JP2019507126A5 - - Google Patents
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- 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
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- 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 (cg-RX-API-DMAC10.html) | 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 (cg-RX-API-DMAC10.html) |
| EP (1) | EP3411371A1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP2019507126A (cg-RX-API-DMAC10.html) |
| CA (1) | CA3012960A1 (cg-RX-API-DMAC10.html) |
| WO (1) | WO2017134547A1 (cg-RX-API-DMAC10.html) |
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 |
| MX2022015769A (es) * | 2020-06-24 | 2023-01-19 | Regeneron Pharma | Tubulisinas y conjugados de proteina-tubulisina. |
| 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 |
| IL327670A (en) | 2023-10-11 | 2026-06-01 | Antikor Biopharma Ltd | 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 |
| DE3689123T2 (de) | 1985-11-01 | 1994-03-03 | Xoma Corp | Modulare einheit von antikörpergenen, daraus hergestellte antikörper und verwendung. |
| 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 |
| US5625126A (en) | 1990-08-29 | 1997-04-29 | Genpharm International, Inc. | Transgenic non-human animals for producing heterologous antibodies |
| US5545806A (en) | 1990-08-29 | 1996-08-13 | Genpharm International, Inc. | Ransgenic non-human animals for producing heterologous antibodies |
| ES2246502T3 (es) | 1990-08-29 | 2006-02-16 | Genpharm International, Inc. | Animales no humanos transgenicos capaces de producir anticuerpos heterologos. |
| US5661016A (en) | 1990-08-29 | 1997-08-26 | Genpharm International Inc. | Transgenic non-human animals capable of producing heterologous antibodies of various isotypes |
| US5633425A (en) | 1990-08-29 | 1997-05-27 | Genpharm International, Inc. | Transgenic non-human animals capable of producing heterologous antibodies |
| DE69233528T2 (de) | 1991-11-25 | 2006-03-16 | Enzon, Inc. | Verfahren zur Herstellung von multivalenten antigenbindenden Proteinen |
| US6214345B1 (en) | 1993-05-14 | 2001-04-10 | Bristol-Myers Squibb Co. | Lysosomal enzyme-cleavable antitumor drug conjugates |
| CA2249195A1 (en) | 1996-03-18 | 1997-09-25 | Board Of Regents, The University Of Texas System | Immunoglobin-like domains with increased half lives |
| JP5167473B2 (ja) | 2005-03-03 | 2013-03-21 | コヴェックス・テクノロジーズ・アイルランド・リミテッド | 抗血管新生化合物 |
| EP2148886B1 (en) * | 2007-05-10 | 2014-02-19 | 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 |
| CA2813411C (en) | 2010-11-05 | 2016-08-02 | Rinat Neuroscience Corporation | Engineered polypeptide conjugates and methods for making thereof using transglutaminase |
| EP2780039B9 (en) | 2011-11-17 | 2018-04-18 | Pfizer Inc | Cytotoxic peptides and antibody drug conjugates thereof |
| EP3539982B1 (en) | 2011-12-23 | 2025-02-19 | Pfizer Inc. | Engineered antibody constant regions for site-specific conjugation and methods and uses therefor |
| US10131682B2 (en) | 2012-11-24 | 2018-11-20 | Hangzhou Dac Biotech Co., Ltd. | Hydrophilic linkers and their uses for conjugation of drugs to a cell binding molecules |
| US10195289B2 (en) | 2013-07-31 | 2019-02-05 | Rinat Neuroscience Corp. | Engineered polypeptide conjugates using transglutaminase |
| WO2015113760A1 (en) * | 2014-01-28 | 2015-08-06 | Tube Pharmaceuticals Gmbh | Cytotoxic tubulysin compounds for conjugation |
| CA2943299A1 (en) | 2014-04-11 | 2015-10-15 | Medimmune, Llc | Bispecific her2 antibodies |
| CA2945318A1 (en) * | 2014-04-11 | 2015-10-15 | Medimmune, Llc | Tubulysin derivatives |
-
2017
- 2017-01-27 CA CA3012960A patent/CA3012960A1/en not_active Abandoned
- 2017-01-27 US US16/072,291 patent/US10723727B2/en active Active
- 2017-01-27 EP EP17703229.9A patent/EP3411371A1/en not_active Withdrawn
- 2017-01-27 JP JP2018539095A patent/JP2019507126A/ja active Pending
- 2017-01-27 WO PCT/IB2017/050462 patent/WO2017134547A1/en not_active Ceased
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