc. | Binding polypeptides with diversified and consensus vh/vl hypervariable sequences |
| CA2627190A1 (en) | 2005-11-10 | 2007-05-24 | Medarex, Inc. | Duocarmycin derivatives as novel cytotoxic compounds and conjugates |
| CA2630432A1 (en) | 2005-11-21 | 2007-07-19 | Genentech, Inc. | Novel gene disruptions, compositions and methods relating thereto |
| ES2388932T3 (es) * | 2005-12-02 | 2012-10-19 | Genentech, Inc. | Polipéptidos de unión y usos de los mismos |
| NZ621483A (en) | 2005-12-02 | 2015-10-30 | Genentech Inc | Compositions and methods for the treatment of diseases and disorders associated with cytokine signaling involving antibodies that bind to il-22 and il-22r |
| US20070237764A1 (en) * | 2005-12-02 | 2007-10-11 | Genentech, Inc. | Binding polypeptides with restricted diversity sequences |
| WO2007067602A1 (en) * | 2005-12-06 | 2007-06-14 | Wyeth | Interleukin-11 compositions and methods of use |
| EP2325208B1 (en) | 2005-12-15 | 2017-09-20 | Genentech, Inc. | Polyubiquitin antibodies |
| TWI596111B (zh) | 2006-01-05 | 2017-08-21 | 建南德克公司 | 抗ｅｐｈｂ４抗體及使用該抗體之方法 |
| EP1988768A2 (en) | 2006-02-17 | 2008-11-12 | Genentech, Inc. | Gene disruptions, compositions and methods relating thereto |
| AU2012261705B2 (en) * | 2006-02-21 | 2014-02-06 | Wyeth Llc | Processes for the convergent synthesis of calicheamicin derivatives |
| AU2014202414B2 (en) * | 2006-02-21 | 2016-06-02 | Wyeth Llc | Processes for the convergent synthesis of calicheamicin derivatives |
| TW200806685A (en) * | 2006-02-21 | 2008-02-01 | Wyeth Corp | Processes for the convergent synthesis of calicheamicin derivatives |
| WO2007103522A2 (en) | 2006-03-08 | 2007-09-13 | Wake Forest University Health Sciences | Soluble monomeric ephrin a1 |
| KR101443752B1 (ko) | 2006-03-10 | 2014-09-26 | 와이어쓰 엘엘씨 | 항-５ｔ４ 항체 및 이의 용도 |
| AR059851A1 (es) | 2006-03-16 | 2008-04-30 | Genentech Inc | Anticuerpos de la egfl7 y metodos de uso |
| MX2008012013A (es) | 2006-03-23 | 2008-10-03 | Novartis Ag | Tratamiento con anticuerpo antigeno de celulas neoplasicas. |
| EP2007428A2 (en) | 2006-04-05 | 2008-12-31 | Genentech, Inc. | Method for using boc/cdo to modulate hedgehog signaling |
| EP2407483A1 (en) | 2006-04-13 | 2012-01-18 | Novartis Vaccines and Diagnostics, Inc. | Methods of treating, diagnosing or detecting cancers |
| US20090288176A1 (en) | 2006-04-19 | 2009-11-19 | Genentech, Inc. | Novel Gene Disruptions, Compositions and Methods Relating Thereto |
| WO2007134132A2 (en) * | 2006-05-12 | 2007-11-22 | Genentech, Inc. | Compositions and methods for the diagnosis and treatment of bladder and urinary tract tumors |
| WO2007140371A2 (en) | 2006-05-30 | 2007-12-06 | Genentech, Inc. | Antibodies and immunoconjugates and uses therefor |
| ES2402591T3 (es) | 2006-08-14 | 2013-05-07 | Xencor Inc. | Anticuerpos optimizados que seleccionan como diana CD19 |
| EP2061906B1 (en) | 2006-09-12 | 2011-08-31 | Genentech, Inc. | Methods and compositions for the diagnosis and treatment of lung cancer using pdgfra, kit or kdr gene as genetic marker |
| US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
| WO2008044045A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| RU2639543C9 (ru) | 2006-10-27 | 2018-06-14 | Дженентек, Инк. | Антитела и иммуноконъюгаты и их применения |
| WO2008067283A2 (en) | 2006-11-27 | 2008-06-05 | Diadexus, Inc. | Ovr110 antibody compositions and methods of use |
| TWI412367B (zh) | 2006-12-28 | 2013-10-21 | Medarex Llc | 化學鏈接劑與可裂解基質以及其之綴合物 |
| AR065271A1 (es) | 2007-02-09 | 2009-05-27 | Genentech Inc | Anticuerpos anti-robo4 y sus usos |
| EP2121667B1 (en) | 2007-02-21 | 2016-06-08 | E. R. Squibb & Sons, L.L.C. | Chemical linkers with single amino acids and conjugates thereof |
| CA2677108A1 (en) * | 2007-03-02 | 2008-09-12 | Genentech, Inc. | Predicting response to a her inhibitor |
| WO2008112988A2 (en) | 2007-03-14 | 2008-09-18 | Novartis Ag | Apcdd1 inhibitors for treating, diagnosing or detecting cancer |
| US7960139B2 (en) | 2007-03-23 | 2011-06-14 | Academia Sinica | Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells |
| US7928202B2 (en) | 2007-04-12 | 2011-04-19 | The Brigham And Women's Hospital, Inc. | Targeting ABCB5 for cancer therapy |
| EP2708557A1 (en) | 2007-05-30 | 2014-03-19 | Xencor, Inc. | Method and compositions for inhibiting CD32B expressing cells |
| PE20090321A1 (es) | 2007-06-04 | 2009-04-20 | Genentech Inc | Anticuerpos anti-notch1 nrr, metodo de preparacion y composicion farmaceutica |
| ES2579323T3 (es) | 2007-07-16 | 2016-08-09 | Genentech, Inc. | Anticuerpos anti-CD79B e inmunoconjugados y métodos de uso |
| AU2008276128B2 (en) | 2007-07-16 | 2013-10-10 | Genentech, Inc. | Humanized anti-CD79b antibodies and immunoconjugates and methods of use |
| WO2009041613A1 (ja) | 2007-09-26 | 2009-04-02 | Chugai Seiyaku Kabushiki Kaisha | 抗体定常領域改変体 |
| ES2502217T3 (es) | 2007-10-02 | 2014-10-03 | Genentech, Inc. | Antagonistas de NLRR-1 y sus usos |
| US20110033476A1 (en) * | 2007-11-12 | 2011-02-10 | Theraclone Sciences Inc. | Compositions and methods for the therapy and diagnosis of influenza |
| MX2010005244A (es) * | 2007-11-12 | 2010-10-25 | Theraclone Sciences Inc | Composiciones y métodos para la terapia y el diagnóstico de influenza. |
| TWI468417B (zh) | 2007-11-30 | 2015-01-11 | Genentech Inc | 抗－ｖｅｇｆ抗體 |
| US9011864B2 (en) * | 2007-12-26 | 2015-04-21 | Biotest Ag | Method of decreasing cytotoxic side-effects and improving efficacy of immunoconjugates |
| KR20100097753A (ko) * | 2007-12-26 | 2010-09-03 | 바이오테스트 아게 | Ｃｄ138 표적성 면역접합체 및 이의 용도 |
| JP2011508738A (ja) * | 2007-12-26 | 2011-03-17 | バイオテスト・アクチエンゲゼルシヤフト | Ｃｄ１３８発現腫瘍細胞のターゲティングを向上させる方法及び剤 |
| EP3825329A1 (en) | 2007-12-26 | 2021-05-26 | Xencor, Inc. | Fc variants with altered binding to fcrn |
| MX341344B (es) | 2007-12-26 | 2016-08-16 | Biotest Ag | Agentes dirigidos a cd138 y sus usos. |
| BRPI0907046A2 (pt) | 2008-01-18 | 2015-07-28 | Medimmune Llc | Anticorpo de cisteína engenheirada, ácido nucleico isolado, vetor, célula hospedeira, conjugado de anticorpo, composição farmacêutica, métodos de detecção de câncer, doenças ou distúrbios autoimunes, inflamatórios ou infecciosos em um indivíduo e de inibição de proliferação de uma célula alvo |
| TWI472339B (zh) | 2008-01-30 | 2015-02-11 | Genentech Inc | 包含結合至ｈｅｒ２結構域ii之抗體及其酸性變異體的組合物 |
| CL2009000062A1 (es) | 2008-01-31 | 2010-05-14 | Genentech Inc | Anticuerpo humanizado anti cd79b; con modificaciones de cisterna libre; inmunoconjugado que contiene dicho anticuerpo y una droga; polinucleotido que codifica el anticuerpo; vector, celula huesped; composicion farmaceutica y uso de dicha composicion para tratar cancer, preferentemente linfomas. |
| CA2718878A1 (en) * | 2008-03-10 | 2009-09-17 | Theraclone Sciences, Inc. | Compositions and methods for the therapy and diagnosis of cytomegalovirus |
| EP2631302A3 (en) * | 2008-03-31 | 2014-01-08 | Genentech, Inc. | Compositions and methods for treating and diagnosing asthma |
| SG10201402815VA (en) | 2008-04-09 | 2014-09-26 | Genentech Inc | Novel compositions and methods for the treatment of immune related diseases |
| CN102124344B (zh) * | 2008-05-16 | 2015-04-01 | 霍夫曼-拉罗奇有限公司 | 生物标记用于评估β7整联蛋白拮抗剂治疗胃肠道炎性病症的用途 |
| WO2010009271A2 (en) | 2008-07-15 | 2010-01-21 | Academia Sinica | Glycan arrays on ptfe-like aluminum coated glass slides and related methods |
| CA2737146A1 (en) | 2008-07-25 | 2010-01-28 | The Regents Of The University Of Colorado | Clip inhibitors and methods of modulating immune function |
| TW201018484A (en) | 2008-10-01 | 2010-05-16 | Genentech Inc | Anti-Notch2 antibodies and methods of use |
| MX2011006516A (es) | 2008-12-17 | 2011-08-04 | Genentech Inc | Terapia de combinacion de virus de hepatitis c. |
| EP3243835B1 (en) | 2009-02-11 | 2024-04-10 | Albumedix Ltd | Albumin variants and conjugates |
| SI3260136T1 (sl) | 2009-03-17 | 2021-05-31 | Theraclone Sciences, Inc. | Humani imunodeficientni virus (HIV)-nevtralizirajoča protitelesa |
| RU2504553C2 (ru) | 2009-03-20 | 2014-01-20 | Дженентек, Инк. | Антитела к her |
| MX2011010012A (es) | 2009-03-25 | 2011-12-06 | Genentech Inc | NUEVOS ANTICUERPOS ANTI-A5ß1 Y SUS USOS. |
| HUE025726T2 (en) * | 2009-03-25 | 2016-04-28 | Genentech Inc | Anti-FGFR3 antibodies and their use |
| PE20120878A1 (es) | 2009-04-01 | 2012-08-06 | Genentech Inc | ANTICUERPOS ANTI-FcRH5 E INMUNOCONJUGADOS |
| RU2598248C2 (ru) | 2009-04-02 | 2016-09-20 | Роше Гликарт Аг | Полиспецифичные антитела, включающие антитела полной длины и одноцепочечные фрагменты fab |
| RU2595379C2 (ru) | 2009-04-16 | 2016-08-27 | АббВай Биотерапеутикс Инк. | АНТИТЕЛА ПРОТИВ TNF-α И ИХ ПРИМЕНЕНИЯ |
| US9296785B2 (en) | 2009-04-17 | 2016-03-29 | Wake Forest University Health Sciences | IL-13 receptor binding peptides |
| CN102459340A (zh) * | 2009-04-23 | 2012-05-16 | 特罗科隆科学有限公司 | 粒性白血细胞-巨噬细胞菌落-刺激因子(gm-csf)中和抗体 |
| US8858948B2 (en) | 2009-05-20 | 2014-10-14 | Theraclone Sciences, Inc. | Compositions and methods for the therapy and diagnosis of influenza |
| PL2896404T3 (pl) | 2009-06-04 | 2017-12-29 | Novartis Ag | Sposoby identyfikacji miejsc koniugacji IgG |
| AU2010262836B2 (en) | 2009-06-17 | 2015-05-28 | Abbvie Biotherapeutics Inc. | Anti-VEGF antibodies and their uses |
| WO2011005481A1 (en) | 2009-06-22 | 2011-01-13 | Medimmune, Llc | ENGINEERED Fc REGIONS FOR SITE-SPECIFIC CONJUGATION |
| MX2012001306A (es) | 2009-07-31 | 2012-02-28 | Genentech Inc | Inhibicion de matastasis de tumor. |
| ES2599076T3 (es) | 2009-09-02 | 2017-01-31 | Genentech, Inc. | Smoothened mutante y métodos de utilización del mismo |
| US9493578B2 (en) | 2009-09-02 | 2016-11-15 | Xencor, Inc. | Compositions and methods for simultaneous bivalent and monovalent co-engagement of antigens |
| CA2781519A1 (en) | 2009-09-16 | 2011-03-24 | Genentech, Inc. | Coiled coil and/or tether containing protein complexes and uses thereof |
| IN2012DN02780A (ja) | 2009-10-06 | 2015-09-18 | Immunogen Inc | |
| PL2488873T3 (pl) | 2009-10-16 | 2016-01-29 | Novartis Ag | Biomarkery odpowiedzi farmakodynamicznej wobec guza |
| US8759491B2 (en) * | 2009-10-19 | 2014-06-24 | Genentech, Inc. | Modulators of hepatocyte growth factor activator |
| BR112012009409A2 (pt) | 2009-10-22 | 2017-02-21 | Genentech Inc | método de identificação de uma substância inibidora, molécula antagonista, ácido nucleico isolado, vetor, célula hospedeira, método para fabricar a molécula, composição, artigo de fabricação, método de inibição de uma atividade biológica, método de tratamento de uma condição patológica, método para detectar msp em uma amostra e método para detectar hepsina em uma amostra |
| US8435511B2 (en) | 2009-10-22 | 2013-05-07 | Genentech, Inc. | Anti-hepsin antibodies and methods using same |
| WO2011056502A1 (en) | 2009-10-26 | 2011-05-12 | Genentech, Inc. | Bone morphogenetic protein receptor type ii compositions and methods of use |
| WO2011056494A1 (en) | 2009-10-26 | 2011-05-12 | Genentech, Inc. | Activin receptor-like kinase-1 antagonist and vegfr3 antagonist combinations |
| WO2011056497A1 (en) | 2009-10-26 | 2011-05-12 | Genentech, Inc. | Activin receptor type iib compositions and methods of use |
| CN102753580A (zh) | 2009-10-28 | 2012-10-24 | 亚培生物医疗股份有限公司 | 抗egfr抗体及其用途 |
| CA2776241A1 (en) | 2009-10-30 | 2011-05-05 | Novozymes Biopharma Dk A/S | Albumin variants |
| SI2496601T1 (sl) | 2009-11-05 | 2017-09-29 | F. Hoffmann-La Roche Ag | Tehnike in sestavek za sekrecijo heterolognih polipeptidov |
| TWI507524B (zh) | 2009-11-30 | 2015-11-11 | Genentech Inc | 診斷及治療腫瘤之組合物及方法 |
| US10087236B2 (en) | 2009-12-02 | 2018-10-02 | Academia Sinica | Methods for modifying human antibodies by glycan engineering |
| US11377485B2 (en) | 2009-12-02 | 2022-07-05 | Academia Sinica | Methods for modifying human antibodies by glycan engineering |
| RU2580038C2 (ru) | 2009-12-04 | 2016-04-10 | Дженентек, Инк. | Мультиспецифические антитела, аналоги антител, композиции и способы |
| WO2011070024A1 (en) | 2009-12-10 | 2011-06-16 | F. Hoffmann-La Roche Ag | Antibodies binding preferentially human csf1r extracellular domain 4 and their use |
| TWI505836B (zh) | 2009-12-11 | 2015-11-01 | Genentech Inc | 抗－ｖｅｇｆ－ｃ抗體及其使用方法 |
| ES2594893T3 (es) | 2009-12-16 | 2016-12-23 | Abbvie Biotherapeutics Inc. | Anticuerpos anti HER2 y sus usos |
| JP5944831B2 (ja) | 2009-12-23 | 2016-07-05 | シュニムネ ゲーエムベーハーＳＹＮＩＭＭＵＮＥ ＧｍｂＨ | 抗ｆｌｔ３抗体及びその使用方法 |
| HUE027713T2 (en) | 2009-12-23 | 2016-10-28 | Hoffmann La Roche | Anti-BV8 antibodies and their use |
| WO2011089211A1 (en) | 2010-01-22 | 2011-07-28 | Synimmune Gmbh | Anti-cd133 antibodies and methods of using the same |
| DK2531206T3 (en) | 2010-02-04 | 2017-09-11 | Morphotek Inc | CHLOROTOXIN POLYPEPTIDES AND CONJUGATES AND USE THEREOF |
| TWI504410B (zh) | 2010-02-08 | 2015-10-21 | Agensys Inc | 結合至１６１ｐ２ｆ１０ｂ蛋白之抗體藥物結合物（ａｄｃ） |
| SI2536748T1 (sl) | 2010-02-18 | 2014-12-31 | Genentech, Inc. | Nevrogulinski antagonisti in njihova uporaba pri zdravljenju raka |
| WO2011106297A2 (en) | 2010-02-23 | 2011-09-01 | Genentech, Inc. | Compositions and methods for the diagnosis and treatment of tumor |
| KR101656548B1 (ko) | 2010-03-05 | 2016-09-09 | 에프. 호프만-라 로슈 아게 | 인간 ｃｓｆ-1ｒ에 대한 항체 및 이의 용도 |
| KR101647871B1 (ko) | 2010-03-05 | 2016-08-11 | 에프. 호프만-라 로슈 아게 | 인간 ｃｓｆ-1ｒ에 대한 항체 및 이의 용도 |
| CN106432474A (zh) | 2010-03-12 | 2017-02-22 | 艾伯维生物医疗股份有限公司 | Ctla4蛋白和其用途 |
| KR101899835B1 (ko) | 2010-03-24 | 2018-09-19 | 제넨테크, 인크. | 항-ｌｒｐ６ 항체 |
| TW201138821A (en) | 2010-03-26 | 2011-11-16 | Roche Glycart Ag | Bispecific antibodies |
| WO2011124718A1 (en) | 2010-04-09 | 2011-10-13 | Novozymes A/S | Albumin derivatives and variants |
| WO2011130332A1 (en) | 2010-04-12 | 2011-10-20 | Academia Sinica | Glycan arrays for high throughput screening of viruses |
| CA2796633C (en) | 2010-04-23 | 2020-10-27 | Genentech, Inc. | Production of heteromultimeric proteins |
| CN102958941A (zh) | 2010-05-03 | 2013-03-06 | 霍夫曼-拉罗奇有限公司 | 用于肿瘤诊断和治疗的组合物和方法 |
| WO2011146568A1 (en) | 2010-05-19 | 2011-11-24 | Genentech, Inc. | Predicting response to a her inhibitor |
| EP2577310B1 (en) | 2010-06-03 | 2018-11-14 | F.Hoffmann-La Roche Ag | Immuno-pet imaging of antibodies and immunoconjugates and uses therefor |
| RU2626537C2 (ru) | 2010-06-08 | 2017-07-28 | Дженентек, Инк. | Полученные с помощью генной инженерии антитела с цистеиновыми заменами и их конъюгаты |
| TW201204388A (en) | 2010-06-18 | 2012-02-01 | Genentech Inc | Anti-Axl antibodies and methods of use |
| WO2011161119A1 (en) | 2010-06-22 | 2011-12-29 | F. Hoffmann-La Roche Ag | Antibodies against insulin-like growth factor i receptor and uses thereof |
| WO2011161189A1 (en) | 2010-06-24 | 2011-12-29 | F. Hoffmann-La Roche Ag | Anti-hepsin antibodies and methods of use |
| AU2011283694B2 (en) | 2010-07-29 | 2017-04-13 | Xencor, Inc. | Antibodies with modified isoelectric points |
| EP2600895A1 (en) | 2010-08-03 | 2013-06-12 | Hoffmann-La Roche AG | Chronic lymphocytic leukemia (cll) biomarkers |
| EP2603237A4 (en) | 2010-08-12 | 2014-05-21 | Theraclone Sciences Inc | ANTI-HEMAGGLUTININE ANTIBODY COMPOSITIONS AND METHOD FOR THEIR USE |
| PT2603530T (pt) | 2010-08-13 | 2018-01-09 | Roche Glycart Ag | Anticorpos anti-fap e métodos de utilização |
| CN103168049B (zh) | 2010-08-13 | 2015-10-07 | 罗切格利卡特公司 | 抗生腱蛋白-c a2抗体及使用方法 |
| KR20130100125A (ko) | 2010-08-13 | 2013-09-09 | 제넨테크, 인크. | 질환의 치료를 위한, ＩＬ-1β 및 ＩＬ-18에 대한 항체 |
| MX340558B (es) | 2010-08-24 | 2016-07-14 | F Hoffmann-La Roche Ag * | Anticuerpos biespecificos que comprenden fragmento fv estabilizado con disulfuro. |
| CA3059961C (en) | 2010-08-31 | 2021-04-13 | Theraclone Sciences, Inc. | Human immunodeficiency virus (hiv)-neutralizing antibodies |
| SG187886A1 (en) | 2010-08-31 | 2013-04-30 | Genentech Inc | Biomarkers and methods of treatment |
| CN103328511B (zh) | 2010-09-10 | 2016-01-20 | 埃派斯进有限公司 | 抗-IL-1β抗体及其使用方法 |
| MX337873B (es) | 2010-09-29 | 2016-03-23 | Agensys Inc | Conjugados de anticuerpo farmaco (adc) que enlazan a proteinas 191p4d12. |
| WO2012045085A1 (en) | 2010-10-01 | 2012-04-05 | Oxford Biotherapeutics Ltd. | Anti-rori antibodies |
| UA112062C2 (uk) † | 2010-10-04 | 2016-07-25 | Бьорінгер Інгельхайм Інтернаціональ Гмбх | Cd33-зв'язувальний агент |
| ES2588981T3 (es) | 2010-10-05 | 2016-11-08 | Genentech, Inc. | Smoothened mutante y métodos de uso de la misma |
| ES2607086T3 (es) | 2010-11-10 | 2017-03-29 | F. Hoffmann-La Roche Ag | Métodos y composiciones para la inmunoterapia de enfermedades neuronales |
| WO2012065161A2 (en) | 2010-11-12 | 2012-05-18 | Scott & White Healthcare | Antibodies to tumor endothelial marker 8 |
| CA2817380C (en) | 2010-12-16 | 2019-06-04 | Genentech, Inc. | Diagnosis and treatments relating to th2 inhibition |
| TWI589589B (zh) | 2010-12-20 | 2017-07-01 | 建南德克公司 | 抗間皮素（ｍｅｓｏｔｈｅｌｉｎ）抗體及免疫接合物 |
| KR20130118925A (ko) | 2010-12-22 | 2013-10-30 | 제넨테크, 인크. | 항-pcsk9 항체 및 사용 방법 |
| JP5766296B2 (ja) | 2010-12-23 | 2015-08-19 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ポリペプチド−ポリヌクレオチド複合体、およびエフェクター成分の標的化された送達におけるその使用 |
| JOP20210044A1 (ar) | 2010-12-30 | 2017-06-16 | Takeda Pharmaceuticals Co | الأجسام المضادة لـ cd38 |
| WO2012092539A2 (en) | 2010-12-31 | 2012-07-05 | Takeda Pharmaceutical Company Limited | Antibodies to dll4 and uses thereof |
| CN103649117B (zh) | 2011-02-04 | 2016-09-14 | 霍夫曼-拉罗奇有限公司 | Fc变体及其生成方法 |
| US10689447B2 (en) | 2011-02-04 | 2020-06-23 | Genentech, Inc. | Fc variants and methods for their production |
| US20140088019A1 (en) | 2011-02-11 | 2014-03-27 | Zyngenia, Inc. | Monovalent and Multivalent Multispecific Complexes and Uses Thereof |
| EP2675478A4 (en) | 2011-02-14 | 2015-06-10 | Theraclone Sciences Inc | COMPOSITIONS AND METHODS FOR THE THERAPY AND DIAGNOSIS OF GRIP |
| WO2012118813A2 (en) | 2011-03-03 | 2012-09-07 | Apexigen, Inc. | Anti-il-6 receptor antibodies and methods of use |
| AU2012225246B2 (en) | 2011-03-10 | 2016-01-21 | Omeros Corporation | Generation of anti-FN14 monoclonal antibodies by ex-vivo accelerated antibody evolution |
| EP2685968A1 (en) | 2011-03-15 | 2014-01-22 | Theraclone Sciences, Inc. | Compositions and methods for the therapy and diagnosis of influenza |
| WO2012123755A1 (en) | 2011-03-17 | 2012-09-20 | The University Of Birmingham | Re-directed immunotherapy |
| HUE041335T2 (hu) | 2011-03-29 | 2019-05-28 | Roche Glycart Ag | Antitest FC-variánsok |
| CN103596983B (zh) | 2011-04-07 | 2016-10-26 | 霍夫曼-拉罗奇有限公司 | 抗fgfr4抗体及使用方法 |
| BR112013026423A2 (pt) | 2011-04-20 | 2016-11-29 | Roche Glycart Ag | método e construtos para a passagem de pendente do ph da barreira sangue-cérebro |
| EP3508500A1 (en) | 2011-04-29 | 2019-07-10 | Apexigen, Inc. | Anti-cd40 antibodies and methods of use |
| PT2710035T (pt) | 2011-05-16 | 2017-06-05 | Hoffmann La Roche | Agonistas do fgfr1 e métodos de utilização |
| CN106432506A (zh) | 2011-05-24 | 2017-02-22 | 泽恩格尼亚股份有限公司 | 多价和单价多特异性复合物及其用途 |
| US20140105915A1 (en) | 2011-05-27 | 2014-04-17 | Glaxo Group Limited | Bcma (cd269/tnfrsf17) - binding proteins |
| WO2012171020A1 (en) | 2011-06-10 | 2012-12-13 | Mersana Therapeutics, Inc. | Protein-polymer-drug conjugates |
| WO2013003507A1 (en) | 2011-06-27 | 2013-01-03 | Morphotek, Inc. | Multifunctional agents |
| KR20140045440A (ko) | 2011-06-30 | 2014-04-16 | 제넨테크, 인크. | 항-c-met 항체 제제 |
| WO2013022855A1 (en) | 2011-08-05 | 2013-02-14 | Xencor, Inc. | Antibodies with modified isoelectric points and immunofiltering |
| CA2844289C (en) | 2011-08-12 | 2020-01-14 | Omeros Corporation | Anti-fzd10 monoclonal antibodies and methods for their use |
| KR20140057326A (ko) | 2011-08-17 | 2014-05-12 | 제넨테크, 인크. | 뉴레귤린 항체 및 그의 용도 |
| EP2744825A1 (en) | 2011-08-17 | 2014-06-25 | F.Hoffmann-La Roche Ag | Inhibition of angiogenesis in refractory tumors |
| EP2747781B1 (en) | 2011-08-23 | 2017-11-15 | Roche Glycart AG | Bispecific antibodies specific for t-cell activating antigens and a tumor antigen and methods of use |
| KR101886983B1 (ko) | 2011-08-23 | 2018-08-08 | 로슈 글리카트 아게 | 2 개의 ｆａｂ 단편을 포함하는 fc-부재 항체 및 이용 방법 |
| US8822651B2 (en) | 2011-08-30 | 2014-09-02 | Theraclone Sciences, Inc. | Human rhinovirus (HRV) antibodies |
| CA2846083A1 (en) | 2011-09-15 | 2013-03-21 | Genentech, Inc. | Methods of promoting differentiation |
| AU2012312515A1 (en) | 2011-09-19 | 2014-03-13 | Genentech, Inc. | Combination treatments comprising c-met antagonists and B-raf antagonists |
| MX2014002996A (es) | 2011-09-23 | 2014-05-28 | Roche Glycart Ag | Anticuerpos anti - egfr/anti - igf-1r bisespecificos. |
| BR112014008212A2 (pt) | 2011-10-05 | 2017-06-13 | Genentech Inc | método para tratar uma condição hepática, método de indução por diferenciação hepática e método de redução de proliferação anormal do ducto biliar |
| AU2012323287B2 (en) | 2011-10-10 | 2018-02-01 | Xencor, Inc. | A method for purifying antibodies |
| US10851178B2 (en) | 2011-10-10 | 2020-12-01 | Xencor, Inc. | Heterodimeric human IgG1 polypeptides with isoelectric point modifications |
| TW201321414A (zh) | 2011-10-14 | 2013-06-01 | Genentech Inc | 抗－ＨｔｒＡ１抗體及其使用方法 |
| MX355128B (es) | 2011-10-14 | 2018-04-06 | Genentech Inc | Péptidos inhibidores de bace1 y uso de los mismos para el tratamiento de enfermedades o trastornos neurológicos. |
| CA2850836A1 (en) | 2011-10-15 | 2013-04-18 | Genentech, Inc. | Methods of using scd1 antagonists |
| CA2853705C (en) | 2011-10-25 | 2021-10-12 | Memorial Sloan-Kettering Cancer Center | Free psa antibodies as diagnostics, prognostics and therapeutics for prostate cancer |
| MX2014004991A (es) | 2011-10-28 | 2014-05-22 | Genentech Inc | Combinaciones terapeuticas y metodos para tratar el melanoma. |
| TWI571473B (zh) | 2011-11-02 | 2017-02-21 | 埃派斯進有限公司 | 抗ｋｄｒ抗體及使用方法 |
| EP2589609A1 (en) | 2011-11-03 | 2013-05-08 | Pierre Fabre Medicament | Antigen binding protein and its use as addressing product for the treatment of cancer |
| EP2780364A2 (en) | 2011-11-18 | 2014-09-24 | Eleven Biotherapeutics, Inc. | Proteins with improved half-life and other properties |
| TW201326193A (zh) | 2011-11-21 | 2013-07-01 | Genentech Inc | 抗－ｃ－ｍｅｔ抗體之純化 |
| BR112014013694A2 (pt) | 2011-12-08 | 2017-06-13 | Biotest Ag | método para tratar uma doença, e, kit |
| CN104159921B (zh) | 2011-12-15 | 2018-05-04 | 霍夫曼-拉罗奇有限公司 | 针对人csf-1r的抗体及其用途 |
| EP2793941A1 (en) | 2011-12-23 | 2014-10-29 | F.Hoffmann-La Roche Ag | Articles of manufacture and methods for co-administration of antibodies |
| US10774132B2 (en) | 2012-01-09 | 2020-09-15 | The Scripps Research Instittue | Ultralong complementarity determining regions and uses thereof |
| CA2862979A1 (en) | 2012-01-09 | 2013-07-18 | The Scripps Research Institute | Humanized antibodies with ultralong cdr3s |
| CN104168920A (zh) | 2012-01-18 | 2014-11-26 | 霍夫曼-拉罗奇有限公司 | 使用fgf19调控剂的方法 |
| SG11201404198TA (en) | 2012-01-18 | 2014-08-28 | Genentech Inc | Anti-lrp5 antibodies and methods of use |
| WO2013116686A1 (en) | 2012-02-02 | 2013-08-08 | Massachusetts Institute Of Technology | Methods and products related to targeted cancer therapy |
| KR20140127854A (ko) | 2012-02-10 | 2014-11-04 | 제넨테크, 인크. | 단일-쇄 항체 및 다른 이종다량체 |
| AU2013216753B2 (en) | 2012-02-11 | 2017-09-21 | Genentech, Inc. | R-spondin translocations and methods using the same |
| ES2676031T3 (es) | 2012-02-15 | 2018-07-16 | F. Hoffmann-La Roche Ag | Cromatografía de afinidad basada en el receptor Fc |
| GB201203442D0 (en) | 2012-02-28 | 2012-04-11 | Univ Birmingham | Immunotherapeutic molecules and uses |
| US9944691B2 (en) | 2012-03-16 | 2018-04-17 | Albumedix A/S | Albumin variants |
| US10024860B2 (en) | 2012-03-28 | 2018-07-17 | Massachusetts Institute Of Technology | Cancer-related extracellular matrix signatures and related methods and products |
| WO2013148259A1 (en) | 2012-03-28 | 2013-10-03 | Massachusetts Institute Of Technology | Cancer-related extracellular matrix signatures and related methods and products |
| AR090549A1 (es) | 2012-03-30 | 2014-11-19 | Genentech Inc | Anticuerpos anti-lgr5 e inmunoconjugados |
| US10130714B2 (en) | 2012-04-14 | 2018-11-20 | Academia Sinica | Enhanced anti-influenza agents conjugated with anti-inflammatory activity |
| AU2013256596A1 (en) | 2012-05-01 | 2014-10-09 | Genentech, Inc. | Anti-PMEL17 antibodies and immunoconjugates |
| WO2013170191A1 (en) | 2012-05-11 | 2013-11-14 | Genentech, Inc. | Methods of using antagonists of nad biosynthesis from nicotinamide |
| MX2014014830A (es) | 2012-06-15 | 2015-05-11 | Genentech Inc | Anticuerpos anti-pcsk9, formulaciones, dosificacion y metodos de uso. |
| WO2014001325A1 (en) | 2012-06-27 | 2014-01-03 | F. Hoffmann-La Roche Ag | Method for making antibody fc-region conjugates comprising at least one binding entity that specifically binds to a target and uses thereof |
| RU2639287C2 (ru) | 2012-06-27 | 2017-12-20 | Ф. Хоффманн-Ля Рош Аг | Способ отбора и получения высокоселективных и мультиспецифичных нацеливающих групп с заданными свойствами, включающих по меньшей мере две различные связывающие группировки, и их применения |
| CN104395340B9 (zh) | 2012-06-27 | 2018-11-30 | 弗·哈夫曼-拉罗切有限公司 | 包含至少两个不同靶向实体的定制选择性和多特异性治疗分子的方法及其用途 |
| MX353951B (es) | 2012-07-04 | 2018-02-07 | Hoffmann La Roche | Anticuerpos de anti-teofilina y metodos de uso. |
| EP3339328A1 (en) | 2012-07-04 | 2018-06-27 | F. Hoffmann-La Roche AG | Anti-biotin antibodies and methods of use |
| WO2014006124A1 (en) | 2012-07-04 | 2014-01-09 | F. Hoffmann-La Roche Ag | Covalently linked antigen-antibody conjugates |
| PE20150361A1 (es) | 2012-07-13 | 2015-03-14 | Roche Glycart Ag | Anticuerpos biespecificos anti-vegf/anti-ang-2 y su utilizacion en el tratamiento de enfermedades vasculares oculares |
| WO2014031498A1 (en) | 2012-08-18 | 2014-02-27 | Academia Sinica | Cell-permeable probes for identification and imaging of sialidases |
| IL282082B (en) | 2012-08-23 | 2022-08-01 | Seagen Inc | Antibody-drug conjugates (adc) binding to 158p1d7 proteins |
| PL2897978T3 (pl) | 2012-09-19 | 2017-08-31 | Abbvie Biotherapeutics Inc. | Sposoby identyfikacji przeciwciał o obniżonej immunogenności |
| WO2014056783A1 (en) | 2012-10-08 | 2014-04-17 | Roche Glycart Ag | Fc-free antibodies comprising two fab-fragments and methods of use |
| CN115960111A (zh) | 2012-10-11 | 2023-04-14 | 第一三共株式会社 | 抗体－药物偶联物 |
| US9872924B2 (en) | 2012-10-19 | 2018-01-23 | Daiichi Sankyo Company, Limited | Antibody-drug conjugate produced by binding through linker having hydrophilic structure |
| AU2013334102B2 (en) | 2012-10-26 | 2018-08-16 | Memorial Sloan-Kettering Cancer Center | Modulators of resistant androgen receptor |
| KR102270618B1 (ko) | 2012-10-30 | 2021-06-30 | 아펙시젠, 인코포레이티드 | 항-cd40 항체 및 사용 방법 |
| EP2914628A1 (en) | 2012-11-01 | 2015-09-09 | Max-Delbrück-Centrum für Molekulare Medizin | An antibody that binds cd269 (bcma) suitable for use in the treatment of plasma cell diseases such as multiple myeloma and autoimmune diseases |
| TWI609887B (zh) | 2012-11-05 | 2018-01-01 | 皮爾法伯製藥公司 | 新穎的抗原結合蛋白及其作爲治療癌症之定址產物的用途 |
| CA2884431A1 (en) | 2012-11-08 | 2014-05-15 | F. Hoffmann-La Roche Ag | Her3 antigen binding proteins binding to the beta-hairpin of her3 |
| US20140128326A1 (en) | 2012-11-08 | 2014-05-08 | Novozymes Biopharma Dk A/S | Albumin variants |
| CN104968367B (zh) | 2012-11-13 | 2018-04-13 | 弗·哈夫曼-拉罗切有限公司 | 抗血凝素抗体和使用方法 |
| WO2014080251A1 (en) | 2012-11-24 | 2014-05-30 | Hangzhou Dac Biotech Co., Ltd. | Hydrophilic linkers and their uses for conjugation of drugs to cell binding molecules |
| US20140154255A1 (en) | 2012-11-30 | 2014-06-05 | Abbvie Biotherapeutics Inc. | Anti-vegf antibodies and their uses |
| JP6334553B2 (ja) | 2012-12-10 | 2018-05-30 | メルサナ セラピューティクス，インコーポレイティド | タンパク質−高分子−薬剤コンジュゲート |
| WO2014093640A1 (en) | 2012-12-12 | 2014-06-19 | Mersana Therapeutics,Inc. | Hydroxy-polmer-drug-protein conjugates |
| WO2014107739A1 (en) | 2013-01-07 | 2014-07-10 | Eleven Biotherapeutics, Inc. | Antibodies against pcsk9 |
| US10487155B2 (en) | 2013-01-14 | 2019-11-26 | Xencor, Inc. | Heterodimeric proteins |
| US9701759B2 (en) | 2013-01-14 | 2017-07-11 | Xencor, Inc. | Heterodimeric proteins |
| US10131710B2 (en) | 2013-01-14 | 2018-11-20 | Xencor, Inc. | Optimized antibody variable regions |
| US10738132B2 (en) | 2013-01-14 | 2020-08-11 | Xencor, Inc. | Heterodimeric proteins |
| US10968276B2 (en) | 2013-03-12 | 2021-04-06 | Xencor, Inc. | Optimized anti-CD3 variable regions |
| US9605084B2 (en) | 2013-03-15 | 2017-03-28 | Xencor, Inc. | Heterodimeric proteins |
| US11053316B2 (en) | 2013-01-14 | 2021-07-06 | Xencor, Inc. | Optimized antibody variable regions |
| WO2014113510A1 (en) | 2013-01-15 | 2014-07-24 | Xencor, Inc. | Rapid clearance of antigen complexes using novel antibodies |
| CA2900097A1 (en) | 2013-02-22 | 2014-08-28 | F. Hoffmann-La Roche Ag | Methods of treating cancer and preventing drug resistance |
| EP2961772A1 (en) | 2013-02-26 | 2016-01-06 | Roche Glycart AG | Anti-mcsp antibodies |
| KR20150123250A (ko) | 2013-03-06 | 2015-11-03 | 제넨테크, 인크. | 암 약물 내성의 치료 및 예방 방법 |
| JP6436965B2 (ja) | 2013-03-14 | 2018-12-12 | ジェネンテック， インコーポレイテッド | 抗ｂ７−ｈ４抗体及びイムノコンジュゲート |
| RU2015139054A (ru) | 2013-03-14 | 2017-04-19 | Дженентек, Инк. | Способы лечения рака и профилактики лекарственной резистентности рака |
| US9562099B2 (en) | 2013-03-14 | 2017-02-07 | Genentech, Inc. | Anti-B7-H4 antibodies and immunoconjugates |
| SG10201706210WA (en) | 2013-03-15 | 2017-09-28 | Genentech Inc | Compositions and methods for diagnosis and treatment of hepatic cancers |
| EP3424530A1 (en) | 2013-03-15 | 2019-01-09 | Zyngenia, Inc. | Multivalent and monovalent multispecific complexes and their uses |
| CN105377889B (zh) | 2013-03-15 | 2020-07-17 | Xencor股份有限公司 | 异二聚体蛋白 |
| US10106624B2 (en) | 2013-03-15 | 2018-10-23 | Xencor, Inc. | Heterodimeric proteins |
| CN105377892A (zh) | 2013-03-15 | 2016-03-02 | 艾伯维生物技术有限公司 | 抗cd25抗体及其用途 |
| US10858417B2 (en) | 2013-03-15 | 2020-12-08 | Xencor, Inc. | Heterodimeric proteins |
| AU2014233528B2 (en) | 2013-03-15 | 2019-02-28 | Abbvie Biotherapeutics Inc. | Fc variants |
| EP2970471A2 (en) | 2013-03-15 | 2016-01-20 | F. Hoffmann-La Roche AG | Anti-crth2 antibodies and their use |
| US10519242B2 (en) | 2013-03-15 | 2019-12-31 | Xencor, Inc. | Targeting regulatory T cells with heterodimeric proteins |
| EP3421495A3 (en) | 2013-03-15 | 2019-05-15 | Xencor, Inc. | Modulation of t cells with bispecific antibodies and fc fusions |
| NZ712314A (en) | 2013-03-15 | 2021-07-30 | Genentech Inc | Biomarkers and methods of treating pd-1 and pd-l1 related conditions |
| US9598485B2 (en) | 2013-03-15 | 2017-03-21 | Ac Immune S.A. | Anti-tau antibodies and methods of use |
| WO2014144935A2 (en) | 2013-03-15 | 2014-09-18 | Abbvie Biotherapeutics Inc. | Anti-cd25 antibodies and their uses |
| CA2905123A1 (en) | 2013-03-15 | 2014-09-18 | Genentech, Inc. | Methods of treating cancer and preventing cancer drug resistance |
| AR095882A1 (es) | 2013-04-22 | 2015-11-18 | Hoffmann La Roche | Terapia de combinación de anticuerpos contra csf-1r humano con un agonista de tlr9 |
| JP6618893B2 (ja) | 2013-04-29 | 2019-12-11 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｆｃ受容体結合が変更された非対称抗体および使用方法 |
| WO2014179657A1 (en) | 2013-05-03 | 2014-11-06 | Eleven Biotherapeutics, Inc. | Albumin variants binding to fcrn |
| PE20151926A1 (es) | 2013-05-20 | 2016-01-07 | Genentech Inc | Anticuerpos de receptores de antitransferrina y metodos de uso |
| EP3013365B1 (en) | 2013-06-26 | 2019-06-05 | Academia Sinica | Rm2 antigens and use thereof |
| EP3013347B1 (en) | 2013-06-27 | 2019-12-11 | Academia Sinica | Glycan conjugates and use thereof |
| WO2015010100A2 (en) | 2013-07-18 | 2015-01-22 | Fabrus, Inc. | Humanized antibodies with ultralong complementarity determining regions |
| US20160168231A1 (en) | 2013-07-18 | 2016-06-16 | Fabrus, Inc. | Antibodies with ultralong complementarity determining regions |
| JP6510518B2 (ja) | 2013-08-01 | 2019-05-08 | アジェンシス，インコーポレイテッド | Ｃｄ３７タンパク質に結合する抗体薬物結合体（ａｄｃ） |
| WO2015035044A2 (en) | 2013-09-04 | 2015-03-12 | Abbvie Biotherapeutics Inc. | Fc VARIANTS WITH IMPROVED ANTIBODY-DEPENDENT CELL-MEDIATED CYTOTOXICITY |
| CN105682666B (zh) | 2013-09-06 | 2021-06-01 | 中央研究院 | 使用醣脂激活人类iNKT细胞 |
| AR097584A1 (es) | 2013-09-12 | 2016-03-23 | Hoffmann La Roche | Terapia de combinación de anticuerpos contra el csf-1r humano y anticuerpos contra el pd-l1 humano |
| CN105518027A (zh) | 2013-09-17 | 2016-04-20 | 豪夫迈·罗氏有限公司 | 使用抗lgr5抗体的方法 |
| MX2016004579A (es) | 2013-10-10 | 2016-12-09 | Beth Israel Deaconess Medical Ct Inc | Proteinas de union del miembro 1 de la familia de transmembrana 4 l-seis (tm4sf1) y metodos de uso de las mismas. |
| PT3055331T (pt) | 2013-10-11 | 2021-04-05 | Oxford Bio Therapeutics Ltd | Anticorpos conjugados contra ly75 para o tratamento de cancro |
| KR102087850B1 (ko) | 2013-10-11 | 2020-03-12 | 메르사나 테라퓨틱스, 인코포레이티드 | 단백질-고분자-약물 접합체 |
| AU2014331645C1 (en) | 2013-10-11 | 2020-06-11 | Asana Biosciences, Llc | Protein-polymer-drug conjugates |
| CN105744954B (zh) | 2013-10-18 | 2021-03-05 | 豪夫迈·罗氏有限公司 | 抗rspo2和/或抗rspo3抗体及其用途 |
| AU2014342610A1 (en) | 2013-11-04 | 2016-06-02 | Abbvie Stemcentrx Llc | Anti-EFNA4 antibody-drug conjugates |
| SI3066074T1 (sl) * | 2013-11-04 | 2020-03-31 | Pfizer Inc. | Intermediati in postopki za sintetizacijo derivatov kaliheamicina |
| PE20160712A1 (es) | 2013-12-13 | 2016-07-26 | Genentech Inc | Anticuerpos e inmunoconjugados anti-cd33 |
| EA201691023A1 (ru) | 2013-12-16 | 2016-10-31 | Дженентек, Инк. | Пептидомиметические соединения и их конъюгаты антитела с лекарственным средством |
| EP3087182B1 (en) | 2013-12-23 | 2019-03-20 | Memorial Sloan-Kettering Cancer Center | Methods and compositions for treating cancer using peptide nucleic acid-based agents |
| TWI670283B (zh) | 2013-12-23 | 2019-09-01 | 美商建南德克公司 | 抗體及使用方法 |
| BR112016014945A2 (pt) | 2014-01-03 | 2018-01-23 | F. Hoffmann-La Roche Ag | conjugado, formulação farmacêutica e uso |
| CA2933384A1 (en) | 2014-01-03 | 2015-07-09 | F. Hoffmann-La Roche Ag | Bispecific anti-hapten/anti-blood brain barrier receptor antibodies, complexes thereof and their use as blood brain barrier shuttles |
| CA2930154A1 (en) | 2014-01-03 | 2015-07-09 | F. Hoffmann-La Roche Ag | Covalently linked helicar-anti-helicar antibody conjugates and uses thereof |
| US10150818B2 (en) | 2014-01-16 | 2018-12-11 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| WO2015109180A2 (en) | 2014-01-16 | 2015-07-23 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| CA2935393A1 (en) | 2014-01-24 | 2015-07-30 | Genentech, Inc. | Methods of using anti-steap1 antibodies and immunoconjugates |
| WO2015113476A1 (zh) | 2014-01-29 | 2015-08-06 | 上海恒瑞医药有限公司 | 配体-细胞毒性药物偶联物、其制备方法及其应用 |
| CA2937539A1 (en) | 2014-02-04 | 2015-08-13 | Genentech, Inc. | Mutant smoothened and methods of using the same |
| EP3825332A1 (en) | 2014-02-12 | 2021-05-26 | F. Hoffmann-La Roche AG | Anti-jagged1 antibodies and methods of use |
| KR20160124165A (ko) | 2014-02-21 | 2016-10-26 | 제넨테크, 인크. | 항-il-13/il-17 이중특이적 항체 및 그의 용도 |
| ES2960619T3 (es) | 2014-02-28 | 2024-03-05 | Hangzhou Dac Biotech Co Ltd | Enlazadores cargados y sus usos para la conjugación |
| JP6644717B2 (ja) | 2014-03-14 | 2020-02-12 | ジェネンテック， インコーポレイテッド | 異種ポリペプチドを分泌させるための方法及び組成物 |
| KR20160138177A (ko) | 2014-03-21 | 2016-12-02 | 애브비 인코포레이티드 | 항-ｅｇｆｒ 항체 및 항체 약물 접합체 |
| JP2017516458A (ja) | 2014-03-24 | 2017-06-22 | ジェネンテック， インコーポレイテッド | ｃ−ｍｅｔ拮抗剤による癌治療及びｃ−ｍｅｔ拮抗剤のＨＧＦ発現との相関 |
| TWI797430B (zh) | 2014-03-27 | 2023-04-01 | 中央研究院 | 反應性標記化合物及其用途 |
| BR112016022385A2 (pt) | 2014-03-28 | 2018-06-19 | Xencor, Inc | anticorpos específicos que se ligam a cd38 e cd3 |
| EP3126386A1 (en) | 2014-03-31 | 2017-02-08 | F. Hoffmann-La Roche AG | Combination therapy comprising anti-angiogenesis agents and ox40 binding agonists |
| PE20161571A1 (es) | 2014-03-31 | 2017-02-07 | Genentech Inc | Anticuerpos anti-ox40 y metodos de uso |
| BR112016022910A2 (pt) | 2014-04-11 | 2017-10-17 | Medimmune Llc | anticorpos contra her2 biespecíficos |
| MA53069B1 (fr) | 2014-04-25 | 2022-04-29 | Pf Medicament | Anticorps igf-1r et son utilisation comme véhicule d'adressage pour le traitement du cancer |
| PL3137114T3 (pl) | 2014-04-30 | 2021-06-28 | Pfizer Inc. | Koniugaty przeciwciało anty-ptk7-lek |
| CN106471117A (zh) | 2014-05-06 | 2017-03-01 | 豪夫迈·罗氏有限公司 | 使用哺乳动物细胞产生异多聚体蛋白 |
| CN106414499A (zh) | 2014-05-22 | 2017-02-15 | 基因泰克公司 | 抗gpc3抗体和免疫偶联物 |
| WO2015179835A2 (en) | 2014-05-23 | 2015-11-26 | Genentech, Inc. | Mit biomarkers and methods using the same |
| KR102576850B1 (ko) | 2014-05-27 | 2023-09-11 | 아카데미아 시니카 | 박테로이드 기원의 푸코시다제 및 이의 사용 방법 |
| US10118969B2 (en) | 2014-05-27 | 2018-11-06 | Academia Sinica | Compositions and methods relating to universal glycoforms for enhanced antibody efficacy |
| JP7062361B2 (ja) | 2014-05-27 | 2022-05-06 | アカデミア シニカ | 抗ｈｅｒ２糖操作抗体群およびその使用 |
| CA2950415A1 (en) | 2014-05-27 | 2015-12-03 | Academia Sinica | Anti-cd20 glycoantibodies and uses thereof |
| KR102494193B1 (ko) | 2014-05-28 | 2023-01-31 | 아카데미아 시니카 | 항-ｔｎｆ-알파 글리코항체 및 이의 용도 |
| US20230190750A1 (en) | 2014-06-13 | 2023-06-22 | Genentech, Inc. | Methods of treating and preventing cancer drug resistance |
| BR112016029935A2 (pt) | 2014-06-26 | 2017-10-31 | Hoffmann La Roche | ?anticorpos anti-brdu, complexo, formulação farmacêutica e uso de anticorpo? |
| JP2017526641A (ja) | 2014-07-11 | 2017-09-14 | ジェネンテック， インコーポレイテッド | Ｎｏｔｃｈ経路阻害 |
| US20160060360A1 (en) | 2014-07-24 | 2016-03-03 | Xencor, Inc. | Rapid clearance of antigen complexes using novel antibodies |
| TWI805109B (zh) | 2014-08-28 | 2023-06-11 | 美商奇諾治療有限公司 | 對cd19具專一性之抗體及嵌合抗原受體 |
| CA2959141A1 (en) | 2014-08-28 | 2016-03-03 | Bioatla, Llc | Conditionally active chimeric antigen receptors for modified t-cells |
| JP6899321B2 (ja) | 2014-09-08 | 2021-07-07 | アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ | 糖脂質を使用するヒトｉＮＫＴ細胞活性化 |
| PT3191135T (pt) | 2014-09-12 | 2020-11-12 | Genentech Inc | Anticorpos anti-her2 e imunoconjugados |
| KR20170052600A (ko) | 2014-09-12 | 2017-05-12 | 제넨테크, 인크. | 시스테인 가공된 항체 및 콘주게이트 |
| AR101846A1 (es) | 2014-09-12 | 2017-01-18 | Genentech Inc | Anticuerpos anti-cll-1 e inmunoconjugados |
| EP3191518B1 (en) | 2014-09-12 | 2020-01-15 | Genentech, Inc. | Anti-b7-h4 antibodies and immunoconjugates |
| EP3689910A3 (en) | 2014-09-23 | 2020-12-02 | F. Hoffmann-La Roche AG | Method of using anti-cd79b immunoconjugates |
| EP3200829B1 (en) | 2014-10-01 | 2023-12-06 | Medimmune, LLC | Method of conjugating a polypeptide |
| CN107074938A (zh) | 2014-10-16 | 2017-08-18 | 豪夫迈·罗氏有限公司 | 抗‑α‑突触核蛋白抗体和使用方法 |
| JP6723509B2 (ja) | 2014-10-24 | 2020-07-15 | 日油株式会社 | 環状ベンジリデンアセタールリンカーを有する抗体―薬物複合体 |
| JP2017537891A (ja) | 2014-10-31 | 2017-12-21 | ジェネンテック， インコーポレイテッド | 抗ｉｌ−１７ａ及びｉｌ−１７ｆ交差反応性抗体変異体、ならびにそれらを含む組成物、それらを作製する方法、及び使用する方法 |
| MX2017005751A (es) | 2014-11-03 | 2018-04-10 | Genentech Inc | Métodos y biomarcadores para predecir la eficacia y evaluación de un tratamiento con agonista de ox40. |
| SG11201703448QA (en) | 2014-11-03 | 2017-05-30 | Genentech Inc | Assays for detecting t cell immune subsets and methods of use thereof |
| CA2961439A1 (en) | 2014-11-05 | 2016-05-12 | Genentech, Inc. | Anti-fgfr2/3 antibodies and methods using same |
| ES2749383T3 (es) | 2014-11-06 | 2020-03-20 | Hoffmann La Roche | Variantes de la región Fc con unión al FcRn modificada y procedimientos de uso |
| WO2016073157A1 (en) | 2014-11-06 | 2016-05-12 | Genentech, Inc. | Anti-ang2 antibodies and methods of use thereof |
| EA201791029A1 (ru) | 2014-11-10 | 2017-12-29 | Дженентек, Инк. | Антитела против интерлейкина-33 и их применение |
| EP3221364B1 (en) | 2014-11-19 | 2020-12-16 | Genentech, Inc. | Antibodies against bace1 and use thereof for neural disease immunotherapy |
| EP3221361B1 (en) | 2014-11-19 | 2021-04-21 | Genentech, Inc. | Anti-transferrin receptor / anti-bace1 multispecific antibodies and methods of use |
| EP3221362B1 (en) | 2014-11-19 | 2019-07-24 | F.Hoffmann-La Roche Ag | Anti-transferrin receptor antibodies and methods of use |
| US10259887B2 (en) | 2014-11-26 | 2019-04-16 | Xencor, Inc. | Heterodimeric antibodies that bind CD3 and tumor antigens |
| CN110894240B (zh) | 2014-11-26 | 2022-04-15 | 森科股份有限公司 | 结合cd3和肿瘤抗原的异二聚体抗体 |
| AU2015353416C1 (en) | 2014-11-26 | 2022-01-27 | Xencor, Inc. | Heterodimeric antibodies that bind CD3 and CD38 |
| WO2016087416A1 (en) | 2014-12-03 | 2016-06-09 | F. Hoffmann-La Roche Ag | Multispecific antibodies |
| AR102918A1 (es) | 2014-12-05 | 2017-04-05 | Genentech Inc | Anticuerpos anti-cd79b y métodos de uso |
| MX2017007491A (es) | 2014-12-10 | 2018-05-04 | Genentech Inc | Anticuerpos del receptor de la barrera hematoencefálica y métodos para su uso. |
| MY183415A (en) | 2014-12-19 | 2021-02-18 | Chugai Pharmaceutical Co Ltd | Anti-c5 antibodies and methods of use |
| SG11201700841QA (en) | 2014-12-19 | 2017-03-30 | Chugai Pharmaceutical Co Ltd | Anti-myostatin antibodies, polypeptides containing variant fc regions, and methods of use |
| AU2015366284B2 (en) | 2014-12-19 | 2021-07-22 | Ablynx N.V. | Cysteine linked nanobody dimers |
| WO2016105450A2 (en) | 2014-12-22 | 2016-06-30 | Xencor, Inc. | Trispecific antibodies |
| US10495645B2 (en) | 2015-01-16 | 2019-12-03 | Academia Sinica | Cancer markers and methods of use thereof |
| US9975965B2 (en) | 2015-01-16 | 2018-05-22 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| AU2016206457B2 (en) | 2015-01-16 | 2021-11-11 | Juno Therapeutics, Inc. | Antibodies and chimeric antigen receptors specific for ROR1 |
| GB201501004D0 (en) | 2015-01-21 | 2015-03-04 | Cancer Rec Tech Ltd | Inhibitors |
| WO2016117346A1 (en) | 2015-01-22 | 2016-07-28 | Chugai Seiyaku Kabushiki Kaisha | A combination of two or more anti-c5 antibodies and methods of use |
| TWI736523B (zh) | 2015-01-24 | 2021-08-21 | 中央研究院 | 新穎聚醣結合物及其使用方法 |
| KR102630294B1 (ko) | 2015-01-24 | 2024-01-26 | 아카데미아 시니카 | 암 마커 및 이를 사용하는 방법 |
| CA2971288A1 (en) | 2015-02-02 | 2016-08-11 | The University Of Birmingham | Targeting moiety peptide epitope complexes having a plurality of t-cell epitopes |
| JP2018512597A (ja) | 2015-02-04 | 2018-05-17 | ジェネンテック， インコーポレイテッド | 突然変異体スムースンド及びその使用方法 |
| KR102605798B1 (ko) | 2015-02-05 | 2023-11-23 | 추가이 세이야쿠 가부시키가이샤 | 이온 농도 의존적 항원 결합 도메인을 포함하는 항체, Fc 영역 개변체, IL-8에 결합하는 항체, 및 그들의 사용 |
| WO2016141387A1 (en) | 2015-03-05 | 2016-09-09 | Xencor, Inc. | Modulation of t cells with bispecific antibodies and fc fusions |
| JP2018515457A (ja) * | 2015-04-21 | 2018-06-14 | アッヴィ・ステムセントルクス・エル・エル・シー | カリケアマイシン構築物および使用方法 |
| EP3913052A1 (en) | 2015-04-24 | 2021-11-24 | F. Hoffmann-La Roche AG | Methods of identifying bacteria comprising binding polypeptides |
| KR102668727B1 (ko) | 2015-04-24 | 2024-05-28 | 제넨테크, 인크. | 다중특이적 항원-결합 단백질 |
| JP2018520642A (ja) | 2015-05-01 | 2018-08-02 | ジェネンテック， インコーポレイテッド | マスク抗ｃｄ３抗体及びその使用方法 |
| EP3936524A3 (en) | 2015-05-11 | 2022-06-15 | F. Hoffmann-La Roche AG | Compositions and methods of treating lupus nephritis |
| LT3294770T (lt) | 2015-05-12 | 2020-12-28 | F. Hoffmann-La Roche Ag | Vėžio gydymo ir diagnostikos būdai |
| ES2789500T5 (es) | 2015-05-29 | 2023-09-20 | Hoffmann La Roche | Procedimientos terapéuticos y de diagnóstico para el cáncer |
| CN107771182A (zh) | 2015-05-29 | 2018-03-06 | 豪夫迈·罗氏有限公司 | 人源化抗埃博拉病毒糖蛋白抗体和使用方法 |
| MX2017014740A (es) | 2015-06-08 | 2018-08-15 | Genentech Inc | Métodos de tratamiento del cáncer con anticuerpos anti-ox40. |
| MX2017015937A (es) | 2015-06-08 | 2018-12-11 | Genentech Inc | Métodos de tratamiento del cáncer con anticuerpos anti-ox40 y antagonistas de unión al eje de pd-1. |
| AR105026A1 (es) | 2015-06-16 | 2017-08-30 | Genentech Inc | ANTICUERPOS MADURADOS POR AFINIDAD Y HUMANIZADOS PARA FcRH5 Y MÉTODOS PARA SU USO |
| US10501545B2 (en) | 2015-06-16 | 2019-12-10 | Genentech, Inc. | Anti-CLL-1 antibodies and methods of use |
| EP3916018A1 (en) | 2015-06-16 | 2021-12-01 | Genentech, Inc. | Anti-cd3 antibodies and methods of use |
| KR20180012859A (ko) | 2015-06-17 | 2018-02-06 | 제넨테크, 인크. | 항-her2 항체 및 이용 방법 |
| HUE057952T2 (hu) | 2015-06-24 | 2022-06-28 | Hoffmann La Roche | Anti-transzferrin receptor antitestek testreszabott affinitással |
| JP2018520153A (ja) | 2015-06-29 | 2018-07-26 | ジェネンテック， インコーポレイテッド | 臓器移植における使用のためのｉｉ型抗ｃｄ２０抗体 |
| CA2991973C (en) | 2015-07-12 | 2021-12-07 | Suzhou M-Conj Biotech Co., Ltd. | Bridge linkers for conjugation of a cell-binding molecule |
| US9839687B2 (en) | 2015-07-15 | 2017-12-12 | Suzhou M-Conj Biotech Co., Ltd. | Acetylenedicarboxyl linkers and their uses in specific conjugation of a cell-binding molecule |
| WO2017024146A1 (en) | 2015-08-05 | 2017-02-09 | Janssen Biotech, Inc. | Anti-cd154 antibodies and methods of using them |
| CN105384825B (zh) | 2015-08-11 | 2018-06-01 | 南京传奇生物科技有限公司 | 一种基于单域抗体的双特异性嵌合抗原受体及其应用 |
| BR112018003179A2 (pt) | 2015-08-20 | 2018-09-25 | Albumedix As | conjugados e variantes de albumina |
| JP6959912B2 (ja) | 2015-09-23 | 2021-11-05 | ジェネンテック， インコーポレイテッド | 抗ｖｅｇｆ抗体の最適化変異体 |
| MX2018003533A (es) | 2015-09-24 | 2019-04-25 | Abvitro Llc | Composiciones de anticuerpo de virus de inmunodeficiencia humana (vih) y metodos de uso. |
| TWI811892B (zh) | 2015-09-25 | 2023-08-11 | 美商建南德克公司 | 抗tigit抗體及使用方法 |
| CN108368510B (zh) | 2015-09-30 | 2023-09-01 | 詹森生物科技公司 | 特异性结合人cd40的激动性抗体和使用方法 |
| AR106189A1 (es) | 2015-10-02 | 2017-12-20 | Hoffmann La Roche | ANTICUERPOS BIESPECÍFICOS CONTRA EL A-b HUMANO Y EL RECEPTOR DE TRANSFERRINA HUMANO Y MÉTODOS DE USO |
| JP6657392B2 (ja) | 2015-10-02 | 2020-03-04 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | 二重特異性抗ヒトｃｄ２０／ヒトトランスフェリン受容体抗体及び使用方法 |
| UA124925C2 (en) | 2015-10-02 | 2021-12-15 | Hoffmann La Roche | Bispecific antibodies specific for pd1 and tim3 |
| SI3356404T1 (sl) | 2015-10-02 | 2021-11-30 | F. Hoffmann-La Roche Ag | Protitelesa proti PD1 in postopki uporabe |
| MA43354A (fr) | 2015-10-16 | 2018-08-22 | Genentech Inc | Conjugués médicamenteux à pont disulfure encombré |
| MA45326A (fr) | 2015-10-20 | 2018-08-29 | Genentech Inc | Conjugués calichéamicine-anticorps-médicament et procédés d'utilisation |
| EP3184547A1 (en) | 2015-10-29 | 2017-06-28 | F. Hoffmann-La Roche AG | Anti-tpbg antibodies and methods of use |
| PL3368579T3 (pl) | 2015-10-30 | 2022-03-21 | F. Hoffmann-La Roche Ag | Fragmenty przeciwciał ze zmodyfikowanymi regionami zawiasowymi i sposoby ich wytwarzania |
| SG11201803520PA (en) | 2015-11-03 | 2018-05-30 | Janssen Biotech Inc | Antibodies specifically binding pd-1 and their uses |
| WO2017079768A1 (en) | 2015-11-08 | 2017-05-11 | Genentech, Inc. | Methods of screening for multispecific antibodies |
| WO2017087789A1 (en) | 2015-11-19 | 2017-05-26 | Revitope Limited | Functional antibody fragment complementation for a two-components system for redirected killing of unwanted cells |
| PT3383920T (pt) | 2015-11-30 | 2024-04-15 | Univ California | Entrega de carga útil específica para tumores e ativação imune utilizando um anticorpo humano que tem como alvo um antigénio altamente específico da superfície das células tumorais |
| JP7058219B2 (ja) | 2015-12-07 | 2022-04-21 | ゼンコア インコーポレイテッド | Ｃｄ３及びｐｓｍａに結合するヘテロ二量体抗体 |
| EP3178848A1 (en) | 2015-12-09 | 2017-06-14 | F. Hoffmann-La Roche AG | Type ii anti-cd20 antibody for reducing formation of anti-drug antibodies |
| AU2016368469B2 (en) | 2015-12-09 | 2023-11-02 | F. Hoffmann-La Roche Ag | Type II anti-CD20 antibody for reducing formation of anti-drug antibodies |
| CA3005592C (en) | 2015-12-18 | 2024-01-23 | Chugai Seiyaku Kabushiki Kaisha | Anti-c5 antibodies and methods of use |
| AU2017212484C1 (en) | 2016-01-27 | 2020-11-05 | Medimmune, Llc | Methods for preparing antibodies with a defined glycosylation pattern |
| CA3019952A1 (en) | 2016-02-04 | 2017-08-10 | Curis, Inc. | Mutant smoothened and methods of using the same |
| DK3411076T3 (da) | 2016-02-05 | 2021-07-26 | Univ Copenhagen | Antistof-lægemiddelkonjugater målrettet mod UPARAP |
| WO2017151502A1 (en) | 2016-02-29 | 2017-09-08 | Genentech, Inc. | Therapeutic and diagnostic methods for cancer |
| US11340233B2 (en) | 2016-03-07 | 2022-05-24 | Pierre Fabre Medicament | Universal method to capture and analyze ADCs for characterization of drug distribution and the drug-to-antibody ratio in biological samples |
| JP2019515876A (ja) | 2016-03-08 | 2019-06-13 | アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ | Ｎ−グリカンおよびそのアレイのモジュール合成のための方法 |
| WO2017172907A1 (en) * | 2016-03-29 | 2017-10-05 | Sorrento Therapeutics, Inc. | Calicheamicin antibody drug conjugates linking an amidoacetyl group to a sugar moiety on calicheamicin |
| WO2017180864A1 (en) | 2016-04-14 | 2017-10-19 | Genentech, Inc. | Anti-rspo3 antibodies and methods of use |
| MX2018012433A (es) | 2016-04-15 | 2019-03-01 | Macrogenics Inc | Moleculas de union b7-h3 novedosas, conjugados anticuerpo-farmaco de los mismos y metodos de uso de los mismos. |
| KR20200087875A (ko) | 2016-04-15 | 2020-07-21 | 바이오아트라, 엘엘씨 | 항 Axl항체 및 이의 면역접합체와 이것들의 용도 |
| WO2017181111A2 (en) | 2016-04-15 | 2017-10-19 | Genentech, Inc. | Methods for monitoring and treating cancer |
| AU2017248766A1 (en) | 2016-04-15 | 2018-11-01 | Genentech, Inc. | Methods for monitoring and treating cancer |
| SG11201809620UA (en) | 2016-05-02 | 2018-11-29 | Hoffmann La Roche | The contorsbody - a single chain target binder |
| WO2017196847A1 (en) | 2016-05-10 | 2017-11-16 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Variable new antigen receptor (vnar) antibodies and antibody conjugates targeting tumor and viral antigens |
| CN109071640B (zh) | 2016-05-11 | 2022-10-18 | 豪夫迈·罗氏有限公司 | 经修饰抗生腱蛋白抗体及使用方法 |
| US11254742B2 (en) | 2016-05-13 | 2022-02-22 | Bioatla, Inc. | Anti-Ror2 antibodies, antibody fragments, their immunoconjugates and uses thereof |
| CN109313200B (zh) | 2016-05-27 | 2022-10-04 | 豪夫迈·罗氏有限公司 | 用于表征位点特异性抗体-药物缀合物的生物分析性方法 |
| US10668166B2 (en) | 2016-05-30 | 2020-06-02 | Toxinvent Ou | Antibody-drug-conjugates comprising novel anthracycline-derivatives for cancer treatment |
| EP3252078A1 (en) | 2016-06-02 | 2017-12-06 | F. Hoffmann-La Roche AG | Type ii anti-cd20 antibody and anti-cd20/cd3 bispecific antibody for treatment of cancer |
| CN110603266A (zh) | 2016-06-02 | 2019-12-20 | 豪夫迈·罗氏有限公司 | 用于治疗癌症的ii型抗cd20抗体和抗cd20/cd3双特异性抗体 |
| WO2017214182A1 (en) | 2016-06-07 | 2017-12-14 | The United States Of America. As Represented By The Secretary, Department Of Health & Human Services | Fully human antibody targeting pdi for cancer immunotherapy |
| CA3027045A1 (en) | 2016-06-08 | 2017-12-14 | Abbvie Inc. | Anti-b7-h3 antibodies and antibody drug conjugates |
| EP4371570A3 (en) | 2016-06-08 | 2024-07-17 | Xencor, Inc. | Treatment of igg4-related diseases with anti-cd19 antibodies crossbinding to cd32b |
| JP2019522643A (ja) | 2016-06-08 | 2019-08-15 | アッヴィ・インコーポレイテッド | 抗ｃｄ９８抗体及び抗体薬物コンジュゲート |
| AU2017277914A1 (en) | 2016-06-08 | 2019-01-03 | Abbvie Inc. | Anti-CD98 antibodies and antibody drug conjugates |
| CA3027103A1 (en) | 2016-06-08 | 2017-12-14 | Abbvie Inc. | Anti-b7-h3 antibodies and antibody drug conjugates |
| JP2019526529A (ja) | 2016-06-08 | 2019-09-19 | アッヴィ・インコーポレイテッド | 抗ｂ７−ｈ３抗体及び抗体薬物コンジュゲート |
| CA3026151A1 (en) | 2016-06-14 | 2017-12-21 | Xencor, Inc. | Bispecific checkpoint inhibitor antibodies |
| EP3474901A1 (en) | 2016-06-27 | 2019-05-01 | Tagworks Pharmaceuticals B.V. | Cleavable tetrazine used in bio-orthogonal drug activation |
| EP3475304B1 (en) | 2016-06-28 | 2022-03-23 | Xencor, Inc. | Heterodimeric antibodies that bind somatostatin receptor 2 |
| TWI823836B (zh) | 2016-07-08 | 2023-12-01 | 美商建南德克公司 | 人類副睪蛋白４（ｈｅ４）用於評定癌症治療反應性之用途 |
| MA45784A (fr) | 2016-07-29 | 2019-06-05 | Juno Therapeutics Inc | Anticorps anti-idiotypes dirigés contre anti-cd19 anticorps |
| CA3031559A1 (en) | 2016-08-02 | 2018-02-08 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Monoclonal antibodies targeting glypican-2 (gpc2) and use thereof |
| WO2018025168A1 (en) | 2016-08-03 | 2018-02-08 | Pfizer Inc. | Heteroaryl sulfone-based conjugation handles, methods for their preparation, and their use in synthesizing antibody drug conjugates |
| JP2019530434A (ja) | 2016-08-05 | 2019-10-24 | ジェネンテック， インコーポレイテッド | アゴニスト活性を有する多価及び多重エピトープ抗体ならびに使用方法 |
| MX2019001448A (es) | 2016-08-05 | 2019-09-13 | Chugai Pharmaceutical Co Ltd | Composicion para profilaxis o tratamiento de enfermedades relacionadas con interleucina 8 (il-8). |
| EP3500594A4 (en) | 2016-08-22 | 2020-03-11 | Cho Pharma Inc. | ANTIBODIES, BINDING FRAGMENTS AND METHOD FOR USE |
| EP3504239B1 (en) | 2016-08-25 | 2024-05-29 | F. Hoffmann-La Roche AG | Intermittent dosing of an anti-csf-1r antibody in combination with macrophage activating agent |
| US10793632B2 (en) | 2016-08-30 | 2020-10-06 | Xencor, Inc. | Bispecific immunomodulatory antibodies that bind costimulatory and checkpoint receptors |
| SG10201607778XA (en) | 2016-09-16 | 2018-04-27 | Chugai Pharmaceutical Co Ltd | Anti-Dengue Virus Antibodies, Polypeptides Containing Variant Fc Regions, And Methods Of Use |
| EP3515932B1 (en) | 2016-09-19 | 2023-11-22 | F. Hoffmann-La Roche AG | Complement factor based affinity chromatography |
| CA3038712A1 (en) | 2016-10-06 | 2018-04-12 | Genentech, Inc. | Therapeutic and diagnostic methods for cancer |
| PE20191034A1 (es) | 2016-10-14 | 2019-08-05 | Xencor Inc | Proteinas de fusion heterodimericas biespecificas que contienen proteinas de fusion fc il-15/il-15r y fragmentos de anticuerpo pd-1 |
| AU2017345454A1 (en) | 2016-10-19 | 2019-05-30 | Invenra Inc. | Antibody constructs |
| EP3532091A2 (en) | 2016-10-29 | 2019-09-04 | H. Hoffnabb-La Roche Ag | Anti-mic antibidies and methods of use |
| CN110099682B (zh) | 2016-11-14 | 2023-03-31 | 杭州多禧生物科技有限公司 | 偶联连接体，含有此连接体的细胞结合分子-药物偶联物及其制备和应用 |
| MX2019005438A (es) | 2016-11-15 | 2019-08-16 | Genentech Inc | Dosificacion para tratamiento con anticuerpos bispecificos anti-cd20 / anti-cd3. |
| TW201829463A (zh) | 2016-11-18 | 2018-08-16 | 瑞士商赫孚孟拉羅股份公司 | 抗hla-g抗體及其用途 |
| CA3036983A1 (en) | 2016-11-21 | 2018-05-24 | Cureab Gmbh | Anti-gp73 antibodies and immunoconjugates |
| US11135307B2 (en) | 2016-11-23 | 2021-10-05 | Mersana Therapeutics, Inc. | Peptide-containing linkers for antibody-drug conjugates |
| US11236171B2 (en) | 2016-12-21 | 2022-02-01 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Human monoclonal antibodies specific for FLT3 and uses thereof |
| EP3558360A1 (en) | 2016-12-22 | 2019-10-30 | F. Hoffmann-La Roche AG | Treatment of tumors with an anti-csf-1r antibody in combination with an anti-pd-l1 antibody after failure of anti-pd-l1/pd1 treatment |
| MX2019007019A (es) | 2016-12-22 | 2019-08-16 | Univ Degli Studi Magna Graecia Catanzaro | Anticuerpo monoclonal dirigido a un epitope de cd43 sialoglicosilado especifico asociado al cancer. |
| US11993625B2 (en) * | 2017-01-24 | 2024-05-28 | Pfizer, Inc. | Calicheamicin derivatives and antibody drug conjugates thereof |
| JP6995127B2 (ja) | 2017-02-10 | 2022-02-04 | ジェネンテック， インコーポレイテッド | 抗トリプターゼ抗体、その組成物、及びその使用 |
| AU2018228873A1 (en) | 2017-03-01 | 2019-08-29 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| EP3615572A1 (en) | 2017-04-27 | 2020-03-04 | Tesaro Inc. | Antibody agents directed against lymphocyte activation gene-3 (lag-3) and uses thereof |
| WO2018213064A1 (en) | 2017-05-19 | 2018-11-22 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Human monoclonal antibody targeting tnfer2 for cancer immunotherapy |
| AR111963A1 (es) | 2017-05-26 | 2019-09-04 | Univ California | Método y moléculas |
| TW201905037A (zh) | 2017-06-22 | 2019-02-01 | 美商梅爾莎納醫療公司 | 藥物攜帶聚合物支架及蛋白質聚合物藥物共軛物之製造方法 |
| CA3066953A1 (en) | 2017-06-30 | 2019-01-03 | Lentigen Technology, Inc. | Human monoclonal antibodies specific for cd33 and methods of their use |
| WO2019005208A1 (en) | 2017-06-30 | 2019-01-03 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | ANTIBODIES TO HUMAN MESOTHELIN AND USES IN ANTICANCER THERAPY |
| AU2018291497A1 (en) | 2017-06-30 | 2020-01-16 | Xencor, Inc. | Targeted heterodimeric Fc fusion proteins containing IL-15/IL-15Ra and antigen binding domains |
| US20190048073A1 (en) | 2017-07-20 | 2019-02-14 | Pfizer Inc. | Anti-gd3 antibodies and antibody-drug conjugates |
| MX2020000604A (es) | 2017-07-21 | 2020-09-10 | Genentech Inc | Métodos terapéuticos y de diagnóstico para el cáncer. |
| JP7232190B2 (ja) | 2017-10-20 | 2023-03-02 | 中外製薬株式会社 | 細胞への分子の取り込みを測定する方法 |
| EP3700540A4 (en) | 2017-10-24 | 2021-11-10 | Magenta Therapeutics, Inc. | COMPOSITIONS AND METHODS OF DEPRODUCTION FROM CD117 + CELLS |
| BR112020007736A2 (pt) | 2017-10-30 | 2020-10-20 | F. Hoffmann-La Roche Ag | composição e método de tratamento |
| WO2019086394A1 (en) | 2017-11-01 | 2019-05-09 | F. Hoffmann-La Roche Ag | The compbody - a multivalent target binder |
| WO2019089969A2 (en) | 2017-11-01 | 2019-05-09 | Juno Therapeutics, Inc. | Antibodies and chimeric antigen receptors specific for b-cell maturation antigen |
| AU2018358904A1 (en) | 2017-11-01 | 2020-04-16 | F. Hoffmann-La Roche Ag | TriFab-contorsbody |
| WO2019090263A1 (en) | 2017-11-06 | 2019-05-09 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| EP3706793A1 (en) | 2017-11-08 | 2020-09-16 | Xencor, Inc. | Bispecific and monospecific antibodies using novel anti-pd-1 sequences |
| US10981992B2 (en) | 2017-11-08 | 2021-04-20 | Xencor, Inc. | Bispecific immunomodulatory antibodies that bind costimulatory and checkpoint receptors |
| JP2021506291A (ja) | 2017-12-19 | 2021-02-22 | ゼンコア インコーポレイテッド | 改変されたｉｌ−２ ｆｃ融合タンパク質 |
| JP7314146B2 (ja) | 2017-12-28 | 2023-07-25 | 中外製薬株式会社 | 細胞傷害誘導治療剤 |
| WO2019143636A1 (en) | 2018-01-16 | 2019-07-25 | Lakepharma, Inc. | Bispecific antibody that binds cd3 and another target |
| AR115360A1 (es) | 2018-02-08 | 2021-01-13 | Genentech Inc | Moléculas de unión al antígeno y métodos de uso |
| WO2019165434A1 (en) | 2018-02-26 | 2019-08-29 | Genentech, Inc. | Dosing for treatment with anti-tigit and anti-pd-l1 antagonist antibodies |
| US20200040103A1 (en) | 2018-03-14 | 2020-02-06 | Genentech, Inc. | Anti-klk5 antibodies and methods of use |
| MX2020009472A (es) | 2018-03-14 | 2020-12-07 | Us Health | Receptores de antigenos quimericos anti-cd33 y sus usos. |
| MX2020009296A (es) | 2018-03-15 | 2020-11-13 | Chugai Pharmaceutical Co Ltd | Anticuerpos anti-virus del dengue que tienen reactividad cruzada con el virus zika y metodos de uso. |
| WO2019192432A1 (zh) | 2018-04-02 | 2019-10-10 | 上海博威生物医药有限公司 | 结合淋巴细胞活化基因-3(lag-3)的抗体及其用途 |
| CA3096052A1 (en) | 2018-04-04 | 2019-10-10 | Xencor, Inc. | Heterodimeric antibodies that bind fibroblast activation protein |
| TW202011029A (zh) | 2018-04-04 | 2020-03-16 | 美商建南德克公司 | 偵測及定量fgf21之方法 |
| CA3097741A1 (en) | 2018-04-18 | 2019-10-24 | Xencor, Inc. | Tim-3 targeted heterodimeric fusion proteins containing il-15/il-15ra fc-fusion proteins and tim-3 antigen binding domains |
| AR114789A1 (es) | 2018-04-18 | 2020-10-14 | Hoffmann La Roche | Anticuerpos anti-hla-g y uso de los mismos |
| US11524991B2 (en) | 2018-04-18 | 2022-12-13 | Xencor, Inc. | PD-1 targeted heterodimeric fusion proteins containing IL-15/IL-15Ra Fc-fusion proteins and PD-1 antigen binding domains and uses thereof |
| AU2019262520A1 (en) | 2018-05-04 | 2021-01-14 | Tagworks Pharmaceuticals B.V. | Tetrazines for high click conjugation yield in vivo and high click release yield |
| ES2975330T3 (es) | 2018-05-04 | 2024-07-04 | Tagworks Pharmaceuticals B V | Compuestos que comprenden un enlazador para aumentar la estabilidad del trans-cicloocteno |
| WO2019222294A1 (en) | 2018-05-14 | 2019-11-21 | Werewolf Therapeutics, Inc. | Activatable cytokine polypeptides and methods of use thereof |
| CN113840832A (zh) | 2018-05-14 | 2021-12-24 | 狼人治疗公司 | 可活化白介素-2多肽及其使用方法 |
| JP7361727B2 (ja) | 2018-05-24 | 2023-10-16 | ヤンセン バイオテツク，インコーポレーテツド | Ｐｓｍａ結合剤及びその使用 |
| CN113227127A (zh) | 2018-06-05 | 2021-08-06 | 伦敦大学国王学院 | 向胃肠系统递送酬载的btnl3/8导引构建体 |
| MA53094A (fr) | 2018-07-02 | 2021-05-12 | Amgen Inc | Protéine de liaison à l'antigène anti-steap1 |
| US11939377B2 (en) | 2018-07-12 | 2024-03-26 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Affinity matured CD22-specific monoclonal antibody and uses thereof |
| CN112739340A (zh) | 2018-07-23 | 2021-04-30 | 美真达治疗公司 | 抗cd5抗体药物缀合物(adc)在同种异体细胞疗法中的用途 |
| EP3833684A1 (en) | 2018-08-08 | 2021-06-16 | The United States of America, as represented by the Secretary, Department of Health and Human Services | High affinity monoclonal antibodies targeting glypican-2 and uses thereof |
| BR112021002037A2 (pt) | 2018-08-10 | 2021-05-04 | Chugai Seiyaku Kabushiki Kaisha | molécula de ligação de antígeno anti-cd137 e uso da mesma |
| US12097219B2 (en) | 2018-09-10 | 2024-09-24 | Legend Biotech Ireland Limited | Single-domain antibodies against CLL1 and constructs thereof |
| EP3849565A4 (en) | 2018-09-12 | 2022-12-28 | Fred Hutchinson Cancer Research Center | REDUCING CD33 EXPRESSION FOR SELECTIVE PROTECTION OF THERAPEUTIC CELLS |
| JP2022501332A (ja) | 2018-09-19 | 2022-01-06 | ジェネンテック， インコーポレイテッド | 膀胱がんの治療方法および診断方法 |
| BR112021004656A2 (pt) | 2018-09-26 | 2021-06-01 | Jiangsu Hengrui Medicine Co., Ltd. | conjugado fármaco-ligante de análogo exatecano, método para preparar o mesmo e aplicação do mesmo |
| BR112021005907A2 (pt) | 2018-09-27 | 2021-08-10 | Xilio Development, Inc. | citocinas mascaradas, ácido nucleico, vetor, célula hospedeira, métodos para produzir uma citocina mascarada, para tratar ou prevenir uma doença neoplásica e para tratar ou prevenir uma doença inflamatória ou autoimune neoplásica, composição, composição farmacêutica e kit |
| SG11202103192RA (en) | 2018-10-03 | 2021-04-29 | Xencor Inc | Il-12 heterodimeric fc-fusion proteins |
| CN113196061A (zh) | 2018-10-18 | 2021-07-30 | 豪夫迈·罗氏有限公司 | 肉瘤样肾癌的诊断和治疗方法 |
| EP3873534A1 (en) | 2018-10-29 | 2021-09-08 | Mersana Therapeutics, Inc. | Cysteine engineered antibody-drug conjugates with peptide-containing linkers |
| MX2021005398A (es) | 2018-11-07 | 2021-07-06 | Crispr Therapeutics Ag | Terapia del cancer con celulas inmunitarias anti-cd33. |
| MX2021005808A (es) | 2018-11-20 | 2021-07-02 | Univ Cornell | Complejos macrociclicos de radionucleidos alfa-emisores y su uso en radioterapia focalizada de cancer. |
| AU2018451747A1 (en) | 2018-12-06 | 2021-06-17 | F. Hoffmann-La Roche Ag | Combination therapy of diffuse large B-cell lymphoma comprising an anti-CD79b immunoconjugates, an alkylating agent and an anti-CD20 antibody |
| WO2020127968A1 (en) | 2018-12-20 | 2020-06-25 | Marino Stephen F | Protein-drug conjugate comprising a monomeric form of proteinase 3 |
| JP2022514290A (ja) | 2018-12-20 | 2022-02-10 | ジェネンテック， インコーポレイテッド | 改変抗体ｆｃおよび使用方法 |
| US20220064301A1 (en) | 2018-12-26 | 2022-03-03 | Xilio Development, Inc. | Anti-ctla4 antibodies and methods of use thereof |
| CN113490510A (zh) | 2019-01-08 | 2021-10-08 | 美国政府(由卫生和人类服务部的部长所代表) | 用于治疗实体瘤的靶向间皮素的跨物种单结构域抗体 |
| EP3914291A2 (en) | 2019-01-22 | 2021-12-01 | F. Hoffmann-La Roche AG | Immunoglobulin a antibodies and methods of production and use |
| AU2020212534A1 (en) | 2019-01-22 | 2021-07-22 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | High affinity monoclonal antibodies targeting glypican-1 and methods of use |
| CN113329770A (zh) | 2019-01-24 | 2021-08-31 | 中外制药株式会社 | 新型癌抗原及所述抗原的抗体 |
| PE20212198A1 (es) | 2019-01-29 | 2021-11-16 | Juno Therapeutics Inc | Anticuerpos y receptores quimericos de antigenos especificos para receptor 1 huerfano tipo receptor tirosina-cinasa (ror1) |
| CA3130695A1 (en) | 2019-02-27 | 2020-09-03 | Genentech, Inc. | Dosing for treatment with anti-tigit and anti-cd20 or anti-cd38 antibodies |
| JP2022523946A (ja) | 2019-03-01 | 2022-04-27 | ゼンコア インコーポレイテッド | Ｅｎｐｐ３およびｃｄ３に結合するヘテロ二量体抗体 |
| EP3938403A1 (en) | 2019-03-14 | 2022-01-19 | F. Hoffmann-La Roche AG | Treatment of cancer with her2xcd3 bispecific antibodies in combination with anti-her2 mab |
| MX2021011320A (es) | 2019-03-19 | 2021-12-10 | Fundacio Privada Inst Dinvestigacio Oncològica De Vall Hebron | Terapia de combinacion con omomyc y un anticuerpo que se une a pd-1 o a ctla-4 para el tratamiento del cancer. |
| KR20220002967A (ko) | 2019-04-19 | 2022-01-07 | 제넨테크, 인크. | 항 mertk 항체 및 이의 사용 방법 |
| JP2022529985A (ja) | 2019-04-19 | 2022-06-27 | ヤンセン バイオテツク，インコーポレーテツド | 抗ｐｓｍａ／ｃｄ３抗体で前立腺癌を治療する方法 |
| EP3962527A4 (en) | 2019-04-30 | 2023-11-01 | Senti Biosciences, Inc. | CHIMERIC RECEPTORS AND THEIR METHODS OF USE |
| AU2020275415A1 (en) | 2019-05-14 | 2021-11-25 | Genentech, Inc. | Methods of using anti-CD79B immunoconjugates to treat follicular lymphoma |
| SG11202112541RA (en) | 2019-05-14 | 2021-12-30 | Werewolf Therapeutics Inc | Separation moieties and methods and use thereof |
| AU2020275348A1 (en) | 2019-05-15 | 2021-12-09 | Chugai Seiyaku Kabushiki Kaisha | An antigen-binding molecule, a pharmaceutical composition, and a method |
| CA3144535A1 (en) | 2019-06-03 | 2020-12-10 | The University Of Chicago | Methods and compositions for treating cancer with collagen binding drug carriers |
| EP3983406A4 (en) * | 2019-06-12 | 2023-09-06 | Ontario Institute for Cancer Research (OICR) | HETEROCYCLOALKYL AND UNSATURATED HETEROAROMATIC ACYLHYDRAZONE LINKERS, RELATED METHODS AND USES |
| IL289094A (en) | 2019-06-17 | 2022-02-01 | Tagworks Pharmaceuticals B V | Tetrazines for increasing the speed and yield of the "click release" reaction |
| AU2020297253B2 (en) | 2019-06-17 | 2024-05-23 | Tagworks Pharmaceuticals B.V. | Compounds for fast and efficient click release |
| MX2022000111A (es) | 2019-07-10 | 2022-02-10 | Chugai Pharmaceutical Co Ltd | Moleculas de union a claudina-6 y usos de las mismas. |
| US20220267452A1 (en) | 2019-07-12 | 2022-08-25 | Chugai Seiyaku Kabushiki Kaisha | Anti-mutation type fgfr3 antibody and use therefor |
| JP2022544289A (ja) | 2019-08-14 | 2022-10-17 | コディアック バイオサイエンシーズ， インコーポレイテッド | Ｓｔａｔ６を標的とする細胞外小胞－ａｓｏ構築物 |
| EP4013878A1 (en) | 2019-08-14 | 2022-06-22 | Codiak BioSciences, Inc. | Extracellular vesicle-aso constructs targeting cebp/beta |
| WO2021030769A1 (en) | 2019-08-14 | 2021-02-18 | Codiak Biosciences, Inc. | Extracellular vesicles with nras antisense oligonucleotides |
| CA3147365A1 (en) | 2019-08-14 | 2021-02-18 | Joanne LIM | Extracellular vesicle-nlrp3 antagonist |
| KR20220088847A (ko) | 2019-09-04 | 2022-06-28 | 주식회사 와이바이오로직스 | 항-vsig4 항체 또는 항원-결합 단편 및 이들의 용도 |
| MX2022003610A (es) | 2019-09-27 | 2022-04-20 | Genentech Inc | Administracion de dosis para tratamiento con anticuerpos antagonistas anti-tigit y anti-pd-l1. |
| AU2020357550A1 (en) | 2019-10-04 | 2022-05-05 | Tae Life Sciences, Llc | Antibody compositions comprising Fc mutations and site-specific conjugation properties |
| MX2022004443A (es) | 2019-10-18 | 2022-05-02 | Genentech Inc | Metodos para usar inmunoconjugados anti-cd79b para tratar linfoma difuso de linfocitos b grandes. |
| JP2022552875A (ja) | 2019-10-22 | 2022-12-20 | ザ ユナイテッド ステイツ オブ アメリカ， アズ リプレゼンテッド バイ ザ セクレタリー， デパートメント オブ ヘルス アンド ヒューマン サービシーズ | 多様な固形腫瘍を処置するためのｂ７ｈ３（ｃｄ２７６）を標的とする高親和性ナノボディ |
| WO2021092171A1 (en) | 2019-11-06 | 2021-05-14 | Genentech, Inc. | Diagnostic and therapeutic methods for treatment of hematologic cancers |
| KR20220101147A (ko) | 2019-11-14 | 2022-07-19 | 웨어울프 세라퓨틱스, 인크. | 활성화가능한 사이토카인 폴리펩티드 및 이의 사용 방법 |
| CN116670268A (zh) | 2019-11-22 | 2023-08-29 | 免疫医疗有限公司 | 包含e2泛素或泛素样缀合结构域和用于特异性蛋白质降解的靶向结构域的融合蛋白 |
| JP2023504736A (ja) | 2019-12-06 | 2023-02-06 | ジュノー セラピューティクス インコーポレイテッド | Ｇｐｒｃ５ｄ標的結合ドメインに対する抗イディオタイプ抗体ならびに関連する組成物および方法 |
| JP2023504740A (ja) | 2019-12-06 | 2023-02-06 | ジュノー セラピューティクス インコーポレイテッド | Ｂｃｍａ標的結合ドメインに対する抗イディオタイプ抗体ならびに関連する組成物および方法 |
| CA3161573A1 (en) | 2019-12-12 | 2021-06-17 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Antibody-drug conjugates specific for cd276 and uses thereof |
| TW202128767A (zh) | 2019-12-13 | 2021-08-01 | 美商建南德克公司 | 抗ly6g6d抗體及其使用方法 |
| IL294226A (en) | 2019-12-27 | 2022-08-01 | Chugai Pharmaceutical Co Ltd | Anti-ctla-4 antibodies and their use |
| CN110818795B (zh) | 2020-01-10 | 2020-04-24 | 上海复宏汉霖生物技术股份有限公司 | 抗tigit抗体和使用方法 |
| MX2022009044A (es) | 2020-01-22 | 2022-08-11 | Shanghai Senhui Medicine Co Ltd | Conjugado de farmaco de derivado de eribulin, metodo de preparacion y aplicacion del mismo en medicina. |
| WO2022050954A1 (en) | 2020-09-04 | 2022-03-10 | Genentech, Inc. | Dosing for treatment with anti-tigit and anti-pd-l1 antagonist antibodies |
| WO2021194481A1 (en) | 2020-03-24 | 2021-09-30 | Genentech, Inc. | Dosing for treatment with anti-tigit and anti-pd-l1 antagonist antibodies |
| TW202144395A (zh) | 2020-02-12 | 2021-12-01 | 日商中外製藥股份有限公司 | 用於癌症之治療的抗cd137抗原結合分子 |
| IL296256A (en) | 2020-03-13 | 2022-11-01 | Genentech Inc | Antibodies against interleukin-33 and uses thereof |
| KR20220156575A (ko) | 2020-03-19 | 2022-11-25 | 제넨테크, 인크. | 동종형 선택적 항-tgf-베타 항체 및 이용 방법 |
| AU2021243080A1 (en) | 2020-03-25 | 2022-09-22 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | Preparation method for antibody medicament conjugate |
| CN115103691A (zh) | 2020-03-25 | 2022-09-23 | 江苏恒瑞医药股份有限公司 | 一种含抗体药物偶联物的药物组合物及其用途 |
| EP4127724A1 (en) | 2020-04-03 | 2023-02-08 | Genentech, Inc. | Therapeutic and diagnostic methods for cancer |
| CN115916822A (zh) | 2020-04-24 | 2023-04-04 | 基因泰克公司 | 使用抗CD79b免疫缀合物的方法 |
| WO2021222167A1 (en) | 2020-04-28 | 2021-11-04 | Genentech, Inc. | Methods and compositions for non-small cell lung cancer immunotherapy |
| WO2021231976A1 (en) | 2020-05-14 | 2021-11-18 | Xencor, Inc. | Heterodimeric antibodies that bind prostate specific membrane antigen (psma) and cd3 |
| US20230220068A1 (en) | 2020-06-05 | 2023-07-13 | Codiak Biosciences, Inc. | Anti-transferrin extracellular vesicles |
| MX2022015651A (es) | 2020-06-11 | 2023-01-16 | Genentech Inc | Conjugados de nanolipoproteina-polipeptido y composiciones, sistemas y procedimientos mediante el uso de los mismos. |
| JP2023529206A (ja) | 2020-06-12 | 2023-07-07 | ジェネンテック， インコーポレイテッド | がん免疫療法のための方法及び組成物 |
| TW202200616A (zh) | 2020-06-18 | 2022-01-01 | 美商建南德克公司 | 使用抗tigit抗體及pd-1軸結合拮抗劑之治療 |
| CN115812149A (zh) | 2020-07-13 | 2023-03-17 | 基因泰克公司 | 用于预测多肽免疫原性的基于细胞的方法 |
| WO2022025184A1 (ja) | 2020-07-29 | 2022-02-03 | 中外製薬株式会社 | 非放射性物質で標識した薬剤の薬物動態を測定する方法 |
| KR20230095918A (ko) | 2020-08-05 | 2023-06-29 | 주노 쎄러퓨티크스 인코퍼레이티드 | Ror1-표적 결합 도메인에 대한 항이디오타입 항체 및 관련 조성물 및 방법 |
| EP4192942A1 (en) | 2020-08-07 | 2023-06-14 | Genentech, Inc. | T cell-based methods for predicting polypeptide immunogenicity |
| BR112023002123A2 (pt) | 2020-08-07 | 2023-03-07 | Genentech Inc | Proteína de fusão fc, ácidos nucleicos isolados, método de produção da proteína de fusão fc, formulação farmacêutica, métodos para expandir o número de células dendríticas (dcs) em um indivíduo e para tratar um câncer, proteína fc sem efetora e anticorpo |
| EP4210832A1 (en) | 2020-09-14 | 2023-07-19 | Vor Biopharma, Inc. | Chimeric antigen receptors for treatment of cancer |
| KR20230082632A (ko) | 2020-10-05 | 2023-06-08 | 제넨테크, 인크. | 항-fcrh5/항-cd3 이중특이성 항체를 사용한 치료를 위한 투약 |
| US20230391852A1 (en) | 2020-10-26 | 2023-12-07 | The U.S.A., As Represented By The Secretary, Department Of Health And Human Services | Single domain antibodies targeting sars coronavirus spike protein and uses thereof |
| CA3199623A1 (en) | 2020-10-27 | 2022-05-05 | Vor Biopharma Inc. | Compositions and methods for treating hematopoietic malignancy |
| KR20230100732A (ko) | 2020-11-04 | 2023-07-05 | 제넨테크, 인크. | 항-cd20/항-cd3 이중특이성 항체의 피하 투여 |
| CA3196539A1 (en) | 2020-11-04 | 2022-05-12 | Chi-Chung Li | Dosing for treatment with anti-cd20/anti-cd3 bispecific antibodies |
| KR20230095113A (ko) | 2020-11-04 | 2023-06-28 | 제넨테크, 인크. | 항-cd20/항-cd3 이중특이적 항체들과 항-cd79b 항체 약물 접합체들을 이용한 치료를 위한 투약 |
| UY39610A (es) | 2021-01-20 | 2022-08-31 | Abbvie Inc | Conjugados anticuerpo-fármaco anti-egfr |
| MX2023008909A (es) | 2021-01-28 | 2023-10-23 | Janssen Biotech Inc | Proteínas de unión a psma y usos de estas. |
| TW202317612A (zh) | 2021-03-01 | 2023-05-01 | 美商艾希利歐發展股份有限公司 | 用於治療癌症的ｃｔｌａ４及ｐｄ１／ｐｄｌ１抗體之組合 |
| CA3209364A1 (en) | 2021-03-01 | 2022-09-09 | Jennifer O'neil | Combination of masked ctla4 and pd1/pdl1 antibodies for treating cancer |
| WO2022184853A1 (en) | 2021-03-03 | 2022-09-09 | Pierre Fabre Medicament | Anti-vsig4 antibody or antigen binding fragment and uses thereof |
| AU2022232375A1 (en) | 2021-03-09 | 2023-09-21 | Xencor, Inc. | Heterodimeric antibodies that bind cd3 and cldn6 |
| KR20230154311A (ko) | 2021-03-10 | 2023-11-07 | 젠코어 인코포레이티드 | Cd3 및 gpc3에 결합하는 이종이량체 항체 |
| AR125344A1 (es) | 2021-04-15 | 2023-07-05 | Chugai Pharmaceutical Co Ltd | Anticuerpo anti-c1s |
| WO2022232612A1 (en) | 2021-04-29 | 2022-11-03 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Lassa virus-specific nanobodies and methods of their use |
| JP2024509664A (ja) | 2021-04-30 | 2024-03-05 | エフ・ホフマン－ラ・ロシュ・アクチェンゲゼルシャフト | 抗ｃｄ２０／抗ｃｄ３二重特異性抗体による治療のための投薬 |
| AU2021443318A1 (en) | 2021-04-30 | 2023-09-07 | F. Hoffmann-La Roche Ag | Dosing for combination treatment with anti-cd20/anti-cd3 bispecific antibody and anti-cd79b antibody drug conjugate |
| AU2022265543A1 (en) | 2021-04-30 | 2023-10-26 | Pierre Fabre Medicament | New stable anti-vista antibody |
| IL308351A (en) | 2021-05-12 | 2024-01-01 | Genentech Inc | Methods for using anti-CD79B immunoconjugates to treat diffuse large B-cell lymphoma |
| EP4342984A1 (en) | 2021-05-19 | 2024-03-27 | Chugai Seiyaku Kabushiki Kaisha | Method for predicting in vivo pharmacokinetics of molecule |
| WO2022248870A1 (en) | 2021-05-28 | 2022-12-01 | Glaxosmithkline Intellectual Property Development Limited | Combination therapies for treating cancer |
| CN117480184A (zh) | 2021-06-04 | 2024-01-30 | 中外制药株式会社 | 抗ddr2抗体及其用途 |
| CN117500831A (zh) | 2021-06-09 | 2024-02-02 | 美国政府(由卫生和人类服务部的部长所代表) | 用于治疗实体瘤的靶向pd-l1的跨物种单结构域抗体 |
| CA3221833A1 (en) | 2021-06-25 | 2022-12-29 | Chugai Seiyaku Kabushiki Kaisha | Anti-ctla-4 antibody |
| CA3220353A1 (en) | 2021-06-25 | 2022-12-29 | Chugai Seiyaku Kabushiki Kaisha | Use of anti-ctla-4 antibody |
| US11807685B2 (en) | 2021-08-05 | 2023-11-07 | The Uab Research Foundation | Anti-CD47 antibody and uses thereof |
| US20240336697A1 (en) | 2021-08-07 | 2024-10-10 | Genentech, Inc. | Methods of using anti-cd79b immunoconjugates to treat diffuse large b-cell lymphoma |
| AU2022327766A1 (en) | 2021-08-13 | 2023-12-14 | Ludwig-Maximilians-Universität München | Anti-csf1r car expressing lymphocytes for targeted tumor therapy |
| JP2024535712A (ja) | 2021-08-27 | 2024-10-02 | ヤンセン バイオテツク，インコーポレーテツド | 抗ｐｓｍａ抗体及びその使用 |
| WO2023031445A2 (en) | 2021-09-06 | 2023-03-09 | Veraxa Biotech Gmbh | Novel aminoacyl-trna synthetase variants for genetic code expansion in eukaryotes |
| TW202321308A (zh) | 2021-09-30 | 2023-06-01 | 美商建南德克公司 | 使用抗ｔｉｇｉｔ抗體、抗ｃｄ３８抗體及ｐｄ—１軸結合拮抗劑治療血液癌症的方法 |
| WO2023057893A1 (en) | 2021-10-05 | 2023-04-13 | Glaxosmithkline Intellectual Property Development Limited | Combination therapies for treating cancer |
| AR127269A1 (es) | 2021-10-08 | 2024-01-03 | Chugai Pharmaceutical Co Ltd | Formulación de anticuerpo anti-hla-dq2.5 |
| EP4186529A1 (en) | 2021-11-25 | 2023-05-31 | Veraxa Biotech GmbH | Improved antibody-payload conjugates (apcs) prepared by site-specific conjugation utilizing genetic code expansion |
| AU2022395626A1 (en) | 2021-11-25 | 2024-05-30 | Veraxa Biotech Gmbh | Improved antibody-payload conjugates (apcs) prepared by site-specific conjugation utilizing genetic code expansion |
| CA3239713A1 (en) | 2021-12-08 | 2023-06-15 | Edward A. LEMKE | Hydrophilic tetrazine-functionalized payloads for preparation of targeting conjugates |
| AU2022411573A1 (en) | 2021-12-17 | 2024-06-27 | Shanghai Henlius Biologics Co., Ltd. | Anti-ox40 antibodies and methods of use |
| EP4448578A1 (en) | 2021-12-17 | 2024-10-23 | Shanghai Henlius Biotech, Inc. | Anti-ox40 antibodies, multispecific antibodies and methods of use |
| KR20240130138A (ko) | 2022-01-07 | 2024-08-28 | 존슨 앤드 존슨 엔터프라이즈 이노베이션 인코포레이티드 | Il-1 베타 결합 단백질의 재료 및 방법 |
| AU2023221765B2 (en) | 2022-02-15 | 2024-09-19 | Tagworks Pharmaceuticals B.V. | Masked il12 protein |
| WO2023180353A1 (en) | 2022-03-23 | 2023-09-28 | F. Hoffmann-La Roche Ag | Combination treatment of an anti-cd20/anti-cd3 bispecific antibody and chemotherapy |
| WO2023179740A1 (en) | 2022-03-25 | 2023-09-28 | Shanghai Henlius Biotech , Inc. | Anti-msln antibodies and methods of use |
| AU2022450448A1 (en) | 2022-04-01 | 2024-10-10 | Genentech, Inc. | Dosing for treatment with anti-fcrh5/anti-cd3 bispecific antibodies |
| AR129062A1 (es) | 2022-04-13 | 2024-07-10 | Genentech Inc | Composiciones farmacéuticas de proteínas terapéuticas y métodos de uso |
| TW202404637A (zh) | 2022-04-13 | 2024-02-01 | 瑞士商赫孚孟拉羅股份公司 | 抗ｃｄ２０／抗ｃｄ３雙特異性抗體之醫藥組成物及使用方法 |
| WO2023215293A1 (en) | 2022-05-02 | 2023-11-09 | Athanor Biosciences, Inc. | Cancer eradicating – bio-nanoparticles (ce-bnp) |
| WO2023219613A1 (en) | 2022-05-11 | 2023-11-16 | Genentech, Inc. | Dosing for treatment with anti-fcrh5/anti-cd3 bispecific antibodies |
| WO2023240058A2 (en) | 2022-06-07 | 2023-12-14 | Genentech, Inc. | Prognostic and therapeutic methods for cancer |
| TW202417042A (zh) | 2022-07-13 | 2024-05-01 | 美商建南德克公司 | 用抗ｆｃｒｈ５／抗ｃｄ３雙特異性抗體進行治療之給藥 |
| WO2024020432A1 (en) | 2022-07-19 | 2024-01-25 | Genentech, Inc. | Dosing for treatment with anti-fcrh5/anti-cd3 bispecific antibodies |
| WO2024020564A1 (en) | 2022-07-22 | 2024-01-25 | Genentech, Inc. | Anti-steap1 antigen-binding molecules and uses thereof |
| WO2024049949A1 (en) | 2022-09-01 | 2024-03-07 | Genentech, Inc. | Therapeutic and diagnostic methods for bladder cancer |
| WO2024073751A1 (en) | 2022-09-29 | 2024-04-04 | Vor Biopharma Inc. | Methods and compositions for gene modification and enrichment |
| WO2024080872A1 (en) | 2022-10-12 | 2024-04-18 | Tagworks Pharmaceuticals B.V. | Strained bicyclononenes |
| WO2024089013A1 (en) | 2022-10-25 | 2024-05-02 | Peptomyc, S.L. | Combination therapy for the treatment of cancer |
| TW202426505A (zh) | 2022-10-25 | 2024-07-01 | 美商建南德克公司 | 癌症之治療及診斷方法 |
| WO2024102948A1 (en) | 2022-11-11 | 2024-05-16 | Celgene Corporation | Fc receptor-homolog 5 (fcrh5) specific binding molecules and bispecific t-cell engaging antibodies including same and related methods |
| US20240226298A1 (en) | 2022-12-13 | 2024-07-11 | Juno Therapeutics, Inc. | Chimeric antigen receptors specific for baff-r and cd19 and methods and uses thereof |
| GB202219154D0 (en) | 2022-12-19 | 2023-02-01 | Metacurum Biotech Ab | Antibodies and uses thereof |
| WO2024153789A1 (en) | 2023-01-20 | 2024-07-25 | Basf Se | Stabilized biopolymer composition, their manufacture and use |
| WO2024168312A1 (en) | 2023-02-09 | 2024-08-15 | Vor Biopharma Inc. | Methods for treating hematopoietic malignancy |
| WO2024191293A1 (en) | 2023-03-10 | 2024-09-19 | Tagworks Pharmaceuticals B.V. | Trans-cyclooctene with improved t-linker |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5053394A (en) * | 1988-09-21 | 1991-10-01 | American Cyanamid Company | Targeted forms of methyltrithio antitumor agents |
| EP0329184A3 (en) * | 1988-02-19 | 1990-05-23 | Neorx Corporation | Antimers and antimeric conjugation |
| US5006652A (en) * | 1988-08-08 | 1991-04-09 | Eli Lilly And Company | Intermediates for antibody-vinca drug conjugates |
| US5094849A (en) * | 1988-08-08 | 1992-03-10 | Eli Lilly And Company | Cytotoxic antibody conjugates of hydrazide derivatized vinca analogs via simple organic linkers |
| US5028697A (en) * | 1988-08-08 | 1991-07-02 | Eli Lilly And Company | Cytotoxic antibody conjugates of hydrazide derivatized methotrexate analogs via simple organic linkers |
| US5144012A (en) * | 1988-08-08 | 1992-09-01 | Eli Lilly And Company | Cytotoxic drug conjugates |
| US5045451A (en) * | 1988-10-26 | 1991-09-03 | Board Of Regents | Methods for screening antibodies for use as immunotoxins |
| IL115770A (en) * | 1989-04-14 | 1999-03-12 | American Cyanamid Co | Substituted disulfides of formula q-sp-ss-w their preparation and use for inhibiting the growth of tumours and for treating bacterial infections |
| GB8928874D0 (en) * | 1989-12-21 | 1990-02-28 | Celltech Ltd | Humanised antibodies |
| GB9120467D0 (en) * | 1991-09-26 | 1991-11-06 | Celltech Ltd | Anti-hmfg antibodies and process for their production |
| US5773001A (en) * | 1994-06-03 | 1998-06-30 | American Cyanamid Company | Conjugates of methyltrithio antitumor agents and intermediates for their synthesis |
-
1994
- 1994-06-03 US US08/253,877 patent/US5773001A/en not_active Expired - Lifetime
- 1994-10-12 TW TW083109420A patent/TW394778B/zh not_active IP Right Cessation
-
1995
- 1995-05-26 US US08/452,164 patent/US5877296A/en not_active Expired - Lifetime
- 1995-05-31 JP JP15564495A patent/JP3650165B2/ja not_active Expired - Lifetime
- 1995-06-01 EP EP95303746A patent/EP0689845B1/en not_active Expired - Lifetime
- 1995-06-01 AT AT95303746T patent/ATE223234T1/de active
- 1995-06-01 SI SI9530554T patent/SI0689845T1/xx unknown
- 1995-06-01 PT PT95303746T patent/PT689845E/pt unknown
- 1995-06-01 ES ES95303746T patent/ES2181752T3/es not_active Expired - Lifetime
- 1995-06-01 CA CA2150785A patent/CA2150785C/en not_active Expired - Lifetime
- 1995-06-01 DE DE69528016T patent/DE69528016T2/de not_active Expired - Lifetime
- 1995-06-01 DK DK95303746T patent/DK0689845T3/da active
- 1995-06-01 IL IL11398495A patent/IL113984A/xx not_active IP Right Cessation
- 1995-06-02 NZ NZ272274A patent/NZ272274A/en not_active IP Right Cessation
- 1995-06-02 NZ NZ536440A patent/NZ536440A/en not_active IP Right Cessation
- 1995-06-02 FI FI952720A patent/FI117690B/fi not_active IP Right Cessation
- 1995-06-02 ZA ZA954570A patent/ZA954570B/xx unknown
- 1995-06-02 NO NO19952206A patent/NO313617B1/no not_active IP Right Cessation
- 1995-06-02 AU AU20449/95A patent/AU697280B2/en not_active Expired
- 1995-06-03 KR KR1019950014699A patent/KR100408376B1/ko not_active IP Right Cessation
- 1995-06-05 US US08/461,284 patent/US5739116A/en not_active Expired - Lifetime
- 1995-06-05 US US08/462,939 patent/US5767285A/en not_active Expired - Lifetime
-
1997
- 1997-05-14 BR BR1101078-9A patent/BR1101078A/pt active IP Right Grant
- 1997-05-14 BR BR1100990-0A patent/BR1100990A/pt active IP Right Grant
- 1997-09-17 NZ NZ328762A patent/NZ328762A/xx not_active IP Right Cessation
-
2003
- 2003-01-27 CY CY0300005A patent/CY2334B1/xx unknown
-
2005
- 2005-01-12 JP JP2005004986A patent/JP2005139200A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI117690B (fi) | Kasvainten vastaisten metyylitritioyhdisteiden konjugaatteja ja välituotteita niiden synteesiä varten | |
| EP0837698B1 (en) | Methods for the preparation of monomeric calicheamicin derivative/carrier conjugates | |
| US5714586A (en) | Methods for the preparation of monomeric calicheamicin derivative/carrier conjugates | |
| AU2013336410A1 (en) | Drug-protein conjugates | |
| JP2004528309A (ja) | 癌治療用分子複合体 | |
| FI95204B (fi) | Menetelmä metyylitritioyhdisteiden kohdennettujen johdannaisten valmistamiseksi | |
| HU210147B (en) | Process for producing antibody-drug conjugates and pharmaceutical compositions containing them | |
| IL93733A (en) | History of Dissolved Drug Sulphides Antibacterial and Antibacterial, Prepared from Compounds Containing Methyl-Thriteo Groups and Their Target Form | |
| IL132974A (en) | Compounds used in the manufacture of pairs of methylating agents against tumors | |
| CA2014459C (en) | Targeted forms of methyltrithio antitumor agents |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Patent granted |
Ref document number: 117690 Country of ref document: FI |
|
| MA | Patent expired |