CA1270098A - Acyltripeptide immunostimulants - Google Patents
Acyltripeptide immunostimulantsInfo
- 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
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)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (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)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US595,169 | 1984-03-30 | ||
US06/595,169 US4565653A (en) | 1984-03-30 | 1984-03-30 | Acyltripeptide immunostimulants |
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 (instruction) |
EP (1) | EP0157572A3 (instruction) |
JP (1) | JPS60224699A (instruction) |
KR (1) | KR870000372B1 (instruction) |
AU (2) | AU552919B2 (instruction) |
CA (1) | CA1270098A (instruction) |
DD (1) | DD239406A5 (instruction) |
DK (1) | DK142485A (instruction) |
EG (1) | EG17928A (instruction) |
ES (1) | ES8605821A1 (instruction) |
FI (1) | FI851271A7 (instruction) |
GR (1) | GR850783B (instruction) |
HU (1) | HU198086B (instruction) |
IL (1) | IL74758A (instruction) |
NO (1) | NO851278L (instruction) |
NZ (1) | NZ211634A (instruction) |
PH (1) | PH21303A (instruction) |
PL (1) | PL252659A1 (instruction) |
PT (1) | PT80181B (instruction) |
ZA (1) | ZA852335B (instruction) |
Families Citing this family (59)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
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 |
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 |
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 |
US5134225A (en) * | 1989-02-21 | 1992-07-28 | Pfizer Inc. | Processes and intermediates for N-(S-3-alkyl-heptanoyl)-D-gamma-glutamyl-D-alanine |
CA2125679C (en) | 1992-10-15 | 2005-06-28 | Ishizuka Masaaki | Novel amino acid derivatives |
US5798387A (en) * | 1992-10-15 | 1998-08-25 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Amino acid derivatives |
US5545553A (en) * | 1994-09-26 | 1996-08-13 | The Rockefeller University | Glycosyltransferases for biosynthesis of oligosaccharides, and genes encoding them |
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 |
US7795210B2 (en) * | 2001-10-10 | 2010-09-14 | Novo Nordisk A/S | Protein remodeling methods and proteins/peptides produced by the methods |
US7157277B2 (en) * | 2001-11-28 | 2007-01-02 | Neose Technologies, Inc. | Factor VIII remodeling and glycoconjugation of Factor VIII |
US7696163B2 (en) | 2001-10-10 | 2010-04-13 | Novo Nordisk A/S | Erythropoietin: remodeling and glycoconjugation of erythropoietin |
US8008252B2 (en) * | 2001-10-10 | 2011-08-30 | Novo Nordisk A/S | Factor VII: remodeling and glycoconjugation of Factor VII |
US7173003B2 (en) * | 2001-10-10 | 2007-02-06 | Neose Technologies, Inc. | Granulocyte colony stimulating factor: remodeling and glycoconjugation of G-CSF |
DE60336555D1 (de) * | 2002-06-21 | 2011-05-12 | Novo Nordisk Healthcare Ag | Pegylierte glykoformen von faktor vii |
KR20060003862A (ko) * | 2003-03-14 | 2006-01-11 | 네오스 테크놀로지스, 인크. | 수용성분기폴리머 및 그 접합체 |
US7691603B2 (en) * | 2003-04-09 | 2010-04-06 | Novo Nordisk A/S | Intracellular formation of peptide conjugates |
NZ542586A (en) * | 2003-04-09 | 2009-11-27 | Biogenerix Ag | Method of forming a covalent conjugate between a G-CSF peptide and PEG |
US8791070B2 (en) | 2003-04-09 | 2014-07-29 | Novo Nordisk A/S | Glycopegylated factor IX |
JP2007523630A (ja) | 2003-05-09 | 2007-08-23 | ネオス テクノロジーズ インコーポレイテッド | ヒト成長ホルモングリコシル化突然変異体の組成と調合法 |
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 |
JP4719686B2 (ja) * | 2003-11-24 | 2011-07-06 | バイオジェネリックス アーゲー | GlycoPEG化エリスロポエチン |
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 |
US20060040856A1 (en) * | 2003-12-03 | 2006-02-23 | Neose Technologies, Inc. | Glycopegylated factor IX |
US20080318850A1 (en) * | 2003-12-03 | 2008-12-25 | Neose Technologies, Inc. | Glycopegylated Factor Ix |
US7956032B2 (en) * | 2003-12-03 | 2011-06-07 | Novo Nordisk A/S | Glycopegylated granulocyte colony stimulating factor |
EP1694274B1 (en) * | 2003-12-03 | 2013-04-24 | BioGeneriX AG | Glycopegylated granulocyte colony stimulating factor |
US7338933B2 (en) * | 2004-01-08 | 2008-03-04 | Neose Technologies, Inc. | O-linked glycosylation of peptides |
EP1771066A2 (en) | 2004-07-13 | 2007-04-11 | 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 |
JP5948627B2 (ja) * | 2004-10-29 | 2016-07-20 | レイショファーム ゲーエムベーハー | 線維芽細胞成長因子(fgf)のリモデリングと糖質ペグ化 |
EP1838332A1 (en) * | 2005-01-06 | 2007-10-03 | Neose Technologies, Inc. | Glycoconjugation using saccharyl fragments |
ES2449195T3 (es) * | 2005-01-10 | 2014-03-18 | Ratiopharm Gmbh | Factor estimulante de colonias de granulocitos glicopegilado |
EP1866427A4 (en) * | 2005-03-30 | 2010-09-01 | Novo Nordisk As | METHOD OF MANUFACTURING PEPTIDES PRODUCED IN INSECT CELL LINES |
US20070154992A1 (en) * | 2005-04-08 | 2007-07-05 | Neose Technologies, Inc. | Compositions and methods for the preparation of protease resistant human growth hormone glycosylation mutants |
EP1891231A4 (en) * | 2005-05-25 | 2011-06-22 | Novo Nordisk As | GLYCOPEGYLATED FACTOR IX |
CN102719508A (zh) * | 2005-08-19 | 2012-10-10 | 诺和诺德公司 | 糖基聚乙二醇化的因子vii和因子viia |
US20070105755A1 (en) * | 2005-10-26 | 2007-05-10 | Neose Technologies, Inc. | One pot desialylation and glycopegylation of therapeutic peptides |
US20090048440A1 (en) * | 2005-11-03 | 2009-02-19 | Neose Technologies, Inc. | Nucleotide Sugar Purification Using Membranes |
US20080248959A1 (en) * | 2006-07-21 | 2008-10-09 | Neose Technologies, Inc. | Glycosylation of peptides via o-linked glycosylation sequences |
JP2010505874A (ja) * | 2006-10-03 | 2010-02-25 | ノヴォ ノルディスク アー/エス | ポリペプチドコンジュゲートの精製方法 |
PT2068907T (pt) * | 2006-10-04 | 2018-01-15 | Novo Nordisk As | Açúcares e glicopéptidos peguilados ligados a glicerol |
US20080207487A1 (en) * | 2006-11-02 | 2008-08-28 | Neose Technologies, Inc. | Manufacturing process for the production of polypeptides expressed in insect cell-lines |
PL2144923T3 (pl) * | 2007-04-03 | 2013-12-31 | Biogenerix Ag | Sposoby leczenia z użyciem glikopegilowanego G-CSF |
US20090053167A1 (en) * | 2007-05-14 | 2009-02-26 | Neose Technologies, Inc. | C-, S- and N-glycosylation of peptides |
WO2008151258A2 (en) * | 2007-06-04 | 2008-12-11 | Neose Technologies, Inc. | O-linked glycosylation using n-acetylglucosaminyl transferases |
CN101778859B (zh) * | 2007-06-12 | 2014-03-26 | 诺和诺德公司 | 改良的用于生产核苷酸糖的方法 |
US8207112B2 (en) * | 2007-08-29 | 2012-06-26 | Biogenerix Ag | Liquid formulation of G-CSF conjugate |
CN102037004A (zh) * | 2008-01-08 | 2011-04-27 | 生物种属学股份公司 | 使用寡糖基转移酶的多肽的糖缀合 |
CN103497246B (zh) | 2008-02-27 | 2016-08-10 | 诺沃—诺迪斯克有限公司 | 缀合的因子viii分子 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 (instruction) * | 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 |
-
1984
- 1984-03-30 US US06/595,169 patent/US4565653A/en not_active Expired - Fee Related
-
1985
- 1985-03-26 PH PH32046A patent/PH21303A/en unknown
- 1985-03-26 EP EP85302065A patent/EP0157572A3/en not_active Withdrawn
- 1985-03-27 ES ES541620A patent/ES8605821A1/es not_active Expired
- 1985-03-28 DD DD85274551A patent/DD239406A5/de not_active IP Right Cessation
- 1985-03-28 CA CA000477796A patent/CA1270098A/en not_active Expired - Lifetime
- 1985-03-28 PT PT80181A patent/PT80181B/pt not_active IP Right Cessation
- 1985-03-28 GR GR850783A patent/GR850783B/el unknown
- 1985-03-28 EG EG201/85A patent/EG17928A/xx active
- 1985-03-28 ZA ZA852335A patent/ZA852335B/xx unknown
- 1985-03-29 NO NO851278A patent/NO851278L/no unknown
- 1985-03-29 FI FI851271A patent/FI851271A7/fi not_active Application Discontinuation
- 1985-03-29 NZ NZ211634A patent/NZ211634A/xx unknown
- 1985-03-29 AU AU40523/85A patent/AU552919B2/en not_active Ceased
- 1985-03-29 HU HU851217A patent/HU198086B/hu unknown
- 1985-03-29 DK DK142485A patent/DK142485A/da not_active Application Discontinuation
- 1985-03-29 JP JP60066380A patent/JPS60224699A/ja active Pending
- 1985-03-29 PL PL25265985A patent/PL252659A1/xx unknown
- 1985-03-29 IL IL74758A patent/IL74758A/xx unknown
- 1985-03-29 KR KR1019850002106A patent/KR870000372B1/ko not_active Expired
-
1986
- 1986-04-22 AU AU56476/86A patent/AU566460B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
PH21303A (en) | 1987-09-28 |
EP0157572A3 (en) | 1987-01-07 |
AU4052385A (en) | 1985-10-03 |
US4565653A (en) | 1986-01-21 |
FI851271A0 (fi) | 1985-03-29 |
NZ211634A (en) | 1988-10-28 |
FI851271L (fi) | 1985-10-01 |
ES541620A0 (es) | 1986-04-01 |
AU5647686A (en) | 1986-09-04 |
PL252659A1 (en) | 1985-11-19 |
JPS60224699A (ja) | 1985-11-09 |
DK142485D0 (da) | 1985-03-29 |
FI851271A7 (fi) | 1985-10-01 |
IL74758A0 (en) | 1985-06-30 |
KR870000372B1 (ko) | 1987-03-06 |
AU566460B2 (en) | 1987-10-22 |
DK142485A (da) | 1985-10-01 |
HU198086B (en) | 1989-07-28 |
GR850783B (instruction) | 1985-11-25 |
EG17928A (en) | 1991-08-30 |
PT80181B (en) | 1987-03-20 |
KR850006939A (ko) | 1985-10-25 |
AU552919B2 (en) | 1986-06-26 |
HUT37443A (en) | 1985-12-28 |
PT80181A (en) | 1985-04-01 |
DD239406A5 (de) | 1986-09-24 |
IL74758A (en) | 1988-06-30 |
ES8605821A1 (es) | 1986-04-01 |
NO851278L (no) | 1985-10-01 |
ZA852335B (en) | 1986-11-26 |
EP0157572A2 (en) | 1985-10-09 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MKLA | Lapsed |