FI94419B - Förfarande för framställning av ett terapeutiskt användbart membranankar-aktivämneskonjugat - Google Patents

Förfarande för framställning av ett terapeutiskt användbart membranankar-aktivämneskonjugat Download PDF

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Publication number
FI94419B
FI94419B FI862631A FI862631A FI94419B FI 94419 B FI94419 B FI 94419B FI 862631 A FI862631 A FI 862631A FI 862631 A FI862631 A FI 862631A FI 94419 B FI94419 B FI 94419B
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Prior art keywords
membrane anchor
peptide
pam3cys
active ingredient
mmol
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FI862631A
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English (en)
Finnish (fi)
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FI862631A0 (sv
FI862631A (sv
FI94419C (sv
Inventor
Guenther Jung
Karl-Heinz Wiesmueller
Joerg Metzger
Hans-Joerg Buehring
Gerhard Becker
Wolfgang Bessler
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Hoechst Ag
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Publication of FI862631A0 publication Critical patent/FI862631A0/sv
Publication of FI862631A publication Critical patent/FI862631A/sv
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Publication of FI94419B publication Critical patent/FI94419B/sv
Publication of FI94419C publication Critical patent/FI94419C/sv

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K17/00—Carrier-bound or immobilised peptides; Preparation thereof
    • C07K17/02—Peptides being immobilised on, or in, an organic carrier
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/531—Production of immunochemical test materials
    • G01N33/532—Production of labelled immunochemicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/60—Medicinal preparations containing antigens or antibodies characteristics by the carrier linked to the antigen
    • A61K2039/6018—Lipids, e.g. in lipopeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/60—Medicinal preparations containing antigens or antibodies characteristics by the carrier linked to the antigen
    • A61K2039/6031—Proteins
    • A61K2039/6068—Other bacterial proteins, e.g. OMP
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Immunology (AREA)
  • Engineering & Computer Science (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Analytical Chemistry (AREA)
  • Hematology (AREA)
  • Biomedical Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Urology & Nephrology (AREA)
  • Cell Biology (AREA)
  • Physics & Mathematics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • Dispersion Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Biotechnology (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fodder In General (AREA)
  • Investigating Or Analysing Biological Materials (AREA)

Claims (9)

1. Förfarande för framställning av ett terapeutiskt användbart membranankar-aktivämneskonjugat, vilket konju-5 gat innehäller ätminstone en membranankarförening och kt-minstone ett kovalent med membranankarföreningen eller -föreningarna bundet aktivt ämne, känneteck-n a t av att en peptid, vars de funktioner i vilka ingen reaktion fär ske är pä ett i och för sig känt sätt skydda-10 de med skyddsgrupper, syntetiseras genom ett känt kopp-lingsförfarande pk en fast eller löslig bärare, säsom en polymer (t.ex. Merrifieldharts), att den sälunda synteti-serade, med bäraren bundna peptiden binds via peptidens N-terminal eller sidofunktion kovalent tili ett membranan-15 kar-aktivämneskonjugat, vars allmänna formel är en av föl-jande: R -CO-O-CH R -0-CH- R - O-CO-CH-, l I * l 2 R'-CO-O-CH* R'-O-CH* R'- O-CO-CH* 1. i (CH,) (CH-) (CH,) n I ^ n , 2 n , 2 n A A A 20 (CH-) (CH,) l 2 m i 2 m l 2 m R M-C0-NH-CH*-C0-X R"-C0-NH-CH*-C0-X R"-C0-NH-CH*-C0-X I. II. III. r -nh-co-<j:h2 r- co-nh-ch2 R'-NH-CO-CH* R'-CO-NH-CH* • OR 1 1 (CH,)„ (CH,) B I 2 n | 2 n i A AS I I 1 (CH,) (CH,) (CH,) ( - 2 tn 2 m | 2 tn R''-CO-NH-CH*-CO-X R* '-CO-NH-CH--CO-X R-NH-C0-CH*-CC-X IV. V. VI. 30 R.—CH , • 1 I 2 R,-CH* * I (CH > I 2 n A (CH,) I 2 tn __ R-C0-N'H-CH*-C0-X
2. Förfarande enligt patentkrav 1, k ä n n e -35 tecknat av att membranankarföreningen är Pam3Cys 37 94419 eller Pam3Cys-Ser eller en Pam3Cys-peptid med 1-10 kol-atomer.
3. Förfarande enligt patentkrav 1, k ä n n e -tecknat av att membranankarföreningen är
3 D : vh. 36 . 94419 där A är svavel, syre, disulfid (-S-S-), metylen (-CH2-) eller -NH-; B är en grupp -S(CH2)n-(substituerad alkyl), där den substituerade alkylen är vilken som heist av de i formlerna I - V visade tili gruppen -(CH2)n- anslutande 5 substituerade alkylerna; n = 0 - 5; m är 1 eller 2; C* är en asymmetrisk kolatom, vars konfiguration är R eller S; R, R', R" är lika eller o lika och betecknar en väteatom eller en alkyl-, alkenyl- eller alkynylgrupp med 7-25 kolatoroer, vilken grupp som substituenter kan ha hydroxi-, 10 amino-, oxo-, acyl-, alkyl- eller cykloalkylgrupper, och R, och R2 är lika eller olika och kan beteckna samma som R, R' eller Rw eller grupper -OR, -OCOR, -COOR, -NHCOR, -CONHR, och X är ett aktivt ämne eller en spacer-aktivämnesgrupp, med undantag av föreningar, där X är en aminosyrasekvens 15 med 2-10 naturliga aminosyror, att det sälunda fram-ställda peptidkonjugatet isoleras genom att skyddsgrupper-na och peptid/bärarbindningen avlägsnas pä ett i och för sig känt sätt, varvid en membranankarpeptid eller ett mem-branankar-aktivämneskonjugat erheille, varvid det aktiva 20 ämnet är en antigen, säsom t.ex. en lägmolekular delsek-vens av glykoprotein, virushöljeprotein, bakteriecell-väggsprotein eller protozoaprotein (antigendeterminant, epitop), en bakteriemembranbeständsdel, säsom muramyldi-. peptid, lipopolysackarid, en naturlig eller syntetisk hap- • 25 ten, ett antibiotikum, en hormon, nukleocid, nukleotid, nukleinsyra, ett enzym, ett enzymsubstrat, en enzyminhibi-tor, biotin, avidin, polyetylenglykol, ett peptidaktivämne med peptid, säsom tuftsin, polylysin, en fluorescensmar-kör, FITC, RITC, dansyl, luminol eller kumarin, en biolu-30 minescensmarkör, spinmarkör, alkaloid, steroid, biogen amin, vitamin, en toxin, säsom t.ex. digoxin, falloidin, amanitin, tetrodoxin eller dyl., en komplexbildare eller ett läkemedel.
4. Förfarande enligt patentkrav 1, kanne-tecknat av att membranankarföreningen är α-alkyl-/3-hydroxylpeptid (mykolylpeptid) , vars peptidkedja har 1 -10 aminosyror. 10 5. Förfarande enligt patentkrav 1, kanne- tecknat av att membranankarföreningen är S-(1,2-dioktadekyloxikarbonyletyl)-cystein eller en homolog av denna förening.
5 PaxnCys (Pam)-OH eller Pam(a-Pam)-Cys[Pam(a-Pam) ]-OH.
6. Förfarande enligt nägot av de föregäende patent- 15 kraven, kännetecknat av att det aktiva ämnet är kovalent bundet med tvä, eventuellt olika membranankar-föreningar.
7. Förfarande enligt nägot av de föregäende patent-kraven, kännetecknat av att det aktiva ämnet 20 dessutom är kovalent bundet med en i och för sig känd adjuvant för immuniseringssyften, t.ex. muramyldipeptid och/ eller lipopolysackarid.
8. Förfarande enligt nägot av de föregäende patent-kraven, kännetecknat av att flera membranan- • 25 kar-aktivämneskonjugatföreningar är tvärbundna med varand-ra i lipid- och/eller aktivämnesdelen.
9. Förfarande enligt nägot av de föregäende patent-kraven, kännetecknat av att membranankarföreningen och det aktiva ämnet sammanbinds kovalent via ett 30 tvärbindningsmedel, t.ex. ett dikarboxylsyraderivat, en diol, diamin, polyetylenglykol, epoxid, ett maleinsyrade-rivat el. dyl.
FI862631A 1985-06-24 1986-06-19 Förfarande för framställning av ett terapeutiskt användbart membranankar-aktivämneskonjugat FI94419C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE3522512 1985-06-24
DE3522512 1985-06-24
DE3546150 1985-12-27
DE19853546150 DE3546150A1 (de) 1985-06-24 1985-12-27 Membrananker-wirkstoffkonjugat, seine herstellung sowie seine verwendung

Publications (4)

Publication Number Publication Date
FI862631A0 FI862631A0 (sv) 1986-06-19
FI862631A FI862631A (sv) 1986-12-25
FI94419B true FI94419B (sv) 1995-05-31
FI94419C FI94419C (sv) 1995-09-11

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FI862631A FI94419C (sv) 1985-06-24 1986-06-19 Förfarande för framställning av ett terapeutiskt användbart membranankar-aktivämneskonjugat

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EP (1) EP0210412B1 (sv)
JP (1) JP2594259B2 (sv)
KR (1) KR930008091B1 (sv)
AT (1) ATE131491T1 (sv)
AU (1) AU611385B2 (sv)
CA (1) CA1340656C (sv)
DE (2) DE3546150A1 (sv)
DK (1) DK172399B1 (sv)
ES (1) ES8801677A1 (sv)
FI (1) FI94419C (sv)
NO (1) NO174207C (sv)
PT (1) PT82826B (sv)

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DE4329309A1 (de) * 1993-08-31 1995-03-09 Rapp Polymere Gmbh Lipopeptid-Verbindungen
EP0641776A3 (en) * 1993-09-08 1997-05-02 Takeda Chemical Industries Ltd Thioglycerol derivatives.
FR2727117A1 (fr) * 1994-11-18 1996-05-24 Geffard Michel Utilisation de conjugues de la polylysine pour la preparation de medicaments utiles dans le traitement des maladies neurodegeneratives et des affections degeneratives a caractere autoimmun
US6117940A (en) * 1997-10-17 2000-09-12 Mjalli; Adnan M. M. Amino-ketone solid support templates
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DE102009034779A1 (de) 2009-07-25 2011-02-03 Emc Microcollections Gmbh Synthetische Analoga bakterieller Lipopeptide und ihre Anwendung zur Therapie und Prophylaxe allergischer Erkrankungen
EA031379B1 (ru) * 2010-03-23 2018-12-28 Новартис Аг Соединения (липопептиды на основе цистеина) и композиции в качестве агонистов tlr2, применяемые для лечения инфекционных, воспалительных, респираторных и других заболеваний
DE102011018499A1 (de) 2011-04-23 2012-10-25 Emc Microcollections Gmbh Topische Nanopartikel-Vakzine zur Immunstimulation der dendritischen Zellen in der Haut
WO2014055754A1 (en) * 2012-10-05 2014-04-10 The University Of Kansas Conformationally-constrained kinked endosomal-disrupting peptides
US10766928B2 (en) 2012-10-05 2020-09-08 The University Of Kansas Targeted conformationally-constrained kinked endosomal disrupting peptides
WO2015163488A1 (en) * 2014-04-25 2015-10-29 Ajinomoto Co., Inc. Immunostimulating agent
DE102016005550B4 (de) 2016-05-09 2024-09-26 Hans-Georg Rammensee Adjuvans zur lnduzierung einer zellulären lmmunantwort
KR102665710B1 (ko) 2017-08-24 2024-05-14 노보 노르디스크 에이/에스 Glp-1 조성물 및 그 용도
IL294521A (en) 2020-02-18 2022-09-01 Novo Nordisk As glp-1 compounds and their uses

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Publication number Publication date
DK294086A (da) 1986-12-25
FI862631A0 (sv) 1986-06-19
NO862511D0 (no) 1986-06-23
KR870000359A (ko) 1987-02-18
DE3650448D1 (de) 1996-01-25
AU611385B2 (en) 1991-06-13
NO174207C (no) 1994-03-30
EP0210412A2 (de) 1987-02-04
DK172399B1 (da) 1998-05-18
ES8801677A1 (es) 1988-02-16
KR930008091B1 (en) 1993-08-25
JP2594259B2 (ja) 1997-03-26
EP0210412A3 (en) 1990-02-07
FI862631A (sv) 1986-12-25
PT82826B (pt) 1989-01-17
JPS6263600A (ja) 1987-03-20
FI94419C (sv) 1995-09-11
ES556417A0 (es) 1988-02-16
PT82826A (de) 1986-07-01
ATE131491T1 (de) 1995-12-15
EP0210412B1 (de) 1995-12-13
NO174207B (no) 1993-12-20
CA1340656C (en) 1999-07-20
DE3546150A1 (de) 1987-01-22
DK294086D0 (da) 1986-06-23
NO862511L (no) 1986-12-29
AU5894386A (en) 1987-01-08

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