JP2019507126A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019507126A5 JP2019507126A5 JP2018539095A JP2018539095A JP2019507126A5 JP 2019507126 A5 JP2019507126 A5 JP 2019507126A5 JP 2018539095 A JP2018539095 A JP 2018539095A JP 2018539095 A JP2018539095 A JP 2018539095A JP 2019507126 A5 JP2019507126 A5 JP 2019507126A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- heterocyclyl
- haloalkyl
- aryl
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims 64
- 229910052739 hydrogen Inorganic materials 0.000 claims 56
- 239000001257 hydrogen Substances 0.000 claims 56
- 150000002431 hydrogen Chemical class 0.000 claims 43
- 125000000623 heterocyclic group Chemical group 0.000 claims 40
- 125000003118 aryl group Chemical group 0.000 claims 38
- 125000001188 haloalkyl group Chemical group 0.000 claims 38
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 26
- 150000002367 halogens Chemical class 0.000 claims 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims 21
- 125000004452 carbocyclyl group Chemical group 0.000 claims 21
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 21
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 7
- 235000001014 amino acid Nutrition 0.000 claims 7
- 150000001413 amino acids Chemical class 0.000 claims 7
- 125000004474 heteroalkylene group Chemical group 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000005647 linker group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 238000006467 substitution reaction Methods 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229920001184 polypeptide Polymers 0.000 claims 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 229960000575 trastuzumab Drugs 0.000 claims 2
- RTQWWZBSTRGEAV-PKHIMPSTSA-N 2-[[(2s)-2-[bis(carboxymethyl)amino]-3-[4-(methylcarbamoylamino)phenyl]propyl]-[2-[bis(carboxymethyl)amino]propyl]amino]acetic acid Chemical compound CNC(=O)NC1=CC=C(C[C@@H](CN(CC(C)N(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 RTQWWZBSTRGEAV-PKHIMPSTSA-N 0.000 claims 1
- 230000004568 DNA-binding Effects 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 101001046686 Homo sapiens Integrin alpha-M Proteins 0.000 claims 1
- 102100022338 Integrin alpha-M Human genes 0.000 claims 1
- 102100022337 Integrin alpha-V Human genes 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 claims 1
- 108091005804 Peptidases Proteins 0.000 claims 1
- 239000004365 Protease Substances 0.000 claims 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 1
- 108060008539 Transglutaminase Proteins 0.000 claims 1
- 102000004243 Tubulin Human genes 0.000 claims 1
- 108090000704 Tubulin Proteins 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 108010048673 Vitronectin Receptors Proteins 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- 229960000548 alemtuzumab Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229960000397 bevacizumab Drugs 0.000 claims 1
- 230000027455 binding Effects 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 229960005395 cetuximab Drugs 0.000 claims 1
- 235000013477 citrulline Nutrition 0.000 claims 1
- 229960002173 citrulline Drugs 0.000 claims 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229960001776 edrecolomab Drugs 0.000 claims 1
- 229960000578 gemtuzumab Drugs 0.000 claims 1
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 claims 1
- 229960001001 ibritumomab tiuxetan Drugs 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- 229960005386 ipilimumab Drugs 0.000 claims 1
- 235000018977 lysine Nutrition 0.000 claims 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
- 229960002450 ofatumumab Drugs 0.000 claims 1
- 229960001972 panitumumab Drugs 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 235000008729 phenylalanine Nutrition 0.000 claims 1
- 229960004641 rituximab Drugs 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 claims 1
- 229960005267 tositumomab Drugs 0.000 claims 1
- 102000003601 transglutaminase Human genes 0.000 claims 1
- 210000004881 tumor cell Anatomy 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
- 235000014393 valine Nutrition 0.000 claims 1
- 0 CC(*)(CCCC1)N1I Chemical compound CC(*)(CCCC1)N1I 0.000 description 22
- VQHJVAWAAIBFDA-UHFFFAOYSA-N CC1(C(N)=O)N(C)CC1 Chemical compound CC1(C(N)=O)N(C)CC1 VQHJVAWAAIBFDA-UHFFFAOYSA-N 0.000 description 3
- YBXZWRDKSPJABR-UHFFFAOYSA-N CN(CC(C1)C2)C12C(N)=O Chemical compound CN(CC(C1)C2)C12C(N)=O YBXZWRDKSPJABR-UHFFFAOYSA-N 0.000 description 2
- FPIAJHVSWSKJNN-OQHSHRKDSA-N CC(C)C(C)(CC1(CC1)c1nc(CCC=O)c[s]1)N(C)C(C[C@H](C)C=C)=O Chemical compound CC(C)C(C)(CC1(CC1)c1nc(CCC=O)c[s]1)N(C)C(C[C@H](C)C=C)=O FPIAJHVSWSKJNN-OQHSHRKDSA-N 0.000 description 1
- NRGFWLUSLLUZCE-UHFFFAOYSA-N CC(CC1(CC1)C(OC)=O)(Cc1ccccc1)NC Chemical compound CC(CC1(CC1)C(OC)=O)(Cc1ccccc1)NC NRGFWLUSLLUZCE-UHFFFAOYSA-N 0.000 description 1
- HKNLQQZZSNXZEW-UHFFFAOYSA-N CC(CCCCCCNC)C(N)=O Chemical compound CC(CCCCCCNC)C(N)=O HKNLQQZZSNXZEW-UHFFFAOYSA-N 0.000 description 1
- PXHHIBMOFPCBJQ-UHFFFAOYSA-N CC1N(C)CCC1 Chemical compound CC1N(C)CCC1 PXHHIBMOFPCBJQ-UHFFFAOYSA-N 0.000 description 1
- JQUJXODGHDHZHP-VHRDTHDHSA-N CCCC(C(N(C)[C@](C)(CCc1nc(C(NC(C)(CCCCCC(O)=O)Cc2ccccc2)=O)c[s]1)C(C)C)=O)NC(C1(C2)N(C)CC2C1)=O Chemical compound CCCC(C(N(C)[C@](C)(CCc1nc(C(NC(C)(CCCCCC(O)=O)Cc2ccccc2)=O)c[s]1)C(C)C)=O)NC(C1(C2)N(C)CC2C1)=O JQUJXODGHDHZHP-VHRDTHDHSA-N 0.000 description 1
- NVIBWMLZIJEWSO-UHFFFAOYSA-N CCCCC(N(C)C(C)(CC1(CC1)c1nc(C(NC(CC2(CC2)C(O)=O)(C2)C2c2ccccc2)=O)c[s]1)C(C)=C)=O Chemical compound CCCCC(N(C)C(C)(CC1(CC1)c1nc(C(NC(CC2(CC2)C(O)=O)(C2)C2c2ccccc2)=O)c[s]1)C(C)=C)=O NVIBWMLZIJEWSO-UHFFFAOYSA-N 0.000 description 1
- WGUPSOGWIWRRCV-UHFFFAOYSA-N CCCCC(N(C)C1(CC(C2)(C2OC(C)=O)c2nc(C(NCCN(C=CC=C3)C3=O)=O)c[s]2)C(C)C1C)=O Chemical compound CCCCC(N(C)C1(CC(C2)(C2OC(C)=O)c2nc(C(NCCN(C=CC=C3)C3=O)=O)c[s]2)C(C)C1C)=O WGUPSOGWIWRRCV-UHFFFAOYSA-N 0.000 description 1
- MOXUNNDDVXNFJE-NANMCHNZSA-N CCCCC(N(C)C1(CC2(CC2)c2nc(C(N(C)[C@](CC3(CC3)C(O)=O)(C3)[C@@H]3c(cc3)ccc3NC(/C(/C)=C/CCC(CNC(CCCCCN(C(C=C3)=O)C3=[U])=O)=C)=O)=O)c[s]2)C(C)C1C)=O Chemical compound CCCCC(N(C)C1(CC2(CC2)c2nc(C(N(C)[C@](CC3(CC3)C(O)=O)(C3)[C@@H]3c(cc3)ccc3NC(/C(/C)=C/CCC(CNC(CCCCCN(C(C=C3)=O)C3=[U])=O)=C)=O)=O)c[s]2)C(C)C1C)=O MOXUNNDDVXNFJE-NANMCHNZSA-N 0.000 description 1
- JILOFHUHKRNIQZ-CFZVOKARSA-N CCCCC1OC1N(C)[C@](CC1(Cc2nc(C=O)c[s]2)CC1)(C1C)C1=C Chemical compound CCCCC1OC1N(C)[C@](CC1(Cc2nc(C=O)c[s]2)CC1)(C1C)C1=C JILOFHUHKRNIQZ-CFZVOKARSA-N 0.000 description 1
- WCGQAGFKKFVZNX-WFXWFVJPSA-N CC[C@@H](CC(N(C)C(C)(CC(C1)(C1NC(C)=O)c1nc(C(N[C@](CC2(CC2)C(O)O)(C2)C2c(cc2)ccc2N)=O)c[s]1)C(C)C)=O)C#C Chemical compound CC[C@@H](CC(N(C)C(C)(CC(C1)(C1NC(C)=O)c1nc(C(N[C@](CC2(CC2)C(O)O)(C2)C2c(cc2)ccc2N)=O)c[s]1)C(C)C)=O)C#C WCGQAGFKKFVZNX-WFXWFVJPSA-N 0.000 description 1
- IXRNKOGJSZAQGD-SACQWQMBSA-N CC[C@@H](CC(N(C)C(C)(CC(C1)(C1OC(C)=O)c1nc(C(N[C@H](CC2(CC2)C(O)OC)Cc2ccccc2)=O)c[s]1)C(C)C)=O)C(/[O]=C(\[C@@H](CC)N)/[C@H]1N(C)CCC1)=C Chemical compound CC[C@@H](CC(N(C)C(C)(CC(C1)(C1OC(C)=O)c1nc(C(N[C@H](CC2(CC2)C(O)OC)Cc2ccccc2)=O)c[s]1)C(C)C)=O)C(/[O]=C(\[C@@H](CC)N)/[C@H]1N(C)CCC1)=C IXRNKOGJSZAQGD-SACQWQMBSA-N 0.000 description 1
- MLVBTHCRAFNUKN-PUTITLFMSA-N CC[C@@H](CC(N(C)C1(CC(C2)(C2OC(C)NCC)c2nc(C(NC(C[C@H](C)C(O)=O)(C3)C3c(cc3)ccc3N)=O)c[s]2)C(C)C1C)=O)C#C Chemical compound CC[C@@H](CC(N(C)C1(CC(C2)(C2OC(C)NCC)c2nc(C(NC(C[C@H](C)C(O)=O)(C3)C3c(cc3)ccc3N)=O)c[s]2)C(C)C1C)=O)C#C MLVBTHCRAFNUKN-PUTITLFMSA-N 0.000 description 1
- IHTAIOVMHRVADT-RLGFOEBMSA-N CC[C@@H](CC(N(C)C1(CC(C2)([C@H]2OC(NCC)=O)c2nc(C(N[C@H](CC3(CC3)C(O)=O)Cc3ccccc3)=O)c[s]2)C(C)C1C)=O)C=C Chemical compound CC[C@@H](CC(N(C)C1(CC(C2)([C@H]2OC(NCC)=O)c2nc(C(N[C@H](CC3(CC3)C(O)=O)Cc3ccccc3)=O)c[s]2)C(C)C1C)=O)C=C IHTAIOVMHRVADT-RLGFOEBMSA-N 0.000 description 1
- IYFBVZNUIVEHDX-ZHVGMDMXSA-N CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(NC(C[C@H](C)C(OCC)=O)Cc2ccccc2)=O)c[s]1)OC(C)=O)C(C)C)=O)C/[O]=C(/[C@]1(C)N(C)CCC1)\N Chemical compound CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(NC(C[C@H](C)C(OCC)=O)Cc2ccccc2)=O)c[s]1)OC(C)=O)C(C)C)=O)C/[O]=C(/[C@]1(C)N(C)CCC1)\N IYFBVZNUIVEHDX-ZHVGMDMXSA-N 0.000 description 1
- OBSBCKGJCAUZEZ-KJYTXNCISA-N CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(NCCN(C=CC=C2)C2=O)=O)c[s]1)OC(C)=O)C(C)C)=O)C/[O]=C(/CCCCCNC)\N Chemical compound CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(NCCN(C=CC=C2)C2=O)=O)c[s]1)OC(C)=O)C(C)C)=O)C/[O]=C(/CCCCCNC)\N OBSBCKGJCAUZEZ-KJYTXNCISA-N 0.000 description 1
- AWMQJTGCTXBHEP-DCDJJNRNSA-N CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(N[C@H](C[C@H](C)C(O)=O)Cc(cc2)ccc2N)=O)c[s]1)OC(NCC)=O)C(C)C)=O)C/[O]=C(/C1(C)N(C)CCC1)\N Chemical compound CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(N[C@H](C[C@H](C)C(O)=O)Cc(cc2)ccc2N)=O)c[s]1)OC(NCC)=O)C(C)C)=O)C/[O]=C(/C1(C)N(C)CCC1)\N AWMQJTGCTXBHEP-DCDJJNRNSA-N 0.000 description 1
- KIVUKXPKKJQTPB-ZJHMJTSYSA-N CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(N[C@H](C[C@H](C)C(OC)=O)Cc2ccccc2)=O)c[s]1)NC(C)=O)C(C)C)=O)C/[O]=C(/C1(C)N(C)CCC1)\N Chemical compound CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(N[C@H](C[C@H](C)C(OC)=O)Cc2ccccc2)=O)c[s]1)NC(C)=O)C(C)C)=O)C/[O]=C(/C1(C)N(C)CCC1)\N KIVUKXPKKJQTPB-ZJHMJTSYSA-N 0.000 description 1
- INEZJIWMFZVJEF-YNXHRFJNSA-N CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(N[C@H](C[C@H](C)C(OC)=O)Cc2ccccc2)=O)c[s]1)OC(C)=O)C(C)C)=O)C/[O]=C(/C1(C2)N(C)CC2C1)\N Chemical compound CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(N[C@H](C[C@H](C)C(OC)=O)Cc2ccccc2)=O)c[s]1)OC(C)=O)C(C)C)=O)C/[O]=C(/C1(C2)N(C)CC2C1)\N INEZJIWMFZVJEF-YNXHRFJNSA-N 0.000 description 1
- JZLZKZCHKDGPGF-RWBPATOOSA-N CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(N[C@H](C[C@H](C)C(OC)=O)Cc2ccccc2)=O)c[s]1)OC(C)=O)C(C)C)=O)S Chemical compound CC[C@@H](CC(N(C)[C@H](C[C@H](c1nc(C(N[C@H](C[C@H](C)C(OC)=O)Cc2ccccc2)=O)c[s]1)OC(C)=O)C(C)C)=O)S JZLZKZCHKDGPGF-RWBPATOOSA-N 0.000 description 1
- ZDQYXNIOTQBEIB-DRXWIORDSA-N CC[C@H](C)CC(N(C)C(C[C@H](c1nc(C=O)c[s]1)OC(NCC)=O)C(C)C)=O Chemical compound CC[C@H](C)CC(N(C)C(C[C@H](c1nc(C=O)c[s]1)OC(NCC)=O)C(C)C)=O ZDQYXNIOTQBEIB-DRXWIORDSA-N 0.000 description 1
- YQFCPWVTUYQQIP-ODBNIMOWSA-N CC[C@H](C)CC(N(C)C1(CC(C2)(C2OC(NCC)=O)C2SC=C(C(NC(CC3(CC3)C(O)O)(C3)C3c(cc3)ccc3N)=O)N2)C(C)C1C)=O Chemical compound CC[C@H](C)CC(N(C)C1(CC(C2)(C2OC(NCC)=O)C2SC=C(C(NC(CC3(CC3)C(O)O)(C3)C3c(cc3)ccc3N)=O)N2)C(C)C1C)=O YQFCPWVTUYQQIP-ODBNIMOWSA-N 0.000 description 1
- HORJYEBQBIXJSD-UHFFFAOYSA-N CN(C)C1(CCCC1)C(N)=O Chemical compound CN(C)C1(CCCC1)C(N)=O HORJYEBQBIXJSD-UHFFFAOYSA-N 0.000 description 1
- BPXIEEUPEWZJFW-UHFFFAOYSA-N CN(CCC(C1)C2)C12C(N)=O Chemical compound CN(CCC(C1)C2)C12C(N)=O BPXIEEUPEWZJFW-UHFFFAOYSA-N 0.000 description 1
- MBFCVKUEHFIBER-UHFFFAOYSA-N CN(CCC1)C1(CC1)C1C(N)=O Chemical compound CN(CCC1)C1(CC1)C1C(N)=O MBFCVKUEHFIBER-UHFFFAOYSA-N 0.000 description 1
- JQVOTYIMEYIHPI-UHFFFAOYSA-N COC(C1(CC(C2)(C2C2C=CC=CC2)N)CC1)=O Chemical compound COC(C1(CC(C2)(C2C2C=CC=CC2)N)CC1)=O JQVOTYIMEYIHPI-UHFFFAOYSA-N 0.000 description 1
- JPGXUEFAQWNCEO-GZMMTYOYSA-N C[C@@H](C[C@H](Cc(cc1)ccc1N)N)C(O)=O Chemical compound C[C@@H](C[C@H](Cc(cc1)ccc1N)N)C(O)=O JPGXUEFAQWNCEO-GZMMTYOYSA-N 0.000 description 1
- YRSUAENJDFTTJH-UHFFFAOYSA-N NC(C1(CC2C3)N2C3CCC1)=O Chemical compound NC(C1(CC2C3)N2C3CCC1)=O YRSUAENJDFTTJH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662289485P | 2016-02-01 | 2016-02-01 | |
| US62/289,485 | 2016-02-01 | ||
| US201662322328P | 2016-04-14 | 2016-04-14 | |
| US62/322,328 | 2016-04-14 | ||
| PCT/IB2017/050462 WO2017134547A1 (en) | 2016-02-01 | 2017-01-27 | Tubulysin analogs and methods for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2019507126A JP2019507126A (ja) | 2019-03-14 |
| JP2019507126A5 true JP2019507126A5 (enExample) | 2020-02-20 |
Family
ID=57963390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018539095A Pending JP2019507126A (ja) | 2016-02-01 | 2017-01-27 | ツブリシン類似体およびこれらの調製のための方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US10723727B2 (enExample) |
| EP (1) | EP3411371A1 (enExample) |
| JP (1) | JP2019507126A (enExample) |
| CA (1) | CA3012960A1 (enExample) |
| WO (1) | WO2017134547A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11274124B2 (en) | 2017-11-29 | 2022-03-15 | William Marsh Rice University | Tubulysin analogues as anticancer agents and payloads for antibody-drug conjugates and methods of treatment therewith |
| WO2020132658A2 (en) | 2018-12-21 | 2020-06-25 | Regeneron Pharmaceuticals, Inc. | Tubulysins and protein-tubulysin conjugates |
| CN115867563B (zh) * | 2020-06-24 | 2025-06-27 | 里珍纳龙药品有限公司 | 微管溶素及蛋白质-微管溶素偶联物 |
| WO2023129518A1 (en) * | 2021-12-29 | 2023-07-06 | Regeneron Pharmaceuticals, Inc. | Tubulysins and protein-tubulysin conjugates |
| CN114920749B (zh) * | 2022-06-02 | 2024-08-16 | 山东鲁抗医药股份有限公司 | 7-氮杂双环[2.2.1]庚烷衍生物溴化物中间体的制备方法 |
| WO2025078841A2 (en) | 2023-10-11 | 2025-04-17 | Antikor Biopharma Limited | Antibodies, conjugates, and uses thereof |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL29945A (en) | 1968-05-06 | 1973-08-29 | Assia Chemical Labor Ltd | Beta-hydrazino carboxylic acids and processes for their preparation |
| GB2036891B (en) | 1978-12-05 | 1983-05-05 | Windsor Smith C | Change speed gear |
| GB8308235D0 (en) | 1983-03-25 | 1983-05-05 | Celltech Ltd | Polypeptides |
| US4816567A (en) | 1983-04-08 | 1989-03-28 | Genentech, Inc. | Recombinant immunoglobin preparations |
| JPS6147500A (ja) | 1984-08-15 | 1986-03-07 | Res Dev Corp Of Japan | キメラモノクロ−ナル抗体及びその製造法 |
| EP0173494A3 (en) | 1984-08-27 | 1987-11-25 | The Board Of Trustees Of The Leland Stanford Junior University | Chimeric receptors by dna splicing and expression |
| GB8422238D0 (en) | 1984-09-03 | 1984-10-10 | Neuberger M S | Chimeric proteins |
| JPS61134325A (ja) | 1984-12-04 | 1986-06-21 | Teijin Ltd | ハイブリツド抗体遺伝子の発現方法 |
| AU606320B2 (en) | 1985-11-01 | 1991-02-07 | International Genetic Engineering, Inc. | Modular assembly of antibody genes, antibodies prepared thereby and use |
| US5225539A (en) | 1986-03-27 | 1993-07-06 | Medical Research Council | Recombinant altered antibodies and methods of making altered antibodies |
| US5530101A (en) | 1988-12-28 | 1996-06-25 | Protein Design Labs, Inc. | Humanized immunoglobulins |
| DE3920358A1 (de) | 1989-06-22 | 1991-01-17 | Behringwerke Ag | Bispezifische und oligospezifische, mono- und oligovalente antikoerperkonstrukte, ihre herstellung und verwendung |
| CA2089661C (en) | 1990-08-29 | 2007-04-03 | Nils Lonberg | Transgenic non-human animals capable of producing heterologous antibodies |
| US5545806A (en) | 1990-08-29 | 1996-08-13 | Genpharm International, Inc. | Ransgenic non-human animals for producing heterologous antibodies |
| US5661016A (en) | 1990-08-29 | 1997-08-26 | Genpharm International Inc. | Transgenic non-human animals capable of producing heterologous antibodies of various isotypes |
| US5625126A (en) | 1990-08-29 | 1997-04-29 | Genpharm International, Inc. | Transgenic non-human animals for producing heterologous antibodies |
| US5633425A (en) | 1990-08-29 | 1997-05-27 | Genpharm International, Inc. | Transgenic non-human animals capable of producing heterologous antibodies |
| EP1136556B1 (en) | 1991-11-25 | 2005-06-08 | Enzon, Inc. | Method of producing multivalent antigen-binding proteins |
| US6214345B1 (en) | 1993-05-14 | 2001-04-10 | Bristol-Myers Squibb Co. | Lysosomal enzyme-cleavable antitumor drug conjugates |
| AU728657B2 (en) | 1996-03-18 | 2001-01-18 | Board Of Regents, The University Of Texas System | Immunoglobulin-like domains with increased half-lives |
| EP2292248A3 (en) | 2005-03-03 | 2011-06-29 | CovX Technologies Ireland Limited | Anti-angiogenic compounds |
| CA2723671C (en) * | 2007-05-10 | 2018-06-19 | R & D Biopharmaceuticals Gmbh | Tubulysine derivatives |
| US8883832B2 (en) | 2009-07-06 | 2014-11-11 | Aerpio Therapeutics Inc. | Compounds, compositions, and methods for preventing metastasis of cancer cells |
| US8394922B2 (en) | 2009-08-03 | 2013-03-12 | Medarex, Inc. | Antiproliferative compounds, conjugates thereof, methods therefor, and uses thereof |
| WO2012059882A2 (en) | 2010-11-05 | 2012-05-10 | Rinat Neuroscience Corporation | Engineered polypeptide conjugates and methods for making thereof using transglutaminase |
| SA112330989B1 (ar) | 2011-11-17 | 2015-07-07 | فايزر انك | ببتيدات سامة للخلايا ومواد اقتران جسم مضاد وعقار منها |
| EP2794653B1 (en) | 2011-12-23 | 2019-03-13 | Pfizer Inc | Engineered antibody constant regions for site-specific conjugation and methods and uses therefor |
| JP6133431B2 (ja) | 2012-11-24 | 2017-05-24 | ハンジョウ ディーエーシー バイオテック シーオー．，エルティディ．Ｈａｎｇｚｈｏｕ Ｄａｃ Ｂｉｏｔｅｃｈ Ｃｏ．，Ｌｔｄ． | 親水性連結体及び薬物分子と細胞結合分子との共役反応における親水性連結体の使用 |
| US10195289B2 (en) | 2013-07-31 | 2019-02-05 | Rinat Neuroscience Corp. | Engineered polypeptide conjugates using transglutaminase |
| US10183970B2 (en) * | 2014-01-28 | 2019-01-22 | Tube Pharmaceuticals Gmbh | Cytotoxic tubulysin compounds for conjugation |
| KR20160142392A (ko) * | 2014-04-11 | 2016-12-12 | 메디뮨 엘엘씨 | 튜부리신 유도체 |
| BR112016022910A2 (pt) | 2014-04-11 | 2017-10-17 | Medimmune Llc | anticorpos contra her2 biespecíficos |
-
2017
- 2017-01-27 JP JP2018539095A patent/JP2019507126A/ja active Pending
- 2017-01-27 US US16/072,291 patent/US10723727B2/en active Active
- 2017-01-27 CA CA3012960A patent/CA3012960A1/en not_active Abandoned
- 2017-01-27 WO PCT/IB2017/050462 patent/WO2017134547A1/en not_active Ceased
- 2017-01-27 EP EP17703229.9A patent/EP3411371A1/en not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019507126A5 (enExample) | ||
| JP7637431B2 (ja) | 分岐連結体を備えたチューブリシン類縁体の共役体 | |
| JP6715888B2 (ja) | 抗体−薬物コンジュゲート | |
| JP7073266B2 (ja) | Ｐｅｇ化薬物リンカー及びその中間体を調製するためのプロセス | |
| CN109912683B (zh) | 一种细胞毒素分子、偶联物及其制备方法和应用 | |
| AU2019455069B2 (en) | A conjugate of a cytotoxic agent to a cell binding molecule with branched linkers | |
| CA3107417C (en) | Effective method for manufacturing antibody-drug conjugate | |
| JP2021506883A (ja) | ピロロベンゾジアゼピン抗体結合体 | |
| JP2021503450A5 (enExample) | ||
| JP2021521111A (ja) | カンプトテシンペプチドコンジュゲート | |
| HRP20250345T1 (hr) | Konjugati antitijelo - lijek derivata cikličnih dinukleotida | |
| JP2020531471A5 (enExample) | ||
| EP2910573A1 (en) | Antibody-drug conjugate produced by binding through linker having hydrophilic structure | |
| RU2014116878A (ru) | Цитотоксические пептиды и их конъюгаты антитело-лекарственное средство | |
| JP2015535004A5 (enExample) | ||
| KR20210030394A (ko) | 가교-결합된 피롤로벤조다이아제핀 이량체(pbd) 유도체 및 이의 접합체 | |
| HU229055B1 (hu) | Kombretasztatin A-4-foszfát prodrug nitrogént tartalmazó vegyületekkel alkotott sói | |
| JP2024028815A (ja) | チューブリシン類縁体と細胞結合分子との共役体の製剤 | |
| JP2012516896A5 (enExample) | ||
| JP2017518304A5 (enExample) | ||
| HRP20200032T1 (hr) | Antitijelo lijek konjugati | |
| RU2015115954A (ru) | Аналоги сплицеостатина | |
| TWI785334B (zh) | 一種細胞結合分子-tubulysin衍生物偶聯物及其製備方法 | |
| JP2018123122A5 (enExample) | ||
| JP2020500148A (ja) | 新規細胞傷害性剤およびそのコンジュゲート |