JP2018502131A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018502131A5 JP2018502131A5 JP2017537229A JP2017537229A JP2018502131A5 JP 2018502131 A5 JP2018502131 A5 JP 2018502131A5 JP 2017537229 A JP2017537229 A JP 2017537229A JP 2017537229 A JP2017537229 A JP 2017537229A JP 2018502131 A5 JP2018502131 A5 JP 2018502131A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- double
- independently
- absent
- double line
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 9
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical class N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 8
- 229940049706 benzodiazepine Drugs 0.000 claims 8
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 4
- 241000257303 Hymenoptera Species 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 2
- 239000004471 Glycine Substances 0.000 claims 2
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 2
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 2
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 claims 2
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 2
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 claims 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- 229960003767 alanine Drugs 0.000 claims 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 2
- 229960003121 arginine Drugs 0.000 claims 2
- 235000009697 arginine Nutrition 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 235000003704 aspartic acid Nutrition 0.000 claims 2
- 229960005261 aspartic acid Drugs 0.000 claims 2
- 229940000635 beta-alanine Drugs 0.000 claims 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 2
- 235000013477 citrulline Nutrition 0.000 claims 2
- 229960002173 citrulline Drugs 0.000 claims 2
- 235000018417 cysteine Nutrition 0.000 claims 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 2
- UHBYWPGGCSDKFX-VKHMYHEASA-N gamma-carboxy-L-glutamic acid Chemical compound OC(=O)[C@@H](N)CC(C(O)=O)C(O)=O UHBYWPGGCSDKFX-VKHMYHEASA-N 0.000 claims 2
- 235000013922 glutamic acid Nutrition 0.000 claims 2
- 239000004220 glutamic acid Substances 0.000 claims 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 2
- 235000004554 glutamine Nutrition 0.000 claims 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 2
- 229960000310 isoleucine Drugs 0.000 claims 2
- 229930182817 methionine Natural products 0.000 claims 2
- 229960003104 ornithine Drugs 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 2
- 239000004474 valine Substances 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 0 C*1*c(*C(C(*2)N2c2c3c(*)c(*)c(OC)c2*)N(*2)C3=O)c2**1C Chemical compound C*1*c(*C(C(*2)N2c2c3c(*)c(*)c(OC)c2*)N(*2)C3=O)c2**1C 0.000 description 21
- JNEIGPOYXWTFRJ-SPDTVLEGSA-N CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cc(CO)cc(COc(cc(c5c6)N=C[C@](C)(Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O Chemical compound CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cc(CO)cc(COc(cc(c5c6)N=C[C@](C)(Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O JNEIGPOYXWTFRJ-SPDTVLEGSA-N 0.000 description 1
- SRGUIILOWHGIHP-FTCKZAFISA-N CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cc(O)cc(COc(cc(c5c6)N=C[C@](C)(Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O Chemical compound CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cc(O)cc(COc(cc(c5c6)N=C[C@](C)(Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O SRGUIILOWHGIHP-FTCKZAFISA-N 0.000 description 1
- STFDAZGKIBTMJX-DCOCMWOTSA-N CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cccc(COc(cc(c5c6)N=C[C@H](Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O Chemical compound CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cccc(COc(cc(c5c6)N=C[C@H](Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O STFDAZGKIBTMJX-DCOCMWOTSA-N 0.000 description 1
- SRNNMAYPFWIVBA-DLLNMANHSA-N CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cccc(COc(cc(c5c6)N=C[C@H](Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCOCCNC(CCN(C(C=C1)=O)C1=O)=O)=O Chemical compound CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cccc(COc(cc(c5c6)N=C[C@H](Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCOCCNC(CCN(C(C=C1)=O)C1=O)=O)=O SRNNMAYPFWIVBA-DLLNMANHSA-N 0.000 description 1
- WOMIHJWISPYCNW-GUYQLFMMSA-N CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cccc(COc(cc(c5c6)NC[C@H](Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(C(C)(C)CCOC(C)(C)CCN)=O Chemical compound CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cccc(COc(cc(c5c6)NC[C@H](Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(C(C)(C)CCOC(C)(C)CCN)=O WOMIHJWISPYCNW-GUYQLFMMSA-N 0.000 description 1
- JGDJLVXDIRWLKZ-GVZHZIMMSA-N CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cccc(COc(cc(c5c6)NC[C@](C)(Cc7c(C8)cccc7)N8C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O Chemical compound CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cccc(COc(cc(c5c6)NC[C@](C)(Cc7c(C8)cccc7)N8C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O JGDJLVXDIRWLKZ-GVZHZIMMSA-N 0.000 description 1
- KVSPLGQOVCTVMH-GVZHZIMMSA-N CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cncc(COc(cc(c5c6)N=C[C@](C)(Cc7ccccc7C7)N7C5=O)c6OC)c4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O Chemical compound CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4cncc(COc(cc(c5c6)N=C[C@](C)(Cc7ccccc7C7)N7C5=O)c6OC)c4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O KVSPLGQOVCTVMH-GVZHZIMMSA-N 0.000 description 1
- FFGOMIMEBCYKET-GVZHZIMMSA-N CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4nccc(COc(cc(c5c6)N=C[C@](C)(Cc7c(C8)cccc7)N8C5=O)c6OC)c4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O Chemical compound CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C(C2)N3Cc4c2cccc4)O)c(cc(c(OC)c2)OCc4nccc(COc(cc(c5c6)N=C[C@](C)(Cc7c(C8)cccc7)N8C5=O)c6OC)c4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O FFGOMIMEBCYKET-GVZHZIMMSA-N 0.000 description 1
- JJSNZLGGKLQXJZ-MAUNITOHSA-N CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C2N3Cc4ccccc4C2)O)c(cc(c(OC)c2)OCc4cc(OC)cc(COc(cc(c5c6)N=CC(Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O Chemical compound CC(C)[C@@H](C(N[C@@H](C)C(Nc1ccc(COC(N(C(C2N3Cc4ccccc4C2)O)c(cc(c(OC)c2)OCc4cc(OC)cc(COc(cc(c5c6)N=CC(Cc7ccccc7C7)N7C5=O)c6OC)n4)c2C3=O)=O)cc1)=O)=O)NC(CCCCCN(C(C=C1)=O)C1=O)=O JJSNZLGGKLQXJZ-MAUNITOHSA-N 0.000 description 1
- WGNDROORULYINQ-UHFFFAOYSA-N CC(C)c(cc1)ccc1NCCNC Chemical compound CC(C)c(cc1)ccc1NCCNC WGNDROORULYINQ-UHFFFAOYSA-N 0.000 description 1
- JQWCIBVMCCOXOW-UHFFFAOYSA-N CCC(C)(CCOC(C)(CC)CNCC(C)=O)C(CC)=O Chemical compound CCC(C)(CCOC(C)(CC)CNCC(C)=O)C(CC)=O JQWCIBVMCCOXOW-UHFFFAOYSA-N 0.000 description 1
- IZMGGMBJEGFFPH-CDRRMRQFSA-N COC(c1cc(COc(cc(c2c3)N=C[C@H](Cc4ccccc4C4)N4C2=O)c3OC)nc(COc(c(OC)c2)cc(N=CC(C3)N4Cc5c3cccc5)c2C4=O)c1)=O Chemical compound COC(c1cc(COc(cc(c2c3)N=C[C@H](Cc4ccccc4C4)N4C2=O)c3OC)nc(COc(c(OC)c2)cc(N=CC(C3)N4Cc5c3cccc5)c2C4=O)c1)=O IZMGGMBJEGFFPH-CDRRMRQFSA-N 0.000 description 1
- JFYRJYAWKPUOOJ-JEFWXSHNSA-N COc(c(OCc1cccc(COc(cc(c2c3)N=C[C@H](Cc4ccccc4C4)N4C2=O)c3OC)n1)c1)cc2c1NCC(Cc1c(C3)cccc1)N3C2=O Chemical compound COc(c(OCc1cccc(COc(cc(c2c3)N=C[C@H](Cc4ccccc4C4)N4C2=O)c3OC)n1)c1)cc2c1NCC(Cc1c(C3)cccc1)N3C2=O JFYRJYAWKPUOOJ-JEFWXSHNSA-N 0.000 description 1
- WQWMYLTUDRVMMZ-JEFWXSHNSA-N COc(cc(c(N=C[C@H]1N2Cc3ccccc3C1)c1)C2=O)c1OCc1cc(COc(c(OC)c2)cc(N=CC(C3)N4Cc5c3cccc5)c2C4=O)cnc1 Chemical compound COc(cc(c(N=C[C@H]1N2Cc3ccccc3C1)c1)C2=O)c1OCc1cc(COc(c(OC)c2)cc(N=CC(C3)N4Cc5c3cccc5)c2C4=O)cnc1 WQWMYLTUDRVMMZ-JEFWXSHNSA-N 0.000 description 1
- KLNKPZBLDATLQQ-JEFWXSHNSA-N COc(cc(c(N=C[C@H]1N2Cc3ccccc3C1)c1)C2=O)c1OCc1nc(COc(c(OC)c2)cc(N=CC(C3)N4Cc5c3cccc5)c2C4=O)cc(Cl)c1 Chemical compound COc(cc(c(N=C[C@H]1N2Cc3ccccc3C1)c1)C2=O)c1OCc1nc(COc(c(OC)c2)cc(N=CC(C3)N4Cc5c3cccc5)c2C4=O)cc(Cl)c1 KLNKPZBLDATLQQ-JEFWXSHNSA-N 0.000 description 1
- OHLKZRIKXRFFPR-CYZZXXEPSA-N COc(cc(c(N=C[C@H]1N2Cc3ccccc3C1)c1)C2=O)c1OCc1nc(COc(c(OC)c2)cc(N=CC(C3)N4Cc5c3cccc5)c2C4=O)cc(O)c1 Chemical compound COc(cc(c(N=C[C@H]1N2Cc3ccccc3C1)c1)C2=O)c1OCc1nc(COc(c(OC)c2)cc(N=CC(C3)N4Cc5c3cccc5)c2C4=O)cc(O)c1 OHLKZRIKXRFFPR-CYZZXXEPSA-N 0.000 description 1
- INLIJFLVDXBJQO-JEFWXSHNSA-N COc(cc(c(N=C[C@H]1N2Cc3ccccc3C1)c1)C2=O)c1OCc1nc(COc(c(OC)c2)cc(N=CC3N4Cc5cc(N)ccc5C3)c2C4=O)ccc1 Chemical compound COc(cc(c(N=C[C@H]1N2Cc3ccccc3C1)c1)C2=O)c1OCc1nc(COc(c(OC)c2)cc(N=CC3N4Cc5cc(N)ccc5C3)c2C4=O)ccc1 INLIJFLVDXBJQO-JEFWXSHNSA-N 0.000 description 1
- DCULULPAEAOWAE-JEFWXSHNSA-N COc(cc(c(NC[C@H]1N2Cc3ccccc3C1)c1)C2=O)c1OCc1nc(COc(c(OC)c2)cc(N=CC3N4Cc5cc(N)ccc5C3)c2C4=O)ccc1 Chemical compound COc(cc(c(NC[C@H]1N2Cc3ccccc3C1)c1)C2=O)c1OCc1nc(COc(c(OC)c2)cc(N=CC3N4Cc5cc(N)ccc5C3)c2C4=O)ccc1 DCULULPAEAOWAE-JEFWXSHNSA-N 0.000 description 1
- VICMNFQUIFSCTI-IUMCWLRYSA-N C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc(cc4)nc(COc(c(OC)c5)cc(N=CC6N7Cc8ccccc8C6)c5C7=O)c4OC)c3OC)N1C2=O Chemical compound C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc(cc4)nc(COc(c(OC)c5)cc(N=CC6N7Cc8ccccc8C6)c5C7=O)c4OC)c3OC)N1C2=O VICMNFQUIFSCTI-IUMCWLRYSA-N 0.000 description 1
- KDARSRFKYVDYIR-RMRJFPBVSA-N C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc4cc(COc(c(OC)c5)cc(N=CC(C6)N7Cc8c6cccc8)c5C7=O)nc5c4cccc5)c3OC)N1C2=O Chemical compound C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc4cc(COc(c(OC)c5)cc(N=CC(C6)N7Cc8c6cccc8)c5C7=O)nc5c4cccc5)c3OC)N1C2=O KDARSRFKYVDYIR-RMRJFPBVSA-N 0.000 description 1
- JXIGSOSSDMUJNX-OFSWJTNVSA-N C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc4cc(COc(c(OC)c5)cc(N=CC(C6)N7Cc8c6cccc8)c5C7=O)ncc4)c3OC)N1C2=O Chemical compound C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc4cc(COc(c(OC)c5)cc(N=CC(C6)N7Cc8c6cccc8)c5C7=O)ncc4)c3OC)N1C2=O JXIGSOSSDMUJNX-OFSWJTNVSA-N 0.000 description 1
- TYMNUFGGEQNHMS-JJLGEWHUSA-N C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc4nc(COc(c(OC)c5)cc(N=CC(C6)N7Cc8c6cccc8)c5C7=O)cc(CO)c4)c3OC)N1C2=O Chemical compound C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc4nc(COc(c(OC)c5)cc(N=CC(C6)N7Cc8c6cccc8)c5C7=O)cc(CO)c4)c3OC)N1C2=O TYMNUFGGEQNHMS-JJLGEWHUSA-N 0.000 description 1
- AVXZUENBMDBLNK-JWERODGISA-N C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc4nc(COc(c(OC)c5)cc(N=CC(C6)N7Cc8c6cccc8)c5C7=O)cc(OC)c4)c3OC)N1C2=O Chemical compound C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc4nc(COc(c(OC)c5)cc(N=CC(C6)N7Cc8c6cccc8)c5C7=O)cc(OC)c4)c3OC)N1C2=O AVXZUENBMDBLNK-JWERODGISA-N 0.000 description 1
- ZHRSYWKYBFQHPK-OFSWJTNVSA-N C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc4nc(COc(c(OC)c5)cc(N=CC(C6)N7Cc8c6cccc8)c5C7=O)ccc4)c3OC)N1C2=O Chemical compound C[C@](Cc1ccccc1C1)(C=Nc(c2c3)cc(OCc4nc(COc(c(OC)c5)cc(N=CC(C6)N7Cc8c6cccc8)c5C7=O)ccc4)c3OC)N1C2=O ZHRSYWKYBFQHPK-OFSWJTNVSA-N 0.000 description 1
- LGLAWMHOJDEJOM-OFSWJTNVSA-N C[C@](Cc1ccccc1C1)(CNc(c2c3)cc(OCc4nc(COc(c(OC)c5)cc(NCC(C6)N7Cc8c6cccc8)c5C7=O)ccc4)c3OC)N1C2=O Chemical compound C[C@](Cc1ccccc1C1)(CNc(c2c3)cc(OCc4nc(COc(c(OC)c5)cc(NCC(C6)N7Cc8c6cccc8)c5C7=O)ccc4)c3OC)N1C2=O LGLAWMHOJDEJOM-OFSWJTNVSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562103157P | 2015-01-14 | 2015-01-14 | |
| US62/103,157 | 2015-01-14 | ||
| US201562215938P | 2015-09-09 | 2015-09-09 | |
| US62/215,938 | 2015-09-09 | ||
| PCT/US2016/013154 WO2016115201A1 (en) | 2015-01-14 | 2016-01-13 | Heteroarylene-bridged benzodiazepine dimers, conjugates thereof, and methods of making and using |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018502131A JP2018502131A (ja) | 2018-01-25 |
| JP2018502131A5 true JP2018502131A5 (enExample) | 2019-02-14 |
| JP6676058B2 JP6676058B2 (ja) | 2020-04-08 |
Family
ID=55272673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017537229A Expired - Fee Related JP6676058B2 (ja) | 2015-01-14 | 2016-01-13 | ヘテロアリーレン架橋したベンゾジアゼピン二量体、そのコンジュゲート、ならびに製造および使用方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US9526801B2 (enExample) |
| EP (1) | EP3245207B1 (enExample) |
| JP (1) | JP6676058B2 (enExample) |
| KR (1) | KR20170102981A (enExample) |
| CN (1) | CN107231804B (enExample) |
| AU (1) | AU2016206808A1 (enExample) |
| BR (1) | BR112017014937A2 (enExample) |
| CA (1) | CA2973355A1 (enExample) |
| CL (1) | CL2017001825A1 (enExample) |
| CO (1) | CO2017008086A2 (enExample) |
| EA (1) | EA201791461A1 (enExample) |
| ES (1) | ES2747386T3 (enExample) |
| IL (1) | IL253401A0 (enExample) |
| MX (1) | MX2017009144A (enExample) |
| PE (1) | PE20171185A1 (enExample) |
| SG (1) | SG11201705645YA (enExample) |
| TW (1) | TW201632532A (enExample) |
| WO (1) | WO2016115201A1 (enExample) |
| ZA (1) | ZA201704739B (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9504694B2 (en) * | 2015-03-19 | 2016-11-29 | Cellerant Therapeutics, Inc. | Isoquinolidinobenzodiazepines |
| GB201510010D0 (en) | 2015-06-09 | 2015-07-22 | King S College London | PDD and BPD compounds |
| US20180339985A1 (en) | 2015-08-21 | 2018-11-29 | Femtogenix Limited | Pdd compounds |
| GB201514928D0 (en) | 2015-08-21 | 2015-10-07 | King S College London | PDD compounds |
| EP3484518B1 (en) | 2016-07-07 | 2024-08-14 | The Board of Trustees of the Leland Stanford Junior University | Antibody adjuvant conjugates |
| WO2018048975A1 (en) | 2016-09-09 | 2018-03-15 | Bristol-Myers Squibb Company | Use of an anti-pd-1 antibody in combination with an anti-mesothelin antibody in cancer treatment |
| JP2019530707A (ja) * | 2016-10-10 | 2019-10-24 | セレラント セラピューティクス インコーポレイテッド | イソキノリジノベンゾジアゼピン（ｉｑｂ）−１（クロロメチル）−２，３−ジヒドロ−１ｈ−ベンゾ［ｅ］インドール（ｃｂｉ）二量体 |
| US10738338B2 (en) | 2016-10-18 | 2020-08-11 | The Research Foundation for the State University | Method and composition for biocatalytic protein-oligonucleotide conjugation and protein-oligonucleotide conjugate |
| WO2018075842A1 (en) * | 2016-10-20 | 2018-04-26 | Bristol-Myers Squibb Company | Condensed benzodiazepine derivatives and conjugates made therefrom |
| JP2020514419A (ja) | 2017-03-15 | 2020-05-21 | シルバーバック セラピューティックス インコーポレイテッド | ベンズアゼピン化合物、そのコンジュゲート及び使用 |
| IL305224B2 (en) | 2017-04-20 | 2024-09-01 | Immunogen Inc | Methods of preparing indolinobenzodiazepine derivatives |
| GB201714115D0 (en) | 2017-09-04 | 2017-10-18 | Femtogenix Ltd | Cytotoxic agents |
| GB201806022D0 (en) * | 2018-04-12 | 2018-05-30 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| CN113444111A (zh) | 2018-05-29 | 2021-09-28 | 尹图赛利有限公司 | 新型苯二氮杂䓬衍生物及其用途 |
| TWI825144B (zh) | 2018-08-10 | 2023-12-11 | 美商思達利醫藥公司 | 第二型轉麩醯胺酸酶(tg2)抑制劑 |
| GB201814281D0 (en) * | 2018-09-03 | 2018-10-17 | Femtogenix Ltd | Cytotoxic agents |
| CN112930350A (zh) * | 2018-10-31 | 2021-06-08 | 尹图赛利有限公司 | 稠合杂环苯并二氮杂䓬衍生物及其用途 |
| WO2020092631A1 (en) * | 2018-10-31 | 2020-05-07 | Fred Hutchinson Cancer Research Center | Compositions and methods for detecting and treating cancers characterized by expression of mesothelin |
| WO2020112588A1 (en) | 2018-11-30 | 2020-06-04 | Bristol-Myers Squibb Company | Antibody comprising a glutamine-containing light chain c-terminal extension, conjugates thereof, and methods and uses |
| US12478686B2 (en) | 2018-12-12 | 2025-11-25 | Bristol-Myers Squibb Company | Antibodies modified for transglutaminase conjugation, conjugates thereof, and methods and uses |
| GB201901197D0 (en) | 2019-01-29 | 2019-03-20 | Femtogenix Ltd | G-A Crosslinking cytotoxic agents |
| JP2022525594A (ja) | 2019-03-15 | 2022-05-18 | ボルト バイオセラピューティクス、インコーポレーテッド | Ｈｅｒ２を標的とする免疫結合体 |
| US20240377413A1 (en) | 2019-09-16 | 2024-11-14 | Bristol-Myers Squibb Company | Dual capture method for analysis of antibody-drug conjugates |
| WO2021168274A1 (en) | 2020-02-21 | 2021-08-26 | Silverback Therapeutics, Inc. | Nectin-4 antibody conjugates and uses thereof |
| IL299508A (en) | 2020-07-01 | 2023-02-01 | Ars Pharmaceuticals Inc | Anti-asgr1 antibody conjugates and uses thereof |
| CN113203780B (zh) * | 2021-05-13 | 2022-05-31 | 桂林电子科技大学 | 一种非诊断目的无标记适配体传感器检测gpc3的方法 |
| CN119059939B (zh) * | 2024-11-05 | 2025-03-21 | 南京恒远科技开发有限公司 | Api的合成方法 |
Family Cites Families (105)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1981001145A1 (en) | 1979-10-18 | 1981-04-30 | Univ Illinois | Hydrolytic enzyme-activatible pro-drugs |
| US4475196A (en) | 1981-03-06 | 1984-10-02 | Zor Clair G | Instrument for locating faults in aircraft passenger reading light and attendant call control system |
| US4447233A (en) | 1981-04-10 | 1984-05-08 | Parker-Hannifin Corporation | Medication infusion pump |
| US4631190A (en) | 1981-06-26 | 1986-12-23 | Shen Wei C | Acidity-sensitive spacer molecule to control the release of pharmaceuticals from molecular carriers |
| US5144011A (en) | 1981-06-26 | 1992-09-01 | Boston University | Acidity-sensitive spacer molecule to control the release of pharmaceuticals from molecular carriers |
| US4439196A (en) | 1982-03-18 | 1984-03-27 | Merck & Co., Inc. | Osmotic drug delivery system |
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| US4447224A (en) | 1982-09-20 | 1984-05-08 | Infusaid Corporation | Variable flow implantable infusion apparatus |
| US4487603A (en) | 1982-11-26 | 1984-12-11 | Cordis Corporation | Implantable microinfusion pump system |
| US4486194A (en) | 1983-06-08 | 1984-12-04 | James Ferrara | Therapeutic device for administering medicaments through the skin |
| US4698420A (en) | 1985-02-25 | 1987-10-06 | Xoma Corporation | Antibody hybrid molecules and process for their preparation |
| US4596556A (en) | 1985-03-25 | 1986-06-24 | Bioject, Inc. | Hypodermic injection apparatus |
| US5374548A (en) | 1986-05-02 | 1994-12-20 | Genentech, Inc. | Methods and compositions for the attachment of proteins to liposomes using a glycophospholipid anchor |
| MX9203291A (es) | 1985-06-26 | 1992-08-01 | Liposome Co Inc | Metodo para acoplamiento de liposomas. |
| US4941880A (en) | 1987-06-19 | 1990-07-17 | Bioject, Inc. | Pre-filled ampule and non-invasive hypodermic injection device assembly |
| US4790824A (en) | 1987-06-19 | 1988-12-13 | Bioject, Inc. | Non-invasive hypodermic injection device |
| US5108921A (en) | 1989-04-03 | 1992-04-28 | Purdue Research Foundation | Method for enhanced transmembrane transport of exogenous molecules |
| US5064413A (en) | 1989-11-09 | 1991-11-12 | Bioject, Inc. | Needleless hypodermic injection device |
| US5312335A (en) | 1989-11-09 | 1994-05-17 | Bioject Inc. | Needleless hypodermic injection device |
| US5383851A (en) | 1992-07-24 | 1995-01-24 | Bioject Inc. | Needleless hypodermic injection device |
| US6214345B1 (en) | 1993-05-14 | 2001-04-10 | Bristol-Myers Squibb Co. | Lysosomal enzyme-cleavable antitumor drug conjugates |
| US6124345A (en) | 1996-05-31 | 2000-09-26 | Basf Aktiengesellschaft | Carbamoyl carboxylic acid amide oximes |
| DK1413582T3 (da) | 1998-08-27 | 2006-07-17 | Spirogen Ltd | Dimere pyrrolobenzodiazepiner |
| CN1371416B (zh) | 1999-08-24 | 2012-10-10 | 梅达里克斯公司 | 人ctla-4抗体及其应用 |
| ES2248397T3 (es) | 2000-11-02 | 2006-03-16 | MERCK SHARP & DOHME LTD. | Sulfamidas como inhibidores de la gamma-secretasa. |
| CN1463270A (zh) | 2001-05-31 | 2003-12-24 | 梅达莱克斯公司 | 细胞毒素、其有用的前体药物、连接基团和稳定剂 |
| US7091186B2 (en) | 2001-09-24 | 2006-08-15 | Seattle Genetics, Inc. | p-Amidobenzylethers in drug delivery agents |
| KR100829283B1 (ko) | 2002-01-09 | 2008-05-13 | 메다렉스, 인코포레이티드 | Ｃｄ３０에 대한 인간 모노클로날 항체 |
| SI2357006T1 (sl) | 2002-07-31 | 2016-01-29 | Seattle Genetics, Inc. | Konjugati zdravil in njihova uporaba za zdravljenje raka, avtoimunske bolezni ali infekcijske bolezni |
| GB0226593D0 (en) | 2002-11-14 | 2002-12-24 | Consultants Ltd | Compounds |
| EP1613274B1 (en) | 2003-04-15 | 2010-03-03 | GlaxoSmithKline LLC | Human il-18 substitution mutants and their conjugates |
| UY28424A1 (es) | 2003-07-22 | 2005-02-28 | Schering Ag | Anticuerpos rgi y usos de los mismos. |
| GB0416511D0 (en) | 2003-10-22 | 2004-08-25 | Spirogen Ltd | Pyrrolobenzodiazepines |
| WO2005051976A2 (en) | 2003-11-20 | 2005-06-09 | Ansata Therapeutics, Inc. | Protein and peptide ligation processes and one-step purification processes |
| US20050191293A1 (en) | 2003-12-10 | 2005-09-01 | Shrikant Deshpande | IP-10 antibodies and their uses |
| AU2005216251B2 (en) | 2004-02-23 | 2011-03-10 | Genentech, Inc. | Heterocyclic self-immolative linkers and conjugates |
| ES2398975T3 (es) | 2004-03-01 | 2013-03-25 | Spirogen Sàrl | Derivados de 11-hidroxi-5H-pirrolo[2,1-c][1,4]benzodiazepin-5-ona como intermedios clave para la preparación de pirrolobenzodiazepinas sustituidas en C2 |
| GB0404578D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Pyrrolobenzodiazepines |
| GB0404577D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Pyrrolobenzodiazepines |
| JP5166861B2 (ja) | 2004-03-09 | 2013-03-21 | スピロゲン リミティッド | ピロロベンゾジアゼピン |
| RU2402548C2 (ru) | 2004-05-19 | 2010-10-27 | Медарекс, Инк. | Химические линкеры и их конъюгаты |
| MXPA06013413A (es) | 2004-05-19 | 2007-01-23 | Medarex Inc | Enlazadores quimicos y conjugados de los mismos. |
| CN101065151B (zh) | 2004-09-23 | 2014-12-10 | 健泰科生物技术公司 | 半胱氨酸改造的抗体和偶联物 |
| DK1851250T3 (da) | 2005-02-18 | 2012-07-09 | Medarex Inc | Humant monoklonalt antistof mod prostataspecifikt membranantigen (psma) |
| JP5249587B2 (ja) | 2005-02-18 | 2013-07-31 | メダレックス， インク． | フコシル残基を欠く前立腺特異的膜抗原（ｐｓｍａ）に対するモノクローナル抗体 |
| US7714016B2 (en) | 2005-04-08 | 2010-05-11 | Medarex, Inc. | Cytotoxic compounds and conjugates with cleavable substrates |
| SI1879901T1 (sl) | 2005-04-21 | 2010-04-30 | Spirogen Ltd | Pirolobenzodiazepini |
| EP2418278A3 (en) | 2005-05-09 | 2012-07-04 | Ono Pharmaceutical Co., Ltd. | Human monoclonal antibodies to programmed death 1(PD-1) and methods for treating cancer using anti-PD-1 antibodies alone or in combination with other immunotherapeutics |
| WO2007002223A2 (en) | 2005-06-20 | 2007-01-04 | Medarex, Inc. | Cd19 antibodies and their uses |
| KR101607288B1 (ko) | 2005-07-01 | 2016-04-05 | 이. 알. 스퀴부 앤드 선즈, 엘.엘.씨. | 예정 사멸 리간드 1 (피디-엘1)에 대한 인간 모노클로날 항체 |
| SI3248613T1 (sl) | 2005-07-18 | 2022-04-29 | Seagen Inc. | Konjugati beta-glukuronidni linker-zdravilo |
| AU2006294663B2 (en) | 2005-09-26 | 2012-03-22 | Medarex, Inc. | Human monoclonal antibodies to CD70 |
| ES2416136T3 (es) | 2005-09-26 | 2013-07-30 | Medarex, Inc. | Conjugados de anticuerpo-fármaco y su uso |
| ES2375843T3 (es) | 2005-10-26 | 2012-03-06 | Medarex, Inc. | Procedimientos y compuestos para la preparación de an�?logos de cc-1065. |
| WO2007059404A2 (en) | 2005-11-10 | 2007-05-24 | Medarex, Inc. | Duocarmycin derivatives as novel cytotoxic compounds and conjugates |
| SG177194A1 (en) | 2005-12-08 | 2012-01-30 | Medarex Inc | Human monoclonal antibodies to protein tyrosine kinase 7 (ptk7) and methods for using anti-ptk7 antibodies |
| JP5714212B2 (ja) | 2005-12-08 | 2015-05-07 | メダレックス・リミテッド・ライアビリティ・カンパニーＭｅｄａｒｅｘ， Ｌ．Ｌ．Ｃ． | Ｏ８ｅに対するヒトモノクローナル抗体 |
| HRP20120701T1 (hr) | 2005-12-08 | 2012-10-31 | Medarex, Inc. | Humana monoklonska protutijela protiv fukozil-gm1 i postupci za uporabu antifukozil-gm1 |
| KR100869414B1 (ko) | 2005-12-13 | 2008-11-21 | 야마하 가부시키가이샤 | 건반식 음판 타악기용의 음판 및 그 제조방법, 음판타악기의 음원 유닛 및 건반식 타악기 |
| DK1813614T3 (da) | 2006-01-25 | 2012-01-23 | Sanofi Sa | Cytotoksiske midler, der omfatter nye tomaymycinderivater |
| CA2647632C (en) | 2006-03-27 | 2017-06-27 | University Of Maryland Biotechnology Institute | Glycoprotein synthesis and remodeling by enzymatic transglycosylation |
| RU2318818C1 (ru) * | 2006-04-12 | 2008-03-10 | Общество С Ограниченной Ответственностью "Исследовательский Институт Химического Разнообразия" | Азагетероциклы, комбинаторная библиотека, фокусированная библиотека, фармацевтическая композиция и способ получения (варианты) |
| CN101479379B (zh) | 2006-06-29 | 2012-01-18 | 利兰·斯坦福青年大学托管委员会 | 含有非天然氨基酸的蛋白质的无细胞合成 |
| CA2662752C (en) | 2006-09-08 | 2016-04-12 | Ambrx, Inc. | Site specific incorporation of non-natural amino acids by vertebrate cells |
| AR063086A1 (es) | 2006-10-02 | 2008-12-23 | Medarex Inc | Anticuerpos humanos que se unen a cxcr4 y usos de los mismos |
| NZ578064A (en) | 2006-12-01 | 2012-01-12 | Medarex Inc | Human antibodies that bind cd22 and uses thereof |
| UY30776A1 (es) | 2006-12-21 | 2008-07-03 | Medarex Inc | Anticuerpos cd44 |
| 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 |
| CN101616911A (zh) | 2007-02-21 | 2009-12-30 | 梅达莱克斯公司 | 具有单个氨基酸的化学连接物及其偶联物 |
| CN101815726B (zh) | 2007-07-17 | 2013-04-03 | 米德列斯公司 | 针对磷脂酰肌醇蛋白聚糖-3的单克隆抗体 |
| SI2019104T1 (sl) | 2007-07-19 | 2013-12-31 | Sanofi | Citotoksična sredstva, ki obsegajo nove tomaimicinske derivate, in njihova terapevtska uporaba |
| US8865875B2 (en) | 2007-08-22 | 2014-10-21 | Medarex, L.L.C. | Site-specific attachment of drugs or other agents to engineered antibodies with C-terminal extensions |
| AU2008308956B2 (en) | 2007-10-01 | 2013-03-14 | Bristol-Myers Squibb Company | Human antibodies that bind mesothelin, and uses thereof |
| GB0813432D0 (en) | 2008-07-22 | 2008-08-27 | Spirogen Ltd | Pyrrolobenzodiazepines |
| GB0819095D0 (en) | 2008-10-17 | 2008-11-26 | Spirogen Ltd | Pyrrolobenzodiazepines |
| WO2010087994A2 (en) | 2009-01-30 | 2010-08-05 | Whitehead Institute For Biomedical Research | Methods for ligation and uses thereof |
| EP3100745B1 (en) * | 2009-02-05 | 2018-04-18 | Immunogen, Inc. | Novel benzodiazepine derivatives |
| FR2949469A1 (fr) | 2009-08-25 | 2011-03-04 | Sanofi Aventis | Derives anticancereux, leur preparation et leur application en therapeutique |
| BR112012026213B1 (pt) | 2010-04-15 | 2021-12-28 | Medimmune Limited | Compostos de pirrolobenzodiazepinas, conjugado das mesmas, composição farmacêutica compreendendo o conjugado e uso do mesmo para o tratamento de uma doença proliferativa |
| MX368648B (es) | 2010-04-15 | 2019-10-09 | Seattle Genetics Inc | Pirrolobenzodiazepinas usadas para tratar enfermedades proliferativas. |
| NZ602932A (en) | 2010-04-15 | 2014-08-29 | Seattle Genetics Inc | Targeted pyrrolobenzodiazapine conjugates |
| FR2963007B1 (fr) * | 2010-07-26 | 2013-04-05 | Sanofi Aventis | Derives anticancereux, leur preparation et leur application therapeutique |
| EP2675479B1 (en) * | 2011-02-15 | 2016-01-13 | Immunogen, Inc. | Cytotoxic benzodiazepine derivatives |
| WO2012153253A2 (en) | 2011-05-06 | 2012-11-15 | Jan Gysbert Hermanus Du Preez | Aromatic compounds and metal complexes thereof |
| MX341524B (es) | 2011-09-20 | 2016-08-24 | Medimmune Ltd | Pirrolobenzodiazepinas como compuestos pbd dimericos asimetricos para inclusion en conjugados dirigidos. |
| KR101891859B1 (ko) | 2011-10-14 | 2018-08-24 | 메디뮨 리미티드 | 피롤로벤조디아제핀 |
| SG11201401406YA (en) | 2011-10-14 | 2014-05-29 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| CA2850373C (en) | 2011-10-14 | 2019-07-16 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| AU2012322613B2 (en) | 2011-10-14 | 2016-04-21 | Medimmune Limited | Pyrrolobenzodiazepines and targeted conjugates |
| EP2751110B1 (en) | 2011-10-14 | 2017-04-19 | MedImmune Limited | Asymmetrical bis-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-5-one) derivatives for the treatment of proliferative and autoimmune diseases |
| WO2013085925A1 (en) | 2011-12-05 | 2013-06-13 | Igenica, Inc. | Antibody-drug conjugates and related compounds, compositions, and methods |
| WO2013177481A1 (en) | 2012-05-25 | 2013-11-28 | Immunogen, Inc. | Benzodiazepines and conjugates thereof |
| HK1204924A1 (en) | 2012-06-19 | 2015-12-11 | Polytherics Limited | Process for preparation of antibody conjugates and antibody conjugates |
| WO2014031566A1 (en) * | 2012-08-22 | 2014-02-27 | Immunogen, Inc. | Cytotoxic benzodiazepine derivatives |
| WO2014047024A1 (en) | 2012-09-18 | 2014-03-27 | Bristol-Myers Squibb Company | Iap antagonists |
| ES2713164T3 (es) | 2012-10-12 | 2019-05-20 | Medimmune Ltd | Pirrolobenzodiazepinas y conjugados de las mismas |
| WO2014057074A1 (en) | 2012-10-12 | 2014-04-17 | Spirogen Sàrl | Pyrrolobenzodiazepines and conjugates thereof |
| 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 |
| JP6307519B2 (ja) | 2012-12-21 | 2018-04-04 | メドイミューン・リミテッドＭｅｄＩｍｍｕｎｅ Ｌｉｍｉｔｅｄ | ピロロベンゾジアゼピンおよびその結合体 |
| CN110627797A (zh) | 2012-12-21 | 2019-12-31 | 麦迪穆有限责任公司 | 用于治疗增殖性和自身免疫疾病的非对称吡咯并苯并二氮杂卓二聚物 |
| JP6340019B2 (ja) | 2013-03-13 | 2018-06-06 | メドイミューン・リミテッドＭｅｄＩｍｍｕｎｅ Ｌｉｍｉｔｅｄ | ピロロベンゾジアゼピン及びそのコンジュゲート |
| EP2968596B1 (en) | 2013-03-13 | 2019-03-06 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| AU2014230735B2 (en) | 2013-03-13 | 2018-03-15 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| WO2014174111A1 (en) | 2013-04-26 | 2014-10-30 | Pierre Fabre Medicament | Axl antibody-drug conjugate and its use for the treatment of cancer |
| US9527871B2 (en) * | 2015-01-14 | 2016-12-27 | Bristol-Myers Squibb Company | Benzodiazepine dimers, conjugates thereof, and methods of making and using |
-
2016
- 2016-01-13 PE PE2017001217A patent/PE20171185A1/es unknown
- 2016-01-13 EA EA201791461A patent/EA201791461A1/ru unknown
- 2016-01-13 KR KR1020177022246A patent/KR20170102981A/ko active Pending
- 2016-01-13 SG SG11201705645YA patent/SG11201705645YA/en unknown
- 2016-01-13 TW TW105100988A patent/TW201632532A/zh unknown
- 2016-01-13 WO PCT/US2016/013154 patent/WO2016115201A1/en not_active Ceased
- 2016-01-13 ES ES16702266T patent/ES2747386T3/es active Active
- 2016-01-13 EP EP16702266.4A patent/EP3245207B1/en active Active
- 2016-01-13 CN CN201680006152.XA patent/CN107231804B/zh active Active
- 2016-01-13 CA CA2973355A patent/CA2973355A1/en not_active Abandoned
- 2016-01-13 BR BR112017014937A patent/BR112017014937A2/pt not_active Application Discontinuation
- 2016-01-13 AU AU2016206808A patent/AU2016206808A1/en not_active Abandoned
- 2016-01-13 MX MX2017009144A patent/MX2017009144A/es unknown
- 2016-01-13 JP JP2017537229A patent/JP6676058B2/ja not_active Expired - Fee Related
- 2016-01-13 US US14/994,378 patent/US9526801B2/en active Active
- 2016-11-15 US US15/351,955 patent/US9676775B2/en active Active
-
2017
- 2017-05-05 US US15/587,679 patent/US9822112B2/en active Active
- 2017-07-10 IL IL253401A patent/IL253401A0/en unknown
- 2017-07-13 ZA ZA2017/04739A patent/ZA201704739B/en unknown
- 2017-07-13 CL CL2017001825A patent/CL2017001825A1/es unknown
- 2017-08-10 CO CONC2017/0008086A patent/CO2017008086A2/es unknown
- 2017-10-17 US US15/785,608 patent/US20180037581A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018502131A5 (enExample) | ||
| JP2018503639A5 (enExample) | ||
| JP2018518506A5 (enExample) | ||
| RU2477723C2 (ru) | Ингибиторы протеинкиназ (варианты), их применение для лечения онкологических заболеваний и фармацевтическая композиция на их основе | |
| JP2015508074A5 (enExample) | ||
| JP2013519632A5 (enExample) | ||
| JP2014527974A5 (enExample) | ||
| JP2020506951A5 (enExample) | ||
| JP2016006096A5 (enExample) | ||
| JP2014528467A5 (enExample) | ||
| JP2017503777A5 (enExample) | ||
| RU2019112029A (ru) | Применение комбинации антитела к pd-1 и ингибитора vegfr в изготовлении лекарственного средства для лечения злокачественных новообразований | |
| HRP20170433T1 (hr) | Pripravci spoja za izmjenu lipidiranog imunološkog odgovora, formulacije, i postupci | |
| JP2009504763A5 (enExample) | ||
| JP2016506916A5 (enExample) | ||
| RU2016136091A (ru) | Соединения, воздействующие на днк-связывающий домен (dbd) андрогенового рецептора человека, в качестве терапевтических средств, а также способы их применения | |
| JP2009504764A5 (enExample) | ||
| JP2014528466A5 (enExample) | ||
| JP2018511628A5 (enExample) | ||
| JP2013500304A5 (enExample) | ||
| RU2008126305A (ru) | Новый пептид | |
| HRP20170334T1 (hr) | Spojevi enedina, njihovi konjugati, primjene i metode | |
| CY1125446T1 (el) | Λιποσωμικο σκευασμα για χρηση στη θεραπεία καρκινου | |
| RU2016122731A (ru) | Функционализированные и замещенные индолы в качестве противораковых агентов | |
| RU2016150326A (ru) | Производные изоиндолина для применения в лечении вирусной инфекции |