JP2015535004A5 - - Google Patents
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- JP2015535004A5 JP2015535004A5 JP2015540238A JP2015540238A JP2015535004A5 JP 2015535004 A5 JP2015535004 A5 JP 2015535004A5 JP 2015540238 A JP2015540238 A JP 2015540238A JP 2015540238 A JP2015540238 A JP 2015540238A JP 2015535004 A5 JP2015535004 A5 JP 2015535004A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- nrr
- independently selected
- hydrogen
- group
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 160
- 229910052739 hydrogen Inorganic materials 0.000 claims 78
- 239000001257 hydrogen Substances 0.000 claims 76
- 150000002431 hydrogen Chemical class 0.000 claims 42
- 150000003839 salts Chemical class 0.000 claims 40
- 150000001875 compounds Chemical class 0.000 claims 37
- 125000000623 heterocyclic group Chemical group 0.000 claims 34
- 125000003118 aryl group Chemical group 0.000 claims 33
- 229910052736 halogen Inorganic materials 0.000 claims 31
- 150000002367 halogens Chemical class 0.000 claims 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 26
- 125000001424 substituent group Chemical group 0.000 claims 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 25
- 125000001072 heteroaryl group Chemical group 0.000 claims 21
- 125000004452 carbocyclyl group Chemical group 0.000 claims 20
- 229910052799 carbon Inorganic materials 0.000 claims 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 16
- 229910052760 oxygen Inorganic materials 0.000 claims 15
- 125000004429 atom Chemical group 0.000 claims 14
- 125000004432 carbon atom Chemical group C* 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 229910052717 sulfur Inorganic materials 0.000 claims 13
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 11
- 239000001301 oxygen Substances 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 150000002118 epoxides Chemical class 0.000 claims 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 9
- 235000001014 amino acid Nutrition 0.000 claims 9
- 150000001413 amino acids Chemical class 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 239000011593 sulfur Substances 0.000 claims 9
- 125000002947 alkylene group Chemical group 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000001118 alkylidene group Chemical group 0.000 claims 5
- 125000005647 linker group Chemical group 0.000 claims 4
- 229960000575 trastuzumab Drugs 0.000 claims 4
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- -1 and R 3 is Chemical group 0.000 claims 2
- 230000027455 binding Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 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
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- 239000004593 Epoxy Substances 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
- 102000008394 Immunoglobulin Fragments Human genes 0.000 claims 1
- 108010021625 Immunoglobulin Fragments 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
- 206010028980 Neoplasm Diseases 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
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 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
- 239000011230 binding agent Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 201000011510 cancer Diseases 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
- 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
- 229950007283 oregovomab Drugs 0.000 claims 1
- 229960001972 panitumumab Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 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
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 229960004641 rituximab Drugs 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
- 239000004474 valine Substances 0.000 claims 1
- 235000014393 valine Nutrition 0.000 claims 1
- 0 C[C@](*=C*(C)C)NC(C=CC(C)=O)=O Chemical compound C[C@](*=C*(C)C)NC(C=CC(C)=O)=O 0.000 description 4
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261722769P | 2012-11-05 | 2012-11-05 | |
| US61/722,769 | 2012-11-05 | ||
| US201261723645P | 2012-11-07 | 2012-11-07 | |
| US61/723,645 | 2012-11-07 | ||
| US201361829409P | 2013-05-31 | 2013-05-31 | |
| US61/829,409 | 2013-05-31 | ||
| PCT/IB2013/059553 WO2014068443A1 (en) | 2012-11-05 | 2013-10-22 | Spliceostatin analogs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015535004A JP2015535004A (ja) | 2015-12-07 |
| JP2015535004A5 true JP2015535004A5 (https=) | 2016-11-17 |
| JP6355641B2 JP6355641B2 (ja) | 2018-07-11 |
Family
ID=49958508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015540238A Active JP6355641B2 (ja) | 2012-11-05 | 2013-10-22 | スプライソスタチン類似体 |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US9169264B2 (https=) |
| EP (1) | EP2917195B9 (https=) |
| JP (1) | JP6355641B2 (https=) |
| KR (1) | KR101762047B1 (https=) |
| CN (1) | CN105121421B (https=) |
| AR (1) | AR093339A1 (https=) |
| AU (1) | AU2013340449B2 (https=) |
| BR (1) | BR112015010070B1 (https=) |
| CA (1) | CA2890569C (https=) |
| DK (1) | DK2917195T5 (https=) |
| ES (1) | ES2656298T3 (https=) |
| HU (1) | HUE036433T2 (https=) |
| IL (1) | IL238578B (https=) |
| MX (2) | MX340090B (https=) |
| PL (1) | PL2917195T3 (https=) |
| PT (1) | PT2917195T (https=) |
| RU (1) | RU2618523C2 (https=) |
| SI (1) | SI2917195T1 (https=) |
| TW (1) | TW201431846A (https=) |
| WO (1) | WO2014068443A1 (https=) |
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| CN113461705A (zh) * | 2013-11-19 | 2021-10-01 | 普渡研究基金会 | 抗癌剂及其制备 |
| TWI846009B (zh) * | 2013-12-19 | 2024-06-21 | 美商思進公司 | 與標的-藥物結合物併用之亞甲基胺基甲酸酯連接物 |
| JP6701077B2 (ja) * | 2013-12-19 | 2020-05-27 | シアトル ジェネティックス， インコーポレイテッド | 標的化薬物結合体と使用するためのメチレンカルバメートリンカー |
| CN106459055B (zh) | 2014-01-27 | 2019-11-01 | 辉瑞大药厂 | 双功能细胞毒类药剂 |
| US9840553B2 (en) | 2014-06-28 | 2017-12-12 | Kodiak Sciences Inc. | Dual PDGF/VEGF antagonists |
| ES2815353T3 (es) * | 2014-09-03 | 2021-03-29 | Immunogen Inc | Derivados de benzodiazepina citotóxicos |
| GB201416960D0 (en) * | 2014-09-25 | 2014-11-12 | Antikor Biopharma Ltd | Biological materials and uses thereof |
| KR20210013299A (ko) | 2014-10-17 | 2021-02-03 | 코디악 사이언시스 인코포레이티드 | 부티릴콜린에스테라제 양성이온성 중합체 컨쥬게이트 |
| CN107406496A (zh) * | 2015-03-10 | 2017-11-28 | 百时美施贵宝公司 | 可通过转谷氨酰胺酶缀合的抗体和由其制备的缀合物 |
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| GB2542391A (en) * | 2015-09-17 | 2017-03-22 | Annexin Pharmaceuticals Ab | Process of manufacture |
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| JP6486316B2 (ja) | 2015-11-03 | 2019-03-20 | 財團法人工業技術研究院Ｉｎｄｕｓｔｒｉａｌ Ｔｅｃｈｎｏｌｏｇｙ Ｒｅｓｅａｒｃｈ Ｉｎｓｔｉｔｕｔｅ | 抗体−薬物複合体（ａｄｃ）およびそれを形成するための方法 |
| KR102799807B1 (ko) * | 2015-12-30 | 2025-04-24 | 코디악 사이언시스 인코포레이티드 | 항체 및 이의 접합체 |
| EP3423105B1 (en) | 2016-03-02 | 2021-05-05 | Eisai R&D Management Co., Ltd. | Eribulin-based antibody-drug conjugates and methods of use |
| US11203588B2 (en) | 2016-03-10 | 2021-12-21 | The Regents Of The University Of California | Anti-cancer and splice modulating compounds and methods |
| AU2017277786A1 (en) * | 2016-06-08 | 2019-01-03 | William Marsh Rice University | Derivatives of Thailanstatin A, methods of treatment and methods of synthesis thereof |
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| JP7111722B2 (ja) * | 2016-09-23 | 2022-08-02 | パーデュー・リサーチ・ファウンデーション | 抗がん剤およびその調製方法 |
| EP3522933B1 (en) * | 2016-10-05 | 2021-12-15 | F. Hoffmann-La Roche AG | Methods for preparing antibody drug conjugates |
| TWI835714B (zh) | 2016-10-18 | 2024-03-21 | 美商思進公司 | 菸鹼醯胺腺嘌呤二核苷酸補救合成(salvage pathway)抑制劑之靶向投遞 |
| MX2019008773A (es) | 2017-01-24 | 2019-09-18 | Pfizer | Derivados de caliqueamicina y conjugados anticuerpo-farmaco de los mismos. |
| SG11201907887SA (en) | 2017-03-15 | 2019-09-27 | Eisai Co Ltd | Spliceosome mutations and uses thereof |
| WO2018201087A1 (en) | 2017-04-27 | 2018-11-01 | Seattle Genetics, Inc. | Quaternized nicotinamide adenine dinucleotide salvage pathway inhibitor conjugates |
| CN114885952B (zh) * | 2017-09-08 | 2024-07-23 | 马罗内生物创新公司 | 新型除草化合物 |
| IL273387B2 (en) | 2017-09-20 | 2023-10-01 | Ph Pharma Co Ltd | Thylanstatin analogs |
| WO2019109188A1 (en) * | 2017-12-06 | 2019-06-13 | Ontario Institute For Cancer Research (Oicr) | Acyl hydrazone linkers, methods and uses thereof |
| WO2019119141A1 (en) | 2017-12-22 | 2019-06-27 | Ontario Institute For Cancer Research (Oicr) | Heterocyclic acyl hydrazone linkers, methods and uses thereof |
| MX2020009152A (es) | 2018-03-02 | 2020-11-09 | Kodiak Sciences Inc | Anticuerpos de il-6 y constructos de fusion y conjugados de los mismos. |
| JOP20200268A1 (ar) | 2018-06-01 | 2020-10-26 | Eisai R&D Man Co Ltd | تضفير مترافقات عقار جسم مضاد معدل وطرق استخدامها |
| PE20211473A1 (es) * | 2018-12-13 | 2021-08-05 | Eisai Randd Man Co Ltd | Conjugados de anticuerpo-farmaco de herboxidieno y metodos de uso |
| CN109734627A (zh) * | 2019-03-04 | 2019-05-10 | 浙江华贝药业有限责任公司 | 一种新的化合物n-2-烷酰基-n-6-芴甲氧羰基-l-赖氨酸 |
| CN109761857A (zh) * | 2019-03-04 | 2019-05-17 | 浙江华贝药业有限责任公司 | N-2-棕榈酰基-n-6-芴甲氧羰基-l-赖氨酸的提纯方法 |
| CN109928895A (zh) * | 2019-03-04 | 2019-06-25 | 浙江华贝药业有限责任公司 | 一种n-2-烷酰基-n-6-芴甲氧羰基-l-赖氨酸的合成方法 |
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| US20230159552A1 (en) * | 2020-04-09 | 2023-05-25 | Bristol-Myers Squibb Company | Meayamycin and its analogues, methods for their preparation, and methods of use |
| WO2022256467A1 (en) * | 2021-06-02 | 2022-12-08 | The Charlotte Mecklenburg Hospital Authority D/B/A Atrium Health | Compositions and methods comprising deoxy-pentitols |
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| MX391454B (es) * | 2010-04-15 | 2025-03-05 | Seagen Inc | Compuesto de engarce-fármaco para conjugación a una unidad de ligando. |
| DK2528625T3 (da) * | 2010-04-15 | 2013-10-14 | Spirogen Sarl | Pyrrolobenzodiazepiner og konjugater deraf |
| JP2012086587A (ja) | 2010-10-15 | 2012-05-10 | Hitachi Ltd | 鉄道車両 |
| US9676871B2 (en) | 2010-11-05 | 2017-06-13 | Pfizer Inc. | Engineered polypeptide conjugates and methods for making thereof using transglutaminase |
| AU2012335205A1 (en) | 2011-11-11 | 2014-05-29 | Rinat Neuroscience Corp. | Antibodies specific for Trop-2 and their uses |
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