CA1270098A - Acyltripeptide immunostimulants - Google Patents

Acyltripeptide immunostimulants

Info

Publication number
CA1270098A
CA1270098A CA000477796A CA477796A CA1270098A CA 1270098 A CA1270098 A CA 1270098A CA 000477796 A CA000477796 A CA 000477796A CA 477796 A CA477796 A CA 477796A CA 1270098 A CA1270098 A CA 1270098A
Authority
CA
Canada
Prior art keywords
compound
solution
mmol
acid
formula
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 - Lifetime
Application number
CA000477796A
Other languages
English (en)
French (fr)
Inventor
Jeffrey L. Ives
Frank C. Sciavolino
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.)
Pfizer Ltd Great Britain
Original Assignee
Pfizer Ltd Great Britain
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 Pfizer Ltd Great Britain filed Critical Pfizer Ltd Great Britain
Application granted granted Critical
Publication of CA1270098A publication Critical patent/CA1270098A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/16—Eight-membered rings
    • C07D313/18—Eight-membered rings not condensed with other rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Communicable Diseases (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
CA000477796A 1984-03-30 1985-03-28 Acyltripeptide immunostimulants Expired - Lifetime CA1270098A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/595,169 US4565653A (en) 1984-03-30 1984-03-30 Acyltripeptide immunostimulants
US595,169 1984-03-30

Publications (1)

Publication Number Publication Date
CA1270098A true CA1270098A (en) 1990-06-05

Family

ID=24382038

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000477796A Expired - Lifetime CA1270098A (en) 1984-03-30 1985-03-28 Acyltripeptide immunostimulants

Country Status (20)

Country Link
US (1) US4565653A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP0157572A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (1) JPS60224699A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
KR (1) KR870000372B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AU (2) AU552919B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA1270098A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DD (1) DD239406A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DK (1) DK142485A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EG (1) EG17928A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ES (1) ES8605821A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FI (1) FI851271A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GR (1) GR850783B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
HU (1) HU198086B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IL (1) IL74758A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NO (1) NO851278L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NZ (1) NZ211634A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
PH (1) PH21303A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
PL (1) PL252659A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
PT (1) PT80181B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ZA (1) ZA852335B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Families Citing this family (59)

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CA1295784C (en) * 1985-11-25 1992-02-11 James Patrick Rizzi Peptide immunostimulants
JPH0718039B2 (ja) * 1986-03-26 1995-03-01 株式会社豊田自動織機製作所 粉末付加亜鉛めっき鋼板の製造方法
FI890885A7 (fi) * 1986-08-27 1989-02-24 Pfizer Menetelmä N-(S-3-alkyyliheptanoyyli)-D-gamma-glutamyyli-glysyyli-D-ala niinin valmistamiseksi ja menetelmässä käyttökelpoiset välituotteet j a niiden valmistus
WO1988001613A1 (en) * 1986-08-27 1988-03-10 Pfizer Inc. Crystalline n-(s-3-methylheptanoyl)-d-gamma-glutamyl-glycyl-d-alanine, and processes and intermediates therefor
DE3700173A1 (de) * 1987-01-05 1988-07-14 Hoechst Ag Verfahren zur herstellung von lipophilen aminosaeurederivaten sowie lipophile aminosaeurederivate
DE3820528A1 (de) * 1988-06-16 1989-12-21 Bayer Ag Mittel zur insekten- und milbenabwehr
US5185464A (en) * 1989-02-21 1993-02-09 Pfizer Inc. Crystalline N-(S-3-methylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine, and processes and intermediates therefor
US5248820A (en) * 1989-02-21 1993-09-28 Pfizer Inc. Crystalline N-(S-3-methylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine, and processes and intermediates therefor
US5245079A (en) * 1989-02-21 1993-09-14 Pfizer Inc. Processes and intermediates for N-(S-3-alkyl-heptanoyl)-D-gamma-glutamyl-glycyl-D-alanine
US5134225A (en) * 1989-02-21 1992-07-28 Pfizer Inc. Processes and intermediates for N-(S-3-alkyl-heptanoyl)-D-gamma-glutamyl-D-alanine
US5136020A (en) * 1989-02-21 1992-08-04 Pfizer Inc. Crystalline n-(s-3-methylheptanoyl)-D-gamma-glutamyl-glycyl-D-alanine, and processes and intermediates therefor
US5798387A (en) * 1992-10-15 1998-08-25 Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai Amino acid derivatives
DE69326321T2 (de) 1992-10-15 2000-01-13 Kanegafuchi Kagaku Kogyo K.K., Osaka Neues aminosäurederivat
US5545553A (en) * 1994-09-26 1996-08-13 The Rockefeller University Glycosyltransferases for biosynthesis of oligosaccharides, and genes encoding them
US7696163B2 (en) 2001-10-10 2010-04-13 Novo Nordisk A/S Erythropoietin: remodeling and glycoconjugation of erythropoietin
US7173003B2 (en) * 2001-10-10 2007-02-06 Neose Technologies, Inc. Granulocyte colony stimulating factor: remodeling and glycoconjugation of G-CSF
WO2004099231A2 (en) * 2003-04-09 2004-11-18 Neose Technologies, Inc. Glycopegylation methods and proteins/peptides produced by the methods
US7214660B2 (en) * 2001-10-10 2007-05-08 Neose Technologies, Inc. Erythropoietin: remodeling and glycoconjugation of erythropoietin
US7399613B2 (en) * 2001-10-10 2008-07-15 Neose Technologies, Inc. Sialic acid nucleotide sugars
US8008252B2 (en) * 2001-10-10 2011-08-30 Novo Nordisk A/S Factor VII: remodeling and glycoconjugation of Factor VII
US7157277B2 (en) * 2001-11-28 2007-01-02 Neose Technologies, Inc. Factor VIII remodeling and glycoconjugation of Factor VIII
US7795210B2 (en) * 2001-10-10 2010-09-14 Novo Nordisk A/S Protein remodeling methods and proteins/peptides produced by the methods
DE60336555D1 (de) * 2002-06-21 2011-05-12 Novo Nordisk Healthcare Ag Pegylierte glykoformen von faktor vii
CN102212019B (zh) * 2003-03-14 2015-05-27 蔚所番有限公司 支化水溶性聚合物及其缀合物
WO2004091499A2 (en) * 2003-04-09 2004-10-28 Neose Technologies, Inc. Intracellular formation of peptide conjugates
US8791070B2 (en) 2003-04-09 2014-07-29 Novo Nordisk A/S Glycopegylated factor IX
ES2380093T3 (es) 2003-05-09 2012-05-08 Biogenerix Ag Composiciones y métodos para la preparación de mutantes de glucosilación de la hormona del crecimiento humana
WO2005012484A2 (en) 2003-07-25 2005-02-10 Neose Technologies, Inc. Antibody-toxin conjugates
US8633157B2 (en) * 2003-11-24 2014-01-21 Novo Nordisk A/S Glycopegylated erythropoietin
US20080305992A1 (en) * 2003-11-24 2008-12-11 Neose Technologies, Inc. Glycopegylated erythropoietin
US7842661B2 (en) * 2003-11-24 2010-11-30 Novo Nordisk A/S Glycopegylated erythropoietin formulations
ES2445948T3 (es) * 2003-11-24 2014-03-06 Ratiopharm Gmbh Eritropoyetina glicopegilada
US20080318850A1 (en) * 2003-12-03 2008-12-25 Neose Technologies, Inc. Glycopegylated Factor Ix
US20060040856A1 (en) * 2003-12-03 2006-02-23 Neose Technologies, Inc. Glycopegylated factor IX
JP4657219B2 (ja) * 2003-12-03 2011-03-23 バイオジェネリックス アーゲー ＧｌｙｃｏＰＥＧ化された顆粒球コロニー刺激因子
US7956032B2 (en) * 2003-12-03 2011-06-07 Novo Nordisk A/S Glycopegylated granulocyte colony stimulating factor
JP5743368B2 (ja) * 2004-01-08 2015-07-01 ラショファーム ゲーエムベーハー ペプチドのｏ結合型グリコシル化
WO2006010143A2 (en) 2004-07-13 2006-01-26 Neose Technologies, Inc. Branched peg remodeling and glycosylation of glucagon-like peptide-1 [glp-1]
WO2006031811A2 (en) * 2004-09-10 2006-03-23 Neose Technologies, Inc. Glycopegylated interferon alpha
EP2586456B1 (en) 2004-10-29 2016-01-20 ratiopharm GmbH Remodeling and glycopegylation of fibroblast growth factor (FGF)
WO2006074279A1 (en) * 2005-01-06 2006-07-13 Neose Technologies, Inc. Glycoconjugation using saccharyl fragments
MX2007008229A (es) * 2005-01-10 2007-09-11 Neose Technologies Inc Factor estimulador de colonias de granulocitos glicopegilado.
US20060246544A1 (en) * 2005-03-30 2006-11-02 Neose Technologies,Inc. Manufacturing process for the production of peptides grown in insect cell lines
US9187546B2 (en) * 2005-04-08 2015-11-17 Novo Nordisk A/S Compositions and methods for the preparation of protease resistant human growth hormone glycosylation mutants
JP5216580B2 (ja) * 2005-05-25 2013-06-19 ノヴォ ノルディスク アー／エス グリコペグ化第ｉｘ因子
US20070105755A1 (en) 2005-10-26 2007-05-10 Neose Technologies, Inc. One pot desialylation and glycopegylation of therapeutic peptides
CA2619969A1 (en) * 2005-08-19 2007-02-22 Neose Technologies, Inc. Glycopegylated factor vii and factor viia
US20090048440A1 (en) 2005-11-03 2009-02-19 Neose Technologies, Inc. Nucleotide Sugar Purification Using Membranes
ES2516694T3 (es) * 2006-07-21 2014-10-31 Ratiopharm Gmbh Glicosilación de péptidos a través de secuencias de glicosilación con unión en O
US20100075375A1 (en) * 2006-10-03 2010-03-25 Novo Nordisk A/S Methods for the purification of polypeptide conjugates
CA2665480C (en) * 2006-10-04 2019-11-12 Shawn Defrees Glycerol linked pegylated sugars and glycopeptides
WO2008073620A2 (en) * 2006-11-02 2008-06-19 Neose Technologies, Inc. Manufacturing process for the production of polypeptides expressed in insect cell-lines
JP2010523582A (ja) * 2007-04-03 2010-07-15 バイオジェネリクス アクチェンゲゼルシャフト グリコｐｅｇ化ｇ−ｃｓｆを用いた治療方法
US20090053167A1 (en) * 2007-05-14 2009-02-26 Neose Technologies, Inc. C-, S- and N-glycosylation of peptides
CN101778937A (zh) * 2007-06-04 2010-07-14 诺和诺德公司 使用n-乙酰葡糖胺转移酶的o-联糖基化
EP2170919B8 (en) * 2007-06-12 2016-01-20 ratiopharm GmbH Improved process for the production of nucleotide sugars
US8207112B2 (en) * 2007-08-29 2012-06-26 Biogenerix Ag Liquid formulation of G-CSF conjugate
CA2711503A1 (en) * 2008-01-08 2009-07-16 Biogenerix Ag Glycoconjugation of polypeptides using oligosaccharyltransferases
EP2257311B1 (en) 2008-02-27 2014-04-16 Novo Nordisk A/S Conjugated factor viii molecules

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US4322341A (en) * 1980-05-13 1982-03-30 Fujisawa Pharmaceutical Co Peptide, process for preparation thereof and use thereof
DK156252C (da) * 1979-07-31 1989-12-18 Fujisawa Pharmaceutical Co Analogifremgangsmaade til fremstilling af di-, tri- eller tetrapeptidderivater eller salte deraf
EP0027260B1 (en) * 1979-10-11 1985-03-13 Fujisawa Pharmaceutical Co., Ltd. Peptides, processes for their preparation and pharmaceutical compositions containing them
GR81332B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * 1980-12-01 1984-12-11 Fujisawa Pharmaceutical Co
US4493794A (en) * 1980-12-31 1985-01-15 Fujisawa Pharmaceutical Co., Ltd. Peptide, process for preparation thereof and use thereof

Also Published As

Publication number Publication date
JPS60224699A (ja) 1985-11-09
EG17928A (en) 1991-08-30
AU566460B2 (en) 1987-10-22
ES541620A0 (es) 1986-04-01
IL74758A (en) 1988-06-30
DK142485D0 (da) 1985-03-29
DK142485A (da) 1985-10-01
EP0157572A2 (en) 1985-10-09
HUT37443A (en) 1985-12-28
AU552919B2 (en) 1986-06-26
FI851271A0 (fi) 1985-03-29
KR870000372B1 (ko) 1987-03-06
HU198086B (en) 1989-07-28
PT80181A (en) 1985-04-01
FI851271L (fi) 1985-10-01
US4565653A (en) 1986-01-21
EP0157572A3 (en) 1987-01-07
AU4052385A (en) 1985-10-03
PL252659A1 (en) 1985-11-19
PT80181B (en) 1987-03-20
ZA852335B (en) 1986-11-26
ES8605821A1 (es) 1986-04-01
DD239406A5 (de) 1986-09-24
NO851278L (no) 1985-10-01
AU5647686A (en) 1986-09-04
GR850783B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1985-11-25
PH21303A (en) 1987-09-28
NZ211634A (en) 1988-10-28
FI851271A7 (fi) 1985-10-01
KR850006939A (ko) 1985-10-25
IL74758A0 (en) 1985-06-30

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