JP2015508074A5 - - Google Patents
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- JP2015508074A5 JP2015508074A5 JP2014556700A JP2014556700A JP2015508074A5 JP 2015508074 A5 JP2015508074 A5 JP 2015508074A5 JP 2014556700 A JP2014556700 A JP 2014556700A JP 2014556700 A JP2014556700 A JP 2014556700A JP 2015508074 A5 JP2015508074 A5 JP 2015508074A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- nhr
- nhc
- alkyl
- 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
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- 150000001875 compounds Chemical class 0.000 claims 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000006850 spacer group Chemical group 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 3
- 239000004475 Arginine Substances 0.000 claims 3
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 3
- 239000004471 Glycine Substances 0.000 claims 3
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 3
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 3
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 3
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 3
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 3
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 3
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 claims 3
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 3
- 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 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 3
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 3
- 239000004472 Lysine Substances 0.000 claims 3
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 claims 3
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 3
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 3
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 3
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 3
- 239000004473 Threonine Substances 0.000 claims 3
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 3
- 235000004279 alanine Nutrition 0.000 claims 3
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 3
- 235000008206 alpha-amino acids Nutrition 0.000 claims 3
- 239000000427 antigen Substances 0.000 claims 3
- 102000036639 antigens Human genes 0.000 claims 3
- 108091007433 antigens Proteins 0.000 claims 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 3
- 235000009697 arginine Nutrition 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000000732 arylene group Chemical group 0.000 claims 3
- 235000009582 asparagine Nutrition 0.000 claims 3
- 229960001230 asparagine Drugs 0.000 claims 3
- 235000003704 aspartic acid Nutrition 0.000 claims 3
- 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 3
- 235000013477 citrulline Nutrition 0.000 claims 3
- 229960002173 citrulline Drugs 0.000 claims 3
- 235000018417 cysteine Nutrition 0.000 claims 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- 235000013922 glutamic acid Nutrition 0.000 claims 3
- 239000004220 glutamic acid Substances 0.000 claims 3
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 3
- 235000004554 glutamine Nutrition 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000005549 heteroarylene group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 3
- 229960000310 isoleucine Drugs 0.000 claims 3
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 3
- 229930182817 methionine Natural products 0.000 claims 3
- 229960003104 ornithine Drugs 0.000 claims 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 3
- 125000005717 substituted cycloalkylene group Chemical group 0.000 claims 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 3
- 239000004474 valine Substances 0.000 claims 3
- 210000004027 cell Anatomy 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- -1 azido, hydroxyl amino Chemical group 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- ZPWOOKQUDFIEIX-UHFFFAOYSA-N cyclooctyne Chemical compound C1CCCC#CCC1 ZPWOOKQUDFIEIX-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000008685 targeting Effects 0.000 claims 1
- 210000004881 tumor cell Anatomy 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261598143P | 2012-02-13 | 2012-02-13 | |
| US61/598,143 | 2012-02-13 | ||
| US201261653785P | 2012-05-31 | 2012-05-31 | |
| US61/653,785 | 2012-05-31 | ||
| PCT/US2013/025247 WO2013122823A1 (en) | 2012-02-13 | 2013-02-08 | Enediyne compounds, conjugates thereof, and uses and methods therefor |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015508074A JP2015508074A (ja) | 2015-03-16 |
| JP2015508074A5 true JP2015508074A5 (enExample) | 2016-02-18 |
| JP6113194B2 JP6113194B2 (ja) | 2017-04-12 |
Family
ID=47722570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014556700A Expired - Fee Related JP6113194B2 (ja) | 2012-02-13 | 2013-02-08 | エンジイン化合物、その抱合体、ならびにその使用および方法 |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US8709431B2 (enExample) |
| EP (1) | EP2814829B1 (enExample) |
| JP (1) | JP6113194B2 (enExample) |
| KR (1) | KR101660146B1 (enExample) |
| CN (1) | CN104220441B (enExample) |
| AR (1) | AR089972A1 (enExample) |
| AU (1) | AU2013221873B2 (enExample) |
| BR (1) | BR112014019990A8 (enExample) |
| CA (1) | CA2864420C (enExample) |
| CL (1) | CL2014002096A1 (enExample) |
| CO (1) | CO7061078A2 (enExample) |
| CY (1) | CY1118899T1 (enExample) |
| DK (1) | DK2814829T3 (enExample) |
| EA (1) | EA027925B1 (enExample) |
| ES (1) | ES2615268T3 (enExample) |
| HK (1) | HK1204326A1 (enExample) |
| HR (1) | HRP20170334T1 (enExample) |
| HU (1) | HUE033704T2 (enExample) |
| IL (1) | IL233965B (enExample) |
| LT (1) | LT2814829T (enExample) |
| MX (1) | MX350539B (enExample) |
| PE (1) | PE20141791A1 (enExample) |
| PL (1) | PL2814829T3 (enExample) |
| PT (1) | PT2814829T (enExample) |
| RS (1) | RS55763B1 (enExample) |
| SG (1) | SG11201404667XA (enExample) |
| SI (1) | SI2814829T1 (enExample) |
| SM (1) | SMT201700137T1 (enExample) |
| TW (1) | TW201336851A (enExample) |
| WO (1) | WO2013122823A1 (enExample) |
| ZA (1) | ZA201406723B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO3407B1 (ar) | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
| SG11201601047SA (en) * | 2013-08-14 | 2016-03-30 | Univ Rice William M | Derivatives of uncialamycin, methods of synthesis and their use as antitumor agents |
| SG11201607818WA (en) | 2014-03-20 | 2016-10-28 | Bristol Myers Squibb Co | Stabilized fibronectin based scaffold molecules |
| SMT202000413T1 (it) | 2014-11-21 | 2020-09-10 | Bristol Myers Squibb Co | Anticorpi nei confronti di cd73 e loro usi |
| MX386942B (es) | 2014-11-21 | 2025-03-19 | Bristol Myers Squibb Co | Anticuerpos que comprenden regiones constantes pesadas modificadas. |
| AU2015353573B2 (en) | 2014-11-25 | 2020-09-03 | Bristol-Myers Squibb Company | Novel PD-L1 binding polypeptides for imaging |
| CN107531720A (zh) * | 2015-01-08 | 2018-01-02 | 斯克利普斯研究院 | 抗癌症候选药物 |
| EP3268048B1 (en) | 2015-03-10 | 2019-05-08 | Bristol-Myers Squibb Company | Antibodies conjugatable by transglutaminase and conjugates made therefrom |
| PT3303396T (pt) | 2015-05-29 | 2023-01-30 | Bristol Myers Squibb Co | Anticorpos contra ox40 e utilizações dos mesmos |
| JP6951340B2 (ja) | 2015-09-23 | 2021-10-20 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | グリピカン−３結合フィブロネクチンベース足場分子 |
| CN107029242A (zh) | 2015-11-03 | 2017-08-11 | 财团法人工业技术研究院 | 抗体药物复合物及其制造方法 |
| AU2016377371A1 (en) | 2015-12-21 | 2018-08-09 | Bristol-Myers Squibb Company | Variant antibodies for site-specific conjugation |
| KR20230038311A (ko) | 2016-03-04 | 2023-03-17 | 브리스톨-마이어스 스큅 컴퍼니 | 항-cd73 항체와의 조합 요법 |
| CN106267188B (zh) * | 2016-08-15 | 2025-06-17 | 深圳大学 | 小分子免疫激动剂偶联pd-1抗体的新型抗体及其在抗肿瘤中的应用 |
| 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 |
| 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 |
| JP7762498B2 (ja) | 2017-05-25 | 2025-10-30 | ブリストル－マイヤーズ スクイブ カンパニー | 修飾重鎖定常領域を含む抗体 |
| CN111683686A (zh) * | 2017-12-06 | 2020-09-18 | 西纳福克斯股份有限公司 | 烯二炔缀合物 |
| CN110183659B (zh) * | 2018-02-21 | 2022-04-26 | 香港科技大学 | 含有杂环的聚合物、其制备方法及其应用 |
| WO2020112781A1 (en) | 2018-11-28 | 2020-06-04 | Bristol-Myers Squibb Company | Antibodies comprising modified heavy constant regions |
| DK3886914T3 (da) | 2018-11-30 | 2023-07-03 | Bristol Myers Squibb Co | Antistof omfattende en glutaminholdig letkæde-c-terminal forlængelse, konjugater deraf og fremgangsmåder samt anvendelser |
| US12478686B2 (en) | 2018-12-12 | 2025-11-25 | Bristol-Myers Squibb Company | Antibodies modified for transglutaminase conjugation, conjugates thereof, and methods and uses |
| AU2020279478A1 (en) * | 2019-05-22 | 2021-12-09 | Board Of Regents, The University Of Texas System | Functionalized gold carbene naphthoquinone complexes for use in the treatment of cancer |
| US20240377413A1 (en) | 2019-09-16 | 2024-11-14 | Bristol-Myers Squibb Company | Dual capture method for analysis of antibody-drug conjugates |
| CA3223936A1 (en) | 2021-06-28 | 2023-01-05 | Ronald Christiaan Elgersma | Conjugates comprising phosphoantigens and their use in therapy |
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