CA2777749C - Therapeutic peptides comprising a disubstituted beta-amino acid for treating microbial infections or tumours - Google Patents

Therapeutic peptides comprising a disubstituted beta-amino acid for treating microbial infections or tumours Download PDF

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Publication number
CA2777749C
CA2777749C CA2777749A CA2777749A CA2777749C CA 2777749 C CA2777749 C CA 2777749C CA 2777749 A CA2777749 A CA 2777749A CA 2777749 A CA2777749 A CA 2777749A CA 2777749 C CA2777749 C CA 2777749C
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CA
Canada
Prior art keywords
amino acid
peptide
peptidomimetic
group
acid derivative
Prior art date
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Application number
CA2777749A
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English (en)
French (fr)
Other versions
CA2777749A1 (en
Inventor
Morten Strom
Terkel Hansen
Martina Havelkova
Veronika Torfoss
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lytix Biopharma AS
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Lytix Biopharma AS
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Publication of CA2777749A1 publication Critical patent/CA2777749A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/07—Tetrapeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/08—Peptides having 5 to 11 amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/02—Linear peptides containing at least one abnormal peptide link
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Oncology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2777749A 2009-11-02 2010-11-02 Therapeutic peptides comprising a disubstituted beta-amino acid for treating microbial infections or tumours Active CA2777749C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB0919194.1A GB0919194D0 (en) 2009-11-02 2009-11-02 Compounds
GB0919194.1 2009-11-02
PCT/GB2010/002024 WO2011051692A1 (en) 2009-11-02 2010-11-02 Therapeutic peptides

Publications (2)

Publication Number Publication Date
CA2777749A1 CA2777749A1 (en) 2011-05-05
CA2777749C true CA2777749C (en) 2019-08-06

Family

ID=41435032

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2777749A Active CA2777749C (en) 2009-11-02 2010-11-02 Therapeutic peptides comprising a disubstituted beta-amino acid for treating microbial infections or tumours

Country Status (14)

Country Link
US (1) US8809280B2 (enExample)
EP (1) EP2496596B1 (enExample)
JP (1) JP5810090B2 (enExample)
KR (1) KR101730680B1 (enExample)
CN (1) CN102762586B (enExample)
AU (1) AU2010311186B2 (enExample)
CA (1) CA2777749C (enExample)
DK (1) DK2496596T3 (enExample)
ES (1) ES2621188T3 (enExample)
GB (1) GB0919194D0 (enExample)
NZ (1) NZ599791A (enExample)
PL (1) PL2496596T3 (enExample)
RU (2) RU2548905C2 (enExample)
WO (1) WO2011051692A1 (enExample)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
AU2023413685A1 (en) 2022-12-20 2025-06-19 Lytix Biopharma As Compositions comprising an oncolytic peptide and chitosan

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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
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IL125163A0 (en) 1996-01-02 1999-01-26 Rhone Poulenc Rorer Pharma Substituted n-[(aminoiminomethyl or aminomethyl) phenyl] propyl amides
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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
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Also Published As

Publication number Publication date
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
DK2496596T3 (en) 2017-04-03
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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