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 |
| GB201514928D0 (en) | 2015-08-21 | 2015-10-07 | King S College London | PDD compounds |
| US20180339985A1 (en) | 2015-08-21 | 2018-11-29 | Femtogenix Limited | Pdd compounds |
| ES2990113T3 (es) | 2016-07-07 | 2024-11-28 | The Board Of Trustees Of The Leland Stanfordjunior Univ | Conjugados de adyuvantes de anticuerpos |
| US20190218294A1 (en) | 2016-09-09 | 2019-07-18 | Bristol-Myers Squibb Company | Use of an anti-pd-1 antibody in combination with an anti-mesothelin antibody in cancer treatment |
| CN110049780A (zh) * | 2016-10-10 | 2019-07-23 | 塞勒兰特治疗公司 | 异喹啉并苯并二氮杂卓(iqb)-1(氯甲基)-2,3-二氢-1h-苯并[e]吲哚(cbi)二聚体 |
| 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 |
| DK3595668T3 (da) | 2017-03-15 | 2021-10-18 | Silverback Therapeutics Inc | Benzazepinforbindelser, konjugater og anvendelser deraf |
| KR20230154089A (ko) | 2017-04-20 | 2023-11-07 | 이뮤노젠 아이엔씨 | 인돌리노벤조다이아제핀 유도체를 제조하는 방법 |
| 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 |
| BR112020023623A2 (pt) * | 2018-05-29 | 2021-02-17 | Intocell, Inc. | derivados de benzodiazepina e seus usos |
| 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 |
| 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 |
| AU2019370859B2 (en) | 2018-10-31 | 2023-09-21 | Intocell, Inc. | Fused heterocyclic benzodiazepine derivatives and uses thereof |
| AU2019386945B9 (en) | 2018-11-30 | 2025-10-23 | Bristol-Myers Squibb Company | Antibody comprising a glutamine-containing light chain C-terminal extension, conjugates thereof, and methods and uses |
| KR20210102334A (ko) | 2018-12-12 | 2021-08-19 | 브리스톨-마이어스 스큅 컴퍼니 | 트랜스글루타미나제 접합을 위해 변형된 항체, 그의 접합체, 및 방법 및 용도 |
| GB201901197D0 (en) | 2019-01-29 | 2019-03-20 | Femtogenix Ltd | G-A Crosslinking cytotoxic agents |
| CN113993549A (zh) | 2019-03-15 | 2022-01-28 | 博尔特生物治疗药物有限公司 | 靶向her2的免疫缀合物 |
| US20240377413A1 (en) | 2019-09-16 | 2024-11-14 | Bristol-Myers Squibb Company | Dual capture method for analysis of antibody-drug conjugates |
| JP7735291B2 (ja) | 2020-02-21 | 2025-09-08 | エーアールエス ファーマシューティカルズ、インコーポレイテッド | ネクチン－４抗体コンジュゲートおよびその使用 |
| CA3183993A1 (en) | 2020-07-01 | 2022-01-06 | Peter R. Baum | 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. |
| US4790824A (en) | 1987-06-19 | 1988-12-13 | Bioject, Inc. | Non-invasive hypodermic injection device |
| US4941880A (en) | 1987-06-19 | 1990-07-17 | Bioject, Inc. | Pre-filled ampule and non-invasive hypodermic injection device assembly |
| 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 |
| EP0906271B1 (de) | 1996-05-31 | 2002-02-06 | Basf Aktiengesellschaft | Carbamoylcarbonsäureamidoxime |
| NZ510493A (en) | 1998-08-27 | 2003-11-28 | Spirogen Ltd | Pyrrolobenzodiazepin-5-one derivatives for treating viral, bacterial and protozoal infections |
| DK1212422T3 (da) | 1999-08-24 | 2007-07-02 | Medarex Inc | Humane CTLA-4-antistoffer og anvendelserne deraf |
| CA2427206C (en) | 2000-11-02 | 2011-06-28 | Merck Sharp & Dohme Limited | Sulfamides as gamma-secretase inhibitors |
| KR20030033007A (ko) | 2001-05-31 | 2003-04-26 | 코울터 파머수티컬, 인코포레이티드 | 세포독소, 약물전구체, 링커 및 이에 유용한 안정화제 |
| US7091186B2 (en) | 2001-09-24 | 2006-08-15 | Seattle Genetics, Inc. | p-Amidobenzylethers in drug delivery agents |
| WO2003059282A2 (en) | 2002-01-09 | 2003-07-24 | Medarex, Inc. | Human monoclonal antibodies against cd30 |
| SI1545613T1 (sl) | 2002-07-31 | 2011-11-30 | Seattle Genetics Inc | Avristatinski konjugati in njihova uporaba za zdravljenje raka avtoimunske bolezni ali infekcijskebolezni |
| GB0226593D0 (en) | 2002-11-14 | 2002-12-24 | Consultants Ltd | Compounds |
| DE602004025799D1 (de) | 2003-04-15 | 2010-04-15 | Glaxosmithkline Llc | Humane il-18 substitutionsmutanten und deren konjugate |
| JP4680902B2 (ja) | 2003-07-22 | 2011-05-11 | バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト | Ｒｇ１抗体及びその使用 |
| 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 |
| JP5064037B2 (ja) | 2004-02-23 | 2012-10-31 | ジェネンテック， インコーポレイテッド | 複素環式自壊的リンカーおよび結合体 |
| GB0404578D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Pyrrolobenzodiazepines |
| SI2270010T1 (sl) | 2004-03-01 | 2012-05-31 | Spirogen Ltd | hidroksi H pirolo c benzodiazepin onski derivati kot ključni intermediati za pripravo C substituiranih pirolobenzodiazepinov |
| GB0404577D0 (en) | 2004-03-01 | 2004-04-07 | Spirogen Ltd | Pyrrolobenzodiazepines |
| WO2005085260A1 (en) | 2004-03-09 | 2005-09-15 | Spirogen Limited | Pyrrolobenzodiazepines |
| BRPI0510909A2 (pt) | 2004-05-19 | 2008-12-16 | Medarex Inc | composto de ligaÇço fÁrmaco-ligante citotàxico, formulaÇço farmacÊutica, mÉtodo para matar uma cÉlula e mÉtodo para retardar ou interromper o crescimento de tumor |
| RU2402548C2 (ru) | 2004-05-19 | 2010-10-27 | Медарекс, Инк. | Химические линкеры и их конъюгаты |
| ES2579805T3 (es) | 2004-09-23 | 2016-08-16 | Genentech, Inc. | Anticuerpos y conjugados modificados por ingeniería genética con cisteína |
| WO2006089231A2 (en) | 2005-02-18 | 2006-08-24 | Medarex, Inc. | Monoclonal antibodies against prostate specific membrane antigen (psma) lacking in fucosyl residues |
| JP2008529556A (ja) | 2005-02-18 | 2008-08-07 | メダレックス， インク． | 前立腺特異的膜抗原（ｐｓｍａ）に対するヒト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 |
| PL1879901T3 (pl) | 2005-04-21 | 2010-06-30 | Medimmune Ltd | Pirolobenzodiazepiny |
| KR101498834B1 (ko) | 2005-05-09 | 2015-03-05 | 오노 야꾸힝 고교 가부시키가이샤 | 예정 사멸 인자 1(ｐｄ-1)에 대한 인간 모노클로날 항체, 및 항-ｐｄ-1 항체를 단독 사용하거나 기타 면역 요법제와 병용한 암 치료 방법 |
| EP1899379B1 (en) | 2005-06-20 | 2018-04-11 | E. R. Squibb & Sons, L.L.C. | Cd19 antibodies and their uses |
| HRP20080053A2 (hr) | 2005-07-01 | 2009-08-31 | Medarex | Ljudska monoklonska protutijela na ligand 1 za programiranu smrt stanice (pd-l1) |
| AU2006269940C1 (en) | 2005-07-18 | 2013-11-07 | Seagen Inc. | Beta-glucuronide-linker drug conjugates |
| WO2007038658A2 (en) | 2005-09-26 | 2007-04-05 | Medarex, Inc. | Antibody-drug conjugates and methods of use |
| EP1934261B1 (en) | 2005-09-26 | 2014-10-29 | Medarex, L.L.C. | Human monoclonal antibodies to cd70 |
| 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 |
| 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 |
| BRPI0620601A2 (pt) | 2005-12-08 | 2011-11-16 | Medarex Inc | anticorpo monoclonal humano isolado ou uma porção ligante ao antìgeno do mesmo, composição, imunoconjugado, molécula de ácido nucléico isolada, vetor de expressão, célula hospedeira, método para preparar um anticorpo anti-o8e e método para tratar ou prevenir uma doença definida pelo crescimento de células tumorais expressando o8e |
| NZ568551A (en) | 2005-12-08 | 2012-03-30 | Medarex Inc | Human monoclonal antibodies to Fucosyl-GM1 and methods using anti-Fucosyl-GM1 |
| KR100869414B1 (ko) | 2005-12-13 | 2008-11-21 | 야마하 가부시키가이샤 | 건반식 음판 타악기용의 음판 및 그 제조방법, 음판타악기의 음원 유닛 및 건반식 타악기 |
| SI1813614T1 (sl) | 2006-01-25 | 2012-01-31 | Sanofi 174 | Citotoksična sredstva, ki obsegajo nove tomajmicinske derivate |
| 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) |
| EP2035554B1 (en) | 2006-06-29 | 2013-04-24 | The Board of Trustees of The Leland Stanford Junior University | Cell-free synthesis of proteins containing unnatural amino acids |
| KR20090057072A (ko) | 2006-09-08 | 2009-06-03 | 암브룩스, 인코포레이티드 | 척추동물 세포에 의한 비천연 아미노산의 부위 특이적 도입 |
| AU2007320024B2 (en) | 2006-10-02 | 2012-11-08 | E. R. Squibb & Sons, L.L.C. | Human antibodies that bind CXCR4 and uses thereof |
| CA2671457C (en) | 2006-12-01 | 2017-09-26 | 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 |
| ME02345B (me) | 2007-07-17 | 2016-08-31 | Squibb & Sons Llc | MONOKLONSKA ANTlTELA PROTIV GLIPIKANA-3 |
| EP2019104B1 (en) | 2007-07-19 | 2013-09-04 | Sanofi | Cytotoxic agents comprising new tomaymycin derivatives and their therapeutic use |
| EP2185188B1 (en) | 2007-08-22 | 2014-08-06 | Medarex, L.L.C. | Site-specific attachment of drugs or other agents to engineered antibodies with c-terminal extensions |
| NZ584633A (en) | 2007-10-01 | 2011-11-25 | Bristol Myers Squibb Co | 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 |
| JP5977522B2 (ja) | 2009-02-05 | 2016-08-24 | イミュノジェン・インコーポレーテッド | 新規ベンゾジアゼピン誘導体 |
| FR2949469A1 (fr) | 2009-08-25 | 2011-03-04 | Sanofi Aventis | Derives anticancereux, leur preparation et leur application en therapeutique |
| JP5875083B2 (ja) | 2010-04-15 | 2016-03-02 | メディミューン リミテッド | 増殖性疾患治療用ピロロベンゾジアゼピン |
| RS52983B (sr) | 2010-04-15 | 2014-02-28 | Spirogen Sárl | Pirolobenzodiazepini i njihovi konjugati |
| EP2558127B1 (en) | 2010-04-15 | 2022-01-19 | Seagen Inc. | Targeted pyrrolobenzodiazepine conjugates |
| FR2963007B1 (fr) * | 2010-07-26 | 2013-04-05 | Sanofi Aventis | Derives anticancereux, leur preparation et leur application therapeutique |
| TWI617555B (zh) * | 2011-02-15 | 2018-03-11 | 免疫原公司 | 細胞毒性苯并二氮呯衍生物 |
| WO2012153253A2 (en) | 2011-05-06 | 2012-11-15 | Jan Gysbert Hermanus Du Preez | Aromatic compounds and metal complexes thereof |
| KR101860174B1 (ko) | 2011-09-20 | 2018-05-21 | 메디뮨 리미티드 | 표적 접합체 내의 내포를 위한 비대칭 이량체 pbd 화합물로서 피롤로벤조디아제핀 |
| US9387259B2 (en) | 2011-10-14 | 2016-07-12 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| HUE025661T2 (en) | 2011-10-14 | 2016-04-28 | Medimmune Ltd | Pyrrolobenzodiazepines and their conjugates |
| EA027386B1 (ru) | 2011-10-14 | 2017-07-31 | Медимьюн Лимитед | Пирролобензодиазепины |
| ES2945932T3 (es) | 2011-10-14 | 2023-07-10 | Seagen Inc | Pirrolobenzodiazepinas y conjugados dirigidos |
| EP2751111B1 (en) | 2011-10-14 | 2017-04-26 | MedImmune Limited | Asymmetrical bis-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-5-one) derivatives for the treatment of proliferative or autoimmune diseases |
| MX2014006739A (es) | 2011-12-05 | 2015-06-05 | Igenica Biotherapeutics Inc | Conjugados de anticuerpo-farmaco y compuestos relacionados, composiciones , y metodos. |
| WO2013177481A1 (en) | 2012-05-25 | 2013-11-28 | Immunogen, Inc. | Benzodiazepines and conjugates thereof |
| SG11201407600UA (en) | 2012-06-19 | 2014-12-30 | Polytherics Ltd | Novel process for preparation of antibody conjugates and novel antibody conjugates |
| HK1211208A1 (zh) | 2012-08-22 | 2016-05-20 | Immunogen, Inc. | 細胞毒性苯並二氮呯衍生物 |
| EP2897949B1 (en) | 2012-09-18 | 2018-01-10 | Bristol-Myers Squibb Company | Iap antagonists |
| SI2766048T1 (sl) | 2012-10-12 | 2015-03-31 | Spirogen Sarl | Pirolobenzodiazepini in njihovi konjugati |
| LT2906248T (lt) | 2012-10-12 | 2019-02-11 | Medimmune Limited | Pirolobenzodiazepinai ir jų konjugatai |
| AU2012395148B2 (en) | 2012-11-24 | 2016-10-27 | Hangzhou Dac Biotech Co., Ltd. | Hydrophilic linkers and their uses for conjugation of drugs to cell binding molecules |
| CA2894959C (en) | 2012-12-21 | 2022-01-11 | Spirogen Sarl | Unsymmetrical pyrrolobenzodiazepines-dimers for use in the treatment of proliferative and autoimmune diseases |
| CN110452242A (zh) | 2012-12-21 | 2019-11-15 | 麦迪穆有限责任公司 | 吡咯并苯并二氮杂卓及其结合物 |
| ES2731779T3 (es) | 2013-03-13 | 2019-11-19 | Medimmune Ltd | Pirrolobenzodiazepinas y conjugados de las mismas |
| MX362970B (es) | 2013-03-13 | 2019-02-28 | Medimmune Ltd | Pirrolobenzodiazepinas y conjugados de las mismas. |
| MX363787B (es) | 2013-03-13 | 2019-04-03 | Medimmune Ltd | Pirrolobenzodiazepinas y conjugados de los mismos. |
| JP2016518382A (ja) | 2013-04-26 | 2016-06-23 | ピエール、ファーブル、メディカマン | Ａｘｌ抗体薬物複合体および癌の治療のためのその使用 |
| AU2016206798A1 (en) * | 2015-01-14 | 2017-08-31 | 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 AU AU2016206808A patent/AU2016206808A1/en not_active Abandoned
- 2016-01-13 EP EP16702266.4A patent/EP3245207B1/en active Active
- 2016-01-13 ES ES16702266T patent/ES2747386T3/es active Active
- 2016-01-13 CN CN201680006152.XA patent/CN107231804B/zh not_active Expired - Fee Related
- 2016-01-13 TW TW105100988A patent/TW201632532A/zh unknown
- 2016-01-13 EA EA201791461A patent/EA201791461A1/ru unknown
- 2016-01-13 US US14/994,378 patent/US9526801B2/en active Active
- 2016-01-13 SG SG11201705645YA patent/SG11201705645YA/en unknown
- 2016-01-13 CA CA2973355A patent/CA2973355A1/en not_active Abandoned
- 2016-01-13 MX MX2017009144A patent/MX2017009144A/es unknown
- 2016-01-13 KR KR1020177022246A patent/KR20170102981A/ko active Pending
- 2016-01-13 WO PCT/US2016/013154 patent/WO2016115201A1/en not_active Ceased
- 2016-01-13 JP JP2017537229A patent/JP6676058B2/ja not_active Expired - Fee Related
- 2016-01-13 BR BR112017014937A patent/BR112017014937A2/pt not_active Application Discontinuation
- 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 CL CL2017001825A patent/CL2017001825A1/es unknown
- 2017-07-13 ZA ZA2017/04739A patent/ZA201704739B/en 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 | |
| JP2016521256A5 (enExample) | ||
| JP2015508074A5 (enExample) | ||
| JP2013519632A5 (enExample) | ||
| JP2014527974A5 (enExample) | ||
| JP2016505586A5 (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) | ||
| JP2018516243A5 (enExample) | ||
| JP2016506916A5 (enExample) | ||
| RU2016136091A (ru) | Соединения, воздействующие на днк-связывающий домен (dbd) андрогенового рецептора человека, в качестве терапевтических средств, а также способы их применения | |
| JP2018511628A5 (enExample) | ||
| JP2013500304A5 (enExample) | ||
| HRP20170334T1 (hr) | Spojevi enedina, njihovi konjugati, primjene i metode | |
| US20200297693A1 (en) | Glucose conjugates of triptolide, analogs and uses thereof | |
| RU2018146886A (ru) | Пути терапевтического применения ингибитора c-raf | |
| CY1125446T1 (el) | Λιποσωμικο σκευασμα για χρηση στη θεραπεία καρκινου |