FI113943B - Förfarande för pegylation av polypeptider - Google Patents

Förfarande för pegylation av polypeptider Download PDF

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Publication number
FI113943B
FI113943B FI934015A FI934015A FI113943B FI 113943 B FI113943 B FI 113943B FI 934015 A FI934015 A FI 934015A FI 934015 A FI934015 A FI 934015A FI 113943 B FI113943 B FI 113943B
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Finland
Prior art keywords
protein
inhibitor
mutant
tnf
tnf inhibitor
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FI934015A
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English (en)
Finnish (fi)
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FI934015A0 (fi
FI934015A (fi
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Robert C Thompson
Michael T Brewer
Tadahiko Kohno
Lyman G Armes
Ronald J Evans
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Amgen Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • C07K14/47—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
    • 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
    • A61K47/56—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 macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/59—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 macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
    • A61K47/60—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 macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/52—Cytokines; Lymphokines; Interferons
    • C07K14/54—Interleukins [IL]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/705—Receptors; Cell surface antigens; Cell surface determinants
    • C07K14/715—Receptors; Cell surface antigens; Cell surface determinants for cytokines; for lymphokines; for interferons
    • 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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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Molecular Biology (AREA)
  • Zoology (AREA)
  • Toxicology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cell Biology (AREA)
  • Immunology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (17)

1. Förfarande för framställning av en förening med formeln Rx-X-R2, där 5 endera av Ri och R2 eller bäda väljs ur gruppen som bestär av en tumörnekrosfaktor (TNF) -inhibitor, en inter-leukin-1 (IL-1) -inhibitor, interleukin-2 (IL-2) -reseptor och en komplementreseptor 1 (CR1); och X är en icke-peptidisk polymerdistansgrupp, och 10 Rx och R2 är kovalent bundna till X, k ä n n e - tecknat av att man bringar Rx och R2 att reagera med X för att bilda föreningen Ri-X-R2; eller bringar Ri att reagera med X för att bilda ett 15 komplex Ri~X; bringar komplexet Ri-X att reagera med R2 för att bilda föreningen Ri-X-R2; och eventuellt isolerar föreningen Ri-X-R2.
2. Förfarande enligt patentkrav 1, kanne-tecknat av att endera av Rx och R2 eller bäda väljs 20 bland följande: en IL-l-inhibitor vald ur gruppen som bestär av : en IL-l-respetorantagonist (IL-lra) och en stympad form och >j mutant därav; eller en TNF-inhibitor vald ur gruppen bestäende av en 25 30 kD TNF-inhibitor och en stympad form och mutant därav, ^ Δ51 TNF-inhibitor och en mutant därav, och Δ53 TNF- ! inhibitor och en mutant därav.
3. Förfarande enligt patentkrav 2, k ä n n e -tecknat av att endera av Rx och R2 eller bäda av na- : 30 turen innehäller en eller modifieras för att innehälla ät- minstone en icke-naturlig cysteingrupp.
4. Förfarande enligt patentkrav 3, k ä n n e - ·. tecknat av att endera av Rx och R2 eller bäda väljs '·’ bland » · 113943 en IL-l-reseptorantagonist, där nämnda icke-naturliga cysteingrupp finns i aminosyragruppläget 0, 6, 8, 9, 84 eller 141; eller en 30 kD TNF-inhibitor eller en stympad form där-5 av, där nämnda icke-nativa cysteingrupp finns i aminosyragruppläget 1, 14, 105, 111 eller 161.
5. Förfarande enligt patentkrav 1, 2, 3 eller 4, kännetecknat av att Ri och R2 är likadana.
6. Förfarande enligt nägot av patentkraven 1, 2, 10 3, 4 eller 5, kännetecknat av att X är -Υχ- (Z)n~Y2~ där Υχ och Y2 är enheter för aktiverande grupper och (Z)n är en polymerisk basgrupp, varvid (Z)n väljs ur gruppen som bestär av polyetylenglykol, polypropylengly-kol, polyoxietylerad glyserol, dextran, kolonsyror, poly-15 β-aminosyror och kolhydratpolymerer.
7. Förfarande enligt nägot av patentkraven 1, 2, 3, 4 5 eller 6, kännetecknat av att Ri och R2 vardera kovalent binds till X med en tioeterbindning.
8. Förfarande enligt patentkrav 7, k ä n n e -20 tecknat av att Ri och R2 vardera binds till X via en naturlig eller icke-naturlig cysteingrupp.
: 9. Förfarande enligt patentkrav 8, k ä n n e - j t e c k n a t av att IL-l-inhibitorn är IL-lra, som innehäller en 25 icke-naturlig cysteingrupp i aminosyragruppläget 0, 6, 8, 9, 84 eller 141; och ! TNF-inhibitorn är en 30 kD tumörnekrosfaktorinhi- bitor eller en stympad form därav, som innehäller en icke-naturlig cysteingrupp i aminosyragruppläget 1, 14, 105, 30 111 eller 161.
'...· 10. Förfarande enligt nägot av patentkraven 1, 2, 3, 4, 5, 6, 7, 8 eller 9, kännetecknat av att .*·*. Ri och R2 är en 30 kD tumörnekrosfaktorinhibitor • eller en stympad form därav, varvid TNF-inhibitorn före- ’·* ' 35 trädesvis har icke-naturligt cystein i aminosyragruppläget ·**· 105; och 113943 X är -Yi-(Z)n-Y2_ där Yi och Y2 är enheter för ak-tiverande grupper och (Z)n är polyetylenglykol och Ri och R2 är vardera bundna till X med en tioeterbindning.
11. Förfarande enligt patentkrav 1, kanne-5 tecknat av att endera av Ri och R2 eller bäda väljs ur gruppen bestäende av en TNF-inhibitor och en IL-1-inhibitor, som företrädesvis av naturen innehäller eller som modifieras sä att de innehäller reaktivt cystein; och X är -Yi-(Z)n-Y2- där Yi och Y2 är enheter för 10 aktiverande grupper och (Z)n är den polymera basgruppen, varvid (Z)n väljs ur gruppen, som bestär av polyetylenglykol, polypropylenglykol, polyoxietylerad glycerol, dex-tran, kolonsyror, poly-p-aminosyror och kolhydratpolyme-rer, 15 varvid Ri och R2 binds kovalent vid den icke- peptidiska polymerdistansgruppen genom att antingen bringa Rx och R2 att reagera med X för att bilda tioeterbindningar mellan X och cysteinaminosyragrupperna för att bilda föreningen Rx-X-R2 och eventuellt isolera fö-20 reningen Ri-X-R2; eller bringa Rx att reagera med X för att bilda en tio-: eterbindning mellan X och cysteinaminosyragruppen för att · bilda ett komplex Ri~X, bringa Ri-X-komplexet att reagera med R2 för att bilda föreningen Rx-X-R2; och eventuellt 25 isolera föreningen Rx-X-R2.
^ 12. Förfarande enligt patentkrav 11, k ä n n e - i tecknat av att TNF-inhibitorn innehäller en 30 kD TNF-inhibitor eller en stympad form eller mutant därav, Δ51 TNF-inhibitor eller en mutant därav, eller Δ53 TNF- 30 inhibitor eller en mutant därav.
...· 13. Förfarande enligt patentkrav 11, k ä n n e - tecknat av att nämnda IL-l-inhibitor innehäller IL- ,··, 1-reseptorantagonist (IL-lra) eller en stympad form eller • · mutant därav. ι · i ·.· ‘35
14. Förfarande enligt patentkrav 1, k ä n n e - tecknat av att minst den ena av Rx och R2 är inter- 113943 leukin-1- (IL-1)-reseptorantagonist (IL-lra) och IL-lra och cysteingruppen 116 i IL-lra binds kovalent till den icke-peptidiska polymerdistansgruppen.
15. Förfarande enligt patentkrav 11, kanne-5 tecknat av att endera av Rx och R2 eller bäda är en mutant eller en stympad form av interleukin-1- (IL-1)-reseptorantagonist, som modifierats för att innehalla ät-minstone en icke-naturlig cysteingrupp, företrädesvis i aminosyragruppläget 0, 6, 8, 9, 84 eller 141, varvid den 10 icke-naturliga cysteingruppen i mutanten binds kovalent till -Yi-(Z)n-Y2-.
16. Förfarande enligt patentkrav 11, kanne-tecknat av att endera av Ri och R2 eller bäda är en mutant eller en stympad form av en 30 kDa tumornekrosfak- 15 tor (TNF) -inhibitor, som modifierats för att innehalla atminstone en icke-naturlig cysteingrupp, företrädesvis i aminosyragruppläget 1, 14, 105, 111 eller 161, varvid nämnda icke-naturliga cystein i mutanten är kovalent bun-den till -Yi~(Z)n-Y2-. 20
17. Förfarande enligt patentkrav 1, k ä n n e - tecknat av att man framställer antingen den ena av ’ Ri och R2 eller bäda enligt följande: •j man ändrar genen som kodar för polypeptiden genom ·. lägesinriktad mutagenes för att skapa en gen som kodar för 25 en mutant av nämnda polypeptid, som innehäller ätminstone ! en icke-naturlig cysteingrupp; I uttrycker den ändrande genen i ett bakteriellt expressionssystem; renar den uttryckta mutanten; 30 äterveckar mutanten i närvaro av en förening som innehäller sulfhydryl; och .:. reducerar den äterveckade mutanten med ett milt reduktionsmedel för att frigöra det icke-naturliga * * cysteinet. • »
FI934015A 1991-03-15 1993-09-14 Förfarande för pegylation av polypeptider FI113943B (sv)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US66986291A 1991-03-15 1991-03-15
US66986291 1991-03-15
US82229692A 1992-01-17 1992-01-17
US82229692 1992-01-17
US9202122 1992-03-13
PCT/US1992/002122 WO1992016221A1 (en) 1991-03-15 1992-03-13 Pegylation of polypeptides

Publications (3)

Publication Number Publication Date
FI934015A0 FI934015A0 (fi) 1993-09-14
FI934015A FI934015A (fi) 1993-09-14
FI113943B true FI113943B (sv) 2004-07-15

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EP (1) EP0575545B1 (sv)
JP (1) JP3693671B2 (sv)
AT (1) ATE240740T1 (sv)
AU (2) AU1674292A (sv)
CA (2) CA2288429C (sv)
DE (1) DE69233069T2 (sv)
DK (1) DK0575545T3 (sv)
ES (1) ES2199935T3 (sv)
FI (1) FI113943B (sv)
GE (1) GEP20033082B (sv)
NO (1) NO933270L (sv)
SG (2) SG47099A1 (sv)
WO (1) WO1992016221A1 (sv)

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