JP2019523782A5 - - Google Patents
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- JP2019523782A5 JP2019523782A5 JP2019514855A JP2019514855A JP2019523782A5 JP 2019523782 A5 JP2019523782 A5 JP 2019523782A5 JP 2019514855 A JP2019514855 A JP 2019514855A JP 2019514855 A JP2019514855 A JP 2019514855A JP 2019523782 A5 JP2019523782 A5 JP 2019523782A5
- Authority
- JP
- Japan
- Prior art keywords
- synthetic compound
- residue
- compound according
- peptide
- formylmethionine
- 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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- 108090000765 processed proteins & peptides Proteins 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000011230 binding agent Substances 0.000 claims description 44
- 239000012636 effector Substances 0.000 claims description 38
- PYUSHNKNPOHWEZ-YFKPBYRVSA-N N-formyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC=O PYUSHNKNPOHWEZ-YFKPBYRVSA-N 0.000 claims description 26
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 claims description 13
- 239000012634 fragment Substances 0.000 claims description 11
- 102000006495 integrins Human genes 0.000 claims description 11
- 108010044426 integrins Proteins 0.000 claims description 11
- 150000001413 amino acids Chemical group 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical group OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 9
- 125000000539 amino acid group Chemical group 0.000 claims description 9
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 5
- 108091023037 Aptamer Proteins 0.000 claims description 4
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 4
- 239000004473 Threonine Substances 0.000 claims description 4
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical group CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical group CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000556 agonist Substances 0.000 claims description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical group OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 3
- 239000004474 valine Chemical group 0.000 claims description 3
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 2
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 3
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- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 4
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- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 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 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000003399 chemotactic effect Effects 0.000 description 1
- PRQROPMIIGLWRP-BZSNNMDCSA-N chemotactic peptide Chemical compound CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 PRQROPMIIGLWRP-BZSNNMDCSA-N 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 210000003714 granulocyte Anatomy 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1609083.9 | 2016-05-24 | ||
| GBGB1609083.9A GB201609083D0 (en) | 2016-05-24 | 2016-05-24 | Synthetic compound |
| PCT/EP2017/062576 WO2017202933A1 (en) | 2016-05-24 | 2017-05-24 | Synthetic compound |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019523782A JP2019523782A (ja) | 2019-08-29 |
| JP2019523782A5 true JP2019523782A5 (https=) | 2021-12-09 |
| JP7449091B2 JP7449091B2 (ja) | 2024-03-13 |
Family
ID=56369849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019514855A Active JP7449091B2 (ja) | 2016-05-24 | 2017-05-24 | 合成化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US11318208B2 (https=) |
| EP (1) | EP3464334A1 (https=) |
| JP (1) | JP7449091B2 (https=) |
| CN (1) | CN109641943A (https=) |
| GB (1) | GB201609083D0 (https=) |
| WO (1) | WO2017202933A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201609083D0 (en) * | 2016-05-24 | 2016-07-06 | Syntab Therapeutics Gmbh | Synthetic compound |
| CN115466306B (zh) * | 2022-01-25 | 2025-06-27 | 香港中文大学（深圳） | 一种靶向细胞膜表面甲酰肽受体的多肽、药物组合物及其应用 |
| WO2025262329A1 (en) | 2024-06-21 | 2025-12-26 | Syntab Therapeutics Gmbh | Synthetic molecules comprising tlr2 ligands |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1055932A (en) | 1975-10-22 | 1979-06-05 | Hematech Inc. | Blood substitute based on hemoglobin |
| IT1164225B (it) | 1983-05-13 | 1987-04-08 | Anic Spa | Analoghi retro-invertiti del pentapeptide potenziante la bradichina bpp5a e metodi per la loro preparazione |
| US5328899A (en) | 1988-07-15 | 1994-07-12 | The Salk Institute For Biological Studies | NPY peptide analogs |
| US5767078A (en) | 1995-06-07 | 1998-06-16 | Johnson; Dana L. | Agonist peptide dimers |
| CA2223833C (en) | 1995-06-07 | 2010-12-21 | Nicholas C. Wrighton | Compounds and peptides that bind to the erythropoietin receptor |
| US6703480B1 (en) | 1999-11-24 | 2004-03-09 | Palani Balu | Peptide dimers as agonists of the erythropoientin (EPO) receptor, and associated methods of synthesis and use |
| AU2062601A (en) | 1999-12-06 | 2001-06-12 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | Peptides that stabilize protein antigens and enhance presentation to CD8+ T cells |
| CN1318084C (zh) | 2000-05-26 | 2007-05-30 | 奥索-麦克尼尔药品公司 | 神经保护肽 |
| WO2002055543A2 (en) | 2001-01-16 | 2002-07-18 | Univ Ramot | Hybrid peptides for treatment of bacteremia and septicemia |
| BR0314227A (pt) | 2002-09-11 | 2005-10-25 | Fresenius Kabi De Gmbh | Derivados de amido de hidroxialquila |
| US7919118B2 (en) | 2003-05-12 | 2011-04-05 | Affymax, Inc. | Spacer moiety for poly (ethylene glycol) modified peptide based compounds |
| ATE428727T1 (de) | 2003-05-12 | 2009-05-15 | Affymax Inc | Neue, an den erythropoietinrezeptor bindende peptide |
| CN1820024B (zh) | 2003-05-12 | 2011-06-22 | 阿费麦克斯公司 | 新的聚(乙二醇)修饰的化合物及其用途 |
| AU2004238868B2 (en) | 2003-05-12 | 2010-01-21 | Affymax, Inc. | Peptides that bind to the erythropoietin receptor |
| CN101528263B (zh) * | 2006-06-30 | 2013-01-23 | Sku资产管理有限公司 | 用于癌症的先天性免疫方法的缀合物 |
| EP2387421A1 (en) | 2009-01-14 | 2011-11-23 | SKU Asset Management GmbH | Compounds comprising n-formyl-methionine residues and tumor-targeting peptides |
| WO2012040513A1 (en) * | 2010-09-22 | 2012-03-29 | The Board Of Regents Of The University Of Texas System | Compositions and methods for the delivery of beta lapachone |
| US20130078646A1 (en) * | 2011-09-26 | 2013-03-28 | Nour Heart, Inc. | Antibodies, compositions, and assays for detection of cardiac disease |
| GB201609083D0 (en) * | 2016-05-24 | 2016-07-06 | Syntab Therapeutics Gmbh | Synthetic compound |
| US20240285787A1 (en) * | 2021-06-11 | 2024-08-29 | Eli Lilly And Company | Peptides comprising n-formyl-halogenated methionine residues and engineered antibody-peptide conjugates thereof |
-
2016
- 2016-05-24 GB GBGB1609083.9A patent/GB201609083D0/en not_active Ceased
-
2017
- 2017-05-24 EP EP17728085.6A patent/EP3464334A1/en active Pending
- 2017-05-24 JP JP2019514855A patent/JP7449091B2/ja active Active
- 2017-05-24 WO PCT/EP2017/062576 patent/WO2017202933A1/en not_active Ceased
- 2017-05-24 CN CN201780042728.2A patent/CN109641943A/zh active Pending
- 2017-05-24 US US16/304,121 patent/US11318208B2/en active Active
-
2022
- 2022-03-23 US US17/702,348 patent/US20220226486A1/en not_active Abandoned
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