JPWO2021019245A5 - - Google Patents
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- JPWO2021019245A5 JPWO2021019245A5 JP2022505581A JP2022505581A JPWO2021019245A5 JP WO2021019245 A5 JPWO2021019245 A5 JP WO2021019245A5 JP 2022505581 A JP2022505581 A JP 2022505581A JP 2022505581 A JP2022505581 A JP 2022505581A JP WO2021019245 A5 JPWO2021019245 A5 JP WO2021019245A5
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- Japan
- Prior art keywords
- cancer
- peptide ligand
- pharmaceutically acceptable
- alanine
- epha2
- Prior art date
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Description
本発明の特定の二環式ペプチドを上述の競合結合アッセイで試験した。結果は、表1に見られる:
表1:本発明の選択された二環式ペプチドの競合結合アッセイ
(態様1)
少なくとも2つのループ配列によって隔てられた少なくとも3つの反応基を含むポリペプチド及び該ポリペプチドの反応基と共有結合を形成する、1,1',1''-(1,3,5-トリアジナン-1,3,5-トリイル)トリプロパ-2-エン-1-オンである分子スキャフォールドを含み、その結果、少なくとも2つのポリペプチドループが該分子スキャフォールド上に形成される、EphA2に特異的なペプチドリガンドであって、該ペプチドリガンドが、
(化1)
(ここで、Acはアセチルを表し、HyPはヒドロキシプロリンを表し、HArgはホモアルギニンを表し、PYAは4-ペンチン酸を表し、3,3-DPAは3,3-ジフェニルアラニンを表し、Cbaはβ-シクロブチルアラニンを表し、1Nalは1-ナフチルアラニンを表し、NMeAlaはN-メチル-アラニンを表し、His1MeはN1-メチル-L-ヒスチジンを表し、His3MeはN3-メチル-L-ヒスチジンを表し、4ThiAzはβ-(4-チアゾリル)-アラニンを表し、Thiは2-チエニル-アラニンを表し、3Thiは3-チエニルアラニンを表し、パルミトイル-Glu-LysN
3
はN2-((S)-4-カルボキシ-4-パルミトアミドブタノイル)-N6-ジアゾ-L-リジン:
(化2)
を表し、pCoPheはパラ-カルボキシ-フェニルアラニンを表し、hGluはホモグルタミン酸を表し、B-Alaはβ-アラニンを表し、Sar
10
は10個のサルコシン単位を表し、Nleはノルロイシンを表し、かつ[MerPro]
i
、C
i
、C
ii
、C
iii
、及び[Cysam]
iii
は、システイン、3-メルカプトプロピオン酸(MerPro)、及びシステアミン(Cysam)から選択される第一(i)、第二(ii)、及び第三(iii)の反応基を表す)
:から選択されるアミノ酸配列、又はその医薬として許容し得る塩を含む、前記EphA2に特異的なペプチドリガンド。
(態様2)
(化3)
又はその医薬として許容し得る塩である、態様1記載のペプチドリガンド。
(態様3)
(化4)
又はその医薬として許容し得る塩である、態様1記載のペプチドリガンド。
(態様4)
前記医薬として許容し得る塩が、遊離酸又はナトリウム、カリウム、カルシウム、アンモニウム塩から選択される、態様1~3のいずれか一項記載のペプチドリガンド。
(態様5)
前記EphA2がヒトEphA2である、態様1~4のいずれか一項記載のペプチドリガンド。
(態様6)
態様1~5のいずれか一項記載のペプチドリガンドを1以上の医薬として許容し得る賦形剤との組合せで含む、医薬組成物。
(態様7)
罹患組織におけるEphA2の過剰発現を特徴とする疾患又は障害の予防、抑制、又は治療において使用するための、態様1~6のいずれか一項記載のペプチドリガンド。
(態様8)
癌の予防、抑制、又は治療において使用するための、態様1~7のいずれか一項記載のペプチドリガンド。
(態様9)
前記癌が、前立腺癌、肺癌(例えば、非小細胞肺癌(NSCLC))、乳癌(例えば、トリプルネガティブ乳癌)、胃癌、卵巣癌、食道癌、多発性骨髄腫、及び線維肉腫:から選択される、態様8記載の使用のためのペプチドリガンド。
Certain bicyclic peptides of the invention were tested in the competitive binding assay described above. The results are seen in Table 1:
Table 1: Competitive binding assay for selected bicyclic peptides of the invention.
(Aspect 1)
a polypeptide comprising at least three reactive groups separated by at least two loop sequences and a 1,1′,1″-(1,3,5-triazinane-) forming a covalent bond with the reactive group of said polypeptide; EphA2-specific peptide comprising a molecular scaffold that is 1,3,5-triyl)triprop-2-en-1-one, such that at least two polypeptide loops are formed on said molecular scaffold a ligand, the peptide ligand comprising:
(Chem. 1)
(where Ac represents acetyl, HyP represents hydroxyproline, HArg represents homoarginine, PYA represents 4-pentynoic acid, 3,3-DPA represents 3,3-diphenylalanine, Cba represents β-Cyclobutylalanine, 1Nal for 1-naphthylalanine, NMeAla for N-methyl-alanine, His1Me for N1-methyl-L-histidine, His3Me for N3-methyl-L-histidine , 4ThiAz represents β-(4-thiazolyl)-alanine, Thi represents 2-thienyl-alanine, 3Thi represents 3-thienylalanine, palmitoyl-Glu-LysN 3 represents N2-((S)-4- Carboxy-4-palmitamidobutanoyl)-N6-diazo-L-lysine:
(Chemical 2)
, pCoPhe represents para-carboxy-phenylalanine, hGlu represents homoglutamic acid, B-Ala represents β-alanine, Sar 10 represents 10 sarcosine units, Nle represents norleucine, and [MerPro ] i , C i , C ii , C iii , and [Cysam] iii are first (i), second (ii) selected from cysteine, 3-mercaptopropionic acid (MerPro), and cysteamine (Cysam); , and representing the third (iii) reactive group)
or a pharmaceutically acceptable salt thereof.
(Aspect 2)
(Chemical 3)
or a pharmaceutically acceptable salt thereof.
(Aspect 3)
(Chem. 4)
or a pharmaceutically acceptable salt thereof.
(Aspect 4)
4. The peptide ligand according to any one of embodiments 1-3, wherein said pharmaceutically acceptable salt is selected from the free acid or sodium, potassium, calcium, ammonium salts.
(Aspect 5)
5. The peptide ligand of any one of embodiments 1-4, wherein said EphA2 is human EphA2.
(Aspect 6)
A pharmaceutical composition comprising a peptide ligand according to any one of aspects 1-5 in combination with one or more pharmaceutically acceptable excipients.
(Aspect 7)
7. A peptide ligand according to any one of embodiments 1-6 for use in preventing, suppressing or treating a disease or disorder characterized by overexpression of EphA2 in affected tissue.
(Aspect 8)
A peptide ligand according to any one of aspects 1-7 for use in the prevention, suppression or treatment of cancer.
(Aspect 9)
said cancer is selected from: prostate cancer, lung cancer (e.g. non-small cell lung cancer (NSCLC)), breast cancer (e.g. triple negative breast cancer), gastric cancer, ovarian cancer, esophageal cancer, multiple myeloma, and fibrosarcoma. , a peptide ligand for use according to embodiment 8.
Applications Claiming Priority (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201962880191P | 2019-07-30 | 2019-07-30 | |
US62/880,191 | 2019-07-30 | ||
US201962910088P | 2019-10-03 | 2019-10-03 | |
US62/910,088 | 2019-10-03 | ||
US201962931442P | 2019-11-06 | 2019-11-06 | |
US62/931,442 | 2019-11-06 | ||
US202063022667P | 2020-05-11 | 2020-05-11 | |
US63/022,667 | 2020-05-11 | ||
US202063024715P | 2020-05-14 | 2020-05-14 | |
US63/024,715 | 2020-05-14 | ||
PCT/GB2020/051829 WO2021019245A1 (en) | 2019-07-30 | 2020-07-30 | BICYCLIC PEPTIDE LIGANDS SPECIFIC FOR EphA2 |
Publications (2)
Publication Number | Publication Date |
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JP2022542291A JP2022542291A (en) | 2022-09-30 |
JPWO2021019245A5 true JPWO2021019245A5 (en) | 2023-08-04 |
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JP2022506048A Pending JP2022544058A (en) | 2019-07-30 | 2020-07-30 | Heterotandem bicyclic peptide complexes |
JP2022505570A Pending JP2022542286A (en) | 2019-07-30 | 2020-07-30 | Heterotandem bicyclic peptide complexes |
JP2022505581A Pending JP2022542291A (en) | 2019-07-30 | 2020-07-30 | Bicyclic peptide ligands specific for EphA2 |
JP2022506077A Pending JP2022542386A (en) | 2019-07-30 | 2020-07-30 | Heterotandem bicyclic peptide complexes |
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JP2022506048A Pending JP2022544058A (en) | 2019-07-30 | 2020-07-30 | Heterotandem bicyclic peptide complexes |
JP2022505570A Pending JP2022542286A (en) | 2019-07-30 | 2020-07-30 | Heterotandem bicyclic peptide complexes |
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Country Status (12)
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US (6) | US11306123B2 (en) |
EP (4) | EP4003527A1 (en) |
JP (4) | JP2022544058A (en) |
KR (3) | KR20220049529A (en) |
CN (4) | CN114555626A (en) |
AU (3) | AU2020323739A1 (en) |
BR (3) | BR112022001520A2 (en) |
CA (3) | CA3147570A1 (en) |
IL (3) | IL290093A (en) |
MX (3) | MX2022001273A (en) |
TW (2) | TW202110485A (en) |
WO (4) | WO2021019244A1 (en) |
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