CA2827694C - Cyclic tetrapeptides and therapeutic applications thereof - Google Patents

Cyclic tetrapeptides and therapeutic applications thereof Download PDF

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Publication number
CA2827694C
CA2827694C CA2827694A CA2827694A CA2827694C CA 2827694 C CA2827694 C CA 2827694C CA 2827694 A CA2827694 A CA 2827694A CA 2827694 A CA2827694 A CA 2827694A CA 2827694 C CA2827694 C CA 2827694C
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CA
Canada
Prior art keywords
formula
compound
compound according
pharmaceutical composition
amino acids
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.)
Expired - Fee Related
Application number
CA2827694A
Other languages
English (en)
French (fr)
Other versions
CA2827694A1 (en
Inventor
Michal Zimecki
Andrzej Kaszuba
Krzysztof Kaczmarek
Janusz ZABROCKI
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.)
LODZ UNIVERSITY OF TECHNOLOGY
Peptaderm Spzoo
Original Assignee
LODZ UNIVERSITY OF TECHNOLOGY
Peptaderm Spzoo
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by LODZ UNIVERSITY OF TECHNOLOGY, Peptaderm Spzoo filed Critical LODZ UNIVERSITY OF TECHNOLOGY
Publication of CA2827694A1 publication Critical patent/CA2827694A1/en
Application granted granted Critical
Publication of CA2827694C publication Critical patent/CA2827694C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • A61K38/04Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/12Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/06Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/08Antiseborrheics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0202Peptides 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/12Cyclic peptides with only normal peptide bonds in the ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/12Cyclic peptides with only normal peptide bonds in the ring
    • C07K5/126Tetrapeptides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K7/00Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/50Cyclic peptides containing at least one abnormal peptide link
    • C07K7/54Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
    • C07K7/56Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K7/00Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/64Cyclic peptides containing only normal peptide links

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Psychology (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Transplantation (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2827694A 2010-02-19 2011-02-19 Cyclic tetrapeptides and therapeutic applications thereof Expired - Fee Related CA2827694C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
PLP.390493 2010-02-19
PL390493A PL219569B1 (pl) 2010-02-19 2010-02-19 Cykliczne tetrapeptydy i ich zastosowanie
PCT/US2011/025571 WO2011103524A2 (en) 2010-02-19 2011-02-19 Cyclic tetrapeptides and therapeutic applications thereof

Publications (2)

Publication Number Publication Date
CA2827694A1 CA2827694A1 (en) 2011-08-25
CA2827694C true CA2827694C (en) 2018-09-18

Family

ID=44483608

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2827694A Expired - Fee Related CA2827694C (en) 2010-02-19 2011-02-19 Cyclic tetrapeptides and therapeutic applications thereof

Country Status (13)

Country Link
US (3) US20130224232A1 (cg-RX-API-DMAC7.html)
EP (1) EP2536732B1 (cg-RX-API-DMAC7.html)
JP (1) JP5901543B2 (cg-RX-API-DMAC7.html)
KR (1) KR101704665B1 (cg-RX-API-DMAC7.html)
CN (1) CN102858779B (cg-RX-API-DMAC7.html)
AU (1) AU2011217882B2 (cg-RX-API-DMAC7.html)
BR (1) BR112012020833A2 (cg-RX-API-DMAC7.html)
CA (1) CA2827694C (cg-RX-API-DMAC7.html)
ES (1) ES2611663T3 (cg-RX-API-DMAC7.html)
IL (2) IL221535A (cg-RX-API-DMAC7.html)
PL (1) PL219569B1 (cg-RX-API-DMAC7.html)
RU (1) RU2568436C2 (cg-RX-API-DMAC7.html)
WO (1) WO2011103524A2 (cg-RX-API-DMAC7.html)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL219569B1 (pl) 2010-02-19 2015-05-29 Peptaderm Spółka Z Ograniczoną Odpowiedzialnością Cykliczne tetrapeptydy i ich zastosowanie
WO2016179398A1 (en) 2015-05-05 2016-11-10 Washington University Isoform-selective lysine deacetylase inhibitors
US10154997B2 (en) 2015-08-04 2018-12-18 Washington University Treatment of parasitic diseases using KDAC inhibitor compounds
US11325944B2 (en) 2017-06-16 2022-05-10 University Of Florida Research Foundation, Incorporated Macrocyclic peptides and derivatives thereof with opioid activity

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3862925A (en) * 1973-07-05 1975-01-28 American Home Prod Preparation of somatotropin release inhibiting factor and intermediates therefor
US3842067A (en) 1973-07-27 1974-10-15 American Home Prod Synthesis of(des-asn5)-srif and intermediates
JPS5726506B2 (cg-RX-API-DMAC7.html) * 1974-03-08 1982-06-04
IT1077010B (it) * 1976-09-01 1985-04-27 Snam Progetti Processo per la preparazione di copolimeri dell isobutilene contenenti insaturazioni ed atomi di alogeno reattivi
US4105603A (en) 1977-03-28 1978-08-08 The Salk Institute For Biological Studies Peptides which effect release of hormones
JPH0334991A (ja) * 1989-06-30 1991-02-14 Shionogi & Co Ltd 環状テトラペプチドおよびその製造法
US5216124A (en) 1989-12-15 1993-06-01 G. D. Searle & Co. Substituted cyclic tetrapeptides
US5541287A (en) 1992-06-09 1996-07-30 Neorx Corporation Pretargeting methods and compounds
US6777217B1 (en) * 1996-03-26 2004-08-17 President And Fellows Of Harvard College Histone deacetylases, and uses related thereto
US6013763A (en) * 1996-06-04 2000-01-11 Genentech, Inc. Peptide variants of protein A
US6281331B1 (en) 1998-03-23 2001-08-28 Trimeris, Inc. Methods and compositions for peptide synthesis
EP1071442B9 (en) * 1998-03-23 2006-01-18 Trimeris Inc. Methods and compositions for peptide synthesis (t-20)
DE19816922A1 (de) 1998-04-16 1999-10-21 Wolfgang Beck Einfache Synthese von cyclischen Tetrapeptiden aus nichtaktivierten Peptidestern an Metallzentren
AUPP505798A0 (en) * 1998-08-04 1998-08-27 Fujisawa Pharmaceutical Co., Ltd. Novel compound fr225497 substance
CZ20011342A3 (cs) 1998-10-13 2001-09-12 Fujisawa Pharmaceutical Co., Ltd. Cyklické tetrapeptidy
GB9903087D0 (en) * 1999-02-12 1999-03-31 Glaxo Group Ltd Process
DE602004009710T2 (de) * 2003-12-31 2008-08-07 F. Hoffmann-La Roche Ag Verfahren zur peptidsynthese unter verwendung einer reduzierten menge an entschützungsmittel
WO2006049597A1 (en) 2004-10-27 2006-05-11 Avanir Pharmaceuticals Amino acid-derived compounds as modulators of the reverse cholesterol transport
CN101115495B (zh) * 2004-12-14 2011-06-22 生物如恩克斯株式会社 通过runx2乙酰化作用增强bmp的骨形成活性的方法
EP2061512B1 (en) 2006-08-23 2019-10-02 Yeda Research And Development Co. Ltd. Conjugates of rgd peptides and (bacterio)chlorophyll photosensitizers and their uses
CN102036684B (zh) 2008-02-27 2017-06-09 耶达研究及发展有限公司 用于光动力疗法和坏死肿瘤成像的rgd‑(细菌)叶绿素缀合物
WO2010006267A2 (en) * 2008-07-11 2010-01-14 University Of Kansas Cyclic tetrapeptides
GB0918579D0 (en) 2009-10-22 2009-12-09 Imp Innovations Ltd Gadd45beta targeting agents
PL219569B1 (pl) 2010-02-19 2015-05-29 Peptaderm Spółka Z Ograniczoną Odpowiedzialnością Cykliczne tetrapeptydy i ich zastosowanie

Also Published As

Publication number Publication date
IL224410A (en) 2017-07-31
KR20130088004A (ko) 2013-08-07
EP2536732B1 (en) 2016-10-19
CA2827694A1 (en) 2011-08-25
WO2011103524A2 (en) 2011-08-25
AU2011217882A1 (en) 2012-10-11
JP5901543B2 (ja) 2016-04-13
US20130108655A1 (en) 2013-05-02
BR112012020833A2 (pt) 2017-12-19
IL221535A (en) 2016-08-31
US20170157204A1 (en) 2017-06-08
US20130224232A1 (en) 2013-08-29
JP2013520440A (ja) 2013-06-06
RU2568436C2 (ru) 2015-11-20
PL390493A1 (pl) 2011-08-29
AU2011217882B2 (en) 2015-02-05
US9382292B2 (en) 2016-07-05
US10238713B2 (en) 2019-03-26
WO2011103524A3 (en) 2011-12-29
PL219569B1 (pl) 2015-05-29
KR101704665B1 (ko) 2017-02-08
EP2536732A4 (en) 2014-04-30
ES2611663T3 (es) 2017-05-09
RU2012139668A (ru) 2014-03-27
CN102858779B (zh) 2016-08-03
WO2011103524A8 (en) 2012-09-13
EP2536732A2 (en) 2012-12-26
CN102858779A (zh) 2013-01-02

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