JPWO2022155704A5 - - Google Patents
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- Publication number
- JPWO2022155704A5 JPWO2022155704A5 JP2023543460A JP2023543460A JPWO2022155704A5 JP WO2022155704 A5 JPWO2022155704 A5 JP WO2022155704A5 JP 2023543460 A JP2023543460 A JP 2023543460A JP 2023543460 A JP2023543460 A JP 2023543460A JP WO2022155704 A5 JPWO2022155704 A5 JP WO2022155704A5
- Authority
- JP
- Japan
- Prior art keywords
- alanine
- amino acid
- methionine
- bicyclic
- peptidomimetic
- 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
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 31
- 235000004279 alanine Nutrition 0.000 claims 31
- 150000001413 amino acids Chemical group 0.000 claims 27
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 24
- 235000001014 amino acid Nutrition 0.000 claims 24
- 229940024606 amino acid Drugs 0.000 claims 24
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 18
- 229930182817 methionine Natural products 0.000 claims 18
- 235000006109 methionine Nutrition 0.000 claims 18
- 108010074708 B7-H1 Antigen Proteins 0.000 claims 15
- 102000008096 B7-H1 Antigen Human genes 0.000 claims 15
- 125000002619 bicyclic group Chemical group 0.000 claims 13
- 239000000816 peptidomimetic Substances 0.000 claims 13
- 239000004471 Glycine Substances 0.000 claims 12
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 12
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 12
- 239000004474 valine Substances 0.000 claims 12
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 10
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 10
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 10
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 10
- 239000004475 Arginine Substances 0.000 claims 8
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 8
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 8
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 8
- 238000000034 method Methods 0.000 claims 7
- 108090000765 processed proteins & peptides Proteins 0.000 claims 7
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 6
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 6
- 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 6
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 6
- 239000004473 Threonine Substances 0.000 claims 6
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 6
- 125000000539 amino acid group Chemical group 0.000 claims 6
- 229960000310 isoleucine Drugs 0.000 claims 6
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 6
- 230000007935 neutral effect Effects 0.000 claims 6
- 238000006467 substitution reaction Methods 0.000 claims 6
- 150000008574 D-amino acids Chemical group 0.000 claims 5
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 5
- 239000004472 Lysine Substances 0.000 claims 5
- 235000018977 lysine Nutrition 0.000 claims 5
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 4
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 4
- 235000003704 aspartic acid Nutrition 0.000 claims 4
- 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 4
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims 4
- 239000002062 molecular scaffold Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 3
- 238000012986 modification Methods 0.000 claims 3
- 230000004048 modification Effects 0.000 claims 3
- 229920001184 polypeptide Polymers 0.000 claims 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 2
- GHITVUOBZBZMND-UHFFFAOYSA-N 1,3,5-tris(bromomethyl)benzene Chemical compound BrCC1=CC(CBr)=CC(CBr)=C1 GHITVUOBZBZMND-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- 102000020313 Cell-Penetrating Peptides Human genes 0.000 claims 2
- 108010051109 Cell-Penetrating Peptides Proteins 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 102000011781 Karyopherins Human genes 0.000 claims 2
- 108010062228 Karyopherins Proteins 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 150000002632 lipids Chemical class 0.000 claims 2
- 239000002105 nanoparticle Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
- 150000008575 L-amino acids Chemical group 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims 1
- 235000021360 Myristic acid Nutrition 0.000 claims 1
- 238000007126 N-alkylation reaction Methods 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 210000004899 c-terminal region Anatomy 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 125000003636 chemical group Chemical group 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229930195712 glutamate Natural products 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000030648 nucleus localization Effects 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000012070 reactive reagent Substances 0.000 claims 1
- 125000006850 spacer group Chemical group 0.000 claims 1
- 238000011191 terminal modification Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2021900114A AU2021900114A0 (en) | 2021-01-19 | Novel bicyclic peptipes | |
| AU2021900114 | 2021-01-19 | ||
| PCT/AU2022/050023 WO2022155704A1 (en) | 2021-01-19 | 2022-01-19 | Novel bicyclic peptides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2024504136A JP2024504136A (ja) | 2024-01-30 |
| JP2024504136A5 JP2024504136A5 (https=) | 2025-01-27 |
| JPWO2022155704A5 true JPWO2022155704A5 (https=) | 2025-01-27 |
Family
ID=82548163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023543460A Pending JP2024504136A (ja) | 2021-01-19 | 2022-01-19 | 「新規な二環式ペプチド」 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20240117005A1 (https=) |
| EP (1) | EP4281486A4 (https=) |
| JP (1) | JP2024504136A (https=) |
| KR (1) | KR20230146025A (https=) |
| CN (1) | CN117062842A (https=) |
| AU (1) | AU2022209878A1 (https=) |
| CA (1) | CA3208598A1 (https=) |
| IL (1) | IL304545A (https=) |
| WO (1) | WO2022155704A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN121108243A (zh) * | 2025-01-03 | 2025-12-12 | 中国药科大学 | 一种非核糖体多肽化合物及其合成基因簇bnp37和应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1452868A2 (en) * | 2003-02-27 | 2004-09-01 | Pepscan Systems B.V. | Method for selecting a candidate drug compound |
| US10585100B2 (en) * | 2015-04-30 | 2020-03-10 | Kyoto University | Method of predicting effect of treatment by PD-1/PD-L1 blockade using abnormality of PD-L1 (CD274) as index |
| WO2017072280A1 (en) * | 2015-10-30 | 2017-05-04 | Affibody Ab | New polypeptide having affinity to pd-l1 |
| WO2018115203A1 (en) * | 2016-12-23 | 2018-06-28 | Bicyclerd Limited | Peptide derivatives having novel linkage structures |
| CN111936509A (zh) * | 2018-01-15 | 2020-11-13 | 艾比克斯治疗私人有限公司 | 蛋白质分子及其用途 |
| JP2019189591A (ja) * | 2018-04-27 | 2019-10-31 | 日東電工株式会社 | ヒトｐｄ−ｌ１結合性ペプチド |
| US12551567B2 (en) * | 2018-12-21 | 2026-02-17 | Bicyclerd Limited | Bicyclic peptide ligands specific for PD-L1 |
-
2022
- 2022-01-19 KR KR1020237027582A patent/KR20230146025A/ko active Pending
- 2022-01-19 CA CA3208598A patent/CA3208598A1/en active Pending
- 2022-01-19 EP EP22741955.3A patent/EP4281486A4/en active Pending
- 2022-01-19 AU AU2022209878A patent/AU2022209878A1/en active Pending
- 2022-01-19 JP JP2023543460A patent/JP2024504136A/ja active Pending
- 2022-01-19 CN CN202280022296.XA patent/CN117062842A/zh active Pending
- 2022-01-19 US US18/273,200 patent/US20240117005A1/en active Pending
- 2022-01-19 WO PCT/AU2022/050023 patent/WO2022155704A1/en not_active Ceased
-
2023
- 2023-07-18 IL IL304545A patent/IL304545A/en unknown
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