DK2496596T3 - THERAPEUTIC PEPTIDES - Google Patents
THERAPEUTIC PEPTIDES Download PDFInfo
- Publication number
- DK2496596T3 DK2496596T3 DK10784830.1T DK10784830T DK2496596T3 DK 2496596 T3 DK2496596 T3 DK 2496596T3 DK 10784830 T DK10784830 T DK 10784830T DK 2496596 T3 DK2496596 T3 DK 2496596T3
- Authority
- DK
- Denmark
- Prior art keywords
- peptide
- amino acid
- groups
- group
- hydrogen atoms
- Prior art date
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- 108090000765 processed proteins & peptides Proteins 0.000 title claims description 86
- 102000004196 processed proteins & peptides Human genes 0.000 title description 22
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001413 amino acids Chemical class 0.000 claims description 65
- 125000004122 cyclic group Chemical group 0.000 claims description 38
- -1 cationic amino acid Chemical class 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 150000001576 beta-amino acids Chemical class 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 208000015181 infectious disease Diseases 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 230000001461 cytolytic effect Effects 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000003862 amino acid derivatives Chemical class 0.000 claims description 11
- 239000004599 antimicrobial Substances 0.000 claims description 11
- 230000000813 microbial effect Effects 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000004475 Arginine Substances 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000004472 Lysine Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 9
- 235000001014 amino acid Nutrition 0.000 description 71
- 150000001875 compounds Chemical class 0.000 description 47
- 239000000816 peptidomimetic Chemical class 0.000 description 44
- 238000000034 method Methods 0.000 description 37
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
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- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 5
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 125000004103 aminoalkyl group Chemical group 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
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- 238000002347 injection Methods 0.000 description 4
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- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 3
- CFYIUBWVKZQDOG-UHFFFAOYSA-N 4-[[2-[[2-[[1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-4-oxobutanoic acid Chemical compound C=1C=C([N+]([O-])=O)C=CC=1NC(=O)C(NC(=O)CNC(=O)CNC(=O)CCC(=O)O)CC1=CC=CC=C1 CFYIUBWVKZQDOG-UHFFFAOYSA-N 0.000 description 3
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- ULEBESPCVWBNIF-BYPYZUCNSA-N L-arginine amide Chemical group NC(=O)[C@@H](N)CCCNC(N)=N ULEBESPCVWBNIF-BYPYZUCNSA-N 0.000 description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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Applications Claiming Priority (2)
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| TWI852183B (zh) | 2011-12-28 | 2024-08-11 | 日商中外製藥股份有限公司 | 胜肽化合物之環化方法 |
| US10815489B2 (en) | 2015-03-13 | 2020-10-27 | Chugai Seiyaku Kabushiki Kaisha | Modified aminoacyl-tRNA synthetase and use thereof |
| GB201601868D0 (en) | 2016-02-02 | 2016-03-16 | Lytix Biopharma As | Methods |
| KR20180133463A (ko) * | 2016-04-14 | 2018-12-14 | 타오 헬스 라이프 파마 가부시키가이샤 | 아밀로스페로이드(aspd) 결합 저해 펩타이드, 및 평가 및 스크리닝 방법 |
| US12391971B2 (en) | 2017-01-31 | 2025-08-19 | Chugai Seiyaku Kabushiki Kaisha | Method for synthesizing peptides in cell-free translation system |
| GB201705255D0 (en) | 2017-03-31 | 2017-05-17 | Univ I Tromsø - Norges Arktiske Univ | Bioactive cyclic compounds |
| WO2018188761A1 (en) | 2017-04-13 | 2018-10-18 | Lytix Biopharma As | Method of reducing population size of tregs and/or mdscs |
| EP3636656A4 (en) | 2017-06-09 | 2021-04-14 | Chugai Seiyaku Kabushiki Kaisha | METHOD OF SYNTHESIS OF PEPTIDE WITH N-SUBSTITUTED AMINO ACID |
| CN111479819B (zh) | 2017-12-15 | 2024-06-14 | 中外制药株式会社 | 制备肽的方法和处理碱的方法 |
| US12312297B2 (en) | 2018-11-07 | 2025-05-27 | Chugai Seiyaku Kabushiki Kaisha | O-substituted serine derivative production method |
| CN119143631A (zh) | 2018-11-30 | 2024-12-17 | 中外制药株式会社 | 用于肽化合物或酰胺化合物的脱保护方法和在固相反应中的树脂脱除方法以及用于生产肽化合物的方法 |
| KR102994657B1 (ko) | 2019-03-15 | 2026-07-22 | 추가이 세이야쿠 가부시키가이샤 | 방향족 아미노산 유도체의 제조 방법 |
| CN110294793B (zh) * | 2019-06-24 | 2023-10-27 | 合肥科生景肽生物科技有限公司 | Sumo荧光探针及其制备方法 |
| EP4043478A4 (en) | 2019-11-07 | 2024-01-03 | Chugai Seiyaku Kabushiki Kaisha | CYCLIC PEPTIDE COMPOUND HAVING KRAS INHIBITING ACTION |
| CN114790151B (zh) * | 2022-02-14 | 2023-03-31 | 湖南省湘中制药有限公司 | 一种2-氰基-2-丙戊酸甲酯的复合催化制备方法 |
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| US4342705A (en) | 1979-11-23 | 1982-08-03 | Monsanto Company | Methylene thioethers |
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| DK523288A (da) | 1987-10-06 | 1989-04-07 | Hoffmann La Roche | Aminosyrederivater |
| CA1328333C (en) | 1988-03-04 | 1994-04-05 | Quirico Branca | Amino acid derivatives |
| US5593967A (en) | 1990-08-31 | 1997-01-14 | Warner-Lambert Company | Cholecystokinin antagonists, their preparation and therapeutic use |
| CA2088195A1 (en) | 1990-08-31 | 1992-03-01 | David C. Horwell | Cholecystokinin antagonists, their preparation and therapeutic use |
| US5387671A (en) * | 1990-12-27 | 1995-02-07 | Abbott Laboratories | Hexa- and heptapeptide anaphylatoxin-receptor ligands |
| US5885782A (en) | 1994-09-13 | 1999-03-23 | Nce Pharmaceuticals, Inc. | Synthetic antibiotics |
| IL125163A0 (en) | 1996-01-02 | 1999-01-26 | Rhone Poulenc Rorer Pharma | Substituted n-[(aminoiminomethyl or aminomethyl) phenyl] propyl amides |
| US6080767A (en) | 1996-01-02 | 2000-06-27 | Aventis Pharmaceuticals Products Inc. | Substituted n-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides |
| US6323227B1 (en) | 1996-01-02 | 2001-11-27 | Aventis Pharmaceuticals Products Inc. | Substituted N-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides |
| JP3734907B2 (ja) | 1996-12-19 | 2006-01-11 | 富士写真フイルム株式会社 | 現像処理方法 |
| DE102006018080A1 (de) * | 2006-04-13 | 2007-10-18 | Aicuris Gmbh & Co. Kg | Lysobactinamide |
| EP2078529B1 (en) * | 2006-07-10 | 2014-12-10 | PBA3 Biomed GmbH | Antimicrobial peptides |
| GB0724951D0 (en) * | 2007-12-20 | 2008-01-30 | Lytix Biopharma As | Compounds |
| DE602008002706D1 (de) * | 2008-03-18 | 2010-11-04 | Univ Dresden Tech | Modulares Gerüst zur Gestaltung von spezifischen Molekülen zur Verwendung als Pepitmimetika und Hemmer für die Proteininteraktion |
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Also Published As
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| BR112012010333A2 (pt) | 2016-03-29 |
| WO2011051692A1 (en) | 2011-05-05 |
| ES2621188T3 (es) | 2017-07-03 |
| KR20120104986A (ko) | 2012-09-24 |
| KR101730680B1 (ko) | 2017-04-26 |
| RU2676713C2 (ru) | 2019-01-10 |
| CN102762586A (zh) | 2012-10-31 |
| RU2015111706A (ru) | 2015-11-10 |
| PL2496596T3 (pl) | 2017-08-31 |
| CN102762586B (zh) | 2016-10-05 |
| EP2496596A1 (en) | 2012-09-12 |
| JP2013509389A (ja) | 2013-03-14 |
| EP2496596B1 (en) | 2017-01-11 |
| NZ599791A (en) | 2014-10-31 |
| US20130035296A1 (en) | 2013-02-07 |
| RU2015111706A3 (enExample) | 2018-10-29 |
| AU2010311186B2 (en) | 2015-09-24 |
| CA2777749C (en) | 2019-08-06 |
| US8809280B2 (en) | 2014-08-19 |
| RU2012121264A (ru) | 2013-12-10 |
| AU2010311186A1 (en) | 2012-05-31 |
| GB0919194D0 (en) | 2009-12-16 |
| RU2548905C2 (ru) | 2015-04-20 |
| JP5810090B2 (ja) | 2015-11-11 |
| CA2777749A1 (en) | 2011-05-05 |
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