IE831728L - Sugar derivatives in the treatment of virus infections - Google Patents
Sugar derivatives in the treatment of virus infectionsInfo
- Publication number
- IE831728L IE831728L IE831728A IE172883A IE831728L IE 831728 L IE831728 L IE 831728L IE 831728 A IE831728 A IE 831728A IE 172883 A IE172883 A IE 172883A IE 831728 L IE831728 L IE 831728L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- radical
- group
- substituted
- independently
- Prior art date
Links
- 230000009385 viral infection Effects 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 iminocarbonyl Chemical group 0.000 abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004429 atom Chemical group 0.000 abstract 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 abstract 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- GZCGUPFRVQAUEE-KCDKBNATSA-N aldehydo-D-galactose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-KCDKBNATSA-N 0.000 abstract 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 abstract 1
- GZCGUPFRVQAUEE-KVTDHHQDSA-N aldehydo-D-mannose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-KVTDHHQDSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- 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
-
- 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
- A61P31/12—Antivirals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
1. A pharmaceutical composition for enteral or parenteral application, which composition contains, as sole active ingredient, an effective amount, but less than 1 % by weight, of a compound of the formula I see diagramm : EP0102319,P31,F1 in which the sugar moiety is derived from (D)-galactose, (D)-mannose or (D)-glucose, which compound has at an asymmetrically substituted C(-R**3) atom the (D)-configuration, at an asymmetrically substituted C(-R**6) atom the (L)-configuration and at an asymmetrically substituted C(-R**8) atom the (D)-configuration, and in which compound each of X**1 and X**2 independently to the other represents a group of the formula -O- or -N(R**14)-, R**14 representing hydrogen or lower alkyl, each of R**1, R**2, R**12 and R**13 independently represents a radical of the formula Ia -(Z**1-Y**1-X**3)n -A**1 in which n represents 0 or 1, Z**1 represents carbonyl or thiocarbonyl, Y**1 represents unsubstituted or substituted alkylene which may be interrupted by iminocarbonyl or oxycarbonyl, X**3 represents a group of the formula -O- or -N(R**14)-, wherein R**14 has the meaning given above, and A**1 represents a radical of the formula Ib see diagramm : EP0102319,P31,F2 in which R**15 represents an aliphatic or cycloaliphatic radical having at least 7 carbon atoms, or A**1 represents a group of the formula Ic see diagramm : EP0102319,P31,F3 in which R**16 represents hydrogen and R**17 represents 2-hydroxyethyl or 1,2-dihydroxyethyl, wherein at least one hydroxy group is esterified or etherified by a radical having at least 7 carbon atoms, or in which each or R**16 and R**17 independently of the other represents esterified or etherified hydroxymethyl, the esterifying or etherifying radicals having at least 7 carbon atoms, or each of R**1, R**2, R**12 and R**13 independently represents hydrogen, acyl other than a radical of the formula Ia in which n represents 1, or aliphatically substituted silyl, each of R**3, R**4, R**5, R**7 and R**8 independently represents hydrogen or lower alkyl, R**6 represents hydrogen or lower alkyl that is unsubstituted or substituted by a group of the formula Id -E-(Z**2-Y**2-X**4)m -A**2 in which m represents 0 or 1, E represents a group of the formula -O-, -S- or -N(R**14), R**14 having the meaning given above, Z**2 represents carbonyl or thiocarbonyl, Y**2 represents unsubstituted or substituted alkylene which may be interrupted by iminocarbonyl or oxycarbonyl, X**4 represents a group of the formula -O- or -N(R**14)-, having the meaning given above, and A**2 represents a radical of the formula Ib or lc ; or by free or etherified hydroxy or mercapto, by esterified hydroxy or mercapto other than a group of the formula Id, by free amino or substituted amino other than a group of the formula Id, by free, esterified or amidated carboxy, by cycloalkyl, by carbocyclic aryl or by nitrogen-containing heteroaryl having 5 or 6 ring members in the heterocyclic ring, or R**5 and R**6 together represent unsubstituted 1,3- or 1,4-lower alkylene, each of R**9 and R**11 independently of the other represents a radical of the formula Ie -X**5-Y**3-X**6-A**3 in which X**5 represents a group of the formula -O-, -S- or -N(R**14)-, and X**6 represents a group of the formula -O- or -N(R**14)-, in each case R**14 having the meaning given above, Y**3 represents unsubstituted or substituted alkylene which may be interrupted by iminocarbonyl or oxycarbonyl, and A**3 represents a radical of the formula Id or lc, or free hydroxy or mercapto, etherified hydroxy or mercapto other than a radical of the formula Ie, or free amino or substituted amino other than a radical of the formula Ie, and represents hydrogen or free, esterified or amidated carboxy, with the proviso that radicals qualified by the term "lower" contain up to and including 7 carbon atoms and that the compounds of the formula I have at least one radical A**1, A**2 or A**3 and/or a pharmaceutically acceptable salt thereof, together with a pharmaceutical carrier.
[EP0102319A1]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH452882 | 1982-07-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE831728L true IE831728L (en) | 1984-01-23 |
| IE55793B1 IE55793B1 (en) | 1991-01-16 |
Family
ID=4277773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1728/83A IE55793B1 (en) | 1982-07-23 | 1983-07-22 | Use of sugar derivatives for the prophylaxis and treatment of virus infections |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0102319B1 (en) |
| JP (1) | JPS5933297A (en) |
| AU (1) | AU566879B2 (en) |
| BE (1) | BE897359A (en) |
| DE (1) | DE3326163A1 (en) |
| HK (1) | HK79890A (en) |
| IE (1) | IE55793B1 (en) |
| IL (1) | IL69294A (en) |
| IT (1) | IT1168778B (en) |
| NZ (1) | NZ205000A (en) |
| SG (1) | SG77989G (en) |
| ZA (1) | ZA835360B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3465087D1 (en) * | 1983-03-04 | 1987-09-03 | Merck & Co Inc | Immunostimulatory dipeptidyl d-glucose derivatives and methods of preparation |
| FR2564096B1 (en) * | 1984-05-11 | 1988-02-19 | Anvar | LIPOPHILIC DERIVATIVES OF MURAMYLPEPTIDES HAVING MACROPHAGE ACTIVATION PROPERTIES, COMPOSITIONS CONTAINING THEM AND PROCESS FOR OBTAINING THE SAME |
| US4885285A (en) * | 1984-09-13 | 1989-12-05 | Ciba-Geigy Corporation | Phosphorus compounds, processes for their manufacture, and their use |
| US4873322A (en) * | 1986-01-24 | 1989-10-10 | Ciba-Geigy Corporation | Saccharide derivatives and processes for their manufacture |
| DE4305552A1 (en) * | 1992-12-18 | 1994-06-23 | Rhone Poulenc Rorer Gmbh | Topical pharmaceutical or cosmetic compsn - contg N-acyl-alkanolamine, used for e.g. protecting skin against light or treating insect bites |
| GB9419011D0 (en) * | 1994-09-21 | 1994-11-09 | Peptech Uk Ltd | Use of muramyl peptide compounds |
| NZ550705A (en) * | 2004-03-22 | 2010-12-24 | Kode Biotech Ltd | Synthetic membrane anchors |
| CN109640959B (en) | 2016-04-29 | 2023-03-17 | 西奈山伊坎医学院 | Targeting the innate immune system to induce long-term tolerance and address macrophage accumulation in atherosclerosis |
| US11859021B2 (en) | 2021-03-19 | 2024-01-02 | Icahn School Of Medicine At Mount Sinai | Compounds for regulating trained immunity, and their methods of use |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI75578C (en) * | 1979-07-25 | 1988-07-11 | Ciba Geigy Ag | Analogous procedure for the preparation of pharmacologically acting lipophilic a phosphatidylmuramyl peptides. |
| FI803077A7 (en) * | 1979-10-12 | 1981-04-13 | Ciba Geigy Ag | FOERFARANDE FOER FRAMSTAELLNING AV MYRAMYLPEPTIDER |
| 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 |
| FR2498206A1 (en) * | 1981-01-19 | 1982-07-23 | Usinor | ASYMMETRICAL LEAD SHEETS AND THEIR PREPARATION METHOD |
| GR78246B (en) * | 1981-01-23 | 1984-09-26 | Ciba Geigy Ag | |
| US4697845A (en) * | 1985-08-02 | 1987-10-06 | The Quaker Oats Company | Long-running motor-driven baby swing |
-
1983
- 1983-07-18 EP EP83810324A patent/EP0102319B1/en not_active Expired
- 1983-07-20 DE DE19833326163 patent/DE3326163A1/en not_active Ceased
- 1983-07-21 IL IL69294A patent/IL69294A/en not_active IP Right Cessation
- 1983-07-22 JP JP58133010A patent/JPS5933297A/en active Pending
- 1983-07-22 AU AU17219/83A patent/AU566879B2/en not_active Expired
- 1983-07-22 ZA ZA835360A patent/ZA835360B/en unknown
- 1983-07-22 NZ NZ205000A patent/NZ205000A/en unknown
- 1983-07-22 IE IE1728/83A patent/IE55793B1/en not_active IP Right Cessation
- 1983-07-22 IT IT48734/83A patent/IT1168778B/en active
- 1983-07-25 BE BE0/211223A patent/BE897359A/en unknown
-
1989
- 1989-12-02 SG SG779/89A patent/SG77989G/en unknown
-
1990
- 1990-10-03 HK HK798/90A patent/HK79890A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HK79890A (en) | 1990-10-12 |
| JPS5933297A (en) | 1984-02-23 |
| EP0102319B1 (en) | 1987-08-19 |
| DE3326163A1 (en) | 1984-01-26 |
| IT8348734A0 (en) | 1983-07-22 |
| IE55793B1 (en) | 1991-01-16 |
| NZ205000A (en) | 1986-08-08 |
| SG77989G (en) | 1990-09-07 |
| BE897359A (en) | 1984-01-25 |
| EP0102319A1 (en) | 1984-03-07 |
| AU1721983A (en) | 1984-01-26 |
| ZA835360B (en) | 1985-03-27 |
| IL69294A0 (en) | 1983-11-30 |
| AU566879B2 (en) | 1987-11-05 |
| IL69294A (en) | 1987-03-31 |
| IT1168778B (en) | 1987-05-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |