DE3213650A1 - N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehr - Google Patents
N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehrInfo
- Publication number
- DE3213650A1 DE3213650A1 DE19823213650 DE3213650A DE3213650A1 DE 3213650 A1 DE3213650 A1 DE 3213650A1 DE 19823213650 DE19823213650 DE 19823213650 DE 3213650 A DE3213650 A DE 3213650A DE 3213650 A1 DE3213650 A1 DE 3213650A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- octadecyl
- glucopyranosyl
- carbon atoms
- 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.)
- Withdrawn
Links
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- 238000004519 manufacturing process Methods 0.000 title description 17
- 150000004649 carbonic acid derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000005917 acylation reaction Methods 0.000 claims description 6
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- 125000003147 glycosyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
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- 230000004727 humoral immunity Effects 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- CBDXTCKDOSHMMB-QJOIIPOXSA-N n-octadecyl-n-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]dodecanamide Chemical compound CCCCCCCCCCCCCCCCCCN(C(=O)CCCCCCCCCCC)C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O CBDXTCKDOSHMMB-QJOIIPOXSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- NSINWKBRCPSVRE-SRFONNGHSA-N (z)-n-octadecyl-n-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]octadec-9-enamide Chemical compound CCCCCCCCCCCCCCCCCCN(C(=O)CCCCCCC\C=C/CCCCCCCC)C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O NSINWKBRCPSVRE-SRFONNGHSA-N 0.000 claims description 2
- 230000003389 potentiating effect Effects 0.000 claims description 2
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- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 206010057249 Phagocytosis Diseases 0.000 claims 1
- 229930182470 glycoside Natural products 0.000 claims 1
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- 125000001483 monosaccharide substituent group Chemical group 0.000 claims 1
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- 239000000203 mixture Substances 0.000 abstract description 11
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 abstract description 3
- 210000000987 immune system Anatomy 0.000 abstract description 3
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 1
- -1 polyunsaturated alkyl radical Chemical class 0.000 description 81
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- 239000002904 solvent Substances 0.000 description 24
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- 235000000346 sugar Nutrition 0.000 description 22
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- 238000006243 chemical reaction Methods 0.000 description 20
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
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- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
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- 239000002253 acid Substances 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000427 antigen Substances 0.000 description 9
- 102000036639 antigens Human genes 0.000 description 9
- 108091007433 antigens Proteins 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000006181 N-acylation Effects 0.000 description 6
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
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- 239000006188 syrup Substances 0.000 description 6
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- 230000001225 therapeutic effect Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- 239000003085 diluting agent Substances 0.000 description 5
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- HDZVAKYKVBEOFL-GNADVCDUSA-N (2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-(octadecylamino)oxane-3,4,5-triol Chemical compound CCCCCCCCCCCCCCCCCCN[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HDZVAKYKVBEOFL-GNADVCDUSA-N 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MACBYOVDHSBNKZ-NCORMGPNSA-N n-[(3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-(octadecylamino)oxan-3-yl]acetamide Chemical compound CCCCCCCCCCCCCCCCCCNC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC(C)=O MACBYOVDHSBNKZ-NCORMGPNSA-N 0.000 description 1
- FHULBMYDBJJUKZ-QJOIIPOXSA-N n-[(3r,4s,5s,6s)-5-amino-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-n-octadecyldodecanamide Chemical compound CCCCCCCCCCCCCCCCCCN(C(=O)CCCCCCCCCCC)C1O[C@H](CO)[C@@H](N)[C@H](O)[C@H]1O FHULBMYDBJJUKZ-QJOIIPOXSA-N 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- ZUFFOCUETSRGEM-HHHGZCDHSA-N n-benzyl-n-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetamide Chemical compound C1([C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)N(C(=O)C)CC1=CC=CC=C1 ZUFFOCUETSRGEM-HHHGZCDHSA-N 0.000 description 1
- WFMKUKPIVUIKTE-QJOIIPOXSA-N n-dodecyl-n-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)N(CCCCCCCCCCCC)C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O WFMKUKPIVUIKTE-QJOIIPOXSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RAYXSECBYMUYIN-RKFWXSKXSA-N n-octadecyl-n-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]hexadecanamide Chemical compound CCCCCCCCCCCCCCCCCCN(C(=O)CCCCCCCCCCCCCCC)C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RAYXSECBYMUYIN-RKFWXSKXSA-N 0.000 description 1
- HSTYAETYVBRUKQ-DSMSILMNSA-N n-octadecyl-n-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCCN(C(=O)CCCCCCCCCCCCCCCCC)C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HSTYAETYVBRUKQ-DSMSILMNSA-N 0.000 description 1
- UREJYVIZZWPATM-OOTDLNEOSA-N n-octadecyl-n-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]tetradecanamide Chemical compound CCCCCCCCCCCCCCCCCCN(C(=O)CCCCCCCCCCCCC)C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UREJYVIZZWPATM-OOTDLNEOSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 230000015323 positive regulation of phagocytosis Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 208000037920 primary disease Diseases 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- 125000003132 pyranosyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- LPWCRLGKYWVLHQ-UHFFFAOYSA-N tetradecanoyl chloride Chemical compound CCCCCCCCCCCCCC(Cl)=O LPWCRLGKYWVLHQ-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
- C07H13/04—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 attached to acyclic carbon atoms
-
- 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
- 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
- C07H13/04—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 attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Hydrogenated Pyridines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823213650 DE3213650A1 (de) | 1982-04-14 | 1982-04-14 | N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehr |
| AU12615/83A AU561016B2 (en) | 1982-04-14 | 1983-03-21 | N-glycosylated carboxamide derivatives |
| NO831163A NO157145C (no) | 1982-04-14 | 1983-03-29 | Analogifremgangsmaate til fremstilling av terapeutisk aktive n-glykosylerte karboksylsyreamidderivater. |
| PT76502A PT76502B (en) | 1982-04-14 | 1983-04-05 | Process for the preparation of n-glycosylated carboxamide derivatives with s stimulating effect of the body's inherent defences and their application for the preparation of pharmaceutical compositions having a stimulating effect of body's inherent defences |
| EP83103325A EP0091645B1 (de) | 1982-04-14 | 1983-04-06 | N-glycosylierte Carbonsäureamid-Derivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Beeinflussung der körpereigenen Abwehr |
| DE8383103325T DE3369851D1 (en) | 1982-04-14 | 1983-04-06 | Derivatives of amides of carboxylic acids in which the n atom is substituted by a glycosyl radical, method for their preparation and their use to influence the immunogenic system |
| AT83103325T ATE25525T1 (de) | 1982-04-14 | 1983-04-06 | N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehr. |
| JP58061065A JPS58188891A (ja) | 1982-04-14 | 1983-04-08 | Ｎ―グリコシルカルボキサミド誘導体、その製造方法及び該誘導体を含有する抗感染力強化剤 |
| IL68350A IL68350A (en) | 1982-04-14 | 1983-04-11 | N-glycosylated carboxamide derivatives,their preparation and their use for the treatment of animals |
| PH28763A PH25527A (en) | 1982-04-14 | 1983-04-12 | N-glycosylated carboxamide derivatives |
| GR71057A GR78512B (enExample) | 1982-04-14 | 1983-04-12 | |
| CA000425694A CA1230594A (en) | 1982-04-14 | 1983-04-12 | N-glycosylated carboxamide derivatives, process for their preparation and their use for influencing the body's inherent defences |
| FI831230A FI75172C (fi) | 1982-04-14 | 1983-04-12 | Foerfarande foer framstaellning av terapeutiskt anvaendbara n-glykosylerade karboksylsyraamidderivat. |
| DK162883A DK162883A (da) | 1982-04-14 | 1983-04-13 | N-glucosylerede carboxylsyreamidderivater, fremgangsmaade til fremstilling heraf samt deres anvendelse til paavirkning af organismens egen forsvarsmekanisme |
| ZA832580A ZA832580B (en) | 1982-04-14 | 1983-04-13 | N-glycosylated carboxamide derivatives,process for their preparation and their use for influencing the body's inherent defences |
| ES521422A ES521422A0 (es) | 1982-04-14 | 1983-04-13 | Procedimiento para la obtencion de derivados de carboxilamida n-glicosilados. |
| IE840/83A IE55112B1 (en) | 1982-04-14 | 1983-04-13 | N-glycosylated carboxamide derivatives,process for their preparation and their use for influencing the body's inherent defences |
| HU831306A HU194262B (en) | 1982-04-14 | 1983-04-14 | Process for producing new glycozilized derivatives of carboxylic-amides and pharmaceutical compositions containing them |
| KR1019830001562A KR920000312B1 (ko) | 1982-04-14 | 1983-04-14 | N-글리코실화 카복스아미드 유도체의 제조방법 |
| US06/725,060 US4683222A (en) | 1982-04-14 | 1985-04-19 | N-glycosylated carboxamide derivatives and their use for influencing the body's inherent defences |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823213650 DE3213650A1 (de) | 1982-04-14 | 1982-04-14 | N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehr |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3213650A1 true DE3213650A1 (de) | 1983-10-27 |
Family
ID=6160842
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823213650 Withdrawn DE3213650A1 (de) | 1982-04-14 | 1982-04-14 | N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehr |
| DE8383103325T Expired DE3369851D1 (en) | 1982-04-14 | 1983-04-06 | Derivatives of amides of carboxylic acids in which the n atom is substituted by a glycosyl radical, method for their preparation and their use to influence the immunogenic system |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383103325T Expired DE3369851D1 (en) | 1982-04-14 | 1983-04-06 | Derivatives of amides of carboxylic acids in which the n atom is substituted by a glycosyl radical, method for their preparation and their use to influence the immunogenic system |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4683222A (enExample) |
| EP (1) | EP0091645B1 (enExample) |
| JP (1) | JPS58188891A (enExample) |
| KR (1) | KR920000312B1 (enExample) |
| AT (1) | ATE25525T1 (enExample) |
| AU (1) | AU561016B2 (enExample) |
| CA (1) | CA1230594A (enExample) |
| DE (2) | DE3213650A1 (enExample) |
| DK (1) | DK162883A (enExample) |
| ES (1) | ES521422A0 (enExample) |
| FI (1) | FI75172C (enExample) |
| GR (1) | GR78512B (enExample) |
| HU (1) | HU194262B (enExample) |
| IE (1) | IE55112B1 (enExample) |
| IL (1) | IL68350A (enExample) |
| NO (1) | NO157145C (enExample) |
| PH (1) | PH25527A (enExample) |
| PT (1) | PT76502B (enExample) |
| ZA (1) | ZA832580B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995006654A1 (de) * | 1993-08-30 | 1995-03-09 | Bayer Aktiengesellschaft | Glycosylamide von 2-aminoacylamino-2-desoxy-zuckern |
| WO1995006655A1 (de) * | 1993-08-30 | 1995-03-09 | Bayer Aktiengesellschaft | (glycosylamid)-uronsäure-derivate |
| WO1995006653A1 (de) * | 1993-08-30 | 1995-03-09 | Bayer Aktiengesellschaft | Glycosylamide von 6-amino-6-desoxy-zuckern |
| EP2481423A1 (en) | 2006-01-26 | 2012-08-01 | Pfizer Products Inc. | Novel glycolipid adjuvant compositions |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3213650A1 (de) * | 1982-04-14 | 1983-10-27 | Bayer Ag, 5090 Leverkusen | N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehr |
| DE3339694A1 (de) * | 1983-11-03 | 1985-05-15 | Bayer Ag, 5090 Leverkusen | Verwendung n-glycosilierter carbonsaeureamid-derivate als wachstumsfoerderer in der tierernaehrung |
| DE3403495A1 (de) * | 1983-11-23 | 1985-05-30 | Bayer Ag, 5090 Leverkusen | Phosphorylierte glycosylamide, -harnstoffe, -carbamate und -thiocarbamate, verfahren zu ihrer herstellung sowie ihre verwendung |
| DE3344257A1 (de) * | 1983-12-07 | 1985-06-13 | Bayer Ag, 5090 Leverkusen | Substituierte o-acyl-glycosylamide, verfahren zu iherer herstellung sowie ihre verwendung |
| DE3346623A1 (de) * | 1983-12-14 | 1985-07-04 | Bayer Ag, 5090 Leverkusen | N-glycosylierte harnstoffe, carbamate und thiocarbamate, verfahren zu ihrer herstellung sowie ihre verwendung |
| DE3347522A1 (de) * | 1983-12-30 | 1985-07-11 | Troponwerke GmbH & Co KG, 5000 Köln | N-glycosylierte carbonsaeureamid-derivate als mittel bei der bekaempfung von erkrankungen des rheumatischen formenkreises |
| DE3410238A1 (de) * | 1984-03-21 | 1985-10-03 | Bayer Ag, 5090 Leverkusen | Glycolipid-aehnliche substanzen in liposomenform |
| DE3508025A1 (de) * | 1985-03-07 | 1986-09-11 | Bayer Ag, 5090 Leverkusen | Substituierte o-sulfonyl-glycosylamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE3521994A1 (de) * | 1985-06-20 | 1987-01-02 | Bayer Ag | N-(2-aminoacylamido-2-desoxy-hexosyl)-amide-, -carbamate und -harnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| DE3604681A1 (de) * | 1986-02-14 | 1987-08-20 | Bayer Ag | Neue n-glycosylamidderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE3812681A1 (de) * | 1988-04-16 | 1989-11-02 | Bayer Ag | Substituierte n-glycosylamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US5476924A (en) * | 1989-01-27 | 1995-12-19 | Duke University | Protecting group for acetals and methods of using the same in the activation of saccharides |
| FR2676739B1 (fr) * | 1991-05-22 | 1996-10-11 | Stepan Europe | N-alkyl, n-acetylosylamines, leur procede de preparation et leurs utilisations notamment en tant qu'agents tensioactifs ou agents de solubilisation pour l'isolement de proteines membranaires. |
| US5362480A (en) * | 1991-12-31 | 1994-11-08 | Lever Brothers Company, Division Of Conopco, Inc. | Oral hygiene compositions containing amino sugars as antiplaque agents |
| US5455232A (en) * | 1992-02-04 | 1995-10-03 | Piljac; Goran | Pharmaceutical preparation based on rhamnolipid |
| FR2709061B1 (fr) * | 1993-08-17 | 1996-07-19 | Ladislas Robert | Utilisation d'oligosaccharides dans la prévention et le traitement du vieillissement des tissus. |
| AU4371996A (en) * | 1994-12-16 | 1996-07-03 | Alcon Laboratories, Inc. | Ophthalmic formulations of substituted glycosides |
| US6290971B1 (en) * | 1995-06-15 | 2001-09-18 | Aventis Pasteur Limited | Adjuvant compositions comprising a mineral salt and another immunostimulating compound |
| US5872111A (en) * | 1997-05-19 | 1999-02-16 | Lever Brothers Company, Division Of Conopco, Inc. | Compositions comprising glycosylamide surfactants |
| US6670330B1 (en) * | 2000-05-01 | 2003-12-30 | Theodore J. Lampidis | Cancer chemotherapy with 2-deoxy-D-glucose |
| JP3664401B2 (ja) * | 2003-01-22 | 2005-06-29 | 独立行政法人科学技術振興機構 | Ｎ−グリコシド型糖脂質及びこれから成る中空繊維状有機ナノチューブ |
| US20050008699A1 (en) * | 2003-07-11 | 2005-01-13 | Fred Wehling | Effervescent glucosamine composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2808402A (en) * | 1954-08-19 | 1957-10-01 | Rohm & Haas | Method for preparing nu-sorbitylcarbamates |
| DE1261861B (de) * | 1963-08-22 | 1968-02-29 | Dehydag Gmbh | Verfahren zur Herstellung von Glycaminabkoemmlingen |
| FR2187324B1 (enExample) * | 1972-06-14 | 1975-06-20 | Rech Pharmaceut Sc | |
| US4228274A (en) * | 1976-09-28 | 1980-10-14 | Merck & Co., Inc. | 1-Substituted glycopyranosides |
| JPS5649396A (en) * | 1979-09-28 | 1981-05-02 | Dai Ichi Seiyaku Co Ltd | Novel muramyldipeptide derivative |
| DE3213650A1 (de) * | 1982-04-14 | 1983-10-27 | Bayer Ag, 5090 Leverkusen | N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehr |
-
1982
- 1982-04-14 DE DE19823213650 patent/DE3213650A1/de not_active Withdrawn
-
1983
- 1983-03-21 AU AU12615/83A patent/AU561016B2/en not_active Ceased
- 1983-03-29 NO NO831163A patent/NO157145C/no unknown
- 1983-04-05 PT PT76502A patent/PT76502B/pt unknown
- 1983-04-06 DE DE8383103325T patent/DE3369851D1/de not_active Expired
- 1983-04-06 AT AT83103325T patent/ATE25525T1/de not_active IP Right Cessation
- 1983-04-06 EP EP83103325A patent/EP0091645B1/de not_active Expired
- 1983-04-08 JP JP58061065A patent/JPS58188891A/ja active Granted
- 1983-04-11 IL IL68350A patent/IL68350A/xx unknown
- 1983-04-12 GR GR71057A patent/GR78512B/el unknown
- 1983-04-12 CA CA000425694A patent/CA1230594A/en not_active Expired
- 1983-04-12 PH PH28763A patent/PH25527A/en unknown
- 1983-04-12 FI FI831230A patent/FI75172C/fi not_active IP Right Cessation
- 1983-04-13 IE IE840/83A patent/IE55112B1/en unknown
- 1983-04-13 DK DK162883A patent/DK162883A/da not_active Application Discontinuation
- 1983-04-13 ZA ZA832580A patent/ZA832580B/xx unknown
- 1983-04-13 ES ES521422A patent/ES521422A0/es active Granted
- 1983-04-14 KR KR1019830001562A patent/KR920000312B1/ko not_active Expired
- 1983-04-14 HU HU831306A patent/HU194262B/hu not_active IP Right Cessation
-
1985
- 1985-04-19 US US06/725,060 patent/US4683222A/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995006654A1 (de) * | 1993-08-30 | 1995-03-09 | Bayer Aktiengesellschaft | Glycosylamide von 2-aminoacylamino-2-desoxy-zuckern |
| WO1995006655A1 (de) * | 1993-08-30 | 1995-03-09 | Bayer Aktiengesellschaft | (glycosylamid)-uronsäure-derivate |
| WO1995006653A1 (de) * | 1993-08-30 | 1995-03-09 | Bayer Aktiengesellschaft | Glycosylamide von 6-amino-6-desoxy-zuckern |
| EP2481423A1 (en) | 2006-01-26 | 2012-08-01 | Pfizer Products Inc. | Novel glycolipid adjuvant compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| FI75172B (fi) | 1988-01-29 |
| DK162883A (da) | 1983-10-15 |
| ES8402313A1 (es) | 1984-01-16 |
| ES521422A0 (es) | 1984-01-16 |
| EP0091645A1 (de) | 1983-10-19 |
| PH25527A (en) | 1991-07-24 |
| IL68350A0 (en) | 1983-07-31 |
| FI75172C (fi) | 1988-05-09 |
| DK162883D0 (da) | 1983-04-13 |
| AU561016B2 (en) | 1987-04-30 |
| PT76502B (en) | 1985-12-10 |
| ATE25525T1 (de) | 1987-03-15 |
| JPH0140036B2 (enExample) | 1989-08-24 |
| PT76502A (en) | 1983-05-01 |
| AU1261583A (en) | 1983-10-20 |
| JPS58188891A (ja) | 1983-11-04 |
| IL68350A (en) | 1988-09-30 |
| NO157145B (no) | 1987-10-19 |
| DE3369851D1 (en) | 1987-04-02 |
| US4683222A (en) | 1987-07-28 |
| KR920000312B1 (ko) | 1992-01-11 |
| FI831230A0 (fi) | 1983-04-12 |
| ZA832580B (en) | 1984-01-25 |
| HU194262B (en) | 1988-01-28 |
| EP0091645B1 (de) | 1987-02-25 |
| KR840004761A (ko) | 1984-10-24 |
| IE830840L (en) | 1983-10-14 |
| FI831230L (fi) | 1983-10-15 |
| NO157145C (no) | 1988-01-27 |
| CA1230594A (en) | 1987-12-22 |
| NO831163L (no) | 1983-10-17 |
| IE55112B1 (en) | 1990-06-06 |
| GR78512B (enExample) | 1984-09-27 |
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