CH614718A5 - Process for the preparation of glucosamine derivatives - Google Patents
Process for the preparation of glucosamine derivativesInfo
- Publication number
- CH614718A5 CH614718A5 CH898378A CH898378A CH614718A5 CH 614718 A5 CH614718 A5 CH 614718A5 CH 898378 A CH898378 A CH 898378A CH 898378 A CH898378 A CH 898378A CH 614718 A5 CH614718 A5 CH 614718A5
- Authority
- CH
- Switzerland
- Prior art keywords
- increase
- glucosamine derivatives
- preparation
- glucosamine
- derivatives
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
-
- 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
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
- C07K9/005—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure containing within the molecule the substructure with m, n > 0 and m+n > 0, A, B, D, E being heteroatoms; X being a bond or a chain, e.g. muramylpeptides
Abstract
Glucosamine derivatives of the formula <IMAGE> (X, R, R2, R7-9 and n have the meaning stated in Claim 1) are obtained by acidic splitting up of a corresponding 5,6-O-dioxolanylglucofurano- DELTA <2>-oxazoline which contains an alkanoyl dipeptide residue in position 3. These glucosamine derivatives have the ability to increase the immunogenicity of an antigen on being mixed therewith and, on systemic administration, to increase the immunological reactivity of the treated organism. They can thus be used as adjuvants to increase the protection conferred by vaccines against bacterial, viral or parasitic pathogens.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1604275A CH613709A5 (en) | 1975-12-10 | 1975-12-10 | Process for the preparation of glucosamine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
CH614718A5 true CH614718A5 (en) | 1979-12-14 |
Family
ID=4414012
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1604275A CH613709A5 (en) | 1975-12-10 | 1975-12-10 | Process for the preparation of glucosamine derivatives |
CH898378A CH614718A5 (en) | 1975-12-10 | 1978-08-24 | Process for the preparation of glucosamine derivatives |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1604275A CH613709A5 (en) | 1975-12-10 | 1975-12-10 | Process for the preparation of glucosamine derivatives |
Country Status (30)
Country | Link |
---|---|
JP (1) | JPS5273820A (en) |
AR (2) | AR224091A1 (en) |
AT (1) | AT365607B (en) |
AU (1) | AU508764B2 (en) |
BE (1) | BE849214A (en) |
CA (1) | CA1262400A (en) |
CH (2) | CH613709A5 (en) |
CS (4) | CS205028B2 (en) |
DD (1) | DD129781A5 (en) |
DE (1) | DE2655500A1 (en) |
DK (1) | DK154654C (en) |
ES (2) | ES454118A1 (en) |
FI (1) | FI64164C (en) |
FR (1) | FR2361902A1 (en) |
GB (1) | GB1570625A (en) |
GR (1) | GR61647B (en) |
HK (1) | HK32883A (en) |
HU (1) | HU177970B (en) |
IE (1) | IE44190B1 (en) |
IL (1) | IL51076A (en) |
MY (1) | MY8400123A (en) |
NL (1) | NL7613666A (en) |
NO (1) | NO144850C (en) |
NZ (1) | NZ182837A (en) |
PL (4) | PL110794B1 (en) |
PT (1) | PT65946B (en) |
SE (1) | SE445923B (en) |
SG (1) | SG11083G (en) |
SU (3) | SU660589A3 (en) |
ZA (1) | ZA767333B (en) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4186194A (en) * | 1973-10-23 | 1980-01-29 | Agence Nationale De Valorisation De La Recherche (Anvar) | Water soluble agents effective as immunological adjuvants for stimulating, in the host the immune response to various antigens and compositions, notably vaccines containing said water soluble agents |
US4370265A (en) * | 1974-10-22 | 1983-01-25 | Agence Nationale De Valorisation | Water soluble agents effective as immunological adjuvants for stimulating in the host the immune response to various antigens and compositions, notably vaccines containing said water soluble agents |
CH636887A5 (en) * | 1976-04-26 | 1983-06-30 | Syntex Inc | Process for the preparation of novel immunological adjuvant compounds |
DE2862107D1 (en) | 1977-12-02 | 1982-11-18 | Takeda Chemical Industries Ltd | Glucosamine-peptide derivatives and their pharmaceutical compositions |
FI66878C (en) * | 1978-02-24 | 1984-12-10 | Ciba Geigy Ag | FOERFARANDE FOER FRAMSTAELLNING AV NYA ANTIGENDERIVAT |
US4397844A (en) * | 1978-02-24 | 1983-08-09 | Ciba-Geigy Corporation | Antigen derivatives and processes for their preparation |
FR2420545A1 (en) * | 1978-03-20 | 1979-10-19 | Anvar | NEW ESTERS OF N-ACETYL-MURAMYL-AMINOACYL-GLUTAMIC ACID OR SUBSTITUTION DERIVATIVES THEREOF WITH ANTI-INFECTIOUS PROPERTIES AND / OR IMMUNOLOGICAL ADJUVANTS |
FR2442241A2 (en) * | 1978-03-20 | 1980-06-20 | Anvar | NOVEL ESTER COMPOUNDS OF MURAMYL-PEPTIDE, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, IN PARTICULAR IN THE FORM OF LIPOSOMES |
FR2428050A1 (en) * | 1978-06-05 | 1980-01-04 | Anvar | OLIGOMERS OF MURAMYL-PEPTIDE COMPOUNDS AND DRUGS CONTAINING THEM |
FR2428051A1 (en) * | 1978-06-05 | 1980-01-04 | Anvar | NOVEL MURAMYL-PEPTIDE COMPOUNDS AND MEDICAMENTS CONTAINING THEM |
FR2446292A1 (en) * | 1979-01-12 | 1980-08-08 | Anvar | MURAMYL-PEPTIDES FIXED ON PEPTIDE POLYMERS AND MEDICAMENTS CONTAINING THEM |
US4256735A (en) * | 1979-01-29 | 1981-03-17 | Merck & Co., Inc. | Immunologically active dipeptidyl saccharides and methods of preparation |
FR2449697A1 (en) | 1979-02-20 | 1980-09-19 | Anvar | NOVEL MURAMYL-PEPTIDES SUBSTITUTED ON PEPTIDE NITROGEN AND MEDICAMENTS CONTAINING THEM |
JPS55111499A (en) * | 1979-02-21 | 1980-08-28 | Takeda Chem Ind Ltd | Glucosamine derivative and its preparation |
JPS5618996A (en) * | 1979-06-21 | 1981-02-23 | Dai Ichi Seiyaku Co Ltd | Muramyldipeptide derivative |
FI75578C (en) * | 1979-07-25 | 1988-07-11 | Ciba Geigy Ag | Analogous procedure for the preparation of pharmacologically acting lipophilic a phosphatidylmuramyl peptides. |
JPS5649396A (en) * | 1979-09-28 | 1981-05-02 | Dai Ichi Seiyaku Co Ltd | Novel muramyldipeptide derivative |
DE3070457D1 (en) * | 1979-10-02 | 1985-05-15 | Ciba Geigy Ag | Combinatory compositions for use in a method for enhancing the activity of antibiotics, antibiotic preparations having enhanced activity and process for their production |
FI803077A (en) * | 1979-10-12 | 1981-04-13 | Ciba Geigy Ag | FOERFARANDE FOER FRAMSTAELLNING AV MYRAMYLPEPTIDER |
US4409209A (en) * | 1979-10-12 | 1983-10-11 | Ciba-Geigy Corporation | Novel phosphorylmuramyl peptides and processes for the manufacture thereof |
US4406889A (en) * | 1980-02-15 | 1983-09-27 | Ciba-Geigy Corporation | Derivatives of aldohexoses, intermediates, processes for their manufacture, preparations containing such compounds, and their use |
US4368190A (en) * | 1980-04-17 | 1983-01-11 | Merck & Co., Inc. | Immunologically active dipeptidyl 4-O-,6-O-acyl-2-amino-2-deoxy-D-glucose derivatives and methods for their preparation |
US4310514A (en) | 1980-05-05 | 1982-01-12 | Merck & Co., Inc. | Immunologically active dipeptidyl 5-0,6-0-acyl-2-amino-2-deoxy-D-glucofuranose derivatives and methods of preparation |
EP0056560A1 (en) * | 1981-01-19 | 1982-07-28 | Ciba-Geigy Ag | Active antibiotic compositions, process for their manufacture and process for the antibiotic activity of antibiotics |
GR78246B (en) * | 1981-01-23 | 1984-09-26 | Ciba Geigy Ag | |
JPS6042398A (en) * | 1983-08-18 | 1985-03-06 | Toshiyuki Hamaoka | Muramyldipeptide active ester derivative |
EP0541486A1 (en) * | 1991-11-07 | 1993-05-12 | Ciba-Geigy Ag | Polycyclic conjugates |
JP4875612B2 (en) * | 2005-04-27 | 2012-02-15 | 真司 武岡 | Cationic amino acid type lipid |
US10610564B2 (en) | 2015-02-26 | 2020-04-07 | Stc.Unm | IRGM and precision autophagy controls for antimicrobial and inflammatory disease states and methods of detection of autophagy |
EP3387005B1 (en) * | 2015-12-10 | 2022-08-24 | Bharat Biotech International Limited | Novel muramyl peptide derivative compound, synthesis and uses thereof |
US10576147B2 (en) * | 2015-12-15 | 2020-03-03 | Bharat Biotech International Limited | Muramyl peptide derivative compound, synthesis and uses thereof |
JP7399846B2 (en) | 2017-08-21 | 2023-12-18 | セルジーン コーポレイション | Preparation process of (S)-TERT-butyl 4,5-diamino-5-oxopentanoate |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4186194A (en) * | 1973-10-23 | 1980-01-29 | Agence Nationale De Valorisation De La Recherche (Anvar) | Water soluble agents effective as immunological adjuvants for stimulating, in the host the immune response to various antigens and compositions, notably vaccines containing said water soluble agents |
-
1975
- 1975-12-10 CH CH1604275A patent/CH613709A5/en not_active IP Right Cessation
-
1976
- 1976-12-08 GR GR52361A patent/GR61647B/en unknown
- 1976-12-08 DE DE19762655500 patent/DE2655500A1/en active Granted
- 1976-12-08 CA CA000267474A patent/CA1262400A/en not_active Expired
- 1976-12-08 GB GB51228/76A patent/GB1570625A/en not_active Expired
- 1976-12-08 NL NL7613666A patent/NL7613666A/en not_active Application Discontinuation
- 1976-12-08 SU SU762428152A patent/SU660589A3/en active
- 1976-12-09 DD DD7600196215A patent/DD129781A5/en unknown
- 1976-12-09 CS CS768063A patent/CS205028B2/en unknown
- 1976-12-09 CS CS768063A patent/CS205025B2/en unknown
- 1976-12-09 PT PT65946A patent/PT65946B/en unknown
- 1976-12-09 BE BE173091A patent/BE849214A/en not_active IP Right Cessation
- 1976-12-09 IL IL51076A patent/IL51076A/en unknown
- 1976-12-09 HU HU76CI1702A patent/HU177970B/en unknown
- 1976-12-09 SE SE7613851A patent/SE445923B/en not_active IP Right Cessation
- 1976-12-09 DK DK552476A patent/DK154654C/en not_active IP Right Cessation
- 1976-12-09 AU AU20422/76A patent/AU508764B2/en not_active Expired
- 1976-12-09 NZ NZ182837A patent/NZ182837A/en unknown
- 1976-12-09 FR FR7637091A patent/FR2361902A1/en active Granted
- 1976-12-09 CS CS768063A patent/CS205027B2/en unknown
- 1976-12-09 IE IE2689/76A patent/IE44190B1/en not_active IP Right Cessation
- 1976-12-09 NO NO764191A patent/NO144850C/en unknown
- 1976-12-09 CS CS768063A patent/CS205026B2/en unknown
- 1976-12-09 AT AT0909276A patent/AT365607B/en not_active IP Right Cessation
- 1976-12-09 ZA ZA767333A patent/ZA767333B/en unknown
- 1976-12-09 FI FI763541A patent/FI64164C/en not_active IP Right Cessation
- 1976-12-10 PL PL1976210828A patent/PL110794B1/en unknown
- 1976-12-10 PL PL1976210827A patent/PL110787B1/en unknown
- 1976-12-10 PL PL1976194291A patent/PL110353B1/en not_active IP Right Cessation
- 1976-12-10 ES ES454118A patent/ES454118A1/en not_active Expired
- 1976-12-10 AR AR265799A patent/AR224091A1/en active
- 1976-12-10 PL PL1976210826A patent/PL112672B1/en unknown
- 1976-12-10 JP JP51147903A patent/JPS5273820A/en active Granted
-
1977
- 1977-09-08 SU SU772518658A patent/SU1060118A3/en active
- 1977-09-08 SU SU772521659A patent/SU747430A3/en active
- 1977-09-30 AR AR269405A patent/AR220686A1/en active
- 1977-12-28 ES ES465514A patent/ES465514A1/en not_active Expired
-
1978
- 1978-08-24 CH CH898378A patent/CH614718A5/en not_active IP Right Cessation
-
1983
- 1983-03-14 SG SG110/83A patent/SG11083G/en unknown
- 1983-08-25 HK HK328/83A patent/HK32883A/en unknown
-
1984
- 1984-12-30 MY MY123/84A patent/MY8400123A/en unknown
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |