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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| TWI579296B (zh) | 2011-12-28 | 2017-04-21 | Chugai Pharmaceutical Co Ltd | Cyclization of Peptide Compounds |
| HUE059925T2 (hu) | 2015-03-13 | 2023-01-28 | Chugai Pharmaceutical Co Ltd | Módosított aminoacil-tRNS-szintetáz és alkalmazása |
| GB201601868D0 (en) | 2016-02-02 | 2016-03-16 | Lytix Biopharma As | Methods |
| US20190145962A1 (en) * | 2016-04-14 | 2019-05-16 | Tao Health Life Pharma Co., Ltd. | Peptide for inhibiting binding of amylospheroids (aspd), and evaluation and screening method |
| JP7187323B2 (ja) | 2017-01-31 | 2022-12-12 | 中外製薬株式会社 | 無細胞翻訳系におけるペプチドの合成方法 |
| 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 |
| JP7229158B2 (ja) | 2017-06-09 | 2023-02-27 | 中外製薬株式会社 | Ｎ－置換アミノ酸を含むペプチドの合成方法 |
| US11492369B2 (en) | 2017-12-15 | 2022-11-08 | Chugai Seiyaku Kabushiki Kaisha | Method for producing peptide, and method for processing bases |
| JP7279073B2 (ja) | 2018-11-07 | 2023-05-22 | 中外製薬株式会社 | Ｏ－置換セリン誘導体の製造方法 |
| KR20210098476A (ko) | 2018-11-30 | 2021-08-10 | 추가이 세이야쿠 가부시키가이샤 | 펩티드 화합물 또는 아마이드 화합물의 탈보호법 및 고상 반응에 있어서의 탈수지 방법, 및 펩티드 화합물의 제조 방법 |
| CN120518504A (zh) | 2019-03-15 | 2025-08-22 | 中外制药株式会社 | 芳香族氨基酸衍生物的制备方法 |
| 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 |
| IL292140B1 (en) | 2019-11-07 | 2025-10-01 | Chugai Pharmaceutical Co Ltd | A cyclic peptide compound with KRAS inhibitory activity |
| 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 |
| EP4637800A1 (en) | 2022-12-20 | 2025-10-29 | Lytix Biopharma AS | Compositions comprising an oncolytic peptide and chitosan |
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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 |
| WO1992004045A1 (en) | 1990-08-31 | 1992-03-19 | Warner-Lambert Company | Novel 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 |
| US6323227B1 (en) | 1996-01-02 | 2001-11-27 | Aventis Pharmaceuticals Products Inc. | 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 |
| CZ297544B6 (cs) | 1996-01-02 | 2007-02-07 | Aventis Pharmaceuticals Inc. | Substituované N-[(aminoiminomethyl)-fenyl]propylamidy nebo N-[(aminomethyl)fenyl]propylamidy |
| 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 |
| CN101528248B (zh) * | 2006-07-10 | 2015-11-25 | Pba3生物医学有限责任公司 | 抗微生物肽 |
| GB0724951D0 (en) * | 2007-12-20 | 2008-01-30 | Lytix Biopharma As | Compounds |
| ATE482186T1 (de) * | 2008-03-18 | 2010-10-15 | 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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| RU2015111706A (ru) | 2015-11-10 |
| KR20120104986A (ko) | 2012-09-24 |
| PL2496596T3 (pl) | 2017-08-31 |
| AU2010311186A1 (en) | 2012-05-31 |
| US8809280B2 (en) | 2014-08-19 |
| NZ599791A (en) | 2014-10-31 |
| JP5810090B2 (ja) | 2015-11-11 |
| EP2496596B1 (en) | 2017-01-11 |
| JP2013509389A (ja) | 2013-03-14 |
| RU2012121264A (ru) | 2013-12-10 |
| CN102762586B (zh) | 2016-10-05 |
| RU2548905C2 (ru) | 2015-04-20 |
| WO2011051692A1 (en) | 2011-05-05 |
| AU2010311186B2 (en) | 2015-09-24 |
| CA2777749A1 (en) | 2011-05-05 |
| KR101730680B1 (ko) | 2017-04-26 |
| CN102762586A (zh) | 2012-10-31 |
| ES2621188T3 (es) | 2017-07-03 |
| RU2015111706A3 (enExample) | 2018-10-29 |
| US20130035296A1 (en) | 2013-02-07 |
| RU2676713C2 (ru) | 2019-01-10 |
| BR112012010333A2 (pt) | 2016-03-29 |
| CA2777749C (en) | 2019-08-06 |
| EP2496596A1 (en) | 2012-09-12 |
| GB0919194D0 (en) | 2009-12-16 |
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